CN110461833A - 2-氨基-5-氧基烷基嘧啶衍生物及其用于防治不希望的植物生长的用途 - Google Patents
2-氨基-5-氧基烷基嘧啶衍生物及其用于防治不希望的植物生长的用途 Download PDFInfo
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- CN110461833A CN110461833A CN201880022605.7A CN201880022605A CN110461833A CN 110461833 A CN110461833 A CN 110461833A CN 201880022605 A CN201880022605 A CN 201880022605A CN 110461833 A CN110461833 A CN 110461833A
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- alkyl
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- carbonyl
- alkoxy
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- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 title claims description 19
- 230000008635 plant growth Effects 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 231
- 150000003839 salts Chemical class 0.000 claims abstract description 57
- 238000002360 preparation method Methods 0.000 claims abstract description 25
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 307
- 229910052739 hydrogen Inorganic materials 0.000 claims description 151
- 239000001257 hydrogen Substances 0.000 claims description 149
- 125000000217 alkyl group Chemical group 0.000 claims description 129
- 229910052736 halogen Inorganic materials 0.000 claims description 109
- 150000002367 halogens Chemical class 0.000 claims description 101
- -1 (C1-C6)- Alkyl carbonyl epoxide Chemical class 0.000 claims description 87
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 82
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 76
- 229910052799 carbon Inorganic materials 0.000 claims description 58
- 238000000034 method Methods 0.000 claims description 49
- 150000002431 hydrogen Chemical group 0.000 claims description 47
- 125000003118 aryl group Chemical group 0.000 claims description 46
- 239000000126 substance Substances 0.000 claims description 46
- 230000002363 herbicidal effect Effects 0.000 claims description 45
- 239000004009 herbicide Substances 0.000 claims description 42
- 150000001412 amines Chemical class 0.000 claims description 38
- 239000000203 mixture Substances 0.000 claims description 38
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 35
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
- 125000001424 substituent group Chemical group 0.000 claims description 33
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
- 150000001721 carbon Chemical group 0.000 claims description 30
- 244000038559 crop plants Species 0.000 claims description 30
- 239000000460 chlorine Substances 0.000 claims description 29
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 28
- 125000003342 alkenyl group Chemical group 0.000 claims description 26
- 229910052801 chlorine Inorganic materials 0.000 claims description 26
- 125000003545 alkoxy group Chemical group 0.000 claims description 25
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 23
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 23
- 239000011737 fluorine Substances 0.000 claims description 23
- 229910052731 fluorine Inorganic materials 0.000 claims description 23
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 22
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 21
- 229910052760 oxygen Inorganic materials 0.000 claims description 20
- 125000006644 (C2-C6) haloalkynyl group Chemical group 0.000 claims description 19
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 17
- 125000002837 carbocyclic group Chemical group 0.000 claims description 17
- 125000000623 heterocyclic group Chemical group 0.000 claims description 17
- 230000001473 noxious effect Effects 0.000 claims description 17
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 claims description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 14
- 239000005864 Sulphur Substances 0.000 claims description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 13
- 229910052794 bromium Inorganic materials 0.000 claims description 13
- 125000006593 (C2-C3) alkynyl group Chemical group 0.000 claims description 12
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 11
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 11
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 125000006592 (C2-C3) alkenyl group Chemical group 0.000 claims description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 10
- 125000006519 CCH3 Chemical group 0.000 claims description 9
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 8
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 230000009261 transgenic effect Effects 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 7
- 239000012038 nucleophile Substances 0.000 claims description 7
- 230000002265 prevention Effects 0.000 claims description 7
- 125000001544 thienyl group Chemical group 0.000 claims description 7
- 125000006625 (C3-C8) cycloalkyloxy group Chemical group 0.000 claims description 6
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 6
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 6
- 125000000468 ketone group Chemical group 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 125000005914 C6-C14 aryloxy group Chemical group 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 150000001538 azepines Chemical class 0.000 claims description 5
- 125000001475 halogen functional group Chemical group 0.000 claims description 5
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 4
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims description 4
- 125000006553 (C3-C8) cycloalkenyl group Chemical group 0.000 claims description 4
- 125000005974 C6-C14 arylcarbonyl group Chemical group 0.000 claims description 4
- 125000005090 alkenylcarbonyl group Chemical group 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 125000006767 (C2-C6) haloalkynyloxy group Chemical group 0.000 claims description 3
- LJXPWUAAAAXJBX-UHFFFAOYSA-N 2-methylallyl radical Chemical compound [CH2]C(C)=C LJXPWUAAAAXJBX-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 claims description 3
- 239000003630 growth substance Substances 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 235000013311 vegetables Nutrition 0.000 claims description 3
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 2
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 2
- DBTDEFJAFBUGPP-UHFFFAOYSA-N Methanethial Chemical compound S=C DBTDEFJAFBUGPP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 2
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000006412 propinylene group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 3
- 150000002118 epoxides Chemical class 0.000 claims 3
- 125000003277 amino group Chemical class 0.000 claims 2
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims 1
- 125000005133 alkynyloxy group Chemical group 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- 150000002829 nitrogen Chemical class 0.000 claims 1
- PARWUHTVGZSQPD-UHFFFAOYSA-N phenylsilane Chemical compound [SiH3]C1=CC=CC=C1 PARWUHTVGZSQPD-UHFFFAOYSA-N 0.000 claims 1
- 239000002585 base Substances 0.000 description 154
- 241000196324 Embryophyta Species 0.000 description 79
- 230000000694 effects Effects 0.000 description 45
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 34
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 20
- 239000002253 acid Substances 0.000 description 20
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 19
- 150000003230 pyrimidines Chemical class 0.000 description 18
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 17
- 244000025254 Cannabis sativa Species 0.000 description 16
- 239000003795 chemical substances by application Substances 0.000 description 16
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 238000009333 weeding Methods 0.000 description 15
- 150000002148 esters Chemical class 0.000 description 14
- 108090000623 proteins and genes Proteins 0.000 description 14
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 13
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 235000011054 acetic acid Nutrition 0.000 description 12
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 description 12
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 12
- 239000012071 phase Substances 0.000 description 12
- 230000002829 reductive effect Effects 0.000 description 12
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 description 11
- 240000007594 Oryza sativa Species 0.000 description 11
- 235000007164 Oryza sativa Nutrition 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 235000009566 rice Nutrition 0.000 description 11
- 239000004563 wettable powder Substances 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 10
- 230000008859 change Effects 0.000 description 10
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 10
- 239000008187 granular material Substances 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- 238000005481 NMR spectroscopy Methods 0.000 description 9
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
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- 235000011684 Sorghum saccharatum Nutrition 0.000 description 9
- 230000012010 growth Effects 0.000 description 9
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 9
- 239000002689 soil Substances 0.000 description 9
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 8
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- IAJOBQBIJHVGMQ-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid Chemical compound CP(O)(=O)CCC(N)C(O)=O IAJOBQBIJHVGMQ-UHFFFAOYSA-N 0.000 description 7
- VYNOULHXXDFBLU-UHFFFAOYSA-N Cumyluron Chemical compound C=1C=CC=CC=1C(C)(C)NC(=O)NCC1=CC=CC=C1Cl VYNOULHXXDFBLU-UHFFFAOYSA-N 0.000 description 7
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- 238000009472 formulation Methods 0.000 description 7
- 150000002576 ketones Chemical class 0.000 description 7
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- 239000011591 potassium Substances 0.000 description 7
- 229910052700 potassium Inorganic materials 0.000 description 7
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 238000006443 Buchwald-Hartwig cross coupling reaction Methods 0.000 description 6
- NNYRZQHKCHEXSD-UHFFFAOYSA-N Daimuron Chemical compound C1=CC(C)=CC=C1NC(=O)NC(C)(C)C1=CC=CC=C1 NNYRZQHKCHEXSD-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
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- 239000011734 sodium Substances 0.000 description 6
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
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- JRQGDDUXDKCWRF-UHFFFAOYSA-M sodium;n-(2-methoxycarbonylphenyl)sulfonyl-4-methyl-5-oxo-3-propoxy-1,2,4-triazole-1-carboximidate Chemical compound [Na+].O=C1N(C)C(OCCC)=NN1C(=O)[N-]S(=O)(=O)C1=CC=CC=C1C(=O)OC JRQGDDUXDKCWRF-UHFFFAOYSA-M 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- LOQQVLXUKHKNIA-UHFFFAOYSA-N thifensulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C2=C(SC=C2)C(O)=O)=N1 LOQQVLXUKHKNIA-UHFFFAOYSA-N 0.000 description 1
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- WHLUQAYNVOGZST-UHFFFAOYSA-N tifenamil Chemical group C=1C=CC=CC=1C(C(=O)SCCN(CC)CC)C1=CC=CC=C1 WHLUQAYNVOGZST-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
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- 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
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- BQZXUHDXIARLEO-UHFFFAOYSA-N tribenuron Chemical compound COC1=NC(C)=NC(N(C)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 BQZXUHDXIARLEO-UHFFFAOYSA-N 0.000 description 1
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- DFFWZNDCNBOKDI-UHFFFAOYSA-N trinexapac Chemical compound O=C1CC(C(=O)O)CC(=O)C1=C(O)C1CC1 DFFWZNDCNBOKDI-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—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
-
- 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
-
- 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
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Abstract
本发明涉及通式(I)的化合物及其农业化学上可接受的盐、其制备方法以及其在植物保护领域中的用途。
Description
本发明涉及作物保护组合物的技术领域,特别是涉及用于选择性防治有用植物作物中和观赏园艺领域中的阔叶杂草和禾本科杂草,以及用于一般性防治植物生长具有破坏性的环境区域中的阔叶杂草和禾本科杂草的除草剂的技术领域。
更具体而言,本发明涉及取代的2-氨基-5-氧基烷基嘧啶衍生物、其制备方法及其用于防治有害植物的用途。
本发明式(I)的化合物在嘧啶的5位上具有氧基烷基,且在嘧啶的2位上具有部分氢化的双环取代基,该部分氢化的双环取代基通过胺连接在芳族体系的α位,其中所述嘧啶的4位和6位也可被取代,并且氧基烷基通过烷基与相邻位置的取代基一起可形成环。
二氨基嘧啶和单氨基嘧啶的除草作用是现有技术是已知的。
2,4-二氨基嘧啶及其在作物保护领域中的用途公开于例如文献EP0523533 A1、WO2010/076009 A1和WO 2010/076010 A1中。由US2010/0167934 A1已知含有在桥接和相邻碳原子上具有(1R,2S)构型的双环基团且同时具有除草作用的2,4-二氨基嘧啶。
其他二氨基嘧啶(即取代的呋喃并-/噻吩并环烷基氨基-2-嘧啶衍生物)公开于文献WO 2017/016914 A1中。除了2位上的氨基取代基外,这些呋喃并-/噻吩并环烷基氨基-2-嘧啶衍生物的嘧啶环在4位、5位和6位上可具有另外的氨基。通过权利要求1所涵盖的化合物,本申请的主题与由WO 2017/016914 A1已知的化合物不同之处在于稠和的苯环。相反,WO 2017/016914 A1中已知的化合物具有稠和的噻吩环。表4a和4b中的比较数据总结了该区别所带来的除草活性的改善。
具有除草作用的单氨基嘧啶(即5-氨基嘧啶衍生物)公开于例如文献WO 2013/144187 A1中。具有除草作用的其他单氨基嘧啶(即2-氨基-5-酮嘧啶衍生物)公开于文献WO2016/001118 A1中。表3a和3b中总结的对比数据证明了本发明化合物所带来的除草活性的改善。
其他2-氨基嘧啶衍生物(即2-氨基-5-酮肟-嘧啶衍生物)为申请号为PCT/EP2016/081655的尚未公开的申请的主题。在公开之后,该申请将是根据欧洲专利公约第54条3款关于本申请的文件。
然而,已知的嘧啶衍生物在各种有用植物作物中作为选择性除草剂用于防治有害植物或作为植物生长调节剂的使用通常需要高成本的施用率或对有用植物造成不想要的损害。另外,在许多情况下,活性化合物的使用由于相对高昂的生产成本而不经济。
因此,希望提供可用作除草剂或植物生长调节剂且与现有技术已知的体系相比具有某些优点的基于嘧啶衍生物的替代性化学活性成分。
本发明的一个目的是提供可用作除草剂或植物生长调节剂的替代性嘧啶衍生物,其具有令人满意的除草作用并对有害植物具有广谱活性和/或在有用植物作物中具有高的选择性。
另外,与现有技术已知的嘧啶衍生物相比,替代性嘧啶衍生物显示出更好的性质,特别是对有害植物更好的除草活性,对有害植物更广谱的作用和/或在有用植物作物中更高的选择性。
该目的通过权利要求1所要求保护的特定取代的式(I)的2-氨基-5-氧基烷基嘧啶衍生物而实现,特别是由于嘧啶环5位上的取代,式(I)的2-氨基-5-氧基烷基嘧啶衍生物可有利地用作除草剂以及植物生长调节剂。嘧啶环5位上的取代涉及包含基团R3-O-C、R1a和R1b的基团。
因此,本发明提供了式(I)的化合物及其农业化学上可接受的盐
其中
R1a选自
-氢、氰基、CO(O)H、C(O)NH2;
-(C1-C6)-烷基、(C1-C6)-卤代烷基、(C1-C6)-烷基羰基-(C1-C4)-烷基;
-(C1-C6)-烷氧基羰基-(C1-C6)-烷基、(C1-C6)-卤代烷氧基羰基-(C1-C6)-烷基、(C1-C6)-烷氧基羰基-(C1-C6)-卤代烷基、(C1-C6)-卤代烷氧基羰基-(C1-C6)-卤代烷基;
-(C2-C6)-烯基、(C2-C6)-卤代烯基;
-(C2-C6)-炔基、(C2-C6)-卤代炔基;
-(C6-C14)-芳基,其芳基部分在每种情况下可被卤素、(C1-C6)-烷基和/或(C1-C6)-卤代烷基取代;
-吡啶基,其在每种情况下可被卤素、(C1-C6)-烷基和/或(C1-C6)-卤代烷基取代;
-噻吩基,其在每种情况下可被卤素、(C1-C6)-烷基和/或(C1-C6)-卤代烷基取代;
-(C6-C14)-芳基-(C1-C6)-烷基,其芳基部分在每种情况下可被卤素、(C1-C6)-烷基和/或(C1-C6)-卤代烷基取代;
-氨基羰基-(C1-C6)-烷基;
-(C1-C6)-烷氧基-(C1-C6)-烷基;
-(C3-C8)-环烷基,其环烷基可为未取代的或被(C1-C6)-烷基和/或卤素单取代或多取代;(C3-C8)-环烷基-(C1-C6)-烷基、(C3-C8)-环烷基-(C1-C6)-卤代烷基;
-(C3-C8)-环烯基、(C3-C8)-环烯基-(C1-C6)-烷基、(C3-C8)-环烯基-(C1-C6)-卤代烷基;
-羟基-(C1-C6)-烷基、氨基-(C1-C6)-烷基、氰基-(C1-C6)-烷基;
-(C1-C6)-烷基磺酰基-(C1-C6)-烷基、(C1-C6)-烷硫基-(C1-C6)-烷基、(C1-C6)-烷基亚磺酰基-(C1-C6)-烷基、(C1-C6)-卤代烷基磺酰基-(C1-C6)-烷基、(C1-C6)-卤代烷硫基-(C1-C6)-烷基、(C1-C6)-卤代烷基亚磺酰基-(C1-C6)-烷基、(C1-C6)-烷基磺酰基-(C1-C6)-卤代烷基、(C1-C6)-烷硫基-(C1-C6)-卤代烷基、(C1-C6)-烷基亚磺酰基-(C1-C6)-卤代烷基、(C1-C6)-卤代烷基磺酰基-(C1-C6)-卤代烷基、(C1-C6)-卤代烷硫基-(C1-C6)-卤代烷基、(C1-C6)-卤代烷基亚磺酰基-(C1-C6)-卤代烷基;
R1b选自
-氰基、C(O)OH、C(O)NH2;
-(C1-C6)-烷基、(C1-C6)-卤代烷基、(C1-C6)-烷基羰基-(C1-C4)-烷基;
-(C1-C6)-烷氧基羰基-(C1-C6)-烷基、(C1-C6)-卤代烷氧基羰基-(C1-C6)-烷基、(C1-C6)-烷氧基羰基-(C1-C6)-卤代烷基、(C1-C6)-卤代烷氧基羰基-(C1-C6)-卤代烷基;
-(C2-C6)-烯基、(C2-C6)-卤代烯基;
-(C2-C6)-炔基、(C2-C6)-卤代炔基;
-(C6-C14)-芳基,其芳基部分在每种情况下可被卤素、(C1-C6)-烷基和/或(C1-C6)-卤代烷基取代;
-吡啶基,其在每种情况下可被卤素、(C1-C6)-烷基和/或(C1-C6)-卤代烷基取代;
-噻吩基,其在每种情况下可被卤素、(C1-C6)-烷基和/或(C1-C6)-卤代烷基取代;
-(C6-C14)-芳基-(C1-C6)-烷基,其芳基部分在每种情况下可被卤素、(C1-C6)-烷基和/或(C1-C6)-卤代烷基取代;
-氨基羰基-(C1-C6)-烷基;
-(C1-C6)-烷氧基-(C1-C6)-烷基;
-(C3-C8)-环烷基,其环烷基可为未取代的或被(C1-C6)-烷基和/或卤素单取代或多取代;(C3-C8)-环烷基-(C1-C6)-烷基、(C3-C8)-环烷基-(C1-C6)-卤代烷基;
-(C3-C8)-环烯基、(C3-C8)-环烯基-(C1-C6)-烷基、(C3-C8)-环烯基-(C1-C6)-卤代烷基;
-羟基-(C1-C6)-烷基、氨基-(C1-C6)-烷基、氰基-(C1-C6)-烷基;
-(C1-C6)-烷基磺酰基-(C1-C6)-烷基、(C1-C6)-烷硫基-(C1-C6)-烷基、(C1-C6)-烷基亚磺酰基-(C1-C6)-烷基、(C1-C6)-卤代烷基磺酰基-(C1-C6)-烷基、(C1-C6)-卤代烷硫基-(C1-C6)-烷基、(C1-C6)-卤代烷基亚磺酰基-(C1-C6)-烷基、(C1-C6)-烷基磺酰基-(C1-C6)-卤代烷基、(C1-C6)-烷硫基-(C1-C6)-卤代烷基、(C1-C6)-烷基亚磺酰基-(C1-C6)-卤代烷基、(C1-C6)-卤代烷基磺酰基-(C1-C6)-卤代烷基、(C1-C6)-卤代烷硫基-(C1-C6)-卤代烷基、(C1-C6)-卤代烷基亚磺酰基-(C1-C6)-卤代烷基;
其中,如果R1a不代表氢,则R1a通过化学键与R1b相连,使得它们与这两个基团所连接的碳一起形成饱和或不饱和的3至7元的碳环或杂环,该碳环或杂环为未取代的或被一个或多个取代基取代,所述取代基选自(C1-C6)-烷基、(C1-C6)-卤代烷基、(C3-C8)-环烷基、螺环-(C3-C8)-环烷基;
R2a和R2b在每种情况下彼此独立地选自
-氢、卤素、羟基、氰基、C(O)OH、C(O)NH2;
-(C1-C6)-烷基、(C1-C6)-卤代烷基、(C1-C6)-烷基羰基、(C1-C6)-卤代烷基羰基、(C1-C6)-烷基羰基氧基、(C1-C6)-卤代烷基羰基氧基、(C1-C6)-烷基羰基-(C1-C4)-烷基;
-(C1-C6)-烷氧基、(C1-C6)-卤代烷氧基、(C1-C6)-烷氧基羰基、(C1-C6)-卤代烷氧基羰基、(C1-C6)-烷氧基羰基-(C1-C6)-烷基、(C1-C6)-卤代烷氧基羰基-(C1-C6)-烷基、(C1-C6)-烷氧基羰基-(C1-C6)-卤代烷基、(C1-C6)-卤代烷氧基羰基-(C1-C6)-卤代烷基;
-(C2-C6)-烯基、(C2-C6)-卤代烯基、(C2-C6)-烯基羰基、(C2-C6)-卤代烯基羰基、(C2-C6)-烯基氧基、(C2-C6)-卤代烯基氧基、(C2-C6)-烯基氧基羰基、(C2-C6)-卤代烯基氧基羰基;
-(C2-C6)-炔基、(C2-C6)-卤代炔基、(C2-C6)-炔基羰基、(C2-C6)-卤代炔基羰基、(C2-C6)-炔基氧基、(C2-C6)-卤代炔基氧基、(C2-C6)-炔基氧基羰基、(C2-C6)-卤代炔基氧基羰基、三-(C1-C6)-烷基甲硅烷基-(C2-C6)-炔基、二-(C1-C6)-烷基甲硅烷基-(C2-C6)-炔基、单-(C1-C6)-烷基甲硅烷基-(C2-C6)-炔基、苯基甲硅烷基-(C2-C6)-
炔基;
-(C6-C14)-芳基、(C6-C14)-芳基氧基、(C6-C14)-芳基羰基和(C6-C14)-芳基氧基羰基,其各自芳基部分可被卤素、(C1-C6)-烷基和/或(C1-C6)-卤代烷基取代;
-(C6-C14)-芳基-(C1-C6)-烷基、(C6-C14)-芳基-(C1-C6)-烷氧基、(C6-C14)-芳基-(C1-C6)-烷基羰基、(C6-C14)-芳基-(C1-C6)-烷基羰基氧基、(C6-C14)-芳基-(C1-C6)-烷氧基羰基、(C6-C14)-芳基-(C1-C6)-烷氧基羰基氧基;
-氨基羰基-(C1-C6)-烷基、二-(C1-C6)-烷基氨基羰基-(C1-C6)-烷基;
-N-((C1-C6)-卤代烷酰基)-氨基羰基、单-((C1-C6)-芳基)-氨基羰基、二-((C1-C6)-芳基)-氨基羰基;
-(C1-C6)-烷氧基-(C1-C6)-烷基、(C1-C6)-烷氧基-(C1-C6)-烷氧基、(C1-C6)-烷氧基羰基-(C1-C6)-烷氧基;
-(C3-C8)-环烷基,其环烷基可为未取代的或被(C1-C6)-烷基和/或卤素单取代或多取代;(C3-C8)-环烷氧基、(C3-C8)-环烷基-(C1-C6)-烷基、(C3-C8)-环烷基-(C1-C6)-卤代烷基、(C3-C8)-环烷基-(C1-C6)-烷氧基、(C3-C8)-环烷基-(C1-C6)-卤代烷氧基、(C3-C8)-环烷基羰基、(C3-C8)-环烷氧基羰基、(C3-C8)-环烷基-(C1-C6)-烷基羰基、(C3-C8)-环烷基-(C1-C6)-卤代烷基羰基、(C3-C8)-环烷基-(C1-C6)-烷氧基羰基、(C3-C8)-环烷基-(C1-C6)-卤代烷氧基羰基、(C3-C8)-环烷基羰基氧基、(C3-C8)-环烷氧基羰基氧基、(C3-C8)-环烷基-(C1-C6)-烷基羰基氧基、(C3-C8)-环烷基-(C1-C6)-卤代烷基羰基氧基、(C3-C8)-环烷基-(C1-C6)-烷氧基羰基氧基、(C3-C8)-环烷基-(C1-C6)-卤代烷氧基羰基氧基;
-(C3-C8)-环烯基、(C3-C8)-环烯基氧基、(C3-C8)-环烯基-(C1-C6)-烷基、(C3-C8)-环烯基-(C1-C6)-卤代烷基、(C3-C8)-环烯基-(C1-C6)-烷氧基、(C3-C8)-环烯基-(C1-C6)-卤代烷氧基、(C3-C8)-环烯基羰基、(C3-C8)-环烯基氧基羰基、(C3-C8)-环烯基-(C1-C6)-烷基羰基、(C3-C8)-环烯基-(C1-C6)-卤代烷基羰基、(C3-C8)-环烯基-(C1-C6)-烷氧基羰基、(C3-C8)-环烯基-(C1-C6)-卤代烷氧基羰基、(C3-C8)-环烯基羰基氧基、(C3-C8)-环烯氧基羰基氧基、(C3-C8)-环烯基-(C1-C6)-烷基羰基氧基、(C3-C8)-环烯基-(C1-C6)-卤代烷基羰基氧基、(C3-C8)-环烯基-(C1-C6)-烷氧基羰基氧基、(C3-C8)-环烯基-(C1-C6)-卤代烷氧基羰基氧基;
-羟基-(C1-C6)-烷基、羟基-(C1-C6)-烷氧基、氰基-(C1-C6)-烷氧基、氰基-(C1-C6)-烷基;
-(C1-C6)-烷基磺酰基、(C1-C6)-烷硫基、(C1-C6)-烷基亚磺酰基、(C1-C6)-卤代烷基磺酰基、(C1-C6)-卤代烷硫基、(C1-C6)-卤代烷基亚磺酰基、(C1-C6)-烷基磺酰基-(C1-C6)-烷基、(C1-C6)-烷硫基-(C1-C6)-烷基、(C1-C6)-烷基亚磺酰基-(C1-C6)-烷基、(C1-C6)-卤代烷基磺酰基-(C1-C6)-烷基、(C1-C6)-卤代烷硫基-(C1-C6)-烷基、(C1-C6)-卤代烷基亚磺酰基-(C1-C6)-烷基、(C1-C6)-烷基磺酰基-(C1-C6)-卤代烷基、(C1-C6)-烷硫基-(C1-C6)-卤代烷基、(C1-C6)-烷基亚磺酰基-(C1-C6)-卤代烷基、(C1-C6)-卤代烷基磺酰基-(C1-C6)-卤代烷基、(C1-C6)-卤代烷硫基-(C1-C6)-卤代烷基、(C1-C6)-卤代烷基亚磺酰基-(C1-C6)-卤代烷基、(C1-C6)-烷基磺酰基氧基、(C1-C6)-卤代烷基磺酰基氧基、(C1-C6)-烷基硫代羰基、(C1-C6)-卤代烷基硫代羰基、(C1-C6)-烷基硫代羰基氧基、(C1-C6)-卤代烷基硫代羰基氧基、(C1-C6)-烷硫基-(C1-C6)-烷基、(C1-C6)-烷硫基-(C1-C6)-烷氧基、(C1-C6)-烷硫基-(C1-C6)-烷基羰基、(C1-C6)-烷硫基-(C1-C6)-烷基羰基氧基、(C4-C14)-芳基磺酰基、(C6-C14)-芳基硫基、(C6-C14)-芳基亚磺酰基、(C3-C8)-环烷硫基、(C3-C8)-烯基硫基、(C3-C8)-环烯基硫基和(C3-C6)-炔基硫基;
R3选自
-氢;
-(C1-C6)-烷基羰基、(C1-C6)-卤代烷基羰基;
-(C2-C6)-烯基羰基、(C1-C6)-卤代烯基羰基;
-(C2-C6)-炔基羰基、(C1-C6)-卤代炔基羰基;
-(C6-C14)-芳基羰基,其芳基部分在每种情况下可被卤素、(C1-C6)-烷基和/或(C1-C6)-卤代烷基取代;
-氨基羰基、[(C1-C6)-烷基氨基]羰基、[二-(C1-C6)-烷基氨基]羰基;
-(C1-C6)-烷氧基羰基、(C2-C6)-烯基氧基羰基、(C2-C6)-炔基氧基羰基;
-(C1-C6)-三烷基甲硅烷基;
-(C1-C6)-烷基磺酰基、(C1-C6)-卤代烷基磺酰基;
-(C6-C14)-芳基磺酰基,其芳基部分在每种情况下可被卤素、(C1-C6)-烷基和/或(C1-C6)-卤代烷基取代;
-(C1-C6)-烷基、(C1-C6)-卤代烷基、(C1-C6)-烷基羰基-(C1-C4)-烷基;-(C2-C6)-烯基、(C2-C6)-卤代烯基;
-(C2-C6)-炔基、(C2-C6)-卤代炔基、三-(C1-C6)-烷基甲硅烷基-(C2-C6)-炔基、二-(C1-C6)-烷基甲硅烷基-(C2-C6)-炔基、单-(C1-C6)-烷基甲硅烷基-(C2-C6)-炔基、苯基甲硅烷基-(C2-C6)-炔基;
-(C1-C6)-烷氧基羰基-(C1-C6)-烷基、(C1-C6)-卤代烷氧基羰基-(C1-C6)-烷基、(C1-C6)-烷氧基羰基-(C1-C6)-卤代烷基、(C1-C6)-卤代烷氧基羰基-(C1-C6)-卤代烷基;
-(C6-C14)-芳基,其芳基部分在每种情况下可被卤素、(C1-C6)-烷基和/或(C1-C6)-卤代烷基取代;
-(C2-C14)-杂芳基,其杂芳基部分在每种情况下可被卤素、(C1-C6)-烷基和/或(C1-C6)-卤代烷基取代;
-(C6-C14)-芳基-(C1-C6)-烷基,其芳基部分在每种情况下可被卤素、(C1-C6)-烷基和/或(C1-C6)-卤代烷基取代;
-氨基羰基-(C1-C6)-烷基;
-(C1-C6)-烷氧基-(C1-C6)-烷基;
-(C3-C8)-环烷基,其环烷基可被(C1-C6)-烷基和/或卤素单取代或多取代;
-(C3-C8)-环烷基-(C1-C6)-烷基、(C3-C8)-环烷基-(C1-C6)-卤代烷基;
-(C3-C8)-环烯基-(C1-C6)-烷基、(C3-C8)-环烯基-(C1-C6)-卤代烷基、羟基-(C1-C6)-烷基、氰基-(C1-C6)-烷基;
-(C1-C6)-烷基磺酰基-(C1-C6)-烷基、(C1-C6)-烷硫基-(C1-C6)-烷基、(C1-C6)-烷基亚磺酰基-(C1-C6)-烷基、(C1-C6)-卤代烷基磺酰基-(C1-C6)-烷基、(C1-C6)-卤代烷硫基-(C1-C6)-烷基、(C1-C6)-卤代烷基亚磺酰基-(C1-C6)-烷基、(C1-C6)-烷基磺酰基-(C1-C6)-卤代烷基、(C1-C6)-烷硫基-(C1-C6)-卤代烷基、(C1-C6)-烷基亚磺酰基-(C1-C6)-卤代烷基、(C1-C6)-卤代烷基磺酰基-(C1-C6)-卤代烷基、(C1-C6)-卤代烷硫基-(C1-C6)-卤代烷基、(C1-C6)-卤代烷基亚磺酰基-(C1-C6)-卤代烷基;
R4和R5各自彼此独立地选自氢、(C1-C6)-烷基、(C1-C6)-卤代烷基、羟基、(C1-C6)-烷氧基和(C1-C6)-卤代烷氧基;或者基团R4和R5与它们所连接的碳原子一起形成三至七元环;
R6和R7各自彼此独立地选自氢、(C1-C6)-烷基、(C1-C6)-卤代烷基、(C1-C6)-烷氧基、(C1-C6)-卤代烷氧基、(C6-C14)-芳基、(C6-C14)-芳基氧基、(C6-C14)-芳基羰基和(C6-C14)-芳基氧基羰基;或者基团R6和R7一起形成可含有一个或多个氧和/或硫原子的(C1-C7)-亚烷基基团,其中(C1-C7)-亚烷基基团可被卤素单取代或多取代且各卤素取代基可相同或不同;
n代表顺序号0、1或2;
R8、R9、R10和R11各自彼此独立地选自氢、卤素、氰基、C(O)OH、C(O)NH2、(C1-C6)-烷基、(C1-C6)-烷基羰基、(C1-C6)-烷基氧基羰基、(C1-C6)-烷基氨基羰基、(C1-C6)-二烷基氨基羰基、(C1-C6)-卤代烷基、(C1-C6)-烷氧基、(C1-C6)-卤代烷氧基、(C2-C6)-烯基、(C2-C6)-炔基、(C2-C6)-卤代炔基、(C2-C6)-炔基羰基、(C2-C6)-卤代炔基羰基、(C2-C6)-炔基氧基、(C2-C6)-卤代炔基氧基、(C2-C6)-炔基氧基羰基、(C2-C6)-卤代炔基氧基羰基、(C6-C14)-芳基和硝基,其中基团R9和R10可通过-O-CH2-O-基团连接而形成环;
X代表化学键、CH2、O、S、羰基、NH、CR12R13、NR14、CH2O或CH2S,其中最后提及的两个基团中的碳原子与芳族部分相连且杂原子O或S与部分氢化的胺部分相连;
R12和R13各自彼此独立地选自氢、(C1-C6)-烷基和(C1-C6)-卤代烷基;并且
R14选自氢、(C1-C6)-烷基和(C1-C6)-卤代烷基。
本发明式(I)的2-氨基-5-氧基烷基嘧啶衍生物与现有技术已知的二氨基嘧啶衍生物(如由文献EP 0523533 A1、WO 2010/076009 A1和WO2010/076010 A1已知的具有2,4-二氨基嘧啶结构的除草剂)不同之处在于与嘧啶环的环原子直接相连的氨基的数量。下文表1和2中的对比数据涉及由WO 2010/076010 A1已知的二氨基嘧啶衍生物。
因此,在本发明式(I)的单氨基嘧啶衍生物中,两个基团R2a和R2b不代表氨基,即R2a和R2b不通过氮原子与嘧啶环相连。本发明的2-氨基-5-氧基烷基嘧啶仅被一个氨基取代,并且该氨基将嘧啶环与双环取代基彼此连接。
相比之下,本发明式(I)的2-氨基-5-氧基烷基嘧啶与已知的具有仅一个氨基取代基的嘧啶(单氨基嘧啶)(例如来自文献WO 2013/144187 A1)不同之处在于氨基在2位(即,在形成嘧啶环的一部分的两个氮原子之间),而不是在5位。
在本发明式(I)的单氨基嘧啶中,嘧啶的2位的氨基具有部分氢化的双环取代基,所述部分氢化的双环取代基与在芳族体系的α位的氨基相连。
文献WO 2016/001118 A1中公开的上述2-氨基-5-酮嘧啶衍生物,以及2-氨基-5-酮肟嘧啶衍生物(其为申请号为PCT/EP2016/081655的上述尚未公开的申请的主题)与本发明式(I)的单氨基嘧啶的嘧啶环上的氨基的数目和位置相同。
然而,本发明式(I)的单氨基嘧啶与上述两个2-氨基嘧啶衍生物的不同之处在于,它们在5位没有酮基(羰基)或酮肟结构单元。也就是说,本发明化合物的5位上的包含基团R3-O-C、R1a和R1b并一起形成氧基烷基的结构要素的基团的特征在于,它们没有羰基且没有酮肟结构单元。下文表3和4中的对比数据涉及由WO 2016/001118 A1已知的单氨基嘧啶衍生物。
与WO 2010/076010 A1中类似的二氨基嘧啶和由WO 2016/001118已知的单氨基嘧啶相比,本发明化合物具有出乎意料地良好的除草活性,其已通过下文表4中进行对比的比较对(comparative pairs)得到证实。
表1(苗前法)和表2(苗后法)中比较的除草功效证实了,与现有技术已知的对照化合物相比,本发明的化合物1.4和1.6以及1.7和1.2具有良好的活性谱。
在嘧啶的4位,本发明的对照化合物为未取代的(4-H)或被不同于氨基的取代基如甲基(4-Me)取代。
相比之下,由WO 2010/076010 A1已知的二氨基嘧啶在嘧啶的4位具有另外的氨基。
本发明化合物的特征在于出人意料地良好的活性谱。
表3a(苗前法)和表3b(苗后法)中比较的除草效果证实了,与现有技术已知的对照化合物相比,本发明的化合物1.6、1.7和1.8具有良好的活性谱。
本发明的对照化合物在嘧啶环的5位具有一个羟基烷基(5-羟基烷基)。
相比之下,由WO 2016/001118 A1已知的单氨基嘧啶在嘧啶的5位具有酮基(5-酮嘧啶)。
本发明化合物的特征在于出人意料地良好的活性谱。
除了良好的功效特性和/或良好的作物植物相容性外,式(I)的化合物还由于其廉价的制备而备受瞩目,因为本发明的物质可以由经济且易得的前体通过经济的方法来制备。因此可以免除使用昂贵且不易得的中间体。
下文是各单独取代基的优选、特别优选、非常特别优选的定义的描述。下文未指定的通式(I)的其他取代基具有上文给出的定义。这同样适用于顺序号n,即,在下文的实施方案中,顺序号n为0、1或2。
表4a(苗前法)和表4b(苗后法)中比较的除草功效证实了,与由WO 2017/016914A1已知的对照化合物相比,本发明的化合物1.48和1.52具有出乎意料地良好的活性谱。
本发明的第一个实施方案包含通式(I)的化合物,其中
R1a优选选自
-氢、氰基;
-(C1-C6)-烷基、(C1-C6)-卤代烷基、(C2-C6)-烯基、(C2-C6)-卤代烯基、(C2-C6)-炔基、(C2-C6)-卤代炔基;
-(C3-C8)-环烷基,其环烷基可未被取代或被(C1-C6)-烷基和/或卤素单取代或多取代;
R1a特别优选选自
-氢;
-(C1-C3)-烷基、(C1-C3)-卤代烷基、(C2-C3)-烯基、(C2-C3)-炔基;
R1a非常特别优选代表氢、CH3、CH2CH3、CF3、C(H)=CH2或C≡CH;
R1a最优选代表氢、CH3或CH2CH3。
本发明的第二个实施方案包含通式(I)的化合物,其中
R1b优选选自
-氰基、C(O)OH、C(O)NH2;
-(C1-C6)-烷基、(C1-C6)-卤代烷基、(C1-C6)-烷基羰基-(C1-C4)-烷基;
-(C1-C6)-烷氧基羰基-(C1-C6)-烷基、(C2-C6)-烯基、(C2-C6)-卤代烯基;
-(C2-C6)-炔基、(C2-C6)-卤代炔基;
-(C6-C14)-芳基,其芳基部分在每种情况下可被卤素、(C1-C6)-烷基和/或(C1-C6)-卤代烷基取代;
-吡啶基,其在每种情况下可被卤素、(C1-C6)-烷基和/或(C1-C6)-卤代烷基取代;
-噻吩基,其在每种情况下可被卤素、(C1-C6)-烷基和/或(C1-C6)-卤代烷基取代;
-(C6-C14)-芳基-(C1-C6)-烷基,其芳基部分在每种情况下可被卤素、(C1-C6)-烷基和/或(C1-C6)-卤代烷基取代;
-(C3-C8)-环烷基,其环烷基可为未取代的或被(C1-C6)-烷基和/或卤素单取代或多取代;(C3-C8)-环烷基-(C1-C6)-烷基、(C3-C8)-环烷基-(C1-C6)-卤代烷基;
-(C3-C8)-环烯基、(C3-C8)-环烯基-(C1-C6)-烷基、(C3-C8)-环烯基-(C1-C6)-卤代烷基;
-氰基-(C1-C6)-烷基;
-(C1-C6)-烷基磺酰基-(C1-C6)-烷基、(C1-C6)-烷硫基-(C1-C6)-烷基、(C1-C6)-烷基亚磺酰基-(C1-C6)-烷基;
R1b特别优选选自
-氰基;
-(C1-C4)-烷基、(C1-C4)-卤代烷基;
-(C1-C3)-烷氧基羰基甲基、(C2-C4)-烯基、(C2-C4)-卤代烯基;
-(C2-C4)-炔基、(C2-C4)-卤代炔基;
-苯基,其芳基部分可被卤素和/或甲基取代;
-CH2-苯基(苄基),其芳基部分可被卤素和/或甲基取代;
-(C3-C6)-环烷基,其环烷基可为未取代的或被甲基和/或卤素单取代或多取代;
R1b非常特别优选代表氰基、CH3、CH2CH3、CH2CH(CH3)2、CF3、(C1-C2)-烷氧基羰基甲基、C(H)=CH2、C(H)=C(CH3)2、(CH2)2CH=CH2、C≡CH、C≡CCH3、苯基、CH2-苯基(苄基)或环丙基;
R1b最优选选自氰基、CH3、CH2CH3、CF3、C(H)=CH2、C≡CH、C≡CCH3;
本发明的第三个实施方案包含通式(I)的化合物,其中
如果R1a不代表氢,则R1a优选通过化学键与R1b相连,使得它们与这两个基团所连接的碳一起形成饱和的3至6元碳环,该碳环为未取代的或被一个或多个选自甲基、三氟甲基、环丙基的取代基取代;
如果R1a不代表氢,则R1a特别优选通过化学键与R1b相连,使得它们与这两个基团所连接的碳一起形成饱和的3至6元碳环,该碳环为未取代的或被一个或多个甲基取代,特别优选其中环单元各自由CH2单元形成的未取代的3至6元碳环;
如果R1a不代表氢,则R1a非常特别优选通过化学键与R1b相连,使得它们与这两个基团所连接的碳一起形成饱和的3元碳环,该碳环为未取代的或被甲基取代;
如果R1a不代表氢,则R1a最优选通过化学键与R1b连接,使得它们与这两个基团所连接的碳一起形成饱和的3元碳环,该碳环为未取代的;
本发明的第四个实施方案包含通式(I)的化合物,其中
R2a和R2b优选各自彼此独立地选自氢、(C1-C6)-烷基、(C1-C6)-卤代烷基、(C1-C6)-烷氧基、(C1-C6)-烷氧基-(C1-C6)-烷基、(C3-C8)-环烷基、(C3-C8)-环烷基-(C1-C6)-烷基和(C3-C8)-环烷基-(C1-C6)-卤代烷基,其中环烷基在每种情况下为未取代的或被(C1-C6)-烷基和/或卤素取代;
R2a和R2b特别优选各自彼此独立地选自氢、(C1-C6)-烷基、(C1-C6)-卤代烷基、(C1-C3)-烷氧基、(C1-C3)-烷氧基-(C1-C3)-烷基和(C3-C6)-环烷基;
R2a和R2b非常特别优选各自彼此独立地选自氢、CH3、CH2CH3、CH(CH3)2、CF3、CF2H、CF2Cl、CH(CH3)F、C(CH3)2F、环丙基和CH2OCH3;
R2a和R2b最优选各自彼此独立地选自氢、CH3、CH(CH3)F和CF2H;其中极优选R2a选自氢、CH3、CH(CH3)F和CF2H且R2b代表氢的组合。
本发明的第五个实施方案包含通式(I)的化合物,其中
R3优选选自
-氢;
-(C1-C3)-烷基羰基、(C1-C3)-卤代烷基羰基;
-苯基羰基,其芳基部分在每种情况下可被卤素和/或甲基取代;
-(C1-C6)-烷基、(C1-C6)-卤代烷基;
-(C2-C6)-烯基、CH(CH3)(C2-C3)-烯基、(C2-C6)-卤代烯基;
-(C2-C6)-炔基、CH(CH3)(C2-C3)-炔基、(C2-C6)-卤代炔基;
-(C1-C3)-烷氧基羰基-(C1-C3)-烷基;
-苯基-(C1-C3)-烷基,其芳基部分在每种情况下可被卤素和/或甲基取代;
-(C1-C3)-烷氧基-(C1-C3)-烷基;
-(C4-C6)-芳基,其芳基部分在每种情况下可被卤素取代;
-(C1-C3)-三烷基甲硅烷基;
R3特别优选选自
-氢;
-(C1-C4)-烷基羰基;
-苯基羰基(苯甲酰基);
-(C1-C3)-烷基;
-CH2(C2-C3)-烯基、CH(CH3)(C2-C3)-烯基;
-CH2(C2-C3)-炔基、CH(CH3)(C2-C3)-炔基;
-(C1-C3)-烷氧基羰基甲基;
-CH2-苯基(苄基);
-CH2(4-F-苯基);
-Si(CH3)3;
其中
R3特别优选选自
-氢;
-(C1-C3)-烷基,
-CH2(C2-C3)-烯基,
-CH2(C2-C3)-炔基,
-CH(CH3)(C2-C3)-烯基,
-CH(CH3)(C2-C3)-炔基,
-(C1-C2)-烷氧基羰基甲基,
R3最优选选自
-氢;
-CH3、CH2CH3;
-CH2CH=CH2、CH2C(CH3)=CH2、CH2CH=CHCH3;
-CH2C≡CH、CH2C≡CCH3;
-CH(CH3)CH=CH2;
-CH(CH3)C≡CH和
-CH2C(O)OCH3,其中
上述R3又特别优选代表氢或CH3,并且
R3极优选代表氢。
本发明的第六个实施方案包含通式(I)的化合物,其中
R4和R5优选各自彼此独立地选自氢、羟基、(C1-C6)-烷基、(C1-C6)-烷基苯基和(C1-C6)-烷氧基;
R4和R5特别优选各自彼此独立地选自氢、(C1-C6)-烷基和(C1-C6)-烷氧基;
R4和R5非常特别优选各自彼此独立地选自氢、(C1-C3)-烷基、(C1-C6)-烷氧基;
R4和R5最优选各自彼此独立地代表氢或甲基。
在该第六个实施方案中,尤其优选R4和R5基团中的至少一个代表氢。换言之,在每种情况下,当R4和R5基团中至少一个代表氢而R4和R5基团中另外一个不代表氢时,即尤其为(C1-C6)-烷基,优选甲基(CH3)。
本发明的第七个实施方案包含通式(I)的化合物,其中
R6和R7优选彼此独立地选自氢、(C1-C6)-烷基和(C6-C14)-芳基;
R6和R7特别优选彼此独立地选自氢、甲基和苯基;
R6和R7非常特别优选各自代表氢或甲基;
R6和R7最优选代表氢。
本发明的第八个实施方案包含通式(I)化合物,其中
R8优选选自氢、卤素、氰基、CO(O)H、(C1-C6)-烷基、(C1-C6)-烷氧基、(C1-C6)-烷氧基羰基和(C6-C14)-芳基;
R8特别优选选自氢、卤素、氰基、CO(O)H、(C1-C3)-烷基、(C1-C3)-烷氧基、(C1-C3)-烷氧基羰基和(C6-C8)-芳基;
R8非常特别优选选自氢、氟、氯、CH3、甲氧基羰基和苯基;
R8最优选代表氢或CH3。
本发明的第九个实施方案包含通式(I)的化合物,其中
R9优选选自氢、卤素、(C1-C6)-烷基和(C1-C6)-烷氧基;
R9特别优选选自氢、氯、氟和(C1-C3)-烷氧基;
R9非常特别优选选自氢、氟、氯和甲氧基;
R9最优选代表氢。
本发明的第十个实施方案包含通式(I)的化合物,其中
R10优选选自氢、卤素、氰基、氨基羰基、羟基羰基、(C1-C6)-烷基、(C1-C6)-卤代烷基、(C1-C6)-烷氧基、(C2-C6)-烯基、(C2-C6)-炔基、(C1-C6)-烷基-(C2-C6)-炔基、羟基-(C1-C6)-烷基-(C2-C6)-炔基、(C1-C6)-烷氧基-(C2-C6)-炔基和芳基-(C2-C6)-炔基;
R10特别优选选自氢、氟、氯、溴、碘、氰基、甲氧基(OCH3)、(C1-C3)-烷基、(C1-C3)-卤代烷基、(C1-C3)-烷氧基、(C2-C4)-烯基、(C2-C4)-炔基、(C1-C3)-烷基-(C2-C4)-炔基、羟基-(C1-C3)-烷基-(C2-C4)-炔基、(C1-C3)-烷氧基-(C2-C4)-炔基和苯基-(C2-C4)-炔基;
R10非常特别优选选自氢、氟、氯、溴、碘、氰基、甲基、C≡CH和C≡CCH3;
R10最优选代表氢或CH3。
本发明的第十一个实施方案包含通式(I)的化合物,其中
R11优选选自氢和(C1-C6)-烷基;
R11特别优选选自氢和(C1-C4)-烷基;
R11非常特别优选代表氢或甲基;
R11最优选代表氢。
本发明的第十二个实施方案包含通式(I)的化合物,其中
X优选选自化学键、CH2、O、S、羰基、NH、CH(C1-C6)-烷基、N(C1-C6)-烷基、OCH2和SCH2,其中上述最后提及的两个基团中的碳原子与芳族部分相连,杂原子O或S与部分氢化的胺部分相连;
X特别优选选自化学键、CH2、O、S、CHCH3、NCH3、OCH2和SCH2,其中上述最后提及的两个基团中的碳原子与芳族部分相连,杂原子O或S与部分氢化的胺部分相连;并且其中
X最优选代表化学键、CH2或O。
在本发明的上下文中,取代基R1a至R11和X的单独优选、更优选和甚至更优选的定义可以根据需要彼此进行组合,其中顺序数n为0、1或2。
这意味着本发明涵盖通式(I)的化合物,其中,例如,取代基R1a具有优选的定义且取代基R1b至R14具有宽泛定义,或取代基R2a具有优选的定义且取代基R3具有特别优选或非常特别优选的定义并且其他取代基有宽泛定义。
上述针对取代基R1a至R11和X给出的定义的这些组合中的三种在下文中详细说明,并且各自作为进一步实施方案公开:
-取代基R1至R11和X的上述各自特别优选的定义的组合(第十三个实施方案),
-取代基R1至R11和X的上述各自非常特别优选的定义的组合(第十四个实施方案),和
-取代基R1至R11和X的上述各自最优选的定义的组合(第十五个实施方案),和
为了清楚起见,在下文明确公开了基于取代基的优选组合的上述进一步的实施方案:
本发明的第十三个实施方案包含通式(I)的化合物,其中
R1a选自氢、(C1-C3)-烷基、(C1-C3)-卤代烷基、(C2-C3)-烯基和(C2-C3)-炔基;
R1b选自氰基;(C1-C4)-烷基;(C1-C4)-卤代烷基;(C1-C3)-烷氧基羰基甲基;(C2-C4)-烯基;(C2-C4)-卤代烯基;(C2-C4)-炔基;(C2-C4)-卤代炔基;苯基,其芳基部分可被卤素和/或甲基取代;CH2-苯基(苄基),其芳基部分可以被卤素和/或甲基取代;和(C3-C6)-环烷基,其环烷基可为未取代的或被甲基和/或卤素单取代或多取代;
其中,如果R1a不代表氢,则R1a通过化学键与R1b相连,使得它们与这两个基团所连接的碳一起形成饱和的3至6元碳环,该碳环为未取代的或被一或多个甲基基团取代,特别优选其中环单元各自由CH2单元形成的未取代的3至6元碳环;
R2a和R2b各自彼此独立地选自氢、(C1-C6)-烷基、(C1-C6)-卤代烷基、(C1-C3)-烷氧基、(C1-C3)-烷氧基-(C1-C3)-烷基和(C3-C6)-环烷基;
R3选自氢、(C1-C4)-烷基羰基、苯基羰基(苯甲酰基)、(C1-C3)-烷基、CH2(C2-C3)-烯基、CH(CH3)(C2-C3)-烯基、CH2(C2-C3)-炔基、CH(CH3)(C2-C3)-炔基、(C1-C3)-烷氧基羰基甲基、CH2-苯基(苄基)、CH2(4-F-苯基)和Si(CH3)3;
R4和R5各自彼此独立地选自氢、羟基、(C1-C6)-烷基、(C1-C6)-烷基苯基和(C1-C6)-烷氧基;
R6和R7彼此独立地选自氢、甲基和苯基;
R8选自氢、卤素、氰基、CO(O)H、(C1-C3)-烷基、(C1-C3)-烷氧基、(C1-C3)-烷氧基羰基和(C6-C8)-芳基;
R9选自氢、氯、氟和(C1-C3)-烷氧基;
R10选自氢、氟、氯、溴、碘、氰基、甲氧基(OCH3)、(C1-C3)-烷基、(C1-C3)-卤代烷基、(C1-C3)-烷氧基、(C2-C4)-烯基、(C2-C4)-炔基、(C1-C3)-烷基-(C2-C4)-炔基、羟基-(C1-C3)-烷基-(C2-C4)-炔基、(C1-C3)-烷氧基-(C2-C4)-炔基和苯基-(C2-C4)-炔基;
R11选自氢和(C1-C4)-烷基;
X代表化学键或O、S、羰基、CH2、NH、CHCH3、NCH3、C(CH3)2、OCH2和SCH2,其中上述最后提及的两个基团中的碳原子与芳族部分相连,杂原子O或S与部分氢化的胺部分相连;
本发明的第十四个实施方案包含通式(I)的化合物,其中
R1a选自氢、CH3、CH2CH3、CF3、C(H)=CH2和C≡CH;
R1b选自氰基、CH3、CH2CH3、CH2CH(CH3)2、CF3、(C1-C2)-烷氧基羰基甲基、C(H)=CH2、C(H)=C(CH3)2、(CH2)2CH=CH2、C≡CH、C≡CCH3、苯基、CH2-苯基(苄基)和环丙基;
其中,如果R1a不代表氢,则R1a通过化学键与R1b相连,使得它们与这两个基团所连接的碳一起形成饱和的3元碳环,该碳环为未取代的或被甲基取代;
R2a和R2b非常特别优选各自彼此独立地选自氢、CH3、CH2CH3、CH(CH3)2、CF3、CF2H、CF2Cl、CH(CH3)F、C(CH3)2F、环丙基和CH2OCH3;
R3选自氢、CH3、CH2CH3、CH2CH=CH2、CH2C(CH3)=CH2、CH2CH=CHCH3、CH2C≡CH、CH2C≡CCH3、CH(CH3)C=CH2、CH(CH3)C≡CH和CH2C(O)OCH3;
R4和R5各自彼此独立地选自氢、(C1-C6)-烷基和(C1-C6)-烷氧基;
R6和R7彼此独立地代表氢或甲基;
R8选自氢、氟、氯、CH3、甲氧基羰基和苯基;
R9选自氢、氟、氯和甲氧基;
R10选自氢、氟、氯、溴、碘、氰基、甲基、C≡CH和C≡CCH3;
R11代表氢或甲基;并且
X代表化学键或O、S、CH2、CHCH3、OCH2、SCH2和NCH3,其中上述最后提及的两个基团中的碳原子与芳族部分相连,杂原子O或S与部分氢化的胺部分相连;
本发明的第十五个实施方案包含通式(I)的化合物,其中
R1a选自氢、CH3、CH2CH3;
R1b选自氰基、CH3、CH2CH3、CF3、C(H)=CH2、C≡CH和C≡CCH3;
其中,如果R1a不代表氢,则R1a通过化学键与R1b相连,使得它们与这两个基团所连接的碳一起形成饱和的3元碳环,该碳为未取代的;
R2a和R2b各自彼此独立地选自氢、CH3、CH(CH3)F和CF2H;
R3选自氢或CH3;
R4和R5各自彼此独立地代表氢或甲基;
R6和R7各自代表氢;
R8代表氢或CH3;
R9代表氢;
R10代表氢或CH3;
R11代表氢;并且
X代表化学键、CH2或O。
在本发明的上下文中,通式(I)的化合物还包括在氮原子上通过a)质子化、b)烷基化或c)氧化而被季铵化的化合物。在这方面,特别提及的是相应的N-氧化物。
式(I)的化合物能形成盐。盐可通过将碱作用于带有酸性氢原子的那些式(I)的化合物而形成。合适的碱为例如有机胺,例如三烷基胺、吗啉、哌啶或吡啶;以及铵、碱金属或碱土金属的氢氧化物、碳酸盐和碳酸氢盐,尤其是氢氧化钠、氢氧化钾、碳酸钠、碳酸钾、碳酸氢钠和碳酸氢钾。这些盐为其中酸性氢被适于农业的阳离子替代的化合物,例如,金属盐,尤其是碱金属盐或碱土金属盐,特别是钠盐和钾盐;或铵盐、有机胺盐或季铵盐,例如具有式[NRR′R″R″′]+(其中R至R″′各自彼此独立地代表有机基团,特别是烷基、芳基、芳烷基或烷基芳基)的阳离子的盐。还合适的有烷基锍盐和烷基氧化锍盐,例如(C1-C4)-三烷基锍盐和(C1-C4)-三烷基氧化锍盐。
式(I)的化合物可通过将合适的无机或有机酸加至碱性基团上而形成盐;所述无机或有机酸为例如无机酸,例如HCl、HBr、H2SO4、H3PO4或HNO3;或有机酸,例如羧酸(例如甲酸、乙酸、丙酸、草酸、乳酸或水杨酸)或磺酸(例如对甲苯磺酸);所述碱性基团为例如氨基、烷基氨基、二烷基氨基、哌啶子基、吗啉代或吡啶并。在这种情况中,这些盐包含作为阴离子的所述酸的共轭碱。
以去质子化形式存在的合适的取代基(例如磺酸或羧酸)可与其本身可被质子化的基团(如氨基)形成内盐。
式(I)的化合物及其盐在下文中也简称为本发明的或根据本发明使用的“化合物(I)”。
在通式(I)和本发明的所有其他式中,碳骨架中的基团烷基、烷氧基、卤代烷基、卤代烷氧基、烷基氨基、烷硫基、卤代烷硫基和相应的不饱和的和/或取代的基团在每种情况下可为直链或支链的。除非另有说明,这些基团优选为低级碳骨架,例如具有1至6个碳原子,特别是1至4个碳原子,或在不饱和基团的情况下具有2至6个碳原子,特别是2至4个碳原子。在单独和复合定义(如烷氧基、卤代烷基等)中的烷基基团为,例如,甲基、乙基、正丙基或异丙基、正丁基、异丁基、叔丁基或2-丁基、戊基、己基(例如正己基、异己基和1,3-二甲基丁基)、庚基(例如正庚基、1-甲基己基和1,4-二甲基戊基);烯基和炔基基团具有对应于烷基的可能的不饱和基团的定义;其中分别存在至少一个双键或三键,优选一个双键或三键。烯基为,例如,乙烯基、烯丙基、1-甲基丙-2-烯-1-基、2-甲基丙-2-烯-1-基、丁-2-烯-1-基、丁-3-烯-1-基、1-甲基丁-3-烯-1-基和1-甲基丁-2-烯-1-基;炔基为,例如,乙炔基、丙炔基、丁-2-炔-1-基、丁-3-炔-1-基和1-甲基丁-3-炔-1-基。
环烷基为,例如,环丙基、环丁基、环戊基、环己基、环庚基和环辛基。该环烷基可以双环或三环形式存在。
如果特别是给出了卤代烷基和卤代烷氧基、卤代烷硫基、卤代烯基、卤代炔基等的卤代烷基基团,则这些具有例如1至6个碳原子或2至6个碳原子、特别是1至4个碳原子或优选2至4个碳原子的基团的低级碳骨架和相应的不饱和的和/或取代基团的碳骨架在每种情况下为直链或支链的。实例为二氟甲基、2,2,2-三氟乙基、三氟烯丙基、1-氯丙-1-炔-3-基。
在这些基团中,亚烷基基团为低级碳骨架(例如具有1至10个碳原子、特别是1至6个碳原子或优选2至4个碳原子的那些)以及相应的不饱和的和/或取代的基团,其碳骨架在每种情况下可为直链或支链的。实例为亚甲基、亚乙基、正亚丙基和异亚丙基以及正亚丁基、仲亚丁基、异亚丁基、叔亚丁基。
在这些基团中,羟基烷基为低级碳骨架(例如具有1至6个碳原子、尤其是1至4个碳原子的那些)以及相应的不饱和的和/或取代的基团,其碳骨架在每种情况下可为直链或支链的。它们的实例为1,2-二羟基乙基和3-羟基丙基。
卤素为氟、氯、溴或碘。卤代烷基、卤代烯基和卤代炔基为被卤素,优选被氟、氯或溴,尤其是被氟和/或氯部分或完全取代的烷基、烯基和炔基,例如单卤代烷基、全卤代烷基、CF3、CF2Cl、CHF2、CH2F、CF3CF2、CH2FCHCl、CCl3、CHCl2、CH2CH2Cl;卤代烷氧基为,例如OCF3、OCHF2、OCH2F、CF3CF2O、OCH2CF3和OCH2CH2Cl;这同样适用于卤代烯基和其他卤素取代的基团。
芳基为单环、双环或多环芳族体系,例如苯基或萘基,优选苯基。
主要由于更高的除草活性、较好的选择性和/或较好的可制备性,特别感兴趣的本发明通式(I)的化合物或其农业化学的盐或或其季N衍生物是其中各个基团具有已指定或下文中指定的优选定义之一的那些,或尤其是其中一个或多个已指定或下文中指定的优选定义组合出现的那些。
上述宽泛或优选的基团定义既适用于通式(I)的最终产品也相应地适用于在每种情况下制备所需的起始材料和中间体。这些基团的定义可根据需要彼此互换,即包括所给的优选范围之间的组合。
如果互变异构体是可能的,则所描述的形式涵盖所有可能的互变异构体结构。如下文所示,例如当R2a和/或R2b=羟基时,同样可涵盖可能的酮互变异构体。
本发明通式(I)的化合物在与氨基嘧啶键合的位点上具有手性碳原子,在下面所示的结构中,用标记(*)表示:
根据Cahn、Ingold和Prelog的规则(CIP规则),该碳原子可具有(R)构型或(S)构型。
本发明涵盖具有(S)和(R)构型的通式(I)的化合物,这意味着本发明涵盖通式(I)的化合物,其中所述碳原子具有
(1)(R)构型;或
(2)(S)构型。
另外,本发明的范围还涵盖
(3)具有(R)构型的通式(I)的化合物(通式(I-(R))的化合物)与具有(S)构型的通式(I)的化合物(通式(I-(S))的化合物)的任意混合物,本发明同样包含具有(R)和(S)构型的通式(I)的化合物的外消旋混合物。
然而,在本发明的上下文中,优选使用选择性为60至100%,优选80至100%,尤其是90至100%,非常特别为95至100%的具有(R)构型的特定通式(I)的化合物,其中存在的特定的(R)化合物在每种情况下具有的对映选择性大于50%ee,优选60至100%ee,尤其是80至100%ee,非常特别为90至100%ee,最优选95至100%ee,基于所述(R)化合物的总含量计。
因此,本发明尤其涉及通式(I*)的化合物,其中在由(*)标记的碳原子上的立体化学构型以60至100%(R)、优选80至100%(R)、特别是90至100%(R)、非常特别95至100%(R)的立体化学纯度存在。
考虑到Cahn、Ingold和Prelog规则,在由(*)标记的碳原子上,其中由于所述的取代基的优先性,还可能存在这样的情况,(S)构型优选存在由(*)标记的碳原子上。例如当基团R4和/或R5对应于C1-C6-烷氧基时,属于这种情况。
因此,在本发明的上下文中,尤其优选这样的通式(I)的化合物,其空间排列对应于具有(R)构型的R4和R5=氢的通式(I)的化合物的空间排列,所述化合物的选择性为60至100%,优选80至100%,尤其是90至100%,非常特别为95至100%;其中存在的各(R)-类似化合物在每种情况下具有大于50%ee、优选60至100%ee、尤其是80至100%ee、非常特别为90至100%ee、最优选95至100%ee的对映选择性,基于所述(R)类似化合物的总含量计。因此,本发明尤其涉及通式(I)的化合物,其中由(*)标记的碳原子上的立体化学构型以60至100%(R或R类似物)、优选80至100%(R或R类似物)、尤其是90至100%(R或R类似物)、非常特别是95至100%(R或R类似物)的立体化学纯度存在。
特别地,本发明通式(I)的化合物可在由(**)和(***)标记的碳原子上具有其他手性中心:
在本发明的上下文中,在由(*)、(**)和(***)标记的碳原子上可具有任何立体化学构型:
另外,根据所选择的各基团,本发明通式(I)的化合物中还可存在其他立体元素(stereoelements)。
例如,如果存在一个或多个烯基,则可出现非对映异构体(Z和E异构体)。
例如,如果存在一个或多个不对称碳原子,则可出现对映异构体和非对映异构体。
相应的立体异构体可由制备过程中所得的混合物通过常规分离法(例如色谱分离法)来获得。同样可使用光学活性起始材料和/或助剂通过立体选择性反应来选择性制备立体异构体。因此,本发明还涉及通式(I)所涵盖的、但未示出其具体立体异构体形式的所有立体异构体及其混合物。
通式(I)的各种取代基的可能的结合应当理解为必须遵守构建化学化合物的一般原则,即式(I)不包括本领域技术人员已知化学上不可能的任何化合物。
通式(I)的化合物的实例在下文中以表格形式示出。
下文表1详细说明了式(I)中以一般术语定义的取代基。在这些表中:
-“StNH”是在碳原子上的立体化学排布,该碳原子上连接有氮原子和氢原子,"StR4R5"和"StR6R7"类似地表示各取代基所连接的碳原子的立体化学排列,
-取代基的键在每种情况下位于左侧,
-如果X有两个键合位点,则左侧键与芳族环相连,右侧键与双环胺的氢化部分相连,
-连字符“-”表示直连键,以及
-如果n=0,则该表在R6和R7的相应位置上不包含条目。
本发明还提供制备相应的通式(I)的化合物和/或其盐和/或其农业上可接受的季铵化氮衍生物的方法,
其中,基团R1a至R11和X和n具有上述含义,
并且根据第一个方法(方法(a)),将通式(II)的化合物
其中R1a、R1b、R2a、R2b和R3具有上述含义,Z1代表可交换基团或离去基团,
与通式(III)的胺或通式(III)的胺的酸加成盐进行反应,
其中基团R4至R11、X和n有上述含义。
可交换基团Z1或离去基团Z1代表氟、氯、溴、碘、(C1-C4)-烷基硫烷基或(C1-C4)-烷基亚磺酰基或(C1-C4)-烷基磺酰基、未取代的苯基-(C1-C4)-烷基磺酰基或被氟、氯、溴或(C1-C4)-烷基或(C1-C4)-烷氧基单取代或多取代的苯基-(C1-C4)-烷基磺酰基,或代表(C1-C4)-烷基苯基磺酰基。
特别优选可交换基团Z1或离去基团Z1为氯、甲基硫烷基、甲基亚磺酰基或甲基磺酰基。
如果必要的话,Z1基团可转化成另一种更好的可交换基团。例如,在两步一锅法的上下文中,(C1-C4)-烷基硫烷基可用氧化剂(例如间氯过氧苯甲酸或)转化成(C1-C4)-烷基亚磺酰基或(C1-C4)-烷基磺酰基或其混合物,然后利用助剂碱(例如三乙胺或碳酸钾)与通式(III)的胺或酸加成盐反应。
反应也可以任选地通过各种助剂(例如通过试剂磷酸钾、碘化亚铜(I)和N,N-二乙基-2-羟基苯甲酰胺)进行催化,或通过特定的过渡金属催化体系以布赫瓦尔德-哈特维希(Buchwald-Hartwig)偶联的方式进行催化。
通式(II)的化合物可以通过已知的方法来制备,例如由相应的5-酮嘧啶开始制备。因此,下文所述的[5-C(=O)-R1b]类型的通式(IIa)的5-酮嘧啶可以例如通过文献中已知的还原方法转化为其中R1a和R3代表氢的式(I)的化合物。优选使用硼氢化钠进行还原。此外,下文所述的[5-C(=O)-R1a]类型的式(IIb)的醛或酮可以例如通过与碳亲核试剂的反应而转化为式(I)的化合物。碳亲核试剂在C-O双键上进行的这种反应,例如羟醛加成(aldoladdition)、格氏反应(Grignard reaction)或者Reformatzky反应都是本领域技术人员由文献所熟知的。
通式(II)的化合物也可以例如通过已知的方法由相应的5-卤代嘧啶,特别优选由相应的5-溴嘧啶或5-碘嘧啶来制备。因此,相应的5-卤代嘧啶可以例如使用式R1aC(O)R1b的酮和有机锂化合物如正丁基锂而转化为其中R3代表氢的通式(II)的化合物。
如果R3代表氢,则该氢原子可以例如通过烷基化或酰基化类型的反应而转化为式(II)的其他分子。
如果R3代表氢,则仅在与通式(III)的胺进行反应后,该氢原子也可以通过烷基化或酰基化类型的反应而转化为式(I)的其他分子。
通式(III)的胺或其酸加成盐是市售可得的,或其合成记载于WO2004/069814 A1。
在另一实施方案中,通式(I)的化合物和/或其农业化学上可接受的盐和/或其农业化学上可接受的季铵化氮衍生物通过第二种方法(b)来制备
其中基团R1a至R11以及X和n有上述含义,
其中首先将通式(IIa)的化合物与
其中R1b、R2a、R2b具有上述含义且Z1代表可交换基团或离去基,与通式(III)的胺或通式(III)的胺的酸加成盐进行反应
其中基团R4至R11、X和n有上述含义,
而得到式(Ia)的2-氨基-5-酮嘧啶衍生物
其中基团R1b至R11以及X和n具有上述含义。
可交换基团Z1或离去基团Z1为氟、氯、溴、碘、(C1-C4)-烷基硫烷基或(C1-C4)-烷基亚磺酰基或(C1-C4)-烷基磺酰基、未取代的或取代的苯基-(C1-C4)-烷基磺酰基或(C1-C4)-烷基苯基磺酰基。
特别优选可交换基团Z1或离去基团Z1为氯、甲基硫烷基、甲基亚磺酰基或甲基磺酰基。
如果必要的话,Z1基团可转化成另一种更好的可交换基团。例如,在两步一锅法的上下文中,(C1-C4)-烷基硫烷基可用氧化剂(例如间氯过氧苯甲酸或)转化成(C1-C4)-烷基亚磺酰基或(C1-C4)-烷基磺酰基或其混合物,然后利用助剂碱(例如三乙胺或碳酸钾)与通式(III)的胺或酸加成盐反应。
反应也可以任选地通过各种助剂(例如通过试剂磷酸钾、碘化亚铜(I)和N,N-二乙基-2-羟基苯甲酰胺)进行催化,或通过特定的过渡金属催化体系以布赫瓦尔德-哈特维希(Buchwald-Hartwig)偶联的方式进行催化。
通式(IIa)的化合物是市售可得的或可以通过已知的方法制备,例如通过文献WO2016/001118 A1中记载的方法制备。
通式(III)的胺或其酸加成盐是市售可得的,或其合成记载于WO2004/069814 A1。
通过这种方法制备的式(Ia)的2-氨基-5-酮嘧啶衍生物然后通过文献已知的还原方法转化为其中R1a和R3代表氢的式(I)的化合物。优选使用硼氢化钠进行还原。
此外,以这种方法制备的式(Ia)的2-氨基-5-酮嘧啶衍生物可以使用[类型为(R1a)-的]碳亲核试剂转化而得到其中R3代表氢的式(I)的化合物。适于引入基团R1a的这类反应,例如羟醛加成、格氏反应(使用R1aMgHal)或者Reformatzky反应都是本领域技术人员由文献所熟知的。
在所得的其中R3代表氢的式(I)的化合物中,氢原子(R3=H)可以例如通过烷基化或酰基化类型的反应而转化为其中R3不代表氢的式(I)的其他分子。
类似b.中所描述的方法,也可以使用通式(IIb)的醛或酮作为原料来制备式(I)的化合物。
在这里,将通式(IIb)的醛或酮
其中R1b、R2a、R2b有上述含义且Z1代表可交换基团或离去基团,与通式(III)的胺或通式(III)的胺的酸加成盐进行反应
其中基团R4至R11、X和n有上述含义,
而得到式(Ib)的2-氨基-5-酮嘧啶衍生物
其中基团R1a至R11以及X和n有上述含义。
可交换基团Z1或离去基团Z1为氟、氯、溴、碘、(C1-C4)-烷基硫烷基或(C1-C4)-烷基亚磺酰基或(C1-C4)-烷基磺酰基、未取代的或取代的苯基-(C1-C4)-烷基磺酰基或(C1-C4)-烷基苯基磺酰基。
特别优选可交换基团Z1或离去基团Z1为氯、甲基硫烷基、甲基亚磺酰基或甲基磺酰基。
如果必要的话,Z1基团可转化成另一种更好的可交换基团。例如,在两步一锅法的上下文中,(C1-C4)-烷基硫烷基可用氧化剂(例如间氯过氧苯甲酸或)转化成(C1-C4)-烷基亚磺酰基或(C1-C4)-烷基磺酰基或其混合物,然后利用助剂碱(例如三乙胺或碳酸钾)与通式(III)的胺或酸加成盐反应。
反应也可以任选地通过各种助剂(例如通过试剂磷酸钾、碘化亚铜(I)和N,N-二乙基-2-羟基苯甲酰胺)进行催化,或通过特定的过渡金属催化体系以布赫瓦尔德-哈特维希(Buchwald-Hartwig)偶联的方式进行催化。
通式(IIb)的化合物是市售可得的或可以通过已知的方法制备,例如通过文献WO2016/001118 A1中记载的方法制备。
以这种方法制备的式(Ib)的2-氨基-5-酮嘧啶衍生物可以使用[类型为(R1b)-的]碳亲核试剂通过文献已知的反应进行转化而得到其中R3代表氢的式(I)的化合物。这类反应,例如羟醛加成、格氏反应(使用R1bMgHal)或者Reformatzky反应都是本领域技术人员由文献所熟知的。
在所得的其中R3代表氢的式(I)的化合物中,氢原子(R3)可以例如通过烷基化或酰基化类型的反应而转化为其中R3不代表氢的式(I)的其他分子。
或者,通式(I)的化合物也可以通过第三种方法(c)来制备,首先以类似于a.中所述的方法,将式(IIc)的化合物
其中R2a和R2b具有上文给出的含义且Z1代表可交换基团或离去基团,
使用式(III)的胺或式(III)的胺的酸加成盐转化为式(Ic)的中间体,
其中基团R2a至R11以及X和n有上述含义。
所得的通式(Ic)的化合物(其中(C1-C6)-烷基特别优选为甲基或乙基)然后可以通过文献中记载的方法(特别优选通过格氏反应)转化为其中R1a和R1b具有相同含义的通式(I)的化合物。因此,变化(c)代表获得式(I)的化合物(其中例如R1a=CH3且R1b=CH3)的另外的选项。
可通过上述反应合成的式(I)的化合物和/或其盐的集合还可以平行的方式制备,在这种情况下,其可以手动、半自动或全自动的方式实现。例如,可自动进行反应、产物和/或中间体的后处理或纯化。总的来说,这应当理解为意指例如D.Tiebes在CombinatorialChemistry–Synthesis,Analysis,Screening(编辑:Günther Jung),Wiley,1999,第1至34页中记载的过程。
对于平行进行的反应和后处理,可使用一系列市售可得的设备,例如购自Radleys,Shirehill,Saffron Walden,Essex,CB11 3AZ,England的反应站,或购自PerkinElmer,Waltham,Massachusetts 02451,USA的MultiPROBE自动化工作站。对于通式(I)的化合物及其盐或在制备过程中出现的中间体的平行纯化,可用的仪器包括色谱仪器,例如购自Teledyne ISCO,Inc.,4700Superior Street,Lincoln,NE 68504,USA的色谱仪器。
所述仪器可形成模块化程序,其中各个工作步骤是自动的,但是在工作步骤之间必须进行手动操作。这可通过使用部分或完全集成的自动化***来避免,其中各自动化模块例如由机器人操控。
单个或多个合成步骤的实施可通过使用聚合物负载的试剂/清除树脂来辅助。专业文献记载了一系列实验方案,例如在ChemFiles,第4卷,第1期,Polymer-SupportedScavengers and Reagents for Solution-Phase Synthesis(Sigma-Aldrich)中。
除了本文中描述的方法之外,通式(I)的化合物及其盐还可全部或部分地通过固相负载的方法制备。为此,将所述合成中或适用于相应过程的合成中的单个中间体或全部中间体结合至合成树脂上。固相负载的合成方法在技术文献,例如Barry A.Bunin在“TheCombinatorial Index”,Academic Press,1998和Combinatorial Chemistry–Synthesis,Analysis,Screening(编辑:Günther Jung),Wiley,1999中进行了详细的描述。使用固相负载的合成方法可实施文献中已知的一系列方案,所述方案也可通过手动或自动化方式进行。
在固相和液相中进行单个或多个合成步骤可通过使用微波技术来辅助。专业的文献,例如Microwaves in Organic and Medicinal Chemistry(编辑:C.O.Kappe和A.Stadler),Wiley,2005中记载了一系列实验方案。
通过本文所述的方法进行的制备,得到物质集合形式的式(I)的化合物及其盐,其称为库(libraries)。本发明还提供了包括至少两种式(I)的化合物及其盐的库。
由于通式(I)的化合物的除草特性,本发明另外还提供了本发明的通式(I)的化合物作为除草剂用于防治有害植物的用途。
在不同的栽培阶段过程中将除草剂用于农业上利用的作物中。因此,一些产品的施用甚至在播种前或播种期间进行。其他产品在作物植物出苗前施用,即在幼苗钻出土壤表面之前施用(苗前除草剂)。最后,如果作物植物已形成子叶或营养叶,则可使用苗后除草剂。
本发明的化合物可在苗前或苗后使用,优选在苗前使用本发明的化合物。
苗前处理包括在播种前对栽培区域的处理(ppi=种植前掺入)和对尚未长出任何生长物的播种栽培区域的处理。
本发明的式(I)化合物及其盐(在下文中还同义并统称为式(I)的化合物)对广谱的经济上重要的单子叶和双子叶有害植物具有优异的除草功效。所述活性化合物还能良好地防治从根茎、根状茎和其他多年生器官发芽的难以防治的多年生杂草。在本文中,该物质是否通过播种前法、苗前法还是苗后法施用并不重要。
可通过本发明通式(I)的化合物防治的一些代表性的单子叶和双子叶杂草植物群的具体实例如下所示,但以下的列举并不限于特定的物种。
对于单子叶杂草物种,例如剪股颖属(Agrostis)、看麦娘属(Alopecurus)、阿披拉草属(Apera)、燕麦属(Avena)、臂形草属(Brachiaria)、雀麦属(Bromus)、龙爪茅属(Dactyloctenium)、马唐属(Digitaria)、稗属(Echinochloa)、荸荠属(Eleocharis)、蟋蟀草属(Eleusine)、羊茅属(Festuca)、飘拂草属(Fimbristylis)、鸭嘴草属(Ischaemum)、黑麦草属(Lolium)、雨久花属(Monochoria)、黍属(Panicum)、雀稗属(Paspalum)、虉草属(Phalaris)、梯牧草属(Phleum)、早熟禾属(Poa)、慈姑属(Sagittaria)、莞草属(Scirpus)、狗尾草属(Setaria)、尖瓣花属(Sphenoclea),主要是一年生的莎草属(Cyperus)物种,对于多年生物种冰草属(Agropyron)、狗牙根属(Cynodon)、白茅属(Imperata)和高粱属(Sorghum)以及多年生的莎草属(Cyperus)物种,均能较好地防治。
在双子叶杂草物种的情况下,作用谱扩展至:例如,一年生的拉拉藤属(Galium)、堇菜属(Viola)、婆婆纳属(Veronica)、野芝麻属(Lamium)、繁缕属(Stellaria)、苋属(Amaranthus)、白芥属(Sinapis)、番薯属(Ipomoea)、母菊属(Matricaria)、苘麻属(Abutilon)和黄花稔属(Sida),以及在多年生杂草情况下的旋花属(Convolvulus)、蓟属(Cirsium)、酸模属(Rumex)和蒿属(Artemisia)。另外,在以下双子叶杂草的情况下,也观察到除草作用:例如豚草属(Ambrosia)、春黄菊属(Anthemis)、飞廉属(Carduus)、矢车菊属(Centaurea)、藜属(Chenopodium)、蓟属(Cirsium)、旋花属(Convolvulus)、曼陀罗属(Datura)、刺酸模属(Emex)、鼬瓣花属(Galeopsis)、牛膝菊属(Galinsoga)、独行菜属(Lepidium)、母草属(Lindernia)、罂粟属(Papaver)、马齿苋属(Portlaca)、蓼属(Polygonum)、毛茛属(Ranunculus)、蔊菜属(Rorippa)、节节菜属(Rotala)、千里光属(Seneceio)、田菁属(Sesbania)、茄属(Solanum)、苦苣菜属(Sonchus)、蒲公英属(Taraxacum)、车轴草属(Trifolium)、荨麻属(Urtica)和苍耳属(Xanthium)。
如果将本发明通式(I)的化合物在萌芽前施用至土壤表面,则可完全防止杂草幼苗的发芽,或杂草生长达到子叶阶期,但随后其生长停止并最终在三到四周后彻底死亡。
如果将通式(I)的活性化合物在出苗后施用至植物的绿色部位,则同样在处理后非常快速地停止生长,且杂草植物停留在所述施用时的生长阶段,或其在一定时间后彻底死亡,从而以该方式能够极早地并以持久的方式消除对作物植物有害的杂草的竞争。
虽然本发明通式(I)的化合物对单子叶和双子叶杂草具有优异的除草活性,但如果存在的话,对经济上重要的作物的作物植物(例如小麦、大麦、黑麦、稻、玉米、糖用甜菜、棉花、油籽油菜和大豆)仅具有可忽略的损害。这是本发明的化合物非常适用于选择性防治农业上有用植物中的不想要的植物生长的原因。
另外,本发明通式(I)的物质对作物植物具有优异的生长调节性能。它们以调控方式干预植物自身的新陈代谢,因此可用于定向影响植物成分并促进收获,例如通过引发脱水和矮化生长。另外,它们还适用于一般性的防治和抑制不想要的营养生长,而在此过程中不杀死植物。抑制营养生长对许多单子叶和双子叶作物具有重要作用,因为这可例如减少或完全防止倒伏。
本发明通式(I)的物质可以与其他活性物质、植物生长调节剂和/或安全剂结合使用。
可以与本发明的化合物以混合制剂或桶混形式结合的活性化合物为,例如,已知的基于抑制以下物质的活性化合物,所述物质是例如乙酰乳酸合成酶、乙酰辅酶A羧化酶、纤维素合成酶、烯醇式丙酮酰莽草酸-3-磷酸合成酶、谷氨酰胺合成酶、对羟基苯基丙酮酸双加氧酶、八氢番茄红素去饱和酶、光***I、光***II或原卟啉原氧化酶,例如记载于WeedResearch 26(1986)441-445页或"The Pesticide Manual",第16版,The British CropProtection Council and the Royal Soc.of Chemistry,2006和其中引用的文献中。可以与本发明的化合物结合的已知的除草剂或植物生长调节剂是例如以下的活性化合物,其中所述化合物以国际标准化组织(ISO)规定的通用名表示,或以化学名称、或其编号表示。即使没有明确提及,它们总是涵盖其所有应用形式,例如酸、盐、酯以及所有异构体形式例如立体异构体和光学异构体。
这些除草剂的混合配对体的实例为:
乙草胺(acetochlor)、三氟羧草醚(acifluorfen)、三氟羧草醚(acifluorfen-sodium)、苯草醚(aclonifen)、甲草胺(alachlor)、草毒死(allidochlor)、禾草灭(alloxydim)、枯杀达(alloxydim-sodium)、莠灭净(ametryn)、氨唑草酮(amicarbazone)、先甲草胺(amidochlor)、酰嘧磺隆(amidosulfuron)、环丙嘧啶酸(aminocyclopyrachlor)、环丙嘧啶酸钾盐(aminocyclopyrachlor-potassium)、环丙嘧啶酸甲酯(aminocyclopyrachlor-methyl)、氯氨吡啶酸(aminopyralid)、杀草强(amitrole)、氨基磺酸铵(ammonium sulfamate)、莎稗磷(anilofos)、磺草灵(asulam)、莠去津(atrazine)、唑啶草酮(azafenidin),四唑嘧磺隆(azimsulfuron)、氟丁酰草胺(beflubutamid),草除灵(benazolin)、草除灵(benazolin-ethyl)、乙丁氟灵(benfluralin)、呋草黄(benfuresate)、苄嘧磺隆(bensulfuron,bensulfuron-methyl)、地散磷(bensulide)、灭草松(bentazone)、双环磺草酮(benzobicyclon)、吡草酮(benzofenap)、bicyclopyron、甲羧除草醚(bifenox)、双丙氨膦(bilanafos)、双丙氨膦钠盐(bilanafos-sodium)、双草醚(bispyribac)、双草醚(bispyribac-sodium)、除草定(bromacil)、溴丁酰草胺(bromobutide)、溴酚肟(bromofenoxim)、溴苯腈(bromoxynil)、丁酯溴苯草腈(bromoxynil-butyrate)、溴苯腈钾(bromoxynil-potassium)、溴苯腈庚酸酯(bromoxynil-heptanoate)和溴苯腈辛酸酯(bromoxynil-octanoate)、羟草酮(busoxinone)、丁草胺(butachlor)、氟丙嘧草酯(butafenacil)、抑草磷(butamifos)、丁烯草胺(butenachlor)、仲丁灵(butralin)、丁氧环酮(butroxydim)、丁草敌(butylate)、唑草胺(cafenstrole)、双酰草胺(carbetamide)、唑酮草酯(carfentrazone)、唑酮草酯(carfentrazone-ethyl)、草灭畏(chloramben)、氯溴隆(chlorbromuron)、伐草克(chlorfenac)、双氯酚酸钠(chlorfenac-sodium)、燕麦酯(chlorfenprop)、氯甲丹(chlorflurenol)、氯甲丹(chlorflurecol-methyl)、氯草敏(chloridazon)、氯嘧磺隆(chlorimuron)、氯嘧磺隆(chlorimuron-ethyl)、4-氯邻苯二甲酸(chlorophthalim)、绿麦隆(chlortoluron)、敌草索(chlorthal-dimethyl)、氯磺隆(chlorsulfuron)、3-[5-氯-4-(三氟甲基)吡啶-2-基]-4-羟基-1-甲基咪唑烷-2-酮、吲哚酮草酯(cinidon、cinidon-ethyl)、环庚草醚(cinmethylin)、醚磺隆(cinosulfuron)、氯酰草膦(clacyfos)、烯草酮(clethodim)、炔草酸(clodinafop)、炔草酯(clodinafop-propargyl)、异噁草松(clomazone)、氯甲酰草胺(clomeprop)、二氯吡啶酸(clopyralid)、氯酯磺草胺(cloransulam)、氯酯磺草胺(cloransulam-methyl)、苄草隆(cumyluron)、氨基氰(cyanamide)、氰草津(cyanazine)、环草敌(cycloate)、cyclopyranil、cyclopyrimorate、环丙嘧磺隆(cyclosulfamuron)、噻草酮(cycloxydim)、氰氟草酯(cyhalofop)、氰氟草酯(cyhalofop-butyl)、环丙津(cyprazine)、2,4-D、2,4-D-丁氧基乙酯(2,4-D-butotyl)、2,4-D-丁酯(2,4-D-butyl)、2,4-D-二甲基铵盐(2,4-D-dimethylammonium)、2,4-D-二乙醇胺(2,4-D-diolamine)、2,4-D-ethyl(2,4-D-乙酯)、2,4-D-2-乙基己酯(2,4-D-2-ethylhexyl)、2,4-D-异丁酯(2,4-D-isobutyl)、2,4-D-异辛酯(2,4-D-isooctyl)、2,4-D-异丙基铵盐(2,4-D-isopropylammonium)、2,4-D-钾盐(2,4-D-potassium)、2,4-D-三异丙醇铵盐(2,4-D-triisopropanolammonium)和2,4-D-三乙醇胺(2,4-D-trolamine)、2,4-DB、2,4-DB-丁酯(2,4-DB-butyl)、2,4-DB-dimethylammonium(2,4-DB-二甲基铵盐)、2,4-DB-异辛酯(2,4-DB-isooctyl)、2,4-DB-钾盐(2,4-DB-potassium)和2,4-DB-钠盐(2,4-DB-sodium)、杀草隆(daimuron(dymron))、茅草枯(dalapon)、棉隆(dazomet)、正癸醇(n-decanol)、甜菜安(desmedipham)、detosyl-pyrazolate(DTP)、麦草畏(dicamba)、敌草腈(dichlobenil)、2-(2,4-二氯苄基)-4,4-二甲基-1,2-噁唑烷-3-酮、2-(2,5-二氯苄基)-4,4-二甲基-1,2-噁唑烷-3-酮、2,4-滴丙酸(dichlorprop)、2,4-滴丙酸(dichlorprop-P)、二氯苯氧基丙酸(diclofop)、禾草灵(diclofop-methyl)、禾草灵(diclofop-P-methyl)、双氯磺草胺(diclosulam)、野燕枯(difenzoquat)、吡氟酰草胺(diflufenican)、二氟吡隆(diflufenzopyr)、氟吡草腙(diflufenzopyr-sodium)、噁唑隆(dimefuron)、哌草丹(dimepiperate)、二甲草胺(dimethachlor)、异戊乙净(dimethametryn)、二甲吩草胺(dimethenamid)、甲酚噻草胺-P(dimethenamid-P)、dimetrasulfuron、氨氟灵(dinitramine)、特乐酚(dinoterb)、双苯酰草胺(diphenamid)、敌草快(diquat)、敌草快(diquat dibromide)、氟硫草定(dithiopyr)、敌草隆(diuron)、二硝酚(DNOC)、茵多酸(endothal)、扑草灭(EPTC)、戊草丹(esprocarb)、乙丁烯氟灵(ethalfluralin)、胺苯磺隆(ethamesulfuron)、胺苯磺隆(ethametsulfuron-methyl)、乙嗪草酮(ethiozin)、乙氧呋草黄(ethofumesate)、氟乳醚(ethoxyfen)、氯氟草醚乙酯(ethoxyfen-ethyl)、乙氧嘧磺隆(ethoxysulfuron)、乙氧苯草胺(etobenzanid)、F-9600、F-5231,即N-[2-氯-4-氟-5-[4-(3-氟丙基)-4,5-二氢-5-氧代-1H-四唑-1-基]苯基]乙磺酰胺、F-7967,即3-[7-氯-5-氟-2-(三氟甲基)-1H-苯并咪唑-4-基]-1-甲基-6-(三氟甲基)嘧啶-2,4(1H,3H)-二酮、噁唑禾草灵(fenoxaprop)、噁唑禾草灵(fenoxaprop-P)、噁唑禾草灵(fenoxaprop-ethyl)、精噁唑禾草灵(fenoxaprop-P-ethyl)、fenoxasulfone、fenquinotrione、四唑酰草胺(fentrazamide)、麦草氟(flamprop)、麦草氟异丙酯(fiamprop-M-isopropyl)、麦草氟甲酯(flamprop-M-methyl)、啶嘧磺隆(flazasulfuron)、双氟磺草胺(florasulam)、氯氟吡啶酯(florpyrauxifen、florpyrauxifen-benzyl)、吡氟禾草灵(fluazifop)、精吡氟禾草灵(fluazifop-P)、吡氟禾草灵丁酯(fluazifop-butyl)、精吡氟禾草灵丁酯(fluazifop-P-butyl)、氟唑磺隆(flucarbazone)、氟酮磺隆(flucarbazone-sodium)、氟吡磺隆(flucetosulfuron)、氯乙氟灵(fluchloralin)、氟噻草胺(flufenacet)、氟哒嗪草酯(flufenpyr)、氟哒嗪草酯(flufenpyr-ethyl)、唑嘧磺草胺(flumetsulam)、氟烯草酸(flumiclorac)、氟烯草酸(flumiclorac-pentyl)、丙炔氟草胺(flumioxazin)、氟草隆(fluometuron)、抑草丁(flurenol)、芴醇丁酯(flurenol-butyl)、抑草丁二甲基铵盐(flurenol-dimethylammonium)和芴醇甲酯(flurenol-methyl)、乙羧氟草醚(fluoroglycofen)、乙羧氟草醚(fluoroglycofen-ethyl)、四氟丙酸(flupropanate)、氟啶磺隆(flupyrsulfuron)、氟啶嘧磺隆(flupyrsulfuron-methyl-sodium))、氟啶草酮(fluridone)、氟咯草酮(flurochloridone)、氟草烟(fluroxypyr)、甲基庚酯(fluroxypyr-meptyl)、呋草酮(flurtamone)、嗪草酸(fluthiacet)、氟噻乙草酯(fluthiacet-methyl)、氟磺胺草醚(fomesafen)、氟磺胺草醚钠(fomesafen-sodium)、甲酰氨磺隆(foramsulfuron)、杀木膦(fosamine)、草铵膦(glufosinate)、草铵磷(glufosinate-ammonium)、glufosinate-P-sodium、精草铵磷(glufosinate-P-ammonium)、glufosinate-P-sodium、草甘膦(glyphosate)、草甘膦铵盐(glyphosate-ammonium)、草甘膦异丙基铵盐(glyphosate-isopropylammonium)、草甘膦二铵盐(glyphosate-diammonium)、草甘膦二甲基铵盐(glyphosate-dimethylammonium)、草甘膦钾盐(glyphosate-potassium)、草甘膦钠盐(glyphosate-sodium)和草甘膦三甲基硫盐(glyphosate-trimesium)、H-9201,即O-(2,4-二甲基-6-硝基苯基)O-乙基异丙基硫代磷酰胺酯、氟氯吡啶酸(halauxifen)、氟氯吡啶酯(halauxifen-methyl)、氟硝磺酰胺(halosafen)、氯吡嘧磺隆(halosulfuron)、氯吡嘧磺隆(halosulfuron-methyl)、氟吡禾灵(haloxyfop)、精氟吡禾灵(haloxyfop-P)、氯氟乙禾灵(haloxyfop-ethoxyethyl)、氯氟乙禾灵(haloxyfop-P-ethoxyethyl)、氟吡甲禾灵(haloxyfop-methyl)、氟吡甲禾灵(haloxyfop-P-methyl)、环嗪酮(hexazinone)、HW-02,即(2,4-二氯苯氧基)乙酸1-(二甲氧基磷酰基)乙酯、4-羟基-1-甲氧基-5-甲基-3-[4-(三氟甲基)吡啶-2-基]咪唑烷-2-酮、4-羟基-1-甲基-3-[4-(三氟甲基)吡啶-2-基]咪唑烷-2-酮、咪草酸(imazamethabenz)、咪草酸(imazamethabenz-methyl)、甲氧咪草烟(imazamox)、铵基咪草啶酸(imazamox-ammonium)、甲咪唑烟酸(imazapic)、咪唑烟酸异丙基胺盐(imazapyr-isopropylammonium)、咪唑烟酸(imazapyr)、咪唑烟酸异丙基铵盐(imazapyr-isopropylammonium)、咪唑喹啉酸(imazaquin)、咪唑喹啉酸铵(imazaquin-ammonium)、咪唑乙烟酸(imazethapyr)、咪唑乙烟酸铵(imazethapyr-immonium)、唑吡嘧磺隆(imazosulfuron)、茚草酮(indanofan)、碘甲磺隆(indaziflam)、碘甲磺隆钠盐(iodosulfuron)、碘甲磺隆钠盐(iodosulfuron-methyl-sodium)、碘苯腈(ioxynil)、碘苯腈辛酸酯(ioxynil-octanoate)、碘苯腈钾盐(ioxynil-potassium)、碘苯腈钠盐(ioxynil-sodium)、三哇苯胺除草剂(ipfencarbazone)、异丙隆(isoproturon)、异噁隆(isouron)、异噁酰草胺(isoxaben)、异噁氯草酮(isoxachlortole)、特胺灵(karbutilate)、KUH-043,即3-({[5-(二氟甲基)-1-甲基-3-(三氟甲基)-1H-吡唑-4-基]甲基}磺酰基)-5,5-二甲基-4,5-二氢-1,2-噁唑、ketospiradox、乳氟禾草灵(lactofen)、环草定(lenacil)、利谷隆(linuron)、MCPA、MCPA-丁氧基乙酯(MCPA-butotyl)、MCPA-二甲基铵盐(MCPA-dimethylammonium)、MCPA-2-乙基己酯(MCPA-2-ethylhexyl)、MCPA-异丙基铵盐(MCPA-isopropylammonium)、MCPA-钾盐(MCPA-potassium)和MCPA-钠盐(MCPA-sodium)、MCPB、MCPB-甲酯(MCPB-methyl)、MCPB-乙酯(MCPB-ethyl)和MCPB-钠盐(MCPB-sodium)、2-甲-4-氯丙酸(mecoprop)、2-甲-4-氯丙酸钠(mecoprop-sodium)、2-甲-4-氯丙酸丁氧基乙酯(mecoprop-butotyl)、高2-甲-4-氯丙酸(mecoprop-P)、高2-甲-4-氯丙酸丁氧基乙酯(mecoprop-P-butotyl)、高2-甲-4-氯丙酸二甲基铵(mecoprop-P-dimethylammonium)、高2-甲-4-氯丙酸2-乙基己酯(mecoprop-P-2-ethylhexyl)和高2-甲-4-氯丙酸钾(mecoprop-P-potassium)、苯噻酰草胺(mefenacet)、氯磺酰草胺(mefluidide)、甲磺胺磺隆(mesosulfuron)、甲磺胺磺隆(mesosulfuron-methyl)、甲基磺草酮(mesotrione)、甲基苯噻隆(methabenzthiazuron)、威百亩(metam)、噁唑酰草胺(metamifop)、苯嗪草酮(metamitron)、吡唑草胺(metazachlor)、双醚氯吡嘧磺隆(metazosulfuron)、噻唑隆(methabenzthiazuron)、甲硫嘧磺隆(methiopyrsulfuron)、methiozolin、异硫氰酸甲酯(methyl isothiocyanate)、溴谷隆(metobromuron)、异丙甲草胺(metolachlor)、S-异丙甲草胺(S-metolachlor)、磺草唑胺(metosulam)、甲氧隆(metoxuron)、嗪草酮(metribuzin)、甲磺隆(metsulfuron)、甲磺隆(metsulfuron-methyl)、禾草敌(molinate)、绿谷隆(monolinuron)、单嘧磺隆(monosulfuron)、单嘧磺酯(monosulfuron ester)、MT-5950,即N-[3-氯-4-(1-甲基乙基)苯基]-2-甲基戊酰胺、NGGC-011、敌草胺(napropamide)、NC310,即4-(2,4-二氯苯甲酰基)-1-甲基-5-苄氧基吡唑、草不隆(neburon)、烟嘧磺隆(nicosulfuron)、正壬酸(nonanoic acid(pelargonic acid))、氟草敏(norflurazon)、油酸(oleic acid(脂肪酸))、坪草丹(orbencarb)、嘧苯胺磺隆(orthosulfamuron)、氨磺乐灵(oryzalin)、丙炔噁草酮(oxadiargyl)、噁草酮(oxadiazon)、环氧嘧磺隆(oxasulfuron)、噁嗪草酮(oxaziclomefon)、oxotrione(lancotrione)、乙氧氟草醚(oxyfluorfen)、百草枯(paraquat)、百草枯(paraquat dichloride)、克草猛(pebulate)、二甲戊灵(pendimethalin)、五氟磺草胺(penoxsulam)、五氯苯酚(pentachlorohenol)、环戊噁草酮(pentoxazone)、烯草胺(pethoxamid)、矿物油(petroleum oils)、甜菜宁(phenmedipham)、氨氯吡啶酸(picloram)、氟吡酰草胺(picolinafen)、唑啉草酯(pinoxaden)、哌草磷(piperophos)、丙草胺(pretilachlor)、氟嘧磺隆(primisulfuron)、氟嘧磺隆(primisulfuron-methyl)、氨氟乐灵(prodiamine)、环苯草酮(profoxydim)、扑灭通(prometon)、扑草净(prometryn)、毒草胺(propachlor)、敌稗(propanil)、噁草酸(propaquizafop)、扑灭津(propazine)、苯胺灵(propham)、异丙草胺(propisochlor)、丙苯磺隆(propoxycarbazone)、丙苯磺隆(propoxycarbazone-sodium)、嗪咪唑嘧磺隆(propyrisulfuron)、炔苯酰草胺(propyzamide)、苄草丹(prosulfocarb)、氟磺隆(prosulfuron)、双唑草腈(pyraclonil)、吡草醚(pyraflufen)、吡草醚(pyraflufen-ethyl)、pyrasulfotole、吡唑特(pyrazolynate(pyrazolate))、吡嘧磺隆(pyrazosulfuron,pyrazosulfuron-ethyl)、苄草唑(pyrazoxyfen)、异丙酯草醚(pyribambenz)、异丙酯草醚(pyribambenz-isopropyl)、丙酯草醚(pyribambenz-propyl)、嘧啶肟草醚(pyribenzoxim)、稗草丹(pyributicarb)、达草止(pyridafol)、哒草特(pyridate)、环酯草醚(pyriftalid)、嘧草醚(pyriminobac)、嘧草醚(pyriminobac-methyl)、pyrimisulfan、嘧草硫醚(pyrithiobac)、嘧草硫醚(pyrithiobac-sodium)、异噁草酮(pyroxasulfone)、甲氧磺草胺(pyroxsulam)、二氯喹啉酸(quinchlorac)、氯甲喹啉酸(quinmerac)、灭藻醌(quinoclamine)、喹禾灵(quizalofop)、喹禾灵乙酯(quizalofop-ethyl)、精喹禾灵(quizalofop-P)、精喹禾灵乙酯(quizalofop-P-ethyl)、喹禾糠酯(quizalofop-P-tefuryl)、砜嘧磺隆(rimsulfuron)、苯嘧磺草胺(saflufenacil)、烯禾啶(sethoxydim)、环草隆(siduron)、西玛津(simazine)、西草净(simetryn)、磺草酮(sulcotrione)、甲磺草胺(sulfentrazone)、甲嘧磺隆(sulfometuron)、甲嘧磺隆(sulfometuron-methyl)、磺酰磺隆(sulfosulfuron)、SYN-523、SYP-249,即5-[2-氯-4-(三氟甲基)苯氧基]-2-硝基苯甲酸1-乙氧基-3-甲基-1-氧代丁-3-烯-2-基酯、SYP-300,即1-[7-氟-3-氧代-4-(丙-2-炔-1-基)-3,4-二氢-2H-1,4-苯并噁嗪-6-基]-3-丙基-2-硫代咪唑烷-4,5-二酮、2,3,6-TBA、TCA(三氟乙酸)、三氯乙酸钠(TCA-sodium)、丁噻隆(tebuthiuron)、特呋三酮(tefuryltrione)、环磺酮(tembotrione)、吡喃草酮(tepraloxydim)、特草定(terbacil)、特草灵(terbucarb)、特丁通(terbumeton)、特丁津(terbuthylazine)、去草净(terbutryn)、噻吩草胺(thenylchlor)、噻唑烟酸(thiazopyr)、异草唑酮(thiencarbazone)、噻酮磺隆(thiencarbazone-methyl)、噻吩磺隆(thifensulfuron)、噻吩磺隆(thifensulfuron-methyl)、禾草丹(thiobencarb)、tiafenacil、tolpyralate、苯吡唑草酮(topramezone)、苯草酮(tralkoxydim)、氟酮磺草胺(triafamone)、野麦畏(tri-allate)、醚苯磺隆(triasulfuron)、三嗪氟草胺(triaziflam)、苯磺隆(tribenuron)、苯磺隆(tribenuron-methyl)、三氯吡氧乙酸(triclopyr)、草达津(trietazine)、氟胺磺隆(triflusulfuron)、三氟啶磺隆(trifioxysulfuron-sodium)、trifludimoxazin、氟乐灵(trifluralin)、氟胺磺隆(triflusulfuron、triflusulfuron-methyl)、三氟甲磺隆(tritosulfuron)、硫酸脲、灭草敌(vernolate)、ZJ-0862,即3,4-二氯-N-{2-[(4,6-二甲氧基嘧啶-2-基)氧基]苄基}苯胺和以下化合物:
可作为混合配对体的植物生长调节剂的实例为:
苯并噻二唑(acibenzolar)、苯并噻二唑(acibenzolar-S-methyl)、氨基酮戊酸(5-aminolevulinic acid)、环丙嘧啶醇(ancymidol)、6-苄基氨基嘌呤(6-benzylaminopurine)、芸苔素内酯(brassinolide)、邻苯二酚、矮壮素(chlormequatchloride)、调果酸(cloprop)、环丙酰胺酸(cyclanilide)、3-(环丙-1-烯基)丙酸、丁酰肼、棉隆(dazomet)、正癸醇(n-decanol)、调呋酸(dikegulac)、敌草克(dikegulac-sodium)、茵多酸(endothal)、茵多酸-二钾(endothal-dipotassium)、茵多酸-二钠(endothal-disodium)和单(N,N-二甲基烷基铵)、乙烯利(ethephon)、氟节胺(flumetralin)、抑草丁(flurenol)、芴丁酯(flurenol-butyl)、调嘧醇(flurprimidol)、氯吡脲(forchlorfenuron)、赤霉酸(gibberellic acid)、抗倒胺(inabenfide)、吲哚-3-醋酸(IAA)、4-吲哚-3-基丁酸、稻瘟灵(isoprothiolane)、烯丙苯噻唑(probenazole)、茉莉酸(jasmonic acid)、茉莉酸甲酯(jasmonic acid methyl ester)、马来酰肼、甲哌(mepiquatchloride)、1-甲基环丙烯、2-(1-萘基)乙酰胺、1-萘基乙酸、2-萘基氧基乙酸、硝基苯酚混合物、4-氧代-4[(2-苯基乙基)氨基]丁酸、多效唑(paclobutrazole)、N-苯基邻氨甲酰苯甲酸、调环酸(prohexadione)、调环酸钙(prohexadione-calcium)、茉莉酮(prohydrojasmone)、水杨酸、独角金内酯(strigolactone)、四氯硝基苯(tecnazene)、噻苯隆(thidiazuron)、三十烷醇(triacontanol)、抗倒酯(trinexapac)、抗倒酯(trinexapac-ethyl)、tsitodef、烯效唑(uniconazole)、精烯效唑(uniconazole-P)。
安全剂优选选自:
S1)式(S1)的化合物
其中符号和下标定义如下:
nA为0至5,优选0至3的自然数;
RA 1为卤素、(C1-C4)-烷基、(C1-C4)-烷氧基、硝基或(C1-C4)-卤代烷基;
WA为未取代或取代的二价杂环基团,其选自具有1至3个选自N和O的环杂原子的部分不饱和的或芳族的五元杂环,其中环中存在至少一个氮原子和至多一个氧原子,优选选自(WA 1)至(WA 4)的基团,
mA为0或1;
RA 2为ORA 3、SRA 3或NRA 3RA 4或具有至少一个氮原子和最高达3个杂原子(优选选自O和S)的饱和的或不饱和的3至7元杂环,所述杂环通过氮原子与(S1)中的羰基连接,并且为未取代的或被以下基团取代:(C1-C4)-烷基、(C1-C4)-烷氧基或任选取代的苯基,优选式ORA 3、NHRA 4或N(CH3)2的基团,尤其是式ORA 3的基团;
RA 3为氢或优选具有总共1至18个碳原子的未取代的或取代的脂族烃基团;
RA 4为氢、(C1-C6)-烷基、(C1-C6)-烷氧基或取代的或未取代的苯基;
RA 5为H、(C1-C8)-烷基、(C1-C8)-卤代烷基、(C1-C4)-烷氧基-(C1-C8)-烷基、氰基或COORA 9,其中RA 9为氢、(C1-C8)-烷基、(C1-C8)-卤代烷基、(C1-C4)-烷氧基-(C1-C4)-烷基、(C1-C6)-羟基烷基、(C3-C12)-环烷基或三-(C1-C4)-烷基甲硅烷基;
RA 6、RA 7、RA 8为相同或不同的,并且各自为氢、(C1-C8)-烷基、(C1-C8)-卤代烷基、(C3-C12)-环烷基或取代或未取代的苯基;
优选:
a)二氯苯基吡唑啉-3-羧酸类的化合物(S1a),优选以下化合物:例如,1-(2,4-二氯苯基)-5-(乙氧基羰基)-5-甲基-2-吡唑啉-3-甲酸、1-(2,4-二氯苯基)-5-(乙氧基羰基)-5-甲基-2-吡唑啉-3-甲酸乙酯(S1-1)(“吡唑解草酯”),以及记载于WO-A-91/07874中的相关化合物;
b)二氯苯基吡唑羧酸的衍生物(S1b),优选以下化合物:例如,1-(2,4-二氯苯基)-5-甲基吡唑-3-甲酸乙酯(S1-2)、1-(2,4-二氯苯基)-5-异丙基吡唑-3-甲酸乙酯(S1-3)、1-(2,4-二氯苯基)-5-(1,1-二甲基乙基)吡唑-3-甲酸乙酯(S1-4),以及记载于EP-A-333 131和EP-A-269 806中的相关化合物;
c)1,5-二苯基吡唑-3-羧酸的衍生物(S1c),优选以下化合物:例如,1-(2,4-二氯苯基)-5-苯基吡唑-3-甲酸乙酯(S1-5)、1-(2-氯苯基)-5-苯基吡唑-3-甲酸甲酯(S1-6),以及记载于例如EP-A-268554的相关化合物;
d)***羧酸类的化合物(S1d),优选以下化合物:例如,解草唑(-乙酯),即1-(2,4-二氯苯基)-5-三氯甲基-(1H)-1,2,4-***-3-甲酸乙酯(S1-7),以及记载于EP-A-174562和EP-A-346620中的相关化合物;
e)5-苄基-2-异噁唑啉-3-羧酸或5-苯基-2-异噁唑啉-3-羧酸或5,5-二苯基-2-异噁唑啉-3-羧酸类的化合物(S1e),优选以下化合物:例如,5-(2,4-二氯苄基)-2-异噁唑啉-3-甲酸乙酯(S1-8)或5-苯基-2-异噁唑啉-3-甲酸乙酯(S1-9),以及记载于WO-A-91/08202中的相关化合物,或5,5-二苯基-2-异噁唑啉-3-甲酸(S1-10)或5,5-二苯基-2-异噁唑啉-3-甲酸乙酯(S1-11)(“双苯噁唑酸”)或5,5-二苯基-2-异噁唑啉-3-甲酸正丙酯(S1-12)或5-(4-氟苯基)-5-苯基-2-异噁唑啉-3-甲酸乙酯(S1-13),如记载于专利申请WO-A-95/07897中。
S2)式(S2)的喹啉衍生物
其中符号和下标具有以下含义:
RB 1为卤素、(C1-C4)-烷基、(C1-C4)-烷氧基、硝基或(C1-C4)-卤代烷基;
nB为0至5,优选0至3的自然数;
RB 2为ORB 3、SRB 3或NRB 3RB 4或具有至少一个氮原子和最高达3个杂原子(优选选自O和S)的饱和或不饱和的3至7元杂环,所述杂环通过氮原子与(S2)中的羰基连接,并且为未取代的或被以下基团取代:(C1-C4)-烷基、(C1-C4)-烷氧基或任选取代的苯基,优选式ORB 3、NHRB 4或N(CH3)2,尤其是式ORB 3的基团;
RB 3为氢或优选具有总共1至18个碳原子的未取代的或取代的脂族烃基团;
RB 4为氢、(C1-C6)-烷基、(C1-C6)-烷氧基或取代或未取代的苯基;
TB为(C1或C2)-烷烃二基链,其为未取代的或被一个或两个(C1-C4)-烷基取代或被[(C1-C3)-烷氧基]羰基取代;
优选:
a)8-喹啉氧基乙酸类的化合物(S2a),优选
(5-氯-8-喹啉氧基)乙酸1-甲基己酯(“解草酯”)(S2-1),
(5-氯-8-喹啉氧基)乙酸1,3-二甲基丁-1-基酯(S2-2),
(5-氯-8-喹啉氧基)乙酸4-烯丙基氧基丁酯(S2-3),
(5-氯-8-喹啉氧基)乙酸1-烯丙基氧基丙-2-基酯(S2-4),
(5-氯-8-喹啉氧基)乙酸乙酯(S2-5),
(5-氯-8-喹啉氧基)乙酸甲酯(S2-6),
(5-氯-8-喹啉氧基)乙酸烯丙酯(S2-7),
(5-氯-8-喹啉氧基)乙酸2-(2-亚丙基亚氨基氧基)-1-乙酯(S2-8),(5-氯-8-喹啉氧基)乙酸2-氧代丙-1-基酯(S2-9)以及相关的化合物,如记载于EP-A-86750、EP-A-94349和EP-A-191736或EP-A-0 492 366中,以及(5-氯-8-喹啉氧基)乙酸(S2-10)、其水合物及其盐,例如其锂盐、钠盐、钾盐、钙盐、镁盐、铝盐、铁盐、铵盐、季铵盐、锍盐或鏻盐,如记载于WO-A-2002/34048中;
b)(5-氯-8-喹啉氧基)丙二酸类的化合物(S2b),优选以下化合物:例如,(5-氯-8-喹啉氧基)丙二酸二乙酯、(5-氯-8-喹啉氧基)丙二酸二烯丙酯、(5-氯-8-喹啉氧基)丙二酸甲基乙酯以及相关的化合物,如记载于EP-A-0 582 198中。
S3)式(S3)的化合物
其中符号和下标定义如下:
RC 1为(C1-C4)-烷基、(C1-C4)-卤代烷基、(C2-C4)-烯基、(C2-C4)-卤代烯基、(C3-C7)-环烷基,优选二氯甲基;
RC 2、RC 3为相同或不同的且为氢、(C1-C4)-烷基、(C2-C4)-烯基、(C2-C4)-炔基、(C1-C4)-卤代烷基、(C2-C4)-卤代烯基、(C1-C4)-烷基氨基甲酰基-(C1-C4)-烷基、(C2-C4)-烯基氨基甲酰基-(C1-C4)-烷基、(C1-C4)-烷氧基-(C1-C4)-烷基、二氧戊环基-(C1-C4)-烷基、噻唑基、呋喃基、呋喃基烷基、噻吩基、哌啶基、取代或未取代的苯基,或RC 2和RC 3一起形成取代或未取代的杂环,优选噁唑烷、噻唑烷、哌啶、吗啉、六氢嘧啶或苯并噁嗪环;
优选:
二氯乙酰胺类的活性化合物,其通常用作苗前安全剂(作用于土壤的安全剂),例如
“二氯丙烯胺”(N,N-二烯丙基-2,2-二氯乙酰胺)(S3-1),
购自Stauffer的“R-29148”(3-二氯乙酰基-2,2,5-三甲基-1,3-噁唑烷)(S3-2),
购自Stauffer的“R-28725”(3-二氯乙酰基-2,2-二甲基-1,3-噁唑烷)(S3-3),
“benoxacor(解草酮)”(4-二氯乙酰基-3,4-二氢-3-甲基-2H-1,4-苯并噁嗪)(S3-4),
购自PPG Industries的“PPG-1292”(N-烯丙基-N-[(1,3-二氧戊环-2-基)甲基]二氯乙酰胺)(S3-5),
购自Sagro-Chem的“DKA-24”(N-烯丙基-N-[(烯丙基氨基羰基)甲基]二氯乙酰胺)(S3-6),
购自Nitrokemia或Monsanto的“AD-67”或”MON 4660”(3-二氯乙酰基-1-氧杂-3-氮杂螺[4.5]癸烷)(S3-7),
购自TRI-Chemical RT的“TI-35”(1-二氯乙酰基氮杂环庚烷)(S3-8),
“diclonon”(dicyclonon)或“BAS145138”或“LAB145138”(S3-9),
购自BASF的((RS)-1-二氯乙酰基-3,3,8a-三甲基全氢吡咯并[1,2-a]嘧啶-6-酮),
“呋喃解草唑(furilazole)”或“MON 13900”((RS)-3-二氯乙酰基-5-(2-呋喃基)-2,2-二甲基噁唑烷)(S3-10);以及其(R)异构体(S3-11)。
S4)式(S4)的N-酰基磺酰胺及其盐,
其中符号和下标定义如下:
AD为SO2-NRD 3-CO或CO-NRD 3-SO2,
XD为CH或N;
RD 1为CO-NRD 5RD 6或NHCO-RD 7;
RD 2为卤素、(C1-C4)-卤代烷基、(C1-C4)-卤代烷氧基、硝基、(C1-C4)-烷基、(C1-C4)-烷氧基、(C1-C4)-烷基磺酰基、(C1-C4)-烷氧基羰基或(C1-C4)-烷基羰基;
RD 3为氢、(C1-C4)-烷基、(C2-C4)-烯基或(C2-C4)-炔基;
RD 4为卤素、硝基、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C1-C4)-卤代烷氧基、(C3-C6)-环烷基、苯基、(C1-C4)-烷氧基、氰基、(C1-C4)-烷硫基、(C1-C4)-烷基亚磺酰基、(C1-C4)-烷基磺酰基、(C1-C4)-烷氧基羰基或(C1-C4)-烷基羰基;
RD 5为氢、(C1-C6)-烷基、(C3-C6)-环烷基、(C2-C6)-烯基、(C2-C6)-炔基、(C5-C6)-环烯基、苯基或含有vD个选自氮、氧和硫的杂原子的3至6元杂环基,其中最后提及的七个基团被vD个选自以下的取代基取代:卤素、(C1-C6)-烷氧基、(C1-C6)-卤代烷氧基、(C1-C2)-烷基亚磺酰基、(C1-C2)-烷基磺酰基、(C3-C6)-环烷基、(C1-C4)-烷氧基羰基、(C1-C4)-烷基羰基和苯基,以及在环状基团的情况下,(C1-C4)-烷基和(C1-C4)-卤代烷基;
RD 6为氢、(C1-C6)-烷基、(C2-C6)-烯基或(C2-C6)-炔基,其中最后提及的三个基团被vD个选自以下的基团取代:卤素、羟基、(C1-C4)-烷基、(C1-C4)-烷氧基和(C1-C4)-烷硫基,或
RD 5和RD 6与带有它们的氮原子一起形成吡咯烷基或哌啶基;
RD 7为氢、(C1-C4)-烷基氨基、二-(C1-C4)-烷基氨基、(C1-C6)-烷基、(C3-C6)-环烷基,其中最后提及的二个基团被vD个选自以下的基团取代:卤素、(C1-C4)-烷氧基、(C1-C6)-卤代烷氧基和(C1-C4)-烷硫基,以及在环状基团的情况下,(C1-C4)-烷基和(C1-C4)-卤代烷基;
nD为0、1或2;
mD为1或2;
vD为0、1、2或3;
其中,优选例如下式(S4a)的N-酰基磺酰胺类的化合物,其由于例如WO-A-97/45016已知,
其中
RD 7为(C1-C6)-烷基、(C3-C6)-环烷基,其中最后提及的二个基团被vD个选自以下的取代基取代:卤素、(C1-C4)-烷氧基、(C1-C6)-卤代烷氧基和(C1-C4)-烷硫基,以及在环状基团的情况下,(C1-C4)-烷基和(C1-C4)-卤代烷基;
RD 4为卤素、(C1-C4)-烷基、(C1-C4)-烷氧基、CF3;
mD为1或2;
vD为0、1、2或3;
和
例如下式(S4b)的酰基氨磺酰基苯甲酰胺,其由例如WO-A-99/16744已知,
例如以下那些,其中
RD 5=环丙基和(RD 4)=2-OMe(“环丙磺酰胺”,S4-1),
RD 5=环丙基和(RD 4)=5-Cl-2-OMe(S4-2),
RD 5=乙基和(RD 4)=2-OMe(S4-3),
RD 5=异丙基和(RD 4)=5-Cl-2-OMe(S4-4),和
RD 5=异丙基和(RD 4)=2-OMe(S4-5)
和
式(S4c)的N-酰基氨磺酰基苯基脲类的化合物,其由例如EP-A-365484已知,
其中
RD 8和RD 9彼此独立地为氢、(C1-C8)-烷基、(C3-C8)-环烷基、(C3-C6)-烯基、(C3-C6)-炔基,
RD 4为卤素、(C1-C4)-烷基、(C1-C4)-烷氧基、CF3,
mD为1或2;
例如
1-[4-(N-2-甲氧基苯甲酰基氨磺酰基)苯基]-3-甲基脲(“metcamifen”,S4-6),
1-[4-(N-2-甲氧基苯甲酰基氨磺酰基)苯基]-3,3-二甲基脲,
1-[4-(N-4,5-二甲基苯甲酰基氨磺酰基)苯基]-3-甲基脲,
和
式(S4d)的N-苯基磺酰基对苯二甲酰胺,其由例如CN 101838227已知,
例如以下那些,其中
RD 4为卤素、(C1-C4)-烷基、(C1-C4)-烷氧基、CF3;
mD为1或2;
RD 5为氢、(C1-C6)-烷基、(C3-C6)-环烷基、(C2-C6)-烯基、(C2-C6)-炔基或(C5-C6)-环烯基。
S5)羟基芳族化合物和芳族-脂族羧酸衍生物类的活性化合物(S5),例如
3,4,5-三乙酰氧基苯甲酸乙酯、3,5-二甲氧基-4-羟基苯甲酸、3,5-二羟基苯甲酸、4-羟基水杨酸、4-氟水杨酸、2-羟基肉桂酸、2,4-二氯肉桂酸,如记载于WO-A-2004/084631、WO-A-2005/015994、WO-A-2005/016001。
S6)1,2-二氢喹喔啉-2-酮类的活性化合物(S6),例如1-甲基-3-(2-噻吩基)-1,2-二氢喹喔啉-2-酮、1-甲基-3-(2-噻吩基)-1,2-二氢喹喔啉-2-硫酮、1-(2-氨基乙基)-3-(2-噻吩基)-1,2-二氢喹喔啉-2-酮盐酸盐、1-(2-甲基磺酰基氨基乙基)-3-(2-噻吩基)-1,2-二氢喹喔啉-2-酮,如记载于WO-A-2005/112630。
S7)式(S7)的化合物,如记载于WO-A-1998/38856,
其中符号和下标定义如下:
RE 1、RE 2各自彼此独立地为卤素、(C1-C4)-烷基、(C1-C4)-烷氧基、(C1-C4)-卤代烷基、(C1-C4)-烷基氨基、二-(C1-C4)-烷基氨基、硝基;
AE为COORE 3或COSRE 4,
RE 3、RE 4各自彼此独立地为氢、(C1-C4)-烷基、(C2-C6)-烯基、(C2-C4)-炔基、氰基烷基、(C1-C4)-卤代烷基、苯基、硝基苯基、苄基、卤代苄基、吡啶基烷基和烷基铵,
nE 1为0或1,
nE 2、nE 3各自独立地为0、1或2,
优选:
二苯基甲氧基乙酸,
二苯基甲氧基乙酸乙酯,
二苯基甲氧基乙酸甲酯(CAS登记号41858-19-9)(S7-1)。
S8)式(S8)的化合物或其盐,如记载于WO-A-98/27049,
其中
XF为CH或N,
nF在XF=N的情况下为0至4的整数,以及在XF=CH的情况下为0至5的整数,
RF 1为卤素、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C1-C4)-烷氧基、(C1-C4)-卤代烷氧基、硝基、(C1-C4)-烷硫基、(C1-C4)-烷基磺酰基、(C1-C4)-烷氧基羰基、任选取代的苯基、任选取代的苯氧基,
RF 2为氢或(C1-C4)-烷基,
RF 3为氢、(C1-C8)-烷基、(C2-C4)-烯基、(C2-C4)-炔基或芳基,其中上述含碳的基团各自为未取代的或被一个或多个,优选最高达三个相同或不同的选自卤素和烷氧基的基团取代。
优选以下化合物或其盐,其中
XF为CH,
nF为0至2的整数,
RF 1为卤素、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C1-C4)-烷氧基、(C1-C4)-卤代烷氧基,
RF 2为氢或(C1-C4)-烷基,
RF 3为氢、(C1-C8)-烷基、(C2-C4)-烯基、(C2-C4)-炔基,或芳基,其中上述含碳的基团各自为未取代的或被一个或多个,优选最高达三个相同或不同的选自卤素和烷氧基的基团取代。
S9)3-(5-四唑基羰基)-2-喹诺酮类的活性化合物(S9),例如
1,2-二氢-4-羟基-1-乙基-3-(5-四唑基羰基)-2-喹诺酮(CAS登记号219479-18-2)、1,2-二氢-4-羟基-1-甲基-3-(5-四唑基羰基)-2-喹诺酮(CAS登记号95855-00-8),如记载于WO-A-1999/000020中。
S10)式(S10a)或(S10b)的化合物,如记载于WO-A-2007/023719和WO-A-2007/023764中,
其中
RG 1为卤素、(C1-C4)-烷基、甲氧基、硝基、氰基、CF3、OCF3,
YG、ZG各自独立地为O或S,
nG为0至4的整数,
RG 2为(C1-C16)-烷基、(C2-C6)-烯基、(C3-C6)-环烷基、芳基、苄基、卤代苄基,
RG 3为氢或(C1-C6)-烷基。
S11)氧基亚氨基化合物类的活性化合物(S11),其已知为拌种剂,例如
“解草腈(oxabetrinil)”((Z)-1,3-二氧戊环-2-基甲氧基亚氨基(苯基)乙腈)(S11-1),其已知为黍/高粱抵抗异丙甲草胺损害的拌种安全剂,
“氟草肟(fluxofenim)”(1-(4-氯苯基)-2,2,2-三氟-1-乙酮O-(1,3-二氧戊环-2-基甲基)肟)(S11-2),其已知为黍/高粱抵抗异丙甲草胺损害的拌种安全剂,
“解草胺腈(cyometrinil)”或“CGA-43089”((Z)-氰基甲氧基亚氨基(苯基)乙腈)(S11-3),其已知为黍/高粱抵抗异丙甲草胺损害的拌种安全剂。
S12)异硫代苯并二氢吡喃酮类的活性化合物(S12),例如[(3-氧代-1H-2-苯并噻喃-4(3H)-亚基)甲氧基]乙酸甲酯(CAS登记号205121-04-6)(S12-1)以及WO-A-1998/13361中的相关化合物。
S13)一种或多种来自(S13)组的化合物:
“萘二甲酸酐”(1,8-萘二甲酸酐)(S13-1),其已知为玉米抵抗硫代氨基甲酸酯除草剂损害的拌种安全剂,
“解草啶(fenclorim)”(4,6-二氯-2-苯基嘧啶)(S13-2),其已知为在播种的稻中用于丙草胺的安全剂,
“解草胺(flurazole)”(2-氯-4-三氟甲基-1,3-噻唑-5-甲酸苄酯)(S13-3),其已知为黍/高粱抵抗甲草胺和异丙甲草胺损害的拌种安全剂,
购自American Cyanamid的“CL 304415”(CAS登记号31541-57-8)(4-羧基-3,4-二氢-2H-1-苯并吡喃-4-乙酸)(S13-4),其已知为玉米抵抗咪唑啉酮损害的安全剂,
购自Nitrokemia的“MG 191”(CAS登记号96420-72-3)(2-二氯甲基-2-甲基-1,3-二氧戊环)(S13-5),其已知为玉米的安全剂,
购自Nitrokemia的“MG 838”(CAS登记号133993-74-5)(1-氧杂-4-氮杂螺[4.5]癸烷-4-二硫代甲酸2-丙烯基酯)(S13-6),
“乙拌磷(disulfoton)”(O,O-二乙基S-2-乙硫基乙基二硫代磷酸酯)(S13-7),
“增效磷(dietholate)”(O,O-二乙基O-苯基硫代磷酸酯)(S13-8),
“mephenate”(甲基氨基甲酸4-氯苯酯)(S13-9)。
S14)除了对有害植物具有除草作用之外,还对作物植物如稻具有安全剂作用的活性化合物,例如
“哌草丹(dimepiperate)”或“MY 93”(1-苯基乙基哌啶-1-硫代甲酸S-1-甲酯),其已知为稻抵抗除草剂草达灭的损害的安全剂,
“杀草隆(daimuron)”或“SK 23”(1-(1-甲基-1-苯基乙基)-3-对甲苯基脲),其已知为稻抵抗唑吡嘧磺隆除草剂损害的安全剂,
“苄草隆(cumyluron)”=“JC 940”(3-(2-氯苯基甲基)-1-(1-甲基-1-苯基乙基)脲,参见JP-A-60087254),其已知为稻抵抗一些除草剂损害的安全剂,
“苯草酮(methoxyphenone)”或“NK 049”(3,3'-二甲基-4-甲氧基苯甲酮),其已知为稻抵抗一些除草剂损害的安全剂,
购自Kumiai的“CSB”(1-溴-4-(氯甲基磺酰基)苯),(CAS登记号54091-06-4),其已知为稻抵抗一些除草剂损害的安全剂。
S15)式(S15)的化合物或其互变异构体,如记载于WO-A-2008/131861和WO-A-2008/131860
其中
RH 1为(C1-C6)-卤代烷基,且
RH 2为氢或卤素,且
RH 3、RH 4各自彼此独立地为氢、(C1-C16)-烷基、(C2-C16)-烯基或(C2-C16)-炔基,
其中后3个基团各自为未取代的或被一个或多个选自以下的基团取代:卤素、羟基、氰基、(C1-C4)-烷氧基、(C1-C4)-卤代烷氧基、(C1-C4)-烷硫基、(C1-C4)-烷基氨基、二[(C1-C4)-烷基]氨基、[(C1-C4)-烷氧基]羰基、[(C1-C4)-卤代烷氧基]羰基、未取代或取代的(C3-C6)-环烷基、未取代或取代的苯基和未取代或取代的杂环基,
或(C3-C6)-环烷基、(C4-C6)-环烯基、在环的一侧稠合至4至6元饱和或不饱和的碳环的(C3-C6)-环烷基,或在环的一侧稠合至4至6元饱和或不饱和的碳环的(C4-C6)-环烯基,
其中最后提及的4个基团各自为未取代的或被一个或多个选自以下的基团取代:卤素、羟基、氰基、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C1-C4)-烷氧基、(C1-C4)-卤代烷氧基、(C1-C4)-烷硫基、(C1-C4)-烷基氨基、二[(C1-C4)-烷基]氨基、[(C1-C4)-烷氧基]羰基、[(C1-C4)-卤代烷氧基]羰基、未取代或取代的(C3-C6)-环烷基、未取代或取代的苯基和未取代或取代的杂环基,
或
RH 3为(C1-C4)-烷氧基、(C2-C4)-烯基氧基、(C2-C6)-炔基氧基或(C2-C4)-卤代烷氧基,且
RH 4为氢或(C1-C4)-烷基,或
RH 3和RH 4与直接键合的氮原子一起为四元至八元杂环,所述杂环除了氮原子之外还可包含其他环杂原子,优选最高达两个选自N、O和S的其他环杂原子,并且所述杂环为未取代的或被一个或多个选自以下的基团取代:卤素、氰基、硝基、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C1-C4)-烷氧基、(C1-C4)-卤代烷氧基和(C1-C4)-烷硫基。
S16)主要用作除草剂但还对作物植物具有安全剂作用的活性化合物,例如
(2,4-二氯苯氧基)乙酸(2,4-D),
(4-氯苯氧基)乙酸,
(R,S)-2-(4-氯-邻甲苯基氧基)丙酸(mecoprop),
4-(2,4-二氯苯氧基)丁酸(2,4-DB),
(4-氯-邻甲苯基氧基)乙酸(MCPA),
4-(4-氯-邻甲苯基氧基)丁酸,
4-(4-氯苯氧基)丁酸,
3,6-二氯-2-甲氧基苯甲酸(dicamba),
3,6-二氯-2-甲氧基苯甲酸1-(乙氧基羰基)乙酯(lactidichlor-ethyl)。
优选的安全剂为:解草酯(cloquintocet-mexyl)、环丙磺酰胺(cyprosulfamide)、解草唑(fenchlorazole-ethyl)、双苯噁唑酸(isoxadifen-ethyl)、吡唑解草酯(mefenpyr-diethyl)、解草啶(fenclorim)、苄草隆(cumyluron)、S4-1和S4-5、mecamifen,特别优选的安全剂为:解草酯(cloquintocet-mexyl)、环丙磺酰胺(cyprosulfamide)、双苯噁唑酸(isoxadifen-ethyl)、吡唑解草酯(mefenpyr-diethyl)和metcamifen。
所述活性化合物由于其除草和植物生长调节性能,因此也可用于防治已知或尚待开发的基因修饰植物作物中的有害植物。一般而言,转基因植物的特征在于其特别有利的性质,例如对某些农药(特别是某些除草剂)具有抗性,对植物病害或植物病害病原体——如某些昆虫或微生物(如真菌、细菌或病毒)——具有抗性。其他特别的性质涉及,例如采收物的数量、质量、存储性、组成和具体成分。例如,已知转基因植物具有增加的淀粉含量或改进的淀粉质量,或其采收物具有不同的脂肪酸组成。其他特别的性质可为对非生物胁迫因子(例如热、低温、干旱、盐和紫外辐射)具有耐受性或抗性。
优选将本发明通式(I)化合物或其盐用于经济上重要的有用植物和观赏植物的转基因作物中,所述作物例如谷类,如小麦、大麦、黑麦、燕麦、高粱、粟、稻、木薯和玉米,或甜菜、棉花、大豆、油菜、马铃薯、番茄、豌豆及其他蔬菜的作物。
优选在对除草剂的植物毒性效果具有抗性或已通过重组方式产生抗性的有用植物作物中使用通式(I)的化合物作为除草剂。
产生与现有植物相比具有改进性能的新植物的常规方法包括例如常规育种方法和产生突变体方法。或者,具有改进特性的新植物可借助重组方法产生(参见例如,EP-A-0221044、EP-A-0131624)。例如,在多个案例中已描述以下情况:
-基因修饰作物植物,使植物中合成的淀粉改性(例如WO 92/11376、WO 92/14827、WO 91/19806),
-对某些草铵磷(glufosinate)类除草剂(参见例如EP 0242236、EP0242246)或草甘膦(gluphosate)类除草剂(WO 92/00377)或磺酰脲类除草剂(EP 0257993、US 5013659)具有抗性的转基因作物植物,
-能产生苏云金杆菌毒素(Bt毒素)从而对某些害虫具有抗性的转基因作物植物,例如棉花(EP 0142924、EP 0193259),
-具有改变的脂肪酸组成的转基因作物植物(WO 91/13972),
-具有新成分或次级代谢产物,例如能够带来增强的抗病能力的新的植物抗毒素的基因修饰作物植物(EP 309862、EP0464461),
-具有减少的光呼吸的基因修饰植物,其具有较高的产量和较高的胁迫耐受性(EP0305398),
-生产药用或诊断用的重要蛋白质的转基因作物植物(“分子农场”)
-具有更高产量或更好品质的转基因作物,
-特征在于具有例如上述新性能的组合(“基因叠加”)的转基因作物。
许多能够制备具有改进性质的新转基因植物的分子生物技术原则上是已知的,参见例如I.Potrykus和G.Spangenberg(编)Gene Transfer to Plants,Springer LabManual(1995),Springer Verlag Berlin,Heidelberg。或者Christou,"Trends in PlantScience"1(1996)423-431。
为了进行这类基因操作,可以将能够产生突变或通过重组DNA序列产生序列改变的核酸分子引入质粒。借助于标准方法,可以例如进行碱基取代、可以移除部分序列或加入天然的或合成的序列。为了将DNA片段彼此连接,可以在片段上添加接头(adapter)或连接体(linker)。参见例如,Sambrook等人,1989,Molecular Cloning,A Laboratory Manual,第二版,Cold Spring Harbor Laboratory Press,Cold Spring Harbor,NY;或Winnacker"Gene und Klone"[基因和克隆],VCH Weinheim第二版,1996。
例如,基因产物活性降低的植物细胞的产生可以通过下列方法实现:通过表达至少一种相应的反义RNA、用于实现共抑制效应的正义RNA,或者通过表达至少一种能够特异性切割上述基因产物的转录物并具有合适结构的核酶。
为此目的,可以首先使用包括基因产物的完整编码序列——包括所有可能存在的侧翼序列——的DNA分子,也可以使用仅含有部分编码序列的DNA分子,在这种情况下,所述部分编码序列必须足够长,以便在细胞中产生反义效果。也可以使用与所述基因产物的编码序列具有高度同源性但并不完全相同的DNA序列。
当在植物中表达核酸分子时,所合成的蛋白可被定位至植物细胞的任何所需的区室中。然而,为了实现在某一区室中的定位,可以例如将编码区与确保在某一区室中定位的DNA序列相连接。这种序列是本领域中技术人员已知的(参见例如Braun等人,EMBO J.11(1992),3219-3227;Wolter等人,Proc.Natl.Acad.Sci.USA 85(1988),846-850;Sonnewald等人,Plant J.1(1991),95-106)。核酸分子也可以在植物细胞中的细胞器中表达。
可以使用已知的技术使转基因植物细胞再生为完整的植物。原则上,所述转基因植物可为任何所需的植物品种,即既可为单子叶植物,也可为双子叶植物。
因此,可以通过对同源(即天然)基因或基因序列的过表达、阻遏或抑制,或者通过异源(即外源)基因或基因序列的表达而获得性质改变的转基因植物。
优选将本发明通式(I)的化合物用于转基因作物中,所述转基因作物对生长调节剂例如麦草畏具有抗性,或者对抑制重要的植物酶(例如乙酰乳酸合成酶(ALS)、5-烯醇式丙酮酰莽草酸-3-磷酸(EPSP)合成酶、谷氨酰胺合成酶(GS)或羟基苯丙酮酸双加氧酶(HPPD))的除草剂具有抗性,或者对选自磺酰脲、草甘膦、草铵磷或苯甲酰基异噁唑以及类似的活性化合物的除草剂具有抗性。
当将本发明通式(I)的活性化合物用于转基因作物时,除了可在其他作物中观察到的对于有害植物的效果之外,还经常发现施用于特定转基因作物的特殊的效果,例如改变或特别是拓宽的可防治的杂草谱、改进的施用时可以使用的施用率、与转基因作物对其有抗性的除草剂的更良好的相容性,以及对转基因作物植物的生长和产量的影响。
因此,本发明还涉及本发明通式(I)的化合物作为除草剂用于防治转基因作物中的有害植物的用途。
根据所需的生物学和/或物理化学参数,可通过多种方式配制通式(I)的化合物。可能的剂型包括例如:可湿性粉剂(WP)、水溶性粉剂(SP)、水溶性浓缩剂、乳油(EC)、乳剂(EW)例如水包油乳剂和油包水乳剂、可喷洒性溶液剂、悬浮浓缩剂(SC)、油基分散剂或水基分散剂、油混溶性溶液剂、胶囊悬浮剂(CS)、撒粉剂(DP)、拌种产品、用于撒播和土壤施用的颗粒剂、微颗粒形式的颗粒剂(GR)、喷洒颗粒剂、吸附剂和吸附颗粒剂、水分散性颗粒剂(WG)、水溶性颗粒剂(SG)、ULV制剂、微胶囊剂和蜡剂。
这些制剂的各个类型原则上都是已知的,并在下列文献中有所描述,例如:Winnacker-Küchler,“Chemische Technologie”[Chemical Technology],第7卷,C.HauserVerlag Munich,第4版,1986;Wade van Valkenburg,“Pesticide Formulations”,MarcelDekker,N.Y.,1973;K.Martens,“Spray Drying”Handbook,第3版.1979,G.GoodwinLtd.London。
必需的制剂助剂,例如惰性物质、表面活性剂、溶剂和其他添加剂同样也是已知的,并在下列文献中有所描述,例如:Watkins,"Handbook of Insecticide Dust Diluentsand Carriers",第二版,Darland Books,Caldwell N.J.;H.v.Olphen,"Introduction toClay Colloid Chemistry";第二版,J.Wiley&Sons,N.Y.;C.Marsden,"Solvents Guide";第二版,Interscience,N.Y.1963;McCutcheon's"Detergents and Emulsifiers Annual",MC Publ.Corp.,Ridgewood N.J.;Sisley and Wood,"Encyclopedia of Surface ActiveAgents",Chem.Publ.Co.Inc.,N.Y.1964; [Interface-active ethylene oxide adducts],Wiss.Verlagsgesell.,Stuttgart1976;Winnacker-Küchler,"Chemische Technologie[化学技术]",第7卷,C.Hanser VerlagMunich,第四版,1986。
基于这些制剂,可以生产与其它农药活性化合物——例如杀昆虫剂、杀螨剂、除草剂和杀菌剂——以及与安全剂、肥料和/或生长调节剂的结合物,例如以成品制剂或桶混形式。
可湿性粉剂为可均匀分散于水中的制剂,其除了含有活性化合物和稀释剂或惰性物质之外,还含有离子型表面活性剂和/或非离子型表面活性剂(湿润剂、分散剂),例如聚乙氧基化烷基酚、聚乙氧基化脂肪醇、聚乙氧基化脂肪胺、脂肪醇聚乙二醇醚硫酸盐、烷基磺酸盐、烷基苯磺酸盐、木素磺酸钠、2,2’-二萘基甲烷-6,6’-二磺酸钠、二丁基萘磺酸钠或油酰基甲基牛磺酸钠。为了制备可湿性粉剂,例如在常规设备例如锤磨机、鼓风磨机和喷气磨机中精细研磨具有除草活性的化合物,并同时或随后与制剂助剂相混合。
悬乳浓缩剂通过下述过程制备:将活性化合物溶于有机溶剂(例如丁醇、环己酮、二甲基甲酰胺、二甲苯或相对高沸点的芳族化合物或烃类)或有机溶剂混合物中,并加入一种或多种离子型和/或非离子型表面活性剂(乳化剂)。可使用的乳化剂的实例为烷基芳基磺酸钙盐,例如十二烷基苯磺酸钙;或非离子型乳化剂,例如脂肪酸聚乙二醇酯、烷基芳基聚乙二醇醚、脂肪醇聚乙二醇醚、环氧丙烷-环氧乙烷缩合物、烷基聚醚、山梨聚糖酯,例如山梨聚糖脂肪酸酯或聚氧乙烯山梨聚糖酯例如聚氧乙烯山梨聚糖脂肪酸酯。
粉剂可通过将活性化合物与细分散的固体物质一起研磨而制备,所述固体物质为例如滑石、天然粘土(例如高岭土、膨润土和叶蜡石)或硅藻土。
悬浮浓缩剂可为水基或油基的。它们可以通过例如使用标准市售的球磨机湿法研磨和任选地加入上文所列的例如用于其他剂型的表面活性剂而制备。
乳剂例如水包油乳剂(EW),可以使用例如搅拌器、胶体磨机和/或静态混合器制备,使用水性有机溶剂以及上文所列的例如用于其他剂型的任选地表面活性剂。
颗粒剂可以通过将所述活性化合物喷洒在能够吸附的颗粒状惰性物质上、或通过使用粘合剂将活性化合物浓缩物施用到载体表面而制备,所述载体为例如砂、高岭土或颗粒状惰性材料,所述粘合剂为例如聚乙烯醇、聚丙烯酸钠或矿物油。合适的活性化合物也可以以制备肥料颗粒的常规方式制备成颗粒——如果需要,可以制备为与肥料的混合物。
通常通过常规方法制备水分散性颗粒剂,所述常规方法为例如喷雾干燥法、流化床制粒法、盘式制粒法、使用高速混合器的混合法以及不使用固体惰性物质的挤出法。
关于盘式颗粒、流化床颗粒、挤出法颗粒和喷雾法颗粒的制备,参见例如:"Spray-Drying Handbook"第三版,1979,G.Goodwin Ltd.,London;J.E.Browning,"Agglomeration",Chemical and Engineering1967,第147页及后文;"Perry's ChemicalEngineer's Handbook",第5版,McGraw-Hill,New York 1973,第8-57页中的方法。
关于作物保护试剂的剂型的更多细节,参见例如G.C.Klingman,“Weed Controlas a Science”,John Wiley and Sons.,Inc.,New York,1961,81-96页;和J.D.Freyer,S.A.Evans,“Weed Control Handbook”,第5版,Blackwell Scientific Publications,Oxford,1968,第101-103页。
所述农业化学制剂通常含有0.1至99重量%、尤其是0.1至95重量%的式(I)的活性化合物。
在可湿性粉剂中,活性化合物的浓度例如为约10至90重量%,至100重量%的剩余部分由常规制剂组分组成。在乳油中,活性化合物的浓度可为约1至90重量%,优选地为5至80重量%。粉剂形式的制剂中含有1至30重量%的活性化合物,优选地通常含有5至20重量%的活性化合物;可喷洒溶液剂中含有约0.05至80重量%、优选地为2至50重量%的活性化合物。在水分散性颗粒剂的情况下,活性化合物的含量部分地取决于所述活性化合物以液体形式还是固体形式存在,以及所使用的粒化助剂、填料等。在水分散性颗粒剂中,活性化合物的含量例如为1至95重量%,优选地为10至80重量%。
此外,所述活性化合物的制剂中任选含有各自常用的粘合剂、润湿剂、分散剂、乳化剂、渗透剂、防腐剂、抗冻剂和溶剂、填料、载体和着色剂、消泡剂、蒸发抑制剂、影响pH和粘度的试剂。
通式(I)的化合物或其盐可以自身使用或其与其它农药活性物质——例如杀昆虫剂、杀螨剂、除草剂、杀真菌剂、安全剂、肥料和/或生长调节剂——结合的制剂形式使用,例如以成品制剂或桶混物的形式。
为了使用,如果合适,将以市售形式的制剂以常规方式稀释,如在可湿性粉剂、乳油、分散剂、水分散性颗粒剂的情况下用水稀释。粉剂、用于土壤施用的颗粒剂、用于播撒的颗粒剂和可喷洒溶液剂在施用前通常不用其他惰性物质进一步稀释。
式(I)的化合物及其盐所需的施用率随外界条件变化,尤其是如温度、湿度和所使用的除草剂的类型。其可在较宽的范围内变化,例如在0.001和10.0kg/ha之间或更多的活性物质,然而,优选0.005至5kg/ha,更优选0.01至1.5kg/ha,特别优选0.05至1kg/ha g/ha。这同时适用于苗前和苗后施用。
通过下面的实施例详细说明本发明,但是这些实施例不以任何方式限制本发明。
A.合成实施例
1-(2-{[(1R,2S)-2,6-二甲基-2,3-二氢-1H-茚-1-基]氨基}-4-甲基嘧啶-5-基)乙醇(实施例1.7)
1.在0℃下,将溶于40mL三氯甲烷的1.946g(8.231mmol)间氯过氧苯甲酸滴加至0.750g(4.115mmol)1-[4-甲基-2-(甲硫基)嘧啶-5-基]乙酮于35mL三氯甲烷中的溶液。将混合物在20℃下搅拌1小时,依次加入2.290g(22.634mmol)三乙胺和溶于10mL三氯甲烷中的0.730g(4.527mmol)(1R,2S)-2,6-二甲基茚-1-胺。将混合物在50℃下搅拌1.5小时,加入水和二氯甲烷,水相用二氯甲烷萃取两次。合并的有机相用硫酸钠干燥,然后减压除去溶剂,将残余物溶于乙腈中。过滤出不溶的残余物(3-氯苯甲酸),然后在减压下除去溶剂,通过色谱法[开始:乙酸乙酯/正庚烷(5:95),25分钟后变为乙酸乙酯/正庚烷(30:70)]纯化残余物,得到0.853g(70%)1-(2-{[(1R,2S)-2,6-二甲基-2,3-二氢-1H-茚-1-基]氨基}-4-甲基嘧啶-5-基)乙酮。
2.将0.327g(8.633mmol)硼氢化钠每次少许地加入0.850g(2.878mmol)1-(2-{[(1R,2S)-2,6-二甲基-2,3-二氢-1H-茚-1-基]氨基}-4-甲基嘧啶-5-基)乙酮于10mL乙醇中的溶液,将混合物在0℃下搅拌2小时。使用2M的盐酸酸化反应混合物,减压除去溶剂。向残余物中加入水和二氯甲烷,加入碳酸钠水溶液,将混合物在20℃下搅拌5分钟,水相用二氯甲烷萃取两次。合并的有机相用硫酸钠干燥,然后在减压下除去溶剂,通过色谱法[开始:乙酸乙酯/正庚烷(5:95),15分钟后变为乙酸乙酯/正庚烷(35:65)]纯化残余物,得到0.715g(84%)的1-(2-{[(1R,2S)-2,6-二甲基-2,3-二氢-1H-茚-1-基]氨基}-4-甲基嘧啶-5-基)乙醇(实施例1.7)。
2-{2-[(1R)-1,2,3,4-四氢萘-1-基氨基]嘧啶-5-基}丙-2-醇(实施例1.8)
1.在0℃下,将溶于35mL三氯甲烷的4.309g(24.969mmol)间氯过氧苯甲酸滴加至2.200g(11.097mmol)2-(甲硫基)嘧啶-5-甲酸乙酯于30mL三氯甲烷中的溶液。将混合物在0-5℃下搅拌0.5小时,依次加入11.474g(88.779mmol)N,N-二异丙基乙胺和溶于10mL三氯甲烷的1.634g(11.097mmol)(1R)-1,2,3,4-四氢萘-1-胺。将混合物在40℃下搅拌4小时,加入水和二氯甲烷,水相用二氯甲烷萃取两次。合并的有机相用硫酸钠干燥,然后减压除去溶剂,将残余物溶于乙腈中。过滤掉不溶的残余物(3-氯苯甲酸),然后减压除去溶剂,得到2.763g(84%)2-[(1R)-1,2,3,4-四氢萘-1-基氨基]嘧啶-5-甲酸乙酯,其无需进一步纯化而用于下一步反应。
2.在0℃下,将2.396mL(4.792mmol)甲基溴化镁(在2-甲基四氢呋喃中的2摩尔溶液)加入至0.500g(1.682mmol)2-[(1R)-1,2,3,4-四氢萘-1-基氨基]嘧啶-5-甲酸乙酯于7.5mL干燥四氢呋喃中的溶液,在55℃下,将混合物在氮气气氛下搅拌5小时。将反应混合物冷却至0℃,滴加30mL THF/水(4:1)的溶剂混合物,将混合物用乙酸乙酯萃取三次。合并的有机相用硫酸钠干燥,然后在减压下蒸馏掉溶剂,通过色谱法[开始:乙酸乙酯/正庚烷(5:95),25分钟后变为乙酸乙酯/正庚烷(65:35)]纯化残余物,得到0.122g(26%)的2-{2-[(1R)-1,2,3,4-四氢萘-1-基氨基]嘧啶-5-基}丙-2-醇(实施例1.8)。
2-(2-{[(1R,2S)-2,6-二甲基-2,3-二氢-1H-茚-1-基]氨基}嘧啶-5-基)丁-3-烯-2-醇(实施例1.15)
1.在微波炉中,将1.000g(6.387mmol)1-(2-氯嘧啶-5-基)乙酮、1.236g(7.664mmol)(1R,2S)-2,6-二甲基茚-1-胺和2.476g(19.161mmol)N,N-二异丙基乙胺于8.0mL 1,4-二氧六环中的混合物在140℃下加热45分钟。在减压下除去溶剂,将水和二氯甲烷加入到混合物中,水相用二氯甲烷萃取两次。合并的有机相用硫酸钠干燥,在减压下蒸馏掉溶剂,通过色谱法[开始:乙酸乙酯/正庚烷(5:95),25分钟后变为乙酸乙酯/正庚烷(50:50)]纯化残余物,得到1.630g(85%)1-(2-{[(1R,2S)-2,6-二甲基-2,3-二氢-1H-茚-1-基]氨基}嘧啶-5-基)乙酮。
2.在0℃下,将在4.5mL干燥的四氢呋喃中的0.260g(0.924mmol)的1-(2-{[(1R,2S)-2,6-二甲基-2,3-二氢-1H-茚-1-基]氨基}嘧啶-5-基)乙酮加入至1.617mL(1.617mmol)的溴化(乙烯基)镁(在四氢呋喃中的1摩尔溶液)的溶液,在20℃下,将混合物在氮气气氛下搅拌1.5小时。向混合物中滴加饱和的氯化铵水溶液,然后水相用乙酸乙酯萃取三次。合并的有机相用硫酸钠干燥,然后在减压下蒸馏掉溶剂,通过色谱法[开始:乙酸乙酯/正庚烷(5:95),30分钟后变为乙酸乙酯/正庚烷(50:50)]纯化残余物,得到0.066g(23%)2-(2-{[(1R,2S)-2,6-二甲基-2,3-二氢-1H-茚-1-基]氨基}嘧啶-5-基)丁-3-烯-2-醇(实施例1.15)。
所选实施例的NMR数据
NMR峰列表方法
所选实例的1H-NMR数据以1H-NMR峰列表的形式表示。对于每个信号峰,首先列出以ppm计的δ值,然后在圆括号内列出信号强度。对于不同的信号峰,一对δ值-信号强度数通过分号彼此间隔列出。
因此,一个实例的峰列表具有以下形式:
δ1(强度1);δ2(强度2);...;δi(强度i);...;δn(强度n)
在NMR谱的打印实例中,尖峰信号的强度与以厘米计的信号高度相关,并且显示出信号强度的真实比例。对于宽峰信号,可以显示数个峰或信号的中间部分以及它们与谱图中最强信号相比的相对强度。
为了校准1H NMR谱的化学位移,使用四甲基硅烷和/或溶剂的化学位移,特别是在DMSO中测量的谱图的情况下。因此,四甲基硅烷峰可以但不是必须出现在NMR峰列表中。
1H NMR峰的列表类似于常规1H NMR打印件,因此,其通常含有在常规NMR说明中列出的所有峰。
另外,如同常规1H NMR打印件,它们可显示出溶剂信号、目标化合物的立体异构体(其同样构成本发明的主题的一部分)的信号,和/或杂质的峰。
在记录在溶剂和/或水的δ范围内的化合物信号时,1H NMR峰列表显示出常见的溶剂峰,例如在DMSO-D6中DMSO的峰以及水的峰,其通常平均具有高强度。
平均来看,目标化合物的立体异构体的峰和/或杂质的峰通常具有比目标化合物(例如具有>90%的纯度)的峰更低的强度。
此类立体异构体和/或杂质对于特定的制备方法可以是特有的。因此,通过参考“副产品指纹”,它们的峰可有助于鉴定制备方法的重现性。
专业人员通过已知方法(MestreC,ACD模拟,以及凭经验评估的预期值)计算目标化合物的峰,并且视需要可以任选地使用另外的强度滤波器来分离目标化合物的峰。这种分离类似于在常规1H NMR说明中相关峰的挑选。
1H NMR峰列表的其他详情可在Research Disclosure Database Number 564025中找到。
B.制剂实施例
撒粉剂通过以下方式获得:将10重量份式(I)的化合物和/或其盐与90重量份作为惰性物质的滑石进行混合并在锤磨机中粉碎该混合物。
b)易分散于水中的可湿性粉剂通过以下方式获得:将25重量份式(I)的化合物和/或其盐、64重量份作为惰性物质的含高岭土的石英、10重量份木质素磺酸钾和1重量份作为润湿剂和分散剂的油酰基甲基牛磺酸钠进行混合,并将该混合物在销盘研磨机中研磨。
c)易分散于水中的分散浓缩剂通过以下方式获得:将20重量份式(I)的化合物和/或其盐与6重量份烷基酚聚乙二醇醚(X 207)、3重量份异十三烷醇聚乙二醇醚(8EO)和71重量份石蜡矿物油(沸程为例如约255至高于277℃)进行混合,并将该混合物在球磨机中研磨至细度低于5微米。
d)乳油由15重量份式(I)的化合物和/或其盐、75重量份作为溶剂的环己酮和10重量份作为乳化剂的乙氧基化壬基酚得到。
e)水分散性颗粒剂通过以下方式获得:将下述组分混合、将该混合物在销盘研磨机中研磨,并在流化床中通过喷雾作为制粒液体的水而粒化所述粉末:
75重量份式(I)的化合物和/或其盐,
10重量份木质素磺酸钙,
5重量份月桂基硫酸钠,
3重量份聚乙烯醇,和
7重量份的高岭土。
f)水分散性颗粒剂也可通过以下方式获得:在胶体磨中均化并预粉碎下述组分、随后在砂磨机中研磨并将所得到的悬浮液在喷雾塔中使用单相喷嘴进行雾化并干燥:
25重量份式(I)的化合物和/或其盐、
5重量份的2,2'-二萘基甲烷-6,6'-二磺酸钠、
2重量份油酰基甲基牛磺酸钠、
1重量份聚乙烯醇、
17重量份碳酸钙和
50重量份水。
C.生物实施例
试验的描述
1.苗前除草功效和作物植物相容性
将单子叶或双子叶杂草植物或作物植物的种子置于塑料或木质纤维盆中,并用土覆盖。然后将配制为可湿性粉剂(WP)或乳油(EC)形式的本发明化合物在添加0.5%添加剂的情况下,以水性悬浮液或乳液的形式在600L/ha(经换算)的水施用率下施用至覆盖土的表面。
在处理后,将盆置于温室中,并使之保持在对测试植物而言良好的生长条件下。在约3周之后,通过与未处理的对照相比,目测评估以百分比计的制剂的功效。例如,100%活性=植物已死亡;0%活性=与对照植物相同。
在下表中使用以下缩写:
不期望的植物/杂草:
表6苗前活性(除草作用[%])
表7苗前活性(除草作用[%])
如上述结果所示,表6和表7中的本发明的化合物在苗前施用时,其对有害植物具有良好的除草活性。
通过苗前法施用的本发明化合物在施用率为0.32kg或更少的活性物质/公顷时,其对有害植物具有非常好的活性(80%至100%的除草活性),所述有害植物为例如苘麻(Abutilon theophrasti)、大穗看麦娘(Alopecurus myosuroides)、反枝苋(Amaranthusretroflexus)、野燕麦(Avena fatua)、稗草(Echinochloa crus galli)、鼠大麦(Hordeummurinum)、硬直黑麦草(Lolium rigidum)、淡甘菊(Matricaria inodora)、圆叶牵牛(Ipomoea purpurea)、卷茎蓼(Polygonum convolvulus)、狗尾草(Setaria viridis)、繁缕(Stellaria media)、***婆婆纳(Veronica persica)和三色堇(Viola tricolor)。同时,本发明的化合物在苗前施用时,甚至在高的活性成分剂量下,对禾本科作物也没有可见的损害,所述禾本科作物为例如大麦、小麦、黑麦、黍/高粱、玉米或稻。另外,某些物质对双子叶作物也无害,例如大豆、棉花、油菜、甜菜或马铃薯。
本发明的某些化合物显示出高的选择性并因此适用于通过苗前法防治农业作物中不希望的植物。
2.苗后除草功效和作物植物相容性
在塑料或木质纤维盆中,将单子叶和双子叶杂草以及作物植物的种子置于沙质壤土中,用土壤覆盖并在受控的生长条件下于温室中培养。在播种两到三周后,在单叶阶段处理测试植物。然后将配制为可湿性粉剂(WP)或乳油(EC)的本发明化合物在添加0.5%的添加剂的情况下,以水性悬浮液或乳液的形式在600L/ha(经换算)的水施用率下喷洒至植物的绿色部位。在将测试植物在最佳生长条件下置于温室中约3周后,通过与未处理的对照比较,目测评估制剂的活性。例如,100%活性=植物已死亡,0%活性=与对照植物相同。
表8苗后活性(除草作用[%])
表9苗后活性(除草作用[%])
如上述结果所示,表8和表9中的本发明化合物在苗后施用时,其对有害植物具有良好的除草活性。
通过苗后法施用的本发明化合物在施用率为0.32kg或更少的活性物质/公顷时,其对有害植物具有非常好的除草活性(80%至100%的除草活性),所述有害植物为例如苘麻(Abutilon theophrasti)、大穗看麦娘(Alopecurus myosuroides)、反枝苋(Amaranthusretroflexus)、野燕麦(Avena fatua)、稗草(Echinochloa crus galli)、鼠大麦(Hordeummurinum)、硬直黑麦草(Lolium rigidum)、淡甘菊(Matricaria inodora)、圆叶牵牛(Ipomoea purpurea)、卷茎蓼(Polygonum convolvulus)、狗尾草(Setaria viridis)、繁缕(Stellaria media)、***婆婆纳(Veronica persica)和三色堇(Viola tricolor)。同时,本发明的化合物在苗后施用时,甚至在高的活性成分剂量下,对禾本科作物也没有可见的损害,所述禾本科作物为例如大麦、小麦、黑麦、黍/高粱、玉米或稻。另外,某些物质对双子叶作物也无害,例如大豆、棉花、油菜、甜菜或马铃薯。本发明的某些化合物具有高的选择性并因此适用于通过苗后法防治农业作物中不希望的植物。
Claims (28)
1.通式(I)的化合物及其农业化学上可接受的盐,
其中
R1a选自
-氢、氰基、CO(O)H、C(O)NH2;
-(C1-C6)-烷基、(C1-C6)-卤代烷基、(C1-C6)-烷基羰基-(C1-C4)-烷基;
-(C1-C6)-烷氧基羰基-(C1-C6)-烷基、(C1-C6)-卤代烷氧基羰基-(C1-C6)-烷基、(C1-C6)-烷氧基羰基-(C1-C6)-卤代烷基、(C1-C6)-卤代烷氧基羰基-(C1-C6)-卤代烷基;
-(C2-C6)-烯基、(C2-C6)-卤代烯基;
-(C2-C6)-炔基、(C2-C6)-卤代炔基;
-(C6-C14)-芳基,其芳基部分在每种情况下可被卤素、(C1-C6)-烷基和/或(C1-C6)-卤代烷基取代;
-吡啶基,其在每种情况下可被卤素、(C1-C6)-烷基和/或(C1-C6)-卤代烷基取代;
-噻吩基,其在每种情况下可被卤素、(C1-C6)-烷基和/或(C1-C6)-卤代烷基取代;
-(C6-C14)-芳基-(C1-C6)-烷基,其芳基部分在每种情况下可被卤素、(C1-C6)-烷基和/或(C1-C6)-卤代烷基取代;
-氨基羰基-(C1-C6)-烷基;
-(C1-C6)-烷氧基-(C1-C6)-烷基;
-(C3-C8)-环烷基,其环烷基可为未取代的或被(C1-C6)-烷基和/或卤素单取代或多取代;(C3-C8)-环烷基-(C1-C6)-烷基、(C3-C8)-环烷基-(C1-C6)-卤代烷基;
-(C3-C8)-环烯基、(C3-C8)-环烯基-(C1-C6)-烷基、(C3-C8)-环烯基-(C1-C6)-卤代烷基;
-羟基-(C1-C6)-烷基、氨基-(C1-C6)-烷基、氰基-(C1-C6)-烷基;
-(C1-C6)-烷基磺酰基-(C1-C6)-烷基、(C1-C6)-烷硫基-(C1-C6)-烷基、(C1-C6)-烷基亚磺酰基-(C1-C6)-烷基、(C1-C6)-卤代烷基磺酰基-(C1-C6)-烷基、(C1-C6)-卤代烷硫基-(C1-C6)-烷基、(C1-C6)-卤代烷基亚磺酰基-(C1-C6)-烷基、(C1-C6)-烷基磺酰基-(C1-C6)-卤代烷基、(C1-C6)-烷硫基-(C1-C6)-卤代烷基、(C1-C6)-烷基亚磺酰基-(C1-C6)-卤代烷基、(C1-C6)-卤代烷基磺酰基-(C1-C6)-卤代烷基、(C1-C6)-卤代烷硫基-(C1-C6)-卤代烷基、(C1-C6)-卤代烷基亚磺酰基-(C1-C6)-卤代烷基;
R1b选自
-氰基、C(O)OH、C(O)NH2;
-(C1-C6)-烷基、(C1-C6)-卤代烷基、(C1-C6)-烷基羰基-(C1-C4)-烷基;
-(C1-C6)-烷氧基羰基-(C1-C6)-烷基、(C1-C6)-卤代烷氧基羰基-(C1-C6)-烷基、(C1-C6)-烷氧基羰基-(C1-C6)-卤代烷基、(C1-C6)-卤代烷氧基羰基-(C1-C6)-卤代烷基;
-(C2-C6)-烯基、(C2-C6)-卤代烯基;
-(C2-C6)-炔基、(C2-C6)-卤代炔基;
-(C6-C14)-芳基,其芳基部分在每种情况下可被卤素、(C1-C6)-烷基和/或(C1-C6)-卤代烷基取代;
-吡啶基,其在每种情况下可被卤素、(C1-C6)-烷基和/或(C1-C6)-卤代烷基取代;
-噻吩基,其在每种情况下可被卤素、(C1-C6)-烷基和/或(C1-C6)-卤代烷基取代;
-(C6-C14)-芳基-(C1-C6)-烷基,其芳基部分在每种情况下可被卤素、(C1-C6)-烷基和/或(C1-C6)-卤代烷基取代;
-氨基羰基-(C1-C6)-烷基;
-(C1-C6)-烷氧基-(C1-C6)-烷基;
-(C3-C8)-环烷基,其环烷基可为未取代的或被(C1-C6)-烷基和/或卤素单取代或多取代;(C3-C8)-环烷基-(C1-C6)-烷基、(C3-C8)-环烷基-(C1-C6)-卤代烷基;
-(C3-C8)-环烯基、(C3-C8)-环烯基-(C1-C6)-烷基、(C3-C8)-环烯基-(C1-C6)-卤代烷基;
-羟基-(C1-C6)-烷基、氨基-(C1-C6)-烷基、氰基-(C1-C6)-烷基;
-(C1-C6)-烷基磺酰基-(C1-C6)-烷基、(C1-C6)-烷硫基-(C1-C6)-烷基、(C1-C6)-烷基亚磺酰基-(C1-C6)-烷基、(C1-C6)-卤代烷基磺酰基-(C1-C6)-烷基、(C1-C6)-卤代烷硫基-(C1-C6)-烷基、(C1-C6)-卤代烷基亚磺酰基-(C1-C6)-烷基、(C1-C6)-烷基磺酰基-(C1-C6)-卤代烷基、(C1-C6)-烷硫基-(C1-C6)-卤代烷基、(C1-C6)-烷基亚磺酰基-(C1-C6)-卤代烷基、(C1-C6)-卤代烷基磺酰基-(C1-C6)-卤代烷基、(C1-C6)-卤代烷硫基-(C1-C6)-卤代烷基、(C1-C6)-卤代烷基亚磺酰基-(C1-C6)-卤代烷基;
其中,如果R1a不代表氢,则R1a通过化学键与R1b相连,使得它们与这两个基团所连接的碳一起形成饱和或不饱和的3至7元的碳环或杂环,该碳环或杂环为未取代的或被一个或多个选自以下的取代基取代:(C1-C6)-烷基、(C1-C6)-卤代烷基、(C3-C8)-环烷基、螺环-(C3-C8)-环烷基;
R2a和R2b在每种情况下彼此独立地选自
-氢、卤素、羟基、氰基、C(O)OH、C(O)NH2;
-(C1-C6)-烷基、(C1-C6)-卤代烷基、(C1-C6)-烷基羰基、(C1-C6)-卤代烷基羰基、(C1-C6)-烷基羰基氧基、(C1-C6)-卤代烷基羰基氧基、(C1-C6)-烷基羰基-(C1-C4)-烷基;
-(C1-C6)-烷氧基、(C1-C6)-卤代烷氧基、(C1-C6)-烷氧基羰基、(C1-C6)-卤代烷氧基羰基、(C1-C6)-烷氧基羰基-(C1-C6)-烷基、(C1-C6)-卤代烷氧基羰基-(C1-C6)-烷基、(C1-C6)-烷氧基羰基-(C1-C6)-卤代烷基、(C1-C6)-卤代烷氧基羰基-(C1-C6)-卤代烷基;
-(C2-C6)-烯基、(C2-C6)-卤代烯基、(C2-C6)-烯基羰基、(C2-C6)-卤代烯基羰基、(C2-C6)-烯基氧基、(C2-C6)-卤代烯基氧基、(C2-C6)-烯基氧基羰基、(C2-C6)-卤代烯基氧基羰基;
-(C2-C6)-炔基、(C2-C6)-卤代炔基、(C2-C6)-炔基羰基、(C2-C6)-卤代炔基羰基、(C2-C6)-炔基氧基、(C2-C6)-卤代炔基氧基、(C2-C6)-炔基氧基羰基、(C2-C6)-卤代炔基氧基羰基、三-(C1-C6)-烷基甲硅烷基-(C2-C6)-炔基、二-(C1-C6)-烷基甲硅烷基-(C2-C6)-炔基、单-(C1-C6)-烷基甲硅烷基-(C2-C6)-炔基、苯基甲硅烷基-(C2-C6)-炔基;
-(C6-C14)-芳基、(C6-C14)-芳基氧基、(C6-C14)-芳基羰基和(C6-C14)-芳基氧基羰基,其各自芳基部分可被卤素、(C1-C6)-烷基和/或(C1-C6)-卤代烷基取代;
-(C6-C14)-芳基-(C1-C6)-烷基、(C6-C14)-芳基-(C1-C6)-烷氧基、(C6-C14)-芳基-(C1-C6)-烷基羰基、(C6-C14)-芳基-(C1-C6)-烷基羰基氧基、(C6-C14)-芳基-(C1-C6)-烷氧基羰基、(C6-C14)-芳基-(C1-C6)-烷氧基羰基氧基;
-氨基羰基-(C1-C6)-烷基、二-(C1-C6)-烷基氨基羰基-(C1-C6)-烷基;
-N-((C1-C6)-卤代烷酰基)-氨基羰基、单-((C1-C6)-芳基)-氨基羰基、二-((C1-C6)-芳基)-氨基羰基;
-(C1-C6)-烷氧基-(C1-C6)-烷基、(C1-C6)-烷氧基-(C1-C6)-烷氧基、(C1-C6)-烷氧基羰基-(C1-C6)-烷氧基;
-(C3-C8)-环烷基,其环烷基为未取代的或被(C1-C6)-烷基和/或卤素单取代或多取代;(C3-C8)-环烷氧基、(C3-C8)-环烷基-(C1-C6)-烷基、(C3-C8)-环烷基-(C1-C6)-卤代烷基、(C3-C8)-环烷基-(C1-C6)-烷氧基、(C3-C8)-环烷基-(C1-C6)-卤代烷氧基、(C3-C8)-环烷基羰基、(C3-C8)-环烷氧基羰基、(C3-C8)-环烷基-(C1-C6)-烷基羰基、(C3-C8)-环烷基-(C1-C6)-卤代烷基羰基、(C3-C8)-环烷基-(C1-C6)-烷氧基羰基、(C3-C8)-环烷基-(C1-C6)-卤代烷氧基羰基、(C3-C8)-环烷基羰基氧基、(C3-C8)-环烷氧基羰基氧基、(C3-C8)-环烷基-(C1-C6)烷基羰基氧基、(C3-C8)-环烷基-(C1-C6)-卤代烷基羰基氧基、(C3-C8)-环烷基-(C1-C6)-烷氧基羰基氧基、(C3-C8)-环烷基-(C1-C6)-卤代烷氧基羰基氧基;
-(C3-C8)-环烯基、(C3-C8)-环烯基氧基、(C3-C8)-环烯基-(C1-C6)-烷基、(C3-C8)-环烯基-(C1-C6)-卤代烷基、(C3-C8)-环烯基-(C1-C6)-烷氧基、(C3-C8)-环烯基-(C1-C6)-卤代烷氧基、(C3-C8)-环烯基羰基、(C3-C8)-环烯基氧基羰基、(C3-C8)-环烯基-(C1-C6)-烷基羰基、(C3-C8)-环烯基-(C1-C6)-卤代烷基羰基、(C3-C8)-环烯基-(C1-C6)-烷氧基羰基、(C3-C8)-环烯基-(C1-C6)-卤代烷氧基羰基、(C3-C8)-环烯基羰基氧基、(C3-C8)-环烯基氧基羰基氧基、(C3-C8)-环烯基-(C1-C6)-烷基羰基氧基、(C3-C8)-环烯基-(C1-C6)-卤代烷基羰基氧基、(C3-C8)-环烯基-(C1-C6)-烷氧基羰基氧基、(C3-C8)-环烯基-(C1-C6)-卤代烷氧基羰基氧基;
-羟基-(C1-C6)-烷基、羟基-(C1-C6)-烷氧基、氰基-(C1-C6)-烷氧基、氰基-(C1-C6)-烷基;
-(C1-C6)-烷基磺酰基、(C1-C6)-烷硫基、(C1-C6)-烷基亚磺酰基、(C1-C6)-卤代烷基磺酰基、(C1-C6)-卤代烷硫基、(C1-C6)-卤代烷基亚磺酰基、(C1-C6)-烷基磺酰基-(C1-C6)-烷基、(C1-C6)-烷硫基-(C1-C6)-烷基、(C1-C6)-烷基亚磺酰基-(C1-C6)-烷基、(C1-C6)-卤代烷基磺酰基-(C1-C6)-烷基、(C1-C6)-卤代烷硫基-(C1-C6)-烷基、(C1-C6)-卤代烷基亚磺酰基-(C1-C6)-烷基、(C1-C6)-烷基磺酰基-(C1-C6)-卤代烷基、(C1-C6)-烷硫基-(C1-C6)-卤代烷基、(C1-C6)-烷基亚磺酰基-(C1-C6)-卤代烷基、(C1-C6)-卤代烷基磺酰基-(C1-C6)-卤代烷基、(C1-C6)-卤代烷硫基-(C1-C6)-卤代烷基、(C1-C6)-卤代烷基亚磺酰基-(C1-C6)-卤代烷基、(C1-C6)-烷基磺酰基氧基、(C1-C6)-卤代烷基磺酰基氧基、(C1-C6)-烷基硫代羰基、(C1-C6)-卤代烷基硫代羰基、(C1-C6)-烷基硫代羰基氧基、(C1-C6)-卤代烷基硫代羰基氧基、(C1-C6)-烷硫基-(C1-C6)-烷基、(C1-C6)-烷硫基-(C1-C6)-烷氧基、(C1-C6)-烷硫基-(C1-C6)-烷基羰基、(C1-C6)-烷硫基-(C1-C6)-烷基羰基氧基、(C4-C14)-芳基磺酰基、(C6-C14)-芳基硫基、(C6-C14)-芳基亚磺酰基、(C3-C8)-环烷硫基、(C3-C8)-烯基硫基、(C3-C8)-环烯基硫基和(C3-C6)-炔基硫基;
R3选自
-氢;
-(C1-C6)-烷基羰基、(C1-C6)-卤代烷基羰基;
-(C2-C6)-烯基羰基、(C1-C6)-卤代烯基羰基;
-(C2-C6)-炔基羰基、(C1-C6)-卤代炔基羰基;
-(C6-C14)-芳基羰基,其芳基部分在每种情况下可被卤素、(C1-C6)-烷基和/或(C1-C6)-卤代烷基取代;
-氨基羰基、[(C1-C6)-烷基氨基]羰基、[二-(C1-C6)-烷基氨基]羰基;
-(C1-C6)-烷氧基羰基、(C2-C6)-烯基氧基羰基、(C2-C6)-炔基氧基羰基;
-(C1-C6)-三烷基甲硅烷基;
-(C1-C6)-烷基磺酰基、(C1-C6)-卤代烷基磺酰基;
-(C6-C14)-芳基磺酰基,其芳基部分在每种情况下可被卤素、(C1-C6)-烷基和/或(C1-C6)-卤代烷基取代;
-(C1-C6)-烷基、(C1-C6)-卤代烷基、(C1-C6)-烷基羰基-(C1-C4)-烷基;
-(C2-C6)-烯基、(C2-C6)-卤代烯基;
-(C2-C6)-炔基、(C2-C6)-卤代炔基、三-(C1-C6)-烷基甲硅烷基-(C2-C6)-炔基、二-(C1-C6)-烷基甲硅烷基-(C2-C6)-炔基、单-(C1-C6)-烷基甲硅烷基-(C2-C6)-炔基、苯基甲硅烷基-(C2-C6)-炔基;
-(C1-C6)-烷氧基羰基-(C1-C6)-烷基、(C1-C6)-卤代烷氧基羰基-(C1-C6)-烷基、(C1-C6)-烷氧基羰基-(C1-C6)-卤代烷基、(C1-C6)-卤代烷氧基羰基-(C1-C6)-卤代烷基;
-(C6-C14)-芳基,其芳基部分在每种情况下可被卤素、(C1-C6)-烷基和/或(C1-C6)-卤代烷基取代;
-(C2-C14)杂芳基,其杂芳基部分在每种情况下可被卤素、(C1-C6)-烷基和/或(C1-C6)-卤代烷基取代;
-(C6-C14)-芳基-(C1-C6)-烷基,其芳基部分在每种情况下可被卤素、(C1-C6)-烷基和/或(C1-C6)-卤代烷基取代;
-氨基羰基-(C1-C6)-烷基;
-(C1-C6)-烷氧基-(C1-C6)-烷基;
-(C3-C8)-环烷基,其环烷基可被(C1-C6)-烷基和/或卤素单取代或多取代;
-(C3-C8)-环烷基-(C1-C6)-烷基、(C3-C8)-环烷基-(C1-C6)-卤代烷基;
-(C3-C8)-环烯基-(C1-C6)-烷基、(C3-C8)-环烯基-(C1-C6)-卤代烷基、羟基-(C1-C6)-烷基、氰基-(C1-C6)-烷基;
-(C1-C6)-烷基磺酰基-(C1-C6)-烷基、(C1-C6)-烷硫基-(C1-C6)-烷基、(C1-C6)-烷基亚磺酰基-(C1-C6)-烷基、(C1-C6)-卤代烷基磺酰基-(C1-C6)-烷基、(C1-C6)-卤代烷硫基-(C1-C6)-烷基、(C1-C6)-卤代烷基亚磺酰基-(C1-C6)-烷基、(C1-C6)-烷基磺酰基-(C1-C6)-卤代烷基、(C1-C6)-烷硫基-(C1-C6)-卤代烷基、(C1-C6)-烷基亚磺酰基-(C1-C6)-卤代烷基、(C1-C6)-卤代烷基磺酰基-(C1-C6)-卤代烷基、(C1-C6)-卤代烷硫基-(C1-C6)-卤代烷基、(C1-C6)-卤代烷基亚磺酰基-(C1-C6)-卤代烷基;
R4和R5各自彼此独立地选自氢、(C1-C6)-烷基、(C1-C6)-卤代烷基、羟基、(C1-C6)-烷氧基和(C1-C6)-卤代烷氧基;或者基团R4和R5与它们所连接的碳原子一起形成三至七元环;
R6和R7各自彼此独立地选自氢、(C1-C6)-烷基、(C1-C6)-卤代烷基、(C1-C6)-烷氧基、(C1-C6)-卤代烷氧基、(C6-C14)-芳基、(C6-C14)-芳基氧基、(C6-C14)-芳基羰基和(C6-C14)-芳基氧基羰基;或者
基团R6和R7一起形成可含有一个或多个氧和/或硫原子的(C1-C7)-亚烷基基团,其中(C1-C7)-亚烷基基团可被卤素单取代或多取代且各卤素取代基可相同或不同;
n代表顺序号0、1或2;
R8、R9、R10和R11各自彼此独立地选自氢、卤素、氰基、C(O)OH、C(O)NH2、(C1-C6)-烷基、(C1-C6)-烷基羰基、(C1-C6)-烷基氧基羰基、(C1-C6)-烷基氨基羰基、(C1-C6)-二烷基氨基羰基、(C1-C6)-卤代烷基、(C1-C6)-烷氧基、(C1-C6)-卤代烷氧基、(C2-C6)-烯基、(C2-C6)-炔基、(C2-C6)-卤代炔基、(C2-C6)-炔基羰基、(C2-C6)-卤代炔基羰基、(C2-C6)-炔基氧基、(C2-C6)-卤代炔基氧基、(C2-C6)-炔基氧基羰基、(C2-C6)-卤代炔基氧基羰基、(C6-C14)-芳基和硝基,其中R9和R10基团可通过-O-CH2-O-基团彼此连接而形成环;
X代表化学键、CH2、O、S、羰基、NH、CR12R13、NR14、CH2O或CH2S,其中最后提及的两个基团中的碳原子与芳族部分相连且杂原子O或S与部分氢化的胺部分相连;
R12和R13各自彼此独立地选自氢、(C1-C6)-烷基和(C1-C6)-卤代烷基;并且
R14选自氢、(C1-C6)-烷基和(C1-C6)-卤代烷基。
2.根据权利要求1所述的通式(I)的化合物,其特征在于,
R1a选自
-氢、氰基;
-(C1-C6)-烷基、(C1-C6)-卤代烷基、(C2-C6)-烯基、(C2-C6)-卤代烯基、(C2-C6)-炔基、(C2-C6)-卤代炔基;
-(C3-C8)-环烷基,其环烷基可未被取代或被(C1-C6)-烷基和/或卤素单取代或多取代;
并且
R1b选自
-氰基、C(O)OH、C(O)NH2;
-(C1-C6)-烷基、(C1-C6)-卤代烷基、(C1-C6)-烷基羰基-(C1-C4)-烷基;
-(C1-C6)-烷氧基羰基-(C1-C6)-烷基、(C2-C6)-烯基、(C2-C6)-卤代烯基;
-(C2-C6)-炔基、(C2-C6)-卤代炔基;
-(C6-C14)-芳基,其芳基部分在每种情况下可被卤素、(C1-C6)-烷基和/或(C1-C6)-卤代烷基取代;
-吡啶基,其在每种情况下可被卤素、(C1-C6)-烷基和/或(C1-C6)-卤代烷基取代;
-噻吩基,其在每种情况下可被卤素、(C1-C6)-烷基和/或(C1-C6)-卤代烷基取代;
-(C6-C14)-芳基-(C1-C6)-烷基,其芳基部分在每种情况下可被卤素、(C1-C6)-烷基和/或(C1-C6)-卤代烷基取代;
-(C3-C8)-环烷基,其环烷基可为未取代的或被(C1-C6)-烷基和/或卤素单取代或多取代;(C3-C8)-环烷基-(C1-C6)-烷基、(C3-C8)-环烷基-(C1-C6)-卤代烷基;
-(C3-C8)-环烯基、(C3-C8)-环烯基-(C1-C6)-烷基、(C3-C8)-环烯基-(C1-C6)-卤代烷基;
-氰基-(C1-C6)-烷基;
-(C1-C6)-烷基磺酰基-(C1-C6)-烷基、(C1-C6)-烷硫基-(C1-C6)-烷基、(C1-C6)-烷基亚磺酰基-(C1-C6)-烷基。
3.根据权利要求1所述的通式(I)的化合物,其特征在于,
R1a选自
-氢;
-(C1-C3)-烷基、(C1-C3)-卤代烷基、(C2-C3)-烯基、(C2-C3)-炔基;
并且
R1b选自
-氰基;
-(C1-C4)-烷基、(C1-C4)-卤代烷基;
-(C1-C3)-烷氧基羰基甲基、(C2-C4)-烯基、(C2-C4)-卤代烯基;
-(C2-C4)-炔基、(C2-C4)-卤代炔基;
-苯基,其芳基部分可被卤素和/或甲基取代;
-CH2-苯基(苄基),其芳基部分可被卤素和/或甲基取代;
-(C3-C6)-环烷基,其环烷基可为未取代的或被甲基和/或卤素单取代或多取代。
4.根据权利要求1至3中任一项所述的通式(I)的化合物,其特征在于,如果R1a不代表氢,则R1a通过化学键与R1b相连,使得它们与这两个基团所连接的碳一起形成饱和的3至6元碳环,该碳环为未取代的或被一个或多个选自甲基、三氟甲基、环丙基的取代基取代。
5.根据权利要求1至4中任一项所述的通式(I)的化合物,其特征在于,R2a和R2b各自彼此独立地选自氢、(C1-C6)-烷基、(C1-C6)-卤代烷基、(C1-C6)-烷氧基、(C1-C6)-烷氧基-(C1-C6)-烷基、(C3-C8)-环烷基、(C3-C8)-环烷基-(C1-C6)-烷基和(C3-C8)-环烷基-(C1-C6)-卤代烷基,其中环烷基在每种情况下为未取代的或被(C1-C6)-烷基和/或卤素取代。
6.根据权利要求1至5中任一项所述的通式(I)的化合物,其特征在于,R3选自氢、(C1-C4)-烷基羰基、苯基羰基(苯甲酰基)、(C1-C3)-烷基、CH2(C2-C3)-烯基、CH(CH3)(C2-C3)-烯基、CH2(C2-C3)-炔基、CH(CH3)(C2-C3)-炔基、(C1-C3)-烷氧基羰基甲基、CH2-苯基(苄基)、CH2(4-F-苯基)和Si(CH3)3。
7.根据权利要求1至5中任一项所述的通式(I)的化合物,其特征在于,R3选自氢、CH3、CH2CH3、CH2CH=CH2、CH2C(CH3)=CH2、CH2CH=CHCH3、CH2C≡CH、CH2C≡CCH3、CH(CH3)C=CH2、CH(CH3)C≡CH和CH2C(O)OCH3。
8.根据权利要求1至5中任一项所述的通式(I)的化合物,其特征在于,R4和R5各自彼此独立地选自氢、羟基、(C1-C6)-烷基、(C1-C6)-烷基苯基和(C1-C6)-烷氧基。
9.根据权利要求1至8中任一项所述的通式(I)的化合物,其特征在于,R6和R7彼此独立地选自氢、(C1-C6)-烷基和(C6-C14)-芳基。
10.根据权利要求1至9中任一项所述的通式(I)的化合物,其特征在于,R8选自氢、卤素、氰基、C(O)OH、(C1-C6)-烷基、(C1-C6)-烷氧基、(C1-C6)-烷氧基羰基和(C6-C14)-芳基。
11.根据权利要求1至10中任一项所述的通式(I)的化合物,其特征在于,R9选自氢、卤素、(C1-C6)-烷基和(C1-C6)-烷氧基。
12.根据权利要求1至11中任一项所述的通式(I)的化合物,其特征在于,R10选自氢、卤素、氰基、氨基羰基、羟基羰基、(C1-C6)-烷基、(C1-C6)-卤代烷基、(C1-C6)-烷氧基、(C2-C6)-烯基、(C2-C6)-炔基、(C1-C6)-烷基-(C2-C6)-炔基、羟基-(C1-C6)-烷基-(C2-C6)-炔基、(C1-C6)-烷氧基-(C2-C6)-炔基和芳基-(C2-C6)-炔基。
13.根据权利要求1至12中任一项所述的通式(I)的化合物,其特征在于,R11选自氢和(C1-C6)-烷基。
14.根据权利要求1至13中任一项所述的通式(I)的化合物,其特征在于,X选自化学键、CH2、O、S、羰基、NH、CH(C1-C6)-烷基、N(C1-C6)-烷基、OCH2和SCH2,其中在最后提及的两个基团中的碳原子与芳族部分相连,杂原子O或S与部分氢化的胺部分相连。
15.根据权利要求1至14中任一项所述的通式(I)的化合物,其特征在于,R9和R10通过-O-CH2-O-基团相连而形成环。
16.根据权利要求1至15中任一项所述的通式(I)的化合物,其特征在于,顺序号n为0或1。
17.根据权利要求1至16中任一项所述的通式(I)的化合物,
其特征在于,由(*)标记的手性碳原子具有(R)构型。
18.根据权利要求1至16中任一项所述的通式(I)的化合物,
其特征在于,由(*)标记的手性碳原子具有(R)构型且由(**)标记的手性碳原子具有(S)构型。
19.一种制备通式(I)的化合物和/或其农业化学上可接受的盐和/或其农业化学上可接受的季铵化氮衍生物的方法,
其中R1a至R11以及X和n如权利要求1至16中任一项所定义,将通式(II)的化合物
其中R1a、R1b、R2a、R2b和R3如权利要求1至16中任一项所定义且Z1代表选自以下的可交换基团或离去基团:氟、氯、溴、碘、(C1-C4)-烷基硫烷基、(C1-C4)-烷基亚磺酰基、(C1-C4)-烷基磺酰基、未取代的苯基-(C1-C4)-烷基磺酰基或被氟、氯、溴或(C1-C4)-烷基或(C1-C4)-烷氧基单取代或多取代的苯基-(C1-C4)-烷基磺酰基,或(C1-C4)-烷基苯基磺酰基;
与通式(III)的胺或通式(III)的胺的酸加成盐进行反应,
其中基团R4至R11以及X和n如权利要求1至16中任一项所定义。
20.一种制备通式(I)的化合物和/或其农业化学上可接受的盐和/或其农业化学上可接受的季铵化氮衍生物的方法,
其中基团R1至R11以及X和n如权利要求1至16中任一项所定义,
通过将通式(IIa)的化合物
其中R1b和R2a以及R2b如权利要求1至16中任一项所定义且Z1代表选自以下的可交换基团或离去基团:氟、氯、溴、碘、(C1-C4)-烷基硫烷基或(C1-C4)-烷基亚磺酰基或(C1-C4)-烷基磺酰基、未取代或取代的苯基-(C1-C4)-烷基磺酰基或(C1-C4)-烷基苯基磺酰基;
与通式(III)的胺或通式(III)的胺的酸加成盐进行反应,
其中基团R4至R11、X和n如权利要求1至17中任一项所定义,
并最后使酮基团还原或最后使酮基团与碳亲核试剂进行反应而得到R3代表氢的式(I)的化合物。
21.一种制备通式(I)的化合物和/或其农业化学上可接受的盐和/或其农业化学上可接受的季铵化氮衍生物的方法,
其中基团R1a至R11以及X和n如权利要求1至16中任一项所定义,
通过将通式(IIb)的化合物
其中R1和R2a以及R2b如权利要求1至17中任一项所定义且Z1代表可交换基团或离去基团,
与通式(III)的胺或通式(III)的胺的酸加成盐进行反应
其中基团R4至R11、X和n如权利要求1至16中任一项所定义,
而得到式(Ib)的2-氨基-5-酮嘧啶衍生物
其中基团R1a至R11以及X和n如权利要求1至16中任一项所定义,
并最后使酮基团与碳亲核试剂进行反应而得到R3代表氢的式(I)的化合物。
22.一种制备通式(I)的化合物——其中基团R1至R11以及X和n如权利要求1至16中任一项所定义——和/或其农业化学上可接受的盐和/或其农业化学上可接受的季铵化氮衍生物的方法,
其中基团R1a至R11以及X和n如权利要求1至17中任一项所定义,
通过将通式(IIc)的化合物
其中R2a和R2b如权利要求1至17中任一项所定义且Z1代表可交换基团或离去基团,
与式(III)的胺或或式(III)的胺的酸加成盐进行反应,
其中基团R4至R11、X和n如权利要求1至17中任一项所定义,
得到式(Ic)的中间体
其中基团R2a至R11以及X和n如权利要求1至17中任一项所定义,
并最后使酯基与碳亲核试剂进行反应而得到R1a=R1b且R3代表氢的式(I)的化合物。
23.根据权利要求19至21中任一项所述的制备通式(I)的化合物和/或其农业化学上可接受的盐和/或其农业化学上可接受的季铵化氮衍生物的方法,其特征在于,在R3代表氢的式(I)的化合物中,R3通过烷基化或酰基化类型的反应转化为R3不代表氢的式(I)的化合物,其中R3如权利要求1至17中任一项所定义。
24.除草组合物或调节植物生长的组合物,其特征在于,其包含一种或多种如权利要求1至17中任一项所述的通式(I)的化合物或其盐。
25.一种防治有害植物或调解植物生长的方法,其特征在于,将有效量的一种或多种如权利要求1至17中任一项所述的通式(I)的化合物或其盐施用于植物、植物部位、植物种子或栽培区域。
26.根据权利要求1至17中任一项所述的通式(I)的化合物或其盐作为除草剂或作为植物生长调节剂的用途。
27.根据权利要求25所述的用途,其特征在于,通式(I)的化合物或其盐在有用植物或观赏植物的作物中用于防治有害植物或调节植物生长。
28.根据权利要求25或26所述的用途,其特征在于,所述作物植物为转基因作物植物。
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- 2018-03-29 JP JP2019554735A patent/JP7107962B2/ja active Active
- 2018-03-29 US US16/494,485 patent/US11477982B2/en active Active
- 2018-03-29 WO PCT/EP2018/058081 patent/WO2018184978A1/de unknown
- 2018-03-29 EP EP18715613.8A patent/EP3606915A1/de not_active Withdrawn
- 2018-03-29 BR BR112019020877-1A patent/BR112019020877A2/pt not_active Application Discontinuation
- 2018-03-29 CN CN201880022605.7A patent/CN110461833A/zh active Pending
- 2018-04-05 UY UY0001037666A patent/UY37666A/es not_active Application Discontinuation
- 2018-04-05 AR ARP180100844A patent/AR111405A1/es unknown
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Also Published As
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AR111405A1 (es) | 2019-07-10 |
UY37666A (es) | 2018-10-31 |
US20200029565A1 (en) | 2020-01-30 |
BR112019020877A2 (pt) | 2020-05-12 |
US11477982B2 (en) | 2022-10-25 |
JP2020516600A (ja) | 2020-06-11 |
EP3606915A1 (de) | 2020-02-12 |
JP7107962B2 (ja) | 2022-07-27 |
WO2018184978A1 (de) | 2018-10-11 |
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