CN103221409B - 除草的苯并*嗪酮类 - Google Patents
除草的苯并*嗪酮类 Download PDFInfo
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- CN103221409B CN103221409B CN201180054676.3A CN201180054676A CN103221409B CN 103221409 B CN103221409 B CN 103221409B CN 201180054676 A CN201180054676 A CN 201180054676A CN 103221409 B CN103221409 B CN 103221409B
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- Prior art keywords
- benzo
- alkyl
- methyl
- formula
- zionoes
- Prior art date
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- 125000005605 benzo group Chemical group 0.000 title claims abstract description 125
- 238000009333 weeding Methods 0.000 title claims description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 55
- 239000001257 hydrogen Substances 0.000 claims abstract description 54
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 48
- 150000002367 halogens Chemical class 0.000 claims abstract description 48
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 37
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 32
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims abstract description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 19
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 14
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 13
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 11
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 10
- 239000000203 mixture Substances 0.000 claims description 254
- -1 sulphinyl Chemical group 0.000 claims description 224
- 150000001875 compounds Chemical class 0.000 claims description 108
- 150000003839 salts Chemical class 0.000 claims description 49
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 46
- 238000000034 method Methods 0.000 claims description 45
- 230000000694 effects Effects 0.000 claims description 35
- 230000002363 herbicidal effect Effects 0.000 claims description 31
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 29
- 125000003545 alkoxy group Chemical group 0.000 claims description 28
- 239000001301 oxygen Substances 0.000 claims description 21
- 229920006395 saturated elastomer Polymers 0.000 claims description 20
- 239000005864 Sulphur Substances 0.000 claims description 19
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 17
- 239000007787 solid Substances 0.000 claims description 16
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 12
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 9
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 7
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 5
- 230000008635 plant growth Effects 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 2
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- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 66
- 241000196324 Embryophyta Species 0.000 description 53
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 43
- 229910052731 fluorine Inorganic materials 0.000 description 43
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- 239000011737 fluorine Substances 0.000 description 38
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
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- 239000000460 chlorine Chemical group 0.000 description 33
- 239000011541 reaction mixture Substances 0.000 description 33
- 239000003112 inhibitor Substances 0.000 description 31
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
- 150000002148 esters Chemical class 0.000 description 30
- 229910052757 nitrogen Inorganic materials 0.000 description 30
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- 239000000047 product Substances 0.000 description 27
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 26
- 235000019439 ethyl acetate Nutrition 0.000 description 26
- 239000000725 suspension Substances 0.000 description 23
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 23
- 239000003513 alkali Substances 0.000 description 22
- 229910052801 chlorine Inorganic materials 0.000 description 22
- 108090000623 proteins and genes Proteins 0.000 description 21
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
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- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 18
- 244000299507 Gossypium hirsutum Species 0.000 description 17
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- 239000000463 material Substances 0.000 description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 16
- 239000000049 pigment Substances 0.000 description 16
- 102000004169 proteins and genes Human genes 0.000 description 16
- 238000005160 1H NMR spectroscopy Methods 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 235000001855 Portulaca oleracea Nutrition 0.000 description 15
- 241000219304 Portulacaceae Species 0.000 description 15
- 150000001412 amines Chemical class 0.000 description 15
- 229910052794 bromium Inorganic materials 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000012043 crude product Substances 0.000 description 15
- 229910052740 iodine Chemical group 0.000 description 15
- 229910001413 alkali metal ion Inorganic materials 0.000 description 14
- 238000001035 drying Methods 0.000 description 14
- VXPLXMJHHKHSOA-UHFFFAOYSA-N propham Chemical compound CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 description 14
- 239000011734 sodium Substances 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- 0 *C1(*)Oc(cc(*)c(*)c2)c2N(*)C1=* Chemical compound *C1(*)Oc(cc(*)c(*)c2)c2N(*)C1=* 0.000 description 13
- XFTWUNOVBCHBJR-UHFFFAOYSA-N Aspergillomarasmine A Chemical compound OC(=O)C(N)CNC(C(O)=O)CNC(C(O)=O)CC(O)=O XFTWUNOVBCHBJR-UHFFFAOYSA-N 0.000 description 13
- 240000006122 Chenopodium album Species 0.000 description 13
- 235000009344 Chenopodium album Nutrition 0.000 description 13
- 229920000742 Cotton Polymers 0.000 description 13
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 13
- 101000963974 Hydrophis stokesii Alpha-elapitoxin-Ast2b Proteins 0.000 description 13
- 101000964025 Naja naja Long neurotoxin 3 Proteins 0.000 description 13
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 13
- 235000002595 Solanum tuberosum Nutrition 0.000 description 13
- 244000061456 Solanum tuberosum Species 0.000 description 13
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 13
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 13
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 description 13
- 150000003851 azoles Chemical class 0.000 description 13
- 150000001721 carbon Chemical group 0.000 description 13
- 239000003795 chemical substances by application Substances 0.000 description 13
- 235000005822 corn Nutrition 0.000 description 13
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- 239000002904 solvent Substances 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
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- 150000003254 radicals Chemical class 0.000 description 12
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 11
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 11
- 240000006995 Abutilon theophrasti Species 0.000 description 10
- YQVMVCCFZCMYQB-UHFFFAOYSA-N Flamprop Chemical compound C=1C=C(F)C(Cl)=CC=1N(C(C)C(O)=O)C(=O)C1=CC=CC=C1 YQVMVCCFZCMYQB-UHFFFAOYSA-N 0.000 description 10
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 10
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 10
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- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
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- AKTQJCBOGPBERP-UHFFFAOYSA-N triflusulfuron Chemical compound FC(F)(F)COC1=NC(N(C)C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2C)C(O)=O)=N1 AKTQJCBOGPBERP-UHFFFAOYSA-N 0.000 description 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
- NRZWQKGABZFFKE-UHFFFAOYSA-N trimethylsulfonium Chemical compound C[S+](C)C NRZWQKGABZFFKE-UHFFFAOYSA-N 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
-
- 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
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Abstract
本发明提供了式I的苯并嗪酮类,其中R1为氢或卤素;R2为氢、C1-C6烷基、C1-C6卤代烷基、C3-C6环烷基、C3-C6链烯基、C3-C6卤代链烯基、C3-C6炔基、C3-C6卤代炔基、C1-C6烷氧基或C3-C6环烷基-C1-C6烷基;R3为卤素;R4为卤素;X为O或S;以及Y为取代或未取代的杂环;式I的苯并嗪酮类可以用作除草剂。
Description
本发明涉及如下所定义的通式I的苯并嗪酮类及其作为除草剂的用途。此外,本发明涉及用于作物保护的组合物以及一种防治不希望的植物生长的方法。
WO90/10626和WO97/07104例如尤其描述了具有除草作用的结构类似化合物,其与本发明的苯并嗪酮类I的不同在于苯并[1,4]嗪环优选在2位未被取代,而本发明式I的苯并嗪酮类在所述位置被至少一个卤原子取代。
然而,这些已知化合物对有害植物的除草性能并不总是完全令人满意。因此,本发明的目的是提供具有改进除草作用的苯并嗪酮类。尤其要提供具有高除草活性,尤其甚至在低施用率下,并且与商业利用的农作物充分相容的苯并嗪酮类。
这些和其他目的由如下所定义的式I的苯并嗪酮类及其可农用盐实现。
因此,本发明提供了式I的苯并嗪酮类:
其中
R1为氢或卤素;
R2为氢、C1-C6烷基、C1-C6卤代烷基、C3-C6环烷基、C3-C6链烯基、C3-C6卤代链烯基、C3-C6炔基、C3-C6卤代炔基、C1-C6烷氧基或C3-C6环烷基-C1-C6烷基;
R3为氢或卤素;
R4为卤素;
X为O或S;以及
Y选自Y1-Y66的取代基:
其中
A1-A10为氧或硫;
A11为氧、硫、SO或SO2;
A12-A17为氧或硫;
R5、R6、R7、R8、R23、R24、R29、R30、R37、R38、R39、R43、R44、R56和R58为氢、羟基、C1-C6烷基、C1-C6卤代烷基、C3-C7环烷基、C3-C7环烷氧基、C1-C6烷氧基、C1-C6卤代烷氧基、C2-C6链烯基、C2-C6卤代链烯基、C2-C6链烯氧基、C3-C6炔基、C3-C6炔氧基、C1-C6烷硫基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6烷氧基磺酰基、C1-C6烷基磺酰氧基、氨基、C1-C6烷基氨基或二(C1-C6烷基)氨基;或者
R5和R6、R7和R8、R23和R24或者R29和R30与它们所连接的原子一起形成饱和、部分不饱和或芳族3-6员环,该环除了碳原子外可以包含1-4个氮原子,或者1或2个氧原子,或者1或2个硫原子,或者1-3个氮原子和1个氧原子,或者1-3个氮原子和1个硫原子,或者1个硫和1个氧原子,并且其本身可以部分或完全被卤代和/或被1-3个选自C1-C6烷基和C1-C6烷氧基的基团取代;
R9、R10、R11、R12、R16、R17、R20、R21、R25、R26、R27、R28、R33、R34、R40、R45、R46、R50、R51、R53和R55为氢、氰基、羟基、C1-C6烷基、C1-C6氰基烷基、C1-C6卤代烷基、C3-C7环烷基、C3-C7环烷氧基、C1-C6烷氧基、C1-C6卤代烷氧基、C2-C6链烯基、C2-C6卤代链烯基、C2-C6链烯氧基、C3-C6炔基、C3-C6炔氧基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、苯基-C1-C6烷基、氨基、C1-C6烷基氨基或二(C1-C6烷基)氨基;或者
R11和R12、R16和R17、R25和R26、R27和R28或者R33和R34与它们所连接的原子一起形成饱和、部分不饱和或芳族3-6员环,该环除了碳原子外可以包含1-4个氮原子,或者1或2个氧原子,或者1或2个硫原子,或者1-3个氮原子和1个氧原子,或者1-3个氮原子和1个硫原子,或者1个硫和1个氧原子,并且其本身可以部分或完全被卤代和/或被1-3个选自C1-C6烷基和C1-C6烷氧基的基团取代;
R13为氢、C1-C6烷基、C1-C6卤代烷基、C2-C6链烯基、C3-C6炔基、C1-C6卤代烷氧基、氨基、C1-C6烷基氨基或二(C1-C6烷基)氨基;
R14、R15、R18、R22、R31和R32为氢、卤素或C1-C6烷基;
R19、R35、R36、R41、R42、R49、R52、R54和R57为氢、卤素、羟基、C1-C6烷基、C1-C6卤代烷基、C3-C7环烷基、C3-C7环烷氧基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6卤代烷硫基、C2-C6链烯基、C2-C6卤代链烯基、C2-C6链烯氧基、C3-C6炔基或C3-C6炔氧基;以及
R47为氢、NH2、C1-C6烷基或C3-C6炔基;
R59为氢、氨基、硝基、氰基、羧基、氨基甲酰基、硫代氨基甲酰基、卤素、C1-C6烷基、C1-C6卤代烷基、C3-C7环烷基、C3-C7环烷氧基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6卤代烷硫基、C2-C6链烯基、C2-C6卤代链烯基、C2-C6链烯氧基、C3-C6炔基、C3-C6炔氧基、C1-C6烷氧羰基、C2-C6链烯硫基、C3-C6炔硫基、C1-C6烷基氨基、二(C1-C6烷基)氨基或C3-C7环烷基-C1-C3烷基;
R60为氢、羟基、氨基、氰基、C1-C6烷基、C1-C6卤代烷基、C3-C7环烷基、C3-C7环烷氧基、C1-C6烷氧基、C1-C6卤代烷氧基、C2-C6链烯基、C3-C6炔基、C1-C6烷氧羰基、C1-C6烷基氨基、二(C1-C6烷基)氨基,C3-C7环烷基-C1-C3烷基、苯基或苯基-C1-C6烷基;
其中当Y为Y2或Y20时,R3和R4均为卤素;
包括其可农用盐。
本发明还提供了包含至少一种式I的苯并嗪酮类和至少一种选自除草活性化合物B和安全剂C的其他化合物的除草活性组合物。
本发明还提供了通式I的苯并嗪酮类作为除草剂的用途,即防治有害植物的用途。
本发明还提供了包含至少一种式I的苯并嗪酮类和常用于配制作物保护剂的助剂的混合物。
此外,本发明提供了一种防治不希望的植物生长的方法,其中使除草有效量的至少一种式I的苯并嗪酮类作用于植物、其种子和/或其生长地。施用可以在不希望的植物出苗之前、之中和/或之后进行。
此外,本发明涉及制备式I的苯并嗪酮类的方法和中间体。
本发明的其他实施方案由权利要求书、说明书和实施例明了。应理解的是本发明主题的上述特征和下文仍要说明的那些不仅可以在各种特定情形下所给组合使用,而且可以在不背离本发明范围下以其他组合使用。
本文所用术语“防治”和“防除”是同义词。
本文所用术语“不希望的植物生长”和“有害植物”是同义词。
若本文所述式I的苯并嗪酮类能够形成几何异构体,例如E/Z异构体,则可以在本发明组合物中使用纯异构体及其混合物二者。
若本文所述式I的苯并嗪酮类具有一个或多个手性中心且因此以对映体或非对映体存在,则可以在本发明组合物中使用纯对映体和非对映体及其混合物二者。
若本文所述式I的苯并嗪酮类具有可以被离子化的官能基团,则它们还可以以其可农用盐或其混合物形式使用。
合适的通常是其阳离子对活性化合物的作用没有不利影响(“可农用”)的那些阳离子的盐。优选的阳离子是碱金属的离子,优选锂、钠和钾离子,碱土金属的离子,优选钙和镁离子,以及过渡金属的离子,优选锰、铜、锌和铁离子,此外还有铵和其中1-4个氢原子被C1-C4烷基、羟基-C1-C4烷基、C1-C4烷氧基-C1-C4烷基、羟基-C1-C4烷氧基-C1-C4烷基、苯基或苄基替代的取代铵(下文也称为有机铵),优选铵、甲基铵、异丙基铵、二甲基铵、二异丙基铵、三甲基铵、四甲基铵、四乙基铵、四丁基铵、2-羟基乙基铵、2-(2-羟基乙氧基)乙-1-基铵、二(2-羟基乙-1-基)铵、苄基三甲基铵、苄基三乙基铵,此外还有离子,锍离子,优选三(C1-C4烷基)锍,如三甲基锍,以及氧化锍离子,优选三(C1-C4烷基)氧化锍。
有用酸加成盐的阴离子主要是氯离子、溴离子、氟离子、碘离子、硫酸氢根、甲基硫酸根、硫酸根、磷酸二氢根、磷酸氢根、硝酸根、碳酸氢根、碳酸根、六氟硅酸根、六氟磷酸根、苯甲酸根以及C1-C4链烷酸的阴离子,优选甲酸根、乙酸根、丙酸根和丁酸根。
在本文所述变量的定义中,尤其就R1-R46所提到的有机结构部分象术语卤素一样为各基团成员的单独列举的集合性术语。术语卤素在每种情况下表示氟、氯、溴或碘。所有烃链,即所有烷基,可以是直链或支化的,前缀Cn-Cm在每种情况下表示该基团中的可能碳原子数目。
该类含义的实例为:
-C1-C4烷基:例如CH3、C2H5、正丙基和CH(CH3)2、正丁基、CH(CH3)-C2H5、CH2-CH(CH3)2和C(CH3)3;
-C1-C6烷基以及还有C1-C6氰基烷基、C1-C6环烷基-C1-C6烷基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6烷基磺酰氧基和苯基-C1-C6烷基的C1-C6烷基结构部分:如上所述的C1-C4烷基以及还有例如正戊基、1-甲基丁基、2-甲基丁基、3-甲基丁基、2,2-二甲基丙基、1-乙基丙基、正己基、1,1-二甲基丙基、1,2-二甲基丙基、1-甲基戊基、2-甲基戊基、3-甲基戊基、4-甲基戊基、1,1-二甲基丁基、1,2-二甲基丁基、1,3-二甲基丁基、2,2-二甲基丁基、2,3-二甲基丁基、3,3-二甲基丁基、1-乙基丁基、2-乙基丁基、1,1,2-三甲基丙基、1,2,2-三甲基丙基、1-乙基-1-甲基丙基或1-乙基-2-甲基丙基,优选甲基、乙基、正丙基、1-甲基乙基、正丁基、1,1-二甲基乙基、正戊基或正己基;
-C1-C4卤代烷基:部分或完全被氟、氯、溴和/或碘取代的如上所述的C1-C4烷基,例如氯甲基、二氯甲基、三氯甲基、氟甲基、二氟甲基、三氟甲基、氯氟甲基、二氯一氟甲基、一氯二氟甲基、溴甲基、碘甲基、2-氟乙基、2-氯乙基、2-溴乙基、2-碘乙基、2,2-二氟乙基、2,2,2-三氟乙基、2-氯-2-氟乙基、2-氯-2,2-二氟乙基、2,2-二氯-2-氟乙基、2,2,2-三氯乙基、五氟乙基、2-氟丙基、3-氟丙基、2,2-二氟丙基、2,3-二氟丙基、2-氯丙基、3-氯丙基、2,3-二氯丙基、2-溴丙基、3-溴丙基、3,3,3-三氟丙基、3,3,3-三氯丙基、2,2,3,3,3-五氟丙基、七氟丙基、1-氟甲基-2-氟乙基、1-氯甲基-2-氯乙基、1-溴甲基-2-溴乙基、4-氟丁基、4-氯丁基、4-溴丁基、九氟丁基、1,1,2,2,-四氟乙基和1-三氟甲基-1,2,2,2-四氟乙基;
-C1-C6卤代烷基以及还有C1-C6卤代烷硫基的C1-C6卤代烷基结构部分:如上所述的C1-C4卤代烷基以及例如还有5-氟戊基、5-氯戊基、5-溴戊基、5-碘戊基、十一氟戊基、6-氟己基、6-氯己基、6-溴己基、6-碘己基和十三氟己基;
-C3-C6环烷基以及还有C3-C6环烷基-C1-C6烷基的环烷基结构部分:具有3-6个环成员的单环饱和烃,如环丙基、环丁基、环戊基和环己基;
-C3-C7环烷基以及还有C3-C7环烷氧基的环烷基结构部分:具有3-7个环成员的单环饱和烃,如环丙基、环丁基、环戊基、环己基和环庚基;
-C3-C6链烯基:例如1-丙烯基、2-丙烯基、1-甲基乙烯基、1-丁烯基、2-丁烯基、3-丁烯基、1-甲基-1-丙烯基、2-甲基-1-丙烯基、1-甲基-2-丙烯基、2-甲基-2-丙烯基、1-戊烯基、2-戊烯基、3-戊烯基、4-戊烯基、1-甲基-1-丁烯基、2-甲基-1-丁烯基、3-甲基-1-丁烯基、1-甲基-2-丁烯基、2-甲基-2-丁烯基、3-甲基-2-丁烯基、1-甲基-3-丁烯基、2-甲基-3-丁烯基、3-甲基-3-丁烯基、1,1-二甲基-2-丙烯基、1,2-二甲基-1-丙烯基、1,2-二甲基-2-丙烯基、1-乙基-1-丙烯基、1-乙基-2-丙烯基、1-己烯基、2-己烯基、3-己烯基、4-己烯基、5-己烯基、1-甲基-1-戊烯基、2-甲基-1-戊烯基、3-甲基-1-戊烯基、4-甲基-1-戊烯基、1-甲基-2-戊烯基、2-甲基-2-戊烯基、3-甲基-2-戊烯基、4-甲基-2-戊烯基、1-甲基-3-戊烯基、2-甲基-3-戊烯基、3-甲基-3-戊烯基、4-甲基-3-戊烯基、1-甲基-4-戊烯基、2-甲基-4-戊烯基、3-甲基-4-戊烯基、4-甲基-4-戊烯基、1,1-二甲基-2-丁烯基、1,1-二甲基-3-丁烯基、1,2-二甲基-1-丁烯基、1,2-二甲基-2-丁烯基、1,2-二甲基-3-丁烯基、1,3-二甲基-1-丁烯基、1,3-二甲基-2-丁烯基、1,3-二甲基-3-丁烯基、2,2-二甲基-3-丁烯基、2,3-二甲基-1-丁烯基、2,3-二甲基-2-丁烯基、2,3-二甲基-3-丁烯基、3,3-二甲基-1-丁烯基、3,3-二甲基-2-丁烯基、1-乙基-1-丁烯基、1-乙基-2-丁烯基、1-乙基-3-丁烯基、2-乙基-1-丁烯基、2-乙基-2-丁烯基、2-乙基-3-丁烯基、1,1,2-三甲基-2-丙烯基、1-乙基-1-甲基-2-丙烯基、1-乙基-2-甲基-1-丙烯基和1-乙基-2-甲基-2-丙烯基;
-C2-C6链烯基和C2-C6链烯氧基的链烯基结构部分:如上所述的C3-C6链烯基以及还有乙烯基;
-C2-C6卤代链烯基:部分或全部被氟、氯、溴和/或碘取代的如上所述的C2-C6链烯基,例如2-氯丙-2-烯-1-基、3-氯丙-2-烯-1-基、2,3-二氯丙-2-烯-1-基、3,3-二氯丙-2-烯-1-基、2,3,3-三氯-2-烯-1-基、2,3-二氯丁-2-烯-1-基、2-溴丙-2-烯-1-基、3-溴丙-2-烯-1-基、2,3-二溴丙-2-烯-1-基、3,3-二溴丙-2-烯-1-基、2,3,3-三溴-2-烯-1-基或2,3-二溴丁-2-烯-1-基;
-C3-C6炔基以及还有C3-C6炔氧基的C3-C6炔基结构部分:例如1-丙炔基、2-丙炔基、1-丁炔基、2-丁炔基、3-丁炔基、1-甲基-2-丙炔基、1-戊炔基、2-戊炔基、3-戊炔基、4-戊炔基、1-甲基-2-丁炔基、1-甲基-3-丁炔基、2-甲基-3-丁炔基、3-甲基-1-丁炔基、1,1-二甲基-2-丙炔基、1-乙基-2-丙炔基、1-己炔基、2-己炔基、3-己炔基、4-己炔基、5-己炔基、1-甲基-2-戊炔基、1-甲基-3-戊炔基、1-甲基-4-戊炔基、2-甲基-3-戊炔基、2-甲基-4-戊炔基、3-甲基-1-戊炔基、3-甲基-4-戊炔基、4-甲基-1-戊炔基、4-甲基-2-戊炔基、1,1-二甲基-2-丁炔基、1,1-二甲基-3-丁炔基、1,2-二甲基-3-丁炔基、2,2-二甲基-3-丁炔基、3,3-二甲基-1-丁炔基、1-乙基-2-丁炔基、1-乙基-3-丁炔基、2-乙基-3-丁炔基和1-乙基-1-甲基-2-丙炔基;
-C3-C6卤代炔基:部分或全部被氟、氯、溴和/或碘取代的如上所述的C3-C6炔基,例如1,1-二氟丙-2-炔-1-基、3-氯丙-2-炔-1-基、3-溴丙-2-炔-1-基、3-碘丙-2-炔-1-基、4-氟丁-2-炔-1-基、4-氯丁-2-炔-1-基、1,1-二氟丁-2-炔-1-基、4-碘丁-3-炔-1-基、5-氟戊-3-炔-1-基、5-碘戊-4-炔-1-基、6-氟己-4-炔-1-基或6-碘己-5-炔-1-基;
-C1-C4烷氧基:例如甲氧基、乙氧基、丙氧基、1-甲基乙氧基、丁氧基、1-甲基丙氧基、2-甲基丙氧基和1,1-二甲基乙氧基;
-C1-C6烷氧基以及还有C1-C6卤代烷氧基、C1-C6烷氧基磺酰基的C1-C6烷氧基结构部分:如上所述的C1-C4烷氧基以及还有例如戊氧基、1-甲基丁氧基、2-甲基丁氧基、3-甲氧基丁氧基、1,1-二甲基丙氧基、1,2-二甲基丙氧基、2,2-二甲基丙氧基、1-乙基丙氧基、己氧基、1-甲基戊氧基、2-甲基戊氧基、3-甲基戊氧基、4-甲基戊氧基、1,1-二甲基丁氧基、1,2-二甲基丁氧基、1,3-二甲基丁氧基、2,2-二甲基丁氧基、2,3-二甲基丁氧基、3,3-二甲基丁氧基、1-乙基丁氧基、2-乙基丁氧基、1,1,2-三甲基丙氧基、1,2,2-三甲基丙氧基、1-乙基-1-甲基丙氧基和1-乙基-2-甲基丙氧基;
-C1-C4烷硫基:例如甲硫基、乙硫基、丙硫基、1-甲基乙硫基、丁硫基、1-甲基丙硫基、2-甲基丙硫基和1,1-二甲基乙硫基;
-C1-C6烷硫基:如上所述的C1-C4烷硫基以及还有例如戊硫基、1-甲基丁硫基、2-甲基丁硫基、3-甲基丁硫基、2,2-二甲基丙硫基、1-乙基丙硫基、己硫基、1,1-二甲基丙硫基、1,2-二甲基丙硫基、1-甲基戊硫基、2-甲基戊硫基、3-甲基戊硫基、4-甲基戊硫基、1,1-二甲基丁硫基、1,2-二甲基丁硫基、1,3-二甲基丁硫基、2,2-二甲基丁硫基、2,3-二甲基丁硫基、3,3-二甲基丁硫基、1-乙基丁硫基、2-乙基丁硫基、1,1,2-三甲基丙硫基、1,2,2-三甲基丙硫基、1-乙基-1-甲基丙硫基和1-乙基-2-甲基丙硫基;
-C1-C6烷基氨基:例如甲基氨基、乙基氨基、丙基氨基、1-甲基乙基氨基、丁基氨基、1-甲基丙基氨基、2-甲基丙基氨基、1,1-二甲基乙基氨基、戊基氨基、1-甲基丁基氨基、2-甲基丁基氨基、3-甲基丁基氨基、2,2-二甲基丙基氨基、1-乙基丙基氨基、己基氨基、1,1-二甲基丙基氨基、1,2-二甲基丙基氨基、1-甲基戊基氨基、2-甲基戊基氨基、3-甲基戊基氨基、4-甲基戊基氨基、1,1-二甲基丁基氨基、1,2-二甲基丁基氨基、1,3-二甲基丁基氨基、2,2-二甲基丁基氨基、2,3-二甲基丁基氨基、3,3-二甲基丁基氨基、1-乙基丁基氨基、2-乙基丁基氨基、1,1,2-三甲基丙基氨基、1,2,2-三甲基丙基氨基、1-乙基-1-甲基丙基氨基或1-乙基-2-甲基丙基氨基;
-二(C1-C4烷基)氨基:例如N,N-二甲基氨基、N,N-二乙基氨基、N,N-二丙基氨基、N,N-二(1-甲基乙基)氨基、N,N-二丁基氨基、N,N-二(1-甲基丙基)氨基、N,N-二(2-甲基丙基)氨基、N,N-二(1,1-二甲基乙基)氨基、N-乙基-N-甲基氨基、N-甲基-N-丙基氨基、N-甲基-N-(1-甲基乙基)氨基、N-丁基-N-甲基氨基、N-甲基-N-(1-甲基丙基)氨基、N-甲基-N-(2-甲基丙基)氨基、N-(1,1-二甲基乙基)-N-甲基氨基、N-乙基-N-丙基氨基、N-乙基-N-(1-甲基乙基)氨基、N-丁基-N-乙基氨基、N-乙基-N-(1-甲基丙基)氨基、N-乙基-N-(2-甲基丙基)氨基、N-乙基-N-(1,1-二甲基乙基)氨基、N-(1-甲基乙基)-N-丙基氨基、N-丁基-N-丙基氨基、N-(1-甲基丙基)-N-丙基氨基、N-(2-甲基丙基)-N-丙基氨基、N-(1,1-二甲基乙基)-N-丙基氨基、N-丁基-N-(1-甲基乙基)氨基、N-(1-甲基乙基)-N-(1-甲基丙基)氨基、N-(1-甲基乙基)-N-(2-甲基丙基)氨基、N-(1,1-二甲基乙基)-N-(1-甲基乙基)氨基、N-丁基-N-(1-甲基丙基)氨基、N-丁基-N-(2-甲基丙基)氨基、N-丁基-N-(1,1-二甲基乙基)氨基、N-(1-甲基丙基)-N-(2-甲基丙基)氨基、N-(1,1-二甲基乙基)-N-(1-甲基丙基)氨基和N-(1,1-二甲基乙基)-N-(2-甲基丙基)氨基;
-二(C1-C6烷基)氨基:如上所述的二(C1-C4烷基)氨基以及还有例如N,N-二戊基氨基、N,N-二己基氨基、N-甲基-N-戊基氨基、N-乙基-N-戊基氨基、N-甲基-N-己基氨基和N-乙基-N-己基氨基;
-饱和、部分不饱和或芳族3-6员环,该环除了碳原子外可以包含1-4个氮原子,或者1或2个氧原子,或者1或2个硫原子,或者1-3个氮原子和1个氧原子,或者1-3个氮原子和1个硫原子,或者1个硫和1个氧原子,例如
环丙基、环丁基、环戊基、环己基;
1-环丙烯基、2-环丙烯基、1-环丁烯基、2-环丁烯基、1-环戊烯基、2-环戊烯基、1,3-环戊二烯基、1,4-环戊二烯基、2,4-环戊二烯基、1-环己烯基、2-环己烯基、3-环己烯基、1,3-环己二烯基、1,4-环己二烯基、2,5-环己二烯基;苯基;
环氧乙烷基、氧杂环丁烷、氮丙啶基、硫杂丙环基、硫杂环丁烷基(thiethanyl)、氮杂环丁烷基、氮杂环丁烯基;
四氢呋喃基、四氢噻吩基、吡咯烷基、异唑烷基、异噻唑烷基、吡唑烷基、唑烷基、噻唑烷基、咪唑烷基、三唑烷基、二唑烷基、噻二唑烷基;
二氢呋喃基、二氧戊环基、二氢噻吩基、二氢吡咯基、二氢异唑基、二氢异噻唑基、二氢吡唑基、二氢咪唑基、二氢唑基、二氢噻唑基;呋喃基、噻吩基、吡咯基、吡唑基、异唑基、异噻唑基、咪唑基、唑基、噻唑基、二唑基、噻二唑基、三唑基、四唑基;
哌啶基、二烷基、二噻烷基、二噻烷基、氧硫杂环己烷基、四氢吡喃基、四氢噻喃基、六氢哒嗪基、六氢嘧啶基、哌嗪基、六氢三嗪基、四氢嗪基、吗啉基;
吡喃基、噻喃基、二氢嗪基、二氢吡喃基、二氢噻喃基、四氢吡啶基、二氢吡啶基、二氢噻嗪基、四氢哒嗪基、四氢嘧啶基、四氢吡嗪基、嗪基、噻嗪基、二氢哒嗪基、二氢吡嗪基、二氢嘧啶基;吡啶基、哒嗪基、嘧啶基、吡嗪基、三嗪基、四嗪基。
在下文中提到的本发明优选实施方案必须相互独立地或者相互组合地理解为优选的。
根据本发明的优选实施方案,还优选如下那些式I的苯并嗪酮类,其中各变量相互独立地或者相互组合地具有下列含义:
R1为氢;
还优选为卤素,
特别优选F或Cl,
尤其优选F;
R2为C3-C6炔基或C3-C6卤代炔基,
优选C3炔基或C3卤代炔基,
特别优选CH2C≡CH、CH2C≡CCl或CH2C≡CBr;
还优选为C3-C6炔基或C3-C6环烷基-C1-C6烷基,
特别优选炔丙基或环丙基甲基;
还优选为C3-C6炔基,优选C3炔基;特别优选CH2C≡CH;
还优选为C3-C6卤代炔基,优选C3卤代炔基,
特别优选CH2C≡CCl或CH2C≡CBr;
R3为氢;
还优选为卤素;特别优选F或Cl;更优选Cl;
还优选为卤素,特别优选F;
还优选为氢或F;
R4为氢;
还优选为卤素;特别优选F或Cl;更优选Cl;
还优选为卤素,特别优选F;
还优选为氢或F;
X为O,
还优选为S;
Y优选为Y2、Y13、Y12、Y20、Y31、Y37、Y38、Y39、Y42、Y55或Y66;
更优选为Y12、Y13、Y20、Y31、Y37、Y38、Y39、Y55或Y66;
仍更优选为Y2、Y42、Y55;
最优选为Y55;
A1-A10优选为氧;
还优选为硫;
A11优选为氧或硫,
更优选为氧;
还更优选为硫;
还优选为氧、SO或SO2;
还优选为硫、SO或SO2;
还更优选为SO或SO2;
A12-A17优选为氧;
还优选为硫;
R5、R6、R7、R8、R23、R24、R29、R30、R37、R38、R39、R43、R44、R56和R58优选为C1-C6烷基、C1-C6卤代烷基、C1-C6烷硫基、C1-C6烷基磺酰基,或者R5和R6、R7和R8、R23和R24或R29和R30与它们所连接的原子一起形成5或6员环,该环是饱和、部分不饱和或芳族的,除了碳原子外可以包含1-4个氮原子,或者1个氧原子,或者1个硫原子并且其本身可以部分或完全被卤代和/或被1-3个C1-C6烷基取代;
更优选为C1-C6烷基、C1-C6卤代烷基,或者R5和R6、R7和R8、R23和R24或R29和R30与它们所连接的原子一起形成5或6员环,该环是饱和、部分不饱和或芳族的并且其本身可以被1或2个卤原子,优选氟取代和/或被1-3个C1-C4烷基,优选甲基取代;
特别优选为C1-C6烷基或C1-C6卤代烷基;
还特别优选R5和R6、R7和R8、R23和R24或R29和R30与它们所连接的原子一起形成5或6员环,该环是饱和、部分不饱和或芳族的并且其本身可以被1或2个卤原子,优选氟取代和/或被1-3个C1-C4烷基,优选甲基取代;
R38和R43最优选为C1-C6卤代烷基;
R44最优选为CH3;
R9、R10、R11、R12、R16、R17、R20、R21、R25、R26、R27、R28、R33、R34、R40、R45、R46、R50、R51、R53和R55优选为氢、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基,或者R11和R12、R16和R17、R25和R26、R27和R28或R33和R34与它们所连接的原子一起形成5或6员环,该环是饱和、部分不饱和或芳族的,除了碳原子外可以包含1-4个氮原子,或者1或2个氧原子,或者1或2个硫原子并且其本身可以部分或完全被卤代;
更优选为氢、C1-C6烷基、C1-C6卤代烷基、C1-C6烷基磺酰基,或者R11和R12、R16和R17、R25和R26、R27和R28或R33和R34与它们所连接的原子一起形成5或6员环,该环是饱和、部分不饱和或芳族的并且其本身可以被1或2个卤原子,优选氟取代和/或被1-3个C1-C4烷基,优选甲基取代;
特别优选为氢、C1-C6烷基、C1-C6卤代烷基或C1-C6烷基磺酰基;
R20最优选为CF3、OCHF2;
R21最优选为Cl、Br、CH3;还特别优选R11和R12、R16和R17、R25和R26、R27和R28或R33和R34与它们所连接的原子一起形成5或6员环,该环是饱和、部分不饱和或芳族的并且其本身可以被1或2个卤原子,优选氟取代和/或被1-3个C1-C4烷基,优选甲基取代;
R13优选为C1-C6烷基或C1-C6卤代烷基;
R14、R15、R18、R22、R31和R32优选为氢、卤素或C1-C6烷基;更优选卤素或C1-C6烷基;最优选卤素;还最优选C1-C6烷基;还最优选氢;
R19、R35、R36、R41、R42、R49、R52、R54和R57优选为氢、卤素或C1-C6烷基;更优选卤素或C1-C6烷基;最优选卤素;还最优选C1-C6烷基;还最优选氢;
R36最优选为F、Cl;
R47优选为C1-C6烷基;
R59优选为氢、卤素、C1-C6烷基或C1-C6卤代烷基;更优选C1-C6烷基;
R60优选为氢、氨基、C1-C6烷基或C1-C6卤代烷基;更优选C1-C6烷基。
特别优选如下式I的苯并嗪酮类,其中X为O且Y为Y55,其中A15为O,R42为H,R43为CF3,R44为CH3,并且其在下文也被称为式Ia的苯并嗪酮类:
其中变量R1、R2、R3和R4具有如上所定义的含义,尤其是优选含义。
特别优选表A的式Ia1-Ia60的苯并嗪酮类,其中变量R1、R2、R3和R4的定义不仅相互组合而且在每种情况下也独立地对本发明化合物特别重要:
表A
还优选式Ib的苯并嗪酮类,特别优选式Ib1-Ib60的苯并嗪酮类,其与式Ia1-Ia60的对应苯并嗪酮类的不同仅在于Y为Y13,其中A1和A7为O,R10为CH3且R11和R12一起形成-(CH2-CHF-CH2)-,优选R11和R12一起形成(6S,7aR)立体异构体:
还优选式Ic的苯并嗪酮类,特别优选式Ic1-Ic60的苯并嗪酮类,其与式Ia1-Ia60的对应苯并嗪酮类的不同仅在于Y为Y20,其中A1为O且R25和R26一起形成-(CH2)4-:
还优选式Id的苯并嗪酮类,特别优选式Id1-Id60的苯并嗪酮类,其与式Ia1-Ia60的对应苯并嗪酮类的不同仅在于Y为Y20,其中A1为O,R25为CHF2且R26为CH3:
还优选式Ie的苯并嗪酮类,特别优选式Ie1-Ie60的苯并嗪酮类,其与式Ia1-Ia60的对应苯并嗪酮类的不同仅在于Y为Y31,其中A1和A7为O且R14和R15为CH3:
还优选式If的苯并嗪酮类,特别优选式If1-If60的苯并嗪酮类,其与式Ia1-Ia60的对应苯并嗪酮类的不同仅在于Y为Y37,其中A1为O,A11为S且R33和R34一起形成-(CH2)4-:
还优选式Ig的苯并嗪酮类,特别优选式Ig1-Ig60的苯并嗪酮类,其与式Ia1-Ia60的对应苯并嗪酮类的不同仅在于Y为Y38,其中A1为O且R35为C(CH3)3:
还优选式Ih的苯并嗪酮类,特别优选式Ih1-Ih60的苯并嗪酮类,其与式Ia1-Ia60的对应苯并嗪酮类的不同仅在于Y为Y39,其中A12为S且R11和R12一起形成-CH2-C(CH3)2-CH2-:
还优选式Ii的苯并嗪酮类,特别优选式Ii1-Ii60的苯并嗪酮类,其与式Ia1-Ia60的对应苯并嗪酮类的不同仅在于Y为Y12,其中A4、A5和A6为O且R9为-CH2-CH2-CH3:
还优选式Ik的苯并嗪酮类,特别优选式Ik1-Ik60的苯并嗪酮类,其与式Ia1-Ia60的对应苯并嗪酮类的不同仅在于Y为Y66,其中R47为CH3且R48为H:
还优选式Im的苯并嗪酮类,特别优选式Im1-Im60的苯并嗪酮类,其与式Ia1-Ia60的对应苯并嗪酮类的不同仅在于Y为Y2,其中R19为Cl,R20为CF3且R21为CH3:
还优选式In的苯并嗪酮类,特别优选式In1-In60的苯并嗪酮类,其与式Ia1-Ia60的对应苯并嗪酮类的不同仅在于Y为Y2,其中R19为Br,R20为CF3且R21为CH3:
还优选式Io的苯并嗪酮类,特别优选式Io1-Io60的苯并嗪酮类,其与式Ia1-Ia60的对应苯并嗪酮类的不同仅在于Y为Y2,其中R19为Cl,R20为OCHF2且R21为CH3:
还优选式Ip的苯并嗪酮类,特别优选式Ip1-Ip60的苯并嗪酮类,其与式Ia1-Ia60的对应苯并嗪酮类的不同仅在于Y为Y2,其中R19为Br,R20为OCHF2且R21为CH3:
还优选式Iq的苯并嗪酮类,特别优选式Iq1-Iq60的苯并嗪酮类,其与式Ia1-Ia60的对应苯并嗪酮类的不同仅在于Y为Y42,其中R36为F,R37为H,R38为CF3且R39为H:
还优选式Ir的苯并嗪酮类,特别优选式Ir1-Ir60的苯并嗪酮类,其与式Ia1-Ia60的对应苯并嗪酮类的不同仅在于Y为Y13,其中A1和A7为O,R10为氢且R11和R12一起形成-(CH2-CHF-CH2)-,优选R11和R12一起形成(6S,7aR)立体异构体:
本发明式I的苯并嗪酮类可以通过有机化学的标准方法制备,例如经由如下所示的硝基化合物III和胺II制备:
优选氨基化合物IIa(=氨基化合物II,其中R4为氟且X为O):
硝基化合物III的还原通常在20℃至反应混合物的沸点,优选20-200℃,特别优选20-100℃下在惰性有机溶剂中进行(Organikum,Heidelberg,1993,第320-323页)。
合适的还原剂是初生H2;在催化量的过渡金属或过渡金属化合物,尤其是第8过渡族的那些,优选Ni,Pd,Pt、Ru或Rh(或者直接、呈负载形式如经由活性炭、Al、ZrO2、TiO2、SiO2、碳酸盐等负载或以化合物如氧化钯或氧化铂)存在下的氢气;或金属氢化物,半金属氢化物如氢化铝和衍生于其的氢化物如氢化铝锂、二异丁基氢化铝,硼氢化物如乙硼烷或衍生于其的硼烷化物(boranate)如硼氢化钠或硼氢化锂。
合适的溶剂是脂族烃类如戊烷、己烷、环己烷和C5-C8链烷烃的混合物,芳族烃类如甲苯、邻二甲苯、间二甲苯和对二甲苯,醚类如乙醚、二异丙基醚、叔丁基甲基醚、二烷、茴香醚和四氢呋喃,二醇醚如二甲基乙二醇醚、二乙基乙二醇醚、二甘醇二甲基醚,酯如乙酸乙酯、乙酸丙酯、异丁酸甲酯、乙酸异丁酯,羧酰胺如N,N-二甲基甲酰胺、N-甲基吡咯烷酮、N,N-二甲基乙酰胺,腈类如乙腈和丙腈,醇如甲醇、乙醇、正丙醇、异丙醇、正丁醇和叔丁醇,特别优选甲苯和甲醇。
还可以使用所述溶剂的混合物。
后处理可以以已知方式进行。
用于将胺II转化成化合物I的方法取决于基团Y的性质。对于Y的各值,该制备方法与用于由其中R3和R4也为H的化合物II开始制备其中R3和R4为H的对应化合物I的方法相同。这些方法尤其描述于JP2009137851(Y45),CN1687061(Y51),CN1597681(Y12),WO04/087694(Y65),CN1515560(Y12),CN1355164(Y66),CN1355163(Y56),CN1325849(Y12),WO02/070476(Y1),WO02/042275(Y42),WO02/038562(Y20),WO020/24704(Y21),EP1157991(Y12),EP1095935(Y52),WO01/000602(Y13),JP2000219679(Y17),JP11292720(Y15),EP902029(Y56),EP863142(Y19),WO98/14452(Y56),WO98/07720(Y42),WO97/47626(Y14),WO93/15074(Y1,Y2,Y3,Y5),WO94/14817(Y21),WO97/28127(Y40,Y41),WO97/11060(Y46),WO97/07104(Y55),WO97/06150(Y45),WO94/05668(Y13),WO96/20195(Y14),WO96/18618(Y21),WO96/02523(Y37),EP688773(Y13),EP683160(Y35),JP07304759(Y32),WO95/22547(Y2,Y12,Y20),WO95/23509(Y13),EP640600(Y60),WO92/06962(Y2),WO93/15074(Y3),JP06016664(Y33),EP568041(Y56),WO93/19065(Y13),JP05213970(Y37),JP05140155(Y56),WO93/03043(Y39),WO92/21684(Y37),JP04145087(Y37),WO92/06962(Y2),WO92/02509(Y2),EP454444(Y50),EP448188(Y39),JP03081275(Y2),EP422639(Y17),EP415642(Y50),DE3922107(Y14,Y31),WO90/10626(Y31),EP371240(Y63,Y64),EP334055(Y17,Y20,Y38),EP349832(Y21),EP338533(Y14,Y31),EP328001(Y31),JP01139580(Y11,Y17,Y55),EP311135(Y13,Y17,Y21,Y38,Y39),EP305923(Y23),US4830659(Y37),EP304935(Y17),EP304920(Y37),JP63222167(Y1),WO88/05264(Y20),EP273417(Y37)和EP176101(Y37)中。
硝基化合物III又可以由相应的苯基化合物IV得到:
苯基化合物IV的硝化通常在-20℃至100℃,特别优选0-20℃下进行(Organikum,Heidelberg,1993,第553-557页)。
合适的硝化剂是H2SO4conc和HNO3conc的混合物,优选比例范围50∶1-1∶50,更优选20∶1-1∶20,尤其优选10∶1-1∶10。
后处理可以以已知方式进行。
其中R2为C3-C6链烯基、C3-C6卤代链烯基、C3-C6炔基或C3-C6卤代炔基,优选C3-C6炔基的那些硝基化合物III还可以通过烷基化其中R2为H的硝基化合物III制备:
该反应通常在-78℃至反应混合物的沸点,优选-40℃至100℃,特别优选-20℃至30℃下在惰性有机溶剂中在碱存在下进行[WO02/066471]。
合适的溶剂是脂族烃类如戊烷、己烷、环己烷和C5-C8链烷烃的混合物,芳族烃类如甲苯、邻二甲苯、间二甲苯和对二甲苯,卤代烃类如二氯甲烷、1,2-二氯乙烷、氯仿和氯苯,醚类如乙醚、二异丙基醚、叔丁基甲基醚、二烷、茴香醚和四氢呋喃,二醇醚如二甲基乙二醇醚、二乙基乙二醇醚、二甘醇二甲基醚,酯类如乙酸乙酯、乙酸丙酯、异丁酸甲酯、乙酸异丁酯,羧酰胺类如N,N-二甲基甲酰胺、N-甲基吡咯烷酮、N,N-二甲基乙酰胺,腈类如乙腈和丙腈,酮类如丙酮、甲基乙基酮、二乙基酮和叔丁基甲基酮,以及二甲亚砜。特别优选醚类如乙醚、二异丙基醚、叔丁基甲基醚、二烷、茴香醚和四氢呋喃。还可以使用所述溶剂的混合物。
合适的碱通常为无机化合物,如碱金属和碱土金属氢化物,如氢化锂、氢化钠、氢化钾和氢化钙,碱金属和碱土金属碳酸盐,如碳酸锂、碳酸钾和碳酸钙,以及碱金属碳酸氢盐,如碳酸氢钠,碱金属和碱土金属醇盐,如甲醇钠、乙醇钠、乙醇钾、叔丁醇钾、叔戊醇钾和二甲氧基镁,此外还有有机碱,如叔胺如三甲胺、三乙胺、二异丙基乙基胺和N-甲基哌啶,吡啶,取代吡啶如可力丁、卢剔啶、N-甲基吗啉和4-二甲氨基吡啶以及还有双环胺。特别优选叔胺,如三甲胺、三乙胺、二异丙基乙基胺以及碱金属和碱土金属醇盐,如甲醇钠、乙醇钠、乙醇钾。
碱通常以催化量使用;然而,它们还可以以等摩尔量、过量使用或者合适的话可以用作溶剂。
后处理可以以已知方式进行。
苯基化合物IV又可以由相应的乙酰胺V得到:
乙酰胺V的环化通常在0℃至反应混合物的沸点,优选0-140℃,特别优选20-120℃下在惰性有机溶剂中在碱存在下进行[WO02/066471]。
L4为卤素,选自Cl、Br、I;优选Cl或Br;最优选Cl,还最优选Br。
合适的溶剂是脂族烃类如戊烷、己烷、环己烷和C5-C8链烷烃的混合物,芳族烃类如甲苯、邻二甲苯、间二甲苯和对二甲苯,卤代烃类如二氯甲烷、1,2-二氯乙烷、氯仿和氯苯,醚类如乙醚、二异丙基醚、叔丁基甲基醚、二烷、茴香醚和四氢呋喃,二醇醚如二甲基乙二醇醚、二乙基乙二醇醚、二甘醇二甲基醚,酯类如乙酸乙酯、乙酸丙酯、异丁酸甲酯、乙酸异丁酯,羧酰胺类如N,N-二甲基甲酰胺、N-甲基吡咯烷酮、N,N-二甲基乙酰胺,腈类如乙腈和丙腈,以及二甲亚砜。
还可以使用所述溶剂的混合物。
合适的碱通常为无机化合物,如碱金属和碱土金属氢氧化物,如氢氧化锂、氢氧化钠、氢氧化钾和氢氧化钙,碱金属和碱土金属氧化物,如氧化锂、氧化钠、氧化钙和氧化镁,碱金属和碱土金属氢化物,如氢化锂、氢化钠、氢化钾和氢化钙,碱金属和碱土金属碳酸盐,如碳酸锂、碳酸钾和碳酸钙,以及碱金属碳酸氢盐,如碳酸氢钠,金属有机化合物,优选碱金属烷基化物,如甲基锂、丁基锂和苯基锂,烷基卤化镁,如甲基氯化镁,以及碱金属和碱土金属醇盐,如甲醇钠、乙醇钠、乙醇钾、叔丁醇钾、叔戊醇钾和二甲氧基镁,此外还有有机碱,如叔胺如三甲胺、三乙胺、二异丙基乙基胺和N-甲基哌啶,吡啶,取代吡啶如可力丁、卢剔啶、N-甲基吗啉和4-二甲氨基吡啶以及还有双环胺。特别优选1,8-二氮杂双环[5.4.0]十一碳-7-烯(DBU)。
碱通常以催化量使用;然而,它们还可以以等摩尔量、过量使用或者合适的话可以用作溶剂。
后处理可以以已知方式进行。
乙酰胺V又可以由对应的苯酚VI得到:
该反应通常在-78℃至反应混合物的沸点,优选-40℃至100℃,特别优选-20℃至30℃下在惰性有机溶剂中在碱存在下进行[WO02/066471]。
L4为卤素,选自Cl、Br、I,优选Cl或Br,最优选Cl,还最优选Br。
L5是用于酰化的已知活化基团,例如卤素或C1-C6烷氧基,优选Cl或C1-C6烷氧基,最优选Cl、OCH3或OC2H5。
合适的溶剂是脂族烃类如戊烷、己烷、环己烷和C5-C8链烷烃的混合物,芳族烃类如甲苯、邻二甲苯、间二甲苯和对二甲苯,卤代烃类如二氯甲烷、1,2-二氯乙烷、氯仿和氯苯,醚类如乙醚、二异丙基醚、叔丁基甲基醚、二烷、茴香醚和四氢呋喃,二醇醚如二甲基乙二醇醚、二乙基乙二醇醚、二甘醇二甲基醚,酯类如乙酸乙酯、乙酸丙酯、异丁酸甲酯、乙酸异丁酯,羧酰胺类如N,N-二甲基甲酰胺、N-甲基吡咯烷酮、N,N-二甲基乙酰胺,腈类如乙腈和丙腈,酮类如丙酮、甲基乙基酮、二乙基酮和叔丁基甲基酮,以及二甲亚砜。
特别优选醚类如乙醚、二异丙基醚、叔丁基甲基醚、二烷、茴香醚和四氢呋喃。
还可以使用所述溶剂的混合物。
合适的碱通常为无机化合物,如碱金属和碱土金属氢化物,如氢化锂、氢化钠、氢化钾和氢化钙,碱金属和碱土金属碳酸盐,如碳酸锂、碳酸钾和碳酸钙,以及碱金属碳酸氢盐,如碳酸氢钠,碱金属和碱土金属醇盐,如甲醇钠、乙醇钠、乙醇钾、叔丁醇钾、叔戊醇钾和二甲氧基镁,此外还有有机碱,如叔胺如三甲胺、三乙胺、二异丙基乙基胺和N-甲基哌啶,吡啶,取代吡啶如可力丁、卢剔啶、N-甲基吗啉和4-二甲氨基吡啶以及还有双环胺。
特别优选叔胺如三甲胺、三乙胺、二异丙基乙基胺以及碱金属和碱土金属醇盐,如甲醇钠、乙醇钠、乙醇钾,
碱通常以催化量使用;然而,它们还可以以等摩尔量、过量使用或者合适的话可以用作溶剂。
后处理可以以已知方式进行。
制备乙酰胺V所需的苯酚VI由文献[WO02/066471]已知或者它们可以按照所引用文献制备和/或可市购。
制备乙酰胺V所需的化合物VII可以市购。
式I的苯并嗪酮类以及包含它们的组合物适合作为除草剂。它们适合直接使用或适合以适当配制的组合物使用。包含式I的苯并嗪酮类的除草组合物非常有效地防治非作物区域的植物生长,尤其是在高施用率下。它们在诸如小麦、稻、玉米、大豆和棉花的作物中作用于阔叶杂草和禾本科杂草而不对农作物造成任何显著的损害。该效果主要在低施用率下观察到。
取决于所述施用方法,式I的苯并嗪酮类或包含它们的组合物可以额外用于许多其他农作物以消除不希望的植物。合适的作物实例如下:洋葱(Alliumcepa)、凤梨(Ananascomosus)、落花生(Arachishypogaea)、石刁柏(Asparagusofficinalis)、燕麦(Avenasativa)、甜菜(Betavulgarisspec.altissima)、甜菜(Betavulgarisspec.rapa)、欧洲油菜(Brassicanapusvar.napus)、芜青甘蓝(Brassicanapusvar.napobrassica)、芜青(Brassicarapavar.silvestris)、羽衣甘蓝(Brassicaoleracea)、黑芥(Brassicanigra)、大叶茶(Camelliasinensis)、红花(Carthamustinctorius)、美国山核桃(Caryaillinoinensis)、柠檬(Citruslimon)、甜橙(Citrussinensis)、小果咖啡(Coffeaarabica)(中果咖啡(Coffeacanephora)、大果咖啡(Coffealiberica))、黄瓜(Cucumissativus)、狗牙根(Cynodondactylon)、胡萝卜(Daucuscarota)、油棕(Elaeisguineensis)、欧洲草莓(Fragariavesca)、大豆(Glycinemax)、陆地棉(Gossypiumhirsutum)(树棉(Gossypiumarboreum)、草棉(Gossypiumherbaceum)、Gossypiumvitifolium)、向日葵(Helianthusannuus)、Heveabrasiliensis、大麦(Hordeumvulgare)、啤酒花(Humuluslupulus)、甘薯(Ipomoeabatatas)、核桃(Juglansregia)、兵豆(Lensculinaris)、亚麻(Linumusitatissimum)、番茄(Lycopersiconlycopersicum)、苹果属(Malusspec.)、木薯(Manihotesculenta)、紫苜蓿(Medicagosativa)、芭蕉属(Musaspec.)、烟草(Nicotianatabacum)(黄花烟草(N.rustica))、油橄榄(Oleaeuropaea)、稻(Oryzasativa)、金甲豆(Phaseoluslunatus)、菜豆(Phaseolusvulgaris)、欧洲云杉(Piceaabies)、松属(Pinusspec.)、开心果(Pistaciavera)、Pisumsativum、欧洲甜樱桃(Prunusavium)、Prunuspersica、西洋梨(Pyruscommunis)、杏(Prunusarmeniaca)、欧洲酸樱桃(Prunuscerasus)、扁桃(Prunusdulcis)和欧洲李(Prunusdomestica)、Ribessylvestre、蓖麻(Ricinuscommunis)、甘蔗(Saccharumofficinarum)、黑麦(Secalecereale)、白芥(Sinapisalba)、马铃薯(Solanumtuberosum)、两色蜀黍(Sorghumbicolor)(高粱(S.vulgare))、可可树(Theobromacacao)、红车轴草(Trifoliumpratense)、普通小麦(Triticumaestivum)、小黑麦(Triticale)、硬粒小麦(Triticumdurum)、蚕豆(Viciafaba)、葡萄(Vitisvinifera)和玉蜀黍(Zeamays)。
优选的作物如下:落花生(Arachishypogaea)、甜菜(Betavulgarisspec.altissima)、欧洲油菜(Brassicanapusvar.napus)、羽衣甘蓝(Brassicaoleracea)、柠檬(Citruslimon)、甜橙(Citrussinensis)、小果咖啡(Coffeaarabica)(中果咖啡(Coffeacanephora)、大果咖啡(Coffealiberica))、狗牙根(Cynodondactylon)、大豆(Glycinemax)、陆地棉(Gossypiumhirsutum)(树棉(Gossypiumarboreum)、草棉(Gossypiumherbaceum)、Gossypiumvitifolium)、向日葵(Helianthusannuus)、大麦(Hordeumvulgare)、核桃(Juglansregia)、兵豆(Lensculinaris)、亚麻(Linumusitatissimum)、番茄(Lycopersiconlycopersicum)、苹果属(Malusspec.)、紫苜蓿(Medicagosativa)、烟草(Nicotianatabacum)(黄花烟草(N.rustica))、油橄榄(Oleaeuropaea)、稻(Oryzasativa)、金甲豆(Phaseoluslunatus)、菜豆(Phaseolusvulgaris)、开心果(Pistaciavera)、Pisumsativum、扁桃(Prunusdulcis)、甘蔗(Saccharumofficinarum)、黑麦(Secalecereale)、马铃薯(Solanumtuberosum)、两色蜀黍(Sorghumbicolor)(高粱(S.vulgare))、小黑麦(Triticale)、普通小麦(Triticumaestivum)、硬粒小麦(Triticumdurum)、蚕豆(Viciafaba)、葡萄(Vitisvinifera)和玉蜀黍(Zeamays)。
本发明式I的苯并嗪酮类还可以用于基因修饰植物。术语“基因修饰植物”应理解为其基因材料已经通过使用重组DNA技术以在自然情况下不易通过杂交、突变或自然重组得到的方式修饰的植物。通常将一个或多个基因整合到基因修饰植物的基因材料中以改善植物的某些性能。这类基因修饰还包括但不限于蛋白质、寡肽或多肽的靶向翻译后修饰,例如通过糖基化或聚合物加成如异戊二烯化、乙酰化或法呢基化结构部分或PEG结构部分。通过育种、诱变或基因工程修饰的植物例如因常规育种或基因工程方法而耐受特殊类别除草剂的施用,这些除草剂如羟基苯基丙酮酸二加氧酶(HPPD)抑制剂,乙酰乳酸合成酶(ALS)抑制剂,例如磺酰脲类(例如参见US6,222,100,WO01/82685,WO00/026390,WO97/41218,WO98/002526,WO98/02527,WO04/106529,WO05/20673,WO03/14357,WO03/13225,WO03/14356,WO04/16073)或咪唑啉酮类(例如参见US6,222,100,WO01/82685,WO00/26390,WO97/41218,WO98/02526,WO98/02527,WO04/106529,WO05/20673,WO03/014357,WO03/13225,WO03/14356,WO04/16073),烯醇丙酮酰莽草酸3-磷酸合成酶(EPSPS)抑制剂,例如草甘膦(glyphosate)(例如参见WO92/00377),谷氨酰胺合成酶(GS)抑制剂,例如草铵膦(glufosinate)(例如参见EP-A242236,EP-A242246)或苯腈类(oxynil)除草剂(例如参见US5,559,024)。几种栽培植物已经通过常规育种(诱变)方法而耐受除草剂,例如耐受咪唑啉酮类如咪草啶酸(imazamox)的夏播油菜(Canola,德国BASFSE)。使用基因工程方法使栽培植物如大豆、棉花、玉米、甜菜和油菜耐受除草剂如草甘膦和草铵膦,它们中的一些可以以商标名(耐受草甘膦,Monsanto,U.S.A.)和(耐受草铵膦,德国BayerCropScience)得到。
此外,还包括通过使用重组DNA技术能够合成一种或多种杀虫蛋白,尤其是由芽孢杆菌属(Bacillus)细菌菌株,特别是苏云金芽孢杆菌(Bacillusthuringiensis)已知的那些的植物,所述杀虫蛋白如内毒素,例如CryIA(b)、CryIA(c)、CryIF、CryIF(a2)、CryIIA(b)、CryIIIA、CryIIIB(b1)或Cry9c;无性杀虫蛋白(VIP),例如VIP1、VIP2、VIP3或VIP3A;线虫定殖细菌的杀虫蛋白,例如发光杆菌属(Photorhabdus)或致病杆菌属(Xenorhabdus);动物产生的毒素如蝎子毒素、蜘蛛毒素、黄蜂毒素或其他昆虫特异性神经毒素;真菌产生的毒素,例如链霉菌属(Streptomycetes)毒素;植物凝集素,例如豌豆或大麦凝集素;凝集素,蛋白酶抑制剂,例如胰蛋白酶抑制剂,丝氨酸蛋白酶抑制剂,马铃薯储藏蛋白酶抑制剂(patatin),半胱氨酸蛋白酶抑制剂或木瓜蛋白酶抑制剂,核糖体失活蛋白(RIP),例如蓖麻蛋白、玉米-RIP、相思豆毒蛋白、丝瓜籽蛋白、皂草素或异株腹泻毒蛋白(bryodin);类固醇代谢酶,例如3-羟基类固醇氧化酶、蜕皮甾类-IDP糖基转移酶、胆固醇氧化酶、蜕皮激素抑制剂或HMG-CoA还原酶;离子通道阻断剂,例如钠通道或钙通道阻断剂;保幼激素酯酶;利尿激素受体(螺旋激肽(helicokinin)受体);茋合成酶,联苄合成酶,壳多糖酶或葡聚糖酶。在本发明上下文中,这些杀虫蛋白或毒素还应具体理解为前毒素、杂合蛋白、截短的或其他方面改性的蛋白。杂合蛋白的特征在于蛋白域的新型组合(例如参见WO02/015701)。该类毒素或能够合成这些毒素的基因修饰植物的其他实例例如公开于EP-A374753、WO93/007278、WO95/34656、EP-A427529、EP-A451878、WO03/18810和WO03/52073中。生产这些基因修饰植物的方法对本领域技术人员通常是已知的且例如描述于上述出版物中。这些含于基因修饰植物中的杀虫蛋白赋予产生这些蛋白的植物以对所有分类学上为节肢动物的害虫,尤其是甲虫(鞘翅目(Coeleropta))、双翅目昆虫(双翅目(Diptera))和蛾(鳞翅目(Lepidoptera))以及线虫(线虫纲(Nematoda))的耐受性。能够合成一种或多种杀虫蛋白的基因修饰植物例如描述于上述出版物中,它们中的一些可市购,例如(产生毒素Cry1Ab的玉米品种),Plus(产生毒素Cry1Ab和Cry3Bb1的玉米品种),(产生毒素Cry9c的玉米品种),RW(产生毒素Cry34Ab1、Cry35Ab1和酶膦丝菌素-N-乙酰转移酶[PAT]的玉米品种);33B(产生毒素Cry1Ac的棉花品种),I(产生毒素Cry1Ac的棉花品种),II(产生毒素Cry1Ac和Cry2Ab2的棉花品种);(产生VIP毒素的棉花品种);(产生毒素Cry3A的土豆品种); Bt11(例如CB)和法国SyngentaSeedsSAS的Bt176(产生毒素Cry1Ab和PAT酶的玉米品种),法国SyngentaSeedsSAS的MIR604(产生毒素Cry3A的修饰译本的玉米品种,参见WO03/018810),比利时MonsantoEuropeS.A.的MON863(产生毒素Cry3Bb1的玉米品种),比利时MonsantoEuropeS.A.的IPC531(产生毒素Cry1Ac的修饰译本的棉花品种)和比利时PioneerOverseasCorporation的1507(产生毒素Cry1F和PAT酶的玉米品种)。
此外,还包括通过使用重组DNA技术能够合成一种或多种蛋白质以提高对细菌、病毒或真菌病原体的耐受性或抵抗性的植物。这类蛋白质的实例为所谓的“与发病机理相关的蛋白”(PR蛋白,例如参见EP-A392225),植物病害抗性基因(例如表达对来自野生墨西哥土豆Solanumbulbocastanum的致病疫霉(Phytophthorainfestans)起作用的抗性基因的土豆栽培品种)或T4溶菌酶(例如能够合成这些蛋白而对细菌如Erwiniaamylvora具有提高的耐受性的土豆栽培品种)。生产这类基因修饰植物的方法通常为本领域技术人员所已知并且例如描述于上述出版物中。
此外,还包括通过使用重组DNA技术能够合成一种或多种蛋白质以提高产量(例如生物质产量、谷粒产量、淀粉含量、油含量或蛋白质含量),对干旱、盐或其他生长限制环境因素的耐受性或对害虫以及真菌、细菌或其病毒病原体的耐受性的植物。
此外,还包括尤其为了改善人类或动物营养而通过使用重组DNA技术含有改变量的物质含量或新物质含量的植物,例如产生促进健康的长链ω-3脂肪酸或不饱和ω-9脂肪酸的油料作物(例如油菜,加拿大DOWAgroSciences)。
此外,还包括尤其为了改进原料生产而通过使用重组DNA技术含有改变量的物质含量或新物质含量的植物,例如产生增加的支链淀粉含量的土豆(例如土豆,德国BASFSE)。
本发明式I的苯并嗪酮类还可以用于由于基因工程或育种而耐受一种或多种除草剂、由于基因工程或育种而耐受一种或多种病原体如植物病原性真菌或者由于基因工程或育种而耐受昆虫侵袭的农作物。
合适的例如是农作物,优选玉米、小麦、向日葵、甘蔗、棉花、稻、卡罗拉(canola)、油菜籽油菜或大豆,这些作物耐受除草的PPO抑制剂,或者由于通过基因修饰引入用于Bt毒素的基因而耐受某些昆虫侵袭的农作物。
此外,已经发现式I的苯并嗪酮类还适于植物部分的脱叶和/或干燥,对此合适的是农作物如棉花、土豆、油菜籽油菜、向日葵、大豆或蚕豆,尤其是棉花。就此而言,已经发现用于植物干燥和/或脱叶的组合物、制备这些组合物的方法以及使用式I的苯并嗪酮类使植物干燥和/或脱叶的方法。
作为干燥剂,式I的苯并嗪酮类特别适于干燥农作物如土豆、油菜籽油菜、向日葵和大豆以及禾谷类的地上部分。这使得这些重要农作物的完全机械化收获成为可能。
还具有经济益处的是促进柑橘类水果、橄榄和其他品种的仁果、核果和坚果的收获,这通过在一定时间期限内集中裂开或降低对树的粘附而成为可能。相同的机理,即促进水果部分或叶部分与植物的枝部分之间产生脱离组织对于有用植物,尤其是棉花的受控脱叶也是必要的。
此外,各棉花植株成熟的时间间隔缩短导致收获后的纤维质量提高。
式I的苯并嗪酮类或包含式I的苯并嗪酮类的除草组合物例如可以以即喷水溶液,粉末,悬浮液以及高度浓缩的水性、油性或其它悬浮液或分散体,乳液,油分散体,糊,粉剂,撒播用材料或颗粒的形式通过喷雾、雾化、撒粉、撒播、浇灌或处理种子或与种子混合而使用。使用形式取决于意欲的目的;在每种情况下都应确保本发明活性成分的最佳可能分布。
除草组合物包含除草有效量的至少一种式I的苯并嗪酮类和常用于配制作物保护剂的助剂。
常用于配制作物保护剂的助剂实例是惰性助剂,固体载体,表面活性剂(如分散剂、保护性胶体、乳化剂、润湿剂和增粘剂),有机和无机增稠剂,杀菌剂,防冻剂,消泡剂,任选还有着色剂以及用于种子配制剂的粘合剂。
本领域技术人员充分知晓该类配制剂的配方。
增稠剂(即赋予配制剂以改性的流动性能,即静止状态下的高粘度和运动状态下的低粘度的化合物)的实例是多糖,如黄原胶(来自Kelco的),23(RhonePoulenc)或(来自R.T.Vanderbilt),以及有机和无机层状矿物,如(来自Engelhard)。消泡剂实例是聚硅氧烷乳液(如SRE,Wacker或来自Rhodia),长链醇,脂肪酸,脂肪酸盐,有机氟化合物及其混合物。
可以加入杀菌剂以稳定含水除草配制剂。杀菌剂实例是基于双氯芬和苄醇半缩甲醛的杀菌剂(ICI的或ThorChemie的RS以及Rohm&Haas的MK),还有异噻唑啉酮衍生物,如烷基异噻唑啉酮类和苯并异噻唑啉酮类(ThorChemie的ActicideMBS)。
防冻剂实例是乙二醇、丙二醇、脲或甘油。
着色剂的实例是微水溶性颜料和水溶性染料。可以提到的实例是以如下名称已知的染料:若丹明B,C.I.颜料红112和C.I.溶剂红1,以及颜料蓝15:4,颜料蓝15:3,颜料蓝15:2,颜料蓝15:1,颜料蓝80,颜料黄1,颜料黄13,颜料红112,颜料红48:2,颜料红48:1,颜料红57:1,颜料红53:1,颜料橙43,颜料橙34,颜料橙5,颜料绿36,颜料绿7,颜料白6,颜料棕25,碱性紫10,碱性紫49,酸性红51,酸性红52,酸性红14,酸性蓝9,酸性黄23,碱性红10,碱性红108。
粘合剂的实例是聚乙烯吡咯烷酮、聚乙酸乙烯酯、聚乙烯醇和纤基乙酸钠。
合适的惰性助剂例如为下列物质:中沸点到高沸点的矿物油馏分如煤油和柴油,此外还有煤焦油和植物或动物来源的油,脂族、环状和芳族烃如石蜡,四氢化萘,烷基化萘及其衍生物,烷基化苯及其衍生物,醇类如甲醇、乙醇、丙醇、丁醇和环己醇,酮类如环己酮或强极性溶剂,例如胺类如N-甲基吡咯烷酮,以及水。
合适的载体包括液体和固体载体。液体载体例如包括非水溶剂如环状和芳族烃类,例如石蜡,四氢化萘,烷基化萘及其衍生物,烷基化苯及其衍生物,醇类如甲醇、乙醇、丙醇、丁醇和环己醇,酮类如环己酮或强极性溶剂,例如胺类如N-甲基吡咯烷酮,以及水,及其混合物。
固体载体例如包括矿土如硅石、硅胶、硅酸盐、滑石、高岭土、石灰石、石灰、白垩、红玄武土、黄土、粘土、白云石、硅藻土、硫酸钙、硫酸镁和氧化镁,磨碎的合成材料,肥料如硫酸铵、磷酸铵、硝酸铵和脲类以及植物来源的产品如谷粉、树皮粉、木粉和坚果壳粉,纤维素粉或其它固体载体。
合适的表面活性剂(助剂、润湿剂、增粘剂、分散剂和乳化剂)是芳族磺酸如木素磺酸(例如Borrespers类型,Borregaard)、苯酚磺酸、萘磺酸(Morwet类型,AkzoNobel)和二丁基萘磺酸(Nekal类型,BASFSE)以及脂肪酸的碱金属盐、碱土金属盐和铵盐,烷基-和烷基芳基磺酸盐,烷基硫酸盐,月桂基醚硫酸盐和脂肪醇硫酸盐,以及硫酸化十六-、十七-和十八烷醇的盐,还有脂肪醇乙二醇醚的盐,磺化萘及其衍生物与甲醛的缩合物,萘或萘磺酸与苯酚和甲醛的缩合物,聚氧乙烯辛基酚醚,乙氧基化异辛基-、辛基-或壬基酚,烷基苯基或三丁基苯基聚乙二醇醚,烷基芳基聚醚醇,异十三烷醇,脂肪醇/氧化乙烯缩合物,乙氧基化蓖麻油,聚氧乙烯烷基醚或聚氧丙烯烷基醚,月桂醇聚乙二醇醚乙酸酯,山梨糖醇酯,木素亚硫酸盐废液和蛋白质,变性蛋白质,多糖(如甲基纤维素),疏水改性的淀粉,聚乙烯醇(Mowiol类型,Clariant),聚羧酸盐类(BASFSE,Sokalan类型),聚烷氧基化物,聚乙烯胺(BASFSE,Lupamine类型),聚乙烯亚胺(BASFSE,Lupasol类型),聚乙烯基吡咯烷酮及其共聚物。
粉末、撒播材料和粉剂可以通过将活性成分与固体载体混合或同时研磨来制备。
颗粒如包衣颗粒、浸渍颗粒和均质颗粒可以通过使活性成分与固体载体粘附而制备。
含水使用形式可以通过添加水由乳液浓缩物、悬浮液、糊、可湿性粉末或水分散性颗粒制备。
为了制备乳液、糊或油分散体,可以借助湿润剂、增粘剂、分散剂或乳化剂将式I的苯并嗪酮类直接或溶于油或溶剂之后在水中均化。或者还可以制备包含活性化合物、湿润剂、增粘剂、分散剂或乳化剂以及需要的话,溶剂或油的浓缩物,该类浓缩物适于用水稀释。
式I的苯并嗪酮类在即用型制剂(配制剂)中的浓度可以在宽范围内变化。配制剂通常包含约0.001-98重量%,优选0.01-95重量%至少一种活性成分。活性成分以90-100%,优选95-100%(根据NMR光谱)的纯度使用。
在本发明式I的苯并嗪酮类的配制剂中,活性成分,例如式I的苯并嗪酮类,以悬浮、乳化或溶解形式存在。本发明配制剂可以呈水溶液,粉末,悬浮液以及高度浓缩的水性、油性或其它悬浮液或分散体,含水乳液,含水微乳液,含水悬浮液,油分散体,糊,粉剂,撒播用材料或颗粒的形式。
本发明式I的苯并嗪酮类例如可以按如下配制:
1.用水稀释的产品
A水溶性浓缩物
将10重量份活性化合物溶于90重量份水或水溶性溶剂中。或者,加入湿润剂或其它助剂。活性化合物经水稀释溶解。这得到活性化合物含量为10重量%的配制剂。
B分散性浓缩物
将20重量份活性化合物溶于70重量份环己酮中并加入10重量份分散剂如聚乙烯基吡咯烷酮。用水稀释得到分散体。活性化合物含量为20重量%。
C可乳化浓缩物
将15重量份活性化合物溶于75重量份有机溶剂(如烷基芳烃)中并加入十二烷基苯磺酸钙和蓖麻油乙氧基化物(在每种情况下为5重量份)。用水稀释得到乳液。该配制剂的活性化合物含量为15重量%。
D乳液
将25重量份活性化合物溶于35重量份有机溶剂(如烷基芳烃)中并加入十二烷基苯磺酸钙和蓖麻油乙氧基化物(在每种情况下为5重量份)。借助乳化机(Ultraturrax)将该混合物引入30重量份水中并制成均相乳液。用水稀释得到乳液。该配制剂的活性化合物含量为25重量%。
E悬浮液
在搅拌的球磨机中,将20重量份活性化合物粉碎并加入10重量份分散剂和湿润剂以及70重量份水或有机溶剂,得到细碎活性化合物悬浮液。用水稀释得到稳定的活性化合物悬浮液。该配制剂中活性化合物含量为20重量%。
F水分散性颗粒和水溶性颗粒
将50重量份活性化合物细碎研磨并加入50重量份分散剂和湿润剂,借助工业装置(如挤出机、喷雾塔、流化床)将其制成水分散性或水溶性颗粒。用水稀释得到稳定的活性化合物分散体或溶液。该配制剂的活性化合物含量为50重量%。
G水分散性粉末和水溶性粉末
将75重量份活性化合物在转子-定子磨机中研磨并加入25重量份分散剂、湿润剂和硅胶。用水稀释得到稳定的活性化合物分散体或溶液。该配制剂的活性化合物含量为75重量%。
H凝胶配制剂
在球磨机中混合20重量份活性化合物、10重量份分散剂、1重量份胶凝剂和70重量份水或有机溶剂,得到细悬浮液。用水稀释得到活性化合物含量为20重量%的稳定悬浮液。
2.不经稀释而施用的产品
I粉剂
将5重量份活性化合物细碎研磨并与95重量份细碎高岭土充分混合。这得到活性化合物含量为5重量%的撒粉粉末。
J颗粒(GR,FG,GG,MG)
将0.5重量份活性化合物细碎研磨并结合99.5重量份载体。现行方法是挤出、喷雾干燥或流化床方法。这得到不经稀释而施用的活性化合物含量为0.5重量%的颗粒。
KULV溶液(UL)
将10重量份活性化合物溶于90重量份有机溶剂如二甲苯中。这得到不经稀释而施用的活性化合物含量为10重量%的产品。
含水使用形式可以通过添加水由乳液浓缩物、悬浮液、糊、可湿性粉末或水分散性颗粒制备。
式I的苯并嗪酮类或包含它们的除草组合物可以出苗前、出苗后或种植之前施用,或者与农作物的种子一起施用。还可以通过施用用除草组合物或活性化合物预处理的农作物的种子而施用除草组合物或活性化合物。若活性成分不能被某些农作物良好地耐受,则可以使用其中借助喷雾设备喷雾除草组合物以使它们尽可能不接触敏感农作物的叶子,而使活性成分到达生长在下面的不希望的植物的叶子或裸露的土壤表面的施用技术(后引导,最后耕作程序)。
在另一实施方案中,可以通过处理种子而施用式I的苯并嗪酮类或除草组合物。种子的处理基本包括所有本领域技术人员熟知的基于本发明式I的苯并嗪酮类或由其制备的组合物的程序(拌种、种子包衣、种子撒粉、种子浸泡、种子包膜、种子多层包衣、种子包壳、种子浸滴和种子造粒)。此时可以加以稀释或不加稀释地施用除草组合物。
术语“种子”包括所有类型的种子,如玉米、种子、果实、块茎、秧苗和类似形式。这里优选术语种子描述的是玉米和种子。所用种子可以是上述有用植物的种子,还可以是转基因植物或通过常规育种方法得到的植物的种子。
本发明式I的苯并嗪酮类的施用率(苯并嗪酮类I的总量)为0.1-3000g/ha,优选10-1000g/ha活性物质(a.s.),取决于防治目标、季节、目标植物和生长阶段。
在本发明的另一优选实施方案中,式I的苯并嗪酮类的施用率为0.1-5000g/ha,优选1-2500g/ha或5-2000g/ha活性物质(a.s.)。
在本发明的另一优选实施方案中,式I的苯并嗪酮类的施用率为0.1-1000g/ha,优选1-750g/ha,更优选5-500g/ha活性物质。
为了处理种子,式I的苯并嗪酮类通常以0.001-10kg/100kg种子的量使用。
为了拓宽作用谱并获得协同增效效果,可以将式I的苯并嗪酮类与大量其他除草或生长调节活性成分的代表混合,然后联合施用。合适的混合物组分例如为1,2,4-噻二唑类,1,3,4-噻二唑类,酰胺类,氨基磷酸及其衍生物,氨基三唑类,酰替苯胺类,(杂)芳氧基链烷酸及其衍生物,苯甲酸及其衍生物,苯并噻二嗪酮类,2-芳酰基-1,3-环己烷二酮类,2-杂芳酰基-1,3-环己烷二酮类,杂芳基芳基酮类,苄基异唑烷酮类,间-CF3-苯基衍生物,氨基甲酸酯类,喹啉羧酸及其衍生物,氯代乙酰苯胺类,环己烯酮肟醚衍生物,二嗪类,二氯丙酸及其衍生物,二氢苯并呋喃类,二氢呋喃-3-酮类,二硝基苯胺类,二硝基苯酚类,二苯基醚类,联吡啶类,卤代羧酸及其衍生物,脲类,3-苯基尿嘧啶类,咪唑类,咪唑啉酮类,N-苯基-3,4,5,6-尿嘧啶类,二唑类,环氧乙烷类,酚类,芳氧基-和杂芳氧基苯氧基丙酸酯,苯基乙酸及其衍生物,2-苯基丙酸及其衍生物,吡唑类,苯基吡唑类,哒嗪类,吡啶羧酸及其衍生物,嘧啶基醚类,磺酰胺类,磺酰脲类,三嗪类,三嗪酮类,三唑啉酮类,三唑羧酰胺类,尿嘧啶类,苯基吡唑啉类,异唑啉类及其衍生物。
可能有益的是单独或与其他除草剂组合施用式I的苯并嗪酮类,或者以与其他作物保护试剂的混合物形式施用式I的苯并嗪酮类,例如与用于防治害虫或植物病原性真菌或细菌的试剂一起施用式I的苯并嗪酮类。
还令人感兴趣的是与无机盐溶液的溶混性,所述溶液用于处理营养和痕量元素缺乏。还可以加入其他添加剂如非植物毒性油和油浓缩物。
其他除草活性组分B优选选自b1)-b15)类除草剂:
b1)类脂生物合成抑制剂;
b2)乙酰乳酸合成酶抑制剂(ALS抑制剂);
b3)光合成抑制剂;
b4)原卟啉原-IX氧化酶抑制剂,
b5)漂白剂除草剂;
b6)烯醇丙酮酰莽草酸3-磷酸合成酶抑制剂(EPSP抑制剂);
b7)谷氨酰胺合成酶抑制剂;
b8)7,8-二氢蝶酸合成酶抑制剂(DHP抑制剂);
b9)有丝分裂抑制剂;
b10)非常长链脂肪酸合成抑制剂(VLCFA抑制剂);
b11)纤维素生物合成抑制剂;
b12)去偶剂除草剂;
b13)植物生长素除草剂;
b14)植物生长素输送抑制剂;和
b15)选自溴丁酰草胺(bromobutide)、氯甲丹(chlorflurenol)、氯甲丹(chlorflurenol-methyl)、环庚草醚(cinmethylin)、苄草隆(cumyluron)、茅草枯(dalapon)、棉隆(dazomet)、苯敌快(difenzoquat)、苯敌快(difenzoquat-metilsulfate)、噻节因(dimethipin)、甲胂钠(DSMA)、香草隆(dymron)、敌草腈(endothal)及其盐、乙苯酰草(etobenzanid)、氟燕灵(flamprop)、氟燕灵(flamprop-isopropyl)、甲氟燕灵(flamprop-methyl)、强氟燕灵(flamprop-M-isopropyl)、麦草伏(flamprop-M-methyl)、抑草丁(flurenol)、抑草丁(flurenol-butyl)、调嘧醇(flurprimidol)、膦铵素(fosamine)、膦铵素(fosamine-ammonium)、茚草酮(indanofan)、indaziflam、抑芽丹(maleichydrazide)、氟草磺(mefluidide)、威百亩(metam)、叠氮甲烷(methylazide)、溴甲烷(methylbromide)、苯丙隆(methyl-dymron)、碘甲烷(methyliodide)、甲胂一钠(MSMA)、油酸(oleicacid)、氯嗪草(oxaziclomefone)、壬酸(pelargonicacid)、稗草畏(pyributicarb)、灭藻醌(quinoclamine)、苯氧丙胺津(triaziflam)、灭草环(tridiphane)和6-氯-3-(2-环丙基-6-甲基苯氧基)-4-哒嗪醇(CAS499223-49-3)及其盐和酯的其他除草剂。
优选包含至少一种选自b2、b3、b4、b5、b6、b7、b9、b10和b13类除草剂的除草剂B的那些本发明组合物。
特别优选包含至少一种选自b4、b6和b10类除草剂的除草剂B的那些本发明组合物。
可以与本发明式I的苯并嗪酮类组合使用的除草剂B实例为:
b1)选自如下的类脂生物合成抑制剂:ACC除草剂如枯杀达(alloxydim)、枯杀达(alloxydim-sodium)、丁氧环酮(butroxydim)、烯草酮(clethodim)、炔草酯(clodinafop)、炔草酯(clodinafop-propargyl)、噻草酮(cycloxydim)、氰氟草酯(cyhalofop)、氰氟草酯(cyhalofop-butyl)、氯甲草(diclofop)、禾草灵(diclofop-methyl)、唑禾草灵(fenoxaprop)、唑禾草灵(fenoxaprop-ethyl)、高唑禾草灵(fenoxaprop-P)、高唑禾草灵(fenoxaprop-P-ethyl)、吡氟禾草灵(fluazifop)、吡氟禾草灵(fluazifop-butyl)、精吡氟禾草灵(fluazifop-P)、精吡氟禾草灵(fluazifop-P-butyl)、吡氟氯禾灵(haloxyfop)、吡氟氯禾灵(haloxyfop-methyl)、精吡氟氯禾灵(haloxyfop-P)、精吡氟氯禾灵(haloxyfop-P-methyl)、唑酰草胺(metamifop)、唑啉草酯(pinoxaden)、环苯草酮(profoxydim)、喔草酯(propaquizafop)、喹禾灵(quizalofop)、喹禾灵(quizalofop-ethyl)、喹禾灵(四氢糠基酯)(quizalofop-tefuryl)、精喹禾灵(quizalofop-P)、精喹禾灵(quizalofop-P-ethyl)、精喹禾灵(四氢糠基酯)(quizalofop-P-tefuryl)、稀禾定(sethoxydim)、醌肟草(tepraloxydim)和肟草酮(tralkoxydim),以及非ACC除草剂如呋草黄(benfuresate)、苏达灭(butylate)、草灭特(cycloate)、茅草枯(dalapon)、哌草丹(dimepiperate)、扑草灭(EPTC)、禾草畏(esprocarb)、乙呋草黄(ethofumesate)、四氟丙酸(flupropanate)、草达灭(molinate)、坪草丹(orbencarb)、克草猛(pebulate)、苄草丹(prosulfocarb)、TCA、杀草丹(thiobencarb)、丁草威(tiocarbazil)、野麦畏(triallate)和灭草猛(vernolate);
b2)选自如下的ALS抑制剂:磺酰脲类,如磺氨黄隆(amidosulfuron)、四唑黄隆(azimsulfuron)、苄嘧黄隆(bensulfuron)、苄嘧黄隆(bensulfuron-methyl)、氯嘧黄隆(chlorimuron)、氯嘧黄隆(chlorimuron-ethyl)、绿黄隆(chlorsulfuron)、醚黄隆(cinosulfuron)、环丙黄隆(cyclosulfamuron)、胺苯黄隆(ethametsulfuron)、胺苯黄隆(ethametsulfuron-methyl)、乙氧嘧黄隆(ethoxysulfuron)、啶嘧黄隆(flazasulfuron)、氟吡磺隆(flucetosulfuron)、氟定黄隆(flupyrsulfuron)、氟定黄隆(flupyrsulfuron-methyl-sodium)、甲酰氨磺隆(foramsulfuron)、吡氯黄隆(halosulfuron)、吡氯黄隆(halosulfuron-methyl)、啶咪黄隆(imazosulfuron)、碘黄隆(iodosulfuron)、碘甲黄隆钠(iodosulfuron-methyl-sodium)、甲基二磺隆(mesosulfuron)、metazosulfuron、甲黄隆(metsulfuron)、甲黄隆(metsulfuron-methyl)、烟嘧黄隆(nicosulfuron)、嘧苯胺磺隆(orthosulfamuron)、环丙氧黄隆(oxasulfuron)、氟嘧黄隆(primisulfuron)、氟嘧黄隆(primisulfuron-methyl)、propyrisulfuron、氟丙黄隆(prosulfuron)、吡嘧黄隆(pyrazosulfuron)、吡嘧黄隆(pyrazosulfuron-ethyl)、玉嘧黄隆(rimsulfuron)、嘧黄隆(sulfometuron)、嘧黄隆(sulfometuron-methyl)、乙黄黄隆(sulfosulfuron)、噻黄隆(thifensulfuron)、噻黄隆(thifensulfuron-methyl)、醚苯黄隆(triasulfuron)、苯黄隆(tribenuron)、苯黄隆(tribenuron-methyl)、三氟啶磺隆(trifloxysulfuron)、氟胺磺隆(triflusulfuron)、氟胺磺隆(triflusulfuron-methyl)和三氟甲磺隆(tritosulfuron),咪唑啉酮类如咪草酯(imazamethabenz)、咪草酯(imazamethabenz-methyl)、咪草啶酸(imazamox)、甲基咪草烟(imazapic)、灭草烟(imazapyr)、灭草喹(imazaquin)和咪草烟(imazethapyr),三唑并嘧啶类除草剂和磺酰苯胺类如唑嘧磺胺酸(cloransulam)、唑嘧磺胺盐(cloransulam-methyl)、唑嘧磺胺(diclosulam)、氟唑啶草(flumetsulam)、双氟磺草胺(florasulam)、唑草磺胺(metosulam)、五氟磺草胺(penoxsulam)、pyrimisulfan和啶磺草胺(pyroxsulam),嘧啶基苯甲酸酯类如双嘧苯甲酸(bispyribac)、双嘧苯甲酸钠(bispyribac-sodium)、嘧苯草肟(pyribenzoxim)、环酯草醚(pyriftalid)、肟啶草(pyriminobac)、肟啶草(pyriminobac-methyl)、嘧硫苯甲酸(pyrithiobac)、嘧硫苯甲酸钠(pyrithiobac-sodium)、4-[[[2-[(4,6-二甲氧基-2-嘧啶基)氧基]苯基]甲基]氨基]苯甲酸1-甲基乙基酯(CAS420138-41-6)、4-[[[2-[(4,6-二甲氧基-2-嘧啶基)氧基]苯基]甲基]氨基]苯甲酸丙基酯(CAS420138-40-5)、N-(4-溴苯基)-2-[(4,6-二甲氧基-2-嘧啶基)氧基]苯甲胺(CAS420138-01-8)以及磺酰氨基羰基三唑啉酮类除草剂如氟酮磺隆(flucarbazone)、氟酮磺隆钠(flucarbazone-sodium)、丙苯磺隆(propoxycarbazone)、丙苯磺隆(propoxycarbazone-sodium)、thiencarbazone和thiencarbazone-methyl。其中本发明的优选实施方案涉及包含至少一种咪唑啉酮类除草剂的那些组合物;
b3)选自如下的光合成抑制剂:胺唑草酮(amicarbazone),光合系统II抑制剂,例如三嗪类除草剂,包括氯代三嗪类、三嗪酮类、三嗪二酮类、甲硫基三嗪类和哒嗪酮类除草剂,如莠灭净(ametryn)、莠去津(atrazine)、杀草敏(chloridazone)、草净津(cyanazine)、敌草净(desmetryn)、戊草津(dimethametryn)、六嗪同(hexazinone)、赛克津(metribuzin)、扑灭通(prometon)、扑草净(prometryn)、扑灭津(propazine)、西玛津(simazine)、西草净(simetryn)、甲氧去草净(terbumeton)、特丁津(terbuthylazin)、去草净(terbutryn)和草达津(trietazin);芳基脲类如氯溴隆(chlorobromuron)、绿麦隆(chlorotoluron)、枯草隆(chloroxuron)、丁隆(dimefuron)、敌草隆(diuron)、伏草隆(fluometuron)、异丙隆(isoproturon)、异恶隆(isouron)、利谷隆(linuron)、苯嗪草(metamitron)、噻唑隆(methabenzthiazuron)、色满隆(metobenzuron)、甲氧隆(metoxuron)、绿谷隆(monolinuron)、草不隆(neburon)、环草隆(siduron)、丁唑隆(tebuthiuron)和赛二唑素(thidiazuron),苯基氨基甲酸酯类如异苯敌草(desmedipham)、卡草灵(karbutilat)、苯敌草(phenmedipham)、乙苯敌草(phenmedipham-ethyl),腈类除草剂如杀草全(bromofenoxim)、溴苯腈(bromoxynil)及其盐和酯、碘苯腈(ioxynil)及其盐和酯,尿嘧啶类如除草定(bromacil)、环草定(lenacil)和特草定(terbacil),以及噻草平(bentazon)和噻草平(bentazon-sodium),达草止(pyridatre)、pyridafol、蔬草灭(pentanochlor)和敌稗(propanil)以及光合系统I抑制剂如敌草快阳离子(diquat)、敌草快(diquat-dibromide)、对草快阳离子(paraquat)、对草快(paraquat-dichloride)和对草快(paraquat-dimetilsulfate)。其中本发明的优选实施方案涉及包含至少一种芳基脲类除草剂的那些组合物。其中本发明的优选实施方案同样涉及包含至少一种三嗪类除草剂的那些组合物。其中本发明的优选实施方案同样涉及包含至少一种腈类除草剂的那些除草剂;
b4)选自如下的原卟啉原-IX氧化酶抑制剂:氟锁草醚(acifluorfen)、氟锁草醚(acifluorfen-sodium)、唑啶炔草(azafenidin)、bencarbazone、双苯嘧草酮(benzfendizone)、治草醚(bifenox)、氟丙嘧草酯(butafenacil)、氟酮唑草(carfentrazone)、氟酮唑草(carfentrazone-ethyl)、氯硝醚(chlomethoxyfen)、吲哚酮草酯(cinidon-ethyl)、异丙吡草酯(fluazolate)、氟哒嗪草酯(flufenpyr)、氟哒嗪草酯(flufenpyr-ethyl)、酰亚胺苯氧乙酸(flumiclorac)、酰亚胺苯氧乙酸戊酯(flumiclorac-pentyl)、氟嗪酮(flumioxazin)、乙羧氟草醚(fluoroglycofen)、乙羧氟草醚(fluoroglycofen-ethyl)、达草氟(fluthiacet)、达草氟(fluthiacet-methyl)、氟黄胺草醚(fomesafen)、氟硝磺酰胺(halosafen)、乳氟禾草灵(lactofen)、炔丙唑草(oxadiargyl)、恶草灵(oxadiazon)、乙氧氟草醚(oxyfluorfen)、戊唑草(pentoxazone)、氟唑草胺(profluazol)、双唑草腈(pyraclonil)、氟唑草酯(pyraflufen)、氟唑草酯(pyraflufen-ethyl)、嘧啶肟草醚(saflufenacil)、磺胺草唑(sulfentrazone)、噻二唑胺(thidiazimin)、[3-[2-氯-4-氟-5-(1-甲基-6-三氟甲基-2,4-二氧代-1,2,3,4-四氢嘧啶-3-基)苯氧基]-2-吡啶氧基]乙酸乙酯(CAS353292-31-6;S-3100)、N-乙基-3-(2,6-二氯-4-三氟甲基苯氧基)-5-甲基-1H-吡唑-1-甲酰胺(CAS452098-92-9)、N-四氢糠基-3-(2,6-二氯-4-三氟甲基苯氧基)-5-甲基-1H-吡唑-1-甲酰胺(CAS915396-43-9)、N-乙基-3-(2-氯-6-氟-4-三氟甲基苯氧基)-5-甲基-1H-吡唑-1-甲酰胺(CAS452099-05-7)、N-四氢糠基-3-(2-氯-6-氟-4-三氟甲基苯氧基)-5-甲基-1H-吡唑-1-甲酰胺(CAS45100-03-7)、3-[7-氟-3-氧代-4-(丙-2-炔基)-3,4-二氢-2H-苯并[1,4]嗪-6-基]-1,5-二甲基-6-硫代-[1,3,5]三嗪烷(triazinan)-2,4-二酮、1,5-二甲基-6-硫代-3-(2,2,7-三氟-3-氧代-4-(丙-2-炔基)-3,4-二氢-2H-苯并[b][1,4]嗪-6-基])-1,3,5-三嗪烷-2,4-二酮、2-(2,2,7-三氟-3-氧代-4-丙-2-炔基-3,4-二氢-2H-苯并[b][1,4]嗪-6-基)-4,5,6,7-四氢异吲哚-1,3-二酮和1-甲基-6-三氟甲基-3-(2,2,7-三氟-3-氧代-4-丙-2-炔基-3,4-二氢-2H-苯并[1,4]嗪-6-基)-1H-嘧啶-2,4-二酮;
b5)选自如下的漂白剂除草剂:PDS抑制剂:氟丁酰草胺(beflubutamid)、吡氟草胺(diflufenican)、氟草同(fluridone)、氟咯草酮(flurochloridone)、呋草酮(flurtamone)、达草灭(norflurazon)、氟吡酰草胺(picolinafen)和4-(3-三氟甲基苯氧基)-2-(4-三氟甲基苯基)嘧啶(CAS180608-33-7),HPPD抑制剂:苯并双环酮(benzobicyclon)、吡草酮(benzofenap)、异恶草酮(clomazone)、异氟草(isoxaflutole)、甲基磺草酮(mesotrione)、pyrasulfotole、吡唑特(pyrazolynate)、苄草唑(pyrazoxyfen)、磺草酮(sulcotrione)、tefuryltrione、tembotrione、topramezone和bicyclopyrone,漂白剂,未知目标:苯草醚(aclonifen)、杀草强(amitrole)和flumeturon;
b6)选自如下的EPSP合成酶抑制剂:草甘膦、草甘膦异丙胺盐(glyphosate-isopropylammonium)、草甘膦钾和草硫膦(glyphosate-trimesium)(sulfosate);
b7)选自如下的谷氨酰胺合成酶抑制剂:双丙氨酰膦(bilanaphos(bialaphos))、双丙氨酰膦(bilanaphos-sodium)、草铵膦、草铵膦(glufosinate-P)和草铵膦(glufosinate-ammonium);
b8)选自如下的DHP合成酶抑制剂:黄草灵(asulam);
b9)选自如下的有丝分裂抑制剂:K1组化合物:二硝基苯胺类如氟草胺(benfluralin)、地乐胺(butralin)、敌乐胺(dinitramine)、丁氟消草(ethalfluralin)、氟消草(fluchloralin)、黄草消(oryzalin)、胺硝草(pendimethalin)、氨基丙氟灵(prodiamine)和氟乐灵(trifluralin),氨基磷酸酯类如胺草磷(amiprophos)、甲基胺草磷(amiprophos-methyl)和草胺磷(butamiphos),苯甲酸类除草剂如敌草索(chlorthal)、敌草索(chlorthal-dimethyl),吡啶类如氟硫革定(dithiopyr)和噻氟啶草(thiazopyr),苯甲酰胺类如拿草特(propyzamide)和丙戊草胺(tebutam),K2组化合物:氯苯胺灵(chlorpropham)、苯胺灵(propham)和长杀草(carbetamide);其中优选K1组化合物,尤其优选二硝基苯胺类;
b10)选自如下的VLCFA抑制剂:氯乙酰胺类如乙草胺(acetochlor)、甲草胺(alachlor)、丁草胺(butachlor)、克草胺(dimethachlor)、噻吩草胺(dimethanamid)、精噻吩草胺(dimethenamid-P)、吡草胺(metazachlor)、异丙甲草胺(metolachlor)、S-异丙甲草胺(metolachlor-S)、烯草胺(pethoxamid)、丙草胺(pretilachlor)、扑草胺(propachlor)、异丙草胺(propisochlor)和噻醚草胺(thenylchlor),羟基乙酰苯胺类(oxyacetanilide)如氟噻草胺(flufenacet)和苯噻草胺(mefenacet),乙酰苯胺类如草乃敌(diphenamid)、萘丙胺(naproanilide)和草萘胺(napropamide),四唑啉酮类如四唑酰草胺(fentrazamide)以及其他除草剂如莎稗磷(anilofos)、唑草胺(cafenstrole)、fenoxasulfone、ipfencarbazone、哌草磷(piperophos)、派罗克杀草砜(pyroxasulfone)和式II#的异唑啉化合物:
其中R21#、R22#、R23#、R24#、W、Z和n具有下列含义:
R21#、R22#、R23#、R24#相互独立地为氢、卤素或C1-C4烷基;
W为苯基或除了碳环成员外还含有1、2或3个选自氧、氮和硫的相同或不同杂原子作为环成员的单环5、6、7、8、9或10员杂环,其中苯基和杂环基未被取代或带有1、2或3个选自卤素、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基和C1-C4卤代烷氧基的取代基Ryy;
优选苯基或除了碳环成员外还含有1、2或3个氮原子作为环成员的5或6员芳族杂环基(杂芳基),其中苯基和杂芳基未被取代或带有1、2或3个取代基Ryy;
Z为氧或NH;以及
n为0或1;
在式II#的异唑啉化合物中,优选如下式II#的异唑啉化合物,其中R21#、R22#、R23#、R24#相互独立地为H、F、Cl或甲基;
Z为氧;
n为0或1;和
W为苯基、吡唑基或1,2,3-三唑基,其中后提到的三个基团未被取代或带有1、2或3个取代基Ryy,尤其是下列基团之一:
其中
R25#为卤素、C1-C4烷基或C1-C4卤代烷基;
R26#为C1-C4烷基;
R27#为卤素、C1-C4烷氧基或C1-C4卤代烷氧基;
R28#为卤素、C1-C4烷基、C1-C4卤代烷基或C1-C4卤代烷氧基;
m为0、1、2或3;和
#表示与基团CR23#R24#的连接点;
在式II#的异唑啉化合物中,尤其优选如下那些式II#的异唑啉化合物,其中
R21#为氢;
R22#为氟;
R23#为氢或氟;
R24#为氢或氟;
W为式W1、W2、W3或W4的基团之一:
其中#表示与基团CR23#R24#的连接点;
Z为氧;
n为0或1,尤其是1;以及
其中尤其优选式II#.1、II#.2、II#.3、II#.4、II#.5、II#.6、II#.7、II#.8和II#.9的异唑啉化合物:
式II#的异唑啉化合物在现有技术中是已知的,例如由WO2006/024820,WO2006/037945,WO2007/071900和WO2007/096576已知;
在VLCFA抑制剂中,优选氯代乙酰胺类和羟基乙酰胺类;
b11)选自如下的纤维素生物合成抑制剂:草克乐(chlorthiamid)、敌草腈(dichlobenil)、胺草唑(flupoxam)、异恶草胺(isoxaben)、1-环己基-5-五氟苯氧基-14-[1,2,4,6]硫杂三嗪-3-基胺和式III的哌嗪化合物:
其中
A为苯基或吡啶基,其中Ra#连接在A与碳原子的连接点的邻位;
Ra#为CN、NO2、C1-C4烷基、D-C3-C6环烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、O-D-C3-C6环烷基、S(O)qRy、C2-C6链烯基、D-C3-C6环烯基、C3-C6链烯氧基、C2-C6炔基、C3-C6炔氧基、NRARB、三-C1-C4烷基甲硅烷基、D-C(=O)-Ra1、D-P(=O)(Ra1)2、苯基、萘基、含有1、2、3或4个选自O、N和S的杂原子且可以被基团Raa和/或Ra1部分或完全取代的经由碳或氮连接的3-7员单环或9或10员双环饱和、不饱和或芳族杂环,以及若Ra与碳原子连接,则额外为卤素;Ry为C1-C6烷基、C3-C4链烯基、C3-C4炔基、NRARB或C1-C4卤代烷基以及q为0、1或2;
RA、RB相互独立地为氢、C1-C6烷基、C3-C6链烯基和C3-C6炔基;RA、RB还可以与它们所连接的氮原子一起形成除了碳原子外可以含有1、2或3个选自O、N和S的杂原子的5或6员饱和、部分或完全不饱和环,该环可以被1-3个基团Raa取代;
D为共价键、C1-C4亚烷基、C2-C6链烯基或C2-C6炔基;
Ra1为氢、OH、C1-C8烷基、C1-C4卤代烷基、C3-C6环烷基、C2-C8链烯基、C5-C6环烯基、C2-C8炔基、C1-C6烷氧基、C1-C4卤代烷氧基、C3-C8链烯氧基、C3-C8炔氧基、NRARB、C1-C6烷氧氨基、C1-C6烷基磺酰氨基、C1-C6烷基氨基磺酰氨基、[二-(C1-C6)烷基氨基]磺酰氨基、C3-C6链烯基氨基、C3-C6炔基氨基、N-(C2-C6链烯基)-N-(C1-C6烷基)氨基、N-(C2-C6炔基)-N-(C1-C6烷基)氨基、N-(C1-C6烷氧基)-N-(C1-C6烷基)氨基、N-(C2-C6链烯基)-N-(C1-C6烷氧基)氨基、N-(C2-C6炔基)-N-(C1-C6烷氧基)氨基、C1-C6烷基磺酰基、三-C1-C4烷基甲硅烷基、苯基、苯氧基、苯基氨基或含有1、2、3或4个选自O、N和S的杂原子的5或6员单环或9或10员双环杂环,其中该环状基团未被取代或被1、2、3或4个基团Raa取代;
Raa为卤素、OH、CN、NO2、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、S(O)qRy、D-C(=O)-Ra1和三-C1-C4烷基甲硅烷基;
Rb#相互独立地为氢、CN、NO2、卤素、C1-C4烷基、C1-C4卤代烷基、C2-C4链烯基、C3-C6炔基、C1-C4烷氧基、C1-C4卤代烷氧基、苄基或S(O)qRy,
Rb与连接于相邻环原子的基团Ra或Rb一起还可以形成除了碳原子外可以含有1、2或3个选自O、N和S的杂原子的5或6员饱和或部分或完全不饱和环,该环可以部分或完全被Raa取代;
p为0、1、2或3;
R30#为氢、OH、CN、C1-C12烷基、C3-C12链烯基、C3-C12炔基、C1-C4烷氧基、C3-C6环烷基、C5-C6环烯基、NRARB、S(O)nRy、S(O)nNRARB、C(=O)R40#、CONRARB、苯基或含有1、2、3或4个选自O、N和S的杂原子的5或6员单环或9或10员双环芳族杂环,其中该环状基团经由D1连接且未被取代或被1、2、3或4个基团Raa取代,以及下列部分或完全被Raa取代的基团:C1-C4烷基、C3-C4链烯基、C3-C4炔基、C1-C4烷氧基、C3-C6环烷基、C5-C6环烯基、NRARB、S(O)nRy、S(O)nRARB、C(=O)R40和CONRARB;
R40#为氢、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基;
D1为羰基或基团D;
其中在基团R15、Ra及其子取代基中,碳链和/或环状基团可以带有1、2、3或4个取代基Raa和/或Ra1;
R31#为C1-C4烷基、C3-C4链烯基或C3-C4炔基;
R32#为OH、NH2、C1-C4烷基、C3-C6环烷基、C3-C6链烯基、C3-C6炔基、C1-C4羟基烷基、C1-C4氰基烷基、C1-C4卤代烷基、C1-C4烷氧基-C1-C4烷基或C(=O)R40;
R33#为氢、卤素、C1-C4烷基或C1-C4卤代烷基,或者R33#和R34#一起为共价键;
R34#、R35#、R36#、R37#相互独立地为氢、卤素、OH、CN、NO2、C1-C4烷基、C1-C4卤代烷基、C2-C6链烯基、C2-C6炔基、C1-C4烷氧基、C1-C4卤代烷氧基、C3-C6环烷基、C3-C6环烯基和C3-C6环炔基;
R38#、R39#相互独立地为氢、卤素、OH、卤代烷基、NRARB、NRAC(O)R41、CN、NO2、C1-C4烷基、C1-C4卤代烷基、C2-C4链烯基、C3-C6炔基、C1-C4烷氧基、C1-C4卤代烷氧基、O-C(O)R41、苯氧基或苄氧基,其中在基团R38#和R39#中碳链和/或环状基团可以带有1、2、3或4个取代基Raa;
R41#为C1-C4烷基或NRARB;
在式III#的哌嗪化合物中,优选如下式III#的哌嗪化合物,其中
A为苯基或吡啶基,其中Ra连接在A与碳原子的连接点的邻位;
Ra#为CN、NO2、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基或D-C(=O)-Ra1;
Ry为C1-C6烷基、C3-C4链烯基、C3-C4炔基、NRARB或C1-C4卤代烷基以及q为0、1或2;
RA、RB相互独立地为氢、C1-C6烷基、C3-C6链烯基和C3-C6炔基;
RA、RB还可以与它们所连接的氮原子一起形成除了碳原子外可以含有1、2或3个选自O、N和S的杂原子的5或6员饱和、部分或完全不饱和环,该环可以被1-3个基团Raa取代;
D为共价键或C1-C4亚烷基;
Ra1为氢、OH、C1-C8烷基、C1-C4卤代烷基、C3-C6环烷基;
Raa为卤素、OH、CN、NO2、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、S(O)qRy、D-C(=O)-Ra1和三-C1-C4烷基甲硅烷基;
Rb#相互独立地为CN、NO2、卤素、C1-C4烷基、C1-C4卤代烷基、C2-C4链烯基、C3-C6炔基、C1-C4烷氧基、C1-C4卤代烷氧基、苄基或S(O)qRy,Rb与连接于相邻环原子的基团Ra或Rb一起还可以形成除了碳原子外可以含有1、2或3个选自O、N和S的杂原子的5或6员饱和或部分或完全不饱和环,该环可以部分或完全被Raa取代;
p为0或1;
R30#为氢、C1-C12烷基、C3-C12链烯基、C3-C12炔基、C1-C4烷氧基或可以部分或完全被基团Raa取代的C(=O)R40#;
R40#为氢、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基;
其中在基团R30#、Ra#及其子取代基中,碳链和/或环状基团可以带有1、2、3或4个取代基Raa和/或Ra1;
R31#为C1-C4烷基;
R32#为OH、NH2、C1-C4烷基、C3-C6环烷基、C1-C4卤代烷基或C(=O)R25;
R33#为氢,或者R33和R34一起为共价键;
R34#、R35#、R36#、R37#相互独立地为氢;
R38#、R39#相互独立地为氢、卤素或OH;
b12)选自如下的去偶剂除草剂:地乐酚(dinoseb)、地乐消酚(dinoterb)以及二硝甲酚(DNOC)及其盐;
b13)选自如下的植物生长素除草剂:2,4-D及其盐和酯、2,4-DB及其盐和酯、氨草啶(aminopyralid)及其盐如氨草啶铵盐(aminopyralid-tris(2-hydroxypropyl)ammonium)及其酯、草除灵(benazolin)、草除灵(benazolin-ethyl)、草灭平(chloramben)及其盐和酯、稗草胺(clomeprop)、二氯皮考啉酸(clopyralid)及其盐和酯、麦草畏(dicamba)及其盐和酯、2,4-滴丙酸(dichlorprop)及其盐和酯、高2,4-滴丙酸(dichlorprop-P)及其盐和酯、氟草烟(fluroxypyr)、氟草烟(fluroxypyr-butometyl)、氟氯胺啶(fluroxypyr-meptyl)、MCPA及其盐和酯、2甲4氯乙硫酯(MCPA-thioethyl)、MCPB及其盐和酯、2甲4氯丙酸(mecoprop)及其盐和酯、高2甲4氯丙酸(mecoprop-P)及其盐和酯、毒莠定(picloram)及其盐和酯、二氯喹啉酸(quinclorac)、喹草酸(quinmerac)、TBA(2,3,6)及其盐和酯、绿草定(triclopyr)及其盐和酯以及aminocyclopyrachlor及其盐和酯;
b14)选自如下的植物生长素输送抑制剂:二氟吡隆(diflufenzopyr)、二氟吡隆(diflufenzopyr-sodium)、抑草生(naptalam)和抑草生(naptalam-sodium);
b15)选自如下的其他除草剂:溴丁酰草胺(bromobutide)、氯甲丹(chlorflurenol)、氯甲丹(chlorflurenol-methyl)、环庚草醚(cinmethylin)、苄草隆(cumyluron)、茅草枯(dalapon)、棉隆(dazomet)、苯敌快(difenzoquat)、苯敌快(difenzoquat-metilsulfate)、噻节因(dimethipin)、甲胂钠(DSMA)、香草隆(dymron)、敌草腈(endothal)及其盐、乙苯酰草(etobenzanid)、氟燕灵(flamprop)、氟燕灵(flamprop-isopropyl)、甲氟燕灵(flamprop-methyl)、强氟燕灵(flamprop-M-isopropyl)、麦草伏(flamprop-M-methyl)、抑草丁(flurenol)、抑草丁(flurenol-butyl)、调嘧醇(flurprimidol)、膦铵素(fosamine)、膦铵素(fosamine-ammonium)、茚草酮(indanofan)、indaziflam、抑芽丹(maleichydrazide)、氟草磺(mefluidide)、威百亩(metam)、methiozolin(CAS403640-27-7)、叠氮甲烷(methylazide)、溴甲烷(methylbromide)、苯丙隆(methyl-dymron)、碘甲烷(methyliodide)、甲胂一钠(MSMA)、油酸(oleicacid)、氯嗪草(oxaziclomefone)、壬酸(pelargonicacid)、稗草畏(pyributicarb)、灭藻醌(quinoclamine)、苯氧丙胺津(triaziflam)、灭草环(tridiphane)和6-氯-3-(2-环丙基-6-甲基苯氧基)-4-哒嗪醇(CAS499223-49-3)及其盐和酯。
此外,可能有用的是将式I的苯并嗪酮类与安全剂组合施用。安全剂是防止或降低对有用植物的损害但不对式I的苯并嗪酮类对不希望的植物的除草作用具有显著影响的化合物。它们可以在播种之前施用(例如在种子处理时、在枝或秧苗上)或以有用植物的出苗前施用或出苗后施用方式施用。安全剂和式I的苯并嗪酮类可以同时或依次施用。
合适的安全剂例如是(喹啉-8-氧基)乙酸类、1-苯基-5-卤代烷基-1H-1,2,4-三唑-3-羧酸、1-苯基-4,5-二氢-5-烷基-1H-吡唑-3,5-二羧酸、4,5-二氢-5,5-二芳基-3-异唑羧酸、二氯乙酰胺类、α-肟基苯基乙腈、苯乙酮肟类、4,6-二卤代-2-苯基嘧啶类、N-[[4-(氨基羰基)苯基]磺酰基]-2-苯甲酰胺类、1,8-萘二甲酸酐、2-卤代-4-卤代烷基-5-噻唑羧酸、硫代磷酸酯类和N-烷基-O-苯基氨基甲酸酯类及其可农用盐和可农用衍生物如酰胺、酯和硫酯,条件是它们具有酸基。
优选安全剂C的实例是解草酮(benoxacor)、喹氧乙酸(cloquintocet)、抑害腈(cyometrinil)、cyprosulfamide、抑害胺(dichlormid)、dicyclonon、dietholate、解草唑(fenchlorazole)、解草啶(fenclorim)、解草安(flurazole)、肟草安(fluxofenim)、解草呋(furilazole)、双苯唑酸(isoxadifen)、吡咯二酸(mefenpyr)、mephenate、萘二甲酸酐(naphthalicanhydride)、解草腈(oxabetrinil)、4-二氯乙酰基-1-氧杂-4-氮杂螺[4.5]癸烷(MON4660,CAS71526-07-3)和2,2,5-三甲基-3-二氯乙酰基-1,3-唑烷(R-29148,CAS52836-31-4)。
尤其优选的安全剂C是解草酮(benoxacor)、喹氧乙酸(cloquintocet)、cyprosulfamide、抑害胺(dichlormid)、解草唑(fenchlorazole)、解草啶(fenclorim)、解草安(flurazole)、肟草安(fluxofenim)、解草呋(furilazole)、双苯唑酸(isoxadifen)、吡咯二酸(mefenpyr)、萘二甲酸酐(naphthalicanhydride)、解草腈(oxabetrinil)、4-二氯乙酰基-1-氧杂-4-氮杂螺[4.5]癸烷(MON4660,CAS71526-07-3)和2,2,5-三甲基-3-二氯乙酰基-1,3-唑烷(R-29148,CAS52836-31-4)。
特别优选的安全剂C是解草酮(benoxacor)、喹氧乙酸(cloquintocet)、cyprosulfamide、抑害胺(dichlormid)、解草唑(fenchlorazole)、解草啶(fenclorim)、解草呋(furilazole)、双苯唑酸(isoxadifen)、吡咯二酸(mefenpyr)、萘二甲酸酐(naphthalicanhydride)、4-二氯乙酰基-1-氧杂-4-氮杂螺[4.5]癸烷(MON4660,CAS71526-07-3)和2,2,5-三甲基-3-二氯乙酰基-1,3-唑烷(R-29148,CAS52836-31-4)。
b1)-b15)组活性化合物和安全剂C是已知的除草剂和安全剂,例如参见TheCompendiumofPesticideCommonNames(http://www.alanwood.net/pesticides/);B.Hock,C.Fedtke,R.R.Schmidt,Herbizide[除草剂],GeorgThiemeVerlag,Stuttgart,1995。其他除草活性化合物由WO96/26202,WO97/41116,WO97/41117,WO97/41118,WO01/83459和WO2008/074991以及W.等(编辑)“ModernCropProtectionCompounds”,第1卷,WileyVCH,2007及其中所引用的文献已知。
本发明还涉及配制成单组分组合物的作物保护组合物形式的组合物,该单组分组合物包含含有至少一种式I的苯并嗪酮类和至少一种其他活性化合物,优选选自b1-b15组的活性化合物的活性化合物组合,以及至少一种固体或液体载体和/或一种或多种表面活性剂以及需要的话一种或多种常用于作物保护组合物的其他助剂。
本发明还涉及配制成双组分组合物的作物保护组合物形式的组合物,该双组分组合物包含第一组分和第二组分,该第一组分包含至少一种式I的苯并嗪酮类、固体或液体载体和/或一种或多种表面活性剂,该第二组分包含至少一种选自b1-b15组活性化合物的其他活性化合物、固体或液体载体和/或一种或多种表面活性剂,其中这两种组分还可以额外地包含常用于作物保护组合物的其他助剂。
在包含至少一种式I化合物作为组分A和至少一种除草剂B的二元组合物中,活性化合物A∶B的重量比通常为1∶1000-1000∶1,优选1∶500-500∶1,尤其是1∶250-250∶1,特别优选1∶75-75∶1。
在包含至少一种式I化合物作为组分A和至少一种安全剂C的二元组合物中,活性化合物A∶C的重量比通常为1∶1000-1000∶1,优选1∶500-500∶1,尤其是1∶250-250∶1,特别优选1∶75-75∶1。
在包含至少一种式I化合物作为组分A、至少一种除草剂B和至少一种安全剂C的三元组合物中,组分A∶B的相对重量份通常为1∶1000-1000∶1,优选1∶500-500∶1,尤其是1∶250-250∶1,特别优选1∶75-75∶1;组分A∶C的重量比通常为1∶1000-1000∶1,优选1∶500-500∶1,尤其是1∶250-250∶1,特别优选1∶75-75∶1;以及组分B∶C的重量比通常为1∶1000-1000∶1,优选1∶500-500∶1,尤其是1∶250-250∶1,特别优选1∶75-75∶1。优选组分A+B与组分C的重量比为1∶500-500∶1,尤其是1∶250-250∶1,特别优选1∶75-75∶1。
特别优选的除草剂B是如上所定义的除草剂B;尤其是下表B所列除草剂B.1-B.144:
表B:
作为组分C构成本发明组合物的成分的特别优选安全剂C是如上所定义的安全剂C,尤其是下表C所列安全剂C.1-C.13:
表C
各组分在下面所述优选混合物中的重量比在上面所给限度内,尤其是优选限度内。
特别优选如下所述的组合物,其包含所定义的式I的苯并嗪酮类和如表1相应行所定义的物质;尤其优选包含所定义的式I的苯并嗪酮类作为唯一的除草活性化合物和如表1相应行所定义的物质;最优选包含所定义的式I的苯并嗪酮类作为唯一的活性化合物和如表1相应行所定义的物质。
特别优选组合物1.1-1.2029,其包含苯并嗪酮类Ia48和如表1相应行所定义的物质:
表1(组合物1.1-1.2029):
各单一组合物的特殊编号可按如下推导:
组合物1.777例如包含苯并嗪酮类Ia48、敌草隆(B.57)和解草唑(C.5)(见表1,第1.777项;以及表B,第B.57项和表C,第C.5项)。
组合物2.777例如包含苯并嗪酮类Im48(见下列组合物2.1-2.2029的定义)、敌草隆(B.57)和解草唑(C.5)(见表1,第1.777项;以及表B,第B.57项和表C,第C.5项)。
还尤其优选的是组合物2.1.-2.2029,它们与相应组合物1.1-1.2029的不同仅在于它们包含化合物Im48作为活性化合物A。
还尤其优选的是组合物3.1.-3.2029,它们与相应组合物1.1-1.2029的不同仅在于它们包含化合物In48作为活性化合物A。
还尤其优选的是组合物4.1.-4.2029,它们与相应组合物1.1-1.2029的不同仅在于它们包含化合物Io48作为活性化合物A。
还尤其优选的是组合物5.1.-5.2029,它们与相应组合物1.1-1.2029的不同仅在于它们包含化合物Ip48作为活性化合物A。
还尤其优选的是组合物6.1.-6.2029,它们与相应组合物1.1-1.2029的不同仅在于它们包含化合物Iq48作为活性化合物A。
还尤其优选的是组合物7.1.-7.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.31作为其他除草剂B。
还尤其优选的是组合物8.1.-8.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.32作为其他除草剂B。
还尤其优选的是组合物9.1.-9.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.33作为其他除草剂B。
还尤其优选的是组合物10.1.-10.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.40作为其他除草剂B。
还尤其优选的是组合物11.1.-11.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.44作为其他除草剂B。
还尤其优选的是组合物12.1.-12.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.45作为其他除草剂B。
还尤其优选的是组合物13.1.-13.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.52作为其他除草剂B。
还尤其优选的是组合物14.1.-14.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.53作为其他除草剂B。
还尤其优选的是组合物15.1.-15.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.54作为其他除草剂B。
还尤其优选的是组合物16.1.-16.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.55作为其他除草剂B。
还尤其优选的是组合物17.1.-17.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.56作为其他除草剂B。
还尤其优选的是组合物18.1.-18.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.57作为其他除草剂B。
还尤其优选的是组合物19.1.-19.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.60作为其他除草剂B。
还尤其优选的是组合物20.1.-20.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.65作为其他除草剂B。
还尤其优选的是组合物21.1.-21.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.66作为其他除草剂B。
还尤其优选的是组合物22.1.-22.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.69作为其他除草剂B。
还尤其优选的是组合物23.1.-23.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.72作为其他除草剂B。
还尤其优选的是组合物24.1.-24.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.73作为其他除草剂B。
还尤其优选的是组合物25.1.-25.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.76作为其他除草剂B。
还尤其优选的是组合物26.1.-26.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.77作为其他除草剂B。
还尤其优选的是组合物27.1.-27.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.83作为其他除草剂B。
还尤其优选的是组合物28.1.-28.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.84作为其他除草剂B。
还尤其优选的是组合物29.1.-29.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.87作为其他除草剂B。
还尤其优选的是组合物30.1.-30.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.87和B.54作为其他除草剂B。
还尤其优选的是组合物31.1.-31.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.87和B.60作为其他除草剂B。
还尤其优选的是组合物32.1.-32.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.87和B.66作为其他除草剂B。
还尤其优选的是组合物33.1.-33.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.88作为其他除草剂B。
还尤其优选的是组合物34.1.-34.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.88和B.54作为其他除草剂B。
还尤其优选的是组合物35.1.-35.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.88和B.60作为其他除草剂B。
还尤其优选的是组合物36.1.-36.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.88和B.66作为其他除草剂B。
还尤其优选的是组合物37.1.-37.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.90作为其他除草剂B。
还尤其优选的是组合物38.1.-38.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.91作为其他除草剂B。
还尤其优选的是组合物39.1.-39.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.91和B.54作为其他除草剂B。
还尤其优选的是组合物40.1.-40.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.91和B.60作为其他除草剂B。
还尤其优选的是组合物41.1.-41.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.91和B.66作为其他除草剂B。
还尤其优选的是组合物42.1.-42.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.93作为其他除草剂B。
还尤其优选的是组合物43.1.-43.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.94作为其他除草剂B。
还尤其优选的是组合物44.1.-44.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.94和B.54作为其他除草剂B。
还尤其优选的是组合物45.1.-45.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.94和B.60作为其他除草剂B。
还尤其优选的是组合物46.1.-46.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.94和B.66作为其他除草剂B。
还尤其优选的是组合物47.1.-47.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.98作为其他除草剂B。
还尤其优选的是组合物48.1.-48.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.98和B.54作为其他除草剂B。
还尤其优选的是组合物49.1.-49.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.98和B.76作为其他除草剂B。
还尤其优选的是组合物50.1.-50.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.98和B.87作为其他除草剂B。
还尤其优选的是组合物51.1.-51.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.98和B.106作为其他除草剂B。
还尤其优选的是组合物52.1.-52.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.98和B.88作为其他除草剂B。
还尤其优选的是组合物53.1.-53.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.98和B.91作为其他除草剂B。
还尤其优选的是组合物54.1.-54.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.98和B.94作为其他除草剂B。
还尤其优选的是组合物55.1.-55.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.101作为其他除草剂B。
还尤其优选的是组合物56.1.-56.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.104作为其他除草剂B。
还尤其优选的是组合物57.1.-57.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.106作为其他除草剂B。
还尤其优选的是组合物58.1.-58.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.109作为其他除草剂B。
还尤其优选的是组合物59.1.-59.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.110作为其他除草剂B。
还尤其优选的是组合物60.1.-60.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.111作为其他除草剂B。
还尤其优选的是组合物61.1.-61.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.113作为其他除草剂B。
还尤其优选的是组合物62.1.-62.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.115作为其他除草剂B。
还尤其优选的是组合物63.1.-63.2029,它们与相应组合物11.1-1.2029的不同仅在于它们额外包含B.116作为其他除草剂B。
还尤其优选的是组合物64.1.-64.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.120作为其他除草剂B。
还尤其优选的是组合物65.1.-65.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.122作为其他除草剂B。
还尤其优选的是组合物66.1.-66.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.123作为其他除草剂B。
还尤其优选的是组合物67.1.-67.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.125作为其他除草剂B。
还尤其优选的是组合物68.1.-68.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.126作为其他除草剂B。
还尤其优选的是组合物69.1.-69.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.133作为其他除草剂B。
还尤其优选的是组合物70.1.-70.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.2作为其他除草剂B。
还尤其优选的是组合物71.1.-71.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.7作为其他除草剂B。
还尤其优选的是组合物72.1.-72.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.29作为其他除草剂B。
还尤其优选的是组合物73.1.-73.2029,它们与相应组合物1.1-1.2029的不同仅在于它们额外包含B.30作为其他除草剂B。
下文通过实施例说明式I的苯并嗪酮类的制备;然而,本发明主题并不限于所给实施例。
实施例1:
2,2,7-三氟-6-(5-甲基-6-氧代-4-三氟甲基-6H-哒嗪-1-基)-4-丙-2-炔基-4H-苯并[1,4]嗪-3-酮(化合物Ia48)
实施例1.1:2-氨基-5-氟苯酚
在N2气氛下向在乙醇中的5-氟-2-硝基苯酚(26.63g,170mmol)中加入碳载钯(10重量%,250mg,0.235mmol)中。将该混合物用H2吹扫并在室温下在H2(气球)下搅拌,直到根据薄层色谱法(TLC)分析完全转化。通过过滤除去Pd/C并将滤液浓缩得到21.6g标题化合物。
1HNMR(DMSO):4.5(br,2H),6.35(dd,1H),6.45(dd,1H),6.50(dd,1H),9.5(br,1H)。
实施例1.2:2-溴-2,2-二氟-N-(4-氟-2-羟基苯基)乙酰胺
方案a)
在0℃下向无水四氢呋喃中的2-氨基-5-氟苯酚(14g,110mmol)中加入氢化钠(55重量%,在矿物油中;4.81g,110mmol)。将所得混合物在-15℃下搅拌15分钟。然后滴加2-溴-2,2-二氟乙酸乙酯(24.59g,121mmol)并将所得混合物在0℃下搅拌2小时。将反应混合物用饱和NH4Cl水溶液终止并用乙酸乙酯萃取。合并的萃取液用盐水洗涤,用Na2SO4干燥并浓缩而得到33g标题化合物。
1HNMR(DMSO):3.3(br,1H),6.8(m,2H),7.25(dd,1H),10.4(br,1H)。方案b)
在0℃下向无水四氢呋喃中的2-氨基-5-氟苯酚(200mg,1.573mmol)中加入氢化钠(55重量%,在矿物油中;68.6mg,1.573mmol)。将所得混合物在-15℃下搅拌15分钟。然后滴加2-溴-2,2-二氟乙酸甲酯(327mg,1.731mmol)并将所得混合物在0℃下搅拌2小时。将反应混合物在饱和NH4Cl水溶液中终止并用乙酸乙酯萃取。将合并的萃取液用盐水洗涤,用Na2SO4干燥并浓缩而得到450mg标题化合物。
1HNMR(DMSO):3.3(br,1H),6.8(m,2H),7.25(dd,1H),10.4(br,1H)。
实施例1.3:2,2,7-三氟-2H-苯并[b][1,4]嗪-3(4H)-酮
向无水甲苯中的2-溴-2,2-二氟-N-(4-氟-2-羟基苯基)乙酰胺(33g,116mmol)中加入1,8-二氮杂双环[5.4.0]十一碳-7-烯(DBU,17.51ml,116mmol)。将所得混合物在80℃下搅拌过夜。将该反应在饱和NH4Cl水溶液中终止并用乙酸乙酯萃取。将合并的萃取液用盐水洗涤,用Na2SO4干燥并浓缩而得到24.94g标题化合物。
GCMSm/e(M+)=203
实施例1.4:2,2,7-三氟-6-硝基-2H-苯并[b][1,4]嗪-3(4H)-酮
将2,2,7-三氟-2H-苯并[b][1,4]嗪-3(4H)-酮(2.5g,12.31mmol)溶于硫酸(40ml,750mmol)中。将反应混合物冷却至0-5℃。缓慢滴加硝酸(1.761ml,39.7mmol)并将温度维持为0-5℃。将反应混合物在该温度下搅拌30分钟。然后将反应混合物滴加到剧烈搅拌的冷水中。形成固体,将其用二氯甲烷提取。将合并的提取液在Na2SO4上干燥并浓缩而以褐色固体得到2.56g标题化合物。
GC/MSm/e(M+)=248
1H-NMR(CDCl3):2.90(br,1H),7.15(d,1H),7.80(d,1H)。
实施例1.5:2,2,7-三氟-6-硝基-4-(丙-2-炔基)-2H苯并[b][1,4]嗪-3(4H)-酮
在室温下向无水N,N-二甲基甲酰胺中的2,2,7-三氟-6-硝基-2H-苯并[b][1,4]嗪-3(4H)-酮(6.9g,27.8mmol)和碳酸钾(4.61g,33.4mmol)中滴加3-溴丙-1-炔(80重量%,在甲苯中;4.96g,33.4mmol)。将所得混合物在室温下搅拌过夜。将反应混合物倾入饱和NH4Cl水溶液中并用乙酸乙酯萃取。将合并的萃取液用NaCl水溶液洗涤,用Na2SO4干燥,浓缩并用甲苯捕集而以深褐色固体得到7.06g标题化合物。
GCMSm/e(M+)=286
实施例1.6:6-氨基-2,2,7-三氟-4-(丙-2-炔基)-2H苯并[b][1,4]嗪-3(4H)-酮
向在水中的氯化铵(3.96g,74.0mmol)中加入铁粉(325目;4.13g,74.0mmol)。向所得混合物中加入在甲醇/四氢呋喃中的2,2,7-三氟-6-硝基-4-(丙-2-炔基)-2H-苯并[b][1,4]嗪-3(4H)-酮(7.06g,24.67mmol)。在70℃下将所得混合物剧烈搅拌2小时。在搅拌下将该反应在水/乙酸乙酯中终止。将所得两相体系过滤并分离各层。随后将水层用乙酸乙酯萃取。将合并的有机相用盐水洗涤,用Na2SO4干燥并浓缩而得到5.15g标题化合物。
GCMSm/e(M+)=256
实施例1.7:2,2,7-三氟-6-肼基-4-丙-2-炔基-4H-苯并[1,4]嗪-3-酮
在-5℃下在30分钟内向6-氨基-2,2,7-三氟-4-(丙-2-炔基)-2H-苯并[b][1,4]嗪-3(4H)-酮(20g,78mmol)在浓盐酸(100ml,1218mmol)中的机械搅拌悬浮液中滴加亚硝酸钠(5.82g,84mmol)在水(40ml)中的溶液,维持温度在-5℃以下。将所得混合物在~0℃下搅拌1小时。然后将搅拌的反应混合物用干冰/2-丙醇冷却浴冷却至-35℃。在约1分钟内加入氯化锡(II)(37.0g,195mmol)在浓盐酸(40ml,487mmol)中的冷却溶液(-10℃),在此期间温度由-35℃升至-10℃。将所得混合物在0℃下搅拌1小时。然后将80g硅藻土加入反应混合物中并通过在搅拌下缓慢加入10%NaOH水溶液而将所得混合物中和至pH~7。过滤整个物料并将滤饼和滤液用乙醚萃取2次。将萃取液用盐水洗涤,在Na2SO4上干燥并真空浓缩,得到17g纯度为约85%的产物。用二异丙基醚研碎而得到11.87g产物。通过浓缩母液得到另外3.6g产物。
1HNMR(DMSO-d4)δ7.29-7.26(m,2H),4.80-4.79(d,2H),4.16(s,2H),3.45-3.44(t,1H)。
实施例1.8:(E)-2,2,7-三氟-4-丙-2-炔基-6-{N′-[3,3,3-三氟-2-氧代-(Z)-亚丙基]肼基}-4H-苯并[1,4]嗪-3-酮
在冰冷却和氮气气氛下向乙酸钠(0.865g,10.55mmol)在水(10ml)中的搅拌溶液中加入3,3-二溴-1,1,1-三氟丙-2-酮(1.294g,4.79mmol)。然后使该反应在80℃下进行1小时。然后将反应混合物冷却至0℃并一次加入2,2,7-三氟-6-肼基-4-(丙-2-炔基)-2H-苯并[b][1,4]嗪-3(4H)-酮(1g,3.69mmol)。反应混合物由白/米色悬浮液变成硬黄色悬浮液。该反应液在室温下继续2小时并将所得沉淀在玻璃过滤器上收集。产物(黄色粉末)用水和庚烷洗涤并在过滤器上干燥。其不经进一步提纯而用于下一步中。
实施例1.9:2,2,7-三氟-6-(5-甲基-6-氧代-4-三氟甲基-6H-哒嗪-1-基)-4-丙-2-炔基-4H-苯并[1,4]嗪-3-酮
向(E)-2,2,7-三氟-4-(丙-2-炔基)-6-(2-(3,3,3-三氟-2-氧代亚丙基)肼基)-2H-苯并[b][1,4]嗪-3-酮(1399mg,3.69mmol)在无水甲苯(20ml)中的搅拌黄色悬浮液中加入(乙氧甲酰基亚乙基)三苯基正膦(1738mg,4.80mmol),得到透明的橙/红色溶液。该反应在回流和Dean-Stark条件下继续过夜,同时进行共沸脱水。然后真空浓缩反应混合物而得到含有约50%三苯基膦氧化物的2.99g粗产物。粗产物在二氧化硅上层析(9∶1->1∶1庚烷/乙酸乙酯),得到1.08g产物(约89%纯度)。由二异丙基醚/庚烷重结晶而以白色粉末得到标题化合物(纯度>99%)。
1HNMR(DMSO-d6)δ8.37(s,1H),7.82-7.78(m,2H),4.82(d,2H),3.47-3.46(t,1H),2.33(2,3H)。
实施例2:(6S,7aR)-6-氟-2-(2,2,7-三氟-3-氧代-4-丙-2-炔基-3,4--二氢-2H-苯并[1,4]嗪-6-基)-四氢吡咯并[1,2-c]咪唑-1,3-二酮
实施例2.1:(1S,4R)-4-氟-2-(2,2,7-三氟-3-氧代-4-丙-2-炔基-3,4-二氢-2H-苯并[1,4]嗪-6-基氨基甲酰基)环戊烷甲酸
在室温和氮气下将羰基二咪唑(1519mg,9.37mmol)加入6-氨基-2,2,7-三氟-4-(丙-2-炔基)-2H-苯并[b][1,4]嗪-3(4H)-酮(上面步骤1.6的产物,800mg,3.12mmol)和三乙胺(0.457ml,3.28mmol)在无水乙腈(15ml)中的搅拌溶液中。将所得混合物加热至80℃。然后加入(2R,4S)-4-氟吡咯烷-2-甲酸(416mg,3.12mmol)。将所得悬浮液在回流下搅拌。2小时后得到红/褐色透明溶液。LCMS分析表明已经发生完全转化。将反应混合物逐渐冷却至室温,倾入1N盐酸中并用乙酸乙酯萃取3次。将合并的有机萃取液用盐水洗涤,在无水硫酸钠上干燥并真空蒸发而得到所需化合物(1.34g,纯度约90%),其不经进一步提纯而用于下一步中。
实施例2.2:(6S,7aR)-6-氟-2-(2,2,7-三氟-3-氧代-4-丙-2-炔基-3,4-二氢-2H-苯并[1,4]嗪-6-基)-四氢吡咯并[1,2-c]咪唑-1,3-二酮
在氮气和70℃下将(1S,4R)-4-氟-2-(2,2,7-三氟-3-氧代-4-丙-2-炔基-3,4-二氢-2H-苯并[1,4]嗪-6-基氨基甲酰基)环戊烷甲酸(1.296g,3.12mmol)和盐酸(1.56ml4N二烷溶液,6.24mmol)在二烷(25ml)中的混合物搅拌2小时,然后进一步搅拌过夜,此时LCMS分析表明完全转化。将反应混合物冷却至室温并真空蒸发而得到约1.3g粗产物。将其用二异丙基醚研碎并由二氯甲烷和正庚烷的混合物结晶。固体残余物的柱层析(9∶1->1∶1,正庚烷/乙酸乙酯)得到868mg标题化合物(纯度>95%)。
1HNMR(CDCl3)δ7.25-7.23(d,1H),7.17-7.15(d,1H),5.60-5.47(d,1H,J=52),4.83-4.72(q,2H),4.67-4.63(q,1H),4.17(m,1H),3.70-3.60(q,4H),2.78-2.69(m,1H),2.40-2.39(t,1H),2.07-1.90(m,1H)。
实施例3:2,2,7-三氟-6-(3-氧代-5,6,7,8-四氢-[1,2,4]三唑并[4,3-a]吡啶-2-基-4-丙-2-炔基-4H-苯并[1,4]嗪-3-酮(化合物Ic48)
实施例3.1:甲酸N′-(2,2,7-三氟-3-氧代-4-丙-2-炔基-3,4-二氢-2H-苯并[1,4]嗪-6-基)酰肼
在室温和搅拌下将甲酸(0.157ml,4.09mmol)加入在二氯甲烷中的2,2,7-三氟-6-肼基-4-(丙-2-炔基)-2H-苯并[b][1,4]嗪-3(4H)-酮(上面步骤1.7的产物,1.0g,3.69mmol)中。然后将该混合物在室温下搅拌过夜。将所得沉淀在玻璃过滤器上分离并用二异丙基醚洗涤,得到858mg产物(纯度>95%),其不经进一步提纯而使用。
实施例3.2:6-氯-3,4-二氢吡啶-1(2H)-甲酰氯
在~-20℃(用干冰/2-丙醇浴冷却)和氮气下向搅拌的双光气(3.10ml,25.7mmol)中加入活性炭(0.25g),这使得一些光气气体释放。在1小时内向所得搅拌混合物中非常缓慢地滴加在乙酸乙酯(在分子筛上干燥)(7ml)中的哌啶-2-酮(2.55g,25.7mmol),同时保持温度在0℃以下。然后将该反应液在室温下搅拌2小时,此时根据TLC分析发现该反应完全。过滤反应混合物以除去沉淀和活性炭,然后用无水乙酸乙酯洗涤。将滤液真空浓缩(用氩气吹扫)而以黄色浑浊油得到1.87g产物,其没有进一步提纯而用于下一步中。
实施例3.3:2,2,7-三氟-6-(3-氧代-5,6,7,8-四氢-[1,2,4]三唑并[4,3-a]吡啶-2-基-4-丙-2-炔基-4H-苯并[1,4]嗪-3-酮
向N′-(2,2,7-三氟-3-氧代-4-(丙-2-炔基)-3,4-二氢-2H-苯并[b][1,4]嗪-6-基)甲酰肼(850mg,2.84mmol)在无水乙腈(35ml)中的冰浴冷却的黄/褐色悬浮液中滴加在无水乙腈(1ml)中的6-氯-3,4-二氢吡啶-1(2H)-甲酰氯(614mg,3.41mmol),维持温度在10℃以下。然后滴加三乙胺(0.792ml,5.68mmol)并在~10℃下继续搅拌1小时,得到透明红色溶液。然后将该反应液在50℃下搅拌2小时,此时TLC分析表明反应完全。滴加6N盐酸(4.26ml,25.6mmol)并将所得混合物在50℃下搅拌1小时。然后将反应混合物倾入~250ml水中并将整个物料用乙酸乙酯萃取3次。合并的有机层用盐水洗涤并在Na2SO4上干燥。然后真空浓缩有机相而得到950mg粗产物。层析(2∶1->1∶9己烷/乙酸乙酯)得到550mg产物(92%纯度)。用二异丙基醚研碎得到440mg标题化合物(纯度>95%)。
1HNMR(CDCl3)δ7.52-7.50(d,1H),7.15-7.13(d,1H),4.79-4.78(d,2H),3.74-3.71(t,2H),2.81-2.78(t,2H),2.37-2.36(t,1H),2.04-1.95(m,4H)
实施例4:5-异亚丙基-3-(2,2,7-三氟-3-氧代-4-丙-2-炔基-3,4-二氢-2H-苯并[1,4]嗪-6-基)唑烷-2,4-二酮(化合物Ie48)
实施例4.1:3,3-二甲基环氧乙烷-2-甲酸乙酯
在-10℃和氮气下向丙烷-2-酮(11.52ml,157mmol)和2-氯乙酸乙酯(25.04ml,235mmol)在无水乙醚(125ml)中的搅拌溶液中分批加入乙醇钠(10.66g,157mmol),保持温度在5℃以下。加料完成之后将该混合物在-10℃下搅拌2小时,然后将该反应在室温下继续3小时。将反应混合物用饱和氯化铵水溶液终止,分离各相并将水层用乙醚(100ml)萃取。合并的有机相在Na2SO4上干燥并真空蒸发。将所得残余物通过真空蒸馏提纯。主馏分(-25毫巴,82-85℃,14.3g)由含有6.4mol%氯乙酸乙酯的所需产物构成。这不经进一步提纯而用于下一步中。
1HNMR(CDCl3)δ4.32-4.20(m,2H),1.43-1.39(d,6H),1.33-1.30(t,3H)。
实施例4.2:2-羟基-3-甲基丁-3-烯酸乙酯
通过在用氮气吹扫的旋转蒸发器中用苯(3×10ml)共沸蒸馏而使一水合对甲苯磺酸(0.132g,0.694mmol)脱水。然后加入苯(100ml)和3,3-二甲基环氧乙烷-2-甲酸乙酯(1g,6.94mmol)并将所得混合物在回流(81℃)下搅拌过夜。然后将透明的反应混合物冷却至室温,冷却至4℃并保持数小时,然后在玻璃过滤器上过滤以除去结晶的对甲苯磺酸。将滤液真空浓缩(40℃,50毫巴)而得到778mg粗产物(含2.5重量%苯),其不经进一步提纯而用于下一步中。
1HNMR(CDCl3)δ5.14(d,1H),5.04(s,1H),4.56(s,1H),4.30-4.24(q,2H),2.51(br.s,1H),1.75(s,3H),1.32-1.29(t,3H)
实施例4.3:5-异亚丙基-3-(2,2,7-三氟-3-氧代-4-丙-2-炔基-3,4-二氢-2H-苯并[1,4]嗪-6-基)唑烷-2,4-二酮
在氮气下向6-氨基-2,2,7-三氟-4-(丙-2-炔基)-2H-苯并[b][1,4]嗪-3(4H)-酮(上面步骤1.6的产物,810mg,3.16mmol)和三乙胺(0.463ml,3.32mmol)在无水乙腈(20ml)中的搅拌溶液中加入羰基二咪唑(1026mg,6.33mmol)。将所得混合物加热至60℃。然后加入在1ml无水乙腈中的2-羟基-3-甲基丁-3-烯酸乙酯(456mg,3.16mmol)。将该反应液加热至回流并由LCMS监测该反应直到所有原料消耗掉。然后将反应混合物用乙酸乙酯稀释并用1N盐酸洗涤。水相用乙酸乙酯萃取两次,合并的有机相用盐水洗涤,在Na2SO4上干燥并真空浓缩而得到1.34g粗产物。柱层析(二氧化硅,9∶1->2∶1,己烷/乙酸乙酯)得到573mg含有24%氨基甲酸乙酯产物的产物。由二氯甲烷/正庚烷重结晶而得到322mg标题化合物(纯度>95%)。1HNMR(CDCl3)δ7.30-7.28(d,1H),7.21-7.18(d,1H),4.79-4.78(d,2H),2.40-2.39(t,1H),2.32(s,3H),2.09(s,3H)。
实施例5:7-氟-6-[3-氧代-四氢-[1,3,4]噻二唑并[3,4-a]哒嗪-(1Z)-亚基氨基]-4-丙-2-炔基-4H-苯并[1,4]嗪-3-酮(化合物If48)
实施例5.1:2,2,7-三氟-6-异硫氰酸酯基-4-(丙-2-炔基)-2H-苯并[b][1,4]嗪-3(4H)-酮
在0℃和氮气下将碳酸氢钠(4.10g,48.8mmol)加入6-氨基-2,2,7-三氟-4-(丙-2-炔基)-2H-苯并[b][1,4]嗪-3(4H)-酮(上面步骤1.6的产物,5.0g,19.52mmol)在无水乙醇(100ml)中的搅拌溶液中。然后在冰浴冷却下滴加硫光气(1.795ml,23.42mmol),保持反应混合物的温度在10℃以下,在加料完成后将反应混合物在室温下搅拌1小时,此时根据TLC分析该反应完全。通过过滤取出该盐并用乙酸乙酯洗涤。真空浓缩滤液,得到6.55g含有约30%氨基甲酸乙酯的粗产物。由二氯甲烷重结晶得到3.84g所需产物(>90%纯度),其不经进一步提纯而使用。
实施例5.2:哌嗪-1,2-二氯化物
在0℃和氮气下将肼-1,2-二甲酸二叔丁基酯(10g,43.1mmol)在无水N,N-二甲基甲酰胺(25ml)中的溶液加入氢化钠(3.79g在矿物油中的60%悬浮液,95mmol)在无水N,N-二甲基甲酰胺(175ml)中的搅拌悬浮液中。将反应混合物搅拌30分钟,然后在半分钟内加入1,4-二溴丁烷(9.3g,43.1mmol)。将该反应液在室温下搅拌过夜。然后在室温下将水(~20ml)小心加入反应混合物中,并继续搅拌约5分钟。然后将终止的反应混合物倾入1升水中。将该产物用乙醚(200ml)萃取2次,合并的有机层用10%氯化钠水溶液洗涤3次,在无水硫酸钠上干燥,并真空浓缩而得到14g粗四氢哒嗪-1,2-二甲酸二叔丁基酯。将这溶于乙醚(200ml)中并加入在二烷中的4N盐酸(108ml,431mmol)。将所得混合物在室温下搅拌过夜。将如此形成的白色沉淀通过过滤分离并在氮气流下干燥而得到4.6g粗产物。1HNMR分析表明该反应尚未完成。将粗产物与类似制备的粗产物合并,溶于二氯甲烷(200ml)中,用在二烷中的4N盐酸(60ml,240mmol)处理并将所得混合物在室温下搅拌过夜。将反应混合物真空浓缩并用无水乙醚研碎。将所得沉淀通过过滤分离并在氮气流下干燥而得到6.3g产物,其不经进一步提纯而用于下一步中。
1HNMR(DMSO-d4)δ8.85(宽s,4H),3.00(s,4H),1.69(s,4H)
实施例5.3:7-氟-6-[3-氧代四氢-[1,3,4]噻二唑并[3,4-a]哒嗪-(1Z)-亚基氨基]-4-丙-2-炔基-4H-苯并[1,4]嗪-3-酮(化合物1f48)
在室温和氮气下将三乙胺(1.402ml,10.06mmol)加入哌嗪-1,2-二氯化物(0.587g,3.69mmol)在二氯甲烷(5ml)中的搅拌悬浮液中。这得到浓稠且几乎不可搅拌的白色悬浮液。向其中滴加在二氯甲烷(5ml)中的2,2,7-三氟-6-异硫氰酸酯基-4-(丙-2-炔基)-2H-苯并[b][1,4]嗪-3(4H)-酮(上面步骤4.1的产物,1g,3.35mmol)。将所得混合物在室温下搅拌1小时,此时TLC分析表明反应完全。将反应混合物真空浓缩,得到粗产物。然后将其用水研碎以除去盐。将如此形成的沉淀通过过滤分离,用水洗涤并干燥而以白色粉末得到1.19g标题化合物(纯度>95%)。
1HNMR(DMSO-d4)δ10.03(s,1H),7.92-7.90(d,1H),7.55-7.52(d,1H),5.37-5.34(t,1H),4.78(s,2H),4.15(broads,2H),3.45(s,1H),2.88-2.87(d,2H),1.68-1.61(m,4H)MS(m/z),M+H:411.0
实施例6:6-(5-叔丁基-2-氧代-[1,3,4]二唑-3-基)-2,2,7-三氟-4-丙-2-炔基-4H-苯并[1,4]嗪-3-酮(化合物1g48)
实施例6.1:2,2-二甲基丙酸N′-(2,2,7-三氟-3-氧代-4-丙-2-炔基-3,4-二氢-2H-苯并[1,4]嗪-6-基)酰肼
在室温和氮气下将新戊酸酐(0.687g,3.69mmol)滴加到2,2,7-三氟-6-肼基-4-(丙-2-炔基)-2H-苯并[b][1,4]嗪-3(4H)-酮(上面步骤1.7的产物,1.0g,3.69mmol)在二氯甲烷中的搅拌溶液中。将所得混合物在室温下搅拌1小时,此时TLC分析表明反应完全。将反应混合物用二氯甲烷稀释并用1N盐酸水溶液洗涤。水层用二氯甲烷萃取,将合并的有机相在无水硫酸钠上干燥并真空蒸发而得到1.55g粗产物,其不经进一步提纯而用于下一步中。
实施例6.2:6-(5-叔丁基-2-氧代-[1,3,4]二唑-3-基)-2,2,7-三氟-4-丙-2-炔基-4H-苯并[1,4]嗪-3-酮
在室温和氮气下将双光气(0.445ml,3.69mmol)滴加到N′-(2,2,7-三氟-3-氧代-4-(丙-2-炔基)-3,4-二氢-2H-苯并[b][1,4]嗪-6-基)新戊酰肼(1311mg,3.69mmol)在无水甲苯(30ml)中的搅拌溶液中。将所得混合物在回流下搅拌4小时。然后冷却至室温并真空蒸发,得到1.7g粗产物。用二异丙基醚将其研碎而以白色粉末得到990mg标题化合物(纯度>95%)。
1HNMR(DMSO-d6)δ7.83-7.80(m,2H),4.83(d,2H),3.50(s,1H),1.32(s,9H)。
实施例7:1-丙基-2-硫代-3-(2,2,7-三氟-3-氧代-4-丙-2-炔基-3,4-二氢-2H-苯并[1,4]嗪-6-基)咪唑烷-4,5-二酮(化合物Ii48)
实施例7.1:1-丙基-3-(2,2,7-三氟-3-氧代-4-丙-2-炔基-3,4-二氢-2H-苯并[1,4]嗪-6-基)硫脲
在室温和氮气下将丙烷-1-胺(0.937ml,11.74mmol)加入2,2,7-三氟-6-异硫氰酸酯基-4-(丙-2-炔基)-2H-苯并[b][1,4]嗪-3(4H)-酮(上面步骤4.1的产物,1.0g,3.35mmol)在二氯甲烷(10ml)中的搅拌溶液中。将所得混合物在室温下搅拌1小时,此时TLC分析表明该反应完全。将反应混合物真空蒸发,得到1.3g所需产物(纯度>95%),其不经进一步提纯而用于下一步中。
实施例7.2:1-丙基-2-硫代-3-(2,2,7-三氟-3-氧代-4-丙-2-炔基-3,4-二氢-2H-苯并[1,4]嗪-6-基)咪唑烷-4,5-二酮
在室温和氮气下将乙基草酰氯(0.487ml,4.36mmol)加入1-丙基-3-(2,2,7-三氟-3-氧代-4-(丙-2-炔基)-3,4-二氢-2H-苯并[b][1,4]嗪-6-基)硫脲(1197mg,3.35mmol)在二氯甲烷(20ml)中的搅拌溶液中。将所得混合物在室温下搅拌过夜,然后真空蒸发。将甲苯加入黄色残余物中并将所得悬浮液回流3小时,得到透明溶液。将反应混合物冷却至室温,将所得沉淀分离并用庚烷洗涤,得到792mg粗产物。然后将其由甲苯重结晶。一些残留杂质通过将该固体溶于乙酸乙酯中而除去,用碳酸氢钠水溶液洗涤,在硫酸钠上干燥并真空蒸发,得到667mg标题化合物(纯度>95%)。
1HNMR(DMSO-d6)δ7.83-7.80(d,1H),7.66-7.64(d,1H),4.77-4.67(d,2H),3.91-3.80(t,2H),3.52-3.51(t,1H),1.75-1.66(m,2H),0.97-0.93(t,3H)。
实施例8:1-甲基-3-(2,2,7-三氟-3-氧代-4-丙-2-炔基-3,4-二氢-2H-苯并[1,4]嗪-6-基)-1H-喹唑啉-2,4-二酮(化合物Ik48)
在室温和氮气下将羰基二咪唑(1.266g,7.81mmol)加入6-氨基-2,2,7-三氟-4-(丙-2-炔基)-2H-苯并[b][1,4]嗪-3(4H)-酮(上面步骤1.6的产物,1.0g,3.90mmol)和三乙胺(0.571ml,4.10mmol)在无水乙腈(20ml)中的搅拌溶液中。将所得混合物加热至60℃,然后加入2-(甲基氨基)苯甲酸甲酯(0.602ml,4.10mmol)。将该反应液加热至回流并保持1小时,此时用苄基胺终止并随后进行含水酸性后处理的少量样品的LCMS分析表明反应完全。然后将反应混合物倾入乙酸乙酯(100ml)和1N盐酸水溶液(100ml)的搅拌混合物中。分离各相并将水相用乙酸乙酯萃取。合并的有机相用盐水洗涤,在无水硫酸钠上干燥并真空蒸发,得到1.69g粗产物。将其用二氯甲烷研碎过夜,将所得沉淀滤出,用二异丙醚洗涤并在无水硫酸钠上干燥而以灰白色粉末得到860mg标题化合物。
1HNMR(CDCl3)δ8.11-8.09(d,1H),7.91-7.88(t,1H),7.78-7.77(t,1H),7.75(s,1H),7.59(d,1H),7.41-7.37(t,1H),4.80-4.71(d,2H),3.58(s,3H),3.45(s,1H))。
除了上述化合物外按照上述方法制备其他式I的苯并嗪酮类,其列于下表2中:
应用实施例
式I的苯并嗪酮类的除草活性由下列温室试验证实:
所用培养容器为含有含约3.0%腐殖土的壤质砂作为底物的塑料花盆。对每一品种单独播种测试植物的种子。
对于出苗前处理,直接在播种之后借助细分布喷嘴施用悬浮或乳化于水中的活性成分。温和灌溉容器以促进发芽和生长,然后用透明塑料罩覆盖,直到植物生根。该覆盖导致测试植物均匀发芽,除非被活性成分损坏。
对于出苗后处理,首先使测试植物生长到3-15cm的高度,这取决于植物习性,仅在此时用悬浮或乳化于水中的活性成分处理。为此,将测试植物直接播种并在相同容器中生长,或者首先使它们作为秧苗单独生长并在处理之前几天移植到测试容器中。
取决于品种,将植物保持在10-25℃或20-35℃。测试期为2-4周。在此期间照料植物并评价它们对各处理的响应。
使用0-100的评分进行评价。100表示没有植物出苗,或者至少地面上部分完全受损,而0表示没有损害,或者生长过程正常。对良好的除草活性给予至少70的分值,而对非常好的除草活性给予至少85的分值。
用于温室试验中的植物属于下列品种:
Bayer代码 | 学名 |
ABUTH | 苘麻(Abutilon theophrasti) |
AMAPA | 长芒苋(Amaranthus palmeri) |
AMARE | 马齿苋(Amaranthus retroflexus) |
CHEAL | 藜(Chenopodium album) |
KCHSC | 扫帚菜(Kochia scoparia) |
MALNE | 圆叶锦葵(Malva neglecta) |
VIOAR | 堇菜(Viola arvensis) |
在12.5g/ha的施用率下,通过出苗后方法施用的化合物Ia48对长芒苋、扫帚菜和圆叶锦葵显示出非常好的除草活性。
在25g/ha的施用率下,通过出苗前方法施用的化合物Ia48对马齿苋和堇菜显示出非常好的除草活性。
在12.5g/ha的施用率下,通过出苗后方法施用的化合物Ig48对长芒苋和圆叶锦葵显示出非常好的除草活性且对扫帚菜显示出良好的除草活性。
在25g/ha的施用率下,通过出苗前方法施用的化合物Ig48对马齿苋和堇菜显示出非常好的除草活性。
在12.5g/ha的施用率下,通过出苗后方法施用的化合物Ii48对扫帚菜和圆叶锦葵显示出非常好的除草活性。
在12.5g/ha的施用率下,通过出苗后方法施用的化合物Ik48对长芒苋、扫帚菜和圆叶锦葵显示出非常好的除草活性。
在25g/ha的施用率下,通过出苗前方法施用的化合物Ik48对马齿苋显示出非常好的除草活性且对堇菜显示出良好的除草活性。
在50g/ha的施用率下,通过出苗前方法施用的化合物If48对苘麻、马齿苋和藜显示出非常好的除草活性。
在50g/ha的施用率下,通过出苗前方法施用的实施例2对苘麻、马齿苋和藜显示出非常好的除草活性。
在50g/ha的施用率下,通过出苗前方法施用的实施例9对苘麻、马齿苋和藜显示出非常好的除草活性。
在50g/ha的施用率下,通过出苗前方法施用的实施例10对苘麻、马齿苋和藜显示出非常好的除草活性。
在50g/ha的施用率下,通过出苗前方法施用的实施例11对苘麻、马齿苋和藜显示出非常好的除草活性。
在50g/ha的施用率下,通过出苗前方法施用的实施例12对苘麻、马齿苋和藜显示出非常好的除草活性。
在50g/ha的施用率下,通过出苗前方法施用的实施例13对马齿苋和藜显示出非常好的除草活性。
在50g/ha的施用率下,通过出苗前方法施用的实施例14对苘麻、马齿苋和藜显示出非常好的除草活性。
在50g/ha的施用率下,通过出苗前方法施用的实施例15对马齿苋和藜显示出非常好的除草活性。
在50g/ha的施用率下,通过出苗前方法施用的实施例16对马齿苋和藜显示出非常好的除草活性。
在50g/ha的施用率下,通过出苗前方法施用的实施例17对马齿苋和藜显示出非常好的除草活性。
在1000g/ha的施用率下,通过出苗后方法施用的实施例19对苘麻显示出非常好的除草活性。
Claims (10)
1.式I的苯并嗪酮类化合物:
其中
R1为氢或卤素;
R2为氢、C1-C6烷基、C1-C6卤代烷基、C3-C6环烷基、C3-C6链烯基、C3-C6卤代链烯基、C3-C6炔基、C3-C6卤代炔基、C1-C6烷氧基或C3-C6环烷基-C1-C6烷基;
R3为卤素;
R4为卤素;
X为O或S;以及
Y选自Y2、Y12、Y13、Y20、Y31、Y37、Y38、Y39、Y42和Y55的取代基:
其中
A1、A4、A5、A6和A7为氧或硫;
A11为氧、硫、SO或SO2;
Al2和A15为氧或硫;
R37、R38、R39、R43和R44为氢、羟基、C1-C6烷基、C1-C6卤代烷基、C3-C7环烷基、C3-C7环烷氧基、C1-C6烷氧基、C1-C6卤代烷氧基、C2-C6链烯基、C2-C6卤代链烯基、C2-C6链烯氧基、C3-C6炔基、C3-C6炔氧基、C1-C6烷硫基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6烷氧基磺酰基、C1-C6烷基磺酰氧基、氨基、C1-C6烷基氨基或二(C1-C6烷基)氨基;
R9、R10、R11、R12、R20、R21、R25、R26、R33和R34为氢、氰基、羟基、C1-C6烷基、C1-C6氰基烷基、C1-C6卤代烷基、C3-C7环烷基、C3-C7环烷氧基、C1-C6烷氧基、C1-C6卤代烷氧基、C2-C6链烯基、C2-C6卤代链烯基、C2-C6链烯氧基、C3-C6炔基、C3-C6炔氧基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、苯基-C1-C6烷基、氨基、C1-C6烷基氨基或二(C1-C6烷基)氨基;或者
R11和R12、R25和R26或者R33和R34与它们所连接的原子一起形成饱和、部分不饱和或芳族3-6员环,该环除了碳原子外可以包含1-4个氮原子,或者1或2个氧原子,或者1或2个硫原子,或者1-3个氮原子和1个氧原子,或者1-3个氮原子和1个硫原子,或者1个硫和1个氧原子,并且其本身可以部分或完全被卤代和/或被1-3个选自C1-C6烷基和C1-C6烷氧基的基团取代;
R14和R15为氢、卤素或C1-C6烷基;
R19、R35、R36和R42为氢、卤素、羟基、C1-C6烷基、C1-C6卤代烷基、C3-C7环烷基、C3-C7环烷氧基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6卤代烷硫基、C2-C6链烯基、C2-C6卤代链烯基、C2-C6链烯氧基、C3-C6炔基或C3-C6炔氧基;以及
其中当Y为Y2或Y20时,R3和R4均为卤素;
及其可农用盐。
2.如权利要求1所要求的式I的苯并嗪酮类化合物及其可农用盐,其中R1为卤素。
3.如权利要求1或2所要求的式I的苯并嗪酮类化合物及其可农用盐,其中R2为C3-C6炔基或C3-C6卤代炔基。
4.如权利要求1或2所要求的式I的苯并嗪酮类化合物及其可农用盐,其中Y为Y2、Y42或Y55。
5.如权利要求3所要求的式I的苯并嗪酮类化合物及其可农用盐,其中Y为Y2、Y42或Y55。
6.一种除草组合物,包含除草活性量的至少一种如权利要求1-5中任一项所要求的式I的苯并嗪酮类化合物及其可农用盐和至少一种选自除草剂B和/或安全剂C的其他活性化合物。
7.根据权利要求6的组合物,其包含至少两种选自除草剂B和/或安全剂C的其他活性化合物。
8.一种除草组合物,包含除草活性量的至少一种如权利要求1-5中任一项所要求的式I的苯并嗪酮类化合物及其可农用盐或如权利要求6或7所要求的除草组合物和至少一种惰性液体和/或固体载体以及合适的话至少一种表面活性物质。
9.一种制备除草活性组合物的方法,包括使除草活性量的至少一种如权利要求1-5中任一项所要求的式I的苯并嗪酮类化合物及其可农用盐或如权利要求6或7所要求的除草组合物与至少一种惰性液体和/或固体载体以及需要的话至少一种表面活性物质混合。
10.一种防治不希望的植物生长的方法,包括使除草活性量的至少一种如权利要求1-5中任一项所要求的式I的苯并嗪酮类化合物及其可农用盐或如权利要求6、7或8所要求的除草组合物作用于植物、其环境或种子上。
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BR112013007610A8 (pt) | 2018-02-14 |
US20130184155A1 (en) | 2013-07-18 |
EP2621924B1 (en) | 2015-03-04 |
CN103221409A (zh) | 2013-07-24 |
BR112013007610A2 (pt) | 2016-07-26 |
JP2013540113A (ja) | 2013-10-31 |
EP2621924A1 (en) | 2013-08-07 |
US8669208B2 (en) | 2014-03-11 |
WO2012041789A1 (en) | 2012-04-05 |
BR112013007610B1 (pt) | 2018-03-20 |
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