CN113423693B - 除草化合物 - Google Patents
除草化合物 Download PDFInfo
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- CN113423693B CN113423693B CN202080013887.1A CN202080013887A CN113423693B CN 113423693 B CN113423693 B CN 113423693B CN 202080013887 A CN202080013887 A CN 202080013887A CN 113423693 B CN113423693 B CN 113423693B
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- alkyl
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 110
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 21
- 239000000203 mixture Substances 0.000 claims abstract description 62
- 241000196324 Embryophyta Species 0.000 claims abstract description 28
- -1 -CH 2 CN Chemical group 0.000 claims description 75
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- 238000009472 formulation Methods 0.000 claims description 13
- 239000004009 herbicide Substances 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 11
- 239000000575 pesticide Substances 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 239000002671 adjuvant Substances 0.000 claims description 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 3
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 claims description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 1
- 244000045561 useful plants Species 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 239000002904 solvent Substances 0.000 description 19
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 14
- 239000007787 solid Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- 239000004094 surface-active agent Substances 0.000 description 13
- 238000003786 synthesis reaction Methods 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000000843 powder Substances 0.000 description 12
- 239000000543 intermediate Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- COYBRKAVBMYYSF-UHFFFAOYSA-N heptan-2-yl [(5-chloroquinolin-8-yl)oxy]acetate Chemical group C1=CN=C2C(OCC(=O)OC(C)CCCCC)=CC=C(Cl)C2=C1 COYBRKAVBMYYSF-UHFFFAOYSA-N 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- 239000005499 Clomazone Substances 0.000 description 8
- KIEDNEWSYUYDSN-UHFFFAOYSA-N clomazone Chemical compound O=C1C(C)(C)CON1CC1=CC=CC=C1Cl KIEDNEWSYUYDSN-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000008187 granular material Substances 0.000 description 8
- 239000004530 micro-emulsion Substances 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 240000008042 Zea mays Species 0.000 description 7
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 244000038559 crop plants Species 0.000 description 7
- 239000004495 emulsifiable concentrate Substances 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 229910052763 palladium Inorganic materials 0.000 description 7
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 6
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical group [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000005859 coupling reaction Methods 0.000 description 6
- 125000004093 cyano group Chemical group *C#N 0.000 description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- 239000003112 inhibitor Substances 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 239000000080 wetting agent Substances 0.000 description 6
- GMYVTYJFOXIMSJ-UHFFFAOYSA-N 9-(2,6-dimethyl-4-prop-1-ynylphenyl)-3-(2-oxopropanoyl)-3-azaspiro[5.5]undecane-8,10-dione Chemical compound CC1=C(C(=CC(=C1)C#CC)C)C1C(CC2(CCN(CC2)C(C(C)=O)=O)CC1=O)=O GMYVTYJFOXIMSJ-UHFFFAOYSA-N 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 239000002270 dispersing agent Substances 0.000 description 5
- 238000003818 flash chromatography Methods 0.000 description 5
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 239000004546 suspension concentrate Substances 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 4
- 240000005979 Hordeum vulgare Species 0.000 description 4
- 235000007340 Hordeum vulgare Nutrition 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- 241000209140 Triticum Species 0.000 description 4
- 235000021307 Triticum Nutrition 0.000 description 4
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 4
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 239000004491 dispersible concentrate Substances 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 238000010353 genetic engineering Methods 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 4
- 235000009973 maize Nutrition 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 239000003053 toxin Substances 0.000 description 4
- 231100000765 toxin Toxicity 0.000 description 4
- 108700012359 toxins Proteins 0.000 description 4
- 239000004562 water dispersible granule Substances 0.000 description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
- JARQJSPDMZXUOY-UHFFFAOYSA-N 9-(2,6-dimethyl-4-prop-1-ynylphenyl)-3-(2-methoxyiminopropanoyl)-3-azaspiro[5.5]undecane-8,10-dione Chemical compound CC1=C(C(=CC(=C1)C#CC)C)C1C(CC2(CCN(CC2)C(C(C)=NOC)=O)CC1=O)=O JARQJSPDMZXUOY-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 235000006008 Brassica napus var napus Nutrition 0.000 description 3
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- 239000005562 Glyphosate Substances 0.000 description 3
- XVOKUMIPKHGGTN-UHFFFAOYSA-N Imazethapyr Chemical compound OC(=O)C1=CC(CC)=CN=C1C1=NC(C)(C(C)C)C(=O)N1 XVOKUMIPKHGGTN-UHFFFAOYSA-N 0.000 description 3
- 239000005909 Kieselgur Substances 0.000 description 3
- 240000004296 Lolium perenne Species 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
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- 230000002378 acidificating effect Effects 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 230000004071 biological effect Effects 0.000 description 3
- 238000009395 breeding Methods 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
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- 235000005822 corn Nutrition 0.000 description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
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- 235000019439 ethyl acetate Nutrition 0.000 description 3
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 3
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- 125000001072 heteroaryl group Chemical group 0.000 description 3
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- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 150000002923 oximes Chemical class 0.000 description 3
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 3
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 241000894007 species Species 0.000 description 3
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- GAFBHGCAUQFDBO-UHFFFAOYSA-N tert-butyl 2-ethyldecanoate Chemical compound CCCCCCCCC(CC)C(=O)OC(C)(C)C GAFBHGCAUQFDBO-UHFFFAOYSA-N 0.000 description 3
- 230000009261 transgenic effect Effects 0.000 description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 description 3
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- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 description 2
- RHUYHJGZWVXEHW-UHFFFAOYSA-N 1,1-Dimethyhydrazine Chemical compound CN(C)N RHUYHJGZWVXEHW-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 2
- ITNRMZNYNUEFMJ-UHFFFAOYSA-N 3-[2-(dimethylhydrazinylidene)propanoyl]-9-(2,6-dimethyl-4-prop-1-ynylphenyl)-3-azaspiro[5.5]undecane-8,10-dione Chemical compound CN(N=C(C(=O)N1CCC2(CC1)CC(C(C(C2)=O)C1=C(C=C(C=C1C)C#CC)C)=O)C)C ITNRMZNYNUEFMJ-UHFFFAOYSA-N 0.000 description 2
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- UAGIVKCHXTXTPK-MFKUBSTISA-N 9-(2,6-dimethyl-4-prop-1-ynylphenyl)-3-[(2E)-2-methoxyiminoacetyl]-3-azaspiro[5.5]undecane-8,10-dione Chemical compound CC1=C(C(=CC(=C1)C#CC)C)C1C(CC2(CCN(CC2)C(/C=N/OC)=O)CC1=O)=O UAGIVKCHXTXTPK-MFKUBSTISA-N 0.000 description 2
- UYJSQTJKNAMNGT-NJZRLIGZSA-N 9-(2,6-dimethyl-4-prop-1-ynylphenyl)-3-[(2E)-2-pyridin-2-yloxyiminopropanoyl]-3-azaspiro[5.5]undecane-8,10-dione Chemical compound CC1=C(C(=CC(=C1)C#CC)C)C1C(CC2(CCN(CC2)C(/C(/C)=N/OC2=NC=CC=C2)=O)CC1=O)=O UYJSQTJKNAMNGT-NJZRLIGZSA-N 0.000 description 2
- XHKAFDADVIRYBL-UHFFFAOYSA-N 9-(2,6-dimethyl-4-prop-1-ynylphenyl)-3-azaspiro[5.5]undecane-8,10-dione Chemical compound C1(C2=C(C)C=C(C#CC)C=C2C)C(=O)CC2(CCNCC2)CC1=O XHKAFDADVIRYBL-UHFFFAOYSA-N 0.000 description 2
- NTJRJXMJWJEUJV-UHFFFAOYSA-N 9-(2,6-dimethyl-4-prop-1-ynylphenyl)-3-azaspiro[5.5]undecane-8,10-dione hydrochloride Chemical compound Cl.CC#Cc1cc(C)c(C2C(=O)CC3(CCNCC3)CC2=O)c(C)c1 NTJRJXMJWJEUJV-UHFFFAOYSA-N 0.000 description 2
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- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
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- 125000004648 C2-C8 alkenyl group Chemical group 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 240000000491 Corchorus aestuans Species 0.000 description 2
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- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- 239000005510 Diuron Substances 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- RXCPQSJAVKGONC-UHFFFAOYSA-N Flumetsulam Chemical compound N1=C2N=C(C)C=CN2N=C1S(=O)(=O)NC1=C(F)C=CC=C1F RXCPQSJAVKGONC-UHFFFAOYSA-N 0.000 description 2
- 239000005561 Glufosinate Substances 0.000 description 2
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- 239000007821 HATU Substances 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
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- KLJUVCXLKBGKOY-UHFFFAOYSA-N n-hexylheptan-1-amine Chemical compound CCCCCCCNCCCCCC KLJUVCXLKBGKOY-UHFFFAOYSA-N 0.000 description 1
- PXSXRABJBXYMFT-UHFFFAOYSA-N n-hexylhexan-1-amine Chemical compound CCCCCCNCCCCCC PXSXRABJBXYMFT-UHFFFAOYSA-N 0.000 description 1
- SKLXFEQHEBALKG-UHFFFAOYSA-N n-hexyloctan-1-amine Chemical compound CCCCCCCCNCCCCCC SKLXFEQHEBALKG-UHFFFAOYSA-N 0.000 description 1
- NSBIQPJIWUJBBX-UHFFFAOYSA-N n-methoxyaniline Chemical compound CONC1=CC=CC=C1 NSBIQPJIWUJBBX-UHFFFAOYSA-N 0.000 description 1
- XJINZNWPEQMMBV-UHFFFAOYSA-N n-methylhexan-1-amine Chemical compound CCCCCCNC XJINZNWPEQMMBV-UHFFFAOYSA-N 0.000 description 1
- OZIXTIPURXIEMB-UHFFFAOYSA-N n-methylnonan-1-amine Chemical compound CCCCCCCCCNC OZIXTIPURXIEMB-UHFFFAOYSA-N 0.000 description 1
- SZEGKVHRCLBFKJ-UHFFFAOYSA-N n-methyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCNC SZEGKVHRCLBFKJ-UHFFFAOYSA-N 0.000 description 1
- CNCBAEHAEKNSPZ-UHFFFAOYSA-N n-methylpentadecan-1-amine Chemical compound CCCCCCCCCCCCCCCNC CNCBAEHAEKNSPZ-UHFFFAOYSA-N 0.000 description 1
- JACMPVXHEARCBO-UHFFFAOYSA-N n-pentylpentan-1-amine Chemical compound CCCCCNCCCCC JACMPVXHEARCBO-UHFFFAOYSA-N 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- RTCOGUMHFFWOJV-UHFFFAOYSA-N nicosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)C(=O)N(C)C)=N1 RTCOGUMHFFWOJV-UHFFFAOYSA-N 0.000 description 1
- FJDUDHYHRVPMJZ-UHFFFAOYSA-N nonan-1-amine Chemical compound CCCCCCCCCN FJDUDHYHRVPMJZ-UHFFFAOYSA-N 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
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- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- RFLFDJSIZCCYIP-UHFFFAOYSA-L palladium(2+);sulfate Chemical compound [Pd+2].[O-]S([O-])(=O)=O RFLFDJSIZCCYIP-UHFFFAOYSA-L 0.000 description 1
- VUYVXCJTTQJVKJ-UHFFFAOYSA-L palladium(2+);tricyclohexylphosphane;dichloride Chemical compound Cl[Pd]Cl.C1CCCCC1P(C1CCCCC1)C1CCCCC1.C1CCCCC1P(C1CCCCC1)C1CCCCC1 VUYVXCJTTQJVKJ-UHFFFAOYSA-L 0.000 description 1
- 229910000364 palladium(II) sulfate Inorganic materials 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- FIKAKWIAUPDISJ-UHFFFAOYSA-L paraquat dichloride Chemical compound [Cl-].[Cl-].C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 FIKAKWIAUPDISJ-UHFFFAOYSA-L 0.000 description 1
- 239000011236 particulate material Substances 0.000 description 1
- CHIFOSRWCNZCFN-UHFFFAOYSA-N pendimethalin Chemical compound CCC(CC)NC1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O CHIFOSRWCNZCFN-UHFFFAOYSA-N 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
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- 238000005191 phase separation Methods 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- NQQVFXUMIDALNH-UHFFFAOYSA-N picloram Chemical compound NC1=C(Cl)C(Cl)=NC(C(O)=O)=C1Cl NQQVFXUMIDALNH-UHFFFAOYSA-N 0.000 description 1
- MGOHCFMYLBAPRN-UHFFFAOYSA-N pinoxaden Chemical compound CCC1=CC(C)=CC(CC)=C1C(C1=O)=C(OC(=O)C(C)(C)C)N2N1CCOCC2 MGOHCFMYLBAPRN-UHFFFAOYSA-N 0.000 description 1
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- 238000006116 polymerization reaction Methods 0.000 description 1
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- 229920002689 polyvinyl acetate Polymers 0.000 description 1
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- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
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- 239000003380 propellant Substances 0.000 description 1
- NQLVQOSNDJXLKG-UHFFFAOYSA-N prosulfocarb Chemical compound CCCN(CCC)C(=O)SCC1=CC=CC=C1 NQLVQOSNDJXLKG-UHFFFAOYSA-N 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- NHDHVHZZCFYRSB-UHFFFAOYSA-N pyriproxyfen Chemical compound C=1C=CC=NC=1OC(C)COC(C=C1)=CC=C1OC1=CC=CC=C1 NHDHVHZZCFYRSB-UHFFFAOYSA-N 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- FFSSWMQPCJRCRV-UHFFFAOYSA-N quinclorac Chemical compound ClC1=CN=C2C(C(=O)O)=C(Cl)C=CC2=C1 FFSSWMQPCJRCRV-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 1
- BBKDWPHJZANJGB-IKJXHCRLSA-N quizalofop-P-tefuryl Chemical group O=C([C@H](OC=1C=CC(OC=2N=C3C=CC(Cl)=CC3=NC=2)=CC=1)C)OCC1CCCO1 BBKDWPHJZANJGB-IKJXHCRLSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 235000009736 ragweed Nutrition 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000012865 response to insecticide Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- MEFOUWRMVYJCQC-UHFFFAOYSA-N rimsulfuron Chemical compound CCS(=O)(=O)C1=CC=CN=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 MEFOUWRMVYJCQC-UHFFFAOYSA-N 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229940057950 sodium laureth sulfate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- NHQVTOYJPBRYNG-UHFFFAOYSA-M sodium;2,4,7-tri(propan-2-yl)naphthalene-1-sulfonate Chemical compound [Na+].CC(C)C1=CC(C(C)C)=C(S([O-])(=O)=O)C2=CC(C(C)C)=CC=C21 NHQVTOYJPBRYNG-UHFFFAOYSA-M 0.000 description 1
- SXHLENDCVBIJFO-UHFFFAOYSA-M sodium;2-[2-(2-dodecoxyethoxy)ethoxy]ethyl sulfate Chemical compound [Na+].CCCCCCCCCCCCOCCOCCOCCOS([O-])(=O)=O SXHLENDCVBIJFO-UHFFFAOYSA-M 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- OORLZFUTLGXMEF-UHFFFAOYSA-N sulfentrazone Chemical compound O=C1N(C(F)F)C(C)=NN1C1=CC(NS(C)(=O)=O)=C(Cl)C=C1Cl OORLZFUTLGXMEF-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 235000001508 sulfur Nutrition 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- UNUNCPXYUNVRRF-UHFFFAOYSA-N tert-butyl 4-(2-oxopropyl)piperidine-1-carboxylate Chemical compound CC(=O)CC1CCN(C(=O)OC(C)(C)C)CC1 UNUNCPXYUNVRRF-UHFFFAOYSA-N 0.000 description 1
- UNGFTBZOLJAYQP-UHFFFAOYSA-N tert-butyl 8,10-dioxo-3-azaspiro[5.5]undecane-3-carboxylate Chemical compound O=C1CC2(CCN(CC2)C(=O)OC(C)(C)C)CC(C1)=O UNGFTBZOLJAYQP-UHFFFAOYSA-N 0.000 description 1
- PIVZDZNBFLRDEH-UHFFFAOYSA-N tert-butyl 9-(4-bromo-2,6-dimethylphenyl)-8,10-dioxo-3-azaspiro[5.5]undecane-3-carboxylate Chemical compound BrC1=CC(=C(C(=C1)C)C1C(CC2(CCN(CC2)C(=O)OC(C)(C)C)CC1=O)=O)C PIVZDZNBFLRDEH-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000005621 tetraalkylammonium salts Chemical class 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 238000003971 tillage Methods 0.000 description 1
- 229960004394 topiramate Drugs 0.000 description 1
- IYMLUHWAJFXAQP-UHFFFAOYSA-N topramezone Chemical compound CC1=C(C(=O)C2=C(N(C)N=C2)O)C=CC(S(C)(=O)=O)=C1C1=NOCC1 IYMLUHWAJFXAQP-UHFFFAOYSA-N 0.000 description 1
- 229940047183 tribulus Drugs 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- ZEWQUBUPAILYHI-UHFFFAOYSA-N trifluoperazine Chemical compound C1CN(C)CCN1CCCN1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C21 ZEWQUBUPAILYHI-UHFFFAOYSA-N 0.000 description 1
- 229960002324 trifluoperazine Drugs 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 description 1
- 229960001082 trimethoprim Drugs 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- 241001478887 unidentified soil bacteria Species 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
- A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/20—Spiro-condensed ring systems
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P13/00—Herbicides; Algicides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
本发明涉及具有式(I)的化合物,其中R1、R2、R3、R4和G如本文所定义。本发明进一步涉及包含具有式(I)的化合物的除草组合物、其用于控制杂草的用途,特别是在有用植物的作物中。
Description
本发明涉及新颖的除草化合物、其制备方法、包含所述新颖的化合物的除草组合物、以及其用于控制杂草的用途。
例如,WO 2014/096289和WO 2015/197468中披露了被具有含炔基取代基的苯基取代的除草环状二酮化合物。本发明涉及新颖的具有改进特性的除草环己二酮衍生物。
因此,根据本发明,提供了一种具有式(I)的化合物
其中
R1选自由以下组成的组:甲基、乙炔基、1-丙炔基、苯基和包含一个或两个氮杂原子的5元或6元杂芳基,所述苯基和杂芳基任选地被一个或两个R9取代基取代;
R2选自由以下组成的组:甲基、乙基、甲氧基和氯;
R3选自由以下组成的组:甲基、乙基、甲氧基和氯;
R4是-C(O)C(R5)=N-O-R6或-C(O)C(R5)=N-NR7R8;
R5选自由以下组成的组:氢、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基-和C1-C6卤代烷氧基-;
R6选自由以下组成的组:氢、C1-C6烷基、C1-C6烷氧基C1-C3烷基-、C3-C6环烷基、-CH2CN、四氢吡喃基-、苯基和-吡啶基,其中所述苯基和吡啶基任选地被一个、两个或三个独立地选自由以下组成的组的取代基取代:C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C2-C3烯基、C2-C3炔基、卤素、氰基和硝基;
R7是氢或C1-C6烷基;
R8是氢或C1-C6烷基;
R9独立地选自由以下组成的组:C1-C4烷基、C1-C4卤代烷基、氰基和卤素;
G选自由以下组成的组:氢、-(CH2)n-Ra、-C(O)-Ra、-C(O)-(CRcRd)n-O-Rb、-C(O)-(CRcRd)n-S-Rb、-C(O)NRaRa、-S(O)2-Ra和C1-C8烷氧基-C1-C3烷基-;
Ra独立地选自由以下组成的组:氢、C1-C8烷基、C1-C3卤代烷基、C2-C8烯基、C2-C8炔基、C3-C6环烷基、杂环基和苯基,其中所述杂环基和苯基任选地被一个、两个或三个独立地选自由以下组成的组的取代基取代:C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C2-C3烯基、C2-C3炔基、卤素、氰基和硝基;
Rb选自由以下组成的组:C1-C8烷基、C1-C3卤代烷基、C2-C8烯基、C2-C8炔基、C3-C6环烷基、杂环基和苯基,其中所述杂环基和苯基任选地被一个、两个或三个独立地选自由以下组成的组的取代基取代:C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C2-C3烯基、C2-C3炔基、卤素、氰基和硝基;
Rc是氢或C1-C3烷基;
Rd是氢或C1-C3烷基;并且
n独立地是0、1或2;
或其农业上可接受的盐。
烷基(例如C1-C6烷基)包括例如甲基(Me,CH3)、乙基(Et,C2H5)、正丙基(n-Pr)、异丙基(i-Pr)、正丁基(n-Bu)、异丁基(i-Bu)、仲丁基(s-Bu)和叔丁基(t-Bu)。
烯基和炔基部分可以呈直链或支链的形式,并且烯基部分在适当时可以是具有(E)-或(Z)-构型。实例是乙烯基、烯丙基以及炔丙基。烯基和炔基部分可以以任何组合含有一个或多个双键和/或三键。
卤素(或卤代基)涵盖了氟、氯、溴或碘。这对应地适用于其他定义上下文中的卤素,如卤代烷基。
卤代烷基(例如C1-C6卤代烷基)是例如氟甲基、二氟甲基、三氟甲基、氯甲基、二氯甲基、三氯甲基、2,2,2-三氟乙基、2-氟乙基、2-氯乙基、五氟乙基、1,1-二氟-2,2,2-三氯乙基、2,2,3,3-四氟乙基和2,2,2-三氯乙基、七氟正丙基和全氟正己基。
烷氧基(例如C1-C4烷氧基-)是例如甲氧基、乙氧基、丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基或叔丁氧基,优选甲氧基和乙氧基。
烷氧基烷基(例如C1-C8烷氧基-C1-C3烷基-)包括例如甲氧基甲基、甲氧基乙基、乙氧基甲基、乙氧基乙基、正丙氧基甲基、正丙氧基乙基、异丙氧基甲基或异丙氧基乙基。
环烷基(例如C3-C6环烷基-)包括例如环丙基(c-丙基,c-Pr)、环丁基(c-丁基、c-Bu)、环戊基(c-戊基)和环己基(c-己基)并且如所指出的可以是取代的或未取代的。
本发明还涉及具有式(I)的化合物的农业上可接受的盐。此类盐包括能够与胺、碱金属和碱土金属碱或者季铵碱形成的那些。在作为成盐物的碱金属氢氧化物和碱土金属氢氧化物之中,应特别提及锂、钠、钾、镁以及钙的氢氧化物,但尤其是钠和钾的氢氧化物。根据本发明的具有式(I)的化合物还包括在盐形成期间可以形成的水合物。
适合于形成铵盐的胺的实例包括氨以及伯、仲和叔C1-C18烷基胺,C1-C4羟基烷基胺以及C2-C4烷氧基烷基胺,例如甲胺、乙胺、正丙胺、异丙胺、四种丁胺异构体、正戊胺、异戊胺、己胺、庚胺、辛胺、壬胺、癸胺、十五胺、十六胺、十七胺、十八胺、甲基乙基胺、甲基异丙胺、甲基己胺、甲基壬胺、甲基十五胺、甲基十八胺、乙基丁胺、乙基庚胺、乙基辛胺、己基庚胺、己基辛胺、二甲胺、二乙胺、二-正丙胺、二异丙胺、二-正丁胺、二-正戊胺、二异戊胺、二己胺、二庚胺、二辛胺、乙醇胺、正丙醇胺、异丙醇胺、N,N-二乙醇胺、N-乙基丙醇胺、N-丁基乙醇胺、烯丙胺、正丁-2-烯胺、正戊-2-烯胺、2,3-二甲基丁-2-烯胺、二丁-2-烯胺、正己-2-烯胺、丙二胺、三甲胺、三乙胺、三-正丙胺、三异丙胺、三-正丁胺、三异丁胺、三-仲丁胺、三-正戊胺、甲氧基乙胺以及乙氧基乙胺;杂环胺,例如吡啶、喹啉、异喹啉、吗啉、哌啶、吡咯烷、二氢吲哚、奎宁环以及氮杂卓;伯芳基胺,例如苯胺,甲氧基苯胺,乙氧基苯胺,邻-、间-和对-甲苯胺,苯二胺,联苯胺,萘胺以及邻-、间-和对-氯苯胺;但尤其是三乙胺、异丙胺和二异丙胺。
在本发明的一个实施例中,在具有式(I)的化合物中,R1是1-丙炔基,R2是甲基或甲氧基,并且R3是甲基或甲氧基。
在本发明的另一个实施例中,R1是任选地被一个或两个R9取代基取代的苯基,所述取代基例如选自由以下组成的组:氰基、氯和氟。
在本发明的另一个实施例中,R1是包含一个或两个氮杂原子的5元或6元杂芳基,所述杂芳基任选地被一个或两个R9取代基取代,所述取代基例如选自由以下组成的组:氰基、氯和氟。在优选的实施例中,所述杂芳基选自由以下组成的组:吡啶基、嘧啶基和吡唑基。
在本发明的一个实施例中,R2是甲氧基、氯或甲基。在本发明的优选实施例中,R2是甲基。
在本发明的一个实施例中,R3是甲基或甲氧基,优选地甲基。
在本发明的一个实施例中,R2是甲基并且R3是甲基。
在本发明的一个实施例中,R2是甲基并且R3是甲氧基。
在本发明的一个实施例中,R2是甲氧基并且R3是甲氧基。
在本发明的另一个实施例中,R5是氢或C1-C6烷基(尤其是甲基、乙基或叔丁基)。优选地,R5是氢或甲基。
在本发明的另一个实施例中,R4是-C(O)C(R5)=N-O-R6。在此实施例中,R5优选地是氢或C1-C6烷基(尤其是甲基、乙基或叔丁基),并且R6选自由以下组成的组:氢、C1-C6烷基(优选地甲基、乙基、正丙基、异丙基、正丁基和叔丁基)和C1-C6烷氧基C1-C3烷基-(优选地甲氧基乙基-)。
在本发明的另一个实施例中,R4是-C(O)C(R5)=N-NR7R8。在此实施例中,R5优选地是氢或C1-C6烷基(尤其是甲基、乙基或叔丁基),R7是氢或C1-C6烷基(优选地甲基或乙基),并且R8是氢或C1-C6烷基(优选地甲基或乙基)。
在本发明的一个实施例中,G选自由以下组成的组:氢、C1-C8烷基(例如甲基、乙基、正丙基、异丙基、正丁基、叔丁基)、-C2-C8烯基(例如乙烯基)、C2-C8炔基(例如炔丙基)、-C(O)C1-C8烷基(更优选-C(O)C1-C6烷基,例如-C(O)异丙基和-C(O)叔丁基)和-C(O)-O-C1-C8烷基(更优选-C(O)-O-C1-C6烷基,例如-C(O)-O-甲基)。在优选的实施例中,G是氢。
取决于取代基的性质,具有式(I)的化合物可以以不同的异构体形式存在。当G是氢时,例如,具有式(I)的化合物可以以不同的互变异构体形式存在。
本发明覆盖所有此类异构体和互变异构体及其处于所有比例的混合物。此外,当取代基含有双键时,可能存在顺式-和反式-异构体。这些异构体也在所要求保护的具有式(I)的化合物的范围内。具有式(I)的化合物可以含有不对称中心并且可以作为单一对映异构体、以任何比例的对映异构体对而存在,或在存在多于一个不对称中心的情况下,含有所有可能比率的非对映异构体。典型地,与其他可能性相比,这些对映异构体之一具有增强的生物活性。
根据本发明的具有式(I)的化合物可以自身被用作除草剂,但是通常使用配制辅助剂(如载体、溶剂和表面活性剂(SFA))将它们配制成除草组合物。因此,本发明进一步提供了一种除草组合物,所述除草组合物包含根据前述权利要求中任一项所述的除草化合物和农业上可接受的配制辅助剂。组合物可以呈浓缩物的形式,在使用前稀释这些浓缩物,尽管也可以制成即用型组合物。最终稀释通常用水进行,但是可以替代水或除了水之外用例如液体肥料、微量营养素、生物有机体、油或溶剂进行。
除草组合物通常包含按重量计从0.1%至99%、尤其是按重量计从0.1%至95%的具有式(I)的化合物和按重量计从1%至99.9%的配制辅助剂,所述配制辅助剂优选地包括按重量计从0%至25%的表面活性物质。
这些组合物可以选自多种配制品类型,这些配制品类型中的很多是从Manual onDevelopment and Use of FAO Specifications for Plant Protection Products[发展和使用FAO植保产品规格指南手册],第5版,1999中得知。这些包括可尘化粉剂(DP)、可溶性粉剂(SP)、水溶性颗粒剂(SG)、水可分散性颗粒剂(WG)、可湿性粉剂(WP)、颗粒剂(GR)(缓释或快释的)、可溶的浓缩物(SL)、可与油混溶的液体(OL)、超低容量液剂(UL)、可乳化的浓缩物(EC)、可分散性浓缩物(DC)、乳液(水包油(EW)和油包水(EO)二者)、微乳液(ME)、悬浮浓缩物(SC)、气溶胶、胶囊悬浮液(CS)以及种子处理配制品。在任何情况下,所选择的配制品类型将取决于所设想的具体目的以及具有式(I)的化合物的物理、化学和生物特性。
可尘化粉剂(DP)可以通过以下方式制备:将具有式(I)的化合物与一种或多种固体稀释剂(例如,天然粘土、高岭土、叶蜡石、膨润土、氧化铝、蒙脱石、砂藻土(kieselguhr)、白垩、硅藻土(diatomaceous earths)、磷酸钙、碳酸钙和碳酸镁、硫、石灰、面粉、滑石和其他有机和无机的固体载体)混合并将混合物机械地碾磨成细粉末。
可溶性粉剂(SP)可以通过以下方式制备:将具有式(I)的化合物与一种或多种水溶性无机盐(如碳酸氢钠、碳酸钠或硫酸镁)或一种或多种水溶性有机固体(如多糖)以及任选地一种或多种湿润剂、一种或多种分散剂或所述试剂的混合物混合以改进水分散性/水溶性。然后将混合物研磨成细粉末。还可以将类似的组合物颗粒化以形成水溶性颗粒剂(SG)。
可湿性粉剂(WP)可以通过以下方式制备:将具有式(I)的化合物与一种或多种固体稀释剂或载体、一种或多种湿润剂以及优选地,一种或多种分散剂,以及任选地,一种或多种悬浮剂混合以促进在液体中的分散。然后将混合物研磨成细粉末。还可以将类似的组合物颗粒化以形成水可分散性颗粒剂(WG)。
颗粒剂(GR)可以通过将具有式(I)的化合物与一种或多种粉状固体稀释剂或载体的混合物颗粒化形成,或者由预成型的空白颗粒通过将具有式(I)的化合物(或其在合适的试剂中的溶液)吸收进多孔颗粒材料(如浮石、凹凸棒石粘土、漂白土、砂藻土、硅藻土或磨碎的玉米芯),或通过将具有式(I)的化合物(或其在合适的试剂中的溶液)吸附到硬芯材料(如沙、硅酸盐、矿物碳酸盐、硫酸盐或磷酸盐)上并且如果必要的话,进行干燥来形成。通常用于帮助吸收或吸附的试剂包括溶剂(如脂肪族和芳香族石油溶剂、醇、醚、酮以及酯)和粘着剂(如聚乙酸乙烯酯、聚乙烯醇、糊精、糖以及植物油)。颗粒剂中还可以包含一种或多种其他添加剂(例如乳化剂、湿润剂或分散剂)。
可分散的浓缩物(DC)可以通过将具有式(I)的化合物溶于水或有机溶剂(如酮、醇或二醇醚)中来制备。这些溶液可以含有表面活性剂(例如以改善水稀释或防止喷雾罐中的结晶)。
可乳化的浓缩物(EC)或水包油乳液(EW)可以通过将具有式(I)的化合物溶于有机溶剂(任选地含有一种或多种湿润剂、一种或多种乳化剂或者所述试剂的混合物)中来制备。在EC中使用的合适的有机溶剂包括芳香族烃(如烷基苯或烷基萘,例如SOLVESSO 100、SOLVESSO 150和SOLVESSO 200;SOLVESSO是注册商标)、酮(如环己酮或甲基环己酮)和醇(如苯甲醇、糠醇或丁醇)、N-烷基吡咯烷酮(如N-甲基吡咯烷酮或N-辛基吡咯烷酮)、脂肪酸的二甲基酰胺(如C8-C10脂肪酸二甲基酰胺)和氯化烃。EC产品可以在添加到水中时自发地乳化,从而产生具有足够稳定性的乳液,以允许通过适当设备进行喷洒施用。
EW的制备涉及获得作为液体(如果它在室温下不是液体,则它可以在典型地低于70℃的合理温度下熔化)或处于溶液中(通过将它溶于适当的溶剂中)的具有式(I)的化合物,并且然后在高剪切下将所得液体或溶液乳化到包含一种或多种SFA的水中,以产生乳液。在EW中使用的合适的溶剂包括植物油、氯化烃(如氯苯)、芳香族溶剂(如烷基苯或烷基萘)以及在水中具有低溶解度的其他适当的有机溶剂。
微乳液(ME)可以通过将水与一种或多种溶剂和一种或多种SFA的共混物混合,以自发地产生热力学稳定的各向同性的液体配制品来制备。具有式(I)的化合物最初存在于水中或溶剂/SFA共混物中。在ME中使用的合适的溶剂包括此前描述的在EC或EW中使用的那些。ME可以是水包油体系或油包水体系(存在哪种体系可以通过电导率测量来测定)并且可以适用于在同一配制品中混合水溶性的和油溶性的杀有害生物剂。ME适用于稀释到水中,保持为微乳液或形成常规的水包油乳液。
悬浮浓缩物(SC)可以包括具有式(I)的化合物的精细分散的不溶固体颗粒的水性或非水性悬浮液。SC可以通过将具有式(I)的固体化合物任选地与一种或多种分散剂在合适的介质中球磨或珠磨,以产生该化合物的细颗粒悬浮液来制备。组合物中可以包含一种或多种湿润剂,并且可以包含悬浮剂以降低颗粒沉降的速率。可替代地,可以干磨具有式(I)的化合物并且将其添加到含有此前描述的试剂的水中,以产生希望的最终产物。
气溶胶配制品包含具有式(I)的化合物和合适的推进剂(例如正丁烷)。还可将具有式(I)的化合物溶于或分散于合适的介质(例如水或可与水混溶的液体,如正丙醇)中以提供在不加压的手动喷雾泵中使用的组合物。
胶囊悬浮液(CS)可以以与制备EW配制品类似的方式来制备,但具有另外的聚合阶段,使得获得油滴的水性分散体,其中每个油滴都被聚合物壳所包裹并且含有具有式(I)的化合物以及任选地用于该油滴的载体或稀释剂。聚合物壳可以通过界面缩聚反应或通过凝聚程序产生。组合物可以提供具有式(I)的化合物的受控释放并且它们可以用于种子处理。具有式(I)的化合物还可以配制在可生物降解的聚合物基质中以提供该化合物的缓慢的、受控的释放。
组合物可以包含一或多种添加剂以改善该组合物的生物学性能,例如通过改善在表面上的湿润性、保持或分布;被处理表面上的抗雨水性;或具有式(I)的化合物的吸收或流动。此类添加剂包括表面活性剂(SFA)、基于油的喷雾添加剂,例如某些矿物油或天然植物油(如大豆和菜籽油),以及这些与其他生物增强辅助剂(可帮助或改变具有式(I)的化合物的作用的成分)的共混物。
湿润剂、分散剂和乳化剂可以是阳离子类型、阴离子类型、两性类型或非离子类型的SFA。
合适的阳离子类型的SFA包括季铵化合物(例如十六烷基三甲基溴化铵)、咪唑啉以及胺盐。
适合的阴离子型SFA包括脂肪酸的碱金属盐、脂肪族硫酸单酯的盐(例如月桂硫酸钠)、磺化的芳香族化合物的盐(例如十二烷基苯磺酸钠、十二烷基苯磺酸钙、丁基萘磺酸盐以及二-异丙基-萘磺酸钠和三-异丙基-萘磺酸钠的混合物)、醚硫酸盐、醇醚硫酸盐(例如月桂醇聚醚-3-硫酸钠)、醚羧酸盐(例如月桂醇聚醚-3-羧酸钠)、磷酸酯(来自一种或多种脂肪醇与磷酸(主要是单酯)或与五氧化二磷(主要是二酯)之间反应的产物,例如月桂醇与四磷酸之间的反应;另外这些产物可以被乙氧基化)、硫代琥珀酰胺酸盐、石蜡或烯烃磺酸盐、牛磺酸盐以及木质素磺酸盐。
合适的两性类型的SFA包括甜菜碱、丙酸盐和甘氨酸盐。
合适的非离子类型的SFA包括环氧烷(如环氧乙烷、环氧丙烷、环氧丁烷或其混合物)与脂肪醇(如油醇或鲸蜡醇)或与烷基酚(如辛基酚、壬基酚或辛基甲酚)的缩合产物;衍生自长链脂肪酸或己糖醇酐的偏酯;所述偏酯与环氧乙烷的缩合产物;嵌段聚合物(包含环氧乙烷和环氧丙烷);烷醇酰胺;单酯(例如脂肪酸聚乙二醇酯);胺氧化物(例如月桂基二甲基氧化胺);和卵磷脂。
合适的悬浮剂包括亲水性胶体(如多糖、聚乙烯吡咯烷酮或羧甲基纤维素钠)和膨胀性粘土(如膨润土或凹凸棒石)。
本发明的除草化合物还可以与一种或多种另外的除草剂和/或植物生长调节剂混合使用。此类另外的除草剂或植物生长调节剂的实例包括乙草胺、三氟羧草醚(包括三氟羧草醚-钠)、苯草醚、莠灭净、氨唑草酮、氯氨吡啶酸、杀草强、莠去津、苄嘧磺隆(包括苄嘧磺隆-甲基)、灭草松、氟吡草酮、双丙氨膦、双草醚-钠、二氯异噁草酮、除草定、溴苯腈、丁草胺、氟丙嘧草酯、唑草酮(包括唑草酮-乙基)、氯酯磺草胺(包括氯酯磺草胺-甲基)、氯嘧磺隆(包括氯嘧磺隆-乙基)、绿麦隆、氯磺隆、环庚草醚、氯酰草膦、烯草酮、炔草酸(包括炔草酯)、异噁草酮、二氯吡啶酸、环吡拉尼(cyclopyranil)、环吡瑞莫(cyclopyrimorate)、环丙嘧磺隆、氰氟草酯(包括氰氟草酯-丁基)、2,4-D(包括其胆碱盐和2-乙基己酯)、2,4-DB、甜菜安、麦草畏(包括其铝、氨基丙基、双-氨基丙基甲基、胆碱、二氯丙、二甘醇胺、二甲胺、二甲铵、钾和钠盐)、双氯磺草胺、吡氟酰草胺、氟吡草腙、二甲草胺、精二甲吩草胺、二溴敌草快、敌草隆、乙丁烯氟灵、乙氧呋草黄、噁唑禾草灵(包括精噁唑禾草灵-乙基)、苯磺噁唑草(fenoxasulfone)、芬奎崔顿(fenquinotrione)、四唑酰草胺、啶嘧磺隆、双氟磺草胺、氯氟吡啶酯(包括氯氟吡啶酯-苄基)、吡氟禾草灵(包括精吡氟禾草灵-丁基)、氟酮磺隆(包括氟酮磺隆-钠)、氟噻草胺、唑嘧磺草胺、丙炔氟草胺、氟啶嘧磺隆(包括氟啶嘧磺隆-甲基-钠)、氯氟吡氧乙酸(包括氯氟吡氧乙酸-甲基庚基(fluroxypyr-meptyl))、氟黄胺草醚、甲酰胺磺隆、草铵膦(包括其铵盐)、草甘膦(包括其二铵、异丙铵和钾盐)、氟氯吡啶酯(包括氟氯吡啶酯-甲基)、氟吡甲禾灵(包括氟吡甲禾灵-甲基)、环嗪酮、hydantocidin、甲氧咪草烟、甲咪唑烟酸、灭草烟、咪草烟、茚嗪氟草胺、碘甲磺隆(包括碘甲磺隆-甲基-钠)、iofensulfuron(包括iofensulfuron-钠)、碘苯腈、异丙隆、异噁唑草酮、lancotrione、MCPA、MCPB、精二甲四氯丙酸(mecoprop-P)、甲基二磺隆(包括甲基二磺隆-甲基)、甲基磺草酮、苯嗪草酮、吡草胺、异噁噻草醚(methiozolin)、异丙甲草胺、磺草唑胺、嗪草酮、甲磺隆、敌草胺、烟嘧磺隆、达草灭、噁草酮、环氧嘧磺隆、乙氧氟草醚、二氯化百草枯、二甲戊乐灵、五氟磺草胺、苯敌草、毒莠定、唑啉草酯、丙草胺、氟嘧磺隆-甲基、敌稗、喔草酯、丙嗪嘧磺隆、戊炔草胺、苄草丹、氟磺隆、双唑草腈、吡草醚(pyraflufen)(包括吡草醚-乙基)、磺酰草吡唑、哒草特、环酯草醚、吡丙醚、砜吡草唑(pyroxasulfone)、啶磺草胺、二氯喹啉酸、氯甲喹啉酸、喹禾灵(包括精喹禾灵-乙基和喹禾糠酯(quizalofop-P-tefuryl))、砜嘧磺隆、嘧啶肟草醚、烯禾啶、西玛津、精异丙甲草胺、甲磺草胺、磺酰磺隆、丁噻隆、特呋三酮、环磺酮、特丁津、特丁净、噻酮磺隆、噻吩磺隆、氟嘧硫草酯(tiafenacil)、托比利特(tolpyralate)、苯吡唑草酮、三甲苯草酮、氟酮磺草胺、野麦畏、醚苯磺隆、苯磺隆(包括苯磺隆-甲基)、绿草定、三氟啶磺隆(包括三氟啶磺隆-钠)、三氟草嗪(trifludimoxazin)、氟乐灵、氟胺磺隆、4-羟基-1-甲氧基-5-甲基-3-[4-(三氟甲基)-2-吡啶基]咪唑啉-2-酮、4-羟基-1,5-二甲基-3-[4-(三氟甲基)-2-吡啶基]咪唑啉-2-酮、5-乙氧基-4-羟基-1-甲基-3-[4-(三氟甲基)-2-吡啶基]咪唑啉-2-酮、4-羟基-1-甲基-3-[4-(三氟甲基)-2-吡啶基]咪唑啉-2-酮、4-羟基-1,5-二甲基-3-[1-甲基-5-(三氟甲基)吡唑-3-基]咪唑啉-2-酮、(4R)1-(5-叔丁基异噁唑-3-基)-4-乙氧基-5-羟基-3-甲基-咪唑啉-2-酮、3-[2-(3,4-二甲氧基苯基)-6-甲基-3-氧代-哒嗪-4-羰基]二环[3.2.1]辛烷-2,4-二酮、2-[2-(3,4-二甲氧基苯基)-6-甲基-3-氧代-哒嗪-4-羰基]-5-甲基-环己烷-1,3-二酮、2-[2-(3,4-二甲氧基苯基)-6-甲基-3-氧代-哒嗪-4-羰基]环己烷-1,3-二酮、2-[2-(3,4-二甲氧基苯基)-6-甲基-3-氧代-哒嗪-4-羰基]-5,5-二甲基-环己烷-1,3-二酮、6-[2-(3,4-二甲氧基苯基)-6-甲基-3-氧代-哒嗪-4-羰基]-2,2,4,4-四甲基-环己烷-1,3,5-三酮、2-[2-(3,4-二甲氧基苯基)-6-甲基-3-氧代-哒嗪-4-羰基]-5-乙基-环己烷-1,3-二酮、2-[2-(3,4-二甲氧基苯基)-6-甲基-3-氧代-哒嗪-4-羰基]-4,4,6,6-四甲基-环己烷-1,3-二酮、2-[6-环丙基-2-(3,4-二甲氧基苯基)-3-氧代-哒嗪-4-羰基]-5-甲基-环己烷-1,3-二酮、3-[6-环丙基-2-(3,4-二甲氧基苯基)-3-氧代-哒嗪-4-羰基]二环[3.2.1]辛烷-2,4-二酮、2-[6-环丙基-2-(3,4-二甲氧基苯基)-3-氧代-哒嗪-4-羰基]-5,5-二甲基-环己烷-1,3-二酮、6-[6-环丙基-2-(3,4-二甲氧基苯基)-3-氧代-哒嗪-4-羰基]-2,2,4,4-四甲基-环己烷-1,3,5-三酮、2-[6-环丙基-2-(3,4-二甲氧基苯基)-3-氧代-哒嗪-4-羰基]环己烷-1,3-二酮、4-[2-(3,4-二甲氧基苯基)-6-甲基-3-氧代-哒嗪-4-羰基]-2,2,6,6-四甲基-四氢吡喃-3,5-二酮和4-[6-环丙基-2-(3,4-二甲氧基苯基)-3-氧代-哒嗪-4-羰基]-2,2,6,6-四甲基-四氢吡喃-3,5-二酮。
具有式(I)的化合物的混合配伍物还可以呈酯或盐的形式,如例如在ThePesticide Manual[杀有害生物剂手册],第十六版,英国作物保护委员会(British CropProtection Council),2012中所提到的。
具有式(I)的化合物还可以与其他农用化学品(如杀真菌剂、杀线虫剂或杀昆虫剂)混合使用,其实例在The Pesticide Manual[杀有害生物剂手册]中给出。
具有式(I)的化合物与混合配伍物的混合比优选地是从1:100至1000:1。
这些混合物可以有利地用于以上提到的配制品中(在这种情况下“活性成分”涉及具有式(I)的化合物与混合配伍物的对应混合物)。
本发明的化合物或混合物还可以与一种或多种除草剂安全剂组合使用。此类安全剂的实例包括解草嗪、解草酯(包括解毒喹)、环丙磺酰胺、二氯丙烯胺、解草唑(包括解草唑-乙基)、解草啶、氟草肟、解草噁唑、双苯噁唑酸(包括双苯噁唑酸-乙基)、吡唑解草酸(mefenpyr)(包括吡唑解草酸-二乙基)、metcamifen和解草腈。
特别优选的是具有式(I)的化合物与环丙磺酰胺、双苯噁唑酸-乙基、解毒喹和/或metcamifen的混合物。
具有式(I)的化合物的安全剂还可以呈酯或盐的形式,如例如在The PesticideManual[杀有害生物剂手册],第16版(BCPC),2012中所提到的。对解毒喹的提及还适用于其锂、钠、钾、钙、镁、铝、铁、铵、季铵、锍或鏻盐(如在WO 02/34048中披露的)。
优选地,具有式(I)的化合物与安全剂的混合比是从100:1至1:10,尤其是从20:1至1:1。
这些混合物可以有利地用于以上提到的配制品中(在这种情况下“活性成分”涉及具有式(I)的化合物与安全剂的对应混合物)。
本发明仍进一步提供了一种在包括作物植物和杂草的场所处控制杂草的方法,其中所述方法包括向所述场所施用控制杂草量的根据本发明的组合物。‘控制’意指杀死、减少或延迟生长或防止或减少发芽。通常有待控制的植物是不想要的植物(杂草)。‘场所’意指其中植物正生长或将生长的区域。
具有式(I)的化合物的施用比率可以在宽范围内变化并且取决于土壤的性质、施用方法(出苗前或出苗后;拌种;施用至种子犁沟;免耕施用等)、作物植物、有待控制的一种或多种杂草、主要气候条件、以及受施用方法、施用时间和目标作物支配的其他因素。根据本发明的具有式(I)的化合物通常以从10至2000g/ha、尤其是从50至1000g/ha的比率施用。
通常通过喷洒组合物进行施用,典型地是通过用于大面积的装在拖拉机上的喷洒机,但是还可以使用其他方法如撒粉(针对粉剂)、滴加或者浸湿。
可以使用根据本发明的组合物的有用植物包括作物如谷物,例如大麦和小麦、棉花、油菜、向日葵、玉米、稻、大豆、甜菜、甘蔗和草皮。
作物植物还可以包括树,如果树、棕榈树、椰子树或其他坚果。还包括藤本植物(如葡萄)、灌木果树、果实植物和蔬菜。
作物应被理解为还包括通过常规的育种方法或通过基因工程已经赋予对除草剂或多种类别的除草剂(例如ALS-抑制剂、GS-抑制剂、EPSPS-抑制剂、PPO-抑制剂、ACC酶-抑制剂和HPPD-抑制剂)的耐受性的那些作物。通过常规的育种方法已经赋予对咪唑啉酮(例如,甲氧咪草烟)的耐受性的作物的实例是夏季油菜(卡诺拉(canola))。通过基因工程方法已经赋予对除草剂的耐受性的作物的实例包括例如对草甘膦和草铵膦有抗性的玉米品种,其是在商标名/>和/>下是可商购的。
作物还应理解为通过基因工程方法已经赋予对有害昆虫有抗性的那些,例如Bt玉米(对欧洲玉米螟有抗性)、Bt棉花(对棉铃象鼻虫有抗性)以及还有Bt马铃薯(对科罗拉多甲虫有抗性)。Bt玉米的实例是的Bt 176玉米杂交体(先正达种子公司(SyngentaSeeds))。Bt毒素是由苏芸金芽孢杆菌土壤细菌天然形成的蛋白质。毒素或能够合成此类毒素的转基因植物的实例被描述在EP-A-451878、EP-A-374 753、WO 93/07278、WO 95/34656、WO 03/052073和EP-A-427 529中。包括一个或多个编码杀昆虫剂抗性和表达一种或多种毒素的基因的转基因植物的实例是/>(玉米)、/> (玉米)、(棉花)、/>(棉花)、/>(马铃薯)、/>和/>植物作物或其种子材料均可以是抗除草剂的并且同时是抗昆虫摄食的(“叠加的”转基因结果)。例如,种子可以具有表达杀昆虫的Cry3蛋白的能力,而同时对草甘膦是耐受的。
作物还应被理解为包括通过常规的育种或基因工程的方法获得并且含有所谓的输出型性状(例如改进的储存稳定性、更高的营养价值和改进的香味)的那些。
其他有用的植物包括例如在高尔夫球场、草地、公园和路旁的或者商业上种植用于草地的草皮草,和观赏植物,如花卉或者灌木。
可以使用这些组合物来控制不想要的植物(统称为‘杂草’)。有待控制的杂草既可以是单子叶的物种,例如剪股颖属、看麦娘属、燕麦属、臂形草属、雀麦属、蒺藜草属、莎草属、马唐属、稗属、穇属、黑麦草属、雨久花属、筒轴茅属、慈姑属、藨草属、狗尾草属以及高粱属,也可以是双子叶的物种,例如苘麻属、苋属、豚草属、藜属、菊属、白酒草属、拉拉藤属、番薯属、旱金莲属、黄花稔属、白芥属、茄属、繁缕属、婆婆纳属、堇菜属以及苍耳属。已经示出本发明的化合物展现出对抗某些禾本科杂草物种(尤其是多年生黑麦草(LoliumPerenne))的特别良好的活性。杂草还可以包括可被认为是作物植物但是在作物区外生长的植物(‘逃逸者(escapes)’),或从先前栽培的不同作物留下的种子生长的植物(‘志愿者(volunteers)’)。此类志愿者或逃逸者可以是对某些其他除草剂耐受的。
本发明的化合物可以根据以下方案来制备。
具有式(I)的化合物(其中G不是氢)可以通过使用已知的方法用试剂G-Z(其中G-Z是烷基化剂(如烷基卤)、酰化剂(如酰基氯或酸酐)、磺酰化剂(如磺酰氯)、氨基甲酰化剂(如氨基甲酰氯)或者碳酸化剂(如氯甲酸盐))处理具有式(I)的化合物(其中G是氢))来制备。
方案1
具有式(I)的化合物可以通过在合适的钯催化剂、碱的存在下并且在合适的溶剂中,使具有式(A)的碘叶立德(iodonium ylide)(其中Ar是任选取代的苯基)与具有式(B)的芳基硼酸反应来制备。
方案2
合适的钯催化剂通常是钯(II)或钯(0)络合物,例如二卤化钯(II)、乙酸钯(II)、硫酸钯(II)、双(三苯基膦)-二氯化钯(II)、双(三环戊基膦)二氯化钯(II)、双(三环己基-膦)二氯化钯(II)、双(二亚苄基丙酮)钯(0)或四-(三苯基膦)钯(0)。钯催化剂还可以由钯(II)或钯(0)化合物通过与希望的配体络合(通过例如使待络合的钯(II)盐(例如二氯化钯(II)(PdCl2)或乙酸钯(II)(Pd(OAc)2))与希望的配体(例如三苯基膦(PPh3)、三环戊基膦、三环已基膦、2-二环己基膦-2’,6’-二甲氧基联苯或2-二环己基膦-2’,4’,6’-三异丙基联苯)以及选择的溶剂一起与具有式(N)的化合物、具有式(O)的芳基硼酸、以及碱进行结合)来“原位”制备。还合适的是二齿配体,例如1,1'-双(二苯基膦基)二茂铁或1,2-双(二苯基膦基)乙烷。通过加热反应介质,C-C偶联反应所需的钯(II)络合物或钯(0)络合物因此“原位”形成,并且然后引发C-C偶联反应。
钯催化剂基于具有式(N)的化合物以从0.001至50mol%的量、优选以从0.1至15mol%的量使用。反应还可以在其他添加剂(如四烷基铵盐,例如四丁基溴化铵)存在下进行。优选地,钯催化剂是乙酸钯,碱是氢氧化锂并且溶剂是水性1,2-二甲氧基乙烷。
具有式(A)的化合物可以使用已知程序,在溶剂(如水或醇的水溶液,如乙醇的水溶液)中,通过用高价碘试剂(如(二乙酰氧基)碘苯或亚碘酰苯)以及碱(如水性碳酸钠、氢氧化锂或氢氧化钠)进行处理由具有式(C)的1,3二酮化合物制备。
方案3
可替代地,丙炔基团可以稍后通过脱羧丙炔基化在合成序列中添加,如在以下步骤2中。
方案4
硼酸可以通过如以下方案5中的方法制备。例如,具有式(B)或(D)的化合物可以通过已知方法由具有式(F)或(H)的芳基卤制备。例如,可以在合适的溶剂(优选二***或四氢呋喃)中,在-80℃与30℃之间的温度下,用烷基锂卤化物或烷基镁卤化物处理具有式(F)或(H)的芳基卤,并且然后可以使获得的芳基镁或芳基锂试剂与硼酸三烷基酯(优选硼酸三甲酯)反应以得到硼酸芳基二烷基酯,可以使所述硼酸芳基二烷基酯在酸性条件下进行水解以提供具有式(B)或(D)的硼酸。
方案5
如以下方案中示出,具有式(I)的化合物还可以经由Pb偶联,通过使具有式(D)的化合物反应以形成具有式(J)的有机铅试剂并且随后在例如由J.Pinhey,Pure andAppl.Chem.[纯粹与应用化学],(1996),68(4),819和由M.Moloney等人,TetrahedronLett.[四面体快报],(2002),43,3407描述的条件下与1,3二酮(C)反应来制备。合适的三芳基铋化合物在例如由A.Yu.Fedorov等人,Russ.Chem.Bull.Int.Ed.[俄罗斯化学公报国际版],(2005),54(11),2602,和由P.Koech和M.Krische,J.Am.Chem.Soc.[美国化学会志],(2004),126(17),5350以及其中的参考文献描述的条件下可以用作相关程序。
方案6
如以下方案中示出,类型(I)的化合物还可以经由钯偶联制备,其中类型(B)的硼酸以铃木(Suzuki)类型偶联而偶联至适当保护的类型(K)的卤代烯烃。
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方案7
在合适的条件下,合适的1,3二酮还可以在钯催化下直接偶联至卤代化合物(例如具有式(L))。如前所述,中间体(M)的丙炔基化得到类型(I)的化合物。
方案8
具有式(I,G=H)的化合物可以通过与由T.Wheeler,US4,209,532描述的方法类似的方法,通过使具有式(N)的化合物(其中R是氢或烷基)优选地在酸或碱的存在下并且任选地在合适溶剂的存在下环化来制备。具有式(N)的化合物已经被特别设计为合成具有式(I)的化合物的中间体。具有式(N)的化合物(其中R是氢)可以在酸性条件下、优选地在强酸(如硫酸、多磷酸或伊顿试剂(Eaton’sreagent))的存在下、任选地在合适溶剂(如乙酸、甲苯或二氯甲烷)的存在下被环化。
方案9
如以下方案中示出,类型(I)的化合物还可以使用合适的保护基团通过后期官能化制备。化合物(Q)可以通过所述方法转化为中间体(R,G=H或烷基),并且然后可以除去N-保护基团(如示出的BOC基团)(在此实例中在酸性条件下)。
然后,中间体(S)可以通过在标准文献条件下与合适的活性酸(如酰基氯或PFP酯)偶联直接转化为类型(V,G=H或烷基)的化合物。可替代地,类型(S)的中间体可以在标准的酰胺偶联条件(如HATU)下与合适的酸反应以得到类型(U)或(T)的中间体。为了得到类型(V)或(W)的化合物(其中G=H或烷基),可以使中间体(U)和(T)与适当的O-取代的羟胺衍生物(在(V)和(W)的情况下是O-甲基羟胺)在标准条件下反应。通过先前描述的方法,可以容易地将类型(V)和(W)的化合物转化为类型(V和W,G不是H)的化合物。
方案10
当O-取代的羟胺不容易获得时,得到类型(V)和(W)的化合物(例如对于化合物(Y)(G=H))的可替代路径涉及通过使羟胺与中间体(T)(G=烷基)缩聚形成肟(X)(G=烷基),并且然后在碱性条件下置换烷基卤(在此实例中是4-溴四氢吡喃)以得到(Y)(G=烷基)。通过用酸(如HCl)处理可以将类型(Y)(G=烷基)的化合物转化为类型(Y)(G=H)的化合物。
方案11
类型(Z)的腙可以通过与方案10和11中相同的方法,通过用N-取代的肼(在此实例中是二甲基肼)代替O-取代的羟胺衍生物来合成。
方案12
可以使用如以下示出的方法制备如这些的1,3二酮。所以可商购的酮(例如类型(AA)的)可转化为中间体(AB),并且然后转化为中间体(AC),并且最后脱羧得到中间体(Q)(这些方法描述于WO2008/110308中)。
方案13
以下非限制性实例提供了用于本发明的代表性化合物(如下表1中所提及的)的具体合成方法。
实例1:9-(2,6-二甲基-4-丙-1-炔基-苯基)-3-(2-甲氧基亚氨基丙酰基)-3-氮杂螺[5.5]十一烷-8,10-二酮(化合物A1)的合成。
步骤1:O3-叔丁基O11-乙基8,10-二氧代-3-氮杂螺[5.5]十一烷-3,11-二甲酸酯的合成
将4-亚丙酮基哌啶-1-甲酸叔丁酯(12.9g,54.0mmol)溶解在乙醇(100mL)中并添加丙二酸二乙酯(54.12mmol)。将反应混合物用乙醇钠的溶液处理,所述溶液是通过在室温下将钠(54.1mmol)添加到乙醇(30ml)中制备的。将反应混合物在室温下搅拌3小时,然后加热至回流持续1小时。冷却后,将反应混合物在真空中浓缩,以得到呈油状物的O3-叔丁基O11-乙基8,10-二氧代-3-氮杂螺[5.5]十一烷-3,11-二甲酸酯,将其不经进一步纯化而用于下一步骤。
步骤2:8,10-二氧代-3-氮杂螺[5.5]十一烷-3-甲酸叔丁酯的合成
将来自步骤1的粗O3-叔丁基O11-乙基8,10-二氧代-3-氮杂螺[5.5]十一烷-3,11-二甲酸酯溶解在水性NaOH(12M,5mL)中并搅拌5小时。通过在0℃下添加浓HCl将反应混合物酸化至pH 6并用EtOAc萃取。将有机物干燥并在真空中浓缩以留下黄色固体,将其研磨产生8,10-二氧代-3-氮杂螺[5.5]十一烷-3-甲酸叔丁酯的淡粉色粉末。通过添加浓HCl将水层进一步酸化至pH 2并用EtOAc萃取。将有机物干燥并在真空中浓缩以留下淡黄色固体,将其用***研磨得到另一份8,10-二氧代-3-氮杂螺[5.5]十一烷-3-甲酸叔丁酯的淡黄色粉末(3.914g,13.91mmol)。1H NMR(400MHz,CDCl3)3.51-3.25(m,6H),2.69-2.54(m,4H),1.47-1.43(m,9H),1.44-1.39(m,4H)。
步骤3:9-(4-溴-2,6-二甲基-苯基)-8,10-二氧代-3-氮杂螺[5.5]十一烷-3-甲酸叔丁酯的合成
将8,10-二氧代-3-氮杂螺[5.5]十一烷-3-甲酸叔丁酯(0.5g,1.8mmol)和DMAP(1.1g,8.9mmol)溶解在氯仿(20mL)中。在氮气下将反应混合物搅拌10分钟并添加甲苯(5mL),然后添加[二乙酰氧基-(4-溴-2,6-二甲基-苯基)铅烷基]乙酸酯(1.2g,2.1mmol)。在氮气下在75℃下将所得悬浮液加热3小时,并且然后使其冷却至室温。将反应混合物用2MHCl(50mL)处理并在搅拌下形成白色沉淀物。将混合物过滤并将有机相分离,并将水层用DCM萃取。将合并的有机物干燥(MgSO4),蒸发并通过快速柱色谱法(梯度洗脱:5%-100%EtOAc:异己烷)纯化,以得到9-(4-溴-2,6-二甲基-苯基)-8,10-二氧代-3-氮杂螺[5.5]十一烷-3-甲酸叔丁酯(0.51g,1.1mmol)。1H NMR(400MHz,CD3OD)7.25-7.10(m,2H),3.54-3.43(m,4H),2.61-2.52(m,4H),2.05-1.98(m,6H),1.72-1.56(m,4H),1.48-1.39(m,9H)。
步骤4:9-(2,6-二甲基-4-丙-1-炔基-苯基)-8,10-二氧代-3-氮杂螺[5.5]十一烷-3-甲酸叔丁酯的合成。
将4-二苯基膦基丁基(二苯基)磷烷(32mg,0.075mmol)、二氯双(三苯基膦)钯(II)(26mg,0.0373mmol)和丁-2-炔酸(346mg,0.894mmol)放入微波小瓶中。添加9-(4-溴-2,6-二甲基-苯基)-8,10-二氧代-3-氮杂螺[5.5]十一烷-3-甲酸叔丁酯(0.346g,0.745mmol)在DMSO(6mL/mmol)中的溶液,然后添加DBU(0.34g,2.24mmol)并将反应混合物在110℃下在微波辐射下加热45分钟。将反应物用2MHCl稀释并用DCM萃取。将有机物干燥并在真空中浓缩以留下橙色胶状物,将其通过快速色谱法(梯度洗脱:在异己烷中的10%-100%EtOAc)纯化,以得到9-(2,6-二甲基-4-丙-1-炔基-苯基)-8,10-二氧代-3-氮杂螺[5.5]十一烷-3-甲酸叔丁酯(0.193g,0.456mmol)。1H NMR(400MHz,CD3OD)7.07-6.93(m,2H),3.52-3.45(m,4H),2.62-2.53(m,4H),2.02-1.98(m,9H),1.70-1.60(m,4H),1.51-1.42(m,9H)。
步骤5:9-(2,6-二甲基-4-丙-1-炔基-苯基)-3-氮杂螺[5.5]十一烷-8,10-二酮盐酸盐的合成。
将9-(2,6-二甲基-4-丙-1-炔基-苯基)-8,10-二氧代-3-氮杂螺[5.5]十一烷-3-甲酸叔丁酯(0.193g,0.456mmol)在室温下在1,4-二噁烷中的4M HCl(4mL,16mmol)中搅拌1小时。将反应混合物在真空中浓缩以留下呈白色固体的9-(2,6-二甲基-4-丙-1-炔基-苯基)-3-氮杂螺[5.5]十一烷-8,10-二酮盐酸盐,将其不经进一步纯化而直接用于下一反应。
步骤6:9-(2,6-二甲基-4-丙-1-炔基-苯基)-3-(2-氧代丙酰基)-3-氮杂螺[5.5]十一烷-8,10-二酮的合成
在室温下向2-氧代丙酸(0.049g,0.56mmol)在DCM(3mL)中的搅拌溶液中添加HATU(0.23g,0.61mmol),并且将混合物搅拌1h。然后,将9-(2,6-二甲基-4-丙-1-炔基-苯基)-3-氮杂螺[5.5]十一烷-8,10-二酮;盐酸盐(200mg,0.56mmol)、接着是N,N-二乙基乙胺(0.15mL,1.11mmol)添加到混合物中,将其在室温下搅拌过夜。将反应物用2M HCl稀释,用二氯甲烷萃取,并且将有机层直接负载到硅胶上并使用柱色谱法
(在异己烷中的80%-100%EtOAc)纯化以得到呈白色固体的9-(2,6-二甲基-4-丙-1-炔基-苯基)-3-(2-氧代丙酰基)-3-氮杂螺[5.5]十一烷-8,10-二酮(0.16g,60%)。
1H NMR(400MHz,甲醇)δ=7.06-7.01(m,2H),3.68-3.61(m,2H),3.52-3.46(m,2H),2.64(br s,4H),2.40-2.37(m,3H),2.01-2.00(m,6H),2.00-1.98(m,3H),1.77-1.70(m,4H)
步骤7:9-(2,6-二甲基-4-丙-1-炔基-苯基)-3-(2-甲氧基亚氨基丙酰基)-3-氮杂螺[5.5]十一烷-8,10-二酮(化合物A1)的合成。
在0℃下,向9-(2,6-二甲基-4-丙-1-炔基-苯基)-3-(2-氧代丙酰基)-3-氮杂螺[5.5]十一烷-8,10-二酮(39mg,0.101mmol)在DCM(0.5mL)中的搅拌溶液中添加吡啶(0.32mL,0.40mmol),然后添加O-甲基羟胺盐酸盐(9mg,0.11mmol),并将混合物缓慢温热至室温过夜。将反应混合物通过HyFlow过滤,用DCM洗涤,并在真空中除去挥发物。将材料通过快速柱色谱法(用在DCM中的0%-50%MeOH洗脱)纯化以得到呈白色泡沫的9-(2,6-二甲基-4-丙-1-炔基-苯基)-3-(2-甲氧基亚氨基丙酰基)-3-氮杂螺[5.5]十一烷-8,10-二酮(37mg,80%)(肟几何异构体的比率为2:1,E/Z未指定)。
1H NMR(400MHz,甲醇)δ=7.07-7.00(m,2H),3.93-3.89(m,1H),3.86-3.80(m,2H),3.76-3.35(m,4H),2.64-2.57(m,4H),2.12-1.88(m,12H),1.77-1.66(m,4H)
对几何异构体的说明:如通过NMR和LC-MS观察到的,以下实例中的多个存在几何异构体的混合物。在这些情况下,化合物绘制有肟的交叉键。在主要异构体>90%的情况下,这些化合物以主要异构体绘制。
实例2:9-(2,6-二甲基-4-丙-1-炔基-苯基)-3-[(2E)-2-甲氧基亚氨基乙酰基]-3-氮杂螺[5.5]十一烷-8,10-二酮(化合物A3)的合成。
在0℃下,向(2E)-2-甲氧基亚氨基乙酸(75mg,0.73mmol)在DCM(3.5mL)中的搅拌溶液中添加EDCI(0.126g,0.65mmol)然后添加2,3,4,5,6-五氟苯酚(0.121g,0.65mmol),并且将混合物在室温下搅拌过夜。将9-(2,6-二甲基-4-丙-1-炔基-苯基)-3-氮杂螺[5.5]十一烷-8,10-二酮;盐酸盐(262mg,0.73mmol)、接着是N,N-二乙基乙胺(0.15mL,1.09mmol)添加到混合物中,将其在室温下搅拌过夜。将反应物直接干负载到硅胶上并且使用柱色谱法(在DCM中的0%-10%MeOH)纯化以得到呈白色固体的9-(2,6-二甲基-4-丙-1-炔基-苯基)-3-[(2E)-2-甲氧基亚氨基乙酰基]-3-氮杂螺[5.5]十一烷-8,10-二酮(216mg,73%)。
1H NMR(400MHz,甲醇)δ=7.86(s,1H),7.03(s,2H),3.95(s,3H),3.76-3.64(m,4H),2.61(s,4H),2.02(s,6H),1.99(s,3H),1.78-1.67(m,4H)。
实例3:9-(2,6-二甲基-4-丙-1-炔基-苯基)-3-[(2E)-2-(2-吡啶基氧基亚氨基)丙酰基]-3-氮杂螺[5.5]十一烷-8,10-二酮(化合物A6)的合成
将9-(2,6-二甲基-4-丙-1-炔基-苯基)-3-(2-氧代丙酰基)-3-氮杂螺[5.5]十一烷-8,10-二酮(200mg,0.508mmol)悬浮在乙醇(2mL)中。添加吡啶(126μL,1.53mmol)并搅拌5分钟。然后添加O-(2-吡啶基)羟胺(112mg,1.0172mmol)在乙醇(1mL)中的溶液并搅拌5分钟。添加DCM(2mL)并且将反应物加热至回流持续3小时,然后在120℃下微波辐射2小时。在真空下除去溶剂,并且将残余物在水与DCM:MeOH(90:10)之间分配,然后使有机萃取物通过相分离筒。在真空下将溶剂从滤液中除去。将残余物通过快速色谱法(用在DCM中的1%-15%MeOH洗脱)纯化以得到呈白色固体的9-(2,6-二甲基-4-丙-1-炔基-苯基)-3-[(2E)-2-(2-吡啶基氧基亚氨基)丙酰基]-3-氮杂螺[5.5]十一烷-8,10-二酮(22mg,9%)。1H NMR(400MHz,甲醇)δppm 1.65-1.91(m,4H)1.94-2.00(m,9H)2.00-2.04(m,4H)2.24(s,3H)2.55-2.70(m,4H)3.39-3.54(m,2H)3.61-3.72(m,1H)3.79-3.89(m,1H)7.02(d,J=5.99Hz,2H)7.13(ddd,J=7.21,5.01,0.73Hz,1H)7.33(d,J=8.44Hz,1H)7.86(ddd,J=8.62,7.03,1.96Hz,1H)8.17-8.20(m,1H)。
实例4:3-[2-(二甲基亚肼基)丙酰基]-9-(2,6-二甲基-4-丙-1-炔基-苯基)-3-氮杂螺[5.5]十一烷-8,10-二酮(化合物A8)的合成
将9-(2,6-二甲基-4-丙-1-炔基-苯基)-3-(2-氧代丙酰基)-3-氮杂螺[5.5]十一烷-8,10-二酮(31mg,0.080mmol)溶解在MeOH(0.5mL)中并冷却至0℃。一次性添加1,1-二甲基肼(6.7μL,0.086mmol)并且然后将反应物在室温下搅拌48小时。添加在二噁烷中的4MHCl(1.8μL),并且然后在真空下将溶剂除去。将残余物通过快速色谱法(在DCM中的1%-15%MeOH)纯化以得到呈灰白色固体的3-[2-(二甲基亚肼基)丙酰基]-9-(2,6-二甲基-4-丙-1-炔基-苯基)-3-氮杂螺[5.5]十一烷-8,10-二酮(30mg,81%)以及大约1:1的几何异构体的混合物。1H NMR(400MHz,甲醇)δppm 1.73(br d,J=3.91Hz,4H)1.97-2.04(m,9H)2.07-2.13(m,3H),2.47(s,3H)2.57(s,3H),2.61(s,4H),3.33-3.42(m,1H)3.50-3.59(m,1H)3.62-3.74(m,2H)7.03(s,2H)。
本发明的除草化合物的实例。
表1
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生物学实例
将各种测试物种的种子播种在盆内的标准土壤中(多年生黑麦草(Loliumperenne)(LOLPE)、大狗尾草(Setaria faberi)(SETFA)、大穗看麦娘(Alopecurusmyosuroides)(ALOMY)、稗草(Echinochloa crus-galli)(ECHCG)、野燕麦(Avena fatua)(AVEFA))。在温室中在受控条件(在24℃/16℃白天/夜晚下;14小时光照;65%湿度)下培养一天后(出苗前)或八天培养后(出苗后),用水性喷雾溶液喷洒这些植物,该水性喷雾溶液源自工业级活性成分在丙酮/水(50:50)溶液中的配制品,该溶液含有0.5%吐温20(聚氧乙烯脱水山梨糖醇单月桂酸酯,CAS RN 9005-64-5)。化合物以250g/h施用。然后使测试植物在温室中在受控条件(在24℃/16℃白天/夜晚下;14小时光照;65%湿度)下生长,并且每天浇水两次。13天后对于出苗前和出苗后,评估测试对植物造成的损害百分比。下表中以五分制示出了生物活性(5=80%-100%;4=60%-79%;3=40%-59%;2=20%-39%;1=0%-19%)。NT=未测试。
表B1:出苗前施用
化合物 | 比率(g/Ha) | ALOMY | AVEFA | ECHCG | LOLPE | SETFA |
A1 | 250 | 5 | 5 | 5 | 5 | 5 |
A2 | 250 | 5 | 5 | 5 | 5 | 5 |
A3 | 250 | 4 | 5 | 5 | 5 | 5 |
A4 | 250 | 5 | 5 | 5 | 5 | 5 |
A5 | 250 | 4 | 5 | 5 | 5 | 5 |
A6 | 250 | 5 | 5 | 5 | 5 | 5 |
A7 | 250 | 4 | 2 | 5 | 5 | 5 |
A8 | 250 | 5 | 5 | 5 | 5 | 5 |
A9 | 250 | 5 | 2 | 3 | 3 | 4 |
A10 | 250 | 4 | 1 | 4 | 1 | 4 |
A11 | 250 | 5 | 3 | 5 | 5 | 5 |
表B2:出苗后施用
对照
使用以上程序概述,将小麦和大麦作物植物在出苗后用本发明的化合物A1、A3或A8或比较化合物C1(来自WO 2014/096289的化合物A-38)以指示的施用比率进行处理。这些化合物还与50g/ha的安全剂化合物解毒喹(CQC)一起施用。
表B3.
化合物 | 比率g/ha | 小麦 | 大麦 |
A1 | 30 | 10 | 20 |
60 | 20 | 40 | |
60+CQC | 0 | - | |
A3 | 30 | 0 | 0 |
60 | 20 | 30 | |
60+CQC | 0 | - | |
A8 | 30 | 0 | 0 |
60 | 10 | 0 | |
60+CQC | 10 | - | |
C1 | 30 | 40 | 80 |
60 | 70 | 90 | |
60+CQC | 60 | - |
在上表B3中概述的结果示出了观察到的%植物毒性,并且与现有技术的化合物C1相比,本发明的化合物A1、A3和A8对小麦和大麦作物的损害明显更小。
Claims (12)
1.一种具有式(I)的化合物
其中
R1是1-丙炔基;
R2是甲基;
R3是甲基;
R4是-C(O)C(R5)=N-O-R6或-C(O)C(R5)=N-NR7R8;
R5选自由以下组成的组:氢、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基-和C1-C6卤代烷氧基;
R6选自由以下组成的组:氢、C1-C6烷基、C1-C6烷氧基C1-C3烷基-、C3-C6环烷基、-CH2CN、四氢吡喃基-、苯基和-吡啶基;
R7是氢或C1-C6烷基;
R8是氢或C1-C6烷基;
G选自由以下组成的组:氢、-C(O)C1-C6烷基和-C(O)-O-C1-C6烷基;
或其农业上可接受的盐。
2.根据权利要求1所述的化合物,其中,R5是甲基。
3.根据权利要求1所述的化合物,其中,R4是-C(O)C(R5)=N-O-R6。
4.根据权利要求1所述的化合物,其中,R6是甲基。
5.根据权利要求1所述的化合物,其中,G是氢。
6.根据权利要求1所述的化合物,其中,G是-C(O)C1-C6烷基。
7.根据权利要求1所述的化合物,其中,G是-C(O)-O-C1-C6烷基。
8.一种除草组合物,其包含根据权利要求1至7中任一项所述的具有式(I)的化合物和农业上可接受的配制辅助剂。
9.根据权利要求8所述的除草组合物,其进一步包含至少一种另外的杀有害生物剂。
10.根据权利要求9所述的除草组合物,其中,所述另外的杀有害生物剂是除草剂或除草剂安全剂。
11.一种在场所处控制杂草的方法,所述方法包括向所述场所施用控制杂草量的根据权利要求8至10中任一项所述的组合物。
12.根据权利要求1所述的具有式(I)的化合物作为除草剂的用途。
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