CN1630643A - 用作除草剂的取代的苯甲酰基环己烷二酮类化合物 - Google Patents
用作除草剂的取代的苯甲酰基环己烷二酮类化合物 Download PDFInfo
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- CN1630643A CN1630643A CNA008189897A CN00818989A CN1630643A CN 1630643 A CN1630643 A CN 1630643A CN A008189897 A CNA008189897 A CN A008189897A CN 00818989 A CN00818989 A CN 00818989A CN 1630643 A CN1630643 A CN 1630643A
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- Prior art keywords
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- methyl
- amino
- alkyl
- bases
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- XKLPBDMZJSWRBL-UHFFFAOYSA-N 3-benzoylcyclohexane-1,2-dione Chemical class C=1C=CC=CC=1C(=O)C1CCCC(=O)C1=O XKLPBDMZJSWRBL-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 239000004009 herbicide Substances 0.000 title abstract description 5
- 238000002360 preparation method Methods 0.000 claims abstract description 36
- 238000000034 method Methods 0.000 claims abstract description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- 239000000460 chlorine Substances 0.000 claims description 171
- -1 thiocarbamyl Chemical class 0.000 claims description 152
- 150000001875 compounds Chemical class 0.000 claims description 73
- 229910052801 chlorine Inorganic materials 0.000 claims description 45
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 45
- 241000196324 Embryophyta Species 0.000 claims description 44
- 239000001257 hydrogen Substances 0.000 claims description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims description 40
- 239000011737 fluorine Substances 0.000 claims description 38
- 229910052731 fluorine Inorganic materials 0.000 claims description 38
- 229910052799 carbon Inorganic materials 0.000 claims description 37
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 36
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 36
- 150000001721 carbon Chemical group 0.000 claims description 29
- 150000002431 hydrogen Chemical class 0.000 claims description 29
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 26
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 24
- 229910052736 halogen Inorganic materials 0.000 claims description 23
- 150000002367 halogens Chemical class 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 19
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 18
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 17
- 229910052794 bromium Inorganic materials 0.000 claims description 17
- 239000003795 chemical substances by application Substances 0.000 claims description 16
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 15
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 14
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 11
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- JSLZUBLGGPEVQN-DIPNUNPCSA-N (2r)-4-methyl-2-propan-2-yl-2-[2-[4-[4-[2-(3,4,5-trimethoxyphenyl)ethyl]piperazin-1-yl]butoxy]phenyl]-1,4-benzothiazin-3-one Chemical compound COC1=C(OC)C(OC)=CC(CCN2CCN(CCCCOC=3C(=CC=CC=3)[C@@]3(C(N(C)C4=CC=CC=C4S3)=O)C(C)C)CC2)=C1 JSLZUBLGGPEVQN-DIPNUNPCSA-N 0.000 claims description 8
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
- 239000011630 iodine Substances 0.000 claims description 8
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- 229950001891 iprotiazem Drugs 0.000 claims description 8
- 239000013543 active substance Substances 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
- 125000001118 alkylidene group Chemical group 0.000 claims description 6
- 125000003368 amide group Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 6
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 6
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 230000002363 herbicidal effect Effects 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 159000000000 sodium salts Chemical class 0.000 claims description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 4
- 150000003863 ammonium salts Chemical class 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 4
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims description 4
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 4
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 4
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 4
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims description 4
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 4
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 4
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 4
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 2
- 239000005711 Benzoic acid Substances 0.000 claims description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims description 2
- 241000405414 Rehmannia Species 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 235000010233 benzoic acid Nutrition 0.000 claims description 2
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 2
- 125000006309 butyl amino group Chemical group 0.000 claims description 2
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 2
- 159000000007 calcium salts Chemical class 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 2
- 125000006311 cyclobutyl amino group Chemical group [H]N(*)C1([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 2
- 125000006312 cyclopentyl amino group Chemical group [H]N(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000006317 cyclopropyl amino group Chemical group 0.000 claims description 2
- 125000004914 dipropylamino group Chemical group C(CC)N(CCC)* 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 claims description 2
- 159000000003 magnesium salts Chemical class 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
- 239000001103 potassium chloride Substances 0.000 claims description 2
- 235000011164 potassium chloride Nutrition 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 17
- 230000002508 compound effect Effects 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract description 3
- 125000002947 alkylene group Chemical group 0.000 abstract 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 20
- 150000004702 methyl esters Chemical class 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
- 244000025254 Cannabis sativa Species 0.000 description 11
- 230000000694 effects Effects 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000002994 raw material Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 7
- PXHFWPOPKVWXQT-UHFFFAOYSA-N 3-methyl-1h-imidazol-2-one Chemical compound CN1C=CN=C1O PXHFWPOPKVWXQT-UHFFFAOYSA-N 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- 125000004494 ethyl ester group Chemical group 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 description 5
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 5
- 235000010755 mineral Nutrition 0.000 description 5
- 239000011707 mineral Substances 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000002243 precursor Substances 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 241000209140 Triticum Species 0.000 description 4
- 235000021307 Triticum Nutrition 0.000 description 4
- 230000001419 dependent effect Effects 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 235000021506 Ipomoea Nutrition 0.000 description 3
- 241000207783 Ipomoea Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
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- 235000006443 Panicum miliaceum subsp. miliaceum Nutrition 0.000 description 3
- 235000009037 Panicum miliaceum subsp. ruderale Nutrition 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 238000006480 benzoylation reaction Methods 0.000 description 3
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- 230000008029 eradication Effects 0.000 description 3
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 3
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- 239000008187 granular material Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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- 229920000151 polyglycol Polymers 0.000 description 3
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
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- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
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- PVSGXWMWNRGTKE-UHFFFAOYSA-N 5-methyl-2-[4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl]pyridine-3-carboxylic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC=C(C)C=C1C(O)=O PVSGXWMWNRGTKE-UHFFFAOYSA-N 0.000 description 2
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- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
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- 241000209510 Liliopsida Species 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D239/08—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms directly attached in position 2
- C07D239/10—Oxygen or sulfur atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
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- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明涉及新的通式(I)的取代的苯甲酰基环己烷二酮类化合物,其中,A1代表单键或具有1-3个碳原子的亚烷基,A2代表具有1-3个碳原子的亚烷基,R1、R2、R3、R4和R5各具有说明书中给出的含义。本发明还涉及它们的中间体、制备它们的方法和它们作为除草剂应用。
Description
本发明涉及新的取代的苯甲酰基环己烷二酮类化合物、它们的制备方法和它们作为除草剂的应用。
已经知道,某些取代的苯甲酰基环己烷二酮类化合物具有除草性能(参见EP-A-090262、EP-A-135191、EP-A-186118、EP-A-186119、EP-A-186120、EP-A-319075、DE-A-199 21 732、WO-A-96/26200、WO-A-97/46530、WO-A-99/07688)。然而,这些化合物的活性并不是在所有方面都是令人满意的。
其它的取代的苯甲酰基环己烷二酮类化合物是一个早先的、但未在先公开的专利申请的部分主题(参见DE-A-19 921 732)。
因此,本发明提供了新的通式(I)的取代的苯甲酰基环己烷二酮类化合物:
其中
A1代表单键或具有1-3个碳原子的亚烷基,
A2代表具有1-3个碳原子的亚烷基,
R1代表氢,代表苯基,或代表各自任选被卤素取代的、各自在烷基中具有1-4个碳原子的烷基、烷硫基或烷氧基羰基,
R2代表氢,或代表各自任选被卤素取代的、各自具有1-4个碳原子的烷基或烷硫基,或与R1一起代表具有最多4个碳原子的亚烷基,或——如果R1和R2连在同一个碳原子上——与R1还有R1和R2所连的碳原子一起代表羰基(C=O),
R3代表氢、硝基、氰基、羧基、氨甲酰基、硫代氨甲酰基、卤素,代表各自任选被卤素取代的、在烷基中各具有1-4个碳原子的烷基、烷氧基、烷硫基、烷基亚磺酰基、烷基磺酰基、烷基氨基、二烷基氨基、烷基磺酰基氨基或二烷基氨基磺酰基,或代表各自任选被卤素或C1-C4-烷基取代的各具有3-6个碳原子的环烷基氨基、环烷基磺酰基、环烷基磺酰基氨基或环烷基氨基磺酰基,
R4代表氢、硝基、氰基、羧基、氨甲酰基、硫代氨甲酰基、卤素,或代表各自任选被卤素取代的、在烷基中各具有1-4个碳原子的烷基、烷氧基、烷硫基、烷基亚磺酰基、烷基磺酰基、烷基氨基、二烷基氨基或二烷基氨基磺酰基,
R5代表氢,代表氨基,代表各自任选被氨基、氰基、卤素或C1-C4-烷氧基取代的、在烷基中各具有1-5个碳原子的烷基、烷氧基、烷基氨基、二烷基氨基、烷基磺酰基或烷基磺酰基氨基,代表各自任选被卤素取代的、各自具有最多5个碳原子的链烯基或炔基,代表各自任选被氰基、卤素或C1-C4-烷基取代的在环烷基中各具有3-6个碳原子和任选地在烷基中各自具有1-3个碳原子的环烷基或环烷基烷基,代表具有5或6个碳原子的环烯基,或代表各自任选被硝基、氰基、羧基、卤素、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基或C1-C4-卤代烷氧基取代的苯基、苯基-C1-C4-烷基、吡啶基或嘧啶基,
排除化合物1-[2,6-二氯-3-[(2-羟基-6-氧代-环己烯-1-基)羰基]苄基]-3-甲基-四氢-2(1H)-嘧啶酮(参见DE-A-19 921 732,表2,实施例ID-1)。
本发明还提供了通式(I)化合物的所有可能的互变异构形式和通式(I)化合物的可能的盐和金属配合物。
在上述定义中,烃链如烷基或烷二基,也包括与杂原子结合的情况如在烷氧基中时,各自是直链或支链的。
除了上述通式(I)化合物外,在各自情况下也可以存在如下例示的相应的互变异构形式:
优选的、上述各式中所列的基团/取代基的意义具体说明如下:
A1优选代表单键,代表亚甲基、乙烷-1,1-二基、乙烷-1,2-二基、丙烷-1,1-二基、丙烷-1,2-二基或丙烷-1,3-二基。
A2优选代表亚甲基、乙烷-1,1-二基、乙烷-1,2-二基、丙烷-1,1-二基、丙烷-1,2-二基或丙烷-1,3-二基。
R1优选代表氢,优选代表苯基,或优选代表各自任选被氟和/或氯取代的甲基、乙基、正-或异-丙基、甲硫基、乙硫基、正-或异丙硫基、甲氧基羰基、乙氧基羰基、正-或异丙氧基羰基。
R2优选代表氢,或优选代表各自任选被氟和/或氯取代的甲基、乙基、正或异-丙基、甲硫基、乙硫基、正-或异丙硫基,或与R1一起优选代表亚甲基、乙烷-1,1-二基、乙烷-1,2-二基、丙烷-1,1-二基、丙烷-1,2-二基或丙烷-1,3-二基,或——如果R1和R2连在同一个碳原子上——与R1还有R1和R2所连的碳原子一起优选代表羰基(C=O)。
R3优选代表氢、硝基、氰基、羧基、氨甲酰基、硫代氨甲酰基、氟、氯、溴、碘,优选代表各自任选被氟和/或氯取代的甲基、乙基、正或异-丙基、甲氧基、乙氧基、正或异-丙氧基、甲硫基、乙硫基、正-或异丙硫基、甲基亚磺酰基、乙基亚磺酰基、正或异-丙基亚磺酰基、甲基磺酰基、乙基磺酰基、正或异-丙基磺酰基,优选代表甲基氨基、乙基氨基、正或异-丙基氨基、二甲基氨基、二乙基氨基、甲基磺酰基氨基、乙基磺酰基氨基、正或异-丙基磺酰基氨基、二甲基氨基磺酰基或二乙基氨基磺酰基,或优选代表各自任选被氟、氯或甲基取代的环丙基氨基、环丁基氨基、环戊基氨基、环己基氨基、环丙基磺酰基、环丁基磺酰基、环戊基磺酰基、环己基磺酰基、环丙基磺酰基氨基、环丁基磺酰基氨基、环戊基磺酰基氨基、环己基磺酰基氨基、环丙基氨基磺酰基、环丁基氨基磺酰基、环戊基氨基磺酰基或环己基氨基磺酰基。
R4优选代表氢、硝基、氰基、羧基、氨甲酰基、硫代氨甲酰基、氟、氯、溴、碘,或优选代表各自任选被氟和/或氯取代的甲基、乙基、正或异-丙基、甲氧基、乙氧基、正或异-丙氧基、甲硫基、乙硫基、正-或异丙硫基、甲基亚磺酰基、乙基亚磺酰基、正或异-丙基亚磺酰基、甲基磺酰基、乙基磺酰基、正或异-丙基磺酰基,优选代表甲基氨基、乙基氨基、正或异-丙基氨基、二甲基氨基、二乙基氨基、二甲基氨基磺酰基或二乙基氨基磺酰基。
R5优选代表氢,优选代表氨基,优选代表各自任选被氨基、氰基、氟和/或氯、甲氧基或乙氧基取代的甲基、乙基、正或异-丙基、正-、异-、仲-或叔丁基、甲氧基、乙氧基、正或异-丙氧基、正-、异-、仲-或叔丁氧基、甲基氨基、乙基氨基、正或异-丙基氨基、正-、异-、仲-或叔丁基氨基、二甲基氨基、二乙基氨基、二丙基氨基、甲基磺酰基、乙基磺酰基或甲基磺酰基氨基,或优选代表各自任选被氟、氯和/或溴取代的丙烯基、丁烯基、丙炔基或丁炔基,优选代表各自任选被氰基、氟、氯、甲基或乙基取代的环丙基、环丁基、环戊基、环己基、环丙基甲基、环丁基甲基、环戊基甲基或环己基甲基,优选代表环己烯基,或优选代表各自任选被氟、氯、溴、甲基、三氟甲基、甲氧基、二氟甲氧基或三氟甲氧基取代的苯基、苄基、吡啶基或嘧啶基。
A1特别优选代表单键,代表亚甲基、乙烷-1,2-二基或丙烷-1,3-二基。
A2特别优选代表亚甲基、乙烷-1,2-二基或丙烷-1,3-二基。
R1特别优选代表氢、苯基、甲基、乙基、正-或异-丙基、甲硫基、乙硫基、甲氧基羰基或乙氧基羰基。
R2特别优选代表氢、甲基、乙基、甲硫基、乙硫基,或与R1一起特别优选代表亚甲基、乙烷-1,2-二基或丙烷-1,3-二基,或——如果R1和R2连在同一个碳原子上——与R1还有R1和R2所连的碳原子一起特别优选代表羰基(C=O)。
R3特别优选代表氢、硝基、氰基、氟、氯、溴、碘,特别优选代表各自任选被氟和/或氯取代的甲基、乙基、甲氧基、乙氧基、甲硫基、乙硫基、甲基亚磺酰基、乙基亚磺酰基、甲基磺酰基、乙基磺酰基,特别优选代表甲基氨基、乙基氨基、二甲基氨基或二甲基氨基磺酰基。
R4特别优选代表氢、硝基、氰基、氟、氯、溴、碘,或特别优选代表各自任选被氟和/或氯取代的甲基、乙基、甲氧基、乙氧基、甲硫基、乙硫基、甲基亚磺酰基、乙基亚磺酰基、甲基磺酰基、乙基磺酰基,特别优选代表甲基氨基、乙基氨基、二甲基氨基或二甲基氨基磺酰基。
R5特别优选代表氢、甲基、乙基、正或异-丙基、正-、异-、仲-或叔丁基、丙烯基、丙炔基、环丙基、环戊基、环己基、环丙基甲基、环戊基甲基、环己基甲基、苯基或苄基。
A1非常特别优选代表亚甲基或乙烷-1,2-二基。
A2非常特别优选代表亚甲基或乙烷-1,2-二基。
R1非常特别优选代表氢、苯基、甲基、乙基、正-或异-丙基、甲硫基或乙硫基。
R2非常特别优选代表氢、甲基、乙基、甲硫基,或与R1一起非常特别优选代表乙烷-1,2-二基或丙烷-1,3-二基,或——如果R1和R2连在同一个碳原子上——与R1还有R1和R2所连的碳原子一起非常特别优选代表羰基(C=O)。
R3非常特别优选代表氢、硝基、氰基、氟、氯、溴、甲基、二氟甲基、三氟甲基、二氯甲基、三氯甲基、氯二氟甲基、乙基、甲氧基、二氟甲氧基、三氟甲氧基、氯二氟甲氧基、乙氧基、甲硫基、二氟甲硫基、三氟甲硫基、氯二氟甲硫基、乙硫基、甲基亚磺酰基、三氟甲基亚磺酰基、乙基亚磺酰基、甲基磺酰基、三氟甲基磺酰基、乙基磺酰基、二甲基氨基或二甲基氨基磺酰基。
R4非常特别优选代表氢、硝基、氰基、氟、氯、溴、甲基、二氟甲基、三氟甲基、二氯甲基、三氯甲基、氯二氟甲基、乙基、甲氧基、二氟甲氧基、三氟甲氧基、氯二氟甲氧基、乙氧基、甲硫基、二氟甲硫基、三氟甲硫基、氯二氟甲硫基、乙硫基、甲基亚磺酰基、三氟甲基亚磺酰基、乙基亚磺酰基、甲基磺酰基、三氟甲基磺酰基、乙基磺酰基、二甲基氨基或二甲基氨基磺酰基。
R5非常特别优选代表氢、甲基、乙基、正或异-丙基、正-、异-、仲-或叔丁基、环丙基、环戊基或环己基。
本发明也优选提供其中A1、A2、R1、R2、R3、R4和R5各如上所定义的式(I)化合物的钠盐、钾盐、镁盐、钙盐、铵盐、C1-C4-烷基铵盐、二-(C1-C4-烷基)-铵盐、三-(C1-C4-烷基)-铵盐、四-(C1-C4-烷基)-铵盐、三-(C1-C4-烷基)-锍盐、C5-或C6-环烷基-铵盐和二-(C1-C2-烷基)-苄基铵盐,或这些化合物与金属如铜、铁、钴、镍的配合物化合物(配位化合物)。
本发明优选的是含有上面所列优选含义组合的式(I)化合物。
本发明特别优选的是含有上面所列特别优选含义组合的式(I)化合物。
本发明非常特别优选的是含有上面所列非常特别优选含义组合的式(I)化合物。
上面提到的一般或优选的基团定义适合于式(I)终产物,且相应地,也适合于在每一种情况下制备所需的起始原料或中间体。这些基团定义可以按照需要相互结合,也包括给定的优选范围间的组合。
根据本发明特别强调的是下列式(IA)、(IB)和(IC)的化合物,其中A1、A2、R1、R2、R3和R4各具有上面作为非常特别优选给出的含义:
新的通式(I)的取代的苯甲酰基环己烷二酮类化合物具有强的和选择性的除草活性。
新的通式(I)的取代的苯甲酰基环己烷二酮类化合物可如下获得:在脱水剂存在下,任选地在一种或多种反应助剂存在下和任选地在稀释剂存在下,使式(II)的1,3-环己烷二酮或其衍生物与式(III)的取代的苯甲酸反应,
其中
R1和R2各如上所定义,
其中
A1、A2、R3、R4和R5各如上所定义。
原则上,通式(I)化合物也可以通过如下所示的那样来合成:
任选地在稀释剂例如二氯甲烷存在下,任选地在反应助剂例如三乙胺(和任选地还有氯化锌)存在下,使上述的式(II)的1,3-环己烷二酮或其衍生物与上述的式(III)的取代的苯甲酸的反应性衍生物、特别是其相应的酰氯、酸酐、酰基氰化物、酰基咪唑、酰基三唑、甲酯或乙酯反应:
(Y是例如CN、Cl、咪唑基、三唑基、甲氧基、乙氧基)。
在所概括的制备通式(I)化合物的反应中,除了所希望的在环己烷二酮上的C-苯甲酰化反应外,还存在O-苯甲酰化反应——参见下面的反应式(参见,Synthesis 1978,925-927;Tetrahedron Lett.37(1996),1007-1009,WO-A-91/05469)。然而,在该方法中形成的O-苯甲酰化化合物在本发明方法的反应条件下异构化成了相应的通式(I)的C-苯甲酰化化合物:
用例如1,3-环己烷二酮和3-氟-5-[(3-甲基-2-氧代咪唑烷-1-基)甲基]苯甲酸作为原料,在本发明方法中所述的反应的过程可以用下述反应式来说明:
式(II)提供了在制备通式(I)化合物的本发明方法中用作起始原料的环己烷二酮的一般定义。在式(II)中,R1和R2各自优选或特别具有在上文有关本发明式(I)化合物的描述中作为优选或特别优选对R1和R2业已提到的的含义。
通式(II)的原料是已知的和/或可以通过本身已知的方法制备。
式(III)提供了在制备通式(I)化合物的本发明方法中用作起始原料的取代的苯甲酸的一般定义。在式(III)中,A1、A2、R3、R4和R5各自优选或特别具有在上文有关本发明式(I)化合物的描述中作为优选或特别优选对A1、A2、R3、R4和R5业已提到的的含义。
通式(III)的原料是新的,然而,它们可以通过本身已知的方法制备(参见US-A-3 833 586、WO-A-94/22826、WO-A-95/34540)。因此,式(III)化合物同样形成了本发明的部分主题。
式(III)的取代的苯甲酸如下获得:在10-100℃的温度下,任选地在有机溶剂如1,4-二噁烷存在下,任选地在水解助剂存在下,使式(IV)的相应取代的苯甲酸酯与水反应(参见,制备实施例),
其中
A1、A2、R3、R4和R5各如上所定义,和
R代表烷基(特别是甲基或乙基)。
作为前体的通式(IV)的取代的苯甲酸酯是新的,然而,它们可以通过本身已知的方法制备(参见US-A-3 833 586、WO-A-94/22826、WO-A-95/34540)。因此,式(IV)化合物也形成了本发明的部分主题。
式(IV)的取代的苯甲酸酯如下获得:在10-120℃的温度下,在稀释剂如丙酮、乙腈或N,N-二甲基甲酰胺存在下,任选地在酸受体如碳酸钾或碳酸钠存在下,任选地在其它反应助剂如碘化钾或碘化钠存在下,使式(V)的相应的卤代烷基苯甲酸酯与式(VI)的1,3-二氮杂-2-氧代环烷烃反应(参见,制备实施例),
其中
A1、R、R3和R4各如上所定义,和
X代表卤素(特别是氟、氯或溴)或烷基磺酰氧基(特别是甲基磺酰氧基或乙基磺酰氧基),
其中
A2和R5各如上所定义。
一些式(VI)化合物是已知的(J.Amer.Chem.Soc.,78,5349,(1956),US 2 518 264,Experientia 13,183(1957),Chem.Pharm.Bull.1980,1810,J.Chem.Soc.Perkin Trans 1,1998,423,US5 972 431)并可以通过这些出版物中所述的方法制备。然而,一些式(VI)化合物是新的(也参见表5),并且它们形成了本发明的部分主题。
本发明的制备新的式(I)的取代的苯甲酰基环己烷二酮的方法使用脱水剂进行。这里,合适的脱水剂是适于与水结合的常规的化学品。
它们的例子有二环己基碳化二亚胺和羰基二咪唑。
特别合适的脱水剂是二环己基碳化二亚胺。
本发明的制备新的式(I)的取代的苯甲酰基环己烷二酮的方法任选地使用反应助剂进行。
它们的例子有氰化钠、氰化钾、丙酮合氰化氢、2-氰基-2-(三甲基甲硅烷氧基)丙烷、三甲基甲硅烷基氰化物和1,2,4-三唑。
特别适合的其它反应助剂是三甲基甲硅烷基氰化物。
本发明的制备新的式(I)的取代的苯甲酰基环己烷二酮的方法任选地使用其它反应助剂进行。合适的进行本发明方法的其它反应助剂一般是碱性有机氮化合物,例如,三甲胺、三乙胺、三丙胺、三丁胺、乙基二异丙基胺、N,N-二甲基环己基胺、二环己基胺、乙基二环己基胺、N,N-二甲基苯胺、N,N-二甲基苄基胺、吡啶、2-甲基-、3-甲基-、4-甲基-、2,4-二甲基-、2,6-二甲基-、3,4-二甲基-和3,5-二甲基-吡啶、5-乙基-2-甲基吡啶、4-二甲基氨基吡啶、N-甲基哌啶、1,4-二氮杂二环[2.2.2]辛烷(DABCO)、1,5-二氮杂二环[4.3.0]壬-5-烯(DBN)或1,8-二氮杂二环[5.4.0]十一-7-烯(DBU)。
进行本发明方法的合适的稀释剂特别是惰性有机溶剂。这些物质包括特别是脂肪族、脂环族或芳族的任选卤代的烃,诸如,例如汽油(轻石油)、苯、甲苯、二甲苯、氯苯、二氯苯、石油醚、己烷、环己烷、二氯甲烷、氯仿、四氯化碳或1,2-二氯乙烷;醚类,如乙醚、异丙醚、二噁烷、四氢呋喃、乙二醇二甲醚或乙二醇二乙醚;酮类,如丙酮、丁酮或甲基异丁基酮;腈类,如乙腈、丙腈或丁腈;酰胺类,如N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基-甲酰苯胺、N-甲基吡咯烷酮或六甲基磷酰三胺;酯类,如乙酸甲酯或乙酸乙酯;亚砜类,如二甲基亚砜。
进行本发明方法时,反应温度可以在较宽的范围内变化。通常,反应是在0℃至150℃,优选在10℃至120℃间的温度下进行。
本发明的方法通常是在常压下进行的。然而,本发明方法也可以在加压或减压下——通常是在0.1巴至10巴间的压力下进行。
进行本发明方法时,原料通常以大约等摩尔量使用。然而,也可以使用较大过量的反应组分之一。反应通常是在合适的稀释剂中在脱水剂存在下进行,并且反应混合物通常是在所需的温度下搅拌数小时。后处理是用常规方法进行(参见,制备实施例)。
本发明活性化合物可以用作脱叶剂、干燥剂、杀茎杆剂,和特别是用作除草剂。所谓的杂草,就其最广义而言,应理解为生长在不该生长的地方的所有植物。本发明的物质是作为灭生性除草剂或是选择性除草剂基本上取决于所用的量。本发明化合物可以与例如下列植物相关使用:
下列属的双子叶杂草:苘麻属、苋属、豚草属、Anoda、春黄菊属、Aphanes、滨藜属、雏菊属、鬼针草属、荠属、飞廉属、决明属、矢车菊属、藜属、蓟属、旋花属、曼陀罗属、山马蝗属、刺酸模属、糖芥属、大戟属、鼬瓣花属、牛膝菊属、猪殃殃属、木槿属、番薯属、地肤属、野芝麻属、独行草属、母草属、母菊属、薄荷属、山靛属、Mullugo、勿忘我属、罂粟属、牵牛属、车前属、蓼属、马齿苋属、毛莨属、萝卜属、蔊菜属、节节菜属、酸模属、猪毛菜属、千里光属、田菁属、黄花稔属、芥属、茄属、苦苣菜属、尖瓣花属、繁缕属、蒲公英属、遏蓝菜属、三叶草属、荨麻属、婆婆纳属、堇菜属、苍耳属。
下列属的双子叶作物:花生属、甜菜属、芸苔属、黄瓜属、南瓜属、向日葵属、胡萝卜属、大豆属、棉属、番薯属、莴苣属、亚麻属、番茄属、烟草属、菜豆属、豌豆属、茄属、巢菜属。
下列属的单子叶杂草:山羊草属、冰草属、翦股颖属、看麦娘属、Apera、燕麦属、臂形草属、雀麦属、栗草属、鸭跖草属、狗牙根属、莎草属、龙爪茅属、马唐属、稗属、荸荠属、蟋蟀草属、画眉草属、野黍属、羊茅属、飘拂草属、异蕊花属、白茅属、鸭嘴草属、千金子属、黑麦草属、雨久花属、黍属、雀稗属、
草属、梯牧草属、早熟禾属、筒轴茅属、慈姑属、莞草属、狗尾草属、高粱属。
下列属的单子叶作物:葱属、凤梨属、天门冬属、燕麦属、大麦属、稻属、黍属、蔗属、黑麦属、高粱属、黑小麦、小麦属、玉蜀黍属。
然而,本发明活性化合物的应用决不限于这些属,且也可以相同的方式延伸至其它植物。
取决于其浓度,本发明的活性化合物适合于灭生性防治杂草,例如工业地域和铁道线,以及有或无种植树林的道路和广场。同样,活性化合物可以用于防治多年生作物中的杂草,例如森林、装饰树林、果园、葡萄园、柑桔林、坚果园、蕉种植园、咖啡种植园、茶园、橡胶种植园、油棕榈种植园、可可种植园、软果林和啤酒花田、草场、体育场和牧场中的杂草且用于选择性地防治一年生作物中的杂草。
本发明式(I)化合物当施于土壤或用于植物地上部分时,具有强的除草活性和宽阔的活性谱;在某种程度上,它们还适合于以芽前和芽后二种方式选择性地防治单子叶和双子叶作物中的单子叶和双子叶杂草。
在某些浓度和施用率时,本发明的活性化合物也可以用于防治动物害虫和真菌性或细菌性植物疾病。任选地,它们也可以用作合成活性化合物的中间体或前体。
根据本发明,可以处理所有植物和植物部分。这里,植物应理解为所有植物和植物群体如希望的或不希望的野生植物或作物(包括天然存在的作物)。作物可以是通过常规种植和最优化方法或通过生物技术和基因工程方法或这些方法的结合可以获得的植物,包括转基因植物,也包括植物变种,无论它们是否可以被植物品种保护权利机构保护。植物部分应被理解为意指植物的所有地上和地下部分和器官例如芽、叶、花和根,可提及的例子是叶、针叶、茎、树干、花、果体、果实和种子以及还有根、块茎和根茎。植物部分也包括收割物,以及有生长力的和有生殖能力的繁殖材料例如秧苗、块茎、根茎、切割物和种子。
根据本发明用活性化合物对植物或植物部分的处理按照常规的处理方法例如浸蘸、喷雾、蒸发、雾化、撒播、刷涂和在繁殖材料的情况下特别是种子的情况下还可以通过单-或多层涂布直接地或通过作用于它们的环境、栖生地或储存地来进行。
活性化合物可以转化成常规的制剂,如溶液、乳剂、可湿性粉剂、悬浮剂、粉剂、粉尘剂、膏剂、可溶性粉剂、颗粒剂、悬乳剂、用活性化合物浸渍的天然或合成材料,以及包在聚合物中的微细胶囊。
这些制剂可以用已知的方式生产,例如,将活性化合物与扩充剂,即液体溶剂和/或与固体载体混合,并任选使用表面活性剂,即乳化剂和/或分散剂和/或起泡剂。
如果用水作扩充剂,也可以用有机溶剂作助溶剂。适合的液体溶剂主要有:芳族化合物,如二甲苯,甲苯或烷基萘,氯代芳族化合物或氯代脂肪烃,如氯代苯类、氯乙烯类或二氯甲烷,脂族烃,如环己烷或石蜡,例如石油馏份、矿物和植物油,醇类,如丁醇或乙二醇以及其醚和酯,酮类,如丙酮、甲乙酮、甲基异丁基酮或环己酮,强极性溶剂,如二甲基甲酰胺或二甲基亚砜,以及水。
适合的固体载体是:例如铵盐和磨碎的天然矿物质,如高岭土、粘土、滑石、白垩、石英、硅镁土、蒙脱石或硅藻土,和磨碎的合成矿物质,如高分散二氧化硅、矾土和硅酸盐,适合用于颗粒剂的固体载体有:例如压碎并分级的天然矿物质如方解石、大理石、浮石、海泡石和白云石,以及有机和无机粉的合成颗粒,和如下有机物的颗粒:锯木屑、椰壳、玉米穗轴和烟茎;适合的乳化剂和/或起泡剂是:例如非离子和阴离子乳化剂,如聚氧乙烯脂肪酸酯、聚氧乙烯脂肪醇醚,例如,烷芳基聚乙二醇醚,烷基磺酸盐,烷基硫酸盐,芳基磺酸盐以及白蛋白水解产物;适合的分散剂是:例如,木素亚硫酸废液和甲基纤维素。
制剂中可以使用粘合剂如羧甲基纤维素和粉状、颗粒或乳胶形式的天然和合成聚合物,如阿拉伯胶、聚乙烯醇和聚乙酸乙烯酯,以及天然磷脂,如脑磷脂和卵磷脂,和合成磷脂。其它可能的添加剂是矿物油和植物油。
也可以使用着色剂,如无机颜料,例如氧化铁、氧化钛和普鲁士蓝,和有机染料,如茜素染料、偶氮染料和金属酞菁染料,和微量营养元素如铁、锰、硼、铜、钴、钼和锌的盐。
制剂中通常含有按重量计0.1至95%的活性化合物,优选0.5至90%。
本发明活性化合物,其原样或以其制剂形式,也可以作为与已知除草剂和/或改善植物安全性的物质(“安全剂”)一起的混合物用于防治杂草,可以是终制剂或桶混物。也可以是与包含一种或多种已知除草剂和安全剂的除草剂的混合物。
混合物的可能的共组分是已知除草剂,例如,乙草胺、三氟羧草醚(钠盐)、苯草醚、甲草胺、禾草灭(钠盐)、莠灭净、amicarbazone、amidochlor、酰嘧黄隆、莎稗磷、磺草灵、莠去津、azafenidin、四唑嘧黄隆、BAS-662H、beflubutamid、草除灵、呋草黄、苄嘧黄隆(甲酯)、灭草松、benzfendizone、benzobicyclon、吡草酮、新燕灵(乙酯)、双丙氨酰磷、甲羧除草醚、双草醚、溴丁酰草胺、溴酚肟、溴苯腈、丁草胺、butafenacil(-allyl)、butroxydim、丁草敌、cafenstrole、caloxydim、双酰草胺、carfentrazone(-ethyl)、甲氧除草醚、草灭畏、杀草敏、氯嘧黄隆(乙酯)、草枯醚、绿黄隆、绿麦隆、cinidon(-ethyl)、环庚草醚、醚黄隆、clefoxydim、烯草酮、炔草酸、异噁草酮、氯甲酰草胺、二氯吡啶酸、clopyrasulfuron(-methyl)、cloransulam(-methyl)、cumyluron、氰草津、cybutryne、灭草特、环丙嘧磺隆、噻草酮、氰氟草酯、2,4-滴、2,4-滴丁酸、甜菜安、燕麦敌、麦草畏、精2,4-滴丙酸、禾草灵(甲酯)、diclosulam、乙酰甲草胺、野燕枯、吡氟草胺、diflufenzopyr、唑隆、哌草丹、二甲草胺、二甲丙乙净、二甲吩草胺、dimexyflam、氨氟灵、双苯酰草胺、敌草快、氟硫草定、敌草隆、杀草隆、epoprodan、茵达灭、戊草丹、乙丁烯氟灵、胺苯黄隆(甲酯)、乙呋草黄、ethoxyfen、ethoxysulfuron、etobenzanid、噁唑禾草灵乙酯、fentrazamide、麦草伏(异丙酯)、麦草伏(异丙酯-L)、麦草伏(甲酯)、啶嘧黄隆、florasulam、吡氟禾草灵(丁酯)、fluazolate、flucarbazone(sodium)、flufenacet、唑嘧磺草胺、氟烯草酸、丙炔氟草胺、flumipropyn、吡唑磺草胺、氟草隆、氟咯草隆、乙羧氟草醚(乙酯)、胺草唑、flupropacil、flurpyrsulfuron(-methyl、sodium)、芴丁酸、氟啶草酮、fluroxypyr(-butoxypropyl,-meptyl)、氟嘧醇、flurtamone、fluthiacet(-methyl)、fluthiamide、氟黄胺草醚、foramsulfuron、草铵磷(铵盐)、草甘磷(异丙铵盐)、halosafen、吡氟氯禾灵(乙氧基乙酯)、精吡氟氯禾灵(甲酯)、环嗪酮、咪草酯(甲酯)、imazamethapyr、imazamox、imazapic、灭草烟、灭草喹、咪草烟、咪唑黄隆、碘磺隆(甲酯,钠盐)、碘苯腈、异丙乐灵、异丙隆、异噁隆、异噁酰草胺、isoxachlortole、isoxaflutole、噁草醚、乳氟禾草灵、环草定、利谷隆、2甲4氯、2甲4氯丙酸、苯噻酰草胺、mesotrione、苯嗪草酮、吡唑草胺、甲基苯噻隆、吡喃隆、秀谷隆、(α-)异丙甲草胺、磺草唑胺、甲氧隆、嗪草酮、甲黄隆(甲酯)、草达灭、绿谷隆、萘丙胺、萘氧丙草胺、草不隆、烟嘧黄隆、哒草伏、坪草丹、安磺乐灵、oxadiargyl、噁草酮、oxasulfuron、oxaziclomefone、乙氧氟草醚、百草枯、壬酸、二甲戊灵、pendralin、pentoxazone、甜菜宁、picolinafen、哌草磷、丙草胺、氟嘧黄隆(甲酯)、profluazol、扑草净、毒草胺、敌稗、喔草酯、异丙草胺、procarbazone(-sodium)、戊炔草胺、苄草丹、氟磺隆、pyraflufen(-ethyl)、pyrazogyl、吡唑特、吡嘧黄隆(乙酯)、苄草唑、pyribenzoxim、稗草丹、哒草特、pyridatol、pyriftalid、pyriminobac(-methyl)、嘧草硫醚、二氯喹啉酸、喹草酸、灭藻醌、喹禾灵(乙酯)、喹禾灵(四氢糠酯)、砜嘧黄隆、稀禾定、西玛津、西草净、sulcitrione、甲磺草胺、嘧黄隆(甲酯)、草锍磷、甲嘧磺隆、牧草胺、特丁噻草隆、tepraloxydim、特丁津、特丁净、噻吩草胺、噻呋酰胺、噻唑烟酸、thidiazimin、噻黄隆(甲酯)、杀草丹、仲草丹、肟草酮、野燕畏、醚苯黄隆、苯黄隆(甲酯)、绿草定、灭草环、氟乐灵、floxysulfuron、氟胺黄隆和tritosulfuron。
也可以是与其它已知活性化合物如杀真菌剂、杀虫剂、杀螨剂、杀线虫剂、驱鸟剂、植物养料和土壤结构改良剂一起的混合物。
活性化合物可以以其本身、以其制剂或由之经进一步稀释而制备的使用形式使用,如直接可用溶液、悬浮液、乳液、粉剂、膏剂和颗粒剂。它们以常规方法使用,例如浇泼、喷雾、弥雾或撒施等等。
本发明活性化合物可以在植物萌发前或后施用。它们也可以在播种前掺入土壤中。
所用的活性化合物的量可以在相当宽的范围内变化。用量基本上取决于所需的效果。通常,使用量在每公顷土表面积用1克至10千克之间,优选每公顷5克至5千克。
本发明活性化合物的制备和使用可以参见下列实施例。
制备实施例:
实施例1
将4.4g(14.5mmol)的2,4-二氯-3-[(3-甲基-2-氧代咪唑烷-1-基)-甲基]苯甲酸先加入130ml的乙腈中,在室温(大约20℃)和搅拌下,依次与2.0g(17.4mmol)1,3-环己烷二酮和3.6g(17.4mmol)二环己基碳化二亚胺混合。将反应混合物搅拌30分钟,然后与4.4g(4.35mmol)三乙胺和2.6g(29mmol)丙酮合氰化氢混合。将混合物搅拌15小时,然后过滤,将滤液在水泵真空下浓缩,残留物与二氯甲烷/1N盐酸一起振摇,分离有机相,与100ml水混合,用碳酸钾调节pH值至11,水相与二氯甲烷一起振摇,分离,与100ml二氯甲烷混合,用1N盐酸酸化。有机相用水洗涤,然后用饱和氯化钠水溶液洗涤,用硫酸钠干燥,过滤。在减压下小心地从滤液中蒸去溶剂。
由此给出了2.4g(理论量的42%)的2-[2,4-二氯-3-[(3-甲基-2-氧代咪唑烷-1-基)-甲基]苯甲酰基]-1,3-环己烷二酮,为无定形产品。
类似于实施例1,并依照本发明制备方法的一般性描述,也可以制备例如列在下表1中的式(I)的化合物——或式(IA)、(IB)或(IC)的化合物。
表1:式(I)化合物实例
实施例编号 | A1 | A2 | (位置)R1(或R1+R2) | (位置)R2 | R3 | (位置)R4 | R5 | 通式物理数据 |
2 | CH2 | CH2CH2 | (5)CH3 | H | Cl | (2)Cl | CH3 | (IB)logP=2.55a) |
3 | CH2 | CH2CH2 | (5)CH3 | (5)CH3 | Cl | (2)Cl | CH3 | (IB)logP=2.79a) |
4 | CH2 | CH2CH2 | (4)CH3 | (4)CH3 | Cl | (2)Cl | CH3 | (IB)logP=2.89a) |
5 | CH2 | CH2CH2 | (5)C3H7-i | H | Cl | (2)Cl | CH3 | (IB)logP=3.22a) |
6 | CH2 | CH2CH2 | (5)C6H5 | H | Cl | (2)Cl | CH3 | (IB)logP=3.21a) |
7 | CH2 | CH2 | (5)CH3 | H | Cl | (2)Cl | CH3 | (IB)logP=2.43a) |
实施例编号 | A1 | A2 | (位置)R1(或R1+R2) | (位置)R2 | R3 | (位置)R4 | R5 | 通式物理数据 |
8 | CH2 | CH2 | (5)CH3 | (5)CH3 | Cl | (2)Cl | CH3 | (IB)logP=2.67a) |
9 | CH2 | CH2 | (4)CH3 | (4)CH3 | Cl | (2)Cl | CH3 | (IB)logP=2.75a) |
10 | CH2 | CH2 | (5)C3H7-i | H | Cl | (2)Cl | CH3 | (IB)logP=3.09a) |
11 | CH2 | CH2 | (5)C6H5 | H | Cl | (2)Cl | CH3 | (IB)logP=3.10a) |
12 | CH2 | CH2 | (5)CH3 | H | Cl | (2)Cl | C2H5 | (IB)logP=2.71a) |
13 | CH2 | CH2 | H | H | Cl | (2)Cl | C2H5 | (IB)logP=2.37a) |
14 | CH2 | CH2 | (5)CH3 | (5)CH3 | Cl | (2)Cl | C2H5 | (IB)logP=2.96a) |
15 | CH2 | CH2 | (4)CH3 | (4)CH3 | Cl | (2)Cl | C2H5 | (IB)logP=3.07a) |
16 | CH2 | CH2 | (5)C3H7-i | H | Cl | (2)Cl | C2H5 | (IB)logP=3.40a) |
17 | CH2 | CH2 | (5)C6H5 | H | Cl | (2)Cl | C2H5 | (IB)logP=3.38a) |
18 | CH2 | CH2CH2 | H | H | Cl | (2)OCH3 | CH3 | (IB)logP=2.05a) |
19 | CH2 | CH2 | H | H | Cl | (2)OCH3 | CH3 | (IB)logP=2.00a) |
20 | CH2 | CH2 | (5,5)(CH2)3 | - | Cl | (2)Cl | CH3 | (IB)logP=2.83a) |
21 | CH2 | CH2 | (5,5)(CH2)3 | - | Cl | (2)Cl | C2H5 | (IB)logP=3.15a) |
22 | CH2 | CH2 | H | H | SO2CH3 | (2)Cl | CH3 | (IB)logP=1.70a) |
实施例编号 | A1 | A2 | (位置)R1(或R1+R2) | (位置)R2 | R3 | (位置)R4 | R5 | 通式物理数据 |
23 | CH2 | CH2 | H | H | SO2CH3 | (2)Cl | C2H5 | (IB)logP=1.91a) |
24 | CH2 | CH2 | H | H | F | (2)Cl | CH3 | (IB)logP=1.96a) |
25 | CH2 | CH2 | H | H | CF3 | - | C2H5 | (IA)logP=2.68a) |
26 | CH2 | CH2 | (5)CH3 | H | SO2CH3 | (2)Cl | CH3 | (IB)m.p.147℃ |
27 | CH2 | CH2 | (5)CH3 | (5)CH3 | SO2CH3 | (2)Cl | CH3 | (IB)m.p.142℃ |
28 | CH2 | CH2 | (4)CH3 | (4)CH3 | SO2CH3 | (2)Cl | CH3 | (IB)m.p.140℃ |
29 | CH2 | CH2 | (5)C3H7-i | H | SO2CH3 | (2)Cl | CH3 | (IB)m.p.162℃ |
30 | CH2 | CH2 | (5)C6H5 | H | SO2CH3 | (2)Cl | CH3 | (IB)m.p.174℃ |
31 | CH2 | CH2 | (5,5)(CH2)3 | - | SO2CH3 | (2)Cl | CH3 | (IB)m.p.181℃ |
32 | CH2 | CH2 | (5)CH3 | H | SO2CH3 | (2)Cl | C2H5 | (IB)m.p.40℃ |
实施例编号 | A1 | A2 | (位置)R1(或R1+R2) | (位置)R2 | R3 | (位置)R4 | R5 | 通式物理数据 |
33 | CH2 | CH2 | (5)CH3 | (5)CH3 | SO2CH3 | (2)Cl | C2H5 | (IB)m.p.160℃ |
34 | CH2 | CH2 | (4)CH3 | (4)CH3 | SO2CH3 | (2)Cl | C2H5 | (IB)m.p.166℃ |
35 | CH2 | CH2 | (5)C3H7-i | H | SO2CH3 | (2)Cl | C2H5 | (IB)m.p.144℃ |
36 | CH2 | CH2 | (5)C6H5 | H | SO2CH3 | (2)Cl | C2H5 | (IB)m.p.182℃ |
37 | CH2 | CH2 | (5,5)(CH2)3 | - | SO2CH3 | (2)Cl | C2H5 | (IB)m.p.147℃ |
38 | CH2 | CH2CH2 | H | H | Cl | (2)OCH3 | C3H7-i | (IB) |
39 | CH2 | CH2 | H | H | Cl | (2)Cl | C3H7-i | (IB)m.p.:109℃ |
40 | CH2 | CH2 | H | H | SO2CH3 | (2)Cl | C3H7-i | (IB)m.p.:135℃ |
41 | CH2 | CH2CH2 | H | H | SO2CH3 | (2)Cl | CH3 | (IB)logP=1.73a) |
42 | CH2 | CH2 | (5)CH3 | H | Cl | (2)Cl | C3H7-i | (IB)m.p.:123℃ |
43 | CH2 | CH2 | (5)CH3 | (5)CH3 | Cl | (2)Cl | C3H7-i | (IB)m.p.:127℃ |
44 | CH2 | CH2CH2 | H | H | Cl | (2)Cl | C3H7-i | (IB)m.p.:151℃ |
实施例编号 | A1 | A2 | (位置)R1(或R1+R2) | (位置)R2 | R3 | (位置)R4 | R5 | 通式物理数据 |
45 | CH2 | CH2CH2 | H | H | SO2CH3 | (2)Cl | C3H7-i | (IB)m.p.:180℃ |
46 | CH2 | CH2 | H | H | Cl | (2)Cl | C3H7-n | (IB)logP=2.69a) |
47 | CH2 | CH2 | H | H | Cl | (2)Cl | C4H9-n | (IB)logP=3.08a) |
48 | CH2 | CH2 | H | H | Cl | (2)Cl | C4H9-i | (IB)logP=3.03a) |
49 | CH2 | CH2CH2 | H | H | CF3 | - | CH3 | (IA)logP=2.59a) |
50 | CH2 | CH2 | H | H | F | (2)Cl | C2H5 | (IB)logP=2.18a) |
51 | CH2 | CH2 | H | H | CF3 | - | CH3 | (IA)logP=2.41a) |
表1中给出的logP值是按照EEC Directive 79/831 Annex V.A8通过HPLC(高效液相色谱法)在反相柱(C18)上测定的,温度:43℃。
(a)用于在酸性范围内测定的流动相:0.1%磷酸水溶液,乙腈;从10%乙腈到90%乙腈的线性梯度——相应的试验结果在表1中用a)标记。
(b)用于在中性范围内测定的流动相:0.01M磷酸盐缓冲水溶液,乙腈;从10%乙腈到90%乙腈的线性梯度——相应的试验结果在表1中用b)标记。
校正是用具有已知logP值的非支化的烷-2-酮(具有3-16个碳原子)进行的(logP值是用两个连续的烷酮之间的线性内极化通过保留时间测定的)。
λmax值是借助在色谱信号的最大值内200nm到400nm的UV光谱测定的。
式(III)的起始原料:
实施例(III-1)
在室温(大约20℃)下,将29g(88mmol)的2,4-二氯-3-[(3-甲基-2-氧代咪唑烷-1-基)甲基]苯甲酸甲酯、3.6g(90mmol)的氢氧化钠、50ml水和100ml的1,4-二噁烷的混合物搅拌15小时,然后在水泵真空下浓缩。将残留物加入100ml水中,搅拌下用2N盐酸酸化。通过吸滤分离产生的结晶产物。
由此给出了25.1g(理论量的94%)的2,4-二氯-3-[(3-甲基-2-氧代咪唑烷-1-基)-甲基]苯甲酸,熔点221℃。
类似于实施例(III-1),也可以制备例如列在下表2中的式(III)的化合物:
表2:式(III)化合物实例
实施例编号 | (位置)A1 | A2 | (位置)R3 | (位置)R4 | R5 | 物理数据 |
III-79 | (2)- | CH2CH2 | (4)Cl | - | CH3 | |
III-80 | (2)- | CH2CH2 | (4)SO2CH3 | - | CH3 | |
III-81 | (3)- | CH2 | (2)Cl | (4)Cl | CH3 | |
III-82 | (3)- | CH2 | (2)Cl | (4)SO2CH3 | CH3 | |
III-83 | (3)- | CH2CH2 | (2)Cl | (4)Cl | CH3 | |
III-84 | (3)- | CH2CH2 | (2)Cl | (4)SO2CH3 | CH3 | |
III-85 | (3)- | CH2 | (2)OCH3 | (4)Cl | CH3 | |
III-86 | (3)- | CH2CH2 | (2)OCH3 | (4)Cl | CH3 | |
III-87 | (2)CH2CH2 | CH2 | (4)Cl | - | CH3 | |
III-88 | (2)CH2CH2 | CH2CH2 | (4)Cl | - | CH3 | |
III-89 | (2)CH2CH2 | CH2 | (4)CF3 | - | CH3 | |
III-90 | (2)CH2CH2 | CH2CH2 | (4)CF3 | - | CH3 | |
III-91 | (2)- | CH2 | (4)CF3 | - | CH3 | |
III-92 | (2)- | CH2CH2 | (4)CF3 | - | CH3 |
实施例编号 | (位置)A1 | A2 | (位置)R3 | (位置)R4 | R5 | 物理数据 |
III-93 | (2)CH2CH2 | CH2 | (2)Cl | (4)Cl | CH3 | |
III-94 | (2)CH2CH2 | CH2CH2 | (2)Cl | (4)Cl | CH3 | |
III-95 | (2)CH2CH2 | CH2 | (2)Cl | (4)SO2CH3 | CH3 | |
III-96 | (2)CH2CH2 | CH2CH2 | (2)Cl | (4)SO2CH3 | CH3 | |
III-97 | (3)CH2 | CH2 | (2)Cl | (4)Cl | C3H7-n | m.p.:195℃ |
III-98 | (3)CH2 | CH2 | (2)Cl | (4)Cl | C4H9-n | m.p.:163℃ |
III-99 | (3)CH2 | CH2 | (2)Cl | (4)Cl | C4H3-i | m.p.:195℃ |
式(IV)的前体:
实施例(IV-1)
将20g(0.20mol)的1-甲基-2-氧代咪唑烷、30g(0.10mol)的3-溴甲基-2,4-二氯苯甲酸甲酯、53g(0.50mol)碳酸钾和400ml的乙腈的混合物搅拌下加热回流48小时。加入1g碘化钠。然后将混合物再加热回流48小时,随后过滤。在减压下,小心地从滤液中蒸掉溶剂。残留物通过柱色谱纯化(硅胶,乙酸乙酯)。
由此给出了29.1g(理论量的92%)的2,4-二氯-3-[(3-甲基-2-氧代咪唑烷-1-基)-甲基]苯甲酸甲酯,熔点59℃。
类似于实施例(IV-1),也可以制备例如列在下表3中的式(IV)的化合物——以及还有例如上面列在表2中的苯甲酸的甲酯:
表3:式(IV)化合物实例
实施例编号 | (位置)A1 | A2 | R | (位置)R3 | (位置)R4 | R5 | 物理数据 |
IV-2 | (3)CH2 | CH2 | CH3 | (2)Cl | (4)Cl | C2H5 | logP=2.26a) |
IV-3 | (3)CH2 | CH2 | CH3 | (2)Cl | (4)SO2CH3 | C2H5 | logP=1.55a) |
IV-4 | (3)CH2 | CH2 | CH3 | (2)Cl | (4)SO2CH3 | CH3 | logP=1.55a) |
IV-5 | (3)CH2 | CH2 | CH3 | (2)OCH3 | (4)Cl | CH3 | logP=1.92a) |
IV-6 | (3)CH2 | CH2CH2 | CH3 | (2)Cl | (4)Cl | CH3 | logP=2.07a) |
IV-7 | (2)CH2 | CH2CH2 | CH3 | (4)CF3 | - | CH3 | |
IV-8 | (2)CH2 | CH2 | CH3 | (4)CF3 | - | CH3 | |
IV-9 | (3)CH2 | CH2CH2 | CH3 | (2)Cl | (4)F | CH3 | |
IV-10 | (3)CH2 | CH2CH2 | CH3 | (2)OCH3 | (4)Cl | CH3 | logP=2.03a) |
IV-11 | (2)CH2 | CH2 | CH3 | (4)CF3 | - | C2H5 | logP=2.62a) |
IV-12 | (3)CH2 | CH2 | CH3 | (2)Cl | (4)Cl | C3H7-n | logP=2.62 |
IV-13 | (3)CH2 | CH2 | CH3 | (2)Cl | (4)Cl | C3H7-i | logP=2.56 |
实施例编号 | (位置)A1 | A2 | R | (位置)R3 | (位置)R4 | R5 | 物理数据 |
IV-14 | (3)CH2 | CH2 | CH3 | (2)Cl | (4)SO2CH3 | C3H7-i | 1H-NMR(CD3CN)δ=1.07(d,6H);3.20(s,SO2CH3);3.92(s,OCH3); 4.91(CH2); 7.76(d,2H); 8.10(d,2H)ppm |
IV-15 | (3)CH2 | CH2 | CH3 | (2)Cl | (4)Cl | C4H9-n | logP=3.0 |
IV-16 | (3)CH2 | CH2 | CH3 | (2)Cl | (4)Cl | C4H9-i | logP=2.95 |
IV-17 | (3)CH2 | CH-CH2 | CH3 | (2)Cl | (4)SO2CH3 | CH3 | LC-MS:M+1=375/7 |
IV-18 | (3)CH2 | CH-CH2 | CH3 | (2)Cl | (4)Cl | C3H7-i | logP=2.65 |
式(V)的前体:
式(V)的卤代烷基苯甲酸酯可以按照已知的方式通过用例如N-溴代琥珀酰亚胺或N-氯代琥珀酰亚胺对相应的烷基苯甲酸酯卤化来制备。
式(V)的卤代烷基苯甲酸酯的实例列在下表4中:
表4:式(V)化合物实例
实施例编号 | (位置)A1X | (位置)R3 | (位置)R4 | R | 物理数据 |
V-1 | (3)CH2Br | (2)Cl | (4)Cl | CH3 | m.p.:61℃ |
V-2 | (3)CH2Br | (2)Cl | (4)SO2CH3 | CH3 | logP=2.33a) |
V-3 | (2)CH2Br | (4)NO2 | - | C2H5 | 1H-NMR(CDCl3,δ):4.97ppm(s,CH2) |
V-4 | (2)CH2Br | (4)CF3 | - | CH3 |
实施例编号 | (位置)A1X | (位置)R3 | (位置)R4 | R | 物理数据 |
V-5 | (2)CH2Br | (4)SO2CH3 | - | C2H5 | 1H-NMR(CDCl3,δ):4.96ppm(s,CH2) |
V-6 | (2)CH2Br | (4)SO2CH3 | - | CH3 | logP=1.87a) |
V-7 | (2)CH2Br | (4)CF3 | C2H5 | 1H-NMR(CDCl3,δ):4.96ppm(s,CH2) | |
V-8 | (2)CH2Br | (4)F | - | C2H5 | 1H-NMR(CDCl3,δ):4.93ppm(s,CH2) |
V-9 | (2)CH2Br | (4)Cl | - | C2H5 | 1H-NMR(CDCl3,δ):4.90ppm(s,CH2) |
V-10 | (2)CH2Br | (4)Br | - | C2H5 | 1H-NMR(CDCl3,δ):4.90ppm(s,CH2) |
V-11 | (2)CH2Br | (4)OCH3 | - | C2H5 | |
V-12 | (2)CH2Br | (4)I | - | CH3 |
实施例编号 | (位置)A1X | (位置)R3 | (位置)R4 | R | 物理数据 |
V-13 | (3)CH2Br | (2)OCH3 | (4)Cl | CH3 | 1H-NMR(DMSO-D6,δ):4.72ppm(s,CH2) |
V-14 | (3)CH2Br | (2)OCH3 | (4)SO2CH3 | CH3 | |
V-15 | (3)CH2Br | (2)OCH3 | (4)CF3 | CH3 | |
V-16 | (3)CH2Br | (2)OCH3 | (4)SCH3 | CH3 | |
V-17 | (3)CH2Br | (2)NO2 | (4)CF3 | CH3 | |
V-18 | (3)CH2Br | (2)NO2 | (4)SO2CH3 | CH3 | |
V-19 | (3)CH2Br | (2)NO2 | (4)CN | CH3 | |
V-20 | (2)CH2Br | (4)CN | - | CH3 | |
V-21 | (3)CH2Br | (2)CF3 | (4)SO2CH3 | CH3 | |
V-22 | (3)CH2Br | (2)CF3 | (4)CN | CH3 | |
V-23 | (3)CH2Br | (2)Cl | (4)F | CH3 | |
V-24 | (3)CH2Br | (2)F | (4)Cl | CH3 | |
V-25 | (3)CH2Br | (2)SO2CH3 | (4)Cl | CH3 |
实施例编号 | (位置)A1X | (位置)R3 | (位置)R4 | R | 物理数据 |
V-26 | (4)CH2Br | (2)Cl | - | CH3 | |
V-27 | (2)CH2Br | (4)Cl | (3)OCH3 | CH3 |
式(VI)的前体:
实施例(VI-1)
将75g(1.0mol)的N1-甲基乙烷-1,2-二胺在搅拌下滴加到214g(1.0mol)的碳酸二苯酯和1升甲苯的混合物中。然后将混合物加热回流煮沸60分钟,再在100℃/30毫巴下浓缩。残留物在110℃/1毫巴下蒸馏,馏出物(41.5%的1-甲基-2-氧代咪唑烷和58.5%苯酚)通过柱色谱纯化(硅胶,乙酸乙酯)。
由此给出了37.3g(理论量的37%)的1-甲基-2-氧代咪唑烷,熔点114℃。
类似于实施例(VI-1),也可以制备例如列在下表5中的式(VI)的化合物:
表5:式(VI)化合物实例
应用实施例
实施例A
芽前试验
溶剂: 5份重量丙酮
乳化剂: 1份重量的烷芳基聚乙二醇醚
制备适合的活性化合物制剂时,将1份重量的活性化合物与所述量的溶剂混合,将所述量的乳化剂加入,并用水将此乳油稀释至所需浓度。
将试验植物的种子播入通常的土壤中,约24小时后,土壤用活性化合物制剂浇水,在每单位面积上施用特定量的活性成分。选择喷雾液的浓度,使所需的活性化合物的特定量以1000升水/公顷的喷雾量施用。
三周后,将植物的损害程度与未处理对照的发育相比较,目测定出损害%。
数值的含义如下:
0%=无作用(与未处理相同)
100%=完全破坏
在此试验中,例如,制备实施例1、2、3、4、7、8、9、12、13、18和24的化合物对杂草显示出非常强的活性。
实施例B
芽后试验
溶剂: 5份重量丙酮
乳化剂: 1份重量的烷芳基聚乙二醇醚
制备适合的活性化合物制剂时,将1份重量的活性化合物与所述量的溶剂混合,将所述量的乳化剂加入,并用水将此乳油稀释至所需浓度。
向株高5-15厘米的试验植物按单位面积喷雾施用一定量的所需活性化合物制剂。选择喷雾液的浓度,使所需化合物的特定量以1,000升水/公顷的量施用。
三周后,将植物的损害程度与未处理对照相比较,定出损害%。
数值的含义如下:
0%=无作用(与未处理相同)
100%=完全破坏
在此试验中,制备实施例1、2、3、4、5、6、7、8、9、10、11、12、13、14、16、17、18和24的化合物对杂草显示出非常强的活性。
Claims (12)
1.通式(I)的取代的苯甲酰基环己烷二酮类化合物:
其中
A1代表单键或具有1-3个碳原子的亚烷基,
A2代表具有1-3个碳原子的亚烷基,
R1代表氢,代表苯基,或代表各自任选被卤素取代的、各自在烷基中具有1-4个碳原子的烷基、烷硫基或烷氧基羰基,
R2代表氢,或代表各自任选被卤素取代的、各自具有1-4个碳原子的烷基或烷硫基,或与R1一起代表具有最多4个碳原子的亚烷基,或——如果R1和R2连在同一个碳原子上——与R1还有R1和R2所连的碳原子一起代表羰基(C=O),
R3代表氢、硝基、氰基、羧基、氨甲酰基、硫代氨甲酰基、卤素,代表各自任选被卤素取代的、在烷基中各具有1-4个碳原子的烷基、烷氧基、烷硫基、烷基亚磺酰基、烷基磺酰基、烷基氨基、二烷基氨基、烷基磺酰基氨基或二烷基磺酰基氨基,或代表各自任选被卤素或C1-C4-烷基取代的各具有3-6个碳原子的环烷基氨基、环烷基磺酰基、环烷基磺酰基氨基或环烷基氨基磺酰基,
R4代表氢、硝基、氰基、羧基、氨甲酰基、硫代氨甲酰基、卤素,或代表各自任选被卤素取代的、在烷基中各具有1-4个碳原子的烷基、烷氧基、烷硫基、烷基亚磺酰基、烷基磺酰基、烷基氨基、二烷基氨基或二烷基氨基磺酰基,
R5代表氢,代表氨基,代表各自任选被氨基、氰基、卤素或C1-C4-烷氧基取代的、在烷基中各具有1-5个碳原子的烷基、烷氧基、烷基氨基、二烷基氨基、烷基磺酰基或烷基磺酰基氨基,代表各自任选被卤素取代的、各自具有最多5个碳原子的链烯基或炔基,代表各自任选被氰基、卤素或C1-C4-烷基取代的在环烷基中各具有3-6个碳原子和任选地在烷基中各自具有1-3个碳原子的环烷基或环烷基烷基,代表具有5或6个碳原子的环烯基,或代表各自任选被硝基、氰基、羧基、卤素、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基或C1-C4-卤代烷氧基取代的苯基、苯基-C1-C4-烷基、吡啶基或嘧啶基,
包括所有可能的式(I)化合物的互变异构形式和可能的式(I)化合物的盐和金属配合物,
排除化合物1-[2,6-二氯-3-[(2-羟基-6-氧代-环己烯-1-基)羰基]苄基]-3-甲基-四氢-2(1H)-嘧啶酮。
2.根据权利要求1的化合物,其特征在于:
A1代表单键,代表亚甲基、乙烷-1,1-二基、乙烷-1,2-二基、丙烷-1,1-二基、丙烷-1,2-二基或丙烷-1,3-二基,
A2代表亚甲基、乙烷-1,1-二基、乙烷-1,2-二基、丙烷-1,1-二基、丙烷-1,2-二基或丙烷-1,3-二基,
R1代表氢,代表苯基,或代表各自任选被氟和/或氯取代的甲基、乙基、正-或异-丙基、甲硫基、乙硫基、正-或异丙硫基、甲氧基羰基、乙氧基羰基、正-或异丙氧基羰基,
R2代表氢,或代表各自任选被氟和/或氯取代的甲基、乙基、正或异-丙基、甲硫基、乙硫基、正-或异丙硫基,或与R1一起代表亚甲基、乙烷-1,1-二基、乙烷-1,2-二基、丙烷-1,1-二基、丙烷-1,2-二基或丙烷-1,3-二基,或——如果R1和R2连在同一个碳原子上——与R1还有R1和R2所连的碳原子一起代表羰基(C=O),
R3代表氢、硝基、氰基、羧基、氨甲酰基、硫代氨甲酰基、氟、氯、溴、碘,代表各自任选被氟和/或氯取代的甲基、乙基、正或异-丙基、甲氧基、乙氧基、正或异-丙氧基、甲硫基、乙硫基、正-或异丙硫基、甲基亚磺酰基、乙基亚磺酰基、正或异-丙基亚磺酰基、甲基磺酰基、乙基磺酰基、正或异-丙基磺酰基,代表甲基氨基、乙基氨基、正或异-丙基氨基、二甲基氨基、二乙基氨基、甲基磺酰基氨基、乙基磺酰基氨基、正或异-丙基磺酰基氨基、二甲基氨基磺酰基或二乙基氨基磺酰基,或代表各自任选被氟、氯或甲基取代的环丙基氨基、环丁基氨基、环戊基氨基、环己基氨基、环丙基磺酰基、环丁基磺酰基、环戊基磺酰基、环己基磺酰基、环丙基磺酰基氨基、环丁基磺酰基氨基、环戊基磺酰基氨基、环己基磺酰基氨基、环丙基氨基磺酰基、环丁基氨基磺酰基、环戊基氨基磺酰基或环己基氨基磺酰基,
R4代表氢、硝基、氰基、羧基、氨甲酰基、硫代氨甲酰基、氟、氯、溴、碘,或代表各自任选被氟和/或氯取代的甲基、乙基、正或异-丙基、甲氧基、乙氧基、正或异-丙氧基、甲硫基、乙硫基、正-或异丙硫基、甲基亚磺酰基、乙基亚磺酰基、正或异-丙基亚磺酰基、甲基磺酰基、乙基磺酰基、正或异-丙基磺酰基,代表甲基氨基、乙基氨基、正或异-丙基氨基、二甲基氨基、二乙基氨基、二甲基氨基磺酰基或二乙基氨基磺酰基,
R5代表氢,代表氨基,代表各自任选被氨基、氰基、氟和/或氯、甲氧基或乙氧基取代的甲基、乙基、正或异-丙基、正-、异-、仲-或叔丁基、甲氧基、乙氧基、正或异-丙氧基、正-、异-、仲-或叔丁氧基、甲基氨基、乙基氨基、正或异-丙基氨基、正-、异-、仲-或叔丁基氨基、二甲基氨基、二乙基氨基、二丙基氨基、甲基磺酰基、乙基磺酰基或甲基磺酰基氨基,代表各自任选被氟、氯和/或溴取代的丙烯基、丁烯基、丙炔基或丁炔基,代表各自任选被氰基、氟、氯、甲基或乙基取代的环丙基、环丁基、环戊基、环己基、环丙基甲基、环丁基甲基、环戊基甲基或环己基甲基,代表环己烯基,或代表各自任选被氟、氯、溴、甲基、三氟甲基、甲氧基、二氟甲氧基或三氟甲氧基取代的苯基、苄基、吡啶基或嘧啶基。
3.根据权利要求1的化合物,其特征在于:
A1代表单键,代表亚甲基、乙烷-1,2-二基或丙烷-1,3-二基,
A2代表亚甲基、乙烷-1,2-二基或丙烷-1,3-二基,
R1代表氢、苯基、甲基、乙基、正-或异-丙基、甲硫基、乙硫基、甲氧基羰基或乙氧基羰基,
R2代表氢、甲基、乙基、甲硫基、乙硫基,或与R1一起代表亚甲基、乙烷-1,2-二基或丙烷-1,3-二基,或——如果R1和R2连在同一个碳原子上——与R1还有R1和R2所连的碳原子一起代表羰基(C=O),
R3代表氢、硝基、氰基、氟、氯、溴、碘,代表各自任选被氟和/或氯取代的甲基、乙基、甲氧基、乙氧基、甲硫基、乙硫基、甲基亚磺酰基、乙基亚磺酰基、甲基磺酰基、乙基磺酰基,代表甲基氨基、乙基氨基、二甲基氨基或二甲基氨基磺酰基,
R4代表氢、硝基、氰基、氟、氯、溴、碘,或代表各自任选被氟和/或氯取代的甲基、乙基、甲氧基、乙氧基、甲硫基、乙硫基、甲基亚磺酰基、乙基亚磺酰基、甲基磺酰基、乙基磺酰基,代表甲基氨基、乙基氨基、二甲基氨基或二甲基氨基磺酰基,
R5代表氢、甲基、乙基、正或异-丙基、正-、异-、仲-或叔丁基、丙烯基、丙炔基、环丙基、环戊基、环己基、环丙基甲基、环戊基甲基、环己基甲基、苯基或苄基。
4.根据权利要求1的化合物,其特征在于:
A1代表亚甲基或乙烷-1,2-二基,
A2代表亚甲基或乙烷-1,2-二基,
R1代表氢、苯基、甲基、乙基、正-或异-丙基、甲硫基或乙硫基,
R2代表氢、甲基、乙基、甲硫基,或与R1一起优选代表乙烷-1,2-二基或丙烷-1,3-二基,或——如果R1和R2连在同一个碳原子上——与R1还有R1和R2所连的碳原子一起代表羰基(C=O),
R3代表氢、硝基、氰基、氟、氯、溴、甲基、二氟甲基、三氟甲基、二氯甲基、三氯甲基、氯二氟甲基、乙基、甲氧基、二氟甲氧基、三氟甲氧基、氯二氟甲氧基、乙氧基、甲硫基、二氟甲硫基、三氟甲硫基、氯二氟甲硫基、乙硫基、甲基亚磺酰基、三氟甲基亚磺酰基、乙基亚磺酰基、甲基磺酰基、三氟甲基磺酰基、乙基磺酰基、二甲基氨基或二甲基氨基磺酰基,
R4代表氢、硝基、氰基、氟、氯、溴、甲基、二氟甲基、三氟甲基、二氯甲基、三氯甲基、氯二氟甲基、乙基、甲氧基、二氟甲氧基、三氟甲氧基、氯二氟甲氧基、乙氧基、甲硫基、二氟甲硫基、三氟甲硫基、氯二氟甲硫基、乙硫基、甲基亚磺酰基、三氟甲基亚磺酰基、乙基亚磺酰基、甲基磺酰基、三氟甲基磺酰基、乙基磺酰基、二甲基氨基或二甲基氨基磺酰基,
R5代表氢、甲基、乙基、正或异-丙基、正-、异-、仲-或叔丁基、环丙基、环戊基或环己基。
5.根据权利要求1-4任一项的化合物,其特征在于它们作为钠盐、钾盐、镁盐、钙盐、铵盐、C1-C4-烷基铵盐、二-(C1-C4-烷基)-铵盐、三-(C1-C4-烷基)-铵盐、四-(C1-C4-烷基)-铵盐、三-(C1-C4-烷基)-锍盐、C5-或C6-环烷基-铵盐或二-(C1-C2-烷基)-苄基铵盐或作为与金属的配位化合物存在。
6.根据权利要求4的化合物,其以下列结构式为特征:
8.式(III)的化合物,
其中
A1、A2、R3、R4和R5各如权利要求1-4任一项中所定义。
9.式(IV)的化合物,
其中
A1、A2、R3、R4和R5各如权利要求1-4任一项中所定义。
10.权利要求1-4任一项中的至少一种化合物防治不想要的植物的应用。
11.防治不想要的植物的方法,其特征在于,使权利要求1-4任一项中的至少一种化合物作用于不想要的植物和/或其栖生地。
12.除草组合物,其特征在于,它们包含权利要求1-4任一项中的至少一种化合物和常规的扩充剂和/或表面活性剂。
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DE19962923A DE19962923A1 (de) | 1999-12-24 | 1999-12-24 | Substituierte Benzoylcyclohexandione |
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EP (1) | EP1244634B1 (zh) |
JP (1) | JP2003527351A (zh) |
KR (1) | KR20020065903A (zh) |
CN (1) | CN1630643A (zh) |
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AT (1) | ATE261943T1 (zh) |
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BR (1) | BR0017044A (zh) |
CA (1) | CA2406962A1 (zh) |
CO (1) | CO5231155A1 (zh) |
DE (2) | DE19962923A1 (zh) |
ES (1) | ES2214344T3 (zh) |
MX (1) | MXPA02006244A (zh) |
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CN102464630A (zh) * | 2010-11-19 | 2012-05-23 | 中国中化股份有限公司 | 含氮杂环取代的苯甲酰基类化合物及其应用 |
CN105473572A (zh) * | 2013-08-20 | 2016-04-06 | 先正达有限公司 | 除草化合物 |
CN105766944A (zh) * | 2014-12-22 | 2016-07-20 | 沈阳中化农药化工研发有限公司 | 一种除草剂及其应用 |
CN117247363A (zh) * | 2023-11-17 | 2023-12-19 | 山东滨农科技有限公司 | 恶二唑酮类化合物、除草组合物及其用途 |
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CN107353238B (zh) * | 2017-08-17 | 2019-09-03 | 青岛清原化合物有限公司 | 取代的苯甲酰基环己二酮类化合物或其互变异构体、盐、制备方法、除草组合物及应用 |
CN109535106B (zh) * | 2018-12-28 | 2020-12-29 | 安徽工大化工科技有限公司 | 一种呋喃磺草酮的制备方法 |
CN109526965A (zh) * | 2018-12-28 | 2019-03-29 | 安徽工大化工科技有限公司 | 一种除草缓蚀颗粒剂及其制备方法 |
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- 1999-12-24 DE DE19962923A patent/DE19962923A1/de not_active Withdrawn
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- 2000-12-12 JP JP2001549366A patent/JP2003527351A/ja active Pending
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- 2000-12-12 DE DE50005743T patent/DE50005743D1/de not_active Expired - Fee Related
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- 2000-12-12 EP EP00991172A patent/EP1244634B1/de not_active Expired - Lifetime
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- 2000-12-12 CN CNA008189897A patent/CN1630643A/zh not_active Withdrawn
- 2000-12-12 US US10/168,420 patent/US6825183B2/en not_active Expired - Fee Related
- 2000-12-12 PL PL00355443A patent/PL355443A1/xx not_active Application Discontinuation
- 2000-12-12 RU RU2002120460/04A patent/RU2002120460A/ru unknown
- 2000-12-12 ES ES00991172T patent/ES2214344T3/es not_active Expired - Lifetime
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- 2000-12-12 AT AT00991172T patent/ATE261943T1/de not_active IP Right Cessation
- 2000-12-12 BR BR0017044-5A patent/BR0017044A/pt not_active Application Discontinuation
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Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
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CN102464630A (zh) * | 2010-11-19 | 2012-05-23 | 中国中化股份有限公司 | 含氮杂环取代的苯甲酰基类化合物及其应用 |
WO2012065573A1 (zh) * | 2010-11-19 | 2012-05-24 | 中国中化股份有限公司 | 含氮杂环取代的苯甲酰基类化合物及其用途 |
CN102464630B (zh) * | 2010-11-19 | 2015-05-13 | 中国中化股份有限公司 | 含氮杂环取代的苯甲酰基类化合物及其应用 |
CN105473572A (zh) * | 2013-08-20 | 2016-04-06 | 先正达有限公司 | 除草化合物 |
CN105766944A (zh) * | 2014-12-22 | 2016-07-20 | 沈阳中化农药化工研发有限公司 | 一种除草剂及其应用 |
CN105766944B (zh) * | 2014-12-22 | 2018-12-14 | 沈阳中化农药化工研发有限公司 | 一种除草剂及其应用 |
CN117247363A (zh) * | 2023-11-17 | 2023-12-19 | 山东滨农科技有限公司 | 恶二唑酮类化合物、除草组合物及其用途 |
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ATE261943T1 (de) | 2004-04-15 |
PL355443A1 (en) | 2004-04-19 |
US7244692B2 (en) | 2007-07-17 |
US20030119674A1 (en) | 2003-06-26 |
US6825183B2 (en) | 2004-11-30 |
CA2406962A1 (en) | 2002-06-21 |
DE50005743D1 (de) | 2004-04-22 |
CO5231155A1 (es) | 2002-12-27 |
US20050054534A1 (en) | 2005-03-10 |
MXPA02006244A (es) | 2003-01-28 |
RU2002120460A (ru) | 2004-01-10 |
EP1244634B1 (de) | 2004-03-17 |
WO2001047894A1 (de) | 2001-07-05 |
BR0017044A (pt) | 2003-01-07 |
AR027067A1 (es) | 2003-03-12 |
DE19962923A1 (de) | 2001-07-05 |
KR20020065903A (ko) | 2002-08-14 |
EP1244634A1 (de) | 2002-10-02 |
ES2214344T3 (es) | 2004-09-16 |
AU3157601A (en) | 2001-07-09 |
JP2003527351A (ja) | 2003-09-16 |
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