CN1298399A - 取代的烷氧基羰基化合物 - Google Patents
取代的烷氧基羰基化合物 Download PDFInfo
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- CN1298399A CN1298399A CN 99805262 CN99805262A CN1298399A CN 1298399 A CN1298399 A CN 1298399A CN 99805262 CN99805262 CN 99805262 CN 99805262 A CN99805262 A CN 99805262A CN 1298399 A CN1298399 A CN 1298399A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 83
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 37
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 18
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- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 10
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- 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
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
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- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
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- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
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- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
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- C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C323/11—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
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- C07D209/04—Indoles; Hydrogenated indoles
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- C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
- C07D215/08—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms with acylated ring nitrogen atom
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- C07D217/06—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with the ring nitrogen atom acylated by carboxylic or carbonic acids, or with sulfur or nitrogen analogues thereof, e.g. carbamates
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- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
- C07D295/28—Nitrogen atoms
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- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
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Abstract
本发明涉及新的通式(Ⅰ)的取代的烷氧基羰基化合物,其中,n表示数字0或1,Ar表示均可任选被取代的单环状或双环状饱和或任选部分不饱和的碳环或杂环基团,Q表示O(氧)、S(硫)、SO、SO2、NH、N(烷基)或CH2(亚甲基),R1表示烷基或环烷基,R2表示氢或烷基,Y表示NH或N(烷基),和Z表示经N结合的均可任选被取代的单环状或双环状饱和或部分不饱和杂环,或-如果n是1或Ar表示双状基团的话-还表示均可任选被取代的环烷基氨基或芳氨基。本发明还涉及所述化合物的生产及其作为处理植物药剂,特别是作为除草剂、杀真菌剂和杀虫剂的应用。
Description
本发明涉及新颖的取代的烷氧基羰基化合物,涉及其制备及其作为作物处理剂,特别是作为除草剂、杀真菌剂和杀虫剂的应用。
已知某些取代的O-芳氧基烷基N-芳基-氨基甲酸酯具有除草性能(参见,US-A-5099059、US-A-5152827、US-A-5194661、US-A-5399545/WO-A-9410132、WO-A-9616941)。然而,这些已知化合物的活性并不完全令人满意。
因此,本发明提供新的通式(Ⅰ)的取代的烷氧基羰基化合物其中n 表示数字0或1,Ar 表示均可任选被取代的单环状或双环状的饱和或-如果适宜的话部分地-不饱和的碳环或杂环基团,Q 表示O(氧)、S(硫)、SO、SO2、NH、N(烷基)或CH2(亚甲基),R1 表示烷基或环烷基,R2 表示氢或烷基,Y 表示NH或N(烷基),和Z 表示经N连接的均可任选被取代的单环状或双环状的饱和或部分不饱和的杂环,或-如果n是1或Ar表示双环状基团的话-还表示均可任选被取代的环烷基氨基或芳氨基。
本发明通式(Ⅰ)化合物含有至少一个不对称取代的碳原子且因此存在各种对映体(R-和S-构型)或非对映体形式。本发明涉及通式(Ⅰ)化合物的各种可能单个对映体或立体异构体形式以及这些立体异构体化合物的混合物。
在其定义中,烃链如烷基-包括与杂原子的组合如烷氧基-在每一情况下是直链或支链。Ar 优选表示选自下列的均可任选被取代的单环或双环状的饱和或-如果适宜的话部分地-不饱和的碳环或杂环状基团:环戊基、环己基、苯基、萘基、四氢化萘基、十氢化萘基、呋喃基、苯并呋喃基、噻吩基、苯并噻吩基、噁唑基、苯并噁唑基、噻唑基、苯并噻唑基、吡唑基、吡啶基、喹啉基、异喹啉基、嘧啶基,或任选被取代的下列基团
其中A表示任选卤代的具有1至3个碳原子的烷二基,其中在每一种情况下可能的取代基优选选自下列:
氰基、硝基、卤素、均可任选卤代的各具有至多6个碳原子的烷基、烷氧基、烷硫基、烷基亚磺酰基、烷基磺酰基、烷基羰基、烷氧基羰基;Q 优选表示O(氧)、S(硫)、SO、SO2、NH、N(C1-C4-烷基)或CH2(亚甲基);R1 优选表示具有1至6个碳原子的烷基或表示具有3至6个碳原子的环烷基;R2 优选表示氢或具有1至4个碳原子的烷基;Y 优选表示NH或N(C1-C4-烷基);和Z 优选表示均可任选被取代的氮杂环丙烷基、氮杂环丁烷基、吡咯烷基、哌啶基、吗啉基、硫代吗啉基、S-氧代-硫代吗啉基、S,S-二氧代-硫代吗啉基、全氢氮杂基、哌嗪基、吲哚基、异吲哚基、全氢吲哚基、全氢异吲哚基、四氢喹啉基、全氢喹啉基、四氢异喹啉基或全氢异喹啉基,它们均经N连接,或-如果n是1或Ar表示双环状基团的话-还表示均可任选被取代的具有3至6个碳原子的环烷基氨基或具有6或10个碳原子的芳基氨基,其中在每一种情况下可能的取代基优选选自下列:氰基、硝基、卤素、均可任选卤代的各具有至多6个碳原子的烷基、烷氧基、烷硫基、烷基亚磺酰基、烷基磺酰基、烷基羰基、烷氧基羰基;
Ar特别优选表示选自下列的均可任选被取代的单环状或双环状的饱和或-如果适宜的话部分地-不饱和的碳环状或杂环状基团:环己基、苯基、萘基、四氢化萘基、十氢化萘基、呋喃基、苯并呋喃基、噻吩基、苯并噻吩基、噁唑基、苯并噁唑基、噻唑基、苯并噻唑基、吡唑基、吡啶基、喹啉基、异喹啉基、嘧啶基,或同样任选被取代的下列基团其中A表示任选由氟-和/或氯-取代的亚甲基或二亚甲基(乙-1,2-二基),其中在每一种情况下可能的取代基优选选自下列:氰基、硝基、氟、氯、溴、各任选由氟-和/或氯-取代的甲基、乙基、正或异丙基、正-、异-、仲-或叔丁基、甲氧基、乙氧基、正-或异丙氧基、正-、异-、仲-或叔丁氧基、甲硫基、乙硫基、正-或异丙硫基、正-、异-、仲-或叔丁硫基、甲基亚磺酰基、乙基亚磺酰基、正-或异丙基亚磺酰基、甲基磺酰基、乙基磺酰基、正-或异丙基磺酰基、乙酰基、丙酰基、正-或异丁酰基、甲氧基羰基、乙氧基羰基、正-或异丙氧基羰基;Q特别优选表示O(氧)、S(硫)、SO、SO2、NH、N(甲基)或CH2(亚甲基);R1 特别优选表示甲基、乙基、正-或异丙基,或表示环丙基;R2 特别优选表示氢或甲基;Y特别优选表示NH、N(甲基)、N(乙基)或N(异丙基);和Z特别优选表示均可任选被取代的吡咯烷基、哌啶基、吗啉基、硫代吗啉基、S-氧代-硫代吗啉基、S,S-二氧代-硫代吗啉基、全氢氮杂卓基、哌嗪基、吲哚基、异吲哚基、全氢吲哚基、全氢异吲哚基、四氢喹啉基、全氢喹啉基、四氢异喹啉基或全氢异喹啉基,它们均经N连接,或-如果n是1或Ar表示双环状基团的话-还表示均可任选被取代的环己基氨基或苯基氨基,其中在每一种情况下可能的取代基优选选自下列:氰基、硝基、氯、氟、溴、均可任选由氟-和/氯取代的甲基、乙基、正或异丙基、正-、异-、仲-或叔丁基、甲氧基、乙氧基、正-或异丙氧基、正-、异-、仲-或叔丁氧基、甲硫基、乙硫基、正-或异丙硫基、正-、异-、仲-或叔丁硫基、甲基亚磺酰基、乙基亚磺酰基、正-或异丙基亚磺酰基、甲基磺酰基、乙基磺酰基、正-或异丙基磺酰基、乙酰基、丙酰基、正-或异丁酰基、甲氧基羰基、乙氧基羰基、正-或异丙氧基羰基;Q 特别优选表示氧;R1 特别优选表示甲基、乙基、正-或异丙基;Ar 特别优选表示下列基团
其中
R3表示氟、氯、溴、甲基、乙基、三氟甲基、甲氧基、二氟甲氧基或三氟甲氧基,和
R4表示氢、氟、氯、甲基或三氟甲基;Q 还非常特别优选表示CH2(亚甲基);Ar 还非常特别优选表示下列基团之一上面提到的一般或优选的基团定义适合于式(Ⅰ)终产物,且相应地,也适合于在每一种制备情况下所需的起始原料或中间体。这些基团定义可以按照需要相互结合,即,包括上面提到的优选范围间的组合。
本发明优选的是含有上面作为优选含义给出的含义之组合的式(Ⅰ)化合物。
本发明特别优选的是含有上面作为特别优选含义给出的含义之组合的式(Ⅰ)化合物。
本发明非常特别优选的是含有上面作为非常特别优选含义给出的含义之组合的式(Ⅰ)化合物。
本发明通式(Ⅰ)化合物的特别优选的实例分组列于下文。组1n 表示数字O或1,Y表示NH、N(甲基)、N(乙基)或N(异丙基),和Z具有下文给出的含义:组2n、Y和Z具有组1中给出的含义。组3n、Y和Z具有组1中给出的含义。组4n、Y和Z具有组1中给出的含义。组5n、Y和Z具有组1中给出的含义。组6n、Y和Z具有组1中给出的含义。组7n、Y和Z具有组1中给出的含义。组8n、Y和Z具有组1中给出的含义。组9n、Y和Z具有组1中给出的含义。组10n、Y和Z具有组1中给出的含义。组11n、Y和Z具有组1中给出的含义。组12n、Y和Z具有组1中给出的含义。组13n、Y和Z具有组1中给出的含义。组14n、Y和Z具有组1中给出的含义。组15n、Y和Z具有组1中给出的含义。组16n、Y和Z具有组1中给出的含义。组17n、Y和Z具有组1中给出的含义。组18n、Y和Z具有组1中给出的含义。组19n、Y和Z具有组1中给出的含义。组20n、Y和Z具有组1中给出的含义。组21n、Y和Z具有组1中给出的含义。
新的通式(Ⅰ)的取代的烷氧基羰基化合物具有重要的生物性能;特别是,它们具有强且有选择性的除草活性和杀真菌和杀虫活性。
新的通式(Ⅰ)的取代的烷氧基羰基化合物如下获得:
(a)如果适宜在反应辅助剂存在下和如果适宜在稀释剂存在下,使通式(Ⅱ)的取代的链烷醇与通式(Ⅲ)的异氰酸酯反应,其中Ar、Q、R1和R2如上定义,
H-(Y)n-Z (Ⅴ)其中n、Y和Z如上定义。
式(Ⅱ)提供在制备本发明式(Ⅰ)化合物的本发明方法(a)中用作起始原料的取代的链烷醇的一般定义。在式(Ⅱ)中,Ar、Q、R1和R2各优选或特别是具有在上文有关本发明式(Ⅰ)化合物的描述中业已提到的Ar、Q、R1和R2的优选或特别优选的含义。
式(Ⅱ)起始原料是已知和和/或可以通过已知的方法制备(参见,US-A-5099059、US-A-5152827、US-A-5194661、US-A-5399545,参见制备实施例)。
通式(Ⅲ)提供在本发明方法(a)中另一用作起始原料的异氰酸酯的一般定义。在式(Ⅲ)中,Z优选或特别是具有在上文有关本发明式(Ⅰ)化合物的描述中业已提到的Z的优选或特别优选的含义。
式(Ⅲ)起始原料是合成上已知的有机化学品。
式(Ⅳ)提供在制备本发明式(Ⅰ)化合物的本发明方法(b)中用作起始原料的氯甲酸酯的一般定义。在式(Ⅳ)中,Ar、Q、R1和R2各优选或特别是具有在上文有关本发明式(Ⅰ)化合物的描述中业已提到的Ar、Q、R1和R2的优选或特别优选的含义。
式(Ⅳ)起始原料是已知的和/或可以通过已知的方法制备(参见,US-A-5099059、US-A-5152827、US-A-5194661、US-A-5399545,参见制备实施例)。
通式(Ⅴ)提供在本发明方法(b)中另一用作起始原料的亲核化合物的一般定义。在式(Ⅴ)中,n、Y和Z优选或特别是具有在上文有关本发明式(Ⅰ)化合物的描述中业已提到的n、Y和Z的优选或特别优选的含义。
式(Ⅴ)起始原料是合成上已知的有机化学品。
适合于方法(a)和(b)的反应辅助剂通常是常规的无机或有机碱或酸受体。这些物质优选包括碱金属或碱土金属的乙酸盐、氨化物、碳酸盐、碳酸氢盐、氢化物、氢氧化物或醇盐,如乙酸钠、乙酸钾或乙酸钙、氨化锂、氨化钠、氨化钾或氨化钙、碳酸钠、碳酸钾或碳酸钙、碳酸氢钠、碳酸氢钾或碳酸氢钙、氢化锂、氢化钠、氢化钾或氢化钙、氢氧化锂、氢氧化钠、氢氧化钾或氢氧化钙、甲醇、乙醇、正或异丙醇、正-、异-、仲-或叔丁醇的钠盐或甲醇、乙醇、正-或异丙醇、正-、异-、仲-或叔丁醇的钾盐;另外还有碱性有机氮化合物,如,三甲胺、三乙胺、三丙胺、三丁胺、乙基-二异丙胺、N,N-二甲基-环己基胺、二环己基胺、乙基-二环己基胺、N,N-二甲基苯胺、N,N-二甲基-苄基胺、吡啶、2-甲基-、3-甲基-、4-乙基-、2,4-二甲基-、2,6-二甲基-、3,4-二甲基-和3,5-二甲基-吡啶、5-乙基-2-甲基-吡啶、4-二甲基氨基-吡啶、N-甲基-哌啶、1,4-二氮杂二环[2,2,2]-辛烷(DABCO)、1,5-二氮杂二环[4,3,0]-壬-5-烯(DBN)或1,8-二氮杂二环[5,4,0]-十一-7-烯(DBU)。
在本发明方法(b)中,通式(Ⅴ)的亲核化合物用作起始原料-适当过量采用-同时可以任选作为反应辅助剂。
适合于进行本发明方法(a)和(b)的稀释剂特别是惰性有机溶剂。这些物质包括特别是脂肪族、脂环族或芳族的任选卤代的烃,诸如,例如汽油、苯、甲苯、二甲苯、氯苯、二氯苯、石油醚、己烷、环己烷、二氯甲烷、氯仿、四氯化碳;醚类,如乙醚、异丙醚、二噁烷、四氢呋喃或乙二醇二甲醚或乙二醇二乙醚;酮类,如丙酮、丁酮或甲基异丁酮;腈类,如乙腈、丙腈或丁腈;酰胺类,如N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基-甲酰苯胺、N-甲基吡咯烷酮或六甲基磷酰三胺;酯类,如乙酸甲酯或乙酸乙酯;亚砜类,如二甲基亚砜;醇类,如甲醇、乙醇、正-或异丙醇、乙二醇单甲醚、乙二醇单乙醚、二甘醇单甲醚、二甘醇单乙醚,它们与水的混合物,或纯水。
进行本发明方法(a)和(b)时,反应温度可以在相对宽的范围内进行的。通常,反应是在0℃至150℃,优选在10℃至120℃间的温度下进行。
本发明的方法(a)和(b)通常是在常压下进行的。然而,本发明方法也可以在加压或减压下——通常是在0.1巴至10巴间的压力下进行。
进行本发明方法(a)和(b)时,通常采用大致等摩尔量的起始原料。然而,也可以相对大地过量采用反应组分之—。反应通常是在适合的稀释剂中,适当的话在反应辅助剂存在下进行的,且反应混合物通常在所需的温度下搅拌几小时。后处理是用常规方法进行(参见,制备实施例)。
本发明活性化合物可以用作脱叶剂、干燥剂、杀茎杆剂,和特别是用作除草剂。所谓的杂草,就其最广义而言,应理解为生长在不该生长的地方的所有植物。本发明的物质是作为灭生性除草剂或是选择性除草剂基本上取决于所用的量。
本发明化合物可以与例如下列植物相关使用:
下列属的双子叶杂草:芥属、独行草属、猪殃殃属、繁缕属、母菊属、春黄菊属、牛膝属、藜属、荨麻属、千里光属、苋属、马齿苋属、苍耳属、旋花属、甘薯属、蓼属、田菁属、豚草属、蓟属、飞廉属、苦苣菜属、茄属、蔊菜属、节节草属、母草属、野芝麻属、婆婆纳属、苘麻属、刺酸模属、曼陀罗属、堇菜属、鼬瓣花属、罂粟属、矢车菊属、三叶草属、毛茛属和蒲公英属。
下列属的双子叶作物:棉属、大豆属、甜菜属、胡萝卜属、菜豆属、豌豆属、茄属、亚麻属、甘薯属、巢菜属、烟草属、蕃茄属、花生属、芸苔属、莴苣属、黄瓜属和南瓜属。
下列属的单子叶杂草:稗属、狗尾草属、黍属、马唐属、梯牧草属、早熟禾属、羊茅属、蟋蟀草属、臂形草属、黑麦草属、雀麦属、燕麦属、莎草属、高梁属、冰草属、狗牙根属、雨久花属、飘拂草属、慈菇属、荸荠属、藨草属、雀稗属、鸭嘴草属、尖瓣花属、龙爪茅属、剪股颖属、看麦娘属和风草属。
下列属的单子叶作物:稻属、玉米属、小麦属、大麦属、燕麦属、黑麦属、高梁属、黍属、甘蔗属、凤梨属、天门冬属和葱属。
然而,本发明活性化合物的应用决不限于这些属,且也可以相同的方式延伸至其它植物。
取决于化合物的浓度,化合物适合于灭生性防治杂草,例如工业地域和铁道线,以及有或无种植树林的道路和广场。同样,化合物可以用于防治多年生作物中的杂草,例如森林、装饰树林、果园、葡萄园、柑桔林、坚果园、蕉种植园、咖啡种植园、茶园、橡胶种植园、油棕榈种植园、可可种植园、软果林和啤酒花田、草场、体育场和牧场中的杂草。且本发明化合物还可以用于选择性地防治一年生作物中的杂草。
本发明式(Ⅰ)化合物特别适合于以芽前和芽后二种方式选择性地防治单子叶和双子叶作物中的单子叶和双子叶杂草。
本发明活性化合物具有强的杀微生物活性,且可以采用来防治作物保护和材料保护中的有害微生物。本发明活性化合物适合用作杀真菌剂。
杀真菌剂可以用在作物保护中,用于防治根肿菌纲、卵菌纲、壶菌纲、接合菌纲、子囊菌纲、担子菌纲和半知菌类。
杀细菌剂可以用在作物保护中,用于防治如假单胞菌科、根瘤菌科、肠杆菌科、棒状杆菌科和链霉菌科。
上面列出的某些病原真菌病害以属名给出,可以提到的非限定性实例有:
黄单胞菌属,如田野黄单胞菌稻变种(Xanthomonas campestrispv.oryzae);
假单胞菌属,如黄瓜细菌性角斑病菌(Pseudomonas syringaepv lachrymans);
欧文氏菌属,如解淀粉欧文氏菌(Erwinia amylovora);
腐霉属,如终极腐霉(Pythium ultimum);
疫霉属,如蔓延疫霉(Phytophthora infestans);
假霜霉属,如律草假霜霉(Pseudoperonospora humuli)或古巴假霜霉(P.cubensis);
单轴霉属,如葡萄生单轴霉(Plasmopara viticola);
盘梗霉属,如莴苣盘梗霉(Bremia laceucae)
霜霉属,如豌豆霜霉(Peronospora pisi)或芸苔霜霉(P.brassicae);
白粉菌属,如禾白粉菌(Erysiphe graminis);
单丝壳属,如苍耳单丝壳菌(Sphaerotheca fuliginea);
柄球菌属,如苹果白粉病柄球菌(Podosphaera leucotricha);
黑星菌属,如苹果黑星菌(Venturia inaequalis);
核腔菌属,如圆核腔菌(Pyrenophora teres)或麦类核腔菌(P.graminea)(分生孢子形式:Drechslera,异名:长蠕孢属(Helminthosporium));
旋孢腔菌属,如禾旋孢腔菌(Cochliobolus sativus)(分生孢子形式:Drechslera,异名:长蠕孢属(Helminthosporium));
单孢锈属,如菜豆单孢锈菌(Uromyces appendiculatus);
柄锈属,如隐匿柄锈菌(Puccinia recondita);
核盘菌属,例如油菜核盘菌(Sclertinia sclerotiorum);
腥黑粉菌属,如小麦网腥黑粉菌(Tilletia caries);
黑粉菌属,如裸黑粉菌(Ustilago nuda)或燕麦散黑粉菌(U.avenae);
薄膜革菌属,如佐佐木氏薄膜革菌(Pellicularia sasakii);
梨孢菌属,如稻梨孢菌(Pyricularia oryzae);
镰孢属,如大刀镰孢(Fusarium culmorum);
葡萄孢属,如灰色葡萄孢(Botrytis cinerea);
壳针孢属,如颖枯壳针孢(Septoria nodorum);
小球腔菌属,如颖枯病小球腔菌(Leptosphaeria nodorum);
尾孢属,如变灰尾孢菌(Cercospora canescens);
链格孢属,如甘蓝黑斑病链格孢菌(Alternaria brassicae),和
假小尾孢菌属,如柔毛假小尾孢菌(Pseudocercosporallaherpotrichoides)。
本发明通式(Ⅰ)的活性化合物可特别有效地防治白粉病(Erysiphegraminis)。
在防治植物病害所需浓度下,本发明活性化合物被植物很好地耐受这一事实,使得活性化合物可以处理植物的地上部分、无性繁殖原种和种子以及土壤。
本发明活性化合物还适合防治动物害虫,优选节肢动物和线虫,特别是出现在农业、森林、贮藏产品和材料保护以及卫生方面上的昆虫、蜱螨。它们对正常的敏感和抗性种类和对所有或某些生长发育阶段有活性。上述害虫包括:
等足目,例如,潮虫(Oniscus asellus)、鼠妇(Armadillidiumvulgare)和斑鼠妇(Porcellio scaber)。
倍足目,例如,具斑马陆(Blaniulus guttulatus)。
唇足目,例如,食果地蜈蚣(Geophilus carpophagus)和蚰蜒(Scutigera spec)。
综合目,例如,洁幺蚰(Scutigerella immaculata)。
缨尾目,例如,西洋衣鱼(Lepisma saccharina)。
弹尾目,例如,具棘跳虫(Onychiurus armatus)。
直翅目,例如,东方蜚蠊(Blatta orientalis)、美洲大蠊(Periplaneta americana)、马德拉蜚蠊(Leucophaea maderae)、德国小蠊(Blattella germanica)、家蟋蟀(Acheta domesticus)、蝼蛄属(Gryllotalpa spp.)、热带飞蝗(Locusta migratoriamigratorioids)、殊种蚱蜢(Melanoplus differentialis)和沙漠蝗(Schistocerca gregaria)。
革翅目,例如,欧洲球螋(Forficula auricularia)。
等翅目,例如,犀白蚁属(Reticulitermes spp.)。
虱目,例如,体虱(Pediculus humanus corporis)、血虱属(Haematopinus spp.)和颚虱属(Linognathus spp.)。
食毛目,例如,啮毛虱属(Trichodectes spp.)和畜属虱(Damalinea spp.)。
缨翅目,例如,温室条蓟马(Hercinothrips femoralis)和棉蓟马(Thrips tabaci)。
半翅目,例如,扁盾蝽属(Eurygaster spp.)、中棉红蝽(Dysdercus intermedius)、甜菜拟网蝽(Piesma quadrata)、温带臭蝽(Cimex lectularius)、长红猎蝽(Rhodnius prolixus)和锥蝽属(Triatoma spp.)。
同翅目,例如,甘蓝粉虱(Aleurodes brassicae)、甘薯粉虱(Bemisia tabaci)、温室粉虱(Trialeurodes vaporariorum)、棉蚜(Aphis gossypii)、甘蓝蚜(Brevicoryne brassicae)、茶藨隐瘤蚜(Cryptomyzus ribis)、甜菜蚜(Aphis fabae)、苹果蚜(Aphispomi)、苹果绵蚜(Eriosoma lanigerum)、桃大尾蚜(Hyalopterusarundinis)、麦长管蚜(Macrosiphum avenae)、瘤额蚜属(Myzusspp.)、瘿绵蚜属(Pemphigus spp.)、忽布疣蚜(Phorodon humili)、美核桃根瘤蚜(Phylloxera vastatrix)、禾谷缢管蚜(Rhopalosiphumpadi)、微叶蝉属(Empoasca spp.)、钝鼻叶蝉(Euscelisbilobatus)、黑尾叶蝉(Nephotettix cincticeps)、水土坚蚧(Lecanium corni)、油榄黑盔蚧(Saissetia oleae)、灰稻虱(Laodelphax striatellus)、稻褐飞虱(Nilaparvata lugens)、红肾园盾蚧(Aonidiella aurantii)、夹竹桃园蚧(Aspidiotushederae)、粉蚧属(Pseudococcus spp.)和木虱属(Psylla spp.)。
鳞翅目,例如,棉红蛉虫(Pectinophora gossypiella)、松天蛾(Bupalus piniarius)、冬尺蛾(Cheimatobia brumata)、苹细蛾(Lithocolletis blancardella)、苹果巢蛾(Hyponomeutapadell a)、小菜蛾(Plutella maculipennis)、天幕毛虫(Malacosomaneustria)、黄毒蛾(Euproctis chrysorrhoea)、毒蛾属(Lymantriaspp.)、棉潜蛾(Bucculatrix thurberiella)、桔潜叶蛾(Phyllocnistis citrella)、地老虎属(Agrotis spp.)、切根虫属(Euxoa spp.)、夜蛾属(Feltia spp.)、棉斑实蛾(Eariasinsulana)、棉铃虫属(Heliothis spp.)、甜菜夜蛾(Spodopteraexigua)、甘蓝夜蛾(Mamestra brassicae)、小眼夜蛾(Panolisflammea)、斜纹夜蛾(Prodenia litura)、灰翅夜蛾属(Spodopteraspp.)、粉纹夜蛾(Trichoplusia ni)、苹蠹蛾(Carpocapsapomonella)、粉蝶属(Pieris spp.)、禾草螟属(Chilo spp.)、玉米螟(Pyrausta nubilalis)、地中海粉斑螟(Ephestiakuehniella)、大蜡螟(Galleria mellonella)、幕衣蛾(Tineolabisselliella)、袋衣蛾(Tinea pellionella)、褐织蛾(Hofmannophila pseudospretella)、亚麻黄卷蛾(Cacoeciapodana)、Capua reticulana、枞色卷蛾(Choristoneurafumiferana)、葡萄果蠹蛾(Clysia ambiguella)、茶长卷蛾(Homonamagnanima)和栎绿卷蛾(Tortrix viridana)。
鞘翅目,例如,具斑窃蠹(Anobium punctatum)、谷蠹(Rhizopertha dominica)、大豆象(Acanthoscelides obtectus)、Bruchidius obtectus、家天牛(Hylotrupes bajulus)、赤杨紫跳甲(Agelasrtica alni)、马铃薯甲虫(Leptinotarsadecemlineata)、辣根猿叶甲(Phaedon cochleariae)、条叶甲属(Diabrotica spp.)、油菜蓝跳甲(Psylliodes chrysocephala)、墨西哥豆甲(Epilachna varivestis)、隐翅甲属(Atomaria spp.)、锯谷盗(Oryzaephilus surinamensis)、花象甲属(Anthonomusspp.)、米象属(Sitophilus spp.)、葡萄黑耳喙象(Otiorrhynchussulcatus)、香蕉根象甲(Cosmopolites sordidus)、甘蓝荚象甲(Ceuthorrhynchus assimilis)、苜蓿叶象虫(Hypera postica)、皮蠹属(Dermestes spp.)、斑皮蠹属(Trogoderma spp.)、圆皮蠹属(Anthrenus spp.)、毛蠹属(Attagenus spp.)、粉蠹属(Lyctusspp.)、油菜花露尾甲(Meligethes aeneus)、蛛甲属(Ptinusspp.)、金黄蛛甲(Niptus hololeucus)、裸蛛甲(Gibbiumpsylloides)、拟谷盗属(Tribolium spp.)、黄粉虫(Tenebriomolitor)、叩头虫属(Agriotes spp.)、宽胸叩头虫属(Conoderusspp.)、西方五月鳃角金龟(Melolontha melolontha)、马铃薯鳃角金龟(Amphimallon solstitialis)和褐新西兰肋翅鳃角金龟(Costelytra zealandica)。
膜翅目,例如,锯角叶蜂属(Diprion spp.)、叶蜂属(Hoplocampaspp.)、田蚁属(Lasius spp.)、小家蚁(Monomorium pharaonis)和胡蜂(Vespa spp.)。
双翅目,例如,伊蚊属(Aedes spp.)、按蚊属(Anophelesspp.)、库蚊属(Culex spp.)、黄猩猩果蝇(Drosophilamelanogaster)、蝇属(Musca spp.)、厕蝇属(Fannia spp.)、红头丽蝇(Callophora erythrocephala)、绿蝇属(Lucilia spp.)、金蝇属(Chrysomyia spp.)、疽蝇属(Cuterebra spp.)、胃蝇属(Gastrophilus spp.)、虱蝇属(Hyppobosca spp.)、螫蝇属(Stomoxys spp.)、狂蝇属(Oestrus spp.)、皮蝇属(Hypodermaspp.)、虻属(Tabanus spp.)、螗蜩属(Tannia spp.)、花园毛蚊(Bibio hortulanus)、瑞典麦杆蝇(Oscinella frit)、草种蝇属(Phorbia spp.)、菠菜潜叶花蝇(Pegomyia hyoscyami)、地中海实蝇(Ceratitis capitata)、油榄实蝇(Dacus oleae)和沼泽大蚊(Tipula paludosa)。
蚤目,例如,印鼠客蚤(Xenopsylla cheopis)和毛列蚤属(Ceratophyllus spp.))。
蛛形目,例如,蝎(Scorpio maurus)和毒寇蛛(Latrodectusmactans)。
蜱螨目,例如,粗脚粉螨(Acarus siro)、隐喙蜱属(Argasspp.)、钝喙蜱属(Ornithodoros spp.)、鸡皮刺螨(Dermanyssusgallinae)、茶藨瘿螨(Eriophyes ribis)、柑桔锈螨(Phyllocoptrutaoleivora)、牛蜱属(Boophilus spp.)、扇头蜱属(Rhipicephalusspp.)、花蜱属(Amblyomma spp.)、玻眼蜱属(Hyalomma spp.)、硬蜱属(Ixodes spp.)、瘙螨属(Psoroptes spp.)、皮螨属(Chorioptesspp.)、疥螨属(Sarcoptes spp.)、跗线螨属(Tarsonemus spp.)、苜蓿苔螨(Bryobia praetiosa)、全爪螨属(Panonychus spp.)和叶螨属(Tetranychus spp.)。
植物寄生线虫包括例如垫刃线虫属(Pratylenchus spp.)、穿孔线虫属(Radopholus spp.)、茎线虫属(Ditylenchus spp.)、小垫刃线虫属(Tylenchulus spp.)、异皮线虫属(Heterodera spp.)、囊线虫属(Globodera spp.)、根结线虫属(Meloidogyne spp.)、滑刃线虫属(Aphelechoides spp.)、长针线虫属(Longidorus spp.)、剑线虫属(Xiphinema spp.)、髦根线虫属(Trichodorus spp.)、Tylenchus spp.、Helicotylenchus spp.、Rotylenchus spp.和Tylenchulus spp.。
它们可以特别成功地采用来防治损害植物的昆虫,例如防治小菜蛾(Plutella spp.)和桃蚜(Mycus spp.)。
活性化合物可以转化成常规的制剂,如溶液、乳剂、可温性粉剂、悬浮剂、粉剂、喷粉剂、膏剂、可溶性粉剂、颗粒剂、悬乳剂、用活性化合物浸渍的天然或合成材料,以及包在聚合物中的微细胶囊。
这些制剂可以用已知的方式生产,例如,将活性化合物与扩充剂,即液体和/或与固体载体混合,并任选使用表面活性剂,即乳化剂和/或分散剂和/或起泡剂。
在用水作扩充剂的情况下,也可以用有机溶剂作助溶剂。适合的液体溶剂主要有:芳族化合物,如二甲苯,甲苯或烷基萘,氯代芳族化合物或氯代脂肪烃,如氯代苯类、氯乙烯类或二氯甲烷,脂族烃,如环己烷或石蜡,例如石油馏份、矿物和植物油,醇类,如丁醇或甘醇以及其醚和酯,酮类,如丙酮、甲乙酮、甲基异丁基酮或环己酮,强极性溶剂,如二甲基甲酰胺或二甲基亚砜,以及水。
适合的固体载体是:例如铵盐和磨碎的天然矿物质,如高岭土、粘土、滑石、白垩、石英、硅镁土、蒙脱石或硅藻土,和磨碎的合成矿物质,如高分散二氧化硅、矾土和硅酸盐,适合用于颗粒剂的固体载体有:例如压碎并分级的天然矿物质如方解石、大理石、浮石、海泡石和白云石,以及有机和无机粉的合成颗粒,和如下有机物的颗粒:锯木屑、椰壳、玉米穗轴和烟茎;适合的乳化剂和/或起泡剂是:例如非离子和阴离子乳化剂,如聚氧乙烯脂肪酸酯、聚氧乙烯脂肪醇醚,例如,烷芳基聚乙二醇醚,烷基磺酸盐,烷基硫酸盐,芳基磺酸盐以及白蛋白水解产物;适合的分散剂是:例如,木素亚硫酸废液和甲基纤维素。
制剂中可以使用粘合剂如羧甲基纤维素和粉状、颗粒或乳胶形式的天然和合成聚合物,如阿拉伯胶、聚乙烯醇和聚乙酸乙烯酯,以及天然磷脂,如脑磷脂和卵磷脂,和合成磷脂。其它的添加剂可以是矿物油和植物油。
也可能使用着色剂,如无机颜料,例如氧化铁、氧化钛和普鲁士蓝,和有机染料,如茜素染料、偶氮染料和金属酞菁染料,和微量营养元素如铁、锰、硼、铜、钴、钼和锌的盐。
制剂中通常含有按重量计0.1至95%的活性化合物,优选0.5至90%。
为防治杂草,本发明活性化合物,其原样或以其制剂形式,也可以作为与已知除草剂一起的混合物以终制剂或可能的桶混物使用。
混合物的可能的共组分是已知除草剂,例如,乙草胺、三氟羧草醚(钠盐)、苯草醚、甲草胺、禾草灭(钠盐)、莠灭净、amidochlor、酰嘧黄隆、莎稗磷、磺草灵、莠去津、azafenidin、四唑嘧黄隆、草除灵、呋草黄、苄嘧黄隆(甲酯)、灭草松、吡草酮、新燕灵(乙酯)、双丙氨酰磷、甲羧除草醚、双草醚、溴丁酰草胺、溴酚肟、溴苯腈、丁草胺、butroxydim、丁草特、cafenstrole、caloxydim、双酰草胺、carfentrazone(-methyl)、甲氧除草醚、灭草平、杀草敏、氯嘧黄隆(乙酯)、草枯醚、绿黄隆、绿麦隆、环庚草醚、醚黄隆、烯草酮、炔草酸、异噁草松、氯甲酰草胺、二氟吡啶酸、clopyrasulfuron(-methyl)、cloransulam(-methyl)、cumyluron、氰草津、灭草特、环丙嘧磺隆、噻草酮、氰氟草酯、2,4-滴、2,4-滴丁酸、2,4-滴丙酸、甜菜安、燕麦敌、麦草畏、禾草灵(甲酯)、diclosulam、乙酰甲草胺、野燕枯、双苯唑快、双氟酰草胺、diflufenzopyr、丁唑隆、哌草丹、二甲草胺、二甲丙乙净、二甲吩草胺、dimexyflam、氨氟灵、双苯酰草胺、敌草快、氟硫草定、敌草隆、杀草隆、茵达灭、禾草畏、乙丁烯氟灵、胺苯黄隆(甲酯)、乙呋草黄、ethoxyfen、ethoxysulfuron、etobenzanid、噁唑禾草灵乙酯、麦草伏(异丙酯)、麦草伏(异丙酯-L)、麦草伏(甲酯)、啶嘧黄隆、吡氟禾草灵(丁酯)、唑嘧磺草胺、氟烯草酸、丙炔氟草胺、flumipropyn、伏草隆、氟咯草隆、乙羧氟草醚(乙酯)、胺草唑、flupropacil、flurpyrsulfuron(-methyl、sodium)、芴丁酯、氟丁酮、氟草烟、调嘧醇、flurtamone、fluthiacet(-methyl)、fluthiamid、氟黄胺草醚、草铵磷(铵盐)、草甘磷(异丙铵盐)、halosafen、吡氟氯禾灵(乙氧基乙酯)、吡氟氯禾灵(-P-甲酯)、环嗪酮、咪草酯(甲酯)、imazamethapyr、imazamox、灭草烟、灭草喹、咪草烟、咪唑黄隆、碘苯腈、异丙乐灵、异丙隆、异噁隆、异噁酰草、isoxaflutole、噁草醚、乳氟禾草灵、环草定、利谷隆、2甲4氯、2甲4氯丙酸、苯噻草胺、苯嗪草酮、吡草胺、甲基苯噻隆、吡喃隆、秀谷隆、(α-)异丙甲草胺、磺草唑胺、甲氧隆、嗪草酮、甲黄隆(甲酯)、草达灭、绿谷隆、萘丙胺、萘氧丙草胺、草不隆、烟嘧黄隆、哒草伏、坪草丹、安磺灵、oxadiargyl、噁草酮、oxasulfuron、oxaziclomefone、乙氧氟草醚、百草枯、pelargonic acid、二甲戊乐灵、pentoxazone、甜菜宁、哌草磷、丙草胺、氟嘧黄隆(甲酯)、扑草净、毒草胺、敌稗、喔草酯、炔苯酰草胺、苄草丹、氟磺隆、pyraflufen(-ethyl)、吡唑特、吡嘧黄隆(乙酯)、苄草唑、pyribenzoxim、稗草丹、哒草特、pyriminobac(-methyl)、嘧草硫醚、二氯喹啉酸、喹草酸、灭草醌、喹禾灵(乙酯)、喹禾灵(四氢糠酯)、砜嘧黄隆、稀禾定、西玛津、西草净、sulcitrione、甲磺草胺、嘧黄隆(甲酯)、草硫磷、牧草胺、特丁噻草隆、特丁津、特丁净、噻吩草胺、噻呋酰胺、噻唑烟酸、thidiazimin、噻黄隆(甲酯)、杀草丹、仲草丹、肟草酮、野燕畏、醚苯黄隆、苯黄隆(甲酯)、绿草定、灭草环、氟乐灵和氟胺黄隆。
也可以是与其它已知活性化合物如杀真菌剂、杀虫剂、杀螨剂、杀线虫剂、驱鸟剂、植物养料和土壤结构改良剂一起的混合物。
活性化合物可以以其本身、以其制剂或由之经进一步稀释而制备的使用形式使用,如直接可用溶液、悬浮液、乳液、粉剂、膏剂和颗粒剂。它们以常规方法使用,例如浇泼、喷雾、弥雾或撒施等等。
本发明活性化合物可以在植物芽前或后施用。它们也可以在播种前掺入土壤中。
所用的活性化合物的量可以在相当宽的范围内变化。用量基本上取决于所需的效果。通常,使用量在每公顷土表面积用1克至10千克之间,优选每公顷5克至5千克。
本发明活性化合物的制备和使用可以参见下列实施例。
制备实施例:
在搅拌下,将4.5g(15mmol)氯甲酸[(3-三氟甲基-苯氧基甲基)-丙基]酯加入到3.1g(30mmol)N-氨基-吗啉和80ml甲苯的混合物中。反应混合物在室温(大约20℃)下搅拌5小时,之后用水洗涤,用硫酸钠干燥并过滤。将溶剂在水泵真空下仔细地从滤液中蒸馏掉。
由此作为固体残余物给出4.8g(理论值的88%)N-(4-吗啉基)-O-[(3-三氟甲基-苯氧基甲基)-丙基]-氨基甲酸乙酯,熔点98℃。
表1式(Ⅰ)化合物的实例 表1中给出的logP是通过HPLC,使用反相柱(C18),在EEC Directive79/831 Annex V.A8上测定的。测定温度43℃。(a)酸性范围中测定的移动相:0.1%磷酸水溶液、乙腈;10%乙腈
至90%乙腈线性梯度液-在表1中的相应数据标为a)。(b)中性范围中测定的移动相:0.01摩尔磷酸盐缓冲水溶液、乙腈;
10%乙腈至90%乙腈线性梯度液-在表1中的相应数据标为b)。
校对使用无支链烷-2-酮(具有3至16个碳原子)进行,所述的无支链烷-2-酮的logP值是已知的(使用线性内插法,通过介于二连续λ烷酮间的保留时间,确定其logP值)。
使用200nm至400nm的UV谱,以色谱信号的最高峰值确定λ最大值。
式(Ⅱ)起始原料:
将65g(0.50mol)丙酰基乙酸甲酯、34g(0.50mo1)乙醇钠和300ml1,4-二噁烷的混合物在80℃至90℃下搅拌30分钟,之后在室温(大约20℃)下,在搅拌下与97g(0.50mol)3-三氟甲基苄基氯混合。反应混合物在90℃至95℃下搅拌18小时,之后在水泵真空下浓缩。残余物在90℃下于400ml浓度20%氢氧化钠水溶液中搅拌4小时,之后用水稀释至其原体积的大约2倍,并用二氯甲烷振荡。分离出有机相,用水洗涤,用硫酸钠干燥并过滤。滤液在减压下蒸馏处理。
由此给出79.4g(理论值的69%)3-(3-三氟甲基-苯基)-丙酸乙酯,熔点75℃(0.7毫巴)。步骤2在室温(大约20℃下)和搅拌下将23g(0.10mol)3-(3-三氟甲基-苯基)-丙酸乙酯加入到6g硼氢化钠(60%浓度的石蜡液,0.20摩尔NaBH4)、100ml四氢呋喃和10ml水的混合物中,并将此混合物在室温下搅拌18小时。之后混合物用水洗涤至其原体积的大约三倍,并用二氯甲烷振荡,分离出有机相,用水洗涤,用硫酸钠干燥并过滤。滤液在减压下通过蒸馏处理。
由此给出18.2g(理论值的78%)1-(3-三氟甲基-苯基)-戊-3-醇,熔点78℃至80℃(0.6毫巴)。
将10g(43mmol)3,5-双三氟甲基-苯酚、5g(70mmol)乙基环氧乙烷和0.2g氢氧化锂的混合物加热回流5小时。之后在水泵真空下仔细蒸馏掉挥发性组分。
由此作为固体残余物给出12g(理论值的92%)1-(3,5-双三氟甲基-苯基)-丁-2-醇,熔点53℃。
类似于实施例(Ⅱ-1)和(Ⅱ-2),也可制备出例如下文表2中所列的式(Ⅱ)化合物
式(Ⅳ)起始原料:
在室温(大约20℃)下,将120g(0.52mol)1-(3-三氟甲基-苯基)-戊-3-醇在600ml甲苯中的溶液在搅拌下滴加入800ml甲苯、3ml N,N-二甲基-甲酰胺和54g(0.55mol)光气的混合物中。之后将反应混合物在60℃下搅拌8小时。随后在水泵真空下将溶剂仔细地蒸馏掉。
由此作为非晶型残余物给出144g(理论值的94%)O-[1-乙基-3-(3-三氟甲基-苯基)-丙基]氯甲酸酯,它可以无需纯化直接用作起始原料,用于本发明方法(b)。
应用实施例
实施例A
芽前试验
溶剂: 5份重量丙酮
乳化剂: 1份重量的烷芳基聚乙二醇醚
制备适合的活性化合物制剂时,将1份重量的活性化合物与所述量的溶剂混合,将所述量的乳化剂加入,并用水将此乳油稀释至所需浓度。
将试验植物的种子播入通常的土壤中,约24小时后,土壤用活性化合物制剂浇水。在每单位面积上最好保持常量。制备液中的活性化合物浓度并不重要,重要的是每单位面积上的活性化合物施用剂量。
三周后,将植物的损害程度与未处理对照的发育相比较,目测定出损害%。
数值的含义如下:
0%=无作用(与未处理相同)
100%=完全损害
在此试验中,例如,制备实施例1和40的化合物对杂草显示出强活性,且它们中的一些能被作物如大麦很好地耐受。
实施例B
芽后试验
溶剂: 5份重量丙酮
乳化剂: 1份重量的烷芳基聚乙二醇醚
制备适合的活性化合物制剂时,将1份重量的活性化合物与所述量的溶剂混合,将所述量的乳化剂加入,并用水将此乳油稀释至所需浓度。
向株高5-15厘米的试验植物按单位面积喷雾施用一定量的所需活性化合物制剂。选择喷雾液的浓度,使所需化合物的特定量以1,000升水/公顷的量施用。
三周后,将植物的损害程度与未处理对照相比较,定出损害%。
数值的含义如下:
0%=无作用(与未处理相同)
100%=完全破坏
在此试验中,例如,制备实施例1、2、33、34和40的化合物对杂草显示出强活性,且它们中的一些能被作物如小麦很好地耐受。
实施例C
大麦诱导抗性白粉病试验
溶剂: 48.8份重量N,N-二甲基甲酰胺
乳化剂: 1.2份重量的烷芳基聚乙二醇醚
制备适合的活性化合物制剂时,将1份重量的活性化合物与所述量的溶剂混合,将所述量的乳化剂加入,并用水将此乳油稀释至所需浓度。
为测试抗性诱导活性,将麦苗用所述施用剂量的活性化合物的制备液喷雾。处理4天后,将植物用白粉病菌大麦变种(Erysiphegraminis f.sp.hordei)的孢子接种。随后将植株置于相对湿度为70%,温度为18℃的温室中。
接种7天后进行评价。0%指效力相当于对照,而效力100%指未观察到有感染。
在此试验中,例如,制备实施例8、10、11、12、13、14、15、16和56的化合物在750g/ha的施用量下表现出80%至95%的防治效力。
实施例D
桃蚜试验
溶剂: 6份重量二甲基甲酰胺
67份重量的甲醇
乳化剂: 2份重量的烷芳基聚乙二醇醚
制备适合的活性化合物制剂时,将1份重量的活性化合物与所述量的溶剂混合,将所述量的乳化剂加入,并用水将此乳油稀释至所需浓度。
将已长有桃蚜(Myzus persicae)的蚕豆(Vicia faba minor)苗浸入所需浓度的活性化合物制备液中,并放置在塑料制的盒中。
在所需的一段时间后,测定死亡百分率。100%指蚜虫均被杀死;0%指没有蚜虫被杀死。
在此试验中,例如,制备实施例21、26、29和40的化合物在0.1%的活性化合物浓度下,表现出90%至100%的杀死率。
实施例E
小菜蛾试验/合成饲料
溶剂: 100份重量丙酮
乳化剂 1900份重量的甲醇
制备适合的活性化合物制剂时,将1份重量的活性化合物与所述量的溶剂混合,并将此乳油用甲醇稀释至所需浓度。
将所需浓度的活性化合物制备液的所述量用移液管移到标准量的合成饲料中。甲醇蒸发之后,在每一洞里放上大约有100粒小菜蛾卵的薄盒盖。将刚孵化的幼虫转移到处理的合成饲料上。
在所需的一段时间后,测定死亡百分率。100%指有的害虫均被杀死;0%指没有害虫被杀死。
在此试验中,例如,制备实施例22、23和69的化合物在0.1%的活性化合物浓度下,表现出95%的防治效力。
Claims (12)
2.根据权利要求1的取代的烷氧基羰基化合物,其特征在于,n 表示数字0或1,Ar 表示选自下列的均可任选被取代的单环或双环状的饱和或-如果适宜的话部分地-不饱和的碳环或杂环状基团:环戊基、环己基、苯基、萘基、四氢化萘基、十氢化萘基、呋喃基、苯并呋喃基、噻吩基、苯并噻吩基、噁唑基、苯并噁唑基、噻唑基、苯并噻唑基、吡唑基、吡啶基、喹啉基、异喹啉基、嘧啶基,或任选被取代的下列基团 其中A表示任选卤代的具有1至3个碳原子的烷二基,其中在每一种情况下可能的取代基优选选自下列:氰基、硝基、卤素、均可任选卤代的各具有至多6个碳原子的烷基、烷氧基、烷硫基、烷基亚磺酰基、烷基磺酰基、烷基羰基、烷氧基羰基;Q 表示O(氧)、S(硫)、SO、SO2、NH、N(C1-C4-烷基)或CH2(亚甲基);R1 表示具有1至6个碳原子的烷基或表示具有3至6个碳原子的环烷基;R2 表示氢或具有1至4个碳原子的烷基;Y 表示NH或N(C1-C4-烷基);和Z 表示均可任选被取代的氮杂环丙烷基、氮杂环丁烷基、吡咯烷基、哌啶基、吗啉基、硫代吗啉基、S-氧代-硫代吗啉基、S,S-二氧代-硫代吗啉基、全氢氮杂基、哌嗪基、吲哚基、异吲哚基、全氢吲哚基、全氢异吲哚基、四氢喹啉基、全氢喹啉基、四氢异喹啉基或全氢异喹啉基,它们均经N连接,或-如果n是1或Ar表示双环状基团的话-还表示均可任选被取代的具有3至6个碳原子的环烷基氨基或具有6或10个碳原子的芳基氨基,其中在每一种情况下可能的取代基优选选自下列:氰基、硝基、卤素、均可任选卤代的各具有至多6个碳原子的烷基、烷氧基、烷硫基、烷基亚磺酰基、烷基磺酰基、烷基羰基、烷氧基羰基。
3.根据权利要求1的取代的烷氧基羰基化合物,其特征在于,n 表示数字0或1,Ar 表示选自下列的均可任选被取代的单环状或双环状饱和的或-如果适宜的话部分地-不饱和的碳环状或杂环状基团:环己基、苯基、萘基、四氢化萘基、十氢化萘基、呋喃基、苯并呋喃基、噻吩基、苯并噻吩基、噁唑基、苯并噁唑基、噻唑基、苯并噻唑基、吡唑基、吡啶基、喹啉基、异喹啉基、嘧啶基,或同样任选被取代的下列基团
其中A表示任选由氟-和/或氯-取代的亚甲基或二亚甲基(乙-1,2-二基),其中在每一种情况下可能的取代基优选选自下列:氰基、硝基、氟、氯、溴、各任选由氟-和/或氯-取代的甲基、乙基、正或异丙基、正-、异-、仲-或叔丁基、甲氧基、乙氧基、正-或异丙氧基、正-、异-、仲-或叔丁氧基、甲硫基、乙硫基、正-或异丙硫基、正-、异-、仲-或叔丁硫基、甲基亚磺酰基、乙基亚磺酰基、正-或异丙基亚磺酰基、甲基磺酰基、乙基磺酰基、正-或异丙基磺酰基、乙酰基、丙酰基、正-或异丁酰基、甲氧基羰基、乙氧基羰基、正-或异丙氧基羰基;Q 表示O(氧)、S(硫)、SO、SO2、NH、N(甲基)或CH2(亚甲基);R1 表示甲基、乙基、正-或异丙基,或表示环丙基;R2 表示氢或甲基;Y 表示NH、N(甲基)、N(乙基)或N(异丙基);和Z 表示均可任选被取代的吡咯烷基、哌啶基、吗啉基、硫代吗啉基、S-氧代-硫代吗啉基、S,S-二氧代-硫代吗啉基、全氢氮杂基、哌嗪基、吲哚基、异吲哚基、全氢吲哚基、全氢异吲哚基、四氢喹啉基、全氢喹啉基、四氢异喹啉基或全氢异喹啉基,它们均经N连接,或-如果n是1或Ar表示双环状基团的话-还表示均可任选被取代的环己基氨基或苯基氨基,其中在每一种情况下可能的取代基优选选自下列:氰基、硝基、氯、氟、溴、均可任选由氟-和/氯取代的甲基、乙基、正或异丙基、正-、异-、仲-或叔丁基、甲氧基、乙氧基、正-或异丙氧基、正-、异-、仲-或叔丁氧基、甲硫基、乙硫基、正-或异丙硫基、正-、异-、仲-或叔丁硫基、甲基亚磺酰基、乙基亚磺酰基、正-或异丙基亚磺酰基、甲基磺酰基、乙基磺酰基、正-或异丙基磺酰基、乙酰基、丙酰基、正-或异丁酰基、甲氧基羰基、乙氧基羰基、正-或异丙氧基羰基。
4.根据权利要求3的取代的烷氧基羰基化合物,其特征在于,Ar表示下列基团其中R3表示氟、氯、溴、甲基、乙基、三氟甲基、甲氧基、二氟甲氧基或三氟甲氧基,和R4表示氢、氟、氯、甲基或三氟甲基;和R1表示甲基、乙基、正-或异丙基。
5.根据权利要求4的取代的烷氧基羰基化合物,其特征在于,Q 表示氧。
6.根据权利要求4的取代的烷氧基羰基化合物,其特征在于,Q 表示硫、SO或SO2。
7.根据权利要求4的取代的烷氧基羰基化合物,其特征在于,Q 表示NH或N(甲基)。
8.根据权利要求4的取代的烷氧基羰基化合物,其特征在于,Q 表示CH2(亚甲基)。
9.根据权利要求3的取代的烷氧基羰基化合物,其特征在于,
Ar表示下列基团之一Q 表示氧,R1 表示甲基、乙基或正-或异-丙基。
11.权利要求1至9之任一的至少一种取代的烷氧基羰基化合物作为除草剂、杀真菌剂和/或杀虫剂的应用。
12.作物保护组合物,其特征在于,它包含至少一种权利要求1至9之任一的烷氧基羰基化合物和常规扩充剂。
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US5194661A (en) * | 1990-08-20 | 1993-03-16 | Ici Americas Inc. | Substituted benzyl carbamates and their use as herbicides |
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