CN1301257A - 取代的1,3-二氮杂-2-(硫)氧化环烷烃类化合物 - Google Patents
取代的1,3-二氮杂-2-(硫)氧化环烷烃类化合物 Download PDFInfo
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- CN1301257A CN1301257A CN99806393A CN99806393A CN1301257A CN 1301257 A CN1301257 A CN 1301257A CN 99806393 A CN99806393 A CN 99806393A CN 99806393 A CN99806393 A CN 99806393A CN 1301257 A CN1301257 A CN 1301257A
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- fluorine
- alkyl
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- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 45
- 239000005864 Sulphur Chemical group 0.000 claims abstract description 45
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000001301 oxygen Substances 0.000 claims abstract description 25
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 25
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 20
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 19
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 11
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 9
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 7
- 125000002950 monocyclic group Chemical group 0.000 claims abstract description 3
- -1 hydro carbons compound Chemical class 0.000 claims description 283
- 239000000460 chlorine Substances 0.000 claims description 117
- 229910052801 chlorine Inorganic materials 0.000 claims description 117
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 115
- 239000011737 fluorine Substances 0.000 claims description 106
- 229910052731 fluorine Inorganic materials 0.000 claims description 106
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 72
- 239000001257 hydrogen Substances 0.000 claims description 62
- 229910052739 hydrogen Inorganic materials 0.000 claims description 62
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 51
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 45
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 44
- 229910052794 bromium Inorganic materials 0.000 claims description 44
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 44
- 150000002431 hydrogen Chemical class 0.000 claims description 41
- 229910052799 carbon Inorganic materials 0.000 claims description 29
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 28
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 22
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 22
- 238000006467 substitution reaction Methods 0.000 claims description 22
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 20
- 229930195733 hydrocarbon Natural products 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 19
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 12
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 10
- 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 10
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 10
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 9
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
- 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 claims description 8
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 8
- 125000000062 cyclohexylmethoxy group Chemical group [H]C([H])(O*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 8
- 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 8
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 8
- 239000003085 diluting agent Substances 0.000 claims description 8
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 8
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 8
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 8
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical compound CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 claims description 8
- 125000005920 sec-butoxy group Chemical group 0.000 claims description 8
- 230000002363 herbicidal effect Effects 0.000 claims description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
- 125000003368 amide group Chemical group 0.000 claims description 6
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 claims description 6
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 6
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 6
- 239000002671 adjuvant Substances 0.000 claims description 5
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
- 125000006325 2-propenyl amino group Chemical group [H]C([H])=C([H])C([H])([H])N([H])* 0.000 claims description 4
- 229940099451 3-iodo-2-propynylbutylcarbamate Drugs 0.000 claims description 4
- WYVVKGNFXHOCQV-UHFFFAOYSA-N 3-iodoprop-2-yn-1-yl butylcarbamate Chemical compound CCCCNC(=O)OCC#CI WYVVKGNFXHOCQV-UHFFFAOYSA-N 0.000 claims description 4
- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 claims description 4
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 4
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 4
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 claims description 4
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 4
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 4
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 150000002366 halogen compounds Chemical class 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
- 229960004194 lidocaine Drugs 0.000 claims description 4
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 4
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 4
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 4
- 125000002971 oxazolyl group Chemical group 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 4
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims description 4
- 150000003217 pyrazoles Chemical class 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000006318 tert-butyl amino group Chemical group [H]N(*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000001425 triazolyl group Chemical group 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 4
- MUOGSAVBYRDONO-UHFFFAOYSA-N 2-(furan-2-ylmethoxy)oxane Chemical compound C=1C=COC=1COC1CCCCO1 MUOGSAVBYRDONO-UHFFFAOYSA-N 0.000 claims description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 125000006323 alkenyl amino group Chemical group 0.000 claims description 2
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims description 2
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 2
- 125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims description 2
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- 125000006319 alkynyl amino group Chemical group 0.000 claims description 2
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- 238000007336 electrophilic substitution reaction Methods 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 claims description 2
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- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 51
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- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 54
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- 238000002360 preparation method Methods 0.000 description 12
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- WQKGAJDYBZOFSR-UHFFFAOYSA-N potassium;propan-2-olate Chemical compound [K+].CC(C)[O-] WQKGAJDYBZOFSR-UHFFFAOYSA-N 0.000 description 1
- AAEVYOVXGOFMJO-UHFFFAOYSA-N prometryn Chemical compound CSC1=NC(NC(C)C)=NC(NC(C)C)=N1 AAEVYOVXGOFMJO-UHFFFAOYSA-N 0.000 description 1
- MFOUDYKPLGXPGO-UHFFFAOYSA-N propachlor Chemical compound ClCC(=O)N(C(C)C)C1=CC=CC=C1 MFOUDYKPLGXPGO-UHFFFAOYSA-N 0.000 description 1
- OYJMHAFVOZPIOY-UHFFFAOYSA-N propan-2-yl 2-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]benzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1 OYJMHAFVOZPIOY-UHFFFAOYSA-N 0.000 description 1
- LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- PHNUZKMIPFFYSO-UHFFFAOYSA-N propyzamide Chemical compound C#CC(C)(C)NC(=O)C1=CC(Cl)=CC(Cl)=C1 PHNUZKMIPFFYSO-UHFFFAOYSA-N 0.000 description 1
- NQLVQOSNDJXLKG-UHFFFAOYSA-N prosulfocarb Chemical compound CCCN(CCC)C(=O)SCC1=CC=CC=C1 NQLVQOSNDJXLKG-UHFFFAOYSA-N 0.000 description 1
- 229960003351 prussian blue Drugs 0.000 description 1
- 239000013225 prussian blue Substances 0.000 description 1
- YXIIPOGUBVYZIW-UHFFFAOYSA-N pyraflufen Chemical compound ClC1=C(OC(F)F)N(C)N=C1C1=CC(OCC(O)=O)=C(Cl)C=C1F YXIIPOGUBVYZIW-UHFFFAOYSA-N 0.000 description 1
- ASRAWSBMDXVNLX-UHFFFAOYSA-N pyrazolynate Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OS(=O)(=O)C1=CC=C(C)C=C1 ASRAWSBMDXVNLX-UHFFFAOYSA-N 0.000 description 1
- FKERUJTUOYLBKB-UHFFFAOYSA-N pyrazoxyfen Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OCC(=O)C1=CC=CC=C1 FKERUJTUOYLBKB-UHFFFAOYSA-N 0.000 description 1
- VTRWMTJQBQJKQH-UHFFFAOYSA-N pyributicarb Chemical compound COC1=CC=CC(N(C)C(=S)OC=2C=C(C=CC=2)C(C)(C)C)=N1 VTRWMTJQBQJKQH-UHFFFAOYSA-N 0.000 description 1
- DEIKMOQTJBGGAX-DJKKODMXSA-N pyriminobac Chemical compound CO\N=C(/C)C1=CC=CC(OC=2N=C(OC)C=C(OC)N=2)=C1C(O)=O DEIKMOQTJBGGAX-DJKKODMXSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- ALZOLUNSQWINIR-UHFFFAOYSA-N quinmerac Chemical compound OC(=O)C1=C(Cl)C=CC2=CC(C)=CN=C21 ALZOLUNSQWINIR-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- MGLWZSOBALDPEK-UHFFFAOYSA-N simetryn Chemical compound CCNC1=NC(NCC)=NC(SC)=N1 MGLWZSOBALDPEK-UHFFFAOYSA-N 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- SZXAJDQTPWYNBN-NWBUNABESA-M sodium;4-methoxycarbonyl-5,5-dimethyl-3-oxo-2-[(e)-n-prop-2-enoxy-c-propylcarbonimidoyl]cyclohexen-1-olate Chemical compound [Na+].C=CCO\N=C(/CCC)C1=C([O-])CC(C)(C)C(C(=O)OC)C1=O SZXAJDQTPWYNBN-NWBUNABESA-M 0.000 description 1
- 239000003516 soil conditioner Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- SSGGNFYQMRDXFH-UHFFFAOYSA-N sulfanylurea Chemical compound NC(=O)NS SSGGNFYQMRDXFH-UHFFFAOYSA-N 0.000 description 1
- OORLZFUTLGXMEF-UHFFFAOYSA-N sulfentrazone Chemical compound O=C1N(C(F)F)C(C)=NN1C1=CC(NS(C)(=O)=O)=C(Cl)C=C1Cl OORLZFUTLGXMEF-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- RJKCKKDSSSRYCB-UHFFFAOYSA-N tebutam Chemical compound CC(C)(C)C(=O)N(C(C)C)CC1=CC=CC=C1 RJKCKKDSSSRYCB-UHFFFAOYSA-N 0.000 description 1
- IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- AHTPATJNIAFOLR-UHFFFAOYSA-N thifensulfuron-methyl Chemical group S1C=CC(S(=O)(=O)NC(=O)NC=2N=C(OC)N=C(C)N=2)=C1C(=O)OC AHTPATJNIAFOLR-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- DQFPEYARZIQXRM-LTGZKZEYSA-N tralkoxydim Chemical compound C1C(=O)C(C(/CC)=N/OCC)=C(O)CC1C1=C(C)C=C(C)C=C1C DQFPEYARZIQXRM-LTGZKZEYSA-N 0.000 description 1
- XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 description 1
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
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- 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
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- 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
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- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/20—N-Aryl derivatives thereof
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- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
-
- 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
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- 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
- C07D233/36—One oxygen atom with hydrocarbon radicals, substituted by nitrogen atoms, attached to ring nitrogen atoms
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- 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
- C07D233/42—Sulfur atoms
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- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plural Heterocyclic Compounds (AREA)
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Abstract
本发明涉及新的式(I)的取代的1,3-二氮杂-2-(硫)氧代环烷烃类化合物,其中n为1、2或3,Q为氧或硫,R1代表烷基、烷氧基、烷基氨基、二烷基氨基、链烯基、炔基、环烷基或环烷基烷基,其中这些基团中的每一个都可能是被取代的,以及R2代表单环或双环状的芳族基团,该基团可能是被取代的和可能是与杂环稠合的。本发明还涉及这些化合物的制备方法及其作为除草剂的用途。
Description
本发明涉及新的式(Ⅰ)的取代的1,3-二氮杂-2-(硫)氧代环烷烃类化合物,它们的制备方法和它们作为除草剂的用途。
从文献中已经知道有一些取代的1,3-二氮杂-2-(硫)氧代环烷烃类化合物(参见J.Chem.Eng.Data 13(1968),582-585-引述在化学文摘(Chem.Abstracts)69:106613中)。但是,迄今为止没有公开这些化合物的生物学性质。
现已发现了新的通式(Ⅰ)的取代的1,3-二氮杂-2-(硫)氧代环烷烃类化合物,其中n为1、2或3,Q为氧或硫,R1代表氢、甲酰基,或代表各任选被取代的烷基、烷氧基、烷基氨基、二烷基氨基、链烯基、炔基、环烷基或环烷基烷基,以及R2代表任选被取代的单环或双环状的芳族基团,该基团任选地与杂环稠合。
在所述定义中,烃链如烷基-也包括与杂原子结合的情况如在烷氧基中-在每种情况下是直链或支链的。n优选为1、2或3;Q优选为氧或硫;R1优选代表氢、甲酰基或代表各在烷基中具有1-6个碳原子的并且各任选被氰基、卤素、C1-C4烷氧基、C1-C4烷基羰基、C1-C4烷氧基羰基或吗啉基取代的烷基、烷氧基、烷基氨基、二烷基氨基,或代表各具有2-6个碳原子的并且各任选被氰基、卤素或C1-C4烷氧基羰基取代的链烯基或炔基,或代表各在环烷基中具有3-6个碳原子的和如果适当的话在烷基中具有1-4个碳原子的并且各任选被氰基、卤素或C1-C4烷基取代的环烷基或环烷基烷基;以及R2优选代表如下定义的芳基其中R3 代表氢、硝基、氨基、氰基、甲酰氨基、卤素,或代表烷基、烷氧基、烷基羰基氨基、烷氧基羰基氨基、烷基氨基羰基氨基,这些基团各在烷基部分具有1-6个碳原子并且各任选被氰基、卤素或C1-C4烷氧基取代,或代表环烷基羰基氨基,该基团在环烷基部分具有3-6个碳原子并且该基团任选被氰基、卤素、C1-C4烷基或C1-C4卤代烷基取代,或代表苯基羰基氨基,该基团任选被氰基、硝基、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;R4 代表氢、硝基、氰基、氟、氯或溴;R5 代表硝基、氰基、羧基、氨基甲酰基、硫代氨基甲酰基、羟基、氟、氯、溴,或代表烷基、烷氧基、烷基羰基或烷氧基羰基,这些基团各具有最多4个碳原子并且各任选被氟和/或氯取代;R6 代表下式基团:-A1-A2-A3其中A1 代表单键,或代表氧、硫、-SO-、-SO2-、-CO-或基团-N-A4-,其中A4代表氢、羟基、C1-C4烷基、C3-C4链烯基、C3-C4炔基、C1-C4烷氧基、苯基、C1-C4烷基羰基、苯基羰基、C1-C4烷基磺酰基或苯基磺酰基,A1 还代表C1-C6链烷二基、C2-C6链烯二基、C2-C6氮杂链烯二基、C2-C6炔二基、C3-C6环烷二基、C3-C6环烯二基或亚苯基,这些基团各任选被氟、氯或溴取代,A2 代表单键,或代表氧、硫、-SO-、-SO2-、-CO-或基团-N-A4-,其中A4代表氢、羟基、C1-C4烷基、C1-C4烷氧基、苯基、C1-C4烷基磺酰基或苯基磺酰基,A2 还代表C1-C6链烷二基、C2-C6链烯二基、C2-C6氮杂链烯二基、C2-C6炔二基、C3-C6环烷二基、C3-C6环烯二基或亚苯基,这些基团各任选被氟、氯或溴取代,A3 代表氢、羟基、巯基、氨基、氰基、异氰基、氰硫基、硝基、羧基、氨基甲酰基、硫代氨基甲酰基、磺基、氯磺基、氟、氯、溴,或代表烷基、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、烷氧基羰基或二烷氧基(硫代)磷酰基,这些基团各在烷基中有1-6个碳原子并且各任选被氟、氯或C1-C4烷氧基取代,或代表链烯基、链烯基氧基、链烯基氨基、亚烷基氨基、链烯基氧基羰基、炔基、炔氧基、炔基氨基或炔氧基羰基,这些基团各在链烯基、亚烷基或炔基中具有2-6个碳原子并且各任选被氟或氯取代,或代表环烷基、环烷基氧基、环烷基烷基、环烷基烷氧基、亚环烷基氨基、环烷氧基羰基或环烷基烷氧基羰基,这些基团各在环烷基部分具有3-6个碳原子和如果适当在烷基部分具有1-4个碳原子并且各任选被氟、氯、氰基、羧基、C1-C4烷基和/或C1-C4烷氧基羰基取代,或代表苯基、苯氧基、苯基-C1-C4烷基、苯基-C1-C4烷氧基、苯氧基羰基或苯基-C1-C4烷氧基羰基,这些基团各任选被硝基、氰基、羧基、氟、氯、溴、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基和/或C1-C4烷氧基羰基取代,A3 还代表(在各种情况下任选地全部或部分氢化的)吡咯基、吡唑基、咪唑基、三唑基、呋喃基、环氧乙烷基、氧杂环丁烷基、二氧戊环基、噻吩基、噁唑基、异噁唑基、噻唑基、异噻唑基、噁二唑基、噻二唑基、吡啶基、嘧啶基、三嗪基、吡唑基-C1-C4烷基、呋喃基-C1-C4烷基、噻吩基-C1-C4烷基、噁唑基-C1-C4烷基、异噁唑基-C1-C4烷基、噻唑基-C1-C4烷基、吡啶基-C1-C4烷基、嘧啶基-C1-C4烷基、吡唑基甲氧基、呋喃基甲氧基、全氢吡喃基甲氧基或吡啶基甲氧基,R7 代表氢、氟或氯,或者在每种情况下两个相邻的基团-R3和R4、R4和R5、R5和R6或R6和R7-一起代表下列基团之一:-Q3-CQ4-,-Q3-CQ4-Q5-,-Q3-C(R8,R9)-Q5-,-C(R8,R9)-CQ4-,-C(R8,R9)-Q3-CQ4-,-Q3-C(R8,R9)-C(R8,R9)-,-Q3-C(R8,R9)-C(R8,R9)-Q5-,-C(R8,R9)-C(R8,R9)-CQ4-,-Q3-C(R8)=C(R8)-,-C(R8)=C(R8)-CQ4-,-Q3-C(R8,R9)-CQ4-,-N(R10)-C(R8;R9)-CQ4-,-C(R8)=N-,-Q3-CQ4-C(R8,R9)-,-Q3-CQ4-N(R10)-,-Q3-C(R8,R9)-CQ4-N(R10)-,-C(R8,R9)-Q3-CQ4-N(R10)-,-C(R8,R9)-C(R8,R9)-N(R10),-C(R8,R9)-C(R8,R9)-CQ4-N(R10)-,-C(R8)=C(R8)-N(R10)-,-C(R8)=C(R8)-CQ4-N(R10)-,-C(R8,R9)-CQ4-N(R10)-,-N(R10)-C(R8;R9)-CQ4-N(R10)-,-C(R8)=N-N(R10)-,-Q3-CQ4-C(R8,R9)-N(R10)-,Q3-C(R8,R9)-C(R8,R9)-CQ4-N(R10)-其中Q3、Q4和Q5相同或不同,各代表氧或硫,R8和R9相同或不同,各代表氢、氟、氯、溴或C1-C4烷基或一起代表C2-C5烷二基,和R10 代表氢、羟基,或代表烷基、烷基羰基、烷氧基羰基或烷基磺酰基,这些基团各在烷基中有1-6个碳原子并且各任选被氰基、氟、氯、C1-C4烷氧基、C1-C4烷基羰基或C1-C4烷氧基羰基取代,或代表链烯基或炔基,这些基团各具有2-6个碳原子并且各任选被氟、氯或溴取代,或代表环烷基或环烷基烷基,这些基团各在环烷基部分具有3-6个碳原子和如果适当在烷基部分具有1-3个碳原子并且各任选被氟、氯、溴或C1-C4烷基取代,或代表烷氧基或链烯基氧基,这些基团各最多具有6个碳原子并且各任选被氟和/或氯取代,或代表苄基或苄基氧基,这些基团各任选被氰基、氟、氯、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。n特别优选为1、2或3;Q特别优选为氧或硫;R1特别优选代表氢、甲酰基,或代表甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基,它们各自任选被氰基、氟、氯、 甲氧基或乙氧基取代,或代表丙烯基、丁烯基、丙炔基或丁炔基,它们各自任选被氟或氯取代,或代表环丙基、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,它们各自任选被氰基、氟、氯、甲基或乙基取代;R3 优选代表氢、硝基、氨基、氰基、甲酰氨基、氟、氯,或代表甲基、三氟甲基、乙酰基氨基、丙酰基氨基、丁酰基氨基、异丁酰基氨基、三氟乙酰基氨基、甲氧基羰基氨基、乙氧基羰基氨基、甲基氨基羰基氨基、乙基氨基羰基氨基、环丙基羰基氨基或苯基羰基氨基(苯甲酰基氨基);R4 优选代表氢、氟或氯;R5 优选代表氰基、硫代氨基甲酰基、氯、溴、甲基、三氟甲基、甲氧基、二氟甲氧基或三氟甲氧基;R6 特别优选代表下式基团:-A1-A2-A3其中A1 代表单键,或代表氧、硫、-SO-、-SO2-、-CO-或基团-N-A4-,其中A4代表氢、羟基、甲基、乙基、正-或异丙基、甲氧基、乙氧基、正-或异丙氧基、甲基磺酰基或乙基磺酰基,A1 还代表亚甲基、乙烷-1,1-二基、乙烷-1,2-二基、丙烷-1,1-二基、丙烷-1,2-二基、丙烷-1,3-二基、乙烯-1,2-二基、丙烯-1,2-二基、丙烯-1,3-二基、乙炔-1,2-二基、丙炔-1,2-二基或丙炔-1,3-二基,A2 代表单键,或代表氧、硫、-SO-、-SO2-、-CO-或基团-N-A4-,其中A4代表氢、羟基、甲基、乙基、正-或异丙基、甲氧基、乙氧基、正-或异丙氧基、甲基磺酰基、乙基磺酰基、正-或异丙基磺酰基或苯基磺酰基,A2 还代表亚甲基、乙烷-1,1-二基、乙烷-1,2-二基、丙烷-1,1-二基、丙烷-1,2-二基、丙烷-1,3-二基、乙烯-1,2-二基、丙烯-1,2-二基、丙烯-1,3-二基、乙炔-1,2-二基、丙炔-1,2-二基或丙炔-1,3-二基,A3 代表氢、羟基、氨基、氰基、硝基、羧基、氨基甲酰基、磺基、氟、氯、溴,或代表甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基、正-、异-、仲-或叔戊基、甲氧基、乙氧基、正-或异丙氧基、-正-、异-、仲-或叔丁氧基、正-、异-、仲-或叔戊氧基、甲硫基、乙硫基、正-或异丙硫基、正-、异-、仲-或叔丁硫基、甲基亚磺酰基、乙基亚磺酰基、正-或异丙亚磺酰基、甲基磺酰基、乙基磺酰基、正-或异丙磺酰基、甲基氨基、乙基氨基、正-或异丙基氨基、正-、异-、仲-或叔丁基氨基、二甲氨基、二乙氨基、甲氧基羰基、乙氧基羰基、正-或异丙氧基羰基、二甲氧基磷酰基、二乙氧基磷酰基或二丙氧基磷酰基、二异丙氧基磷酰基,这些基团各任选被氟、氯、甲氧基或乙氧基取代,或代表丙烯基、丁烯基、丙烯基氧基、丁烯基氧基、丙烯基氨基、丁烯基氨基、亚丙基氨基、亚丁基氨基、丙烯基氧基羰基、丁烯基氧基羰基、丙炔基、丁炔基、丙炔基氧基、丁炔基氧基、丙炔基氨基、丁炔基氨基、丙炔基氧基羰基或丁炔基氧基羰基,它们各自任选被氟或氯取代,或代表环丙基、环丁基、环戊基、环己基、环丙基氧基、环丁基氧基、环戊基氧基、环己基氧基、环丙基甲基、环丁基甲基、环戊基甲基、环己基甲基、环丙基甲氧基、环丁基甲氧基、环戊基甲氧基、环己基甲氧基、亚环戊基氨基、亚环己基氨基、环戊基氧基羰基、环己基氧基羰基、环戊基甲氧基羰基或环己基甲氧基羰基,它们各自任选被氟、氯、氰基、羧基、甲基、乙基、正-或异丙基、甲氧基羰基或乙氧基羰基取代,或代表苯基、苯氧基、苄基、苯基乙基、苄基氧基、苯氧基羰基、苄氧基羰基,它们各任选被硝基、氰基、羧基、氟、氯、溴、甲基、乙基、正-或异丙基、三氟甲基、甲氧基、乙氧基、正-或异丙氧基、二氟甲氧基、三氟甲氧基、甲氧基羰基和/或乙氧基羰基取代,A3 还代表(在各种情况下任选地全部或部分氢化的)吡咯基、吡唑基、咪唑基、三唑基、呋喃基、噻吩基、噁唑基、异噁唑基、噻唑基、异噻唑基、噁二唑基、噻二唑基、吡啶基、嘧啶基、三嗪基、吡唑基甲基、呋喃基甲基、噻吩基甲基、噁唑基甲基、异噁唑基甲基、噻唑基甲基、吡啶基甲基、嘧啶基甲基、吡唑基甲氧基、呋喃基甲氧基或吡啶基甲氧基;R7 优选代表氢、氟或氯。两个相邻的基团-R3和R4、R4和R5、R5和R6或R6和R7-一起优选代表下列基团之一:-Q3-CQ4-,-Q3-CQ4-Q5-,-Q3-C(R8,R9)-Q5-,-C(R8,R9)-CQ4-,-C(R8,R9)-Q3-CQ4-,-Q3-C(R8,R9)-C(R8,R9)-,-Q3-C(R8,R9)-C(R8,R9)-Q5-,-C(R8,R9)-C(R8,R9)-CQ4-,-Q3-C(R8)=C(R8)-,-C(R8)=C(R8)-CQ4-,-Q3-C(R8,R9)-CQ4-,-N(R10)-C(R8;R9)-CQ4-,-C(R8)=N-,-Q3-CQ4-C(R8,R9)-,-Q3-CQ4-N(R10)-,-Q3-C(R8,R9)-CQ4-N(R10)-,-C(R8,R9)-Q3-CQ4-N(R10)-,-C(R8,R9)-C(R8,R9)-N(R10)-,-C(R8,R9)-C(R8,R9)-CQ4-N(R10)-,-C(R8)=C(R8)-N(R10)-,-C(R8)=C(R8)-CQ4-N(R10)-,-C(R8,R9)-CQ4-N(R10)-,-N(R10)-C(R8;R9)-CQ4-N(R10)-,-C(R8)=N-N(R10)-,-Q3-CQ4-C(R8,R9)-N(R10)-,Q3-C(R8,R9)-C(R8,R9)-CQ4-N(R10)-其中Q3、Q4和Q5相同或不同,各代表氧或硫,R8和R9相同或不同,各代表氢、氟、氯、甲基或乙基或一起代表乙烷-1,2-二基(二亚甲基),和R10 代表氢、羟基,或代表甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基,这些基团各任选被氰基、氟、氯、甲氧基、乙氧基、乙酰基、丙酰基、甲氧基羰基或乙氧基羰基取代,或代表丙烯基、丁烯基、丙炔基或丁炔基,它们各自任选被氟、氯或溴取代,或代表环丙基、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,它们各自任选被氟、氯、溴、甲基或乙基取代,或代表甲氧基、乙氧基、正-或异丙氧基、正-、异-或仲丁氧基、丙烯基氧基或丁烯基氧基,它们各自任选被氟和/或氯取代,或代表苄基或苄基氧基,它们各任选被氰基、氟、氯、甲基、乙基、三氟甲基、甲氧基、乙氧基、二氟甲氧基或三氟甲氧基取代;n 非常特别优选为1或2;Q 非常特别优选为氧或硫;R1 非常特别优选代表甲基、乙基、正-或异丙基,它们各自任选被氰基、氟、氯、甲氧基或乙氧基取代;R3 特别优选代表氢、氟或氯;R4 特别优选代表氢;R5 特别优选代表氰基、硫代氨基甲酰基、氯、溴、甲基或三氟甲基;R6 特别优选代表下式基团:-A1-A2-A3其中A1 代表单键,A2 代表单键,A3 代表羟基、氨基、氰基、硝基、羧基、氨基甲酰基、磺基、氟、氯、溴,或代表甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基、正-、异-、仲-或叔戊基、甲氧基、乙氧基、正-或异丙氧基、正-、异-、仲-或叔丁氧基、正-、异-、仲-或叔戊氧基、甲硫基、乙硫基、正-或异丙硫基、正-、异-、仲-或叔丁硫基、甲基亚磺酰基、乙基亚磺酰基、正-或异丙亚磺酰基、甲基磺酰基、乙基磺酰基、正-或异丙磺酰基、甲基氨基、乙基氨基、正-或异丙基氨基、正-、异-、仲-或叔丁基氨基、二甲氨基、二乙氨基、甲氧基羰基、乙氧基羰基、正-或异丙氧基羰基,这些基团各任选被氟、氯、甲氧基或乙氧基取代,或代表丙烯基、丁烯基、丙烯基氧基、丁烯基氧基、丙烯基氨基、丁烯基氨基、亚丙基氨基、亚丁基氨基、丙烯基氧基羰基、丁烯基氧基羰基、丙炔基、丁炔基、丙炔基氧基、丁炔基氧基、丙炔基氨基、丁炔基氨基、丙炔基氧基羰基或丁炔基氧基羰基,它们各自任选被氟或氯取代,或代表环丙基氧基、环丁基氧基、环戊基氧基、环己基氧基、环丙基甲氧基、环丁基甲氧基、环戊基甲氧基、环己基甲氧基、环戊基氧基羰基、环己基氧基羰基、环戊基甲氧基羰基或环己基甲氧基羰基,它们各自任选被氟、氯、氰基、羧基、甲基、乙基、正-或异丙基、甲氧基羰基或乙氧基羰基取代,或代表苯氧基、苄基氧基、苯氧基羰基或苄氧基羰基,它们各任选被硝基、氰基、羧基、氟、氯、溴、甲基、乙基、正-或异丙基、三氟甲基、甲氧基、乙氧基、正-或异丙氧基、二氟甲氧基、三氟甲氧基、甲氧基羰基和/或乙氧基羰基取代;R7 特别优选代表氢。
根据本发明,优选含有上述作为优选的意义的结合的式(Ⅰ)化合物。
根据本发明,特别优选含有上述作为特别优选的意义的结合的式(Ⅰ)化合物。
根据本发明,非常特别优选含有上述作为非常特别优选的意义的结合的式(Ⅰ)化合物。非常特别优选的一组化合物是这样的式(Ⅰ)化合物,其中n 为1或2;Q 为氧或硫;R1 代表甲基、乙基、正-或异丙基,它们各自任选被氰基、氟、氯、甲氧基或乙氧基取代;R2 代表下式的芳基其中R3 代表氢、氟或氯;R4 代表氢;R5 代表氰基、硫代氨基甲酰基、氯、溴、甲基或三氟甲基;R6 代表下式基团:-A1-A2-A3其中A1 代表基团-N-A4-,其中A4代表氢、甲基磺酰基或乙基磺酰基,A2 代表单键或-CO-,A3 代表氢,或代表甲基、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、甲硫基、乙硫基、正-或异丙硫基、正-、异-、仲-或叔丁硫基、甲基磺酰基、乙基磺酰基、正-或异丙磺酰基,这些基团各任选被氟、氯、甲氧基或乙氧基取代,或代表环丙基、环丁基、环戊基、环己基、环丙基氧基、环丁基氧基、环戊基氧基、环己基氧基、环丙基甲基、环丁基甲基、环戊基甲基、环己基甲基、环丙基甲氧基、环丁基甲氧基、环戊基甲氧基、环己基甲氧基,它们各自任选被氟、氯、氰基、羧基、甲基、乙基、正-或异丙基、甲氧基羰基或乙氧基羰基取代,或代表苯基、苯氧基、苄基或苄基氧基,它们各任选被硝基、氰基、羧基、氟、氯、溴、甲基、乙基、正-或异丙基、三氟甲基、甲氧基、乙氧基、正-或异丙氧基、二氟甲氧基、三氟甲氧基、甲氧基羰基和/或乙氧基羰基取代;R7 代表氢。另一组特别优选的化合物是这样的式(Ⅰ)化合物,其中n 为1或2;Q 为氧或硫;R1 代表甲基、乙基、正-或异丙基,它们各自任选被氰基、氟、氯、甲氧基或乙氧基取代;R2 代表下式的芳基其中R3 代表氢、氟或氯;R4 代表氢;R5 代表氰基、硫代氨基甲酰基、氯、溴、甲基或三氟甲基;R6 代表下式基团:-A1-A2-A3其中A1 代表基团-N-A4-,其中A4代表氢、甲基磺酰基或乙基磺酰基,A2 代表-SO2-,A3 代表甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基,这些基团各任选被氟、氯、甲氧基或乙氧基取代,或代表环丙基、环丁基、环戊基或环己基,它们各自任选被氟、氯、氰基或甲基取代,或代表苯基或苄基,它们各任选被硝基、氰基、氟、氯、溴、甲基、乙基、三氟甲基、甲氧基、乙氧基、二氟甲氧基、三氟甲氧基、甲氧基羰基或乙氧基羰基取代;R7 代表氢。
上述一般或优选的基团定义不仅适用于式(Ⅰ)的终产物,而且相应地适用于每种情况下制备所需的原料和中间体。这些基团的定义可以随意地相互组合,即可以是各给定的优选范围之间的组合。
式(Ⅰ)的新的取代的1,3-二氮杂-2-(硫)氧代环烷烃类化合物的特征是具有强的和选择性的除草活性。
式(Ⅰ)的新的取代的1,3-二氮杂-2-(硫)氧代环烷烃类化合物通过下述方法得到:
如果适当在反应辅助剂存在下和如果适当在稀释剂存在下,使通式(Ⅱ)的1,3-二氮杂-2-(硫)氧代环烷烃类化合物与通式(Ⅲ)的卤素化合物反应,其中n、Q和R1如上定义,其中R2如上定义,和X1代表卤素,以及,如果适当的话,随后在取代基的定义范围内以常规的方式进行亲电或亲核取代反应。
原则上,通式(Ⅰ)化合物也可以如下所示那样合成:
如果适当在反应辅助剂例如吡啶存在下和如果适当在稀释剂如甲苯存在下,使通式(Ⅳ)的二胺与通式(Ⅴ)的(硫代)碳酸衍生物反应,其中n、Q、R1和R2如上所定义,以及Y1和Y2相同或不同,各代表卤素(特别是氯)、烷氧基(特别是甲氧基或乙氧基)、烷氧基烷氧基(特别是甲氧基乙氧基或乙氧基乙氧基)、苯氧基或咪唑基。
如果适当在反应辅助剂例如乙基二异丙基胺存在下和如果适当在稀释剂如乙腈存在下,使通式(Ⅵ)的1,3-二氮杂-2-(硫)氧代环烷烃类化合物与通式(Ⅶ)的卤素化合物反应,其中n、Q、R1和R2如上所定义,以及X2代表卤素(特别是氯、溴或碘)。
如果适当在反应辅助剂例如碳酸钾存在下和如果适当在稀释剂如丙酮存在下,使通式(Ⅷ)的(硫代)脲与通式(Ⅸ)的α,ω-二取代的烷烃化合物反应,其中n、Q、R1和R2如上所定义,以及E1和E2代表可以被亲核剂取代的离去基团如卤素(特别是氯或溴)或烷基磺酰基氧基(特别是甲基磺酰基氧基)。
如果,例如,使用1-甲基-咪唑烷-2-酮和2,4,5-三氟苯甲腈为原料,则本发明方法的反应过程可以用下面的反应式概括:
式(Ⅱ)提供了在制备本发明式(Ⅰ)化合物的本发明方法中用作起始原料的1,3-二氮杂-2-(硫)氧代环烷烃类化合物的一般定义。在式(Ⅱ)中,n、Q和R1各优选或特别是具有在上文有关本发明式(Ⅰ)化合物的描述中业已提到的n、Q和R1的优选或特别优选的含义。
式(Ⅱ)起始原料是已知的和/或可以通过本身已知的方法制备(参见,J.Am.Chem.Soc.80(1958),6409-6412;J.Chem.Soc.Perkin Trans.1,1981,2499-2503;J.Org.Chem.22(1957),1581;J.Org.Chem.28(1992),7339-7342;Synth.Commun.27(1997),3565-3571)。
通式(Ⅲ)提供在本发明方法中另一用作起始原料的卤素化合物的一般定义。在式(Ⅲ)中,R2优选或特别是具有在上文有关本发明式(Ⅰ)化合物的描述中业已提到的R2的优选、特别优选或非常特别优选的含义;X2优选代表氟或氯,特别是氟。
式(Ⅲ)起始原料是已知的和/或可以通过本身已知的方法制备(参见,EP-A-191181,EP-A-370332,EP-A-431373,EP-A-441004,EP-A-597360)。
本发明制备通式(Ⅰ)化合物的方法优选使用稀释剂进行。合适的稀释剂首先是惰性有机溶剂。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、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;醚类,如乙醚、异丙醚、二噁烷、四氢呋喃或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-N-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。
本发明制备通式(Ⅰ)化合物的方法优选使用反应辅助剂进行。合适的反应辅助剂通常是常规的无机或有机碱或酸受体。这些物质优选包括碱金属或碱土金属的乙酸盐、氨化物、碳酸盐、碳酸氢盐、氢化物、氢氧化物或醇盐,如乙酸钠、乙酸钾或乙酸钙、氨化锂、氨化钠、氨化钾或氨化钙、碳酸钠、碳酸钾或碳酸钙、碳酸氢钠、碳酸氢钾或碳酸氢钙、氢化锂、氢化钠、氢化钾或氢化钙、氢氧化锂、氢氧化钠、氢氧化钾或氢氧化钙、甲醇钠、甲醇钾、乙醇钠、乙醇钾、正或异丙醇钠、正-或异丙醇钾,正-、异-、仲-或叔丁醇钠或正-、异-、仲-或叔丁醇钾;另外还有碱性有机氮化合物,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-乙基-、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)。
进行本发明方法时,反应温度可以在相对宽的范围内变化。通常,反应是在0℃至150℃,优选在20℃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,通常采用大致等摩尔量的起始原料。然而,也可以相对大地过量采用反应组分之一。反应通常是在适合的稀释剂中在反应辅助剂存在下进行的,且反应混合物通常在所需的温度下搅拌几小时。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:芥属、独行草属、猪殃殃属、繁缕属、母菊属、春黄菊属、牛膝属、藜属、荨麻属、千里光属、苋属、马齿苋属、苍耳属、旋花属、甘薯属、蓼属、田菁属、豚草属、蓟属、飞廉属、苦苣菜属、茄属、蔊菜属、节节草属、母草属、野芝麻属、婆婆纳属、苘麻属、刺酸模属、曼陀罗属、堇菜属、鼬瓣花属、罂粟属、矢车菊属、三叶草属、毛茛属和蒲公英属,
下列属的双子叶作物:棉属、大豆属、甜菜属、胡萝卜属、菜豆属、豌豆属、茄属、亚麻属、甘薯属、巢菜属、烟草属、蕃茄属、花生属、芸苔属、莴苣属、黄瓜属和南瓜属,
下列属的单子叶杂草:稗属、狗尾草属、黍属、马唐属、梯牧草属、早熟禾属、羊茅属、蟋蟀草属、臂形草属、黑麦草属、雀麦属、燕麦属、莎草属、高梁属、冰草属、狗牙根属、雨久花属、飘拂草属、慈菇属、荸荠属、藨草属、雀稗属、鸭嘴草属、尖瓣花属、龙爪茅属、剪股颖属、看麦娘属和风草属,
下列属的单子叶作物:稻属、玉米属、小麦属、大麦属、燕麦属、黑麦属、高梁属、黍属、甘蔗属、凤梨属、天门冬属和葱属。
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。
取决于化合物的浓度,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,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。且本发明化合物还可以用于选择性地防治一年生作物中的杂草。
本发明式(Ⅰ)化合物特别适合于以芽前和芽后二种方式选择性地防治单子叶作物中的单子叶和双子叶杂草。
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、喷粉剂、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。
在用水作扩充剂的情况下,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。其它的添加剂可以是矿物油和植物油。
也可能使用着色剂,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%。
为防治杂草,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一起的混合物使用,它们可以是终制剂或桶混物。
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、amidochlor、酰嘧黄隆、莎稗磷、磺草灵、莠去津、azafenidin、四唑嘧黄隆、草除灵、呋草黄、苄嘧黄隆(甲酯)、灭草松、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、butroxydim、丁草特、cafenstrole、caloxydim、双酰草胺、carfentrazone(-ethyl)、甲氧除草醚、灭草平、杀草敏、氯嘧黄隆(乙酯)、草枯醚、绿黄隆、绿麦隆、环庚草醚、醚黄隆、烯草酮、炔草酸、异噁草松、氯甲酰草胺、二氟吡啶酸、clopyrasulfuron(-methyl)、cloransulam(-methyl)、cumyluron、氰草津、灭草特、环丙嘧磺隆、噻草酮、氰氟草酯、2,4-滴、2,4-滴丁酸、2,4-滴丙酸、甜菜安、燕麦敌、麦草畏、禾草灵(甲酯)、diclosulam、乙酰甲草胺、野燕枯、吡氟酰草胺、diflufenzopyr、唑隆、哌草丹、二甲草胺、异戊净、二甲吩草胺、dimexyflam、氨氟灵、双苯酰草胺、敌草快、氟硫草定、敌草隆、dymron、epoprodan、茵草敌、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、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)、唑嘧磺草胺、氟烯草酸、丙炔氟草胺、flumipropyn、唑嘧磺草胺、氟草隆、氟咯草酮、乙羧氟草醚、胺草唑、flupropacil、flurpyrsulfuron(-methyl、sodium)、芴丁酯、氟丁酮、氟草烟、调嘧醇、flurtamone、fluthiacet(-methyl)、fluthiamid、氟黄胺草醚、草铵磷(铵盐)、草甘磷(异丙铵盐)、halosafen、吡氟氯禾灵(乙氧基乙酯)、吡氟氯禾灵(-P-甲酯)、环嗪酮、咪草酯(甲酯)、imazamethapyr、imazamox、灭草烟、灭草喹、咪草烟、咪唑黄隆、碘苯腈、异丙乐灵、异丙隆、异噁隆、异噁酰草、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、苯噻草胺、苯嗪草酮、吡草胺、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、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、安磺灵、oxadiargyl、噁草酮、oxasulfuron、oxaziclomefone、乙氧氟草醚、百草枯、pelargonic acid、二甲戊乐灵、pentoxazone、甜菜宁、哌草磷、丙草胺、氟嘧黄隆(甲酯)、扑草净、毒草胺、敌稗、噁草酸、异丙草胺、炔苯酰草胺、苄草丹、氟磺隆、pyraflufen(-ethyl)、吡唑特、吡嘧黄隆、苄草唑、pyribenzoxim、稗草丹、哒草特、pyriminobac(-methyl)、嘧草硫醚、二氯喹啉酸、喹草酸、灭草醌、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、甲嘧黄隆、sulfosate、sulfosulfuron、牧草胺、丁噻隆、特丁津、特丁净、噻吩草胺、thiafluamide、噻唑烟酸、thidiazimin、噻吩黄隆、杀草丹、仲草丹、肟草酮、野燕畏、醚苯黄隆、苯黄隆、绿草定、灭草环、氟乐灵和氟胺黄隆。
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5.8g(50mmol)的1-甲基-咪唑烷-硫酮、8.6g(55mmol)2,4,5-三氟苄腈、7.6g(55mmol)碳酸钾和50ml二甲基亚砜的混合物在80℃搅拌16小时。冷却后将混合物倾入大约等体积的二氯甲烷和水的搅拌混合物中,并用2N的盐酸酸化。分出有机相,用水洗涤,用硫酸钠干燥后过滤。将滤液在水泵真空下浓缩,残留物用乙醚消化,通过吸滤分离产生的结晶状产物。
得到9.5g(理论量的75%)1-甲基-3-(4-氰基-2,5-二氟苯基)咪唑烷-2-硫酮,熔点143℃。
实施例2(随后的反应)
将2.0g(8mmol)的1-甲基-3-(4-氰基-2,5-二氟苯基)咪唑烷-2-硫酮、1.8g(16mmol)乙磺酰胺、2.2g(16mmol)的碳酸钾和50ml二甲基亚砜的混合物在100℃搅拌16小时。冷却后将混合物倾入大约等体积的二氯甲烷和水的搅拌混合物中,并用2N的盐酸酸化。分出有机相,用水洗涤,用硫酸钠干燥后过滤。将滤液在水泵真空下浓缩,残留物用异丙醇消化,通过吸滤分离产生的结晶状产物。
得到1.9g(理论量的68%)1-甲基-3-(4-氰基-2-氟-5-乙磺酰氨基苯基)咪唑烷-2-硫酮,熔点174℃。
可以类似于制备实施例1和2并根据本发明制备方法的一般性描述制备的式(Ⅰ)化合物的其他实例是下表1中所列出的那些。
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:0.01摩尔含水磷酸盐缓冲溶液,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。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2、5、8、9、10、11和12的化合物对杂草显示出强活性,同时在一些情况下能被作物如玉米很好地耐受。
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2、8、9、10和12的化合物对杂草显示出强活性,且它们中的一些能被作物如大麦很好地耐受。
Claims (9)
2.根据权利要求1的取代的1,3-二氮杂-2-(硫)氧代环烷烃类化合物,其特征在于n为1、2或3;Q为氧或硫;R1代表氢、甲酰基或代表各在烷基中具有1-6个碳原子的并且各任选被氰基、卤素、C1-C4烷氧基、C1-C4烷基羰基、C1-C4烷氧基羰基或吗啉基取代的烷基、烷氧基、烷基氨基、二烷基氨基,或代表各具有2-6个碳原子的并且各任选被氰基、卤素或C1-C4烷氧基羰基取代的链烯基或炔基,或代表各在环烷基中具有3-6个碳原子的和如果适当的话在烷基中具有1-4个碳原子的并且各任选被氰基、卤素或C1-C4烷基取代的环烷基或环烷基烷基;以及R2代表如下定义的芳基其中R3 代表氢、硝基、氨基、氰基、甲酰氨基、卤素,或代表烷基、烷氧基、烷基羰基氨基、烷氧基羰基氨基、烷基氨基羰基氨基,这些基团各在烷基部分具有1-6个碳原子并且各任选被氰基、卤素或C1-C4烷氧基取代,或代表环烷基羰基氨基,该基团在环烷基部分具有3-6个碳原子并且该基团任选被氰基、卤素、C1-C4烷基或C1-C4卤代烷基取代,或代表苯基羰基氨基,该基团任选被氰基、硝基、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;R4 代表氢、硝基、氰基、氟、氯或溴;R5 代表硝基、氰基、羧基、氨基甲酰基、硫代氨基甲酰基、羟基、氟、氯、溴,或代表烷基、烷氧基、烷基羰基或烷氧基羰基,这些基团各具有最多4个碳原子并且各任选被氟和/或氯取代;R6 代表下式基团:-A1-A2-A3其中A1 代表单键,或代表氧、硫、-SO-、-SO2-、-CO-或基团-N-A4-,其中A4代表氢、羟基、C1-C4烷基、C3-C4链烯基、C3-C4炔基、C1-C4烷氧基、苯基、C1-C4烷基羰基、苯基羰基、C1-C4烷基磺酰基或苯基磺酰基,A1 还代表C1-C6链烷二基、C2-C6链烯二基、C2-C6氮杂链烯二基、C2-C6炔二基、C3-C6环烷二基、C3-C6环烯二基或亚苯基,这些基团各任选被氟、氯或溴取代,A2 代表单键,或代表氧、硫、-SO-、-SO2-、-CO-或基团-N-A4-,其中A4代表氢、羟基、C1-C4烷基、C1-C4烷氧基、苯基、C1-C4烷基磺酰基或苯基磺酰基,A2 还代表C1-C6链烷二基、C2-C6链烯二基、C2-C6氮杂链烯二基、C2-C6炔二基、C3-C6环烷二基、C3-C6环烯二基或亚苯基,这些基团各任选被氟、氯或溴取代,A3 代表氢、羟基、巯基、氨基、氰基、异氰基、氰硫基、硝基、羧基、氨基甲酰基、硫代氨基甲酰基、磺基、氯磺基、氟、氯、溴,或代表烷基、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、烷氧基羰基或二烷氧基(硫代)磷酰基,这些基团各在烷基中有1-6个碳原子并且各任选被氟、氯或C1-C4烷氧基取代,或代表链烯基、链烯基氧基、链烯基氨基、亚烷基氨基、链烯基氧基羰基、炔基、炔氧基、炔基氨基或炔氧基羰基,这些基团各在链烯基、亚烷基或炔基中具有2-6个碳原子并且各任选被氟或氯取代,或代表环烷基、环烷基氧基、环烷基烷基、环烷基烷氧基、亚环烷基氨基、环烷氧基羰基或环烷基烷氧基羰基,这些基团各在环烷基部分具有3-6个碳原子和如果适当在烷基部分具有1-4个碳原子并且各任选被氟、氯、氰基、羧基、C1-C4烷基和/或C1-C4烷氧基羰基取代,或代表苯基、苯氧基、苯基-C1-C4烷基、苯基-C1-C4烷氧基、苯氧基羰基或苯基-C1-C4烷氧基羰基,这些基团各任选被硝基、氰基、羧基、氟、氯、溴、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基和/或C1-C4烷氧基羰基取代,A3 还代表(在各种情况下任选地全部或部分氢化的)吡咯基、吡唑基、咪唑基、三唑基、呋喃基、环氧乙烷基、氧杂环丁烷基、二氧戊环基、噻吩基、噁唑基、异噁唑基、噻唑基、异噻唑基、噁二唑基、噻二唑基、吡啶基、嘧啶基、三嗪基、吡唑基-C1-C4烷基、呋喃基-C1-C4烷基、噻吩基-C1-C4烷基、噁唑基-C1-C4烷基、异噁唑基-C1-C4烷基、噻唑基-C1-C4烷基、吡啶基-C1-C4烷基、嘧啶基-C1-C4烷基、吡唑基甲氧基、呋喃基甲氧基、全氢吡喃基甲氧基或吡啶基甲氧基,R7 代表氢、氟或氯,或者在每种情况下两个相邻的基团-R3和R4、R4和R5、R5和R6或R6和R7-一起代表下列基团之一:-Q3-CQ4-,-Q3-CQ4-Q5-,-Q3-C(R8,R9)-Q5-,-C(R8,R9)-CQ4-,-C(R8,R9)-Q3-CQ4-,-Q3-C(R8,R9)-C(R8,R9)-,-Q3-C(R8,R9)-C(R8,R9)-Q5-,-C(R8,R9)-C(R8,R9)-CQ4-,-Q3-C(R8)=C(R8)-,-C(R8)=C(R8)-CQ4-,-Q3-C(R8,R9)-CQ4-,-N(R10)-C(R8;R9)-CQ4-,-C(R8)=N-,-Q3-CQ4-C(R8,R9)-,-Q3-CQ4-N(R10)-,-Q3-C(R8,R9)-CQ4-N(R10)-,-C(R8,R9)-Q3-CQ4-N(R10)-,-C(R8,R9)-C(R8,R9)-N(R10)-,-C(R8,R9)-C(R8,R9)-CQ4-N(R10)-,-C(R8)=C(R8)-N(R10)-,-C(R8)=C(R8)-CQ4-N(R10)-,-C(R8,R9)-CQ4-N(R10)-,-N(R10)-C(R8;R9)-CQ4-N(R10)-,-C(R8)=N-N(R10)-,-Q3-CQ4-C(R8,R9)-N(R10)-,Q3-C(R8,R9)-C(R8,R9)-CQ4-N(R10)-其中Q3、Q4和Q5相同或不同,各代表氧或硫,R8和R9相同或不同,各代表氢、氟、氯、溴或C1-C4烷基或一起代表C2-C5烷二基,和R10 代表氢、羟基,或代表烷基、烷基羰基、烷氧基羰基或烷基磺酰基,这些基团各在烷基中有1-6个碳原子并且各任选被氰基、氟、氯、C1-C4烷氧基、C1-C4烷基羰基或C1-C4烷氧基羰基取代,或代表链烯基或炔基,这些基团各具有2-6个碳原子并且各任选被氟、氯或溴取代,或代表环烷基或环烷基烷基,这些基团各在环烷基部分具有3-6个碳原子和如果适当在烷基部分具有1-3个碳原子并且各任选被氟、氯、溴或C1-C4烷基取代,或代表烷氧基或链烯基氧基,这些基团各最多具有6个碳原子并且各任选被氟和/或氯取代,或代表苄基或苄基氧基,这些基团各任选被氰基、氟、氯、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。
3.根据权利要求1的取代的1,3-二氮杂-2-(硫)氧代环烷烃类化合物,其特征在于n为1、2或3;Q为氧或硫;R1代表氢、甲酰基,或代表甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基,它们各自任选被氰基、氟、氯、甲氧基或乙氧基取代,或代表丙烯基、丁烯基、丙炔基或丁炔基,它们各自任选被氟或氯取代,或代表环丙基、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,它们各自任选被氰基、氟、氯、甲基或乙基取代;R2代表如下定义的芳基其中R3 代表氢、硝基、氨基、氰基、甲酰氨基、氟、氯,或代表甲基、三氟甲基、乙酰基氨基、丙酰基氨基、丁酰基氨基、异丁酰基氨基、三氟乙酰基氨基、甲氧基羰基氨基、乙氧基羰基氨基、甲基氨基羰基氨基、乙基氨基羰基氨基、环丙基羰基氨基或苯基羰基氨基(苯甲酰基氨基);R4 代表氢、氟或氯;R5 代表氰基、硫代氨基甲酰基、氯、溴、甲基、三氟甲基、甲氧基、二氟甲氧基或三氟甲氧基;R6 代表下式基团:-A1-A2-A3其中A1 代表单键,或代表氧、硫、-SO-、-SO2-、-CO-或基团-N-A4-,其中A4代表氢、羟基、甲基、乙基、正-或异丙基、甲氧基、乙氧基、正-或异丙氧基、甲基磺酰基或乙基磺酰基,A1 还代表亚甲基、乙烷-1,1-二基、乙烷-1,2-二基、丙烷-1,1-二基、丙烷-1,2-二基、丙烷-1,3-二基、乙烯-1,2-二基、丙烯-1,2-二基、丙烯-1,3-二基、乙炔-1,2-二基、丙炔-1,2-二基或丙炔-1,3-二基,A2 代表单键,或代表氧、硫、-SO-、-SO2-、-CO-或基团-N-A4-,其中A4代表氢、羟基、甲基、乙基、正-或异丙基、甲氧基、乙氧基、正-或异丙氧基、甲基磺酰基、乙基磺酰基、正-或异丙基磺酰基或苯基磺酰基,A2 还代表亚甲基、乙烷-1,1-二基、乙烷-1,2-二基、丙烷-1,1-二基、丙烷-1,2-二基、丙烷-1,3-二基、乙烯-1,2-二基、丙烯-1,2-二基、丙烯-1,3-二基、乙炔-1,2-二基、丙炔-1,2-二基或丙炔-1,3-二基,A3 代表氢、羟基、氨基、氰基、硝基、羧基、氨基甲酰基、磺基、氟、氯、溴,或代表甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基、正-、异-、仲-或叔戊基、甲氧基、乙氧基、正-或异丙氧基、正-、异-、仲-或叔丁氧基、正-、异-、仲-或叔戊氧基、甲硫基、乙硫基、正-或异丙硫基、正-、异-、仲-或叔丁硫基、甲基亚磺酰基、乙基亚磺酰基、正-或异丙亚磺酰基、甲基磺酰基、乙基磺酰基、正-或异丙磺酰基、甲基氨基、乙基氨基、正-或异丙基氨基、正-、异-、仲-或叔丁基氨基、二甲氨基、二乙氨基、甲氧基羰基、乙氧基羰基、正-或异丙氧基羰基、二甲氧基磷酰基、二乙氧基磷酰基或二丙氧基磷酰基、二异丙氧基磷酰基,这些基团各任选被氟、氯、甲氧基或乙氧基取代,或代表丙烯基、丁烯基、丙烯基氧基、丁烯基氧基、丙烯基氨基、丁烯基氨基、亚丙基氨基、亚丁基氨基、丙烯基氧基羰基、丁烯基氧基羰基、丙炔基、丁炔基、丙炔基氧基、丁炔基氧基、丙炔基氨基、丁炔基氨基、丙炔基氧基羰基或丁炔基氧基羰基,它们各自任选被氟或氯取代,或代表环丙基、环丁基、环戊基、环己基、环丙基氧基、环丁基氧基、环戊基氧基、环己基氧基、环丙基甲基、环丁基甲基、环戊基甲基、环己基甲基、环丙基甲氧基、环丁基甲氧基、环戊基甲氧基、环己基甲氧基、亚环戊基氨基、亚环己基氨基、环戊基氧基羰基、环己基氧基羰基、环戊基甲氧基羰基或环己基甲氧基羰基,它们各自任选被氟、氯、氰基、羧基、甲基、乙基、正-或异丙基、甲氧基羰基或乙氧基羰基取代,或代表苯基、苯氧基、苄基、苯基乙基、苄基氧基、苯氧基羰基、苄氧基羰基,它们各任选被硝基、氰基、羧基、氟、氯、溴、甲基、乙基、正-或异丙基、三氟甲基、甲氧基、乙氧基、正-或异丙氧基、二氟甲氧基、三氟甲氧基、甲氧基羰基和/或乙氧基羰基取代,A3 还代表(在各种情况下任选地全部或部分氢化的)吡咯基、吡唑基、咪唑基、三唑基、呋喃基、噻吩基、噁唑基、异噁唑基、噻唑基、异噻唑基、噁二唑基、噻二唑基、吡啶基、嘧啶基、三嗪基、吡唑基甲基、呋喃基甲基、噻吩基甲基、噁唑基甲基、异噁唑基甲基、噻唑基甲基、吡啶基甲基、嘧啶基甲基、吡唑基甲氧基、呋喃基甲氧基或吡啶基甲氧基;R7 代表氢、氟或氯,或者两个相邻的基团-R3和R4、R4和R5、R5和R6或R6和R7-一起代表下列基团之一:-Q3-CQ4-,-Q3-CQ4-Q5-,-Q3-C(R8,R9)-Q5-,-C(R8,R9)-CQ4-,-C(R8,R9)-Q3-CQ4-,-Q3-C(R8,R9)-C(R8,R9)-,-Q3-C(R8,R9)-C(R8,R9)-Q5-,-C(R8,R9)-C(R8,R9)-CQ4-,-Q3-C(R8)=C(R8)-,-C(R8)=C(R8)-CQ4-,-Q3-C(R8,R9)-CQ4-,-N(R10)-C(R8;R9)-CQ4-,-C(R8)=N-,-Q3-CQ4-C(R8,R9)-,-Q3-CQ4-N(R10)-,-Q3-C(R8,R9)-CQ4-N(R10)-,-C(R8,R9)-Q3-CQ4-N(R10)-,-C(R8,R9)-C(R8,R9)-N(R10)-,-C(R8,R9)-C(R8,R9)-CQ4-N(R10)-,-C(R8)=C(R8)-N(R10)-,-C(R8)=C(R8)-CQ4-N(R10)-,-C(R8,R9)-CQ4-N(R10)-,-N(R10)-C(R8;R9)-CQ4-N(R10)-,-C(R8)=N-N(R10)-,-Q3-CQ4-C(R8,R9)-N(R10)-,Q3-C(R8,R9)-C(R8,R9)-CQ4-N(R10)-其中Q3、Q4和Q5相同或不同,各代表氧或硫,R8和R9相同或不同,各代表氢、氟、氯、甲基或乙基或一起代表乙烷-1,2-二基(二亚甲基),和R10 代表氢、羟基,或代表甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基,这些基团各任选被氰基、氟、氯、甲氧基、乙氧基、乙酰基、丙酰基、甲氧基羰基或乙氧基羰基取代,或代表丙烯基、丁烯基、丙炔基或丁炔基,它们各自任选被氟、氯或溴取代,或代表环丙基、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,它们各自任选被氟、氯、溴、甲基或乙基取代,或代表甲氧基、乙氧基、正-或异丙氧基、正-、异-或仲丁氧基、 丙烯基氧基或丁烯基氧基,它们各自任选被氟和/或氯取代,或代表苄基或苄基氧基,它们各任选被氰基、氟、氯、甲基、乙基、三氟甲基、甲氧基、乙氧基、二氟甲氧基或三氟甲氧基取代。
4.根据权利要求1的取代的1,3-二氮杂-2-(硫)氧代环烷烃类化合物,其特征在于n 为1或2;Q 为氧或硫;R1 代表甲基、乙基、正-或异丙基,它们各自任选被氰基、氟、氯、甲氧基或乙氧基取代;R2代表如下定义的芳基其中R3 代表氢、氟或氯;R4 代表氢;R5 代表氰基、硫代氨基甲酰基、氯、溴、甲基或三氟甲基;R6 代表下式基团:-A1-A2-A3其中A1 代表单键,A2 代表单键,A3 代表羟基、氨基、氰基、硝基、羧基、氨基甲酰基、磺基、氟、氯、溴,或代表甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基、正-、异-、仲-或叔戊基、甲氧基、乙氧基、正-或异丙氧基、正-、异-、仲-或叔丁氧基、正-、异-、仲-或叔戊氧基、甲硫基、乙硫基、正-或异丙硫基、正-、异-、仲-或叔丁硫基、甲基亚磺酰基、乙基亚磺酰基、正-或异丙亚磺酰基、甲基磺酰基、乙基磺酰基、正-或异丙磺酰基、甲基氨基、乙基氨基、正-或异丙基氨基、正-、异-、仲-或叔丁基氨基、二甲氨基、二乙氨基、甲氧基羰基、乙氧基羰基、正-或异丙氧基羰基,这些基团各任选被氟、氯、 甲氧基或乙氧基取代,或代表丙烯基、丁烯基、丙烯基氧基、丁烯基氧基、丙烯基氨基、丁烯基氨基、亚丙基氨基、亚丁基氨基、丙烯基氧基羰基、丁烯基氧基羰基、丙炔基、丁炔基、丙炔基氧基、丁炔基氧基、丙炔基氨基、丁炔基氨基、丙炔基氧基羰基或丁炔基氧基羰基,它们各自任选被氟或氯取代,或代表环丙基氧基、环丁基氧基、环戊基氧基、环己基氧基、环丙基甲氧基、环丁基甲氧基、环戊基甲氧基、环己基甲氧基、环戊基氧基羰基、环己基氧基羰基、环戊基甲氧基羰基或环己基甲氧基羰基,它们各自任选被氟、氯、氰基、羧基、甲基、乙基、正-或异丙基、甲氧基羰基或乙氧基羰基取代,或代表苯氧基、苄基氧基、苯氧基羰基或苄氧基羰基,它们各任选被硝基、氰基、羧基、氟、氯、溴、甲基、乙基、正-或异丙基、三氟甲基、甲氧基、乙氧基、正-或异丙氧基、二氟甲氧基、三氟甲氧基、甲氧基羰基和/或乙氧基羰基取代;以及R7 代表氢。
5.根据权利要求1的取代的1,3-二氮杂-2-(硫)氧代环烷烃类化合物,其特征在于n 为1或2;Q 为氧或硫;R1 代表甲基、乙基、正-或异丙基,它们各自任选被氰基、氟、氯、甲氧基或乙氧基取代;R2 代表下式的芳基其中R3 代表氢、氟或氯;R4 代表氢;R5 代表氰基、硫代氨基甲酰基、氯、溴、甲基或三氟甲基;R6 代表下式基团:-A1-A2-A3其中A1 代表基团-N-A4-,其中A4代表氢、甲基磺酰基或乙基磺酰基,A2 代表单键或-CO-,A3 代表氢,或代表甲基、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、甲硫基、乙硫基、正-或异丙硫基、正-、异-、仲-或叔丁硫基、甲基磺酰基、乙基磺酰基、正-或异丙磺酰基,这些基团各任选被氟、氯、甲氧基或乙氧基取代,或代表环丙基、环丁基、环戊基、环己基、环丙基氧基、环丁基氧基、环戊基氧基、环己基氧基、环丙基甲基、环丁基甲基、环戊基甲基、环己基甲基、环丙基甲氧基、环丁基甲氧基、环戊基甲氧基、环己基甲氧基,它们各自任选被氟、氯、氰基、羧基、甲基、乙基、正-或异丙基、甲氧基羰基或乙氧基羰基取代,或代表苯基、苯氧基、苄基或苄基氧基,它们各任选被硝基、氰基、羧基、氟、氯、溴、甲基、乙基、正-或异丙基、三氟甲基、甲氧基、乙氧基、正-或异丙氧基、二氟甲氧基、三氟甲氧基、甲氧基羰基和/或乙氧基羰基取代;以及R7 代表氢。
6.根据权利要求1的取代的1,3-二氮杂-2-(硫)氧代环烷烃类化合物,其特征在于n 为1或2;Q 为氧或硫;R1 代表甲基、乙基、正-或异丙基,它们各自任选被氰基、氟、氯、甲氧基或乙氧基取代;R2 代表下式的芳基其中R3 代表氢、氟或氯;R4 代表氢;R5 代表氰基、硫代氨基甲酰基、氯、溴、甲基或三氟甲基;R6 代表下式基团:-A1-A2-A3其中A1 代表基团-N-A4-,其中A4代表氢、甲基磺酰基或乙基磺酰基,A2 代表-SO2-,A3 代表甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基,这些基团各任选被氟、氯、甲氧基或乙氧基取代,或代表环丙基、环丁基、环戊基或环己基,它们各自任选被氟、氯、氰基或甲基取代,或代表苯基或苄基,它们各任选被硝基、氰基、氟、氯、溴、甲基、乙基、三氟甲基、甲氧基、乙氧基、二氟甲氧基、三氟甲氧基、甲氧基羰基或乙氧基羰基取代;以及R7 代表氢。
8.除草组合物,其特征在于,它们含有至少一种权利要求1-6之一的取代的1,3-二氮杂-2-(硫)氧代环烷烃类化合物。
9.权利要求1-6之一的至少一种取代的1,3-二氮杂-2-(硫)氧代环烷烃类化合物防治不希望的植物的用途。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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DE19822678A DE19822678A1 (de) | 1998-05-20 | 1998-05-20 | Substituierte 1,3-Diaza-2-(thi)oxo-cycloalkane |
DE19822678.0 | 1998-05-20 |
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CN1301257A true CN1301257A (zh) | 2001-06-27 |
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CN99806393A Pending CN1301257A (zh) | 1998-05-20 | 1999-05-18 | 取代的1,3-二氮杂-2-(硫)氧化环烷烃类化合物 |
Country Status (9)
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EP (1) | EP1080077A1 (zh) |
JP (1) | JP2002515492A (zh) |
KR (1) | KR20010043505A (zh) |
CN (1) | CN1301257A (zh) |
AU (1) | AU4263999A (zh) |
BR (1) | BR9910610A (zh) |
CA (1) | CA2332443A1 (zh) |
DE (1) | DE19822678A1 (zh) |
WO (1) | WO1999059977A1 (zh) |
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WO2017002201A1 (ja) * | 2015-06-30 | 2017-01-05 | 株式会社エス・ディー・エス バイオテック | シクロプロパンカルボン酸アミド化合物及びそれらを含有する除草剤 |
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DE1126392B (de) * | 1959-10-15 | 1962-03-29 | Bayer Ag | Verfahren zur Herstellung cyclischer Harnstoffe und Thioharnstoffe |
FR1394708A (fr) * | 1962-10-19 | 1965-04-09 | American Cyanamid Co | Procédé de préparation d'imidazolidinones et imidazolidinethiones substituées |
CH427826A (de) * | 1961-11-07 | 1967-01-15 | Bayer Ag | Verfahren zur Herstellung von Imidazolidin-Derivaten |
FR1516714A (fr) * | 1962-11-07 | 1968-02-05 | Bayer Ag | Procédé de préparation de dérivés de l'imidazolidine |
DE1226589B (de) * | 1963-09-12 | 1966-10-13 | Asta Werke Ag Chem Fab | Verfahren zur Herstellung von Imidazolidonen |
GB1108918A (en) * | 1966-01-15 | 1968-04-10 | Bayer Ag | 2-imidazolidone derivatives |
FR1531143A (fr) * | 1966-07-16 | 1968-06-28 | Bayer Ag | Procédé de fabrication de dérivés de la 2-imidazolidone à substituants basiques |
US3702327A (en) * | 1970-12-28 | 1972-11-07 | Aldrich Chem Co Inc | N-beta-1-(3-phenylimidazolidin-2-one)ethyl 4,4-ethylene dioxypiperidines |
US3876657A (en) * | 1971-06-03 | 1975-04-08 | Ashland Oil Inc | Preparation of 1-substituted-2-imidazolidinones |
AT311956B (de) * | 1971-06-07 | 1973-12-10 | Boehringer Sohn Ingelheim | Verfahren zur Herstellung neuer Phenylimidazolidinonderivate und ihrer Salze |
CH547288A (de) * | 1971-06-23 | 1974-03-29 | Ciba Geigy Ag | Verfahren zur herstellung neuer heterocyclischer stoffe. |
DK529378A (da) * | 1978-01-09 | 1979-07-10 | Shell Int Research | Anilidderivater |
EP0011693A1 (de) * | 1978-10-03 | 1980-06-11 | Ciba-Geigy Ag | Neue N-(trifluormethansulfonylaminophenyl)-substituierte N-Heterocyclen, ihre Herstellung, sie enthaltende Mittel und ihre Verwendung zur Beeinflussung des Pflanzenwachstums |
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DE3324903A1 (de) * | 1983-07-09 | 1985-01-17 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung substituierter ethylenharnstoffe sowie neue n-vinylethylenharnstoffe |
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1998
- 1998-05-20 DE DE19822678A patent/DE19822678A1/de not_active Withdrawn
-
1999
- 1999-05-18 JP JP2000549596A patent/JP2002515492A/ja active Pending
- 1999-05-18 KR KR1020007012595A patent/KR20010043505A/ko not_active Application Discontinuation
- 1999-05-18 CN CN99806393A patent/CN1301257A/zh active Pending
- 1999-05-18 AU AU42639/99A patent/AU4263999A/en not_active Abandoned
- 1999-05-18 WO PCT/EP1999/003422 patent/WO1999059977A1/de not_active Application Discontinuation
- 1999-05-18 EP EP99952091A patent/EP1080077A1/de not_active Withdrawn
- 1999-05-18 CA CA002332443A patent/CA2332443A1/en not_active Abandoned
- 1999-05-18 BR BR9910610-8A patent/BR9910610A/pt not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
BR9910610A (pt) | 2001-01-09 |
WO1999059977A1 (de) | 1999-11-25 |
CA2332443A1 (en) | 1999-11-25 |
JP2002515492A (ja) | 2002-05-28 |
EP1080077A1 (de) | 2001-03-07 |
DE19822678A1 (de) | 1999-11-25 |
KR20010043505A (ko) | 2001-05-25 |
AU4263999A (en) | 1999-12-06 |
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