CN1048851A - 取代的嘧啶氧基(硫基)丙烯酸衍生物和三嗪氧基(硫基)丙烯酸衍生物,其制备方法和其作为除草剂,杀菌剂和植物生长调节剂的应用 - Google Patents
取代的嘧啶氧基(硫基)丙烯酸衍生物和三嗪氧基(硫基)丙烯酸衍生物,其制备方法和其作为除草剂,杀菌剂和植物生长调节剂的应用 Download PDFInfo
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- CN1048851A CN1048851A CN90104761A CN90104761A CN1048851A CN 1048851 A CN1048851 A CN 1048851A CN 90104761 A CN90104761 A CN 90104761A CN 90104761 A CN90104761 A CN 90104761A CN 1048851 A CN1048851 A CN 1048851A
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- alkylamino
- alkyl
- phenyl
- alkoxyl group
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
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- 239000011575 calcium Substances 0.000 description 1
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- HCWYXKWQOMTBKY-UHFFFAOYSA-N calcium;dodecyl benzenesulfonate Chemical class [Ca].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 HCWYXKWQOMTBKY-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
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- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical class CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 1
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- 238000001035 drying Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
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- 239000011737 fluorine Substances 0.000 description 1
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- 150000005826 halohydrocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- JPKCKTNGNQKUFY-UHFFFAOYSA-N methyl 2-(4,6-dimethoxypyrimidin-2-yl)sulfanyl-3-phenylprop-2-enoate Chemical class C=1C=CC=CC=1C=C(C(=O)OC)SC1=NC(OC)=CC(OC)=N1 JPKCKTNGNQKUFY-UHFFFAOYSA-N 0.000 description 1
- BFBPISPWJZMWJN-UHFFFAOYSA-N methyl 2-[(7-hydroxy-3,7-dimethyloctylidene)amino]benzoate Chemical compound COC(=O)C1=CC=CC=C1N=CCC(C)CCCC(C)(C)O BFBPISPWJZMWJN-UHFFFAOYSA-N 0.000 description 1
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- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
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- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000007715 potassium iodide Nutrition 0.000 description 1
- 229960004839 potassium iodide Drugs 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
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- 235000017550 sodium carbonate Nutrition 0.000 description 1
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- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- UUCCCPNEFXQJEL-UHFFFAOYSA-L strontium dihydroxide Chemical compound [OH-].[OH-].[Sr+2] UUCCCPNEFXQJEL-UHFFFAOYSA-L 0.000 description 1
- 229910001866 strontium hydroxide Inorganic materials 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
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- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-N trans-cinnamic acid Chemical compound OC(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-N 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
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- 239000000341 volatile oil Substances 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
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Classifications
-
- 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
-
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
-
- 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
- A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
- A01N43/68—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms with two or three nitrogen atoms directly attached to ring carbon atoms
- A01N43/70—Diamino—1,3,5—triazines with only one oxygen, sulfur or halogen atom or only one cyano, thiocyano (—SCN), cyanato (—OCN) or azido (—N3) group directly attached to a ring carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur 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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- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
本发明涉及通式I所示的新的取代的嘧啶氧基
(硫基)丙烯酸衍生物和三嗪氧基(硫基)丙烯酸衍生物
(式中A、G、R1、R2、R3、X和Y具有说明书中所述意
义),涉及它们的制备方法和作为除草剂,杀菌剂和植
物生长调节剂的应用。
Description
本发明涉及新的取代的嘧啶氧基(硫基)丙烯酸衍生物和三嗪氧基(硫基)丙烯酸衍生物,其制备方法和其作为除草剂、杀菌剂和植物生长调节剂的应用。
已知嘧啶衍生物具有除草作用(参见EP-申请0223406 0249707,0249708,0287072,0287027)。但这些已知化合物的除草作用经常不足,或者在主要作物的相应除草作用上呈现出选择性问题。
本发明的任务是制备一些新的化合物,这些新化合物没有上述缺点,而且其生物学性能优于迄今已知的一些化合物。
已发现,通式Ⅰ所示的取代的嘧啶氧基(硫基)丙烯酸衍生物和三嗪氧基(硫基)丙烯酸衍生物以及它们的碱金属盐、碱土金属盐、有机铵盐和它们的E型同分异构体及Z型同分异构体显示出新颖的除草、杀真菌和植物生长调节作用,
式中:
A为通式A-1至A-6所示的基团之一;
C1-C10-烷基;被C1-C4烷氧基、C1-C4-烷硫基、氨基、C1-C4-烷氨基、二-C1-C4烷氨基、硝基、三氟甲基、卤素或苯基进行过一次或多次、相同基或不同基取代的C1-C10-烷基;C2-C10-烯基;被C1-C4烷氧基、C1-C4烷硫基、氨基、C1-C4烷氨基、二-C1-C4烷氨基、硝基、三氟甲基、卤素或苯基进行过一次或多次、相同基或不同基取代的C2-C10-烯基;C2-C10-炔基;被C1-C4-烷氧基、C1-C4-烷硫基、氨基、C1-C4-烷氨基、二-C1-C4-烷氨基、硝基、三氟甲基、卤素或苯基进行过一次或多次、相同基或不同基取代的C2-C10-炔基;C3-C8-环烷基;被C1-C4-烷基、C1-C4-烷氧基、C1-C4-环硫基、氨基、氨基、C1-C4-烷氨基、二-C1-C4-烷氨基、硝基、三氟甲基、卤素或苯基进行过一次或多次,相同基或不同基取代的C2--C8环烷基;C4-C8-环烯基;被C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷硫基、氨基、C1-C4-烷氨基、二-C1-C4-烷氨基、硝基、三氟甲基、卤素或苯基进行过一次或多次、相同基或不同基取代的C4-C8-环烯基,
D为氧原子、硫原子或-NR′-,
G为氢原子或C1-C6-烷基,
R1为氢原子、C1-C4-烷基或苄基,
R2为C1-C4烷基、C1-C4-烷氧基、C1-C4-烷硫基、C1-C4-烷氨基、二-C1-C4-烷氨基或卤素原子,
R3为C1-C4-烷基、C1-C4烷氧基、C1-C4烷硫基、C1-C4-烷氨基、二-C1-C4-烷氨基或卤素原子,
R4为氢原子、C1-C4-烷基、C1-C4烷氧基、氨基、二-C1-C4-烷氨基、硝基、卤素原子、三氟甲基或苯基,
R5为氢原子、C1-C4-烷基、C1-C4-烷氧基、氨基、二-C1-C4-烷氨基、硝基、卤素原子、三氟甲基或苯基,
R6为氢原子、C1-C4-烷基、C1-C4-烷氧基、氨基、二-C1-C4-烷氨基、硝基、卤素原子、三氟甲基或苯基,
R7为氢原子、C1-C4烷基、C1-C4-烷氧基、氨基、二-C1-C4-烷氨基、硝基、卤素原子、三氟甲基或苯基,
R8为氢原子、C1-C4-烷基、C1-C4烷氧基、氨基、二-C1-C4-烷氨基、硝基、卤素原子、三氟甲基或苯基,
R9为氢原子、C1-C4-烷基或苯基,
X为氧原子或硫原子
Y为次甲基或氮原子。
卤素包括氟、氯、溴和碘。碱金属指锂、钠和钾、碱土金属指钙、锶和钡。
通式Ⅰ所示的本发明的一些化合物可按例如以下的方法制备:
A)使通式Ⅱ所示的化合物在合适的溶剂中在有合适的碱存在下和通式Ⅲ所示的化合物进行反应,
式中R1、R2、R3、X和Y有通式Ⅰ中所述意义,
式中A和G有通式Ⅰ中所述意义;
或B)使通式Ⅳ所示的化合物在合适的极性溶剂中与碱金属碱、碱土金属或有机铵碱反应成通式Ⅴ所示的化合物,
式中A、G、R1、R2、R3、X和Y有通式Ⅰ中所述意义,
式中A、G、R2、R3、X和Y有通式Ⅰ中所述的意义,M代表碱金属原子、一当量碱土金属原子或有机铵基;
或C)使通式Ⅴ所示的化合物在合适的溶剂中与合适的酸反应成通式Ⅵ所示的化合物,
式中A、G、R2、R3、M、X和Y有通式Ⅴ中所述意义,
式中A、G、R2、R3、X和Y有通式Ⅰ中所述意义;
或D)使通式Ⅳ所示的化合物在合适的溶剂中与合适的酸反应成通式Ⅵ所示的化合物,
式中A、G、R2、R3、X和Y具有通式Ⅰ中所述意义,R1代表C1-C4烷基和苄基,
式中A、G、R2、R3、X和Y有通式Ⅰ所述意义。
以上各方法最好在有稀释剂存在下实施。为此,可使用对反应的呈惰性的溶剂。
合适的溶剂的例子有水、脂肪烃、脂环烃和芳香烃,这些烃可选择性地被氯化,例如己烷、环己烷、石油醚、挥发油、苯、甲苯、二甲苯、二氯甲烷、氯仿、四氯化碳、二氯乙烷和三氯乙烷;醚、例如二异丙醚、二丁醚、氧化丙烯、二噁烷和四氢呋喃;酮,例如丙酮、甲乙酮、甲基异丙基酮和甲基异丁基酮;腈,例如乙腈、丙腈;醇,例如甲醇、乙醇、异丙醇、丁醇和乙二醇;酯,例如醋酸乙酯、醋酸戊酯;酰胺,例如二甲基甲酰胺和二甲基乙酰胺;亚砜和砜,例如二甲基亚砜和环丁砜;碱,例如吡啶。
反应催化剂的存在是能有好处的。适于作催化剂的有碘化钾和鎓类化合物,如季铵化合物、鏻化合物和砷化合物以及锍化合物。同样也适合的有聚乙二醇醚,尤其是环状聚乙二醇醚,例如18-冠-6;叔胺,例如三丁基胺。特别好的化合物是季铵化合物,例如苄基三乙基氯化铵和四丁基氯化铵。
反应可在常压下进行,但若需要,也可在加压或减压下进行。
可用于方法A)的溶剂最好是非质子传递溶剂,例如苯、甲苯、二甲苯、四氢呋喃、乙醚、己烷、二甲基甲酰胺或二甲基亚砜。
可作为碱使用的例如有氢化钠、叔丁醇钾或二异丙酰胺锂。
反应温度在-78℃和各溶剂或混合溶剂的沸点之间。
反应时间为5分钟至48小时,最好是0.5至24小时。
通式Ⅱ所示的化合物在文献中得到了说明,或可按类似于文献介绍的方法予以制备(参见Khim.-Farm.Zh.16(8),931-4〔1982〕;Ukr.Khim.Zh.〔俄文版〕49(11),1205-8〔1983〕;Fizol.Akt.Veshchestva 18,75-9〔1986〕;UssR-PS791746)。
可用于方法B),C)和D)的溶剂最好是醇,例如甲醇、乙醇、丙醇或异丙醇;酮,例如丙酮或甲乙酮;二甲基甲酰胺或二甲基亚砜,水或溶剂/水混合物。
可作为碱金属碱、碱土金属碱或有机铵碱使用的,例如有碳酸盐,如碳酸钠、碳酸钾或碳酸钙;金属氢氧化物如氢氧化钠、氢氧化钾、氢氧化钡或氢氧化锶;而可作为有机铵碱的有氨、烷基胺(伯胺)、二烷基胺(仲胺)或三烷基胺(叔胺)。
可考虑的酸是例如盐酸或硫酸。
反应温度在室温和各个溶剂的沸点之间。反应时间为0.5至48小时。
如果在通式Ⅳ中的R1为苄基,则也可通过催化还原(氢化)得到通式Ⅵ所示的化合物。
按上述方法制得的本发明化合物可按通常方法,比如说通过在常压或减压下蒸去所使用的溶剂,通过用水沉淀或通过萃取使其从反应混合物中离析。
在一般情况下通过柱色谱法精制,以及通过分馏或结晶可以提高产品纯度。
本发明的这些化合物在通常情况下是无色和无气味的液体以及晶体。它们可溶于水,微溶于脂肪烃如石油醚、己烷、戊烷和环己烷,易溶于卤代烃如氯仿、二氯甲烷和四氯化碳;芳香烃如苯、甲苯和二甲苯;醚如乙醚、四氢呋喃和二噁烷;腈如乙腈;醇如甲醇和乙醇;酰胺如二甲基甲酰胺;亚砜如二甲基亚砜。
本发明的这些化合物在阔叶杂草和青草中显示出良好的除草作用。在不同的农作物中有选择地使用本发明的活性物质是可能的,例如使用于油菜籽、块根植物、黄豆、棉花、水稻、大麦、小麦和其它谷类。其中少数活性物质在块根植物、棉花、黄豆和谷物中作选择除草剂特别合适。同样可将这些化合物用在多年生经济作物例如林场、观赏木本植被、水果园、葡萄园、柑果园、核桃园、香蕉园、咖啡园、茶场、橡胶园、油椰子园、可可园、浆果园和啤酒花园中消灭杂草,并用在一年生的经济作物中有选择地消灭杂草。
可将本发明化合物用于防除例如以下的植物种属:
双子叶杂草属:芥属、独行菜属、猪殃殃属、繁缕属、洋甘菊属、春黄菊属、牛膝菊属、藜属、芸苔属、荨麻属、千里光属、苋属、马齿苋属、苍耳属、旋花属、番薯属、蓼属、田菁属、豚草属、蓟属、气廉属、苦苣菜属、茄属、蔊菜属、野芝麻属、婆婆纳属、苘麻属、曼陀罗属、堇菜属、鼬瓣花属、罂粟属、矢车菊属和菊属。
单子叶杂草属:燕麦属、看麦娘属、稗属、狗毛草属、黍属、马唐属、早熟禾属、蟋蟀草属、臂形草属、毒草属、雀麦属、莎草属、冰草属、慈姑属、雨火花属、飘拂草属、荸荠属、鸭咀草属和Apera。
本发明化合物的用量视芽前和芽后的使用方法而定,在0.001至5公斤/公顷之间的范围内变化。
本发明的活性物质也可用作脱叶剂、脱水剂和消灭杂草的农药。它们也影响植物生长,因此可用来影响人工培植植物的生长。有些活性物质还显示出杀真菌作用。
本发明的这些化合物可以单独使用,彼此混合使用或者与其它活性物质混合使用,按所希望的目的而定,必要时可以加入其它植物保护剂或杀虫剂。如果有意扩大作用范围,也可加入其它除草剂,例如在Weed Abstracts,Vd,38,No,3,1989,标题为“List of common names and abbrevia-tions employed for currently used herbicides and plant growth vegulators in weed Abstracts”中列举的那些活性物质就适合于作有效的除草混合组份。
为了提高本发明化合物的有效强度和作用速度,例如可加入合适的添加剂如有机溶剂、浸透剂和油类,因此在这情况下这样一些添加剂可减少活性物质的规定剂量。
在所述的活性组分或其混合物中添加液态载体物质和/或固态载体物质或添加稀释剂,必要时还添加胶粘剂、乳化剂和/或分散助剂制成如粉剂、撒布剂、粒剂、溶液、乳状液或悬浮体来应用是适宜的。
合适的液态载体物质有例如脂肪烃和芳香烃如苯、甲苯、二甲苯环己酮、异佛尔酮、二甲基亚砜、二甲基甲酰胺,此外还有石油馏份和植物油。
适合于作固态载体物质为矿物,例如皂土、硅胶、滑石、高岭土活性白土、石灰石和植物产品,例如面粉。
应该提到的表面活性剂有例如木素磺酸钙、聚乙烯烷基苯醚、萘磺酸及其盐、苯磺酸及其盐、甲醛缩合物、脂肪醇硫酸酯以及取代的苯磺酸和其盐。
不同制剂中的活性物质份量可以在宽广的范围变动。例如农药制剂含有约10到90重量%活性物质、约90至10重量%液态载体物质或固态载体物质以及必要时还含有多至20重量%表面活性剂。
农药的施用可按通常的方法进行,例如以水为载体,喷布药液量约为100至1000升/公顷。以所谓低体积和超低体积方法使用农药正如以所谓微粒形式使用农药一样是可能的。
这些制剂的制备可用已知的方法进行,例如用磨细法和混合法。如有必要,可在临使用前才将已准备好的各组份加以混合,例如实际上以所谓桶混合法进行。
为了制备不同的制剂可用例如如下配方:
A)可湿性粉剂
1)25重量% 活性组分
60重量% 高岭土
10重量% 硅酸
5重量% 木素碳酸钙和N-甲基-N-油酰牛磺酸钠的混合物
2)40重量% 活性组分
25重量% 白土矿物
25重量% 硅酸
10重量% 木素磺酸钙和烷基苯基聚乙二醇醚的混合物
B)糊剂
45重量% 活性组分
5重量% 硅酸铝钠
15重量% 带有8摩尔环氧乙烷的鲸蜡基聚乙二醇醚
2重量% 锭子油
10重量% 聚乙二醇
23重量% 水
C)浓乳状液
25重量% 活性组分
15重量% 环己酮
55重量% 二甲苯
5重量% 十二烷基苯磺酸钙和壬基苯基聚氧乙烯的混合物
以下实施例说明本发明化合物的制备方法:
实施例1
2-(4,6-二甲氧基-2-嘧啶硫基-3-苯基丙烯酸甲酯
在氮气保护下,在80毫升四氢呋喃中先加入2.8克(28.7毫摩尔)二异丙基胺,然后在-78至-50℃的温度下加入11.5毫升(28.7毫摩尔)溶在己烷中的2.5M正丁基锂。搅拌10分钟后慢慢地将溶解在80毫升四氢呋喃中的7克(28.7毫摩尔)2-(4,6-二甲氧基-2-嘧啶硫基)-醋酸甲酯加到反应溶液中,加完后还搅拌20分钟。然后将2.8克(28.7毫摩尔)苯甲醛慢慢滴入溶液中。在搅拌下让反应溶液自己慢慢升温至室温,再搅拌16小时。在反应物料中加500毫升水,并用醋酸乙酯进行彻底萃取。将用硫酸镁干燥过的醋酸乙酯相浓缩,接着以己烷/醋酸乙酯为洗提剂用中等压力色层分离法进行精制。
产量:6.1克=理论量的63.9%
η20 D1.5926
原料的制备
2-(4,6-二甲氧基-2-嘧啶硫基)-醋酸甲酯
在250毫升二甲基甲酰胺中先加入25克(230毫摩尔)巯基醋酸甲酯,然后加入16.3克(115毫摩尔)碳酸钾。搅拌20分钟后在室温下加入50克(230毫摩尔)4,6-二甲氧基-2-甲磺酰嘧啶,并升温至90℃加热三小时。随后把反应混合物倒入水中,用醋酸乙酯萃取。用水洗涤有机相,随后用硫酸镁进行干燥。蒸去溶剂,使得到的粗品在二异丙醚中重结晶。
产量:44.6克=理论量的79.4%
熔点:67-69℃
实施例2
2-(4,6-二甲氧基-2-嘧啶硫基)-3-苯基丙烯酸
将0.5克(1.5毫摩尔)2-(4,6-二甲氧基-2-嘧啶硫基)-3-苯基丙烯酸甲酯和95毫克(1.7毫摩尔)氢氧化钾加到由5毫升水和5毫升乙醇组成的混合物中,并在50℃加热8小时。用约100毫升水稀释此混合物,并用醋酸乙酯进行萃取。用10%的盐酸将水相酸化至pH值到达2,并用醋酸乙烯萃取。用硫酸镁干燥醋酸乙酯相之后在真空下蒸去溶剂,使剩余物在二异丙醚中重结晶。
产量:0.25克=理论量的52%
熔点:162-164℃
用类似方法也可制备通式Ⅰ所示的以下一些化合物:
以下实施例说明本发明化合物的使用范围:
实施例A
在暖房中用上面提到的化合物按0.1公斤活性物质/公顷的用量处理上面提到过的发芽后的植物物种。为此目的将这些化合物按每公顷500升水的量以乳状液或悬浮体均匀地喷洒到植物上。处理后两周,本发明化合物显示出极好的抗杂草作用和对小麦和玉米作物的高度的选择性,作对比试验的农药未显示出同样好的效果。
下表中表示:
0=无损害
1=1-24%受损
2=25-74%受损
3=75-89%受损
4=90-100受损
TRZAX=小麦属aestivum
ZEAMX=玉米属mays
GALAP=猪殃殃属aparine
SEBEX=田菁属exaltata
SOLSS=茄属Sp。
T Z G S S
R E A E O
Z A L B L
本发明化合物 X X P X S
实施例1 0 0 3 3 3
未处理过的 0 0 0 0 0
对比农药
2-(4-异丙基 0 0 1 1 0
-4-甲基-5-
氧代-2-咪唑啉
-2-基)-4
(5)-甲基苯甲
酸甲酯
实施例B
在暖房中用上面提到的化合物按0.1公斤活性物质/公顷的用量处理上面提到过的发芽前的植物物种。为此目的而将这些化合物按每公顷500升水的量以乳状液或悬浮体均匀地喷洒到土壤中。处理后叁周本发明化合物显示出极好的抗杂草作用和对小麦和玉米作物的高度的选择性。作对比试验的农药未显示出同样好的效果。
下表中表示:
0=无损害
1=1-24%受损
2=25-74%受损
3=75-89%受损
4=90-100%受损
TRZAX=小麦属aestivum
VERPE=婆婆纳属桃属
VIOSS=堇菜属Sp。
T V V
R E I
Z R O
A P S
本发明化合物 X E S
实施例13 0 3 3
实施例25 0 3
未处理过的 0 0 0
对比农药
2-(4-异丙基- 0 1 2
4-甲基-5-氧代
-2-咪唑啉-2-
基)-4(5)-甲
基苯甲酸甲酯
Claims (7)
1、一种除草组合物,该组合物含有通式I所示的取代的嘧啶氧基(硫基)丙烯酸衍生物和三嗪氧基(硫基)丙烯酸衍生物,以及它们的碱金属盐、碱土金属盐、有机铵盐和它们的E-同分异构体和Z-同分异构体,
式中:
A为通式A-1至A-6所示的基团之一;
C1-C10-烷基;被C1-C4-烷氧基、C1-C4-烷硫基、氨基、C1-C4烷基、二-C1-C4-烷氨基、硝基、三氟甲基、卤素或苯基进行过一次或多次、相同基或不同基取代的C1-C10-烷基;C2-C10-烯基;被C1-C4-烷氧基、C1-C4-烷硫基、氨基、C1-C4烷氨基、二-C1-C4-烷氨基、硝基、三氟甲基、卤素或苯基进行过一次或多次、相同基或不同基取代的C2-C10-烯基;C2-C10炔基;被C1-C4烷氧基、C1-C4-烷硫基、氨基、C1-C4-烷氨基、二-C1-C4-烷氨基、硝基、三氟甲基、卤素或苯基进行过一次或多次、相同基或不同基取代的C2-C10-炔基;C2-C6-环烷基;被C1-C4-烷基、C1-C4-烷氧基、C1-C4烷硫基、氨基、C1-C4-烷氨基、二-C1-C4-烷氨基、硝基、三氟甲基、卤素或苯基进行过一次或多次、相同或不同基取代的C3-C8-环烷基;C4-C8-环烯基;被C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷硫基、氨基、C1-C4烷氨基、二-C1-C4-烷氨基、硝基、三氟甲基、卤素、或苯基进行过一次或多次,相同基或不同基取代的C4-C8-环烯基,
D为氧原子、硫原子或-NR’-
G为氢原子或C1-C6-烷基,
R1为氢原子、C1-C4-烷基或苄基,
R2为C1-C4烷基、C1-C4烷氧基、C1-C4-烷硫基、C1-C4-烷氨基、二-C1-C4-烷氨基或卤素原子,
R3为C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷硫基、C1-C4-烷氨基、二-C1-C4-烷氨基或卤素原子,
R4为氢原子、C1-C4-烷基、C1-C4-烷氧基、氨基、二-C1-C4-烷氨基、硝基、卤素原子、三氟甲基或苯基,
R5为氢原子、C1-C4-烷基、C1-C4-烷氧基、氨基、二-C1-C4-烷氨基、硝基、卤素原子、三氟甲基或苯基,
R6为氢原子、C1-C4-烷基、C1-C4-烷氧基、氨基、二-C1-C4-烷氨基、硝基、卤素原子、三氟甲基或苯基,
R7为氢原子、C1-C4-烷基、C1-C4-烷氧基、氨基、二-C1-C4-烷氨基、硝基、卤素原子、三氟甲基或苯基,
R8为氢原子、C1-C4-烷基、C1-C4-烷氧基、氨基、二-C1-C4-烷氨基、硝基、卤素原子三氟甲基或苯基,
R9为氢原子、C1-C4-烷基或苯基,
X为氧原子或硫原子,
Y为次甲基或氮原子,
上述化合物与农用载体或稀释剂相混合。
2、通式Ⅰ所示化合物的制备方法,其特征在于:
A)使通过Ⅱ所示的化合物在合适的溶剂中在有合适的碱存在下和通式Ⅲ所示的化合物进行反应;
式中R1、R2、R3、X和Y有通式Ⅰ中所述的意义;
式中A和G有通式Ⅰ中所述意义;
或B)使通式Ⅳ所示的化合物在合适的极性溶剂中与碱金属碱、碱土金属碱或有机碱反应成通式Ⅴ所示的化合物,
式中A、G、R1、R2、R3、X和Y有通式Ⅰ中所述意义,
式中A、G、R2、R3、X和Y有通式Ⅰ中所述意义,M代表碱金属原子、当量碱土金属原子或有机铵盐;
或C)使通式Ⅴ所示的化合物在合适的溶剂中与合适的酸反应成通式Ⅵ所示的化合物,
式中A、G、R2、R3、M、X和Y有通式Ⅴ中所述意义,
式中A、G、R2、R3、X和Y有通式Ⅰ中所述意义,
或D)使通式Ⅳ所示的化合物在合适的溶剂中与合适的酸反应成通式Ⅵ所示的化合物,
式中A、G、R2、R3、X和Y有通式Ⅰ中所述意义,R1代表C1-C4-烷基或苄基,
式中A、G、R3、X和Y有通式Ⅰ中所述意义。
3、具有除草、杀真菌和调节植物生长作用的农药,其特征在于含有按权利要求1所述的至少一种化合物。
4、按权利要求3所述的农药用来防除主要农作物中的单子叶杂草和双子叶杂草的用途。
5、按权利要求3所述的农药用来消灭农作物中真菌侵害的用途。
6、按权利要求3所述的农药用来影响农植物的生长的用途。
7、具有除草、杀真菌和调节植物生长作用的农药的制备方法,其特征在于:将按权利要求1所述的通式Ⅰ所示的化合物与载体物质和/或辅助物质混合。
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DE3924260.9 | 1989-07-19 | ||
DE3924260A DE3924260A1 (de) | 1989-07-19 | 1989-07-19 | Substituierte pyrimidinyloxy(thio)- und triazinyloxy(thio)-acrylsaeurederivate, verfahren zu ihrer herstellung und ihre verwendung als mittel mit herbizider, fungizider und pflanzenwachstumsregulierender wirkung |
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US (1) | US5089044A (zh) |
JP (1) | JPH03135964A (zh) |
CN (1) | CN1048851A (zh) |
AU (1) | AU5909990A (zh) |
CA (1) | CA2021427A1 (zh) |
DD (1) | DD296597A5 (zh) |
DE (1) | DE3924260A1 (zh) |
HU (1) | HUT54354A (zh) |
ZA (1) | ZA905701B (zh) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
PT100941A (pt) * | 1991-10-11 | 1993-10-29 | Ciba Geigy Ag | Herbicidas a base de eteres ou tioeteres pirimidinilicos ou triazinilicos, e processo para a sua preparacao |
US5446155A (en) * | 1992-10-07 | 1995-08-29 | General Electric Company | Method for preparing disubstituted monochlorotriazines |
DE4423485A1 (de) * | 1994-07-05 | 1996-01-11 | Basf Ag | Thiazolmethinfarbstoffe |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0739394B2 (ja) * | 1985-05-30 | 1995-05-01 | 住友化学工業株式会社 | 含窒素複素環化合物およびそれを有効成分として含有する有害生物防除剤 |
DE68914197T2 (de) * | 1988-06-20 | 1994-11-10 | Kumiai Chemical Industry Co | Alkansäurederivate und herbizide Mittel. |
US4973354A (en) * | 1988-12-01 | 1990-11-27 | Nissan Chemical Industries, Ltd. | Pyrimidine derivatives and herbicide containing the same |
-
1989
- 1989-07-19 DE DE3924260A patent/DE3924260A1/de not_active Withdrawn
-
1990
- 1990-07-18 CN CN90104761A patent/CN1048851A/zh active Pending
- 1990-07-18 HU HU904538A patent/HUT54354A/hu unknown
- 1990-07-18 AU AU59099/90A patent/AU5909990A/en not_active Abandoned
- 1990-07-18 CA CA002021427A patent/CA2021427A1/en not_active Abandoned
- 1990-07-18 DD DD90342878A patent/DD296597A5/de not_active IP Right Cessation
- 1990-07-19 US US07/555,585 patent/US5089044A/en not_active Expired - Fee Related
- 1990-07-19 JP JP2189608A patent/JPH03135964A/ja active Pending
- 1990-07-19 ZA ZA905701A patent/ZA905701B/xx unknown
Also Published As
Publication number | Publication date |
---|---|
DD296597A5 (de) | 1991-12-12 |
ZA905701B (en) | 1991-05-29 |
HU904538D0 (en) | 1990-12-28 |
AU5909990A (en) | 1991-01-24 |
US5089044A (en) | 1992-02-18 |
JPH03135964A (ja) | 1991-06-10 |
HUT54354A (en) | 1991-02-28 |
DE3924260A1 (de) | 1991-01-31 |
CA2021427A1 (en) | 1991-01-20 |
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