CN111788190A - 具有除草活性的马来酰亚胺衍生物、其农用组合物及其用途 - Google Patents
具有除草活性的马来酰亚胺衍生物、其农用组合物及其用途 Download PDFInfo
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- CN111788190A CN111788190A CN201980009443.8A CN201980009443A CN111788190A CN 111788190 A CN111788190 A CN 111788190A CN 201980009443 A CN201980009443 A CN 201980009443A CN 111788190 A CN111788190 A CN 111788190A
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- MFSWTRQUCLNFOM-UHFFFAOYSA-N methyl 2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoate Chemical group C1=CC(OC(C)C(=O)OC)=CC=C1OC1=NC=C(C(F)(F)F)C=C1Cl MFSWTRQUCLNFOM-UHFFFAOYSA-N 0.000 description 1
- BACHBFVBHLGWSL-UHFFFAOYSA-N methyl 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoate Chemical group C1=CC(OC(C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-UHFFFAOYSA-N 0.000 description 1
- IAUMNRCGDHLAMJ-UHFFFAOYSA-N methyl 2-[4-[5-(trifluoromethyl)pyridin-2-yl]oxyphenoxy]propanoate Chemical group C1=CC(OC(C)C(=O)OC)=CC=C1OC1=CC=C(C(F)(F)F)C=N1 IAUMNRCGDHLAMJ-UHFFFAOYSA-N 0.000 description 1
- QPTPZPIXUPELRM-UHFFFAOYSA-N methyl 3-[2-[2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenyl]sulfanylpropanoylamino]propanoate Chemical compound C1=C(Cl)C(SC(C)C(=O)NCCC(=O)OC)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1F QPTPZPIXUPELRM-UHFFFAOYSA-N 0.000 description 1
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- GLBLPMUBLHYFCW-UHFFFAOYSA-N n-(5,7-dimethoxy-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)-2-methoxy-4-(trifluoromethyl)pyridine-3-sulfonamide Chemical compound N1=C2N=C(OC)C=C(OC)N2N=C1NS(=O)(=O)C1=C(OC)N=CC=C1C(F)(F)F GLBLPMUBLHYFCW-UHFFFAOYSA-N 0.000 description 1
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- 230000003287 optical effect Effects 0.000 description 1
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- UCDPMNSCCRBWIC-UHFFFAOYSA-N orthosulfamuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)NC=2C(=CC=CC=2)C(=O)N(C)C)=N1 UCDPMNSCCRBWIC-UHFFFAOYSA-N 0.000 description 1
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- 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
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- 239000012071 phase Substances 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
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- 239000002243 precursor Substances 0.000 description 1
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- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
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- 125000006239 protecting group Chemical group 0.000 description 1
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- USSIUIGPBLPCDF-KEBDBYFISA-N pyriminobac-methyl Chemical group CO\N=C(/C)C1=CC=CC(OC=2N=C(OC)C=C(OC)N=2)=C1C(=O)OC USSIUIGPBLPCDF-KEBDBYFISA-N 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
- VIXWGKYSYIBATJ-UHFFFAOYSA-N pyrrol-2-one Chemical compound O=C1C=CC=N1 VIXWGKYSYIBATJ-UHFFFAOYSA-N 0.000 description 1
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- FFSSWMQPCJRCRV-UHFFFAOYSA-N quinclorac Chemical compound ClC1=CN=C2C(C(=O)O)=C(Cl)C=CC2=C1 FFSSWMQPCJRCRV-UHFFFAOYSA-N 0.000 description 1
- OSUHJPCHFDQAIT-GFCCVEGCSA-N quizalofop-P-ethyl Chemical group C1=CC(O[C@H](C)C(=O)OCC)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 OSUHJPCHFDQAIT-GFCCVEGCSA-N 0.000 description 1
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- 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
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- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- ZDXMLEQEMNLCQG-UHFFFAOYSA-N sulfometuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=CC(C)=N1 ZDXMLEQEMNLCQG-UHFFFAOYSA-N 0.000 description 1
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- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- IUQAXCIUEPFPSF-UHFFFAOYSA-N tembotrione Chemical compound ClC1=C(COCC(F)(F)F)C(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O IUQAXCIUEPFPSF-UHFFFAOYSA-N 0.000 description 1
- BCQMBFHBDZVHKU-UHFFFAOYSA-N terbumeton Chemical compound CCNC1=NC(NC(C)(C)C)=NC(OC)=N1 BCQMBFHBDZVHKU-UHFFFAOYSA-N 0.000 description 1
- IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 0.000 description 1
- FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- GLDAZAQRGCSFNP-UHFFFAOYSA-N thiencarbazone Chemical compound O=C1N(C)C(OC)=NN1C(=O)NS(=O)(=O)C1=C(C)SC=C1C(O)=O GLDAZAQRGCSFNP-UHFFFAOYSA-N 0.000 description 1
- AHTPATJNIAFOLR-UHFFFAOYSA-N thifensulfuron-methyl Chemical group S1C=CC(S(=O)(=O)NC(=O)NC=2N=C(OC)N=C(C)N=2)=C1C(=O)OC AHTPATJNIAFOLR-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 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
- IMEVJVISCHQJRM-UHFFFAOYSA-N triflusulfuron-methyl Chemical group COC(=O)C1=CC=CC(C)=C1S(=O)(=O)NC(=O)NC1=NC(OCC(F)(F)F)=NC(N(C)C)=N1 IMEVJVISCHQJRM-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
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- 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
- A01N43/80—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 five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—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
- A01N43/74—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 five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—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
- A01N43/74—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 five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
-
- 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
- A01N43/82—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 five-membered rings with three ring hetero atoms
-
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0814—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring is substituted at a C ring atom by Si
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
Abstract
本发明涉及具有通式(I)的新的马来酰亚胺:
Description
本发明涉及具有通式(I)的新的马来酰亚胺、其异构体、盐和水合物:
以及它们作为除草剂的用途。
发明内容
本发明涉及新的取代的马来酰亚胺。
更具体地,本发明涉及具有高除草活性的新的取代的马来酰亚胺及其作为除草剂在农作物中控制杂草的用途。
专利申请EP297378、US4,845,230和更近的WO2016/071360描述了用作除草剂的具有以下通式的羟基马来酰亚胺:
此外,例如在专利申请EP286816、EP339390或WO2014/180740中已经描述了其中羟基被适当酰化的马来酰亚胺。
然而,上述专利申请中指出的使用剂量极高,因此除了对所处理农作物造成植物毒性外,还可能产生与环境影响有关的问题。
申请人现已出人意料地发现,通过适当修饰存在于马来酰亚胺环上的取代基,可获得具有显著除草活性的产品,其具有对多种杂草的显著除草活性,并且使用剂量显著降低。同时,这些产品对具有农业意义的农作物表现出低的或没有植物毒性,因此也可用作选择性除草剂。
因此,本发明的目的涉及具有通式(I)的新的马来酰亚胺:
其中
-R代表C3-C18环烷基羰基,C3-C18环烷基硫羰基,C7-C12烷基羰基,C3-C18环烷氧基羰基,C3-C18环烷基C1-C6烷基羰基,C3-C18环烷基C1-C12烷基硫羰基,C1-C12烷氧基C1-C12烷基羰基,C1-C12烷氧基C1-C12烷基硫羰基,C3-C18环烷氧基C1-C12烷基羰基,C3-C18环烷氧基C1-C12烷基硫羰基,C1-C12烷硫基C1-C12烷基羰基,C3-C18环烷基硫C1-C12烷基羰基,C1-C12烷基羧基C1-C12烷基羰基,C3-C18环烷基羧基C1-C12烷基羰基,C1-C12烷基羰基C1-C12烷基羰基,C3-C18环烷基羰基C1-C12烷基羰基,C1-C12烷氧基C1-C12烷氧基羰基,C3-C18环烷氧基C1-C12烷氧基羰基,C1-C12烷硫基C1-C12烷氧基羰基,C3-C18环烷硫基C1-C12烷氧基羰基,C3-C18环烷基羧基C1-C12烷氧基羰基,芳基C1-C12烷氧基羰基,C1-C12烷氧基C2-C12烷基,芳氧基C1-C12烷基,苄氧基C2-C12烷基,C3-C18环烷氧基C1-C12烷基,C1-C12烷基羧基C1-C12烷基,C3-C18环烷基羧基C1-C12烷基,C1-C12烷硫基C1-C12烷基,C3-C18环烷硫基C1-C12烷基,C1-C12烷基羰基C1-C12烷基,C3-C18环烷基羰基C1-C12烷基,C1-C12烷氧基羰基C1-C12烷基,C3-C18环烷氧基羰基C1-C12烷基,C2-C6卤代链烯基羰基,R3R4R5Si基团,CO-COOR3基团,COCR3 2COOR3基团,双官能团-SiR3R4(CH2)mSiR3R4-基团,双官能团-(CO-CO)-基团,双官能团-(COCR3 2CO)-基团,双官能团-[COO(CH2)mOCO]-基团;
-R1和R2彼此相同或不同,表示卤原子,C1-C12烷基,C1-C12卤代烷基,C3-C18环烷基,C1-C12烷氧基,C3-C18环烷氧基。
-Z表示O原子,S原子或NR4基团;
-Q表示O原子,S原子,NOR3基团,NR3R4基团,C=CR3R4基团;
-R3,R4,R5彼此相同或不同,表示氢原子,C1-C12烷基,C1-C12卤代烷基,C3-C18环烷基;
-m是1至5的整数;
-n为1或2;
-G表示5或6元的芳香族杂环,其选自:
并且其中:
-X表示氮原子或CRa基团;
-W表示氧原子,或硫原子或NRa基团;
-Ra,Rb,Rc彼此相同或不同,表示氢原子,卤素原子,C1-C12烷基,C2-C12烯基,C2-C12卤代烯基,C3-C18环烯基,C3-C18环烷基,C2-C12炔基,C1-C12卤代烷基,C1-C12烷氧基,C1-C12卤代烷氧基,C3-C18环烷氧基,CN基,B(OR3)2基,4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷基(dioxaborolanyl);
条件是,当:
(i)R表示环丙基羰基,环己基羰基或3-酮丁酰基,并且
(ii)R1和R2均为甲基,并且
(iii)Q和Z为氧原子,且
(iv)n等于1时,
那么G不同于其中Ra和Rb都是氢或其中Ra是甲基并且Rb是氢的G6。
优选式(I)的化合物,其中:
-R表示C3-C12环烷基羰基,C3-C12环烷基硫羰基,C7-C12烷基羰基,C3-C12环烷氧基羰基,C3-C12环烷基C1-C6烷基羰基,C3-C12环烷基C1-C6烷基硫羰基,C1-C6烷氧基C1-C6烷基羰基,C1-C6烷氧基C1-C6烷基硫羰基,C3-C12环烷氧基C1-C6烷基羰基,C3-C12环烷氧基C1-C6烷基硫羰基,C1-C6烷硫基C1-C6烷基羰基,C3-C12环烷硫基C1-C6烷基羰基,C1-C6烷基羧基C1-C6烷基羰基,C3-C12环烷基羧基C1-C6烷基羰基,C1-C6烷基羰基C1-C6烷基羰基,C3-C12环烷基羰基C1-C6烷基羰基,C1-C6烷氧基C1-C6烷氧基羰基,C3-C12环烷氧基C1-C6烷氧基羰基,C1-C6烷硫基C1-C6烷氧基羰基,C3-C12环烷硫基C1-C6烷氧基羰基,C3-C12环烷基羧基C1-C6烷氧基羰基,芳基C1-C6烷氧基羰基,C1-C6烷氧基C2-C7烷基基团,芳氧基C1-C6烷基,苄氧基C2-C7烷基,C3-C12环烷氧基C1-C6烷基,C1-C6烷基羧基C1-C6烷基,C3-C12环烷基羧基C1-C6烷基,C1-C6烷硫基C1-C6烷基,C3-C12环烷硫基C1-C6烷基,C1-C6烷基羰基C1-C6烷基,C3-C12环烷基羰基C1-C6烷基,C1-C12烷氧基羰基C1-C12烷基,C3-C12环烷氧基羰基C1-C12烷基,C2-C6卤代烯基羰基,R3R4R5Si基,CO-COOR3基团,COCR3 2COOR3基团,双官能团-SiR3R4(CH2)mSiR3R4-基团,双官能团-(CO-CO)-基团,双官能团-(COCR3 2CO)-基团,双官能团-[COO(CH2)mOCO]-基团;
-R1和R2彼此相同或不同,表示卤原子,C1-C6烷基,C1-C6卤代烷基,C3-C12环烷基,C1-C6烷氧基,C3-C12环烷氧基;
-Z表示O原子,S原子或NR4基团;
-Q表示O原子,S原子,NOR3基团,NR3R4基团,C=CR3R4基团;
-R3,R4,R5彼此相同或不同,表示氢原子,C1-C6烷基,C1-C6卤代烷基,C3-C12环烷基;
-m是1至5的整数;
-n为1或2;
-G表示5或6元的芳香族杂环,其选自:
并且其中:
-X表示氮原子或CRa基团;
-W表示氧原子,或硫原子或NRa基团;
-Ra,Rb,Rc彼此相同或不同,表示氢原子,卤素原子,C1-C6烷基,C2-C7烯基,C2-C7卤代烯基,C3-C12环烯基,C3-C12环烷基,C2-C7炔基,C1-C6卤代烷基,C1-C6烷氧基,C1-C6卤代烷氧基,C3-C12环烷氧基,CN基团,B(OR3)2基团,4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷基;
条件是,当:
(i)R表示环丙基羰基,环己基羰基或3-酮丁酰基,并且
(ii)R1和R2均为甲基,并且
(iii)Q和Z为氧原子,并且
(iv)n等于1时,
那么G不同于其中Ra和Rb都是氢或其中Ra是甲基并且Rb是氢的G6。
C7-C12烷基羰基是指具有式RxCO的基团,其中Rx具有C7-C12烷基的含义。
该基团的实例是庚烷羰基,辛烷羰基,壬烷羰基,癸烷羰基。
C1-C12烷氧基C1-C12烷基羰基,C3-C18环烷氧基C1-C12烷基羰基是指具有式RxORyCO的基团,其中Rx分别具有C1-C12烷基和C3-C18环烷基的含义,并且Ry具有C1-C12烷基的含义。
这些基团的实例是甲氧基甲基羰基,异丙氧基甲基羰基,环丙氧基甲基羰基,甲氧基乙基羰基,甲氧基丙基羰基。
C1-C12烷硫基C1-C12烷基羰基,C3-C18环烷硫基C1-C12烷基羰基是指具有式RxSRyCO的基团,其中Rx分别具有C1-C12烷基和C3-C18环烷基的含义,并且Ry具有C1-C12烷基的含义。
这些基团的实例是甲硫基甲基羰基,异丙基硫基甲基羰基,环丙基硫基甲基羰基。
C3-C18环烷基C1-C12烷基硫羰基是指具有式RxRyCS的基团,其中Rx分别具有C3-C18环烷基的含义,并且Ry具有C1-C12烷基的含义。
这些基团的实例是环丙基-甲基硫羰基,环己基甲基硫羰基。
C1-C12烷氧基C1-C12烷基硫羰基,C3-C18环烷氧基C1-C12烷基硫羰基是指具有式RxORyCS的基团,其中Rx具有C1-C12烷基和C3-C18环烷基的含义,并且Ry具有C1-C12烷基的含义。
这些基团的实例是甲氧基甲基硫羰基,异丙氧基甲基硫羰基,环丙氧基甲基硫羰基。
C1-C12烷基羧基C1-C12烷基羰基和C3-C18环烷基羧基C1-C12烷基羰基是指具有式RxOCORyCO的基团,其中Rx分别具有C1-C12烷基和C3-C18环烷基的含义,并且Ry具有C1-C12烷基的含义。
这些基团的实例是甲基羧甲基羰基,乙基羧甲基羰基,环己基羧甲基羰基。
C1-C12烷基羰基C1-C12烷基羰基和C3-C18环烷基羰基C1-C12烷基羰基是指具有式RxCORyCO的基团,其中Rx分别具有C1-C12烷基和C3-C18环烷基的含义,并且Ry具有C1-C12烷基的含义。
这些基团的实例是乙酰基甲基羰基,乙基羰基甲基羰基,环丙基羰基甲基羰基。
C1-C12烷氧基C1-C12烷氧基羰基和C3-C18环烷氧基C1-C12烷氧基羰基是指具有式RxORyOCO的基团,其中Rx分别具有C1-C12烷基和C3-C18环烷基的含义,并且Ry具有C1-C12烷基的含义。
这些基团的实例是甲氧基甲氧基羰基,乙氧基甲氧基羰基,环丙氧基甲氧基羰基。
C1-C12烷硫基C1-C12烷氧基羰基和C3-C18环烷硫基C1-C12烷氧基羰基是指具有式RxSRyCOO的基团,其中Rx分别是C1-C12烷基和C3-C18环烷基。
这些基团的实例是甲硫基甲氧基羰基,乙硫基甲氧基羰基,环丙基硫基甲氧基羰基。
C1-C12烷基羧基C1-C12烷氧基羰基和C3-C18环烷基羧基C1-C12烷氧基羰基是指具有式RxOCORyOCO的基团,其中Rx分别具有C1-C12烷基和C3-C18环烷基的含义,并且Ry具有C1-C12烷基的含义。。
这些基团的例子是甲基羧基甲氧基羰基,乙基羧基甲氧基羰基,环丙基羧基甲氧基羰基。
芳基C1-C12烷氧基羰基是指具有式ArRx OCO的基团,其中Rx分别是C1-C12烷基的含义,并且Ar具有单、双或三环芳族系统的含义,仅由碳原子组成。
这些基团的实例是苄氧羰基,2-苯氧羰基。
C1-C12烷氧基C2-C12烷基,芳氧基C1-C12烷基,苄氧基C2-C12烷基,C3-C18环烷氧基C1-C12烷基是指具有式RxORy的基团,其中Rx分别具有C1-C12烷基、芳基、苄基和C3-C18环烷基的含义,并且Ry具有C1-C12烷基的含义。
这些基团的实例是乙氧基甲基,2-苯氧基乙基,苄氧基甲基,环丙氧基甲基。
C1-C12烷基羧基C1-C12烷基和C3-C18环烷基羧基C1-C12烷基是指具有式RxOCORy的基团,其中Rx分别具有C1-C12烷基和C3-C18环烷基的含义,并且Ry具有C1-C12烷基的含义。
这些基团的实例是甲基羧甲基,环丙基羧甲基。
C1-C12烷硫基C1-C12烷基和C3-C18环烷硫基C1-C12烷基是指具有式RxSRy的基团,其中Rx分别具有C1-C12烷基和C3-C18环烷基的含义,并且Ry具有C1-C12烷基的含义。
这些基团的实例是甲硫基甲基,环丙基硫基甲基。
C1-C12烷基羰基C1-C12烷基和C3-C18环烷基羰基C1-C12烷基是指具有式RxCORy的基团,其中Rx分别具有C1-C12烷基和C3-C18环烷基的含义,并且Ry具有C1-C12烷基的含义。
这些基团的实例是乙酰甲基丙酰基甲基,环己酰基甲基。
C1-C12烷氧基羰基C1-C12烷基和C3-C18环烷氧基羰基C1-C12烷基是指具有式RxOCORy的基团,其中Rx分别具有C1-C12烷基和C3-C18环烷基的含义,并且Ry具有C1-C12烷基的含义。
这些基团的实例是甲氧基羰基甲基,异丙氧基羰基甲基,环戊氧基羰基甲基。
C2-C6卤代烯基羰基是指具有式RxCO的基团,其中Rx具有C2-C6卤代烯基的含义。
该组的实例是3,3-二氟-2-烯丙基羰基,2,2-二氟乙烯基羰基,4,4-二氟-3-丁烯羰基,5,5-二氟-4-戊烯羰基,6,6-二氟-5-己烯羰基。
卤素的实例是氟,氯,溴,碘。
C1-C12烷基的实例是甲基,乙基,正丙基,异丙基,正丁基,异丁基,仲丁基,叔丁基,正戊基,3-甲基丁基,正己基,3,3-二甲基丁基。
C1-C12卤代烷基的实例是氟甲基,二氟甲基,三氟甲基,氯甲基,二氯甲基,2,2,2-三氟乙基,1,1,2,2-四氟乙基,五氟乙基,七氟丙基,4,4,4-三氯丁基,4,4-二氟戊基,5,5-二氟己基。
C3-C18环烷基的实例是环丙基,环丁基,环戊基,环己基。
C2-C12烯基的实例为:乙烯基,丙烯基,丁烯基。
C2-C12卤代烯基的实例是:2,2-二氯丙烯基,1,2,2-三氯丙烯基。
C2-C12炔基的实例为炔丙基,2-丁炔基。
C3-C18环烷基羰基的实例是环丙酰基,环戊酰基。
C3-C18环烷基硫羰基的实例是环丙基硫代羰基,环戊基硫代羰基。
C3-C18环烷氧基羰基的实例是环丙氧基羰基,环己基氧基羰基。
C1-C12烷氧基的实例是甲氧基,乙氧基。
C1-C12卤代烷氧基的实例是三氟甲氧基,1,1,2,2-四氟乙氧基,1,1,2,3,3,3-六氟丙氧基。
C3-C18环烷基的实例是环丙氧基,环戊氧基。
R3R4R5Si基的实例分别是三甲基甲硅烷基,三乙基甲硅烷基,二甲基叔丁基甲硅烷基,二甲基-苯基甲硅烷基。
芳基是指仅由碳原子组成的单环、双环或三环芳族体系,例如:苯基,萘基,菲基,蒽基。
所有的芳基,苄基系统可以被一个或多个选自卤素,C1-C12烷基,C1-C12卤代烷基,C3-C18环烷基,C1-C12烷氧基,C4-C18环烷氧基,C1-C18卤代烷氧基的基团取代。
本发明还包括:
a)由取代基R,R1-R5,Ra,Rb,Rc,Z,Q和G的特定含义衍生的具有通式(I)的化合物的任何可能的立体异构体;
b)具有式(I)的化合物的盐,例如通过添加无机或有机酸获得的盐;
c)具有式(I)的化合物的任何可能的水合物。
具有除草活性的通式(I)化合物的具体实例为其中R,R1,R2,Z,n,Q和G具有表1所示含义的化合物:
表1
生物学活性方面优选的式(I)化合物是这些,其中:
-R表示选自C3-C12环烷基羰基,C1-C18烷氧基烷基羰基,C1-C18烷氧基C1-C18烷氧基羰基,R3R4R5Si基或-(COCO)-基团的基团,
-Z代表氧或硫原子,
-Q代表氧原子或NOH基团,
-R1和R2彼此相同表示C1-C4烷基,
-n等于1或2并且
-G选自G1至G6,并且代表含有至少一个选自氮、氧和硫的杂原子的六或五元杂环。
甚至更优选的是具有式(I)的化合物,其中:
-R表示选自环丙基羰基,甲氧基甲基羰基,甲氧基-乙氧基羰基,三甲基甲硅烷基或-(COCO)-的基团,
-R1和R2为甲基或乙基,
-Z和Q代表氧原子,
-n等于1或2并且
-G选自G1至G4,并且代表噻二唑基、异噁唑基或吡唑基。
特别优选的是具有通式(I)的化合物,其中R,R1,R2,Z,Q,G和n具有表2所示的含义。
表2
如本领域技术人员将清楚的,可以以两种或更多种旋光异构体的形式获得具有通式(I)的化合物。
因此,本发明的一个目的涉及外消旋形式、异构体纯的或其任意比例的混合物的通式(I)的化合物,其中所述混合物可能在制备通式(I)的化合物的过程中获得或得自相同异构体的不完全分离。
本发明的另一个目的涉及制备具有通式(I)的化合物的方法。
特别地,具有通式(I)的化合物可以由相应的具有式(II)的化合物通过用具有式(III)的化合物R-T将ZH基团官能化而制备,其中R具有如前所述的含义,如反应路线1所示。
路线1
更具体地,当n具有1或2的值时,该反应可以在合适的溶剂中,在有机或无机碱的存在下,用具有式(III)的化合物R-T来处理具有式(II)的化合物,其中在上述式(III)中,T代表离去基团,例如选自Cl、Br、I的卤素、或甲磺酸酯、对甲苯磺酸酯或三氟甲磺酸酯基团。具有式(III)的化合物可以如例如在Theodora W.Greene“有机合成中的保护基团”第三版第198-199页中所述获得。上述有机或无机碱例如可以是:三乙胺,吡啶,乙酸钠,氢化钠或氢化钾,碳酸氢钾或碳酸氢钙,氢氧化钠或氢氧化钾。上述溶剂可以例如是:二氯乙烷,氯仿或二氯甲烷,四氢呋喃。上述反应可以例如在0℃至所选择的溶剂的回流温度的温度下进行。
当Z和Q具有氧的含义时,具有式(II)的化合物可以通过如反应路线2所示还原相应的前体(IV)来制备,例如使用硼氢化钠或氢化铝锂作为还原剂,在合适的醇溶剂(例如甲醇,乙醇,丙醇,异丙醇)中或在卤代烃溶剂(例如二氯甲烷,二氯乙烷或氯仿)中或在醚如二噁烷或四氢呋喃中进行。
该反应可以方便地在0℃至室温的温度下进行1至12小时的时间。
路线2
当Z代表S原子或NR4基团且Q是氧时,具有式(II)的化合物可以从化合物(V)开始制备,其中T代表离去基团,例如选自Cl,Br,I的卤素,或甲磺酸酯,对甲苯磺酸酯或三氟甲磺酸酯基团,如反应路线3所述并如文献中所述,例如在EP0297378和EP0339390中所述,通过用具有式R4NH2的胺或盐(例如KSH或NaSH)取代。
路线3
或者,当Z代表氧原子时,具有通式(I)的化合物可以根据反应路线4通过具有通式(VI)的化合物(其中T代表离去基团,例如选自Cl,Br,I的卤素,或甲磺酸酯,对甲苯磺酸酯或三氟甲磺酸酯),与具有式(VII)的化合物R-ZH的反应获得。
路线4
反应可以在有机或无机碱(例如:三乙胺,吡啶,乙酸钠,氢化钠或氢化钾,碳酸氢钾或碳酸氢钙,氢氧化钠或氢氧化钾)的存在下,在合适的溶剂(例如,二氯乙烷,氯仿,二氯甲烷或四氢呋喃)中进行,温度范围为0℃至所选溶剂的回流温度,通常在0℃至90℃的范围内,例如在Plouvier,B等人,“Journal of Medicinal Chemistry”,2007年,第50卷,第2818-2841页或Campbell S.等人,“Journal of Medicinal Chemistry,1988,第31卷,第516-520页或在Kyasa S.等人,“Journal of Organic Chemistry”,2015年,第80卷,第12100-12114页中所述。
当Q和Z具有氧的含义时,具有式(IV)的化合物可以通过适当的马来酸酐(VIII)与具有式(IX)的化合物G-NH2(G具有G1-G6的含义)的反应来制备,在酸性环境(例如冰醋酸)中,在有或没有溶剂存在的情况下,在0℃至所用溶剂的回流温度的温度范围内,通常在0℃-90℃范围内的温度下进行,如反应流程5所示并且例如在EP0297378或EP0286816中所述。
路线5
或者,当Q和Z具有氧的含义时,具有通式(IV)的化合物可以通过适当的马来酰亚胺(X)与具有通式(XI)的化合物TG的反应获得,其中G具有G1-G6的含义和T是具有上述含义的离去基团,例如在Wolfe RMW等人,“Organic Letters”,2017年,第19卷,第996-999页,并根据反应路线6中所示进行。
路线6
或者,可以通过合适的羟基吡咯烷酮(XII)与通式(XI)的化合物TG反应获得通式(II)的化合物,其中Q和Z代表氧原子,其中T代表选自Cl,Br,I的卤素原子,和G具有G1-G6的含义,在过渡金属络合物(例如Pd2(dba)3(三(二苄叉基丙酮)二钯(0))或Pd(OAc)2(乙酸Pd(II))存在下,可能在配体例如Xantphos或Brettphos的存在下,在存在或不存在碱(例如碳酸钾或碳酸铯)的情况下并且在惰性溶剂(例如甲苯)中,如文献,例如,Yin J.等人,“Organic Letters”,第2卷,第8期,2000年,1101-1104中所述,根据反应路线7进行。
路线7
根据有机化学中众所周知的方法,可以容易地获得具有式(IV)的化合物,其中Q和Z具有氧的含义且R1和R2彼此不同并且具有卤素原子如Cl或Br含义,例如如WO2014180740中所述,根据反应路线8,使用Alg2作为反应试剂通过中间体(XIII)的卤化反应,其中Alg例如为Br或Cl。
路线8
当Q和Z具有氧的含义并且当R1和R2不同于卤素原子时,具有式(II)的羟基吡咯烷酮可以通过将具有式(IX)的化合物G-NH2(G具有G1-G6的含义)用具有式(XV)的化合物酰化而得到---后者又由式(XIV)的化合物获得,通过文献中已知的反应得到式(XVI)的化合物。然后可以将式(XVI)的化合物在具有通式(XVII)的化合物存在下通过Horner-Wadsworth-Emmons反应转化为中间体(XVIIIa)和(XVIIIb),其在酸性条件下环化,从而提供式(II)的中间体,具有根据反应路线9并且例如在WO2014180740中所述进行。
路线9
当Q具有S(Ia)的含义时,具有通式(I)的化合物可以通过使相应的其中Q具有氧的含义的通式(I)化合物与合适的试剂例如如文献中清楚描述的Lawessons试剂或五硫化二磷的反应来制备,例如,如在El-Sharief,A.等人,“Indian Journal of Chemistry,Section B:Organic Chemistry Including Medicinal Chemistry”,1981年,第20卷;nb.9,第751-754页,或在Psutka K.等人中,“RSC Advances”,2016年,第6卷;nb.82,第78784-77890页中所述,根据反应路线10进行。
路线10
当Q具有NOR3(Ib)的含义时,具有通式(I)的化合物可以通过化合物(Ia)与具有式NH2OR3(XIX)的试剂反应来制备,如文献中所述,例如在Poon Steve F.等人,“Bioorganicand Medicinal Chemistry Letters”(2005年),第15卷;nb.9;2259-2263页中所述,根据反应路线11进行:
路线11
当Q具有CR3R4的含义时,具有通式(I)的化合物可以如例如专利申请EP403891中所述制备。
当Q具有NR3R4的含义时,具有通式(I)的化合物可以例如通过将胺NHR3R4和具有通式(II)的化合物在甲苯中的溶液回流直至从反应介质中完全除去水来制备。使用迪安-斯达克(Dean-Stark)设备或通过脱水剂如硫酸钠或通过酸催化来从反应介质中除去水。
G具有G1-G6的含义的式(IX)化合物NH2G,当对于特定的G1-G6含义其不能通过市售获得时,可以通过文献中已知的方法制备,例如Katrizky A.R"ComprehensiveHeterocyclic Chemistry:The Structure,Reactions,Synthesis and Uses ofHeterocyclic Compounds"1998,Elsevier Science&Technology Books中所述。
如已经指出的,具有通式(I)的化合物具有高的除草活性,这使其适合在农业领域中用于保护有用的作物免于杂草的危害。
因此,本发明的另一个目的涉及外消旋形式,异构体纯或它们的混合物的具有通式(I)的化合物或含有它们的组合物作为除草剂的用途。
特别地,本发明的化合物是在杂草尤其是单子叶和双子叶杂草的出苗前和出苗后的防治中均有效。
此外,具有通式(I)的化合物可以用于控制对具有不同作用机理的除草化合物(例如磺酰脲类,草甘膦或4-羟基苯基丙酮酸-双加氧酶(4-HPPD)抑制剂)具有抗性的杂草。
同时,在出苗前和/或出苗后处理中,具有通式(I)的化合物相对于有用的作物可以显示出相容性或没有毒性作用。
因此,就活性成分的使用量而言,本发明的化合物既可以用作总除草剂又可以用作选择性除草剂。
可以使用具有通式(I)的化合物有效控制杂草的例子是:苘麻(Abutilontheofrasti),泽泻(Alisma plantago),苋属(Amaranthus spp.),Amni maius,荠菜(Capsella bursa pastoris),藜(Chenopodium album),篱天剑(Convolvulus sepium),猪殃殃(Galium aparine),深裂老鹳草(Geranium dissectum),雨久花属(Heterantheraspp.),番薯属(Ipomea spp.),母菊属(Matricaria spp.),虞美人(Papaver rhoaes),绿豆(Phaseolus aureus),春蓼(Polygonum persicaria),马齿苋(Portulaca oleracea),狗尾草(Setaria viridis),刺黄花稔(Sida spinosa),野欧白芥(Sinapsis arvensis),龙葵(Solanum nigrum),繁缕(Stellaria media),婆婆纳属(Veronica spp.),堇菜属(Violaspp.),苍耳属(Xanthium spp.),大穗看麦娘(Alopecurus myosuroides),Anisanta spp.,阿披拉草(Apera spica-venti),燕麦属(Avena spp.),莎草属(Cyperus spp.),马唐(Digitaria sanguinalis),属(Eleusine spp.)稗属(Echinochloa spp.),Eleocharisavicularis,黑麦草属(Lolium spp.),黍属(Panicum spp.),早熟禾属(Poa spp.),藨草属(Scirpus spp.),蜀黍属(Sorghum spp.)等。
在对农业应用有效的剂量下,许多上述化合物对一种或多种重要的农作物,例如小麦(Triticum sp.)、大麦(Hordeum vulgare)、玉米(Zea mays)、大豆(Glycine max)没有显示出毒性作用。
本发明的另一个目的涉及防治耕地中杂草的方法,该方法包括将有效剂量的至少一种具有通式(I)的化合物或包含该化合物的组合物施用于目标农作物。
为获得所需效果而要施用的化合物的量(有效剂量)可以根据各种因素而变化,例如,所用的化合物,要保存的农作物,要防治的杂草,侵染程度,气候条件,土壤特性,施用方法等
1g至1,000g/公顷的剂量的化合物通常可以提供足够的防治。
为了将至少一种具有通式(I)的化合物作为除草剂施用到杂草或农作物上,所述具有通式(I)的化合物以组合物的形式配制,该组合物除上述化合物外还包含:至少一种溶剂介质和/或惰性稀释剂介质。所述惰性稀释剂可以是固体或液体形式。该组合物可以任选地包含至少一种农学上可接受的赋形剂。
因此,本发明的另一目的涉及一种除草剂组合物,其包含至少一种外消旋形式、异构体纯或它们的混合物的通式(I)的化合物,至少一种惰性溶剂和/或稀释剂以及任选地至少一种农学上可接受的赋形剂。
惰性稀释剂可以是固体或液体。高岭土、氧化铝、二氧化硅、滑石、膨润土、石膏、石英、白云石、绿坡缕石、蒙脱土、硅藻土、纤维素、淀粉等或其混合物可以用作例如固体稀释剂,也称为载体。
可以使用的液体惰性稀释剂是,例如:水或有机溶剂,例如芳烃(混合二甲苯、烷基苯的混合物等),脂族烃(己烷、环己烷等),卤代芳烃(氯苯等),醇类(甲醇、丙醇、丁醇、辛醇等),酯类(乙酸异丁酯等),酮类(丙酮、环己酮、苯乙酮、异佛尔酮、乙基戊基酮等),植物油,矿物油或其混合物。
所述至少一种农学上可接受的赋形剂优选选自表面活性剂、分散剂、稳定剂及其混合物。
可以使用的表面活性剂例如是非离子型(聚乙氧基化烷基酚、聚乙氧基化脂肪醇等),阴离子型(烷基苯磺酸盐、烷基磺酸盐等)或阳离子型(烷基铵的季盐等)的润湿剂和乳化剂。
木质素及其盐、纤维素衍生物、藻酸盐等也可以例如作为分散剂加入。
也可以添加例如抗氧化剂、紫外线吸收剂等作为稳定剂。
适用于农业用途的制剂可以为以下形式:干粉、可湿性粉剂、乳油、微乳剂、糊剂、颗粒剂、溶液剂、混悬剂等,根据具体用途选择组合物的类型。
为了拓宽上述组合物的作用范围,可以向其中添加与具有通式(I)的化合物相容的一种或多种其他活性成分,例如除具有通式(I)的化合物以外的除草剂、杀真菌剂、杀虫剂、杀螨剂、肥料、植物保护剂(安全剂)等。
可以将除具有通式(I)的化合物以外的除草剂添加到含有至少一种具有通式(I)的化合物的组合物中以扩大作用谱并可能产生协同作用的组合物,所述除草剂的实例如下:
乙草胺,三氟羧草醚,苯草醚,甲草胺,莠灭净,氨唑草酮,酰嘧磺隆,环丙嘧啶酸(amino-cyclopyrachlor),氯氨吡啶酸(aminopyralid),杀草强,莎稗磷,磺草灵,莠去津,唑啶草酮,四唑嘧磺隆,叠氮津(aziprotryne),氟丁酰草胺,草除灵,bencarbazone,乙丁氟灵,呋草黄,地散磷,灭草松,双苯嘧草酮,双环磺草酮,吡草酮,苯噻隆,bicyclopyrone,甲羧除草醚,双丙氨膦,除草定,溴丁酰草胺,溴酚肟,溴苯腈,丁草胺,氟丙嘧草酯,抑草磷,丁烯草胺,仲丁灵,丁苯草酮,丁草敌,唑草胺,双酰草胺,唑草酯,甲氧除草醚,草灭畏,氯溴隆,氯炔灵,整形醇,氯草敏,草枯醚,绿麦隆,枯草隆,氯苯胺灵,氯磺隆,氯酞酸,氯硫酰草胺,吲哚酮草酸(cinidon)乙酯,环庚草醚,醚磺隆,氯酰草膦(clacyfos),烯草酮,炔草酸(clodinafop),异噁草松,氯甲酰草胺,二氯吡啶酸,氯酯磺草胺,苄草隆,氰草津,环草敌,cyclopyrimorate,环丙嘧磺隆,噻草酮,氰氟草酯,环丙磺草胺(cyprosulfamide),2,4-D,2,4-滴丁酸,杀草隆,茅草枯,甜菜安,敌草净,麦草畏,敌草腈,2,4-滴丙酸,精2,4-滴丙酸,禾草灵(diclofop),双氯磺草胺,乙酰甲草胺,枯莠隆,野燕枯,吡氟酰草胺,氟吡草腙,噁唑隆,哌草丹,二甲草胺,异戊乙净,二甲吩草胺,精二甲酚草胺氨氟灵,地乐酚,地乐酯,特乐酚,双苯酰草胺,异丙净,敌草快,氟硫草定,1-敌草隆,甘草津(eglinazine),茵多酸,茵草敌,戊草丹,乙丁烯氟灵,胺苯磺隆-甲酯,磺噻隆,乙嗪草酮,乙氧呋草黄,氟乳醚,乙氧磺隆,乙氧苯草胺,噁唑禾草灵,精噁唑禾草灵,fenoxasulfone,fenquinotrione,四唑酰草胺,非草隆,麦草氟,高效麦草氟,啶嘧磺隆,双氟磺草胺,吡氟禾草灵,精吡氟禾草灵,异丙吡草酯,氟唑磺隆-钠盐,氟吡磺隆,氯乙氟灵,氟噻草胺,氟哒嗪草酸(flufenpyr)乙酯,唑嘧磺草胺,氟烯草酸-戊酯,丙炔氟草胺,炔草胺,氟草隆,乙羧氟草醚,氟除草醚,氟胺草唑,四氟丙酸,氟啶嘧磺隆(flupyr-sulfuron),芴丁酯,氟啶草酮,氟咯草酮,氯氟吡氧乙酸,呋草酮,嗪草酸甲酯,氟磺胺草醚,甲酰氨基嘧磺隆,杀木膦,呋氧草醚,草铵膦酸(glufosinate),精草铵膦酸(glufosinate-P),草甘膦,halauxifen,氯吡嘧磺隆-甲酯,氟吡禾灵,高效氟吡甲禾灵,环嗪酮,咪草酸,甲氧咪草烟,甲咪唑烟酸,咪唑烟酸,咪唑喹啉酸,咪唑乙烟酸,唑吡嘧磺隆,茚草酮,indaziflam,碘磺隆(iodosulfuron),iofensulfuron,碘苯腈,ipfencarbazone,异丙乐灵,异丙隆,异噁隆,异噁酰草胺,异噁氯草酮,异噁唑草酮,异噁草醚,乳氟禾草灵,环草定,利谷隆,2甲4氯,2甲4氯乙硫酯,2甲4氯丁酸,2甲4氯丙酸,精2甲4氯丙酸,苯噻酰草胺,mesosulfuron,硝磺草酮,噁唑酰草胺,苯嗪草酮,吡唑草胺,metazosulfuron,甲基苯噻隆,灭草唑,methiozolin,甲氧丙净,甲基杀草隆,吡喃隆,溴谷隆,异丙甲草胺,精异丙甲草胺,磺草唑胺,甲氧隆,嗪草酮,甲磺隆,禾草敌,庚酰草胺,绿谷隆,萘丙胺,敌草胺,敌草胺-M,萘草胺,草不隆,烟嘧磺隆,氟氯草胺,氟草敏,坪草丹,嘧苯胺磺隆(orthosulfamuron),氨磺乐灵,丙炔噁草酮,噁草酮,环氧嘧磺隆,噁嗪草酮,乙氧氟草醚,百草枯,克草敌,二甲戊灵,五氟磺草胺,甲氯酰草胺,环戊噁草酮,pethoxamid,甜菜宁,氨氯吡啶酸,氯吡酰草胺,哌草磷,丙草胺,氟嘧磺隆,氨氟乐灵,氟唑草胺,环苯草酮,甘扑津,扑灭通,扑草净,毒草胺,敌稗,噁草酸,扑灭津,苯胺灵,异丙草胺,丙氧基缩二氨基脲,propyrisulfuron,炔苯酰草胺,苄草丹,氟磺隆,pyraclonil,吡草醚-乙酯,氟苯唑草酮(pyrasulfotole),双唑草腈,吡唑特,吡嘧磺隆,苄草唑,嘧啶肟草醚,稗草丹,pyridafol,哒草特,环酯草醚,嘧草醚-甲酯,pyrimisulfan,嘧草硫醚-钠盐,pyroxasulfone,啶磺草胺,二氯喹啉酸,氯甲喹啉酸,喹禾灵,精喹禾灵,喹禾糠酯,砜嘧磺隆,苯嘧磺草胺,烯禾啶,环草隆,西玛津,西草净,磺草酮,甲磺草胺,甲嘧磺隆-甲酯,磺酰磺隆-甲基,草芽畏,三氯乙酸钠,牧草胺,丁噻隆,糠氧磺草酮(tefuryltrione),乙氧磺草酮(tembotrione),吡喃草酮,特草定,特丁通,特丁津,特丁净,噻吩草胺,噻氟隆,噻唑烟酸,噻二唑草胺,thiencarbazone,噻吩磺隆-甲酯,禾草丹,tiafenacil,仲草丹,tioclorim,tolpyralate,苯唑草酮(topramezone),三甲苯草酮,triafamone,野麦畏,醚苯磺隆,三嗪氟草胺,苯磺隆-甲酯,三氯吡氧乙酸,草达津,三氟啶磺隆(trifloxysulfuron),trifludimoxazin,氟乐灵,氟胺磺隆-甲酯,三氟甲磺隆,灭草敌。
可以添加到包含至少一种具有通式(I)的化合物的组合物中的安全剂的实例如下:解草嗪,解草酯,解草啶,吡唑解草酯,metamphenifen。
活性物质的浓度,即上述组合物中具有通式(I)的化合物的浓度可以在很大的范围内变化,这取决于活性化合物,它们的预期施用,环境条件和采用的制剂的类型。通常,活性物质的浓度优选为1至90%。
现在提供一些实施例,其应被认为是对本发明的描述和非限制。
为了更好地说明本发明,现在提供以下实施例,其应被认为是说明性的而非限制性的。
实施例1
制备1-(5-叔丁基异噁唑-3-基)-2-环丙烷羰氧基-3,4-二甲基-2H-吡咯-5-酮。
[化合物Nr.4]
a)制备1-(5-叔丁基异噁唑-3-基)-3,4-二甲基马来酰亚胺[具有通式(IV)的中间
体]
15.00g 3-氨基-5-叔丁基-异噁唑(107.1毫摩尔)-具有式(IX)的化合物-和17.60g 2,3-二甲基马来酸酐(139.2毫摩尔)-具有式(VIII)的化合物在250毫升冰醋酸中的溶液在回流条件下加热5小时。将系统冷却至室温,并在搅拌下放置16小时。反应完成后,通过GC-MS对照确认,蒸发溶剂并将残余物溶于水。用二氯甲烷萃取水溶液,并将合并的有机相用10%碳酸钾溶液洗涤。有机相用无水硫酸钠干燥,过滤并浓缩。获得28.09g的所需产物,其无需进一步纯化即可用于下一步。定量收率
GC-MS:M+=248
b)制备1-(5-叔丁基异噁唑-3-基)-2-羟基-3,4-二甲基-2H-吡咯-5-酮[具有通式
(II)的中间体]
在室温、惰性气氛下,将20.00g 1-(5-叔丁基异噁唑-3-基)-3,4-二甲基马来酰亚胺(80.6毫摩尔)-具有式(IV)的化合物-在400ml无水甲醇中的溶液置于搅拌下几分钟。将1.83g硼氢化钠(48.4毫摩尔)小心地分批添加到溶液中。
将体系在室温下搅拌16小时。反应完成后,通过GC-MS对照确认,蒸发溶剂并将残余物溶解在含有4.61ml冰乙酸(80.6毫摩尔)的水溶液中。用二氯甲烷萃取水溶液,并将合并的有机相用水和饱和NaCl溶液洗涤。用无水硫酸钠干燥并过滤后,浓缩有机相,得到17.93g所需产物。收率:89.0%
GC-MS:M+=250
c)1-(5-叔丁基异噁唑-3-基)-2-环丙烷羰氧基-3,4-二甲基-2H-吡咯-5-酮的制
备
[化合物Nr.4]
用冰浴将2.00g 1-(5-叔丁基异噁唑-3-基)-2-羟基-3,4-二甲基-2H-吡咯-5-酮(8.0毫摩尔)(具有式(II)的化合物)-1.67ml三乙胺(12.0毫摩尔)(具有式(Ⅲ)化合物)在65ml无水二氯甲烷中的的溶液冷却至约0℃。将1.09毫升环丙烷甲酰氯(12.0毫摩尔)滴加到该溶液中。添加后,将溶液升至室温,并在搅拌下放置16小时。反应完成后,通过GC-MS对照确认,将60ml水加入溶液中以获得双相体系。分离有机相后,水相用二氯甲烷萃取。合并的有机相用饱和NaCl溶液洗涤,用无水硫酸钠干燥,过滤并浓缩,得到2.95g油。由此获得的材料通过硅胶色谱法纯化,用庚烷:乙酸乙酯溶液9∶1洗脱。获得2.49g所需产物。收率98%
GC-MS:M+=318
LC-MS:MH+=319
实施例2
制备1-(5-叔丁基-1,3,4-噻二唑-2-基)-3,4-二甲基-2-甲氧基乙酸酯-2H-吡咯-5-酮。[化合物Nr.2]
a)制备1-(5-叔丁基-1,3,4-噻二唑-2-基)-2,3-二甲基马来酰亚胺[具有通式
(IV)的中间体]
将0.45g吡咯烷(6.4毫摩尔)和0.38g冰醋酸(6.4毫摩尔)添加到10.00g 2-氨基-5-叔丁基-1,3,4-噻二唑(63.6毫摩尔)-具有式(IX)的化合物-和8.02g的2,3-二甲基马来酸酐(63.6毫摩尔)-具有式(VIII)的化合物-在60ml的甲苯的溶液中。将该溶液回流2小时30分钟。反应完成后,向溶液中加入50ml 10%的HCl水溶液,得到两相体系。分离有机相后,将水相用乙酸乙酯萃取。合并的有机相用10%HCl溶液、水和饱和NaCl溶液洗涤,用无水硫酸钠干燥,过滤并浓缩。如此获得的固体用冷庚烷洗涤。获得15.98g的所需产物。
产率94.8%
GC-MS:M+=265
b)制备1-(5-叔丁基-1,3,4-噻二唑-2-基)-3,4-二甲基-5-羟基-5H-吡咯-2-酮
[具有通式(II)的中间体)]
将15.00g 1-(5-叔丁基-1,3,4-噻二唑-2-基)-2,3-二甲基马来酰亚胺(56.6毫摩尔)-具有式(IV)的化合物-在270ml无水甲醇中的溶液在惰性气氛中于室温搅拌几分钟。将1.29g硼氢化钠(34.0毫摩尔)小心地分批添加到溶液中。将体系在室温下搅拌16小时。反应完成后,通过GC-MS对照确认,蒸发溶剂,并将残余物溶解在含有3.24ml冰乙酸(56.6毫摩尔)的水溶液中。用二氯甲烷萃取水溶液,并将合并的有机相用水和饱和NaCl溶液洗涤。用无水硫酸钠干燥并过滤后,浓缩有机相,得到13.22g的所需产物。收率:87.4%
GC-MS:M+=267
c)制备1-(5-叔丁基-1,3,4-噻二唑-2-基)-3,4-二甲基-2-甲氧基乙酸酯-2H-吡
咯-5-酮[化合物Nr.2]
将0.29ml甲氧基乙酸(3.74毫摩尔)-具有式(III)的化合物添加到1.00g 1-(5-叔丁基-1,3,4-噻二唑-2-基)-3,4-二甲基-5-羟基-5H-吡咯-2-酮(3.74毫摩尔)-具有式(II)的化合物的15ml无水二氯甲烷的溶液中。在用冰浴将溶液冷却至0℃之后,将0.77g的二环己基碳二亚胺(3.74毫摩尔)添加至该系统。添加后,将溶液升至室温,并在搅拌下放置16小时。反应完成后,通过GC-MS对照确认,将溶液过滤并浓缩,得到2.16g油。由此获得的材料通过硅胶色谱法纯化,用二氯甲烷:乙酸乙酯溶液7∶3洗脱。得到1.20g所需产物。收率>95%
GC-MS:M+=339
LC-MS:MH+=340
实施例3
制备1-(5-叔丁基-1,3,4-噻二唑-2-基)-3,4-二甲基-2-甲氧基乙基碳酸酯-2H-
吡咯-2-基-5-酮[化合物Nr.3]
将1.00g 1-(5-叔丁基-1,3,4-噻二唑-2-基)-3,4-二甲基-5-羟基-5H-吡咯-2-酮(3.74毫摩尔)-式(Ⅱ)化合物和0.57ml三乙胺(4.12毫摩尔)在15毫升无水二氯甲烷中的溶液用冰浴冷却至约0℃。将0.48ml氯甲酸2-甲氧基乙酯(4.12毫摩尔)-具有式(III)的化合物-逐滴加入到溶液中。添加后,将溶液升至室温,并在搅拌下放置16小时。反应完成后,通过LC-MS中的对照确认,将60ml水加入溶液中,获得双相体系。分离有机相后,水相用二氯甲烷萃取。合并的有机相用饱和NaCl溶液洗涤,用无水硫酸钠干燥,过滤并浓缩,得到1.22g油。由此获得的材料通过硅胶色谱法纯化,用庚烷:乙酸乙酯溶液9∶1洗脱。得到0.80g所需产物。收率90%
LC-MS:MH+=240
实施例4
1-[4-(4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷(dioxaborolan)-2-基)-吡啶-2-基]-2-环丙烷羰氧基-3,4-二甲基-2H-吡咯-5-酮[化合物Nr.110]的制备
a)1-[4-(4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷-2-基)-吡啶-2-基]-3,4-二
甲基马来酰亚胺[具有通式的中间体]的制备(IV)]
将10.00g 2-氨基-4-(4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷-2-基)吡啶(45.44毫摩尔)和7.45g 2,3-二甲基马来酸酐(59.06毫摩尔)在100毫升冰醋酸中的溶液回流5小时。将系统在室温下冷却,并在搅拌下放置16小时。反应完成后,通过LC-MS对照确认,蒸发溶剂并将残余物溶于水中。用二氯甲烷萃取水溶液,并将合并的有机相用10%碳酸钾溶液洗涤。有机相用无水硫酸钠洗涤,过滤并浓缩。得到15.00g所需产物,其无需进一步纯化就可直接用于下一步。定量收率。
GC-MS:M+=328。
b)1-[4-(4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷-2-基)吡啶-2-基]-2-羟基-
3,4-二甲基-2H-吡咯-5-酮[具有通式(II)的中间体]的制备
在惰性气氛下,将10.00g 1-[4-(4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷-2-基)吡啶-2-基]-3,4-二甲基马来酰亚胺(30.50毫摩尔)在150ml无水甲醇中的溶液在室温下搅拌下几分钟。小心地向溶液中加入0.69克硼氢化钠(18.3毫摩尔)。将体系在室温下搅拌4小时。反应完成后,通过LC-MS对照确认,蒸发溶剂,并将残余物溶于含有1.75ml冰乙酸(30.5毫摩尔)的水溶液中。用二氯甲烷萃取水溶液,并将合并的有机相用水和饱和NaCl溶液洗涤。用无水硫酸钠干燥并过滤后,浓缩有机相,得到8.05g所需产物。收率:80.0%
GC-MS:M+=330
c)1-(4-(4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷-2-基)吡啶-2-基)-2-环丙烷羰氧基-3,4-二甲基-2H-吡咯-5-酮[化合物Nr.110]的制备
将8.00克1-[4-(4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷-2-基)吡啶-2-基]-2-羟基-3,4-二甲基-2H-吡咯-5-酮(24.24毫摩尔)和3.7ml三乙胺(26.66毫摩尔)在250毫升无水二氯甲烷中的溶液用冰浴冷却至约0℃。将2.42毫升环丙烷甲酰氯(26.66毫摩尔)滴加到该溶液中。添加后,将溶液升至室温,并在搅拌下放置16小时。反应完成后,通过LC-MS对照确认,将250ml水加入溶液中,获得双相体系。分离有机相后,水相用二氯甲烷萃取。合并的有机相用饱和NaCl溶液洗涤,用无水硫酸钠干燥,过滤并浓缩,得到10.2g油。由此获得的材料通过硅胶色谱法纯化,用庚烷:乙酸乙酯溶液9∶1洗脱。得到8.8克所需产物。收率91%
GC-MS:M+=398
LC-MS:MH+=399
实施例5
化合物Nrs.11、14、18、22、100、101、109、110、113、114、117-119的制备
与前述实施例类似地进行操作,获得表3中所示的具有式(I)的化合物11、14、18、22、100、101、109、110、113、114、117-119。
表3
表4给出了对化合物11、14、18、22、100、101、109、110、113、114和117-119进行的LC-MS分析结果。
表4
实施例6
出苗前除草活性和植物毒性的测定。
根据以下操作模式评估本发明化合物的苗前除草活性。
将感兴趣的植物物种(杂草或农作物)播种在直径为10厘米,高度为10厘米并包含沙土的花盆中。每种植物使用六盆。
将水以适合种子发芽的量加到每个盆中。然后将这些盆分为两组,每组针对每种杂草或农作物包含3个盆。
播种后一天,用具有以下组成的分散液处理第一组盆:
-通式(I)的化合物200毫克
-水56毫升
-丙酮14毫升
-吐温20 0.5%(w/w)
相对于分散液的总重量,通过将所需剂量的本发明化合物添加到含有20体积%的丙酮和0.5重量%的吐温20的丙酮水溶液中来制备分散液,并将其施加在2平方米的表面上。
本发明的每种化合物的重量(weighing)对应于1,000g/ha的有效剂量。
第二组仅用含有20体积%的丙酮和0.5重量%的吐温20的丙酮水溶液处理,并用作比较项(对照)。
在以下环境条件下,将所有盆放在调控的环境(温室)中进行观察:
-温度:白天24℃,晚上18℃
-相对湿度:>50%
-光照期:16小时;
-光强度:12,000勒克斯。
根据需要对盆进行均匀浇水,以确保足以使植物良好生长的湿度。
处理二十一天后,根据与未处理植物(对照)相比在处理植物上发现的伤害百分数(等级0-100%)评估除草活性:
-0%=对植物无影响
-100%=植物完全死亡
表5显示了,用Comp.Nrs.4和2处理以下所示的植物物种获得的结果,并将其与含有EP0297378中所述的化合物CR1代替具有通式(I)的化合物的分散液相比:
CR1=1-(5-叔丁基异噁唑-3-基)-2-羟基-3,4-二甲基-2H-吡咯-5-酮
表5:250g/ha剂量下的苗前除草活性
实施例7
出苗后除草活性和植物毒性的测定
根据以下操作模式评价本发明化合物的苗后除草活性。
将感兴趣的植物物种(杂草或农作物)播种在直径大于10厘米,高度为10厘米且含有沙土的花盆中。每种植物使用六个盆。
将水以适合种子发芽的量加到每个盆中。然后将这些盆分为两组,每组针对每种杂草或农作物包含3个盆。
在达到具有1-2扩展叶片(BBCH 11-12)的植物的物候阶段时,将第一组盆用如实施例6所示相同的丙酮水分散液处理,该分散液含有20体积%的丙酮、所需剂量的待测化合物和0.5重量%的吐温20。
第二组仅用含有20体积%的丙酮和0.5重量%的吐温20的丙酮水溶液处理,并用作比较项(对照)。
在以下环境条件下,将所有盆放在调控的环境(温室)中进行观察:
-温度:白天24℃,晚上18℃
-相对湿度:>50%
-光照期:16小时;
-光强度:12,000勒克斯。
根据需要对盆进行均匀浇水,以确保足以使植物良好生长的湿度。
处理二十一天后,根据与未处理植物(对照)相比在处理植物上发现的伤害百分数(等级0-100%)评估除草活性:
-0%=对植物无影响
-100%=植物完全死亡
表6显示了用Comp.Nrs.11、4、2、3处理以下所示的植物物种获得的结果,并将其与含有EP0297378中所述的化合物CR1的丙酮水分散液相比较。
CR1=1-(5-叔丁基异噁唑-3-基)-2-羟基-3,4-二甲基-2H-吡咯-5-酮
表6:250g/ha剂量下的苗后除草活性
Claims (16)
1.通式(I)的化合物、其异构体、盐或水合物:
其中:
-R代表C3-C18环烷基羰基,C3-C18环烷基硫羰基,C7-C12烷基羰基,C3-C18环烷氧基羰基,C3-C18环烷基C1-C6烷基羰基,C3-C18环烷基C1-C12烷基硫羰基,C1-C12烷氧基C1-C12烷基羰基,C1-C12烷氧基C1-C12烷基硫羰基,C3-C18环烷氧基C1-C12烷基羰基,C3-C18环烷氧基C1-C12烷基硫羰基,C1-C12烷硫基C1-C12烷基羰基,C3-C18环烷基硫C1-C12烷基羰基,C1-C12烷基羧基C1-C12烷基羰基,C3-C18环烷基羧基C1-C12烷基羰基,C1-C12烷基羰基C1-C12烷基羰基,C3-C18环烷基羰基C1-C12烷基羰基,C1-C12烷氧基C1-C12烷氧基羰基,C3-C18环烷氧基C1-C12烷氧基羰基,C1-C12烷硫基C1-C12烷氧基羰基,C3-C18环烷硫基C1-C12烷氧基羰基,C3-C18环烷基羧基C1-C12烷氧基羰基,芳基C1-C12烷氧基羰基,C1-C12烷氧基C2-C12烷基,芳氧基C1-C12烷基,苄氧基C2-C12烷基,C3-C18环烷氧基C1-C12烷基,C1-C12烷基羧基C1-C12烷基,C3-C18环烷基羧基C1-C12烷基,C1-C12烷硫基C1-C12烷基,C3-C18环烷硫基C1-C12烷基,C1-C12烷基羰基C1-C12烷基,C3-C18环烷基羰基C1-C12烷基,C1-C12烷氧基羰基C1-C12烷基,C3-C18环烷氧基羰基C1-C12烷基,C2-C6卤代链烯基羰基,R3R4R5Si,CO-COOR3,COCR3 2COOR3,双官能团-SiR3R4(CH2)mSiR3R4-基团,双官能团-(CO-CO)-基团,双官能团-(COCR3 2CO)-基团,双官能团-[COO(CH2)mOCO]-基团;
-R1和R2彼此相同或不同,表示卤原子,C1-C12烷基,C1-C12卤代烷基,C3-C18环烷基,C1-C12烷氧基,C3-C18环烷氧基;
-Z表示O原子,S原子或NR4基团;
-Q表示O原子,S原子,NOR3基团,NR3R4基团,C=CR3R4基团;
-R3,R4,R5彼此相同或不同,表示氢原子,C1-C12烷基,C1-C12卤代烷基,C3-C18环烷基;
-m是1至5的整数;
-n为1或2;
-G表示5或6元的芳香族杂环,其选自:
并且其中:
-X表示氮原子或CRa基团;
-W表示氧原子,或硫原子或NRa基团;
-Ra,Rb,Rc彼此相同或不同,表示氢原子,卤素原子,C1-C12烷基,C2-C12烯基,C2-C12卤代烯基,C3-C18环烯基,C3-C18环烷基,C2-C12炔基,C1-C12卤代烷基,C1-C12烷氧基,C1-C12卤代烷氧基,C3-C18环烷氧基,CN基团,B(OR3)2基团,4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷基;
条件是,当:
(i)R表示环丙基羰基,环己基羰基或3-酮丁酰基,并且
(ii)R1和R2均为甲基,并且
(iii)Q和Z为氧原子,且
(iv)n等于1时,
那么G不同于其中Ra和Rb都是氢或其中Ra是甲基并且Rb是氢的G6。
3.根据权利要求1的通式(I)的化合物,其中:
-R表示选自C3-C12环烷基羰基,C1-C18烷氧基烷基羰基,C1-C18烷氧基C1-C18烷氧基羰基,R3R4R5Si基团或-(COCO)-基团的基团,
-Z代表氧原子或硫原子,
-Q代表氧原子或NOH基团,
-R1和R2彼此相同表示C1-C4烷基,
-n等于1或2并且
-G选自G1至G6,并且代表含有至少一个选自氮、氧和硫的杂原子的六或五元杂环。
4.根据权利要求1的通式(I)的化合物,其中:
-R表示选自环丙基羰基,甲氧基甲基羰基,甲氧基乙氧基羰基,三甲基甲硅烷基或-(COCO)-基团的基团,
-R1和R2为甲基或乙基,
-Z和Q代表氧原子,
-n等于1或2并且
-G选自G1至G4,并且代表噻二唑基、异噁唑基或吡唑基。
6.除草剂组合物,其包含:至少一种根据权利要求1的通式(I)的化合物;至少一种溶剂和/或至少一种稀释剂;任选地,至少一种农学上可接受的赋形剂。
7.根据前述权利要求的除草剂组合物,其包含至少一种与通式(I)的化合物相容的活性成分,选自:与通式(I)的那些不同的除草剂,杀真菌剂,杀虫剂,杀螨剂,肥料,植物保护剂和其混合物。
8.根据权利要求6的除草剂组合物,其中所述通式(I)的化合物以相对于组合物总重量的1重量%至90重量%的浓度存在。
9.根据权利要求1的通式(I)的化合物或根据权利要求6的组合物作为除草剂的用途,用于防治农作物中的至少一种杂草。
10.根据权利要求9的用途,其用于在出苗前或出苗后防治农作物中的至少一种杂草。
11.根据权利要求9或10的用途,其中所述杂草选自:苘麻(Abutilon theofrasti),泽泻(Alisma plantago),苋属(Amaranthus spp.),Amni maius,荠菜(Capsella bursapastoris),藜(Chenopodium album),篱天剑(Convolvulus sepium),猪殃殃(Galiumaparine),深裂老鹳草(Geranium dissectum),雨久花属(Heteranthera spp.),番薯属(Ipomea spp.),母菊属(Matricaria spp.),虞美人(Papaver rhoaes),绿豆(Phaseolusaureus),春蓼(Polygonum persicaria),马齿苋(Portulaca oleracea),狗尾草(Setariaviridis),刺黄花稔(Sida spinosa),野欧白芥(Sinapsis arvensis),龙葵(Solanumnigrum),繁缕(Stellaria media),婆婆纳属(Veronica spp.),堇菜属(Viola spp.),苍耳属(Xanthium spp.),大穗看麦娘(Alopecurus myosuroides),Anisanta spp.,阿披拉草(Apera spica-venti),燕麦属(Avena spp.),莎草属(Cyperus spp.),马唐(Digitariasanguinalis),属(Eleusine spp.)稗属(Echinochloa spp.),Eleocharisavicularis,黑麦草属(Lolium spp.),黍属(Panicum spp.),早熟禾属(Poa spp.),藨草属(Scirpus spp.),蜀黍属(Sorghum spp.)。
12.根据权利要求9-11中一项或多项的用途,其中所述农作物选自:小麦(Triticumsp.)、大麦(Hordeumvulgare)、玉米(Zeamays)、大豆(Glycinemax)。
13.用于防治农作物中的至少一种杂草的方法,其包括:将至少一个有效剂量的至少一种根据权利要求1的通式(I)的化合物或至少一种根据权利要求6的除草剂组合物施用于所述农作物。
14.根据前述权利要求的方法,其中将所述通式(I)的化合物或所述除草剂组合物以1-1000g/ha范围内的所述通式(I)的化合物的剂量施用于农作物。
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