CN103717581A - N-(四唑-5-基)芳基甲酰胺和n-(三唑-5-基)芳基甲酰胺及其作为除草剂的用途 - Google Patents
N-(四唑-5-基)芳基甲酰胺和n-(三唑-5-基)芳基甲酰胺及其作为除草剂的用途 Download PDFInfo
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- CN103717581A CN103717581A CN201280038161.9A CN201280038161A CN103717581A CN 103717581 A CN103717581 A CN 103717581A CN 201280038161 A CN201280038161 A CN 201280038161A CN 103717581 A CN103717581 A CN 103717581A
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- alkyl
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- cycloalkyl
- halo
- heterocyclic radical
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- AXKBOWBNOCUNJL-UHFFFAOYSA-M sodium;2-nitrophenolate Chemical compound [Na+].[O-]C1=CC=CC=C1[N+]([O-])=O AXKBOWBNOCUNJL-UHFFFAOYSA-M 0.000 description 1
- YPMAQKXGDCKXPE-WCCKRBBISA-M sodium;[(3s)-3-amino-3-carboxypropyl]-methylphosphinate Chemical compound [Na+].CP([O-])(=O)CC[C@H](N)C(O)=O YPMAQKXGDCKXPE-WCCKRBBISA-M 0.000 description 1
- JRQGDDUXDKCWRF-UHFFFAOYSA-M sodium;n-(2-methoxycarbonylphenyl)sulfonyl-4-methyl-5-oxo-3-propoxy-1,2,4-triazole-1-carboximidate Chemical compound [Na+].O=C1N(C)C(OCCC)=NN1C(=O)[N-]S(=O)(=O)C1=CC=CC=C1C(=O)OC JRQGDDUXDKCWRF-UHFFFAOYSA-M 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- PQTBTIFWAXVEPB-UHFFFAOYSA-N sulcotrione Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O PQTBTIFWAXVEPB-UHFFFAOYSA-N 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 150000004763 sulfides Chemical class 0.000 description 1
- FZMKKCQHDROFNI-UHFFFAOYSA-N sulfometuron Chemical compound CC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 FZMKKCQHDROFNI-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 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
- FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical group 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- YGNGABUJMXJPIJ-UHFFFAOYSA-N thiatriazole Chemical compound C1=NN=NS1 YGNGABUJMXJPIJ-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 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
- XSKZXGDFSCCXQX-UHFFFAOYSA-N thiencarbazone-methyl Chemical compound COC(=O)C1=CSC(C)=C1S(=O)(=O)NC(=O)N1C(=O)N(C)C(OC)=N1 XSKZXGDFSCCXQX-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- LOQQVLXUKHKNIA-UHFFFAOYSA-N thifensulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C2=C(SC=C2)C(O)=O)=N1 LOQQVLXUKHKNIA-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- GYICYQJEVCIYJY-UHFFFAOYSA-N thiophen-1-ylidenemethanone Chemical compound O=C=S1C=CC=C1 GYICYQJEVCIYJY-UHFFFAOYSA-N 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
- XMLSXPIVAXONDL-UHFFFAOYSA-N trans-jasmone Natural products CCC=CCC1=C(C)CCC1=O XMLSXPIVAXONDL-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 150000003852 triazoles Chemical group 0.000 description 1
- BQZXUHDXIARLEO-UHFFFAOYSA-N tribenuron Chemical compound COC1=NC(C)=NC(N(C)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 BQZXUHDXIARLEO-UHFFFAOYSA-N 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 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
- DFFWZNDCNBOKDI-UHFFFAOYSA-N trinexapac Chemical compound O=C1CC(C(=O)O)CC(=O)C1=C(O)C1CC1 DFFWZNDCNBOKDI-UHFFFAOYSA-N 0.000 description 1
- RVKCCVTVZORVGD-UHFFFAOYSA-N trinexapac-ethyl Chemical group O=C1CC(C(=O)OCC)CC(=O)C1=C(O)C1CC1 RVKCCVTVZORVGD-UHFFFAOYSA-N 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 239000002023 wood Substances 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
- A01N43/72—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
- C07D257/06—Five-membered rings with nitrogen atoms directly attached to the ring carbon atom
-
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
- A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/14—Nitrogen 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
- C07D401/12—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
- 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
- C07D401/14—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 three or more hetero rings
-
- 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
- C07D403/12—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 linked by a chain containing hetero atoms as chain links
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- 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
-
- 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
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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Abstract
本发明描述了作为除草剂的通式(I)的N-(四唑-5-基)芳基甲酰胺和N-(三唑-5-基)芳基甲酰胺。
Description
本发明涉及除草剂技术领域,特别是用于选择性防治有用植物作物中的阔叶杂草和禾本科杂草的除草剂技术领域。
WO2003/010143和WO2003/010153公开了N-(四唑-5-基)苯甲酰胺和N-(三唑-5-基)苯甲酰胺及其药理学作用。EP101748937——其具有较早的优先权但未在先公开——公开了某些作为除草剂的N-(四唑-5-基)苯甲酰胺、N-(四唑-5-基)烟酰胺、N-(三唑-5-基)苯甲酰胺和N-(三唑-5-基)烟酰胺。现已发现,在四唑环或三唑环的1-位上带有特定取代基的N-(四唑-5-基)芳基甲酰胺、N-(四唑-5-基)烟酰胺、N-(三唑-5-基)芳基甲酰胺和N-(三唑-5-基)烟酰胺特别适合作为除草剂。
因此,本发明提供式(I)的N-(四唑-5-基)芳基甲酰胺和N-(三唑-5-基)芳基甲酰胺或其盐
其中
A代表N或CY,
B代表N或CH,
X代表硝基、卤素、氰基、甲酰基、氰硫基、(C1-C6)烷基、卤代-(C1-C6)烷基、(C2-C6)烯基、卤代-(C2-C6)烯基、(C2-C6)炔基、卤代-(C3-C6)炔基、(C3-C6)环烷基、卤代-(C3-C6)环烷基、(C3-C6)环烷基-(C1-C6)烷基、卤代-(C3-C6)环烷基-(C1-C6)烷基、COR1、COOR1、OCOOR1、NR1COOR1、C(O)N(R1)2、NR1C(O)N(R1)2、OC(O)N(R1)2、C(O)NR1OR1、OR1、OCOR1、OSO2R2、S(O)nR2、SO2OR1、SO2N(R1)2、NR1SO2R2、NR1COR1、(C1-C6)烷基-S(O)nR2、(C1-C6)烷基-OR1、(C1-C6)烷基-OCOR1、(C1-C6)烷基-OSO2R2、(C1-C6)烷基-CO2R1、(C1-C6)烷基-SO2OR1、(C1-C6)烷基-CON(R1)2、(C1-C6)烷基-SO2N(R1)2、(C1-C6)烷基-NR1COR1、(C1-C6)烷基-NR1SO2R2、NR1R2、P(O)(OR5)2、CH2P(O)(OR5)2、(C1-C6)烷基-杂芳基、(C1-C6)烷基-杂环基,其中最后提及的两种基团各自被s个选自卤素、(C1-C6)烷基、卤代-(C1-C6)烷基、S(O)n-(C1-C6)烷基、(C1-C6)烷氧基、卤代-(C1-C6)烷氧基的基团取代,且其中杂环基带有n个氧代基团,
Y代表氢、硝基、卤素、氰基、氰硫基、(C1-C6)烷基、卤代-(C1-C6)烷基、(C2-C6)烯基、卤代-(C2-C6)烯基、(C2-C6)炔基、卤代-(C2-C6)炔基、(C3-C6)环烷基、(C3-C6)环烯基、卤代-(C3-C6)环烷基、(C3-C6)环烷基-(C1-C6)烷基、卤代-(C3-C6)环烷基-(C1-C6)烷基、COR1、COOR1、OCOOR1、NR1COOR1、C(O)N(R1)2、NR1C(O)N(R1)2、OC(O)N(R1)2、CO(NOR1)R1、NR1SO2R2、NR1COR1、OR1、OSO2R2、S(O)nR2、SO2OR1、SO2N(R1)2(C1-C6)烷基-S(O)nR2、(C1-C6)烷基-OR1、(C1-C6)烷基-OCOR1、(C1-C6)烷基-OSO2R2、(C1-C6)烷基-CO2R1、(C1-C6)烷基-CN、(C1-C6)烷基-SO2OR1、(C1-C6)烷基-CON(R1)2、(C1-C6)烷基-SO2N(R1)2、(C1-C6)烷基-NR1COR1、(C1-C6)烷基-NR1SO2R2、N(R1)2、P(O)(OR5)2、CH2P(O)(OR5)2、(C1-C6)烷基-苯基、(C1-C6)烷基-杂芳基、(C1-C6)烷基-杂环基、苯基、杂芳基或杂环基,其中最后提及的6个基团各自被s个选自卤素、硝基、氰基、(C1-C6)烷基、卤代-(C1-C6)烷基、(C3-C6)环烷基、S(O)n-(C1-C6)烷基、(C1-C6)烷氧基、卤代-(C1-C6)烷氧基、(C1-C6)烷氧基-(C1-C4)烷基和氰甲基的基团取代,且其中杂环基带有n个氧代基团,
Z代表卤素、氰基、氰硫基、卤代-(C1-C6)烷基、(C2-C6)烯基、卤代-(C2-C6)烯基、(C2-C6)炔基、卤代-(C2-C6)炔基、(C3-C6)环烷基、卤代-(C3-C6)环烷基、(C3-C6)环烷基-(C1-C6)烷基、卤代-(C3-C6)环烷基-(C1-C6)烷基、COR1、COOR1、OCOOR1、NR1COOR1、C(O)N(R1)2、NR1C(O)N(R1)2、OC(O)N(R1)2、C(O)NR1OR1、OSO2R2、S(O)nR2、SO2OR1、SO2N(R1)2、NR1SO2R2、NR1COR1、(C1-C6)烷基-S(O)nR2、(C1-C6)烷基-OR1、(C1-C6)烷基-OCOR1、(C1-C6)烷基-OSO2R2、(C1-C6)烷基-CO2R1、(C1-C6)烷基-SO2OR1、(C1-C6)烷基-CON(R1)2、(C1-C6)烷基-SO2N(R1)2、(C1-C6)烷基-NR1COR1、(C1-C6)烷基-NR1SO2R2、N(R1)2、P(O)(OR5)2、杂芳基、杂环基或苯基,其中最后提及的3个基团各自被s个选自卤素、硝基、氰基、(C1-C6)烷基、卤代-(C1-C6)烷基、(C3-C6)环烷基、S(O)n-(C1-C6)烷基、(C1-C6)烷氧基和卤代-(C1-C6)烷氧基的基团取代,且其中杂环基带有n个氧代基团,或
Z在Y代表基团S(O)nR2时,其还可代表氢、(C1-C6)烷基或(C1-C6)烷氧基,
R代表CH2R6,
被m个氧代基团取代的CH2-杂环基,
被t个(C1-C6)烷基取代的(C3-C7)环烷基,
(C2-C6)烷基、(C3-C7)环烷基、卤代-(C2-C6)烷基、(C2-C6)烯基、卤代-(C2-C6)烯基、(C2-C6)炔基或卤代-(C2-C6)炔基,所述基团各自被u个选自硝基、氰基、羟基、氧代、SiR5 3、PO(OR5)2、S(O)n-(C1-C6)烷基、(C1-C6)烷氧基、卤代-(C1-C6)烷氧基、N(R3)2、COR3、OCOR3、NR3COR3、NR3SO2R4、(C3-C6)环烷基、杂芳基、杂环基、苯基、Q-杂芳基、Q-杂环基、Q-苯基和Q-苄基的基团取代,其中所述基团(C3-C6)环烷基、杂芳基、杂环基、苯基、Q-杂芳基、Q-杂环基、Q-苯基和Q-苄基各自被s个选自甲基、乙基、甲氧基、氰基、硝基、三氟甲基和卤素的基团取代,且其中杂环基和环烷基带有n个氧代基团,
Q代表O、S或NR3,
R1代表氢、(C1-C6)烷基、(C1-C6)卤代烷基、(C2-C6)烯基、(C2-C6)卤代烯基、(C2-C6)炔基、(C2-C6)卤代炔基、(C3-C6)环烷基、(C3-C6)环烯基、(C3-C6)卤代环烷基、(C1-C6)烷基-O-(C1-C6)烷基、(C3-C6)环烷基-(C1-C6)烷基、苯基、苯基-(C1-C6)烷基、杂芳基、(C1-C6)烷基-杂芳基、杂环基、(C1-C6)烷基-杂环基、(C1-C6)烷基-O-杂芳基、(C1-C6)烷基-O-杂环基、(C1-C6)烷基-NR3-杂芳基、(C1-C6)烷基-NR3-杂环基,其中最后提及的21个基团被s个选自氰基、卤素、硝基、氰硫基、OR3、S(O)nR4、N(R3)2、NR3OR3、COR3、OCOR3、SCOR4、NR3COR3、NR3SO2R4、CO2R3、COSR4、CON(R3)2和(C1-C4)烷氧基-(C2-C6)烷氧基羰基的基团取代,且其中杂环基带有n个氧代基团,
R2代表(C1-C6)烷基、(C1-C6)卤代烷基、(C2-C6)烯基、(C2-C6)卤代烯基、(C2-C6)炔基、(C2-C6)卤代炔基、(C3-C6)环烷基、(C3-C6)环烯基、(C3-C6)卤代环烷基、(C1-C6)烷基-O-(C1-C6)烷基、(C3-C6)环烷基-(C1-C6)烷基、苯基、苯基-(C1-C6)烷基、杂芳基、(C1-C6)烷基-杂芳基、杂环基、(C1-C6)烷基-杂环基、(C1-C6)烷基-O-杂芳基、(C1-C6)烷基-O-杂环基、(C1-C6)烷基-NR3-杂芳基、(C1-C6)烷基-NR3-杂环基,其中最后提及的21个基团被s个选自氰基、卤素、硝基、氰硫基、OR3、S(O)nR4、N(R3)2、NR3OR3、COR3、OCOR3、SCOR4、NR3COR3、NR3SO2R4、CO2R3、COSR4、CON(R3)2和(C1-C4)烷氧基-(C2-C6)烷氧基羰基的基团取代,且其中杂环基带有n个氧代基团,
R3代表氢、(C1-C6)烷基、(C2-C6)烯基、(C2-C6)炔基、(C3-C6)环烷基或(C3-C6)环烷基-(C1-C6)烷基,
R4代表(C1-C6)烷基、(C2-C6)烯基或(C2-C6)炔基、(C3-C6)环烷基或(C3-C6)环烷基-(C1-C6)烷基,
R5代表(C1-C4)烷基,
R6代表OCOOR4、NR4COOR4、S(O)n-(C1-C6)烷基、S(O)n-(C1-C6)卤代烷基、硝基、氰基、SiR5 3、PO(OR5)2、杂环基或环烷基,其中最后提及的2个基团带有m个氧代基团或羟基,
m代表1或2,
n代表0、1或2,
s代表0、1、2或3,
t代表1、2、3或4,
u代表1、2、3、4或5。
在式(I)和所有下式中,含有大于2个碳原子的烷基可为直链或支链的。烷基为,例如,甲基、乙基、正丙基或异丙基、正丁基、异丁基、叔丁基或2-丁基、戊基、己基(例如正己基、异己基和1,3-二甲基丁基)。类似地,烯基为,例如,烯丙基、1-甲基丙-2-烯-1-基、2-甲基丙-2-烯-1-基、丁-2-烯-1-基、丁-3-烯-1-基、1-甲基丁-3-烯-1-基和1-甲基丁-2-烯-1-基。炔基为,例如,炔丙基、丁-2-炔-1-基、丁-3-炔-1-基、1-甲基丁-3-炔-1-基。在每种情况下,多重键可在不饱和基团的任意位置。环烷基为含有3-6个碳原子的碳环饱和环系,例如环丙基、环丁基、环戊基或环己基。类似地,环烯基为含有3-6个碳环原子的单环烯基,例如环丙烯基、环丁烯基、环戊烯基和环己烯基,其中双键可在任意位置。
卤素代表氟、氯、溴或碘。
杂环基为含有3-6个环原子的饱和、部分饱和或完全不饱和的环状基团,环原子中的1-4个原子选自氧、氮和硫,且其还可以稠合至苯环。杂环基为,例如哌啶基、吡咯烷基、四氢呋喃基、二氢呋喃基和氧杂环丁烷基。杂芳基为含有3-6个环原子的芳环基团,环原子中的1-4个原子选自氧、氮和硫,且其还可稠合至苯环。杂芳基为,例如,苯并咪唑-2-基、呋喃基、咪唑基、异噁唑基、异噻唑基、噁唑基、吡嗪基、嘧啶基、哒嗪基、吡啶基、苯并异噁唑基、噻唑基、吡咯基、吡唑基、噻吩基、1,2,3-噁二唑基、1,2,4-噁二唑基、1,2,5-噁二唑基、1,3,4-噁二唑基、1,2,4-三唑基、1,2,3-三唑基、1,2,5-三唑基、1,3,4-三唑基、1,2,4-三唑基、1,2,4-噻二唑基、1,3,4-噻二唑基、1,2,3-噻二唑基、1,2,5-噻二唑基、2H-1,2,3,4-四唑基、1H-1,2,3,4-四唑基、1,2,3,4-噁三唑基、1,2,3,5-噁三唑基、1,2,3,4-噻三唑基和1,2,3,5-噻三唑基。
当一个基团被多个基团取代时,这意味着这个基团被一个或多个相同或不同的所提及基团的代表所取代。
取决于取代基的性质和连接方式,式(I)的化合物可以以立体异构体的形式存在。如果,例如存在一个或多个不对称取代的碳原子,则可能存在对映异构体和非对映异构体。如果n为1(亚砜),也可能存在立体异构体。可以从制备所得的混合物中使用常规分离方法例如色谱分离技术获得立体异构体。也可以采用光学活性的起始原料和/或助剂,通过使用立体选择性反应来选择性地制备立体异构体。本发明还涉及式(I)所涵盖的但并未具体定义的所有立体异构体及其混合物。
优选式(I)的化合物,其中
A代表N或CY,
B代表N或CH,
X代表硝基、卤素、氰基、氰硫基、(C1-C6)烷基、卤代-(C1-C6)烷基、(C2-C6)烯基、卤代-(C2-C6)烯基、(C2-C6)炔基、卤代-(C3-C6)炔基、(C3-C6)环烷基、卤代-(C3-C6)环烷基、C1-C6)烷基-O-(C1-C6)烷基、(C3-C6)环烷基-(C1-C6)烷基、卤代-(C3-C6)环烷基-(C1-C6)烷基、COR1、OR1、OCOR1、OSO2R2、S(O)nR2、SO2OR1、SO2N(R1)2、NR1SO2R2、NR1COR1、(C1-C6)烷基-S(O)nR2、(C1-C6)烷基-OR1、(C1-C6)烷基-OCOR1、(C1-C6)烷基-OSO2R2、(C1-C6)烷基-CO2R1、(C1-C6)烷基-SO2OR1、(C1-C6)烷基-CON(R1)2、(C1-C6)烷基-SO2N(R1)2、(C1-C6)烷基-NR1COR1或(C1-C6)烷基-NR1SO2R2、(C1-C6)烷基-杂芳基、(C1-C6)烷基-杂环基,其中最后提及的2个基团各自被s个选自卤素、(C1-C6)烷基、卤代-(C1-C6)烷基、S(O)n-(C1-C6)烷基、(C1-C6)烷氧基、卤代-(C1-C6)烷氧基的基团取代,且其中杂环基带有n个氧代基团,
Y代表氢、硝基、卤素、氰基、氰硫基、(C1-C6)烷基、卤代-(C1-C6)烷基、(C2-C6)烯基、卤代-(C2-C6)烯基、(C2-C6)炔基、卤代-(C3-C6)炔基、(C3-C6)环烷基、(C3-C6)环烯基、卤代-(C3-C6)环烷基、(C3-C6)环烷基-(C1-C6)烷基、卤代-(C3-C6)环烷基-(C1-C6)烷基、COR1、OR1、COOR1、OSO2R2、S(O)nR2、SO2OR1、SO2N(R1)2、N(R1)2、NR1SO2R2、NR1COR1、(C1-C6)烷基-S(O)nR2、(C1-C6)烷基-OR1、(C1-C6)烷基-OCOR1、(C1-C6)烷基-OSO2R2、(C1-C6)烷基-CO2R1、(C1-C6)烷基-SO2OR1、(C1-C6)烷基-CON(R1)2、(C1-C6)烷基-SO2N(R1)2、(C1-C6)烷基-NR1COR1、(C1-C6)烷基-NR1SO2R2、(C1-C6)烷基-苯基、(C1-C6)烷基-杂芳基、(C1-C6)烷基-杂环基、苯基、杂芳基或杂环基,其中最后提及的6个基团各自被s个选自卤素、硝基、氰基、(C1-C6)烷基、卤代-(C1-C6)烷基、(C3-C6)环烷基、S(O)n-(C1-C6)烷基、(C1-C6)烷氧基、卤代-(C1-C6)烷氧基、(C1-C6)烷氧基-(C1-C4)烷基和氰甲基的基团取代,且其中所述杂环基带有n个氧代基团,
Z代表卤素、氰基、氰硫基、卤代-(C1-C6)烷基、(C2-C6)烯基、卤代-(C2-C6)烯基、(C2-C6)炔基、卤代-(C3-C6)炔基、(C3-C6)环烷基、卤代-(C3-C6)环烷基、(C3-C6)环烷基-(C1-C6)烷基、卤代-(C3-C6)环烷基-(C1-C6)烷基、COR1、COOR1、C(O)N(R1)2、C(O)NR1OR1、OSO2R2、S(O)nR2、SO2OR1、SO2N(R1)2、NR1SO2R2、NR1COR1、(C1-C6)烷基-S(O)nR2、(C1-C6)烷基-OR1、(C1-C6)烷基-OCOR1、(C1-C6)烷基-OSO2R2、(C1-C6)烷基-CO2R1、(C1-C6)烷基-SO2OR1、(C1-C6)烷基-CON(R1)2、(C1-C6)烷基-SO2N(R1)2、(C1-C6)烷基-NR1COR1、(C1-C6)烷基-NR1SO2R2、1,2,4-三唑-1-基,或
Z在Y代表基团S(O)nR2时,其还可代表氢、(C1-C6)烷基或(C1-C6)烷氧基,
R代表CH2R6,
被m个氧代基团取代的CH2-杂环基、
(C2-C6)烷基、(C3-C7)环烷基、卤代-(C2-C6)烷基、(C2-C6)烯基、卤代-(C2-C6)烯基、(C2-C6)炔基或卤代-(C2-C6)炔基,所述基团各自被u个选自硝基、氰基、羟基、氧代、SiR5 3、PO(OR5)2、S(O)n-(C1-C6)烷基、(C1-C6)烷氧基、卤代-(C1-C6)烷氧基、N(R3)2、COR3、OCOR3、NR3COR3、NR3SO2R4、(C3-C6)环烷基、杂芳基、杂环基、苯基、Q-杂芳基、Q-杂环基、Q-苯基和Q-苄基的基团取代,其中所述基团(C3-C6)环烷基、杂芳基、杂环基、苯基、Q-杂芳基、Q-杂环基、Q-苯基和Q-苄基各自被s个选自甲基、乙基、甲氧基、氰基、硝基、三氟甲基和卤素的取代基取代,且其中杂环基和环烷基带有n个氧代基团,
Q代表O、S或NR3,
R1代表氢、(C1-C6)烷基、(C2-C6)烯基、(C2-C6)炔基、(C3-C6)环烷基、(C3-C6)环烷基-(C1-C6)烷基、(C1-C6)烷基-O-(C1-C6)烷基、苯基、苯基-(C1-C6)烷基、杂芳基、(C1-C6)烷基-杂芳基、杂环基、(C1-C6)烷基-杂环基、(C1-C6)烷基-O-杂芳基、(C1-C6)烷基-O-杂环基、(C1-C6)烷基-NR3-杂芳基或(C1-C6)烷基-NR3-杂环基,其中最后提及的16个基团被s个选自氰基、卤素、硝基、OR3、S(O)nR4、N(R3)2、NR3OR3、COR3、OCOR3、NR3COR3、NR3SO2R4、CO2R3、CON(R3)2和(C1-C4)烷氧基-(C2-C6)烷氧基羰基的基团取代,且其中杂环基带有n个氧代基团,
R2代表(C1-C6)烷基、(C2-C6)烯基、(C2-C6)炔基、(C3-C6)环烷基、(C3-C6)环烷基-(C1-C6)烷基、(C1-C6)烷基-O-(C1-C6)烷基、苯基、苯基-(C1-C6)烷基、杂芳基、(C1-C6)烷基-杂芳基、杂环基、(C1-C6)烷基-杂环基、(C1-C6)烷基-O-杂芳基、(C1-C6)烷基-O-杂环基、(C1-C6)烷基-NR3-杂芳基或(C1-C6)烷基-NR3-杂环基,其中这些基团被s个选自氰基、卤素、硝基、OR3、S(O)nR4、N(R3)2、NR3OR3、NR3SO2R4、COR3、OCOR3、NR3COR3、CO2R3、CON(R3)2和(C1-C4)烷氧基-(C2-C6)烷氧基羰基的基团取代,且其中杂环基带有n个氧代基团,
R3代表氢、(C1-C6)烷基、(C2-C6)烯基、(C2-C6)炔基、(C3-C6)环烷基或(C3-C6)环烷基-(C1-C6)烷基,
R4代表(C1-C6)烷基、(C2-C6)烯基或(C2-C6)炔基,
R5代表甲基或乙基,
R6代表OCOOR4、NR4COOR4、S(O)n-(C1-C6)烷基、S(O)n-(C1-C6)卤代烷基、硝基、氰基、SiR5 3、PO(OR5)2或带有m个氧代基团的杂环基,
m代表1或2,
n代表0、1或2,
s代表0、1、2或3,
u代表1、2、3、4或5。
特别优选式(I)的化合物,其中
A代表N或CY,
B代表N或CH,
X代表硝基、卤素、氰基、(C1-C6)烷基、卤代-(C1-C6)烷基、(C3-C6)环烷基、OR1、S(O)nR2、(C1-C6)烷基-S(O)nR2、(C1-C6)烷基-OR1、(C1-C6)烷基-CON(R1)2、(C1-C6)烷基-SO2N(R1)2、(C1-C6)烷基-NR1COR1、(C1-C6)烷基-NR1SO2R2、(C1-C6)烷基-杂芳基、(C1-C6)烷基-杂环基,其中最后提及的2个基团各自被s个选自卤素、(C1-C6)烷基、卤代-(C1-C6)烷基、S(O)n-(C1-C6)烷基、(C1-C6)烷氧基、卤代-(C1-C6)烷氧基的基团取代,且其中杂环基带有n个氧代基团,
Y代表氢、硝基、卤素、氰基、(C1-C6)烷基、(C1-C6)卤代烷基、OR1、S(O)nR2、SO2N(R1)2、N(R1)2、NR1SO2R2、NR1COR1、(C1-C6)烷基-S(O)nR2、(C1-C6)烷基-OR1、(C1-C6)烷基-CON(R1)2、(C1-C6)烷基-SO2N(R1)2、(C1-C6)烷基-NR1COR1、(C1-C6)烷基-NR1SO2R2、(C1-C6)烷基-苯基、(C1-C6)烷基-杂芳基、(C1-C6)烷基-杂环基、苯基、杂芳基或杂环基,其中最后提及的6个基团各自被s个选自卤素、硝基、氰基、(C1-C6)烷基、卤代-(C1-C6)烷基、(C3-C6)环烷基、S(O)n-(C1-C6)烷基、(C1-C6)烷氧基、卤代-(C1-C6)烷氧基、(C1-C6)烷氧基-(C1-C4)烷基和氰甲基的基团取代,且其中杂环基带有n个氧代基团,
Z代表卤素、氰基、卤代-(C1-C6)烷基、(C3-C6)环烷基、S(O)nR2、1,2,4-三唑-1-基,或在Y代表基团S(O)nR2时,Z还可代表氢、甲基、甲氧基或乙氧基,
R代表CH2R6,
CH2-杂环基,其中杂环基带有m个氧代基团,
(C2-C6)烷基、(C3-C7)环烷基、卤代-(C2-C6)烷基、(C2-C6)烯基、卤代-(C2-C6)烯基、(C2-C6)炔基或卤代-(C2-C6)炔基,所述基团各自被u个选自硝基、氰基、羟基、氧代、SiR5 3、PO(OR5)2、S(O)n-(C1-C6)烷基、(C1-C6)烷氧基、卤代-(C1-C6)烷氧基、N(R3)2、COR3、OCOR3、NR3COR3、NR3SO2R4、(C3-C6)环烷基、杂芳基、杂环基、苯基、Q-杂芳基、Q-杂环基、Q-苯基和Q-苄基的基团取代,其中所述基团(C3-C6)环烷基、杂芳基、杂环基、苯基、Q-杂芳基、Q-杂环基、Q-苯基和Q-苄基各自被s个选自甲基、乙基、甲氧基、氰基、硝基、三氟甲基和卤素的基团取代,且其中杂环基和环烷基带有n个氧代基团,
Q代表O、S或NR3,
R1代表氢、(C1-C6)烷基、(C2-C6)烯基、(C2-C6)炔基、(C3-C6)环烷基、(C3-C6)环烷基-(C1-C6)烷基、(C1-C6)烷基-O-(C1-C6)烷基、苯基、苯基-(C1-C6)烷基、杂芳基、(C1-C6)烷基-杂芳基、杂环基、(C1-C6)烷基-杂环基、(C1-C6)烷基-O-杂芳基、(C1-C6)烷基-O-杂环基、(C1-C6)烷基-NR3-杂芳基或(C1-C6)烷基-NR3-杂环基,其中最后提及的16个基团被s个选自氰基、卤素、硝基、OR3、S(O)nR4、N(R3)2、NR3OR3、COR3、OCOR3、NR3COR3、NR3SO2R4、CO2R3、CON(R3)2和(C1-C4)烷氧基-(C2-C6)烷氧基羰基的基团取代,且其中杂环基带有n个氧代基团,
R2代表(C1-C6)烷基、(C3-C6)环烷基或(C3-C6)环烷基-(C1-C6)烷基,其中以上提及的3个基团各自被s个选自卤素和OR3的基团取代,
R3代表氢或(C1-C6)烷基,
R4代表(C1-C6)烷基,
R5代表甲基或乙基,
R6代表OCOOR4、NR4COOR4、S(O)n-(C1-C6)烷基、S(O)n-(C1-C6)卤代烷基、硝基、氰基、SiR5 3、PO(OR5)2,
m代表1或2,
n代表0、1或2,
s代表0、1、2或3,
u代表1、2、3、4或5。
在所有如下给出的式中,除另有定义外,取代基和符号具有如式(I)所描述的相同的含义。
本发明的化合物可例如通过方案1给出的方法由苯甲酰氯(II)与5-氨基-1-H-1,2,4-三唑或5-氨基-1H-四唑(III)的碱催化反应而制备:
方案1
式(II)的苯甲酰氯或其所基于的苯甲酸为原则上已知的且可例如根据US6,376,429B1、EP1585742A1和EP1202978A1中描述的方法制备。
本发明的化合物还可通过方案2给出的方法通过使式(IV)苯甲酸与5-氨基-1-H-1,2,4-三唑或5-氨基-1H-四唑(III)反应而制备:
方案2
对于活化反应,可使用通常用于酰胺化反应的脱水剂,例如1,1`-羰基二咪唑(CDI)、二环己基碳二亚胺(DCC)、2,4,6-三丙基-1,3,5,2,4,6-三氧杂三膦杂环己烷2,4,6-三氧化物(T3P)等。
本发明的化合物还可通过方案3给出的方法通过使N-(1H-1,2,4-三唑-5-基)苯甲酰胺、N-(1H-四唑-5-基)苯甲酰胺、N-(1H-1,2,4-三唑-5-基)烟酰胺或N-(1H-四唑-5-基)烟酰胺反应而制备:
方案3
对于方案3给出的反应,可在碱的存在下使用例如烷基化剂如烷基卤化物、烷基磺酸盐或二烷基硫酸盐。
改变反应步骤的顺序可能是有利的。因此,带有亚砜的苯甲酸不能直接转化为其酰氯。本文中,适当地,在硫醚阶段,首先制备出酰胺然后使该硫醚氧化为亚砜。
可以类似于从文献中已知的方法制备式(III)的5-氨基-1H-四唑。例如,可根据Journal of the American Chemical Society(1954),76,923-924中描述的方法由氨基四唑制备5-氨基-1-R-四唑:
在以上提及的式中,R代表例如烷基。
可例如如Journal of the American Chemical Society(1954)76,88-89所述合成5-氨基-1-R-四唑:
可以类似于从文献已知的方法制备式(III)的5-氨基-IH-三唑。例如,可根据Zeitschrift für Chemie(1990),30(12),436-437中描述的方法由氨基三唑制备5-氨基-1-R-三唑:
还可如Chemische Berichte(1964),97(2),396-404所述合成5-氨基-1-R-三唑:
还可如Angewandte Chemie(1963),75,918所述合成5-氨基-1-R-三唑:
可以通过上述反应合成的式(I)化合物和/或其盐的集合也可以以并行的方式制备,为此可以手动、半自动或全自动方式进行。在这-方面,可以例如使反应过程、后处理或产物和/或中间体的纯化自动化。总而言之,这应理解为意指例如由D.Tiebes在Combinatorial Chemistry-Synthesis,Analysis,Screening(editor Günther Jung),Verlag Wiley1999,on pates1-34中所描述的过程。
对于并行的反应过程和后处理,可使用-系列市售仪器,例如购自Barnstead International,Dubuque,Iowa52004-0797,USA的Calpyso反应模块,或购自Radleys,Shirehill,Saffron Walden,Essex,CB113AZ,England的反应站,或购自Perkin Elmer,Waltham,Mass achusetts02451,USA的多探针(MultiPROBE)自动化工作站。对于通式(I)的化合物及其盐或制备过程中产生的中间体的并行纯化,尤其可以使用购自ISCO,Inc.,4700Superior Street,Lincoln,NE68504,USA的色谱装置。
所列装置可进行模块化操作,其中各个单独的方法步骤自动进行,但是在各方法步骤之间必须进行手动操作。这可通过使用半集成或全集成自动化系统——其中各自动化模块由例如机器人操控——而避免。这种自动化系统可购自例如Caliper,Hopkinton,MA01748,USA。
单个或多个合成步骤的实施可通过使用聚合物负载试剂/清除树脂(scavenger resin)来支持。专业文献描述了一系列实验方案,例如在ChemFiles,Vol.4,No.1,Polymer-Supported Scavengers and Reagentsfor Solution-Phase Synthesis(Sigma-Aldrich)中描述的。
除了本文所述的方法之外,通式(I)的化合物及其盐的制备可以完全或部分地通过固相负载法进行。为此,将所述合成或适用于相应方法的合成中的单独中间体或全部中间体结合至合成树脂上。固相负载合成法在专业文献中进行了充分描述,例如Barry A.Bunin在“TheCombinatorial Index”,Verlag Academic Press,1998和CombinatorialC hemistry-Synthesis,Analysis,Screening(editor Günther Jung),Verlag Wiley,1999中描述的。使用固相负载合成法可以实施文献中已知的-系列方案,这些方案也可以手动或以自动的方式进行。所述反应可以例如使用IRORI技术在购自Nexus Biosystems,12140CommunityRoad,Poway,CA92064,USA的微反应器中进行。
在固相上和在液相中进行单个或多个合成步骤可通过使用微波技术进行支持。专业文献中描述了一系列实验方案,例如在Microwaves inOrganic and Medicinal Chemistry(editor C.O.Kappe and A.Stadler),Verlag Wiley,2005中。
根据本文所述方法的制备产生物质集合形式的式(I)化合物及其盐,所述物质集合称为库(library)。本发明还提供包括至少两种式(I)化合物及其盐的库。
本发明的式(I)化合物(和/或其盐)在下文中也统称为“本发明的化合物”,其对广谱的经济上重要的单子叶和双子叶一年生有害植物具有优异的除草效力。所述活性化合物甚至有效地作用于从根茎、根状茎和其他多年生器官中发芽且难以防治的多年生有害杂草。
因此,本发明还涉及防治不需要的植物或用于调节植物的生长(优选用于作物植物中)的方法,其中将本发明的一种或多种化合物施用于植物(例如有害植物,例如单子叶或双子叶杂草或不需要的作物植物)、施用于种子(例如谷物、种子或无性繁殖体如块茎或带芽的幼枝部位)或施用于植物生长的区域(例如耕种区域)。在该上下文中,本发明化合物可以例如在播种前(如果合适,也可以混入土壤中)、发芽前或发芽后施用。可提及一些可通过本发明的化合物防治的单子叶和双子叶杂草群的代表作为具体实例,而以下的列举并不限定于特定物种。
以下属的单子叶有害植物:山羊草属(Aegilops)、冰草属(Agropyron)、剪股颖属(Agrostis)、看麦娘属(Alopecurus)、Apera属、燕麦属(Avena)、臂形草属(Brachiaria)、雀麦属(Bromus)、蒺藜草属(Cenchrus)、鸭跖草属(Commelina)、狗牙根属(Cynodon)、莎草属(Cyperus)、龙爪茅属(Dactyloctenium)、马唐属(Digitaria)、稗属(Echinochloa)、荸荠属(Eleocharis)、蟋蟀草属(Eleusine)、画眉草属(Eragrostis)、野黍属(Eriochloa)、羊茅属(Festuca)、飘拂草属(Fimbristylis)、异蕊花属(Heteranthera)、白茅属(Imperata)、鸭嘴草属(Ischaemum)、千金子属(Leptochloa)、黑麦草属(Lolium)、雨久花属(Monochoria)、黍属(Panicum)、雀稗属(Paspalum)、虉草属(Phalaris)、梯牧草属(Phleum)、早熟禾属(Poa)、筒轴茅属(Rottboellia)、慈姑属(Sagittaria)、莞草属(Scirpus)、狗尾草属(Setaria)、高粱属(Sorghum)。
以下属的双子叶杂草:苘麻属(Abutilon)、苋属(Amaranthus)、豚草属(Ambrosia)、Anoda属、春黄菊属(Anthemis)、Aphanes属、艾属(Artemisia)、滨藜属(Atriplex)、雏菊属(Bellis)、鬼针属(Bidens)、荠属(Capsella)、飞廉属(Carduus)、决明属(Cassia)、矢车菊属(Centaurea)、藜属(Chenopodium)、蓟属(Cirsium)、旋花属(Convolvulus)、曼陀罗属(Datura)、山蚂蝗属(Desmodium)、刺酸模属(Emex)、糖芥属(Erysimum)、大戟属(Euphorbia)、鼬瓣花属(Galeopsis)、牛膝菊属(Galinsoga)、猪殃殃属(Galium)、芙蓉属(Hibiscus)、番薯属(Ipomoea)、地肤属(Kochia)、野芝麻属(Lamium)、独行菜属(Lepidium)、母草属(Lindernia)、母菊属(Matricaria)、薄荷属(Mentha)、山靛属(Mercurialis)、Mullugo属、勿忘我属(Myosotis)、罂粟属(Papaver)、牵牛属(Pharbitis)、车前属(Plantago)、蓼属(Polygonum)、马齿苋属(Portulaca)、毛茛属(Ranunculus)、萝卜属(Raphanus)、蔊菜属(Rorippa)、节节菜属(Rotala)、酸模属(Rumex)、猪毛菜属(Salsola)、千里光属(Senecio)、田菁属(Sesbania)、黄花稔属(Sida)、白芥属(Sinapis)、茄属(Solanum)、苦苣菜属(Sonchus)、尖瓣花属(Sphenoclea)、繁缕属(Stellaria)、蒲公英属(Taraxacum)、菥蓂属(Thlaspi)、车轴草属(Trifolium)、荨麻属(Urtica)、婆婆纳属(Veronica)、堇菜属(Viola)、苍耳属(Xanthium)。
如果在发芽前将本发明的化合物施用至土壤,则完全阻止杂草幼苗的发芽,或者使得杂草幼苗生长至达到子叶期,但之后它们停止生长,并最终在三至四周后完全死亡。
如果在发芽后将所述活性化合物施用至植物的绿色部位,则在处理后生长停止,并且有害植物停留在施用时间点的生长阶段,或者其在一段时间后完全死亡,从而以这种方式在非常早的时期并以持续的方式消除对作物植物有害的杂草带来的竞争。
尽管本发明的化合物表现出出色的对单子叶和双子叶杂草的除草活性,但是经济上重要的作物中的作物植物仅受到微小程度的损害,或者完全不受到损害,这取决于本发明各化合物的结构和其施用率,所述经济上重要的作物中的作物植物例如以下属的双子叶作物:花生属(Arachis)、甜菜属(Beta)、芸苔属(Brassica)、黄瓜属(Cucumis)、南瓜属(Cucurbita)、向日葵属(Helianthus)、胡萝卜属(Daucus)、大豆属(Glycine)、棉属(Gossypium)、番薯属(Ipomoea),莴苣属(Lactuca),亚麻属(Linum)、番茄属(Lycopersicon)、烟草属(Nicotiana)、菜豆属(Phaseolus)、豌豆属(Pisum)、茄属(Solanum)、蚕豆属(Vicia),或以下属的单子叶作物:葱属(Allium)、凤梨属(Ananas)、天门冬属(Asparagus)、燕麦属(Avena)、大麦属(Hordeum)、稻属(Oryza)、黍属(Panicum)、甘蔗属(Saccharum)、黑麦属(Secale)、高粱属(Sorghum)、小黑麦属(Triticale)、小麦属(Triticum)、玉蜀黍属(Zea),特别是玉蜀黍属和小麦属。这就是为什么本发明化合物极适用于在作物植物例如农业有用植物或观赏植物中选择性防治不想要的植物生长的原因。
此外,本发明的化合物(取决于它们各自的结构和施用的施用率)在作物植物中具有出色的生长调节性能。它们以调节的方式参与植物的新陈代谢,并且因此可以用于以靶向方式影响植物的成分,以及用于促进采收,例如通过引发脱水和使植株矮小生长。此外,它们通常也适用于防治和抑制不想要的营养生长而在此过程中不破坏植物。据此,抑制营养生长由于例如可以减少或完全防止倒伏而在许多单子叶和双子叶作物中起到非常重要的作用。
由于它们的除草活性和植物生长调节活性,所述活性化合物也可用于防治转基因植物作物中或通过常规诱变而改性的植物作物中的有害植物。一般地,转基因植物特征在于具有一些特别有利的性质,例如对某些农药的抗性,主要是对于某些除草剂的抗性,对于植物病害或植物病害的致病微生物——例如某些昆虫或微生物,例如真菌、细菌或病毒——的抗性。其他特定性质涉及到例如采收物的产量、质量、储存性、组成和特定成分。因此,淀粉含量增加、或淀粉品质改变,或者是在采收物中具有不同的脂肪酸组成的转基因植物是已知的。
关于转基因作物,优选在经济上重要的有用植物和观赏性植物的转基因作物中使用本发明的化合物,所述作物例如谷物,例如小麦、大麦、黑麦、燕麦、黍、稻和玉米,或者甜菜、棉花、大豆、油菜、马铃薯、番茄、豌豆以及其他蔬菜的作物。优选将本发明的化合物作为除草剂用在对除草剂的植物毒性作用具有抗性或已通过重组方式产生抗性的有用植物作物中。
优选在经济上重要的有用植物和观赏性植物的的转基因作物中使用本发明的化合物或其盐,所述作物例如谷物,例如小麦、大麦、黑麦、燕麦、黍、稻、木薯和玉米,或者甜菜、棉花、大豆、油菜、马铃薯、番茄、豌豆以及其他蔬菜的作物。优选将本发明的化合物作为除草剂用在对除草剂的植物毒性作用具有抗性或已通过重组方式产生抗性的有用植物作物中。
与已有植物相比,产生具有改进特性的新植物的常规方法包括例如常规育种方法和突变体产生法。或者,具有改进特性的新植物可借助重组方法培育(参见例如,EP-A-0221044、EP-A-0131624)。例如,在一些方案中描述了以下方法:
-通过重组技术修饰作物植物,目的是对植物中合成的淀粉进行改性(例如WO92/11376、WO92/14827、WO91/19806),
-对草铵磷(glufosinate)类(参见例如EP-A-0242236、EP-A-242246)或草甘膦(gluphosate)类(WO92/00377)或磺酰脲类(EP-A-0257993、US-A-5013659)的某些除草剂具有抗性的转基因作物植物,
-能产生苏云金杆菌毒素(Bt毒素)的转基因作物植物(例如棉花),其使植物对某些害虫具有抗性(EP-A-0142924、EP-A-0193259),
-具有改变的脂肪酸组成的转基因作物植物(WO91/13972),
-具有新成分或次级代谢产物(例如新型植物抗毒素,其能够带来增强的抗病能力)的基因修饰作物植物(EPA309862、EPA0464461),
-具有减少的光呼吸的基因修饰植物,其具有更高产量和更高胁迫耐受性的特性(EPA0305398),
-生产药学上或诊断学上重要的蛋白质的转基因作物植物(“分子药用”)。
-特征在于更高产量或更好品质的转基因作物,
-特征在于例如上述新的特性的结合(“基因叠加”)的转基因作物。
许多借助其能够产生具有改进性能的新型转基因植物的分子生物技术原则上是已知的;参见例如I.Potrykus and G.Spangenberg(eds.)GeneTransfer to Plants,Springer Lab Manual(1995),Springer Verlag Berlin,Heidelberg.或者Christou,″Trends in Plant Science″1(1996)423-431。
为了实施这种重组操作,可以将能够产生突变或通过重组DNA序列产生序列改变的核酸分子引入质粒。借助于标准方法,可以例如进行碱基取代、可以移除部分序列或可以加入天然的或合成的序列。为了将DNA片段彼此连接,可以向片段加入接头(adapter)或连接体(linker);参见例如,Sambrook et al.,1989,Molecular Cloning,A Laboratory Manual,2nd ed.,Cold Spring Harbor Laboratory Press,Cold Spring Harbor,NY;或Winnacker″Gene und Klone″,VCH Weinheim2nd ed.,1996。
例如,基因产物活性降低的植物细胞的产生可以通过下列方法实现:通过表达至少一种相应的反义RNA、用于实现共抑制作用的正义RNA,或者通过表达至少一种特异性切割上述基因产物的转录物的合适地构建的核酶。为此,可使用包含基因产物的全部编码序列(包括可能存在的任意侧翼序列)的DNA分子,还可使用仅包括一部分编码序列的DNA分子,这些部分必须足够长以在细胞中产生反义作用。也可以使用与基因产物的编码序列具有高度同源性但并不完全与其相同的DNA序列。
当在植物中表达核酸分子时,所合成的蛋白可被定位在植物细胞的任何所需的区室中。然而,为了实现在特定区室中的定位,可以例如将编码区与在特定区室中确保定位的DNA序列相连接。这种序列是本领域中技术人员已知的(参见例如Braun et al.,EMBO J.11(1992),3219-3227;Wolter et al.,Proc.Natl.Acad.Sci.USA85(1988),846-850;Sonnewald etal.,Plant J.1(1991),95-106)。核酸分子也可以在植物细胞中的细胞器中表达。
转基因植物细胞可以通过已知技术再生以长成完整的植物。原则上,所述转基因植物可为任何所需植物品种的植物,即不仅可为单子叶植物,还可为双子叶植物。
因此,性质改变的转基因植物可以通过对同源(=天然)基因或基因序列的过表达、阻遏或抑制而获得,或者通过异源(=外源)基因或基因序列的表达而获得。
优选将本发明的化合物施用于转基因作物中,所述施转基因作物对如下物质具有抗性:生长调节剂,例如麦草畏;或者抑制重要的植物酶的除草剂,所述植物酶例如乙酰乳酸合成酶(ALS)、EPSP合成酶、谷氨酰胺合成酶(GS)或羟基苯丙酮酸双加氧酶(HPPD);或者选自磺酰脲、草甘膦、草铵磷或苯甲酰基异噁唑以及类似的活性化合物的除草剂。
当将本发明的活性化合物用在转基因作物中时,除了可在其他作物中观察到的对于有害植物的作用之外,还经常观察到对施用于所述转基因作物的特异性作用,例如改变或特别是拓宽的可以防治的杂草谱、改进的施用时可使用的施用率、与转基因作物对其有抗性的除草剂的更好的相容性,以及对转基因作物植物的生长和产量的作用。
因此,本发明还涉及本发明的化合物作为除草剂用于防治转基因作物中的有害植物的用途。
本发明的化合物可以可湿性粉剂、悬乳浓缩剂、可喷洒溶液剂、粉剂或颗粒剂的形式用在常规制剂中。因此,本发明还提供含有本发明的化合物的除草和植物生长调节组合物。
本发明的化合物可以多种方式根据其所需的生物学和/或物理化学参数进行配制。可用的制剂包括,例如:可湿性粉剂(WP)、水溶性粉剂(SP)、水溶性浓缩剂、悬乳浓缩剂(EC)、乳剂(EW)例如水包油乳剂和油包水乳剂、可喷洒溶液剂、悬浮浓缩剂(SC)、油基分散剂或水基分散剂、油混溶性溶液剂、胶囊悬浮剂(CS)、粉剂(DP)、拌种产品、用于撒播和土壤施用的颗粒剂、呈微颗粒形式的颗粒剂(GR)、喷洒颗粒剂、包衣颗粒剂和吸附颗粒剂、水分散性颗粒剂(WG)、水溶性颗粒剂(SG)、ULV制剂、微胶囊剂和蜡剂。这些制剂的各个类型原则上均是已知的,并描述于例如:Winnacker-Küchler,″ChemischeTechnologie″[Chemical technology],Volume7,C.Hanser VerlagMunich,4th Ed.1986、Wade van Valkenburg,″PesticideFormulations″,Marcel Dekker,N.Y.,1973、K.Martens,″SprayDrying″Handbook,3rd Ed.1979,G.Goodwin Ltd.London中。
必要的制剂助剂,例如惰性物质、表面活性剂、溶剂和其他添加剂同样是已知的,并描述于例如:Watkins,″Handbook of Insecticide DustDiluents and Carriers″,2nd Ed.,Darland Books、Caldwell N.J.,H.v.Olphen,″Introduction to Clay Colloid Chemistry″;2nd Ed.,J.Wiley&Sons,N.Y.、C.Marsden,″Solvents Guide″;2nd Ed.,Interscience,N.Y.1963、McCutcheon′s″Detergents and Emulsifiers Annual″.MCPubl.Corp.、Ridgewood N.J.;Sisley and Wood,″Encyclopedia ofSurface Active Agents″,Chem.Publ.Co.Inc.,N.Y.1964、″″[Interface-active ethyleneoxide adducts],Wiss.Verlagsgesell.,Stuttgart1976、Winnacker-Küchler,″Chemische Technologie″,Volume7,C.HanserVerlag Munich,4th Ed.1986中。
基于这些制剂,可以制备与其它农药活性物质(例如杀昆虫剂、杀螨剂、除草剂和杀真菌剂)以及与安全剂、肥料和/或生长调节剂的结合物,例如呈成品制剂或桶混形式。合适的安全剂为例如吡唑解草酯(mefenpyr-diethyl)、环丙磺酰胺(cyprosulfamid)、双苯恶唑酸(isoxadifen-ethyl)、解草酯(cloquintocet-mexyl)和二氯丙烯胺(dichlormid)。
可湿性粉剂为可均匀分散于水中的制剂,并且其除了活性化合物以外,还含有除稀释剂或惰性物质之外的离子型表面活性剂和/或非离子型表面活性剂(润湿剂、分散剂),例如聚氧乙基化烷基酚、聚氧乙基化脂肪醇、聚氧乙基化脂肪胺、脂肪醇聚乙二醇醚硫酸盐、烷基磺酸盐、烷基苯磺酸盐、木素磺酸钠、2,2’-二萘基甲烷-6,6’-二磺酸钠、二丁基萘磺酸钠或油酰基甲基牛磺酸钠。为了制备可湿性粉剂,例如在常规设备例如锤磨机、鼓风磨机和喷气磨机中精细研磨具有除草活性的化合物,并同时或随后与制剂助剂相混合。
悬乳浓缩剂通过下述过程制备:将活性化合物溶于有机溶剂(例如丁醇、环己酮、二甲基甲酰胺、二甲苯或相对高沸点的芳香族化合物或烃)或有机溶剂混合物中,并加入一种或多种离子型和/或非离子型表面活性剂(乳化剂)。使用的乳化剂可为例如烷基芳基磺酸钙盐,例如十二烷基苯磺酸钙;或非离子型乳化剂,例如脂肪酸聚乙二醇酯、烷基芳基聚乙二醇醚、脂肪醇聚乙二醇醚、环氧丙烷-环氧乙烷缩合物、烷基聚醚、脱水山梨糖醇酯,例如脱水山梨糖醇脂肪酸酯或聚氧乙烯脱水山梨糖醇酯例如聚氧乙烯脱水山梨糖醇脂肪酸酯。
粉剂可通过将活性化合物与细分散的固体物质一起研磨而制备,所述固体物质例如滑石、天然粘土例如高岭土、膨润土和叶蜡石或硅藻土。
悬浮浓缩剂可为水基或油基的。其可以例如使用市售的球磨机通过湿法研磨制备,在制备过程中可以任选地加入例如上文针对其他剂型列出的表面活性剂。
乳剂,例如水包油乳剂(EW),可以通过例如搅拌器、胶体磨机和/或静态混合器使用水性有机溶剂以及任选的例如上文针对其他剂型列出的表面活性剂而制备。
颗粒剂可以通过将所述活性化合物喷洒在能够吸附的颗粒状惰性物质上而制备,或通过使用粘合剂将活性化合物浓缩物施用到载体物质表面而制备,所述载体物质例如砂、高岭土或颗粒状惰性材料,所述粘合剂例如聚乙烯醇、聚丙烯酸钠或矿物油。,则合适的活性化合物也可以以制备肥料颗粒的常规方式——如果需要、与肥料混合——制粒。
水分散性颗粒剂通常可通过常规方法制备,所述常规方法例如喷雾干燥法、流化床制粒法、盘式制粒法、使用高速混合器的混合法以及不使用固体惰性物质的挤出法。
对于盘式、流化床、挤出机和喷雾颗粒的制备,参见例如Spray-Drying Handbook″3rd ed.1979,G.Goodwin Ltd.,London;J.E.Browning,″Agglomeration″,Chemical and Engineering1967,pages147ff;″Perry′s Chemical Engineer′s Handbook″,5th Ed.,McGraw-Hill,New York1973,p.8-57中的方法。
关于作物保护组合物制剂的更多细节,参见例如G.C.Klingman,″Weed Control as a Science″,John Wiley and Sons,Inc.,New York,1961,pages81-96和J.D.Freyer,S.A.Evans,″Weed ControlHandbook″,5th Ed.,Blackwell Scientific Publications,Oxford,1968,pages101-103。
所述农业化学制剂通常含有0.1至99重量%、特别地为0.1至95重量%的本发明的化合物。
在可湿性粉剂中,活性化合物的浓度例如为约10至90重量%,至100重量%的剩余部分由常规制剂组分组成。对于悬乳浓缩剂,活性化合物的浓度可为约1至90重量%,优选为5至80重量%。粉剂形式的制剂含有1至30重量%的活性化合物,优选地通常含有5至20重量%的活性化合物;可喷洒溶液剂含有约0.05至80重量%、优选2至50重量%的活性化合物。对于水分散颗粒剂而言,活性化合物的含量部分取决于所述活性化合物以液体形式还是固体形式存在,以及取决于所使用的粒化助剂、填料等。在水分散性颗粒剂中,活性化合物的含量例如为1至95重量%,优选为10至80重量%。
此外,提及的活性化合物的制剂任选地含有各自常用的粘合剂、润湿剂、分散剂、乳化剂、渗透剂、防腐剂、抗冻剂和溶剂、填料、载体和染料、消泡剂、蒸发抑制剂和影响pH值及粘度的试剂。
基于这些制剂,可生产与其他农药活性物质(例如杀昆虫剂、杀螨剂、除草剂和杀真菌剂)以及与安全剂、肥料和/或生长调节剂的结合物,例如呈成品制剂或桶混物的形式。
可以与本发明的化合物以混合制剂或桶混形式结合使用的活性化合物为,例如,已知的基于抑制例如以下物质的活性化合物:乙酰乳酸合成酶、乙酰辅酶A羧化酶、纤维素合成酶、烯醇式丙酮酰莽草酸-3-磷酸合成酶、谷氨酰胺合成酶、对羟基苯基丙酮酸双加氧酶、八氢番茄红素去饱和酶、光系统I、光系统II、原卟啉原氧化酶,如记载于例如Weed Research26(1986)441-445或″The Pesticide Manual″,15th edition,The BritishCrop Protection Council and the Royal Soc.of Chemistry,2009中和其中引用的文献中的。可以与本发明的化合物结合的已知的除草剂或植物生长调节剂为例如以下活性物质(化合物以国际标准化组织(ISO)规定的通用名表示,或以化学名称或其编号表示),且其总是包括所有使用形式,例如包括酸、盐、酯和异构体例如立体异构体和旋光异构体。本文中,以示例的方式提及一种使用形式以及在一些情况下的多种使用形式:乙草胺(acetochlor)、acibenzolar、acibenzolar-S-methyl、三氟羧草醚(acifluorfen)、三氟羧草醚(acifluorfen-sodium)、苯草醚(aclonifen)、甲草胺(alachlor)、草毒死(allidochlor)、禾草灭(alloxydim)、枯杀达(alloxydim-sodium)、莠灭净(ametryn)、氨唑草酮(amicarbazone)、先甲草胺(amidochlor)、酰嘧磺隆(amidosulfuron)、环丙嘧啶酸(aminocyclopyrachlor)、氯氨吡啶酸(aminopyralid)、杀草强(amitrole)、氨基磺酸铵(ammonium sulfamate)、环丙嘧啶醇(ancymidol)、莎稗磷(anilofos)、磺草灵(asulam)、莠去津(atrazine)、唑啶草酮(azafenidin)、四唑嘧磺隆(azimsulfuron)、叠氮津(aziprotryn)、氟丁酰草胺(beflubutamid)、草除灵(benazolin)、草除灵乙酯(benazolin-ethyl)、bencarbazone、乙丁氟灵(benfluralin)、呋草黄(benfuresate)、地散磷(bensulide)、bensulfuron、苄嘧磺隆(bensulfuron-methyl)、灭草松(bentazone)、双苯嘧草酮(benzfendizone)、双环磺草酮(benzobicyclon)、吡草酮(benzofenap)、氟磺胺草(benzofluor)、新燕灵(benzoylprop)、bicyclopyrone、甲羧除草醚(bifenox)、双丙氨膦(bilanafos)、双丙氨膦钠盐(bilanafos-sodium)、双草醚(bispyribac)、双草醚(bispyribac-sodium)、除草定(bromacil)、溴丁酰草胺(bromobutide)、溴酚肟(bromofenoxim)、溴苯腈(bromoxynil)、莠谷隆(bromuron)、特克草(buminafos)、羟草酮(busoxinone)、丁草胺(butachlor)、氟丙嘧草酯(butafenacil)、抑草磷(butamifos)、丁烯草胺(butenachlor)、仲丁灵(butralin)、丁氧环酮(butroxydim)、丁草敌(butylate)、唑草胺(cafenstrole)、双酰草胺(carbetamide)、唑酮草酯(carfentrazone)、唑酮草酯(carfentrazone-ethyl)、甲氧除草醚(chlomethoxyfen)、草灭畏(chloramben)、chlorazifop、chlorazifop-butyl、氯溴隆(chlorbromuron)、氯炔灵(chlorbufam)、伐草克(chlorfenac)、双氯酚酸钠(chlorfenac-sodium)、燕麦酯(chlorfenprop)、氯甲丹(chlorflurenol)、氯甲丹(chlorflurecol-methyl)、氯草敏(chloridazon)、氯嘧磺隆(chlorimuron)、氯嘧磺隆(chlorimuron-ethyl)、矮壮素(chlormeq uat chloride)、草枯醚(chlornitrofen)、4-氯邻苯二甲酸(chlorophthalim)、氯酞酸甲酯(chlorthal-dimethyl)、绿麦隆(chlorotoluron)、氯磺隆(chlorsulfuron)、cinidon、吲哚酮草酯(cinidon-ethyl)、环庚草醚(cinmethylin)、醚磺隆(cinosulfuron)、烯草酮(clethodim)、炔草酸(clodinafop)、炔草酯(clodinafop-propargyl)、杀雄嗪酸(clofencet)、异恶草松(clomazone)、氯甲酰草胺(clomeprop)、调果酸(cloprop)、二氯吡啶酸(clopyralid)、氯酯磺草胺(cloransulam)、氯酯磺草胺(cloransulam-methyl)、苄草隆(cumyluron)、氨基氰(cyanamide)、氰草津(cyanazine)、环丙酰胺酸(cyclanilide)、环草敌(cycloate)、环丙嘧磺隆(cyclosulfamuron)、噻草酮(cycloxydim)、环莠隆(cycluron)、氰氟草酯(cyhalofop)、氰氟草酯(cyhalofop-butyl)、莎草快(cyperquat)、环丙津(cyprazine)、环唑草胺(cyprazole)、2,4-D、2,4-DB、杀草隆(daimuron/dymron)、茅草枯(dalapon)、丁酰肼(daminozide)、棉隆(dazomet)、正癸醇(n-decanol)、甜菜安(desmedipham)、敌草净(desmetryn)、detosyl-pyrazolate(DTP)、燕麦敌(diallate)、麦草畏(dicamba)、敌草腈(dichlobenil)、2,4-滴丙酸(dichlorprop)、2,4-滴丙酸(dichlorprop-P)、二氯苯氧基丙酸(diclofop)、禾草灵(diclofop-methyl)、禾草灵(diclofop-P-methyl)、双氯磺草胺(diclosulam)、乙酰甲草酸(diethatyl)、乙酰甲草胺(diethatyl-ethyl)、枯莠隆(difenoxuron)、野燕枯(difenzoquat)、吡氟酰草胺(diflufenican)、二氟吡隆(diflufenzopyr)、氟吡草腙(diflufenzopyr-sodium)、恶唑隆(dimefuron)、敌草克(dikegulac-sodium)、恶唑隆(dimefuron)、哌草丹(dimepiperate)、二甲草胺(dimethachlor)、异戊乙净(dimethametryn)、二甲吩草胺(dimethenamid)、甲酚噻草胺-P(dimethenamide-P)、噻节因(dimethipin)、dimetrasulfuron、氨氟灵(dinitramine)、地乐酚(dinoseb)、特乐酚(dinoterb)、双苯酰草胺(diphenamid)、异丙净(dipropetryn)、敌草快(diquat)、敌草快(diquat dibromide)、氟硫草定(dithiopyr)、敌草隆(diuron)、二硝酚(DNOC)、草止津(eglinazine-ethyl)、茵多酸(endothal)、扑草灭(EPTC)、戊草丹(esprocarb)、乙丁烯氟灵(ethalfluralin)、胺苯磺隆(ethametsulfuron)、胺苯磺隆(ethametsulfuron-methyl)、乙烯利(ethephon)、磺噻隆(ethidimuron)、乙嗪草酮(ethiozin)、乙氧呋草黄(ethofumesate)、氟乳醚(ethoxyfen)、氯氟草醚乙酯(ethoxyfen-ethyl)、乙氧嘧磺隆(ethoxysulfuron)、乙氧苯草胺(etobenzanid)、F-5331即N[2-氯-4-氟-5[4-(3-氟丙基)4,5-二氢-5-氧代-1H-四唑-1-基]苯基]乙磺酰胺、F-7967即3-[7-氯-5-氟-2-(三氟甲基)1H-苯并咪唑-4-基]-1-甲基-6-(三氟甲基)嘧啶-2,4(1H,3H)二酮、2,4,5-涕丙酸(fenoprop)、噁唑禾草灵(fenoxaprop)、噁唑禾草灵(fenoxaprop-P)、噁唑禾草灵(fenoxaprop-ethyl)、精噁唑禾草灵(fenoxaprop-P-ethyl)、fenoxasulfone、四唑酰草胺(fentrazamide)、非草隆(fenuron)、麦草氟(flamprop)、麦草氟异丙酯(flamprop-M-isopropyl)、麦草氟甲酯(flamprop-M-methyl)、啶嘧磺隆(flazasulfuron)、双氟磺草胺(florasulam)、吡氟禾草灵(fluazifop)、精吡氟禾草灵(fluazifop-P)、吡氟禾草灵丁酯(fluazifop-butyl)、精吡氟禾草灵丁酯(fluazifop-P-butyl)、异丙吡草酯(fluazolate)、氟唑磺隆(flucarbazone)、氟酮磺隆(flucarbazone-sodium)、氟吡磺隆(flucetosulfuron)、氯乙氟灵(fluchloralin)、氟噻草胺(flufenacet(thiafluamide))、氟哒嗪草酯(flufenpyr)、氟哒嗪草酯(flufenpyr-ethyl)、氟节胺(flumetralin)、唑嘧磺草胺(flumetsulam)、氟烯草酸(flumiclorac)、氟烯草酸(flumiclorac-pentyl)、丙炔氟草胺(flumioxazin)、炔草胺(flumipropyn)、氟草隆(fluometuron)、三氟硝草醚(fluorodifen)、乙羧氟草醚(fluoroglycofen)、乙羧氟草醚(fluoroglycofen-ethyl)、氟胺草唑(flupoxam)、氟丙嘧草酯(flupropacil)、四氟丙酸(flupropanoate)、氟啶磺隆(flupyrsulfuron)、氟啶嘧磺隆(flupyrsulfuron-methyl-sodium))、抑草丁(flurenol)、芴丁酯(flurenol-butyl)、氟啶草酮(fluridone)、氟咯草酮(flurochloridone)、氟草烟(fluroxypyr)、甲基庚酯(fluroxypyr-meptyl)、呋嘧醇(flurprimidol)、呋草酮(flurtamone)、嗪草酸(fluthiacet)、氟噻乙草酯(fluthiacet-methyl)、噻唑草酰胺(fluthiamide)、氟磺胺草醚(fomesafen)、甲酰氨磺隆(foramsulfuron)、氯吡脲(forchlorfenuron)、杀木膦(fosamine)、呋氧草醚(furyloxyfen)、赤霉素(gibberillic acid)、草铵膦(glufosinate)、草铵磷(glufosinate-ammonium)、精草铵膦(glufosinate-P)、精草铵膦铵(glufosinate-P-ammonium)、精草铵膦钠(glufosinate-P-sodium)、草甘膦(glyphosate)、草甘膦异丙铵盐(glyphosate-isopropylammonium)、H-9201即O-(2,4-二甲基-6-硝基苯基)O-乙基-异丙基硫代磷酰胺酯、氟硝磺酰胺(halosafen)、氯吡嘧磺隆(halosulfuron)、氯吡嘧磺隆(halosulfuron-methyl)、氟吡禾灵(haloxyfop)、精氟吡禾灵(haloxyfop-P)、氯氟乙禾灵(haloxyfop-ethoxyethyl)、氯氟乙禾灵(haloxyfop-P-ethoxyethyl)、氟吡甲禾灵(haloxyfop-methyl)、氟吡甲禾灵(haloxyfop-P-methyl)、环嗪酮(hexazinone)、HW-02即1-(二甲氧基磷酰基)乙基(2,4-二氯苯氧基)乙酸酯、咪草酸(imazamethabenz)、咪草酸(imazamethabenz-methyl)、甲氧咪草烟(imazamox)、甲氧咪草烟酸铵(imazamox-ammonium)、甲咪唑烟酸(imazapic)、咪唑烟酸(imazapyr)、咪唑烟酸异丙铵(imazapyr-isopropylammonium)、咪唑喹啉酸(imazaquin)、咪唑喹啉酸铵(imazaq uin-ammonium)、咪唑乙烟酸(imazethapyr)、咪唑乙烟酸铵(imazethapyr-ammonium)、唑吡嘧磺隆(imazosulfuron)、抗倒胺(inabenfide)、茚草酮(indanofan)、碘甲磺隆(indaziflam)、吲哚乙酸(indoleacetic acid(IAA))、4-吲哚-3-基丁酸(IBA)、碘甲磺隆钠盐(iodosulfuron)、碘甲磺隆钠盐(iodosulfuron-methyl-sodium)、碘苯腈(ioxynil)、三哇苯胺除草剂(ipfencarbazone)、丁脒酰胺(isocarbamid)、异丙乐灵(isopropalin)、异丙隆(isoproturon)、异恶隆(isouron)、异恶酰草胺(isoxaben)、异恶氯草酮(isoxachlortole)、异噁唑草酮(isoxaflutole)、异恶草醚(isoxapyrifop)、IKUH-043即3-({[5-(二氟甲基)1-甲基-3-(三氟甲基)1H-吡唑-4-基]甲基}磺酰基)5,5-二甲基-4,5--二氢-1,2-噁唑、特胺灵(karbutilate)、ketospiradox、乳氟禾草灵(lactofen)、环草定(lenacil)、利谷隆(linuron)、马来酰肼(maleic hydrazide)、MCPA、MCPB、MCPB甲酯(MCPB-methyl)、MCPB乙酯(MCPB-ethyl)和MCPB钠(MCPB-sodium)、2-甲-4-氯丙酸(mecoprop)、2-甲-4-氯丙酸钠(mecoprop-sodium)、2-甲-4-氯丙酸丁氧酯(mecoprop-butotyl)、高-2-甲-4-氯丙酸丁氧酯(mecoprop-P-butotyl)、高-2-甲-4-氯丙酸二甲铵(mecoprop-P-dimethylammonium)、高-2-甲-4-氯丙酸2-乙基己酯(mecoprop-P-2-ethylhexyl)、高-2-甲-4-氯丙酸钾(mecoprop-P-potassium)、苯噻酰草胺(mefenacet)、氯磺酰草胺(mefluidide)、甲哌啶(mepiq uat chloride)、甲磺胺磺隆(mesosulfuron)、甲磺胺磺隆(mesosulfuron-methyl)、甲基磺草酮(mesotrione)、甲基苯噻隆(methabenzthiazuron)、威百亩(metam)、噁唑酰草胺(metamifop)、苯嗪草酮(metamitron)、吡唑草胺(metazachlor)、双醚氯吡嘧磺隆(metazosulfuron)、灭草唑(methazole)、甲硫嘧磺隆(methiopyrsulfuron)、methiozolin、苯草酮(methoxyphenone)、甲基杀草隆(methyldymron)、1-甲基环丙烯(1-methylcyclopropene)、异硫氰酸甲酯(methyl isothiocyanate)、吡喃隆(metobenzuron)、溴谷隆(metobromuron)、异丙甲草胺(metolachlor)、S-异丙甲草胺(S-metolachlor)、磺草唑胺(metosulam)、甲氧隆(metoxuron)、嗪草酮(metribuzin)、甲磺隆(metsulfuron)、甲磺隆(metsulfuron-methyl)、禾草敌(molinate)、庚酰草胺(monalide)、单脲(monocarbamide)、甲酰胺硫酸盐(monocarbamide dihydrogensulfate)、绿谷隆(monolinuron)、单嘧磺隆(monosulfuron)、单嘧磺酯(monosulfuron-easter)、灭草隆(monuron)、MT128即6-氯-N-[(2E)3-氯丙-2-烯-1-基]-5-甲基-N-苯基哒嗪-3-胺、MT-5950即N[3-氯-4-(1-甲基乙基)苯基]2-甲基戊酰胺、NGGC-011、萘丙胺(naproanilide)、敌草胺(napropamide)、萘草胺(naptalam)、NC310即4-(2,4-二氯苯甲酰基)1-甲基-5-苄氧基吡唑、草不隆(neburon)、烟嘧磺隆(nicosulfuron)、氟氯草胺(nipyraclofen)、甲磺乐灵(nitralin)、除草醚(nitrofen)、复硝酚钠(nitrophenolate-sodium)(异构体混合物)、硝氟草醚(nitrofluorfen)、正壬酸(nonanoic acid)、氟草敏(norflurazon)、坪草丹(orbencarb)、嘧苯胺磺隆(orthosulfamuron)、氨磺乐灵(oryzalin)、丙炔恶草酮(oxadiargyl)、恶草酮(oxadiazon)、环氧嘧磺隆(oxasulfuron)、恶嗪草酮(oxaziclomefone)、乙氧氟草醚(oxyfluorfen)、多效唑(paclobutrazol)、百草枯(paraquat)、百草枯(paraquat-dichloride)、壬酸(pelargonic acid(nonanoic acid))、二甲戊灵(pendimethalin)、4-(叔丁基)N-(1-乙基-丙基)-2,6-二硝基-苯胺(pendralin)、五氟磺草胺(penoxsulam)、甲氯酰草胺(pentanochlor)、环戊恶草酮(pentoxazone)、黄草伏(perfluidone)、烯草胺(pethoxamid)、棉胺宁(phenisopham)、甜菜宁(phenmedipham)、甜菜宁-乙酯(phenmedipham-ethyl)、氨氯吡啶酸(picloram)、氟吡酰草胺(picolinafen)、唑啉草酯(pinoxaden)、哌草磷(piperophos)、pirifenop、pirifenop-butyl、丙草胺(pretilachlor)、氟嘧磺隆(primisulfuron)、氟嘧磺隆(primisulfuron-methyl)、烯丙苯噻唑(probenazole)、氟唑草胺(profluazole)、环丙氰津(procyazine)、氨氟乐灵(prodiamine)、环丙氟灵(prifluralin)、环苯草酮(profoxydim)、调环酸(prohexadione)、调环酸(prohexadione-calcium)、茉莉酮(prohydroj asmone)、扑灭通(prometon)、扑草净(prometryn)、毒草胺(propachlor)、敌稗(propanil)、恶草酸(propaquizafop)、扑灭津(propazine)、苯胺灵(propham)、异丙草胺(propisochlor)、丙苯磺隆(propoxycarbazone)、丙苯磺隆(propoxycarbazone-sodium)、嗪咪唑嘧磺隆(propyrisulfuron)、炔苯酰草胺(propyzamide)、磺亚胺草(prosulfalin)、苄草丹(prosulfocarb)、氟磺隆(prosulfuron)、丙炔草胺(prynachlor)、双唑草腈(pyraclonil)、吡草醚(pyraflufen)、吡草醚(pyraflufen-ethyl)、pyrasulfotole、吡唑特(pyrazolynate(pyrazolate))、吡嘧磺隆(pyrazosulfuron)、吡嘧磺隆乙酯(pyrazosulfuron-ethyl)、苄草唑(pyrazoxyfen)、异丙酯草醚(pyribambenz)、异丙酯草醚(pyribambenz-isopropyl)、丙酯草醚(pyribambenz-propyl)、嘧啶肟草醚(pyribenzoxim)、稗草丹(pyributicarb)、达草止(pyridafol)、哒草特(pyridate)、环酯草醚(pyriftalid)、嘧草醚(pyriminobac)、嘧草醚(pyriminobac-methyl)、pyrimisulfan、嘧草硫醚(pyrithiobac)、嘧草硫醚(pyrithiobac-sodium)、异恶草酮(pyroxasulfone)、甲氧磺草胺(pyroxsulam)、二氯喹啉酸(quinchlorac)、氯甲喹啉酸(quinmerac)、灭藻醌(quinoclamine)、喹禾灵(quizalofop)、喹禾灵乙酯(quizalofop-ethyl)、精喹禾灵(quizalofop-P)、精喹禾灵乙酯(quizalofop-P-ethyl)、喹禾糠酯(quizalofop-P-tefuryl)、砜嘧磺隆(rimsulfuron)、苯嘧磺草胺(saflufenacil)、仲丁通(secbumeton)、烯禾啶(sethoxydim)、环草隆(siduron)、西玛津(simazine)、西草净(simetryn)、SN-106279即(2R)2({7-[2-氯-4-(三氟甲基)苯氧基]-2-萘基}氧基)丙酸甲酯、磺草酮(sulcotrione)、草克死(sulfallate(CDEC))、甲磺草胺(sulfentrazone)、甲嘧磺隆(sulfometuron)、甲嘧磺隆(sulfometuron-methyl)、草硫膦(sulfosate(glyphosate-trimesium))、磺酰磺隆(sulfosulfuron)、SYN-523、SYP-249即1-乙氧基-3-甲基-1-氧代丁-3-烯-2-基-5-[2-氯-4-(三氟甲基)苯氧基]-2-硝基苯甲酸酯、SYP-300即1-[7-氟-3-氧代-4-(丙-2-炔-1-基)3,4-二氢-2H-1,4-苯并噁嗪-6-基]-3-丙基-2-硫酮咪唑烷-4,5-二酮、牧草胺(tebutam)、丁噻隆(tebuthiuron)、四氯硝基苯(tecnazene)、tefuryltrione、环磺酮(tembotrione)、吡喃草酮(tepraloxydim)、特草定(terbacil)、特草灵(terbucarb)、特丁草胺(terbuchlor)、特丁通(terbumeton)、特丁津(terbuthylazine)、特丁净(terbutryn)、噻吩草胺(thenylchlor)、氟噻草胺(thiafluamide)、噻氟隆(thiazafluron)、噻唑烟酸(thiazopyr)、噻二唑草胺(thidiazimin)、噻苯隆(thidiazuron)、异草唑酮(thiencarbazone)、噻酮磺隆(thiencarbazone-methyl)、噻吩磺隆(thifensulfuron)、噻吩磺隆(thifensulfuron-methyl)、禾草丹(thiobencarb)、仲草丹(tiocarbazil)、苯吡唑草酮(topramezone)、三甲苯草酮(tralkoxydim)、triafamon野燕畏(triallate)、醚苯磺隆(triasulfuron)、三嗪氟草胺(triaziflam)、triazofenamide、苯磺隆(tribenuron)、苯磺隆(tribenuron-methyl)、三氯乙酸(trichloroaceticacid(TCA)),三氯吡氧乙酸(triclopyr)、灭草环(tridiphane)、草达津(trietazine)、三氟啶磺隆(trifloxysulfuron)、三氟啶磺隆(trifloxysulfuron-sodium)、氟乐灵(trifluralin)、氟胺磺隆(triflusulfuron)、氟胺磺隆(triflusulfuron-methyl)、三甲隆(trimeturon)、抗倒酯(trinexapac)、抗倒酯(trinexapac-ethyl)、三氟甲磺隆(tritosulfuron)、tsitodef、烯效唑(uniconazole)、精烯效唑(uniconazole-P)、灭草敌(vernolate)、ZJ-0166即3,4-二氯-N-{2-[(4,6-二甲氧基嘧啶-2-基)氧基]苄基}苯胺和如下化合物:
为进行施用,如果合适,将以市售形式存在的制剂以常规方式用水稀释,例如在可湿性粉剂、悬乳浓缩剂、分散剂和水分散性颗粒剂的情况下。粉剂、适于土壤施用的颗粒剂或适于撒播的颗粒剂和可喷洒溶液剂形式的制剂通常在施用前不用其他惰性物质稀释。式(I)的化合物的所需施用率根据外界条件——例如特别是温度、湿度和所用除草剂的类型——而变化。所述施用率可以在很宽的范围内变化,例如在0.001至1.0kg/ha以上的活性物质之间变化;然而,优选0.005-750g/ha。
以下实施例用于说明本发明:
A.化学实施例
1.2-氯-4-(甲基磺酰基)N-(1-(2-甲氧基乙基)四唑-5-基)苯甲酰胺的合成,(表中实施例编号1-12)
将在2ml吡啶中的176mg(0.75mmol)2-氯-4-(甲基磺酰基)苯甲酰氯、145mg(1.0mmol)5-氨基-1-(2-甲氧基乙基)四唑在60℃下搅拌12小时。然后加入0.1ml水,将混合物在60℃下搅拌30分钟并加入EA和2N HCl。分离出有机相并用2N HCl和盐水洗涤、经Na2SO4干燥,浓缩和通过RP-HPLC(乙腈/水)纯化。收率为66mg(23%)。
5-氨基-1-(2-甲氧基乙基)四唑的合成
将在10ml乙醇中的2.33g(10mmol)S-甲基异硫氨基脲氢碘盐和751mg(10mmol)2-甲氧基乙胺的混合物在回流下加热,直至无甲硫醇释放。然后,将混合物充分浓缩,并在搅拌下依次加入10ml水、0.3ml浓硝酸和1.7g(10mmol)溶于2ml水的硝酸银。搅拌10min后,加入0.5ml浓盐酸,通过抽滤滤出沉淀并用3ml水洗涤,并将1.5ml浓盐酸加入滤液中。在<5℃下,随后将溶于2ml水的0.7g(10mmol)硝酸钠加入至混合物中,并用20%浓度的含水氢氧化钠溶液将pH调至10。将混合物加热至60℃,保持30分钟,并在冷却后,用乙酸乙酯萃取。将有机相用饱和氯化钠溶液洗涤3次,干燥并浓缩,并将残余物溶解在少量乙酸乙酯中,再过滤。浅褐色晶体,收率为590mg(40%)。NMR(DMSO-d6):6.62(brs,2H),4.26(t,2H),3.65(t,2H),3.23(s,3H)
表1:式(I)的本发明化合物,其中A代表CY,B代表N且R代表2-甲氧基乙基
表2:式(I)的本发明化合物,其中A代表CY
表3:式(I)的本发明化合物,其中A代表N
B.制剂实施例
a)通过如下方法获得粉剂:将10重量份式(I)的化合物和/或其盐与90重量份作为惰性物质的滑石混合,并将混合物在锤磨机中粉碎。
b)通过如下方法获得易分散于水中的可湿性粉剂:将25重量份式(I)的化合物和/或其盐、64重量份作为惰性物质的含高岭土的石英、10重量份的木素磺酸钾和1重量份的作为润湿剂和分散剂的油酰基甲基牛磺酸钠混合,将混合物在销盘式研磨机(pinned-disk mill)中研磨。
c)通过如下方法获得易分散于水中的分散浓缩剂:将20重量份式(I)的化合物和/或其盐与6重量份的烷基苯酚聚乙二醇醚()、3重量份的异十三烷醇聚乙二醇醚(8EO)和71重量份石蜡矿物油(沸点范围为例如约255℃至高于277℃)混合,并将混合物在球磨机中研磨至低于5微米的细度。
d)通过如下方法获得悬乳浓缩剂:将15重量份式(I)的化合物和/或其盐、75重量份作为溶剂的环己酮和10重量份作为乳化剂的乙氧基化壬基苯酚混合。
e)通过如下方法得到水分散性颗粒剂:
将如下物质混合
75重量份式(I)的化合物和/或其盐、
10重量份的木素磺酸钙、
5重量份的十二烷基硫酸钠、
3重量份的聚乙烯醇和
7重量份的高岭土,
将混合物在销盘式研磨机中研磨,并在流化床中通过在其上喷洒作为制粒液体的水而粒化该粉末。
f)通过如下方法获得水分散性颗粒剂:
将下述物质在胶体磨机中均匀化并预粉碎
25重量份式(I)的化合物和/或其盐、
5重量份的2,2’-二萘基甲烷-6,6’-二磺酸钠、
2重量份的油酰基甲基牛磺酸钠、
1重量份的聚乙烯醇、
17重量份的碳酸钙和
50重量份的水,
随后在球磨机中研磨该混合物,并将所得悬浮液在喷雾塔中通过单料喷嘴雾化并干燥。
C.生物学实施例
1.抵抗有害植物的芽前除草作用
将单子叶或双子叶杂草植物或作物植物的种子种植于盛有沙质壤土的木质纤维盆中,并用土壤覆盖。然后,将以可湿性粉剂(WP)或乳液浓缩剂(EC)形式配置制剂的本发明的化合物以水悬浮液或乳液——水施用率为600至800l/ha(经换算)且添加0.2%的润湿剂——施用至覆盖土壤表面。处理后,将盆置于温室中并保持在适于所测试的植物良好生长的条件下。在3周测试期后,通过与未处理的对照组比较,目测评估对测试植物的损害程度(以百分比计的除草活性(%):100%活性=植物已死亡、0%活性=与对照植物相似)。此时,例如,在320g/ha的施用率下,编号为1-16、1-44、1-60、1-125、1-154、1-162、1-163、1-174、1-187、1-191、1-197、1-200、1-204、1-215、1-245、1-246、1-248、1-343、1-345、1-361、1-366、1-368、1-417、1-450、1-452、1-453、1-456、1-458、1-460、1-463、1-464、1-465、1-468、1-475、1-476、1-488、1-494、1-517、1-572、1-583、2-2、2-4、2-5、2-6、2-7、2-19、3-2和3-16的化合物各自对苘麻(Abutilon theophrasti)、反枝苋(Amaranthus retroflexus)、淡甘菊(Matricara inodora)、繁缕(Stellaria media)、阿拉伯婆婆纳(Veronica persica)和三色堇(Violatricolor)表现出至少90%的活性。
2.抵抗有害植物的芽后除草作用
将单子叶和双子叶杂草和作物植物的种子置于盛有沙质壤土的木质纤维盆中,用土壤覆盖,并置于温室中在良好生长条件下栽培。在播种2-3周后,对一叶期时的测试植物进行处理。然后,将以可湿性粉剂(WP)或乳液浓缩剂(EC)形式配置制剂的本发明的化合物以水悬浮液或乳液——水施用率为600至800l/ha(经换算)且添加0.2%的润湿剂——施用至植物的绿色部位。测试植物在温室中于最佳生长条件下放置约3周后,与未处理的对照组比较,目测评估制剂的活性(以百分比计的除草活性(%):100%活性=植物已死亡、0%活性=与对照植物相似)。此时,例如,在80g/ha的施用率下,编号为1-23、1-44、1-125、1-128、1-154、1-157、1-162、1-188、1-197、1-200、1-215、1-220、1-245、1-246、1-344、1-345、1-350、1-366、1-368、1-417、1-450、1-453、1-456、1-460、1-465、1-468、1-475、1-487、1-488、1-494、1-517、1-518、1-583、2-2、2-4、2-5、2-6、2-19、3-2、3-5和3-23的化合物各自对苘麻、淡甘菊、圆叶牵牛、繁缕、阿拉伯婆婆纳和三色堇表现出至少90%的活性。
Claims (13)
1.式(I)的N-(四唑-5-基)芳基甲酰胺或N-(三唑-5-基)芳基甲酰胺或其盐
其中
A代表N或CY,
B代表N或CH,
X代表硝基、卤素、氰基、甲酰基、氰硫基、(C1-C6)烷基、卤代-(C1-C6)烷基、(C2-C6)烯基、卤代-(C2-C6)烯基、(C2-C6)炔基、卤代-(C3-C6)炔基、(C3-C6)环烷基、卤代-(C3-C6)环烷基、(C3-C6)环烷基-(C1-C6)烷基、卤代-(C3-C6)环烷基-(C1-C6)烷基、COR1、COOR1、OCOOR1、NR1COOR1、C(O)N(R1)2、NR1C(O)N(R1)2、OC(O)N(R1)2、C(O)NR1OR1、OR1、OCOR1、OSO2R2、S(O)nR2、SO2OR1、SO2N(R1)2、NR1SO2R2、NR1COR1、(C1-C6)烷基-S(O)nR2、(C1-C6)烷基-OR1、(C1-C6)烷基-OCOR1、(C1-C6)烷基-OSO2R2、(C1-C6)烷基-CO2R1、(C1-C6)烷基-SO2OR1、(C1-C6)烷基-CON(R1)2、(C1-C6)烷基-SO2N(R1)2、(C1-C6)烷基-NR1COR1、(C1-C6)烷基-NR1SO2R2、NR1R2、P(O)(OR5)2、CH2P(O)(OR5)2、(C1-C6)烷基-杂芳基、(C1-C6)烷基-杂环基,其中最后2个提及的基团各自被s个选自卤素、(C1-C6)烷基、卤代-(C1-C6)烷基、S(O)n-(C1-C6)烷基、(C1-C6)烷氧基、卤代-(C1-C6)烷氧基的基团取代,且其中杂环基带有n个氧代基团,
Y代表氢、硝基、卤素、氰基、氰硫基、(C1-C6)烷基、卤代-(C1-C6)烷基、(C2-C6)烯基、卤代-(C2-C6)烯基、(C2-C6)炔基、卤代-(C2-C6)炔基、(C3-C6)环烷基、(C3-C6)环烯基、卤代-(C3-C6)环烷基、(C3-C6)环烷基-(C1-C6)烷基、卤代-(C3-C6)环烷基-(C1-C6)烷基、COR1、COOR1、OCOOR1、NR1COOR1、C(O)N(R1)2、NR1C(O)N(R1)2、OC(O)N(R1)2、CO(NOR1)R1、NR1SO2R2、NR1COR1、OR1、OSO2R2、S(O)nR2、SO2OR1、SO2N(R1)2(C1-C6)烷基-S(O)nR2、(C1-C6)烷基-OR1、(C1-C6)烷基-OCOR1、(C1-C6)烷基-OSO2R2、(C1-C6)烷基-CO2R1、(C1-C6)烷基-CN、(C1-C6)烷基-SO2OR1、(C1-C6)烷基-CON(R1)2、(C1-C6)烷基-SO2N(R1)2、(C1-C6)烷基-NR1COR1、(C1-C6)烷基-NR1SO2R2、N(R1)2、P(O)(OR5)2、CH2P(O)(OR5)2、(C1-C6)烷基-苯基、(C1-C6)烷基-杂芳基、(C1-C6)烷基-杂环基、苯基、杂芳基或杂环基,其中最后提及的6个基团各自被s个选自卤素、硝基、氰基、(C1-C6)烷基、卤代-(C1-C6)烷基、(C3-C6)环烷基、S(O)n-(C1-C6)烷基、(C1-C6)烷氧基、卤代-(C1-C6)烷氧基、(C1-C6)烷氧基-(C1-C4)烷基和氰甲基的基团取代,且其中杂环基带有n个氧代基团,
Z代表卤素、氰基、氰硫基、卤代-(C1-C6)烷基、(C2-C6)烯基、卤代-(C2-C6)烯基、(C2-C6)炔基、卤代-(C2-C6)炔基、(C3-C6)环烷基、卤代-(C3-C6)环烷基、(C3-C6)环烷基-(C1-C6)烷基、卤代-(C3-C6)环烷基-(C1-C6)烷基、COR1、COOR1、OCOOR1、NR1COOR1、C(O)N(R1)2、NR1C(O)N(R1)2、OC(O)N(R1)2、C(O)NR1OR1、OSO2R2、S(O)nR2、SO2OR1、SO2N(R1)2、NR1SO2R2、NR1COR1、(C1-C6)烷基-S(O)nR2、(C1-C6)烷基-OR1、(C1-C6)烷基-OCOR1、(C1-C6)烷基-OSO2R2、(C1-C6)烷基-CO2R1、(C1-C6)烷基-SO2OR1、(C1-C6)烷基-CON(R1)2、(C1-C6)烷基-SO2N(R1)2、(C1-C6)烷基-NR1COR1、(C1-C6)烷基-NR1SO2R2、N(R1)2、P(O)(OR5)2、杂芳基、杂环基或苯基,其中最后提及的3个基团各自被s个选自卤素、硝基、氰基、(C1-C6)烷基、卤代-(C1-C6)烷基、(C3-C6)环烷基、S(O)n-(C1-C6)烷基、(C1-C6)烷氧基和卤代-(C1-C6)烷氧基的基团取代,且其中杂环基带有n个氧代基团,或
Z在Y代表基团S(O)nR2时,,其还可代表氢、(C1-C6)烷基或(C1-C6)烷氧基,
R代表CH2R6,
被m个氧代基团取代的CH2-杂环基,
被t个(C1-C6)烷基取代的(C3-C7)环烷基,
(C2-C6)烷基、(C3-C7)环烷基、卤代-(C2-C6)烷基、(C2-C6)烯基、卤代-(C2-C6)烯基、(C2-C6)炔基或卤代-(C2-C6)炔基,所述基团各自被u个选自硝基、氰基、羟基、氧代、SiR5 3、PO(OR5)2、S(O)n-(C1-C6)烷基、(C1-C6)烷氧基、卤代-(C1-C6)烷氧基、N(R3)2、COR3、OCOR3、NR3COR3、NR3SO2R4、(C3-C6)环烷基、杂芳基、杂环基、苯基、Q-杂芳基、Q-杂环基、Q-苯基和Q-苄基的基团取代,其中所述基团(C3-C6)环烷基、杂芳基、杂环基、苯基、Q-杂芳基、Q-杂环基、Q-苯基和Q-苄基各自被s个选自甲基、乙基、甲氧基、氰基、硝基、三氟甲基和卤素的基团取代,且其中杂环基和环烷基带有n个氧代基团,
Q代表O、S或NR3,
R1代表氢、(C1-C6)烷基、(C1-C6)卤代烷基、(C2-C6)烯基、(C2-C6)卤代烯基、(C2-C6)炔基、(C2-C6)卤代炔基、(C3-C6)环烷基、(C3-C6)环烯基、(C3-C6)卤代环烷基、(C1-C6)烷基-O-(C1-C6)烷基、(C3-C6)环烷基-(C1-C6)烷基、苯基、苯基-(C1-C6)烷基、杂芳基、(C1-C6)烷基-杂芳基、杂环基、(C1-C6)烷基-杂环基、(C1-C6)烷基-O-杂芳基、(C1-C6)烷基-O-杂环基、(C1-C6)烷基-NR3-杂芳基、(C1-C6)烷基-NR3-杂环基,其中最后提及的21个基团被s个选自氰基、卤素、硝基、氰硫基、OR3、S(O)nR4、N(R3)2、NR3OR3、COR3、OCOR3、SCOR4、NR3COR3、NR3SO2R4、CO2R3、COSR4、CON(R3)2和(C1-C4)烷氧基-(C2-C6)烷氧基羰基的基团取代,且其中杂环基带有n个氧代基团,
R2代表(C1-C6)烷基、(C1-C6)卤代烷基、(C2-C6)烯基、(C2-C6)卤代烯基、(C2-C6)炔基、(C2-C6)卤代炔基、(C3-C6)环烷基、(C3-C6)环烯基、(C3-C6)卤代环烷基、(C1-C6)烷基-O-(C1-C6)烷基、(C3-C6)环烷基-(C1-C6)烷基、苯基、苯基-(C1-C6)烷基、杂芳基、(C1-C6)烷基-杂芳基、杂环基、(C1-C6)烷基-杂环基、(C1-C6)烷基-O-杂芳基、(C1-C6)烷基-O-杂环基、(C1-C6)烷基-NR3-杂芳基、(C1-C6)烷基-NR3-杂环基,其中最后提及的21个基团被s个选自氰基、卤素、硝基、氰硫基、OR3、S(O)nR4、N(R3)2、NR3OR3、COR3、OCOR3、SCOR4、NR3COR3、NR3SO2R4、CO2R3、COSR4、CON(R3)2和(C1-C4)烷氧基-(C2-C6)烷氧基羰基的基团取代,且其中杂环基带有n个氧代基团,
R3代表氢、(C1-C6)烷基、(C2-C6)烯基、(C2-C6)炔基、(C3-C6)环烷基或(C3-C6)环烷基-(C1-C6)烷基,
R4代表(C1-C6)烷基、(C2-C6)烯基或(C2-C6)炔基、(C3-C6)环烷基或(C3-C6)环烷基-(C1-C6)烷基,
R5代表(C1-C4)烷基,
R6代表OCOOR4、NR4COOR4、S(O)n-(C1-C6)烷基、S(O)n-(C1-C6)卤代烷基、硝基、氰基、SiR5 3、PO(OR5)2、杂环基或环烷基,其中最后提及的2个基团带有m个氧代基团或羟基,
m代表1或2,
n代表0、1或2,
s代表0、1、2或3,
t代表1、2、3或4,
u代表1、2、3、4或5。
2.如权利要求1所述的N-(四唑-5-基)芳基甲酰胺或N-(三唑-5-基)芳基甲酰胺,其中
A代表N或CY,
B代表N或CH,
X代表硝基、卤素、氰基、氰硫基、(C1-C6)烷基、卤代-(C1-C6)烷基、(C2-C6)烯基、卤代-(C2-C6)烯基、(C2-C6)炔基、卤代-(C3-C6)炔基、(C3-C6)环烷基、卤代-(C3-C6)环烷基、C1-C6)烷基-O-(C1-C6)烷基、(C3-C6)环烷基-(C1-C6)烷基、卤代-(C3-C6)环烷基-(C1-C6)烷基、COR1、OR1、OCOR1、OSO2R2、S(O)nR2、SO2OR1、SO2N(R1)2、NR1SO2R2、NR1COR1、(C1-C6)烷基-S(O)nR2、(C1-C6)烷基-OR1、(C1-C6)烷基-OCOR1、(C1-C6)烷基-OSO2R2、(C1-C6)烷基-CO2R1、(C1-C6)烷基-SO2OR1、(C1-C6)烷基-CON(R1)2、(C1-C6)烷基-SO2N(R1)2、(C1-C6)烷基-NR1COR1或(C1-C6)烷基-NR1SO2R2、(C1-C6)烷基-杂芳基、(C1-C6)烷基-杂环基,其中最后提及的2个基团各自被s个选自卤素、(C1-C6)烷基、卤代-(C1-C6)烷基、S(O)n-(C1-C6)烷基、(C1-C6)烷氧基、卤代-(C1-C6)烷氧基的基团取代,且其中杂环基带有n个氧代基团,
Y代表氢、硝基、卤素、氰基、氰硫基、(C1-C6)烷基、卤代-(C1-C6)烷基、(C2-C6)烯基、卤代-(C2-C6)烯基、(C2-C6)炔基、卤代-(C3-C6)炔基、(C3-C6)环烷基、(C3-C6)环烯基、卤代-(C3-C6)环烷基、(C3-C6)环烷基-(C1-C6)烷基、卤代-(C3-C6)环烷基-(C1-C6)烷基、COR1、OR1、COOR1、OSO2R2、S(O)nR2、SO2OR1、SO2N(R1)2、N(R1)2、NR1SO2R2、NR1COR1、(C1-C6)烷基-S(O)nR2、(C1-C6)烷基-OR1、(C1-C6)烷基-OCOR1、(C1-C6)烷基-OSO2R2、(C1-C6)烷基-CO2R1、(C1-C6)烷基-SO2OR1、(C1-C6)烷基-CON(R1)2、(C1-C6)烷基-SO2N(R1)2、(C1-C6)烷基-NR1COR1、(C1-C6)烷基-NR1SO2R2、(C1-C6)烷基-苯基、(C1-C6)烷基-杂芳基、(C1-C6)烷基-杂环基、苯基、杂芳基或杂环基,其中最后提及的6个基团各自被s个选自卤素、硝基、氰基、(C1-C6)烷基、卤代-(C1-C6)烷基、(C3-C6)环烷基、S(O)n-(C1-C6)烷基、(C1-C6)烷氧基、卤代-(C1-C6)烷氧基、(C1-C6)烷氧基-(C1-C4)烷基和氰甲基的基团取代,且其中杂环基代有n个氧代基团,
Z代表卤素、氰基、氰硫基、卤代-(C1-C6)烷基、(C2-C6)烯基、卤代-(C2-C6)烯基、(C2-C6)炔基、卤代-(C3-C6)炔基、(C3-C6)环烷基、卤代-(C3-C6)环烷基、(C3-C6)环烷基-(C1-C6)烷基、卤代-(C3-C6)环烷基-(C1-C6)烷基、COR1、COOR1、C(O)N(R1)2、C(O)NR1OR1、OSO2R2、S(O)nR2、SO2OR1、SO2N(R1)2、NR1SO2R2、NR1COR1、(C1-C6)烷基-S(O)nR2、(C1-C6)烷基-OR1、(C1-C6)烷基-OCOR1、(C1-C6)烷基-OSO2R2、(C1-C6)烷基-CO2R1、(C1-C6)烷基-SO2OR1、(C1-C6)烷基-CON(R1)2、(C1-C6)烷基-SO2N(R1)2、(C1-C6)烷基-NR1COR1、(C1-C6)烷基-NR1SO2R2、1,2,4-三唑-1-基,或
Z在Y代表基团S(O)nR2时,其还可代表氢、(C1-C6)烷基或(C1-C6)烷氧基,
R代表CH2R6,
被m个氧代基团取代的CH2-杂环基,
(C2-C6)烷基、(C3-C7)环烷基、卤代-(C2-C6)烷基、(C2-C6)烯基、卤代-(C2-C6)烯基、(C2-C6)炔基或卤代-(C2-C6)炔基,所述基团各自被u个选自硝基、氰基、羟基、氧代、SiR5 3、PO(OR5)2、S(O)n-(C1-C6)烷基、(C1-C6)烷氧基、卤代-(C1-C6)烷氧基、N(R3)2、COR3、OCOR3、NR3COR3、NR3SO2R4、(C3-C6)环烷基、杂芳基、杂环基、苯基、Q-杂芳基、Q-杂环基、Q-苯基和Q-苄基的基团取代,其中所述基团(C3-C6)环烷基、杂芳基、杂环基、苯基、Q-杂芳基、Q-杂环基、Q-苯基和Q-苄基各自被s个选自甲基、乙基、甲氧基、氰基、硝基、三氟甲基和卤素的基团取代,且其中杂环基和环烷基带有n个氧代基团,
Q代表O、S或NR3,
R1代表氢、(C1-C6)烷基、(C2-C6)烯基、(C2-C6)炔基、(C3-C6)环烷基、(C3-C6)环烷基-(C1-C6)烷基、(C1-C6)烷基-O-(C1-C6)烷基、苯基、苯基-(C1-C6)烷基、杂芳基、(C1-C6)烷基-杂芳基、杂环基、(C1-C6)烷基-杂环基、(C1-C6)烷基-O-杂芳基、(C1-C6)烷基-O-杂环基、(C1-C6)烷基-NR3-杂芳基或(C1-C6)烷基-NR3-杂环基,其中最后提及的16个基团被s个选自氰基、卤素、硝基、OR3、S(O)nR4、N(R3)2、NR3OR3、COR3、OCOR3、NR3COR3、NR3SO2R4、CO2R3、CON(R3)2和(C1-C4)烷氧基-(C2-C6)烷氧基羰基的基团取代,且其中杂环基带有n个氧代基团,
R2代表(C1-C6)烷基、(C2-C6)烯基、(C2-C6)炔基、(C3-C6)环烷基、(C3-C6)环烷基-(C1-C6)烷基、(C1-C6)烷基-O-(C1-C6)烷基、苯基、苯基-(C1-C6)烷基、杂芳基、(C1-C6)烷基-杂芳基、杂环基、(C1-C6)烷基-杂环基、(C1-C6)烷基-O-杂芳基、(C1-C6)烷基-O-杂环基、(C1-C6)烷基-NR3-杂芳基或(C1-C6)烷基-NR3-杂环基,其中这些基团被s个选自氰基、卤素、硝基、OR3、S(O)nR4、N(R3)2、NR3OR3、NR3SO2R4、COR3、OCOR3、NR3COR3、CO2R3、CON(R3)2和(C1-C4)烷氧基-(C2-C6)烷氧基羰基的基团取代,且其中杂环基带有n个氧代基团,
R3代表氢、(C1-C6)烷基、(C2-C6)烯基、(C2-C6)炔基、(C3-C6)环烷基或(C3-C6)环烷基-(C1-C6)烷基,
R4代表(C1-C6)烷基、(C2-C6)烯基或(C2-C6)炔基,
R5代表甲基或乙基,
R6代表OCOOR4、NR4COOR4、S(O)n-(C1-C6)烷基、S(O)n-(C1-C6)卤代烷基、硝基、氰基、SiR5 3、PO(OR5)2或带有m个氧代基团的杂环基,
m代表1或2,
n代表0、1或2,
s代表0、1、2或3,
u代表1、2、3、4或5。
3.如权利要求1或2所述的N-(四唑-5-基)芳基甲酰胺或N-(三唑-5-基)芳基甲酰胺,其中
A代表N或CY,
B代表N或CH,
X代表硝基、卤素、氰基、(C1-C6)烷基、卤代-(C1-C6)烷基、(C3-C6)环烷基、OR1、S(O)nR2、(C1-C6)烷基-S(O)nR2、(C1-C6)烷基-OR1、(C1-C6)烷基-CON(R1)2、(C1-C6)烷基-SO2N(R1)2、(C1-C6)烷基-NR1COR1、(C1-C6)烷基-NR1SO2R2、(C1-C6)烷基-杂芳基、(C1-C6)烷基-杂环基,其中最后提及的2个基团各自被s个选自卤素、(C1-C6)烷基、卤代-(C1-C6)烷基、S(O)n-(C1-C6)烷基、(C1-C6)烷氧基、卤代-(C1-C6)烷氧基的基团取代,且其中杂环基带有n个氧代基团,
Y代表氢、硝基、卤素、氰基、(C1-C6)烷基、(C1-C6)卤代烷基、OR1、S(O)nR2、SO2N(R1)2、N(R1)2、NR1SO2R2、NR1COR1、(C1-C6)烷基-S(O)nR2、(C1-C6)烷基-OR1、(C1-C6)烷基-CON(R1)2、(C1-C6)烷基-SO2N(R1)2、(C1-C6)烷基-NR1COR1、(C1-C6)烷基-NR1SO2R2、(C1-C6)烷基-苯基、(C1-C6)烷基-杂芳基、(C1-C6)烷基-杂环基、苯基、杂芳基或杂环基,其中最后提及的6个基团各自被s个选自卤素、硝基、氰基、(C1-C6)烷基、卤代-(C1-C6)烷基、(C3-C6)环烷基、S(O)n-(C1-C6)烷基、(C1-C6)烷氧基、卤代-(C1-C6)烷氧基、(C1-C6)烷氧基-(C1-C4)烷基和氰甲基的基团取代,且其中杂环基带有n个氧代基团,
Z代表卤素、氰基、卤代-(C1-C6)烷基、(C3-C6)环烷基、S(O)nR2、1,2,4-三唑-1-基,或者,在Y代表基团S(O)nR2时,Z还可代表氢、甲基、甲氧基或乙氧基,
R代表CH2R6,
CH2-杂环基,其中杂环基带有m个氧代基团,
(C2-C6)烷基、(C3-C7)环烷基、卤代-(C2-C6)烷基、(C2-C6)烯基、卤代-(C2-C6)烯基、(C2-C6)炔基或卤代-(C2-C6)炔基,所述基团各自被u个选自硝基、氰基、羟基、氧代、SiR5 3、PO(OR5)2、S(O)n-(C1-C6)烷基、(C1-C6)烷氧基、卤代-(C1-C6)烷氧基、N(R3)2、COR3、OCOR3、NR3COR3、NR3SO2R4、(C3-C6)环烷基、杂芳基、杂环基、苯基、Q-杂芳基、Q-杂环基、Q-苯基和Q-苄基的基团取代,其中所述基团(C3-C6)环烷基、杂芳基、杂环基、苯基、Q-杂芳基、Q-杂环基、Q-苯基和Q-苄基各自被s个选自甲基、乙基、甲氧基、氰基、硝基、三氟甲基和卤素的基团取代,且其中杂环基和环烷基带有n个氧代基团,
Q代表O、S或NR3,
R1代表氢、(C1-C6)烷基、(C2-C6)烯基、(C2-C6)炔基、(C3-C6)环烷基、(C3-C6)环烷基-(C1-C6)烷基、(C1-C6)烷基-O-(C1-C6)烷基、苯基、苯基-(C1-C6)烷基、杂芳基、(C1-C6)烷基-杂芳基、杂环基、(C1-C6)烷基-杂环基、(C1-C6)烷基-O-杂芳基、(C1-C6)烷基-O-杂环基、(C1-C6)烷基-NR3-杂芳基或(C1-C6)烷基-NR3-杂环基,其中最后提及的16个基团各自被s个选自氰基、卤素、硝基、OR3、S(O)nR4、N(R3)2、NR3OR3、COR3、OCOR3、NR3COR3、NR3SO2R4、CO2R3、CON(R3)2和(C1-C4)烷氧基-(C2-C6)烷氧基羰基的基团取代,且其中杂环基带有n个氧代基团,
R2代表(C1-C6)烷基、(C3-C6)环烷基或(C3-C6)环烷基-(C1-C6)烷基,其中以上提及的3个取代基被s个选自卤素和OR3的基团取代,
R3代表氢或(C1-C6)烷基,
R4代表(C1-C6)烷基,
R5代表甲基或乙基,
R6代表OCOOR4、NR4COOR4、S(O)n-(C1-C6)烷基、S(O)n-(C1-C6)卤代烷基、硝基、氰基、SiR5 3、PO(OR5)2,
m代表1或2,
n代表0、1或2,
s代表0、1、2或3,
u代表1、2、3、4或5。
4.一种除草组合物,其特征在于,所述组合物包含除草有效量的权利要求1-3任一项所述的至少一种式(I)化合物。
5.如权利要求4所述的除草组合物,其为与制剂助剂的混合物。
6.如权利要求4或5所述的除草组合物,包含至少一种选自杀昆虫剂、杀螨剂、除草剂、杀真菌剂、安全剂和生长调节剂的其他农药活性化合物。
7.如权利要求6所述的除草组合物,包含安全剂。
8.如权利要求7所述的除草组合物,包含环丙磺酰胺、解毒喹、吡唑解草酯或双苯恶唑酸。
9.如权利要求6-8任一项所述的除草组合物,包含其他除草剂。
10.一种用于防治不想要的植物的方法,其特征在于,包括:将有效量的权利要求1-3任一项所述的至少一种式(I)化合物或权利要求4至9任一项所述的除草组合物施用于不想要的植物的植株或位点。
11.如权利要求1-3任一项所述的式(I)化合物或权利要求4-9任一项所述的除草组合物用于防治不想要的植物的用途。
12.如权利要求11所述的用途,其特征在于,将所述式(I)化合物用于防治有用植物作物中的不想要的植物。
13.如权利要求12所述的用途,其特征在于,所述有用植物是转基因有用植物。
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WO2024074126A1 (zh) * | 2022-10-05 | 2024-04-11 | 江苏中旗科技股份有限公司 | 一种4-甲磺酰基苯甲酰胺类化合物、制备方法、除草组合物及用途 |
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AR087385A1 (es) | 2014-03-19 |
EP2739611A1 (de) | 2014-06-11 |
BR112014002191A2 (pt) | 2017-03-07 |
WO2013017559A1 (de) | 2013-02-07 |
JP6078065B2 (ja) | 2017-02-08 |
IN2014DN00176A (zh) | 2015-07-10 |
PL2739611T3 (pl) | 2015-09-30 |
EP2739611B1 (de) | 2015-05-13 |
US20140179527A1 (en) | 2014-06-26 |
BR112014002191B1 (pt) | 2018-07-17 |
CN103717581B (zh) | 2016-04-06 |
JP2014521676A (ja) | 2014-08-28 |
ES2542681T3 (es) | 2015-08-10 |
US8822378B2 (en) | 2014-09-02 |
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