CN1110680A - 取代的1h-3-芳基-吡咯烷-2,4-二酮衍生物 - Google Patents
取代的1h-3-芳基-吡咯烷-2,4-二酮衍生物 Download PDFInfo
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- CN1110680A CN1110680A CN95101670A CN95101670A CN1110680A CN 1110680 A CN1110680 A CN 1110680A CN 95101670 A CN95101670 A CN 95101670A CN 95101670 A CN95101670 A CN 95101670A CN 1110680 A CN1110680 A CN 1110680A
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- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
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- 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
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- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
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- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- CHNQZRKUZPNOOH-UHFFFAOYSA-J zinc;manganese(2+);n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[Zn+2].[S-]C(=S)NCCNC([S-])=S.[S-]C(=S)NCCNC([S-])=S CHNQZRKUZPNOOH-UHFFFAOYSA-J 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
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Abstract
本发明涉及新的式(I)的1H-3-芳基-吡咯烷
-2,4-二酮衍生物、其多种制备方法、以及其作为杀
虫剂的用途,其中A、B、X、Y和G具有说明书中所
给出的意义。
Description
本发明涉及新的1H-3-芳基-吡咯烷-2,4-二酮衍生物、用于其制备的多种方法、以及它们作为杀虫剂,特别是作为杀昆虫剂、杀螨剂和除草剂的应用。
3-酰基-吡咯烷-2,4-二酮类化合物的药学性质先前已有过描述(S.Suzuki等人,Chem.Pharm.Bull.15 1120(1967))。此外,N-苯基吡咯烷-2,4-二酮类化合物由R.Schmierer和H.Mildenberger进行过合成(Liebigs Ann.Chem.1985 1095)。这些化合物的生物学活性未见描述。
EP-A-0 262 399和GB-2 266 888-A公开了类似结构的化合物(3-芳基-吡咯烷-2,4-二酮类化合物),但是并未公开除草活性、杀昆虫活性或杀螨活性。具有除草活性、杀昆虫活性或杀螨活性的已知物质是未取代的、二环的3-芳基-吡咯烷-2,4-二酮衍生物(EP-A-355 599和EP-415 211)和取代的单环的3-芳基-吡咯烷-2,4-二酮衍生物(EP-A-377 893和EP-442 077)。
此外,多环的3-芳基吡咯烷-2,4-二酮衍生物(EP-422 073)和1H-3-芳基吡咯烷-二酮衍生物(EP-456 063和EP-521 334)是已知的。
现已发现了新的式(Ⅰ)的取代的1H-3-芳基-吡咯烷-2,4-二酮衍生物,
其中
A代表氢、或烷基、链烯基、烷氧基烷基或烷硫基烷基,它们各自任选被卤素取代,或代表环烷基,该环烷基任选被至少一个杂原子所间断并任选被取代,
或代表芳基、芳烷基或杂芳基,它们各自任选被卤素、烷基、卤代烷基、烷氧基或硝基所取代;
B代表氢、烷基或烷氧基烷基;或
A和B与它们所键合的碳原子一起代表饱和或不饱和的、未取代的或取代的环,该环任选被至少一个杂原子所间断;
X代表卤素或烷基;
Y代表卤素或烷基;
G代表氢(a)或下列基团之一:
E代表金属离子等同物(metal ion equivalent)或铵离子;
L和M在每种情况下代表氧或硫;
R1代表烷基、链烯基、烷氧基烷基、烷硫基烷基或多烷氧基烷基(polyalkoxyalkyl),它们各自任选被卤素所取代,或代表环烷基,该环烷基任选被卤素或烷基所取代并可被至少一个杂原子所间断,或
在每种情况下代表任选取代的苯基、苯基烷基、杂芳基、苯氧基烷基或杂芳基氧基烷基;
R2代表烷基、链烯基、烷氧基烷基或多烷氧基烷基(polyalkoxyalkyl),它们各自任选被卤素所取代,或
在每种情况下代表任选取代的环烷基、苯基或苄基;
R3、R4和R5彼此独立地代表烷基、烷氧基、烷氨基、二烷基氨基、烷硫基、链烯基硫基或环烷基硫基,它们各自任选被卤素所取代,或
在每种情况下代表任选取代的苯基、苯氧基或苯硫基;
R6和R7彼此独立地代表氢、或烷基、环烷基、链烯基、烷氧基或烷氧基烷基,它们各自任选被卤素所取代,或
在每种情况下代表任选取代的苯基或苄基,或
与它们所键合的N原子一起代表环,该环任选被氧或硫所间断;
条件是:X和Y不同时代表烷基并且不同时代表卤素。
考虑到基团G的各种含义(a)、(b)、(c)、(d)、(e)、(f)和(g),得到下列主结构(Ⅰa)至(Ⅰg):
其中
A、B、E、L、M、X、Y、R1、R2、R3、R4、R5、R6和R7具有上述意义。
由于存在一个或多个手性中心,式(Ⅰa)-(Ⅰg)化合物一般可以立体异构体的混合物的形式获得,如果需要,这些立体异构体可以习用方式分离。这些化合物可以其非对映体的混合物形式使用,并且还可以纯的非对映体或对映体的形式使用。为简单起见,下文将始终提及式(Ⅰa)至(Ⅰg)化合物,尽管这应被理解为代表纯化合物以及包含各种含量的异构化合物、对映体化合物和立体异构化合物的混合物的含义。
此外,已发现新的式(Ⅰ)的取代的1H-3-芳基-吡咯烷-2,4-二酮衍生物是通过下述方法之一获得的。
(A)式(Ⅰa)的1H-3-芳基-吡咯烷-2,4-二酮类化合物或它们的烯醇类化合物可这样制得:
其中:
A、B、X和Y具有上述意义,
即在稀释剂和在碱的存在下,使式(Ⅱ)的N-酰基氨基酸酯类进行分子内缩合反应,
其中:
A、B、X和Y具有上述意义,和
R8代表烷基,特别是C1-C10烷基;或者
(B)式(Ⅰb)化合物可如下制得:
其中:
A、B、X、Y和R1具有上述意义,
即使式(Ⅰa)化合物
其中:
A、B、X和Y具有上述意义,
α)与式(Ⅲ)的酰基卤类化合物反应,
其中:
R1具有上述意义,和
Hal 代表卤素,特别是氯或溴,
如果必要在稀释剂的存在下进行,以及如果必要,在酸结合剂的存在下进行,或
β)与式(Ⅳ)的羧酸酐类化合物反应:
其中:
R1具有上述意义,
如果必要在稀释剂的存在下进行,以及如果必要在酸结合剂的存在下进行;或者
(C)式(Ⅰc-a)化合物可如下制得:
其中:
A、B、X、Y和R2具有上述意义,和
M代表氧或硫,
即使式(Ⅰa)化合物与式(Ⅴ)的氯甲酸酯类或氯甲酸硫酯类化合物反应,
其中:
A、B、X和Y具有上述意义,
其中:
R2和M具有上述意义,
如果必要在稀释剂存在下反应,以及如果必要在酸结合剂的存在下进行;或者
(D)式(Ⅰc-b)化合物可如下制得:
其中:
A、B、R2、X和Y具有上述意义,和
M代表氧或硫,
即使式(Ⅰa)化合物
其中:
A、B、X和Y具有上述意义
α)与式(Ⅵ)的氯代一硫代甲酸酯类或氯代二硫代甲酸酯类似合物反应,
其中:
M和R2具有上述意义,
如果必要在稀释剂存在下反应,并且如果必要在酸结合剂存在下反应,或者
β)与二硫化碳反应,并随后与式(Ⅶ)的烷基卤类化合物反应,
其中:
R2具有上述意义,和
Hal代表氯、溴或碘;
或者
(E)式(Ⅰd)化合物可如下制得:
其中:
A、B、X、Y和R3具有上述意义,
即使式(Ⅰa)化合物与式(Ⅷ)的磺酰氯类化合物反应,
其中:
A、B、X和Y具有上述意义,
其中:
R3具有上述意义,
如果必要在稀释剂的存在下进行,并且如果必要在酸结合剂的存在下进行;或者
(F)式(Ⅰe)的3-芳基-吡咯烷-2,4-二酮类化合物可如下制得:
其中:
A、B、L、X、Y、R4和R5具有上述意义,
即使式(Ⅰa)的1H-3-芳基吡咯烷-2,4-二酮类化合物或其烯醇类化合物与式(Ⅸ)的磷化合物反应,
其中:
A、B、X和Y具有上述意义,
其中:
L、R4和R5具有上述意义,和
Hal代表卤素,特别是氯或溴,
如果必要在稀释剂的存在下进行,并且如果必要在酸结合剂的存在下进行,或者
(G)式(Ⅰf)化合物可如下制得:
其中:
A、B、X和Y具有上述意义,和
E代表金属离子等同物(metal ion equivalent)或铵离子,即使式(Ⅰa)化合物与式(Ⅹ)和(Ⅺ)的金属氢氧化物、金属醇盐或胺反应,
其中:
A、B、X和Y具有上述意义,
其中:
Me代表一价或二价的金属,例如锂、钾、钠、钙或镁;
t代表数字1或2;和
R10、R11和R12彼此独立地代表氢和/或烷基,
如果必要在稀释剂的存在下进行。
(H)此外,已发现式(Ⅰg)化合物可如下制得:
其中:
A、B、L、X、Y、R6和R7具有上述意义,即使式(Ⅰa)化合物
其中:
A、B、X和Y具有上述意义,
α)与式(Ⅻ)的异氰酸酯类或异硫氰酸酯类化合物反应,
其中:
L和R6具有上述意义,
如果必要,在稀释剂存在下进行,并且如果必要在催化剂存在下进行,或者
β)与式(ⅩⅢ)的氨基甲酰氯类或硫代氨基甲酰氯类化合物反应,
其中:
L、R6和R7具有上述意义,
如果必要在稀释剂存在下进行,并且如果必要在酸结合剂存在下进行。
此外,已发现新的式(Ⅰ)的1H-3-芳基吡咯烷-2,4-二酮衍生物具有显著的杀虫、杀螨和除草活性。
下列化合物适用于本申请的通式中:
A优选代表氢、或C1-C12烷基、C3-C8链烯基、C1-C10烷氧基-C1-C8烷基、C1-C8-多烷氧基(polyalkoxy)-C1-C8烷基或C1-C10烷硫基-C1-C6烷基,它们各自任选被卤素取代,或代表具有3-8个环原子的环烷基,该环烷基任选被卤素、C1-C4烷基或C1-C4烷氧基取代,并可被氧和/或硫间断,或代表芳基、5~6元杂芳基或芳基-C1-C6烷基,它们各自任选被卤素、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基和/或硝基取代,
B优选代表氢、C1-C12烷基或C1-C8烷氧基烷基,或
A、B和它们所键合的碳原子优选代表饱和或不饱和的C3-C10螺环,该螺环任选被氧或硫间断,并任选被C1-C10烷基、C3-C10环烷基、C1-C6卤代烷基、C1-C10烷氧基、C1-C10烷硫基、卤素或苯基一取代或多取代,或者
A、B和它们所键合的碳原子优选代表C3-C6螺环,该螺环可被任选被一个或两个氧和/或硫原子所间断的亚烷二基取代,或可被亚烷二氧基或被亚烷二硫基取代,该亚烷二基、亚烷二氧基或亚烷二硫基与它们所键合的碳原子一起形成另一个五至八元螺环,或者
A、B和它们所键合的碳原子代表C3-C8螺环,其中两个取代基一起代表饱和的或不饱和的3~8元环,所述环任选被C1-C6烷基、C1-C6烷氧基或卤素取代,并可被氧或硫间断。
A特别优选代表氢、或C1-C10烷基、C3-C6链烯基、C1-C8烷氧基-C1-C6烷基、C1-C6多烷氧基(polyalkoxy)-C1-C6烷基或C1-C8烷硫基-C1-C6烷基,它们各自任选被氟和/或氯取代,或代表具有3~7个环原子的环烷基,该环烷基任选被氟、氯、C1-C3烷基或C1-C3烷氧基取代并可被1或2个氧和/或硫原子间断,
或代表苯基、呋喃基、吡啶基、咪唑基、三唑基、吡唑基、吲哚基、噻唑基、噻吩基或苯基-C1-C4烷基,它们各自被氟、氯、溴、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基和/或硝基任选取代。
B特别优选代表氢、C1-C10烷基或C1-C6烷氧基烷基,或
A、B和它们所键合的碳原子特别优选代表饱和的或不饱和的C3-C9螺环,该螺环任选被氧或硫间断并任选被C1-C6烷基、C3-C8环烷基、C1-C3卤代烷基、C1-C6烷氧基、C1-C6烷硫基、氟、氯或苯基一取代或多取代,或者
A、B和它们所键合的碳原子特别优选代表C3-C6螺环,该螺环可被任选被一个或两个氧或硫原子间断的亚烷二基取代或可被亚烷二氧基或被亚烷二硫基取代,该亚烷二基、亚烷二氧基或亚烷二硫基与它们所键合的碳原子一起形成另一个5~7元螺环,或者
A、B和它们所键合的碳原子特别优选代表C3-C6螺环,其中两个取代基一起代表饱和或不饱和的5-8元环,所述环任选被C1-C3烷基、C1-C3烷氧基、氟、氯或溴取代,并可被氧或硫间断。
A非常特别优选代表氢、或C1-C8烷基、C3-C4链烯基、C1-C6烷氧基-C1-C4烷基、C1-C4多烷氧基(polyalkoxy)-C1-C4烷基、或C1-C6烷硫基-C1-C4烷基,它们各自任选被氟和/或氯取代,或代表具有3-6个环原子的环烷基,该环烷基任选被氟、氯、甲基、乙基、甲氧基或乙氧基取代,并可被1或2个氧和/或硫原子间断,
或代表苯基、呋喃基、吡啶基、咪唑基、吡唑基、三唑基、吲哚基、噻唑基、噻吩基或苄基,它们各自任选被氟、氯、溴、甲基、乙基、丙基、异丙基、甲氧基、乙氧基、三氟甲基和/或硝基取代。
B非常特别优选代表氢、C1-C8烷基或C1-C4烷氧基烷基,或
A、B和它们所键合的碳原子非常特别优选代表饱和的或不饱和的C3-C8螺环,该螺环任选被氧或硫间断,并任选被下列基团一取代或多取代:甲基、乙基、丙基、异丙基、丁基、异丁基、仲丁基、叔丁基、环己基、三氟甲基、甲氧基、乙氧基、丙氧基、异丙氧基、丁氧基、异丁氧基、仲丁氧基、叔丁氧基、甲硫基、乙硫基、氟、氯或苯基,或
A、B和它们所键合的碳原子非常特别优选代表C3-C6螺环,该螺环可被任选被氧或硫原子间断的亚烷二基取代,或可被亚烷二氧基取代,该亚烷二基或亚烷二氧基与它们所键合的碳原子一起形成另一个5~7元螺环,或者
A、B和它们所键合的碳原子非常特别优选代表C3-C6螺环,其中两个取代基一起代表饱和的或不饱和的5或6元环,该环可被氧或硫间断。
X优选代表卤素或C1-C6烷基。
X特别优选代表氟、氯、溴或C1-C4烷基。
X非常特别优选代表氯、溴、甲基、乙基、丙基、或异丙基。
Y优选代表卤素或C1-C6烷基。
Y特别优选代表氟、氯、溴或C1-C4烷基。
Y非常特别优选代表氯、溴、甲基、乙基、丙基、或异丙基。
在这些化学式中,X和Y不同时代表烷基且不同时代表卤素。
G优选代表氢(a)或下列基团之一:
其中:
E代表金属离子等同物(metal ion equivalent)或铵离子,和
L和M在每种情况下代表氧或硫。
R1优选代表C1-C20烷基、C2-C20链烯基、C1-C8烷氧基-C1-C8烷基、C1-C8烷硫基-C1-C8烷基或C1-C8多烷氧基(polyalkoxy)-C1-C8烷基,它们各自任选被卤素取代,或代表具有3-8个环原子的环烷基,该环烷基任选被卤素或C1-C6烷基取代并可被至少一个氧和/或硫原子间断,或代表苯基,它任选被卤素、硝基、C1-C6烷基、C1-C6烷氧基、C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6烷硫基或C1-C6烷基磺酰基取代,
或代表苯基-C1-C6烷基,它任选被卤素、C1-C6烷基、C1-C6烷氧基、C1-C6卤代烷基或C1-C6卤代烷氧基取代,
或代表5或6元杂芳基,它任选被卤素和/或C1-C6烷基取代,或代表苯氧基-C1-C6烷基,它任选被卤素和/或C1-C6烷基取代,
或代表5或6元杂芳氧基-C1-C6烷基,它任选被卤素、氨基和/或C1-C6烷基取代。
R2优选代表C1-C20烷基、C3-C20链烯基、C1-C8烷氧基-C1-C8烷基或C1-C8多烷氧基(polyalkoxy)-C1-C8烷基,它们各自任选被卤素取代,
或代表C3-C8环烷基,它任选被卤素、C1-C4烷基和/或C1-C4烷氧基取代,
或代表苯基或苄基,它们各自任选被卤素、硝基、C1-C6烷基、C1-C6烷氧基和/或C1-C6卤代烷基取代。
R3、R4和R5彼此独立地优选代表C1-C8烷基、C1-C8烷氧基、C1-C8烷氨基、二(C1-C8)烷氨基、C1-C8烷硫基、C2-C8链烯基硫基或C3-C7环烷基硫基,它们各自任选被卤素取代,
或代表苯基、苯氧基或苯硫基,它们各自任选被下列基团取代:卤素、硝基、氰基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4卤代烷硫基、C1-C4烷基或C1-C4卤代烷基。
R6和R7彼此独立地优选代表氢、或代表C1-C8烷基、C3-C8环烷基、C1-C8烷氧基、C3-C8链烯基或C1-C8烷氧基-C1-C8烷基,它们各自任选被卤素取代,
或代表苯基,它任选被卤素、C1-C8卤代烷基、C1-C8烷基和/或C1-C8烷氧基取代,
或代表苄基,它任选被卤素、C1-C8烷基、C1-C8卤代烷基和/或C1-C8烷氧基取代,
或一起代表C3-C6亚烷基环,它任选被氧或硫间断。
G特别优选代表氢(a)或下列基团之一:
其中:
E代表金属离子等同物(metal ion equivalent)或铵离子,
L和M在每种情况下代表氧或硫。
R1特别优选代表C1-C16烷基、C2-C16链烯基、C1-C6烷氧基-C1-C6烷基、C1-C16烷硫基-C1-C6烷基或C1-C6多烷氧基(polyalkoxy)-C1-C6烷基,它们各自任选被氟和/或氯取代,或代表具有3-7个环原子的环烷基,该环烷基任选被卤素或C1-C5烷基取代,并可被1或2个氧和/或硫原子间断,
或代表苯基,它任选被下列基团取代:卤素、硝基、C1-C4烷基、C1-C4烷氧基、C1-C3卤代烷基、C1-C3卤代烷氧基、C1-C4烷硫基或C1-C4烷基磺酰基,
或代表苯基-C1-C4烷基,它任选被卤素、C1-C4烷基、C1-C4烷氧基、C1-C3卤代烷基或C1-C3卤代烷氧基取代,
或代表吡唑基、噻唑基、吡啶基、嘧啶基、呋喃基或噻吩基,它们各自任选被氟、氯、溴和/或C1-C4烷基取代,
或代表苯氧基-C1-C5烷基,它任选被氟、氯、溴和/或C1-C4烷基取代,
或代表吡啶氧基-C1-C5烷基、嘧啶氧基-C1-C5烷基或噻唑氧基-C1-C5烷基,它们各自任选被氟、氯、溴、氨基和/或C1-C4烷基取代。
R2特别优选代表C1-16烷基、C3-C16链烯基、C1-C6烷氧基-C1-C6烷基或C1-C6多烷氧基(polyalkoxy)-C1-C6烷基,它们各自任选被卤素取代,
或代表C3-C7环烷基,它任选被卤素、C1-C3烷基和/或C1-C3烷氧基取代,
或代表苯基或苄基,它们各自任选被卤素、硝基、C1-C4烷基、C1-C3烷氧基和/或C1-C3卤代烷基取代。
R3、R4和R5彼此独立地特别优选代表C1-C6烷基、C1-C6烷氧基、C1-C6烷氨基、二(C1-C6)烷基氨基、C1-C6烷硫基、C3-C4链烯基硫基或C3-C6环烷基硫基,它们各自任选被卤素取代,
或代表苯基、苯氧基或苯硫基,它们各自任选被下列基团取代:氟、氯、溴、硝基、氰基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3卤代烷硫基、C1-C3烷基或C1-C3卤代烷基。
R6和R7彼此独立地特别优选代表氢、或代表C1-C6烷基、C3-C6环烷基、C1-C6烷氧基、C3-C6链烯基或C1-C6烷氧基-C1-C6烷基,它们各自任选被卤素取代,
或代表苯基,它任选被卤素、C1-C5卤代烷基、C1-C5烷基和/或C1-C5烷氧基取代,
或代表苄基,它任选被卤素、C1-C5烷基、C1-C5卤代烷基和/或C1-C5烷氧基取代,
或一起代表C3-C6亚烷基环,它任选被氧或硫间断。
G非常特别优选代表氢(a)或下列基团之一:
其中:
E代表金属离子等同物(metal ion equivalent)或铵离子,和
L和M在每种情况下代表氧或硫。
R1非常特别优选代表C1-C14烷基、C2-C14链烯基、C1-C4烷氧基-C1-C5烷基、C1-C4烷硫基-C1-C6烷基或C1-C4多烷氧基(polyalkoxy)-C1-C4烷基,它们各自任选被氟和/或氯取代,或代表具有3-6个环原子的环烷基,它任选被氟、氯、甲基、乙基、丙基、异丙基、丁基、异丁基或叔丁基取代,并可被1或2个氧和/或硫原子间断,
或代表苯基,它任选被氟、氯、溴、硝基、甲基、乙基、丙基、异丙基、甲氧基、乙氧基、三氟甲基、三氟甲氧基、甲硫基、乙硫基、甲磺酰基、或乙磺酰基取代,
或代表苯基-C1-C3烷基,它任选被氟、氯、溴、甲基、乙基、丙基、异丙基、甲氧基、乙氧基、三氟甲基或三氟甲氧基取代,或代表呋喃基、噻吩基、吡啶基、嘧啶基、噻唑基或吡唑基,它们各自任选被氟、氯、溴、甲基或乙基取代,
或代表苯氧基-C1-C4烷基,它们各自任选被氟、氯、甲基和/或乙基取代,
或代表吡啶氧基-C1-C4烷基、嘧啶氧基-C1-C4烷基或噻唑氧基-C1-C4烷基,它们各自任选被氟、氯、氨基、甲基或乙基取代。
R2非常特别优选代表C1-14烷基、C3-C14链烯基、C1-C4烷氧基-C1-C6烷基或C1-C4多烷氧基(polyalkoxy)-C1-C6烷基,它们各自任选被氟和/或氯取代,或代表C3-C6环烷基,它任选被氟、氯、甲基、乙基、丙基、异丙基、或甲氧基取代。
或代表苯基或苄基,它们各自任选被氟、氯、硝基、甲基、乙基、丙基、异丙基、甲氧基、乙氧基或三氟甲基取代。
R3、R4和R5彼此独立地非常特别优选代表C1-C4烷基、C1-C4烷氧基、C1-C4烷氨基、二(C1-C4)烷基氨基、或C1-C4烷硫基,它们各自任选被氟和/或氯取代,
或代表苯基、苯氧基或苯硫基,它们各自任选被氟、氯、溴、硝基、氰基、C1-C2烷氧基、C1-C2氟代烷氧基、C1-C2烷硫基、C1-C2氟代烷硫基或C1-C3烷基取代。
R6和R7彼此独立地非常特别优选代表氢、或代表C1-C4烷基、C3-C6环烷基、C1-C4烷氧基、C3-C4链烯基或C1-C4烷氧基-C1-C4烷基,它们各自任选被氟、氯、溴取代,或代表苯基,它任选被氟、氯、溴、C1-C4卤代烷基、C1-C4烷基和/或C1-C4烷氧基取代,
或代表苄基,它任选被氟、氯、溴、C1-C4烷基、C1-C4卤代烷基和/或C1-C4烷氧基取代,
或一起代表C4-C6亚烷基环,它任选被氧或硫间断。
上述定义中,饱和的或不饱和的烷基,也包括与杂原子相连接的烷基,例如烷氧基或烷硫基,如果可能,在各种情况下可以是直链或支链的。
在一般的或在优选范围内所提及的基团或说明的上述定义,若需要可以彼此结合起来,也就是说,在各个范围和优选范围之间的结合也是可能的。它们适用于最终产物并类似地适用于前体和中间体。
根据本发明优选的是那些其中存在上述作为优选定义的结合的通式(Ⅰ)化合物。
根据本发明特别优选的是那些其中存在上述作为特别优选定义的结合的通式(Ⅰ)化合物。
根据本发明非常特别优选的是那些其中存在上述作为非常特别优选定义的结合的通式(Ⅰ)化合物。
除了在制备例中所提及的化合物外,还可单独提及下列式(Ia)化合物:
表1:
表1,续
表1,续
表1,续
表1,续
表1,续
表1,续
除了在制备例中所提及的化合物以外,还可单独提及下列式(Ⅰb)化合物:
表2:
表2,续
表2,续
表2,续
表2,续
表2,续
表2,续
表2,续
表2,续
表2,续
表2,续
除了在制备例中所提及的化合物以外,还可单独提及下列式(Ⅰc)化合物:
表3:
表3,续
表3,续
表3,续
表3,续
表3,续
表3,续
表3,续
表3,续
表3,续
表3,续
表3,续
表3,续
表3,续
表3,续
表3,续
表3,续3,续
除了在制备例中所提及的化合物以外,还可单独提及下列式(Ⅰd)化合物:
表4:
表4,续
表4,续
表4,续
除了在制备例中所提及的化合物以外,还可单独提及下列式(Ⅰe)化合物:
表5:
表5,续
表5,续
表5,续
表5,续
表5,续
表5,续
表5,续
表5,续
表5,续
表5,续
表5,续
表5,续
表5,续
表5,续
表5,续
表5,续
除了在制备例中所提及的化合物以外,还可单独提及下列式(Ⅰf-a)化合物:
表6a:
表6a,续
表6a,续
表6a,续
除了在制备例中所提及的化合物以外,还可单独提及下列式(Ⅰf-b)化合物:
表6b:
表6b,续
表6b,续
表6b,续
除了在制备例中所提及的化合物以外,还可单独提及下列式(Ⅰg-a)化合物:
表7a
表7a,续
表7a,续
表7a,续
除了在制备例中所提及的化合物以外,还可单独提及下列式(Ⅰg-b)化合物:
表7b:
表7b,续
表7b,续
表7b,续
表7b,续
表7b,续
若按照方法(A),将N-(2-氯-4-甲基苯基乙酰基)-1-氨基-4-乙基-环己烷羧酸乙酯用作起始物质,则本发明方法的流程可用下列方程式表示:
若按照方法(Bα),将3-(2-甲基-4-氯苯基)-5,5-二甲基-吡咯烷-2,4-二酮和新戊酰氯用作起始物质,则本发明方法的流程可用下列方程式表示:
若按照方法(Bβ),将3-(2-溴-4-乙基苯基)-5-异丙基-5-甲基-吡咯烷-2,4-二酮和乙酐用作起始化合物,则本发明方法的流程可用下列方程式表示:
若按照方法(C),将3-(2-甲基-4-氯苯基)-5,5-二乙基-吡咯烷-2,4-二酮和氯甲酸乙氧基乙基酯用作起始化合物,则本发明方法的流程可用下列方程式表示:
若按照方法(Dα),将3-(2-氯-4-甲基苯基)-5,5-亚戊基-吡咯烷-2,4-二酮和氯代一硫代甲酸甲酯用作起始原料,则反应过程可表示如下:
若按照方法(Dβ),将3-(2-溴-4-乙基苯基)-5,5-(2,2′-乙硫醚基(ethylmercaptoethyl))-吡咯烷-2,4-二酮、二硫化碳和碘甲烷用作起始原料,则反应过程可表示如下:
若按照方法(E),将3-(2-氯-4-异丙基苯基)-5,5-(2-甲基)-亚戊基-吡咯烷-2,4-二酮和甲磺酰氯用作起始物质,则反应过程可用下列方程式表示:
若按照方法(F),将3-(2-甲基-4-氯苯基)-5-异丁基-5-甲基-吡咯烷-2,4-二酮和甲基硫代膦酸2,2,2-三氟乙基酯用作起始物质,则反应过程可用下列方程式表示:
若按照方法(G),将3-(2-氟-4-甲基苯基)-5-环丙基-5-甲基-吡咯烷-2,4-二酮和NaOH用作反应物,则本发明方法的过程可用下列方程式表示:
若按照方法(Hα),将3-(2-氯-4-乙基苯基)-5,5-亚己基-吡咯烷-2,4-二酮和异氰酸乙酯用作起始物质,则反应过程可用下列方程式表示:
若按照方法(Hβ),将3-(2-甲基-4-氯苯基)-5-甲基-吡咯烷-2,4-二酮和二甲基氨基甲酰氯用作起始原料,则反应过程可用下列方程式表示:
在本发明方法(A)中作为起始物质所需的式(Ⅱ)化合物是新的:
其中
A、B、X、Y和R8具有上述意义。
式(Ⅱ)的酰基-氨基酸酯类可如下制得,例如将式(ⅩⅣ)的氨基酸衍生物用式(ⅩⅤ)的苯乙酰卤酰化(Chem.Reviews 52,237-416(1953):Bhattacharya,Indian J. Chem. 6,341-5, 1968),
其中:
R9代表氢(ⅩⅣa)或烷基,优选C1-C6烷基(ⅩⅣb),和
A和B具有上述意义,
其中:
X和Y具有上述意义,和
Hal 代表氯或溴,
并酯化所得到的R9为氢的式(Ⅱa)的酰基氨基酸类(Chem. Ind.(London)1568(1968)),
其中:
A、B、X和Y具有上述意义。
式(ⅩⅣa)的取代的环状氨基羧酸类化合物一般可通过Bucherer-Bergs合成法或通过Strecker合成法获得,并且在每一情况下以各种异构形式得到。Bucherer-Bergs合成法的条件例如主要形成其中基团R和羧基在平伏位置的异构体(为简单起见,下文称为β);而Strecker合成法的条件主要形成其中氨基和基团R在平伏位置的异构体(为简单起见,下文称为α)。
(L.Munday,J.Chem.Soc.4372(1961);J.T.Eward,C.Jitrangeri,Can.J.Chem.53,3339(1975).
此外,在上面方法(A)中所用的式(Ⅱ)的起始物质可制备如下:
其中:
A、B、X、Y和R8具有上述意义,
通过使式(ⅩⅥ)的氨基腈类化合物与式(ⅩⅤ)的苯乙酰卤反应,生成式(ⅩⅦ)化合物,
其中:
A和B具有上述意义,
其中:
X和Y具有上述意义,和
Hal代表氯或溴,
其中:
A、B、X和Y具有上述意义,并将其随后在硫酸存在下进行醇解反应。
式(ⅩⅦ)化合物也是新的。
除了在制备例中所述中间体外,还可通过举例方式,而非以限制的方式提及下列式(Ⅱ)化合物:
N-(2-氯-4-甲基苯乙酰基)丙氨酸甲酯,
N-(2-氯-4-甲基苯乙酰基)亮氨酸甲酯,
N-(2-氯-4-甲基苯乙酰基)异亮氨酸甲酯,
N-(2-氯-4-甲基苯乙酰基)缬氨酸甲酯,
N-(2-氯-4-甲基苯乙酰基)氨基异丁酸甲酯,
N-(2-氯-4-甲基苯乙酰基)-2-乙基-2-氨基丁酸甲酯,
N-(2-氯-4-甲基苯乙酰基)-2-甲基-2-氨基戊酸甲酯,
N-(2-氯-4-甲基苯乙酰基)-2,3-二甲基-2-氨基戊酸甲酯,
N-(2-氯-4-甲基苯乙酰基)-1-氨基-环戊烷羧酸甲酯,
N-(2-氯-4-甲基苯乙酰基)-1-氨基-环己烷羧酸甲酯,
N-(2-氯-4-甲基苯乙酰基)-1-氨基-环庚烷羧酸甲酯,
N-(2-氯-4-甲基苯乙酰基)-1-氨基-环辛烷羧酸甲酯,
N-(4-氯-2-甲基苯乙酰基)丙氨酸甲酯,
N-(4-氯-2-甲基苯乙酰基)亮氨酸甲酯,
N-(4-氯-2-甲基苯乙酰基)异亮氨酸甲酯,
N-(4-氯-2-甲基苯乙酰基)缬氨酸甲酯,
N-(4-氯-2-甲基苯乙酰基)氨基异丁酸甲酯,
N-(4-氯-2-甲基苯乙酰基)-2-乙基-2-氨基丁酸甲酯,
N-(4-氯-2-甲基苯乙酰基)-2-甲基-2-氨基戊酸甲酯,
N-(4-氯-2-甲基苯乙酰基)-2,3-二甲基-2-氨基戊酸甲酯,
N-(4-氯-2-甲基苯乙酰基)-1-氨基-环戊烷羧酸甲酯,
N-(4-氯-2-甲基苯乙酰基)-1-氨基-环己烷羧酸甲酯,
N-(4-氯-2-甲基苯乙酰基)-1-氨基-环庚烷羧酸甲酯,
N-(4-氯-2-甲基苯乙酰基)-1-氨基-环辛烷羧酸甲酯,
N-(2-氯-4-甲基苯乙酰基)-1-氨基-2-甲基-环己烷羧酸甲酯,
N-(2-氯-4-甲基苯乙酰基)-1-氨基-3-甲基-环己烷羧酸甲酯,
N-(2-氯-4-甲基苯乙酰基)-1-氨基-4-甲基-环己烷羧酸甲酯,
N-(2-氯-4-甲基苯乙酰基)-1-氨基-3,4-二甲基-环己烷羧酸甲酯,
N-(2-氯-4-甲基苯乙酰基)-1-氨基-4-乙基-环己烷羧酸甲酯,
N-(2-氯-4-甲基苯乙酰基)-1-氨基-4-异丙基-环己烷羧酸甲酯,
N-(2-氯-4-甲基苯乙酰基)-1-氨基-4-叔丁基-环己烷羧酸甲酯,
N-(2-氯-4-甲基苯乙酰基)-1-氨基-4-甲氧基-环己烷羧酸甲酯,
N-(4-氯-2-甲基苯乙酰基)-1-氨基-2-甲基-环己烷羧酸甲酯,
N-(4-氯-2-甲基苯乙酰基)-1-氨基-3-甲基-环己烷羧酸甲酯,
N-(4-氯-2-甲基苯乙酰基)-1-氨基-4-甲基-环己烷羧酸甲酯,
N-(4-氯-2-甲基苯乙酰基)-1-氨基-3,4-二甲基-环己烷羧酸甲酯,
N-(4-氯-2-甲基苯乙酰基)-1-氨基-4-乙基-环己烷羧酸甲酯,
N-(4-氯-2-甲基苯乙酰基)-1-氨基-4-异丙基-环己烷羧酸甲酯,
N-(4-氯-2-甲基苯乙酰基)-1-氨基-4-叔丁基-环己烷羧酸甲酯,
N-(4-氯-2-甲基苯乙酰基)-1-氨基-4-甲氧基-环己烷羧酸甲酯。
除了在制备例中所提及的中间体外,还可通过举例方式而非以限制的方式提及下列式(Ⅱa)化合物:
N-(2-氯-4-甲基苯乙酰基)丙氨酸,
N-(2-氯-4-甲基苯乙酰基)亮氨酸,
N-(2-氯-4-甲基苯乙酰基)异亮氨酸,
N-(2-氯-4-甲基苯乙酰基)缬氨酸,
N-(2-氯-4-甲基苯乙酰基)氨基异丁酸,
N-(2-氯-4-甲基苯乙酰基)-2-乙基-2-氨基丁酸,
N-(2-氯-4-甲基苯乙酰基)-2-甲基-2-氨基戊酸,
N-(2-氯-4-甲基苯乙酰基)-2,3-二甲基-2-氨基戊酸,
N-(2-氯-4-甲基苯乙酰基)-1-氨基-环戊烷羧酸,
N-(2-氯-4-甲基苯乙酰基)-1-氨基-环己烷羧酸,
N-(2-氯-4-甲基苯乙酰基)-1-氨基-环庚烷羧酸,
N-(2-氯-4-甲基苯乙酰基)-1-氨基-环辛烷羧酸,
N-(4-氯-2-甲基苯乙酰基)丙氨酸,
N-(4-氯-2-甲基苯乙酰基)亮氨酸,
N-(4-氯-2-甲基苯乙酰基)异亮氨酸,
N-(4-氯-2-甲基苯乙酰基)缬氨酸,
N-(4-氯-2-甲基苯乙酰基)氨基异丁酸,
N-(4-氯-2-甲基苯乙酰基)-2-乙基-2-氨基丁酸,
N-(4-氯-2-甲基苯乙酰基)-2-甲基-2-氨基戊酸,
N-(4-氯-2-甲基苯乙酰基)-2,3-二甲基-2-氨基戊酸,
N-(4-氯-2-甲基苯乙酰基)-1-氨基-环戊烷羧酸,
N-(4-氯-2-甲基苯乙酰基)-1-氨基-环己烷羧酸,
N-(4-氯-2-甲基苯乙酰基)-1-氨基-环庚烷羧酸,
N-(4-氯-2-甲基苯乙酰基)-1-氨基-环辛烷羧酸,
N-(2-氯-4-甲基苯乙酰基)-1-氨基-2-甲基-环己烷羧酸,
N-(2-氯-4-甲基苯乙酰基)-1-氨基-3-甲基-环己烷羧酸,
N-(2-氯-4-甲基苯乙酰基)-1-氨基-4-甲基-环己烷羧酸,
N-(2-氯-4-甲基苯乙酰基)-1-氨基-3,4-二甲基-环己烷羧酸,
N-(2-氯-4-甲基苯乙酰基)-1-氨基-4-乙基-环己烷羧酸,
N-(2-氯-4-甲基苯乙酰基)-1-氨基-4-异丙基-环己烷羧酸,
N-(2-氯-4-甲基苯乙酰基)-1-氨基-4-叔丁基-环己烷羧酸,
N-(2-氯-4-甲基苯乙酰基)-1-氨基-4-甲氧基-环己烷羧酸,
N-(4-氯-2-甲基苯乙酰基)-1-氨基-2-甲基-环己烷羧酸,
N-(4-氯-2-甲基苯乙酰基)-1-氨基-3-甲基-环己烷羧酸,
N-(4-氯-2-甲基苯乙酰基)-1-氨基-4-甲基-环己烷羧酸,
N-(4-氯-2-甲基苯乙酰基)-1-氨基-3,4-二甲基-环己烷羧酸,
N-(4-氯-2-甲基苯乙酰基)-1-氨基-4-乙基-环己烷羧酸,
N-(4-氯-2-甲基苯乙酰基)-1-氨基-4-异丙基-环己烷羧酸,
N-(4-氯-2-甲基苯乙酰基)-1-氨基-4-叔丁基-环己烷羧酸,
N-(4-氯-2-甲基苯乙酰基)-1-氨基-4-甲氧基-环己烷羧酸。
式(Ⅱa)化合物可以例如从式(ⅩⅤ)的苯乙酰卤和式(ⅩⅣa)的氨基酸类出发,通过Schotten-Baumann方法制得,(Organikum[Laboratory Practical in Organic Chemistry],9th Edition,446 (1970) VEB Deutscher Verlag der Wissenschaften,Berlin)。
式(ⅩⅤ)的苯乙酰卤一般是有机化学中已知的化合物,或可通过已知方法制备。
作为用于进行本发明方法(B)、(C)、(D)、(E)、(F)、(G)和(H)的起始物质所需的式(Ⅰa)化合物可通过本发明方法(A)获得。
此外,作为用于进行本发明方法(B)、(C)、(D)、(E)、(F)、(G)和(H)的起始物质所需的下列化合物一般是有机化学或无机化学中已知的化合物:式(Ⅲ)的酰基卤、式(Ⅳ)的羧酸酐类、式(Ⅴ)的氯甲酸酯类或氯甲酸硫酯类、式(Ⅵ)的氯代一硫代甲酸酯类或氯代二硫代甲酸酯类、式(Ⅶ)的烷基卤、式(Ⅷ)的磺酰氯类、式(Ⅸ)的磷化合物、式(Ⅹ)和(Ⅺ)的金属氢氧化物、金属醇盐或胺类及式(Ⅻ)的异氰酸酯类或式(ⅩⅢ)的氨基甲酰氯。
方法(A)包含如下过程,其中式(Ⅱ)化合物(其中A、B、X、Y和R8具有上述意义)进行在碱存在下的分子内缩合反应。
可用于本发明方法(A)中的稀释剂为所有的惰性有机溶剂。可优选使用下列稀释剂:烃类,例如甲苯和二甲苯;此外有醚类,例如二丁醚、四氢呋喃、二噁烷、乙二醇二甲醚、和二甘醇二甲醚;还有极性溶剂,例如二甲亚砜、四氢噻吩砜、二甲基甲酰胺和N-甲基-吡咯烷酮,以及醇类,例如甲醇、乙醇、丙醇、异丙醇、丁醇、异丁醇和叔丁醇。
在进行本发明方法(A)时可以使用的碱(脱质子剂(deprotonating agant))是所有习用的质子受体。可优选使用下列碱:碱金属和碱土金属的氧化物、氢氧化物和碳酸盐,例如氢氧化钠、氢氧化钾、氧化镁、氧化钙、碳酸钠、碳酸钾、和碳酸钙,所有这些碱也可在相转移催化剂,例如氯化三乙基苄基铵、溴化四丁基铵、Adogen 464(=氯化甲基三烷基(C8-C10)铵)或TDA1(=三(甲氧基乙氧基乙基)胺)存在下使用。此外还可使用碱金属,例如钠或钾。可以使用的其他物质是碱金属和碱土金属的氨化物和氢化物,例如氨基化钠、氢化钠和氢化钙,而且还有碱金属醇化物,例如甲醇钠、乙醇钠和叔丁醇钾。
在进行本发明方法(A)时,反应温度可在相当大范围内变化。一般,所述方法是在0℃~250℃,优选50℃~150℃的温度下进行的。
本发明方法(A)一般在大气压力下进行。
在进行本发明方法(A)时,式(Ⅱ)的反应物和脱质子碱一般以大约等摩尔量的两倍量使用。然而,也可以使用较大过量(最多至3mol)的一种或另一种组分。
方法(Bα)包含下述方法,其中使用式(Ⅰa)化合物与式(Ⅲ)的羧酰卤反应。
可用于其中使用酰基卤的本发明方法(Bα)中的稀释剂是所有对这些化合物呈惰性的溶剂。可优选使用下列稀释剂:烃类,例如汽油、苯、甲苯、二甲苯和1,2,3,4-四氢化萘;此外有卤代烃类,例如二氯甲烷、氯仿、四氯化碳、氯苯和邻二氯苯;还有酮类,例如丙酮和甲基异丙基酮,此外还有醚类,例如乙醚、四氢呋喃和二噁烷,而且还有羧酸酯,例如乙酸乙酯,还有强极性溶剂,例如二甲亚砜和四氢噻吩砜。所述反应也可在水存在下进行,如果所述酰基卤对于水解反应是足够稳定的话。
若使用羧酰卤,则在本发明方法(Bα)的反应中的适宜酸结合剂是所有习用酸性接受体。可优选使用下列酸结合剂:叔胺,例如三乙胺、吡啶、二氮杂双环辛烷(DABCO)、二氮杂双环十一碳烯(DBU)、二氮杂双环壬烯(DBN)、Hünig碱和N,N-二甲基苯胺,此外还有碱土金属氧化物,例如氧化镁和氧化钙,而且还有碱金属碳酸盐和碱土金属碳酸盐,例如碳酸钠、碳酸钾和碳酸钙,还有碱金属氢氧化物,例如氢氧化钠和氢氧化钾。
在使用羧酰卤时,本发明方法(Bα)中的反应温度也可在相当大范围内变化。一般地,所述方法在-20℃~+150℃,优选0℃~100℃的温度下进行。
在进行本发明方法(Bα)时,式(Ⅰa)起始物质和式(Ⅲ)的羧酰卤一般以大约相当的量使用。然而,也可能以较大过量(最多至5mol)的使用羧酰卤。通过习用方法进行处理。
方法(Bβ)包含下述方法,其中式(Ⅰa)化合物与式(Ⅳ)的羧酸酐反应。
若在本发明方法(Bβ)中,使用羧酸酐作为式(Ⅳ)反应物,则可使用的稀释剂优选是那些在使用酰基卤时也优选的适宜稀释剂。此外,所用的过量的羧酸酐也可同时用作稀释剂。
在使用羧酸酐时,本发明方法(Bβ)中的反应温度也可在相当大的范围内变化。一般地,该方法在-20℃~+150℃,优选0℃~100℃的温度进行。
在进行本发明方法(Bβ)时,式(Ⅰa)的起始物质和式(Ⅳ)的羧酸酐一般以大约相当的量使用。然而,也可以使用较大过量(最多至5mol)的羧酸酐。通过习用方法进行处理。
一般地,按着进行下列步骤,其中将稀释剂和过量的羧酸酐以及所形成的羧酸通过蒸馏除去,或通过用有机溶剂或水洗涤除去。
方法(C)包含下述方法,其中使式(Ⅰa)化合物与式(Ⅴ)的氯甲酸酯类或氯甲酸硫酯类反应。
若使用有关的氯甲酸酯类或氯甲酸硫酯类,则适用于本发明方法(C)中的反应中的酸结合剂是所有习用的酸性接受体。可优选使用下列酸结合剂:叔胺类,例如三乙胺、吡啶、DABCO、DBU、DBA、Hünig碱和N,N-二甲基-苯胺,此外还有碱土金属氧化物,例如氧化镁和氧化钙,而且还有碱金属碳酸盐和碱土金属碳酸盐,例如碳酸钠、碳酸钾和碳酸钙,还有碱金属氢氧化物,例如氢氧化钠和氢氧化钾。
若使用氯甲酸酯类或氯甲酸硫酯类,则可用于本发明方法(C)中的稀释剂是所有对这些化合物呈惰性的溶剂。可优选使用下列稀释剂:烃类,例如汽油、苯、甲苯、二甲苯和1,2,3,4-四氢化萘;此外有卤代烃类,例二氯甲烷、氯仿、四氯化碳、氯苯和邻二氯苯;而且还有酮类,例如丙酮和甲基异丙基酮;此外还有醚类,例如乙醚、四氢呋喃和二噁烷;此外还有羧酸酯类,例如乙酸乙酯,还有强极性溶剂,例如二甲亚砜和四氢噻吩砜。
若使用氯甲酸酯类或氯甲酸硫酯类作为式(Ⅴ)的羧酸衍生物,则进行本发明方法(C)的反应温度可在相当大范围内变化。若所述方法在稀释剂和酸结合剂存在下进行,则反应温度一般在-20℃~+100℃,优选在0℃~50℃之间。
本发明方法(C)一般在大气压力下进行。
在进行本发明方法(C)时,式(Ⅰa)起始物质和式(Ⅴ)的有关氯甲酸酯或氯甲酸硫酯一般以大约相当的量使用。然而,也可以使用较大过量(最多至2mol)的一种反应物或另一种反应物。然后通过习用方法进行处理。一般地,接着进行下述步骤,其中除去沉淀出的盐,并通过汽提稀释剂浓缩剩下的反应混合物。
在制备方法(Dα)中,在0~120℃,优选在20~60℃,大约1mol式(Ⅵ)的氯代一硫代甲酸酯或氯代二硫代甲酸酯与每摩尔式(Ⅰa)起始化合物反应。
若必要,所加入的适宜的稀释剂为所有惰性极性有机溶剂,例如醚类、酰胺类、砜类、亚砜类,以及卤代烷烃类。
优选使用下列稀释剂:二甲亚砜、四氢呋喃、二甲基甲酰胺或二氯甲烷。
若在一种优选实施方案中,式(Ⅰa)的烯醇化物(enolate)盐是通过加入强脱质子剂例如氢化钠或叔丁醇钾进行合成的,则可免除进一步地加入酸结合剂。
若使用酸结合剂,则习用的无机碱或有机碱是适宜的,可以提及的实例为氢氧化钠、碳酸钠、碳酸钾、吡啶和三乙胺。
所述反应可以在大气压力或加压下进行,优选在大气压力下进行。用习用方法进行处理。
在制备方法(Dβ)中,每摩尔式(Ⅰa)的起始化合物加入等摩尔量或过量的二硫化碳。该方法优选在0~50℃,特别是在20~30℃的温度下进行。
经常有利地是首先通过加入脱质子剂(例如叔丁醇钾或氢化钠)制备相应的式(Ⅰa)的化合物的盐。使化合物(Ⅰa)与二硫化碳反应直到中间体产生完全,例如在室温下搅拌几小时以后。
进一步与式(Ⅶ)的烷基卤的反应优选在0~70℃,特别是在20~50℃进行。至少使用等摩尔量的烷基卤。
所述方法可在大气压力下或在加压下进行。优选在大气压力下进行。
再通过习用方法进行处理。
在制备方法(E)中,在-20~150℃,优选在20~70℃,使每摩尔式(Ⅰa)起始化合物与大约1mol磺酰氯(Ⅷ)反应。
若必要,所加入的适宜的稀释剂为所有惰性极性有机溶剂,例如醚类、酰胺类、腈类、砜类、亚砜类、或卤代烃类例如二氯甲烷。
优选使用下列稀释剂:二甲亚砜、四氢呋喃、二甲基甲酰胺和二氯甲烷。
若在一种优选实施方案中,化合物(Ⅰa)的烯醇化物(enolate)盐的合成是通过加入强的脱质子剂(例如氢化钠或叔丁醇钾)进行的,进一步的加入酸结合剂则可省去。
若使用酸结合剂,则适宜的物质为习用的无机或有机碱,可以提及的实例为氢氧化钠、碳酸钠、碳酸钾、吡啶和三乙胺。
所述反应可以在大气压力下或在加压下进行,优选在大气压力下进行。通过习用方法进行处理。
在用于制得结构(Ⅰe)化合物的制备方法(F)中,在-40℃~150℃,优选-10~110℃的温度下,使1~2摩尔,优选1~1.3摩尔式(Ⅸ)的磷化合物与每摩尔化合物(Ⅰa)反应。
若必要,所加入的适宜稀释剂为所有的惰性极性有机溶剂,例如卤代烷烃类、醚类、酰胺类、腈类、醇类、硫化物类、砜类、亚砜类等。
优选使用下列稀释剂:乙腈、二甲亚砜、四氢呋喃、二甲基甲酰胺和二氯甲烷。
若必要,所加入的适宜的酸结合剂为习用的无机或有机碱,例如氢氧化物、碳酸盐或胺类。可以提及的实例为氢氧化钠、碳酸钠、碳酸钾、吡啶和三乙胺。
所述反应可以在大气压力下或在加压下进行,优选在大气压力下进行。通过有机化学中习用的方法进行处理。所得到的最终产物优选通过结晶、色谱法纯化,或通过所谓的“早期蒸馏”,即真空除去挥发性成分来纯化。
方法(G)包含下述方法,其中使式(Ⅰa)化合物与式(Ⅹ)的金属氢氧化物或金属醇盐或式(Ⅺ)的胺类反应。
可以用于本发明方法中的稀释剂优选为醚类,例如四氢呋喃、二噁烷、乙醚、或醇类,例如甲醇、乙醇和异丙醇,也可为水。本发明方法(G)一般在大气压力下进行。反应温度一般为-20~100℃,优选为0℃~50℃。
在制备方法(Hα)中,在0~100℃,优选在20~50℃,使大约1mol式(Ⅻ)的异氰酸酯与每摩尔式(Ⅰa)的起始化合物反应。
若必要,所加入的适宜稀释剂为所有惰性有机溶剂,例如醚类、酰胺类、腈类、砜类和亚砜类。
若必要,可以加入催化剂,以便加速反应。可以非常有利地使用的催化剂为有机锡化合物,例如二月桂酸二丁基锡(dibutyltin dilaurate)。所述方法优选在大气压力下进行。
在制备方法(Hβ)中,在0~150℃,优选在20~70℃,使大约1mol式(ⅩⅢ)的氨基甲酰氯与每摩尔式(Ⅰa)的起始化合物反应。
若必要,所加入的适宜稀释剂为所有惰性极性有机溶剂,例如醚类、酰胺类、砜类、亚砜类或卤代烃类。
优选使用下列稀释剂:二甲亚砜、四氢呋喃、二甲基甲酰胺或二氯甲烷。
若在一种优选实施方案中,化合物(Ⅰa)的烯醇化物(enolate)盐的合成是通过加入强的脱质子剂(例如氢化钠或叔丁醇钾)进行的,则可省去进一步加入酸结合剂。
若使用酸结合剂,则适宜的物质为习用的无机碱或有机碱,可以提及的实例为氢氧化钠、碳酸钠、碳酸钾、三乙胺或吡啶。
所述反应可以在大气压力下或在加压下进行,优选在大气压力下进行。通过习用方法进行处理。
此类活性化合物还适用于消灭有害动物,尤其适用于节肢动物和线虫,特别是在农业、森林、贮存产品及原料的保护及卫生领域中遇到的昆虫和蜘蛛。它们对于通常敏感和有抗性的种类及其整个或部分发育阶段均有活性。上述害虫包括:
等足目,例如潮虫、鼠妇和粗潮虫。
倍足目,例如具斑马陆。
唇足目,例如食果地蜈蚣和蚰蜓属。
扁肩象目,例如庭院么蚰。
缨尾目,例如西洋衣鱼。
弹尾目,例如具刺跳虫。
直翅目,例如东方蜚蠊,美洲大蠊,马得拉蜚蠊,德国小蠊,家蟋蟀,蝼姑属,热带飞蝗,殊种蚱蜢和沙漠蝗。
革翅目,例如欧洲球螋。
等翅目,例如白蚁属。
虱目,例如葡萄瘤蚜,瘿绵蚜属,体虱,血虱属和长颚虱属。
食毛目,例如嚼虱属和畜虱属。
缨翅目,例如温室条蓟马和葱蓟马。
异翅亚目,例如褐盾蝽属,介中红蝽,甜菜拟网蝽,温带臭虫,长红蜡蝽和蜡蝽属。
同翅亚目,例如甘蓝粉虱、烟粉虱、温室粉虱、棉蚜、菜蚜、茶蔗隐瘤额蚜、豆卫矛蚜、波密卫矛蚜、苹果绵蚜、桃大尾蚜、麦长管蚜、瘤额蚜属、忽布疣额蚜、粟缢管蚜、微叶蝉属、双叶叶蝉、黑尾叶蝉、李蜡蚧、油榄盔蚧、灰飞虱、稻褐飞虱、红圆蚧、夹竹桃圆蚧、粉蚧属和木虱属。
鳞翅目,例如棉红铃虫、松尺蠖、冬天蛾、苹细蛾、苹果巢蛾、小菜蛾、黄褐天幕毛虫、黄毒蛾、毒蛾属、棉潜蛾、桔叶潜蛾、地虎属、切根虫属、夜蛾属、棉斑实蛾、实夜蛾属、甜菜夜蛾、甘蓝夜蛾、小眼夜蛾、斜纹夜蛾、粘虫属、粉纹夜蛾、苹蠹蛾、粉蝶属、螟属、玉米螟、地中海粉螟、大蜡螟、负袋衣蛾、织网衣蛾、褐织叶蛾、亚麻黄卷蛾、具网卷叶蛾、云松卷蛾、葡萄果蠹蛾、茶长卷蛾、栎绿卷叶蛾。
鞘翅目,例如具斑窃蠹、谷蠹、大豆象、家天牛、赤杨紫跳甲、马铃薯甲虫、辣根猿叶虫、叶甲属、油菜蓝跳甲、墨西哥豆瓢虫、隐金甲属、锯谷盗、花象甲属、谷象属、葡萄黑象甲、香蕉根象甲、甘蓝荚象甲、苜蓿叶象甲、皮蠹属、斑皮蠹属、圆皮蠹属、毛皮蠹属、粉蠹属、油菜花露尾甲、蛛甲属、金黄蛛甲、麦蛛甲、拟谷盗属、大黄粉虫、叩甲属、金针虫属、西方五月鳃角金龟、六月金龟和褐新西兰肋翅鳃角金龟。
膜翅目,例如锯角叶蜂属、叶蜂属、蚁属、厨蚁和胡蜂属。
双翅目,如伊蚊属、按蚊属、库蚊属、黄猩猩果蝇、家蝇属、厕蝇属、红头丽蝇、绿蝇属、金蝇属、疽蝇属、胃蝇属、虱蝇属、厩螯蝇属、狂蝇属、皮蝇属、虻属、螗蜩属、花圆毛蚊、瑞典麦杆蝇、麦花蝇属、菠菜潜叶花蝇、地中海实蝇、油榄实蝇和欧洲大蚊。
蚤目,如印鼠客蚤和角叶蚤属。
蛛形纲,如蝎和盗蛛。
蜱螨目,如粗脚粉螨、锐缘蜱属、钝缘蜱属、鸡皮刺螨、茶蔗瘿螨、桔芸锈螨、牛蜱属、扁头蜱属、花蜱属、璃眼蜱属、硬蜱属、痒螨属、皮痒螨属、疥螨属、附线螨属、苜蓿苔螨、全爪螨属和叶螨属。
本发明的活性化合物具有突出的高效杀虫和杀螨活性。
它们尤其可被成功地用于杀灭植物害虫,例如辣根猿叶虫的幼虫和黑尾叶蝉的幼虫,以及小菜蛾的幼虫。
本发明的活性化合物还可用作脱叶剂、干燥剂、除阔叶植物剂,特别是可用作除杂草剂。所谓杂草,从最广泛的意义上来说,所有的植物,只要是生长在人们所不希望它生长的地方,都可以称之为杂草。使用本发明的化合物作为广谱性除草剂或选择性除草剂,主要取决于所用的量。
本发明的活性化合物可用于除去下列植物:
以下各属的双子叶杂草:
欧白芥属、独行菜属、猪殃殃属、繁缕属、母菊属、春黄菊属、牛膝菊属、藜属、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、飞廉属、苦苣菜属、茄属、蔊菜属、水松叶属、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、车轴草属、毛莨属和蒲公英属。
以下各属的双子叶栽培作物:
棉属、大豆属、甜菜属、胡罗卜属、菜豆属、豌豆属、茄属、亚麻属、番薯属、巢菜属、菸草属、番茄属、落花生属、芸苔属、莴苣属、甜瓜属和南瓜属。
以下各属的单子叶杂草:
稗属、狗尾草属、黍属、马唐属、梯牧草属、早熟禾属、羊茅属、?6?7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、荸芥属、莞草属、雀稗属、鸭嘴草属、尖瓣花属、龙爪茅属、翦股颖属、看麦娘属和豚鼠草属(Apera)。
以下各属的单子叶栽培作物:
稻属、玉蜀黍属、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。
但本发明的活性化合物的应用决不局限用于上述各属的植物,它们也可以同样方式用于其它植物。
本发明的化合物,按照使用的浓度不同,适用于清除工业场地、铁路轨道、有树或无树的小路和场院的所有杂草。同样,这些化合物也可用于清除多年生栽培作物(如人工林、装饰林带、果园、葡萄园、柑桔园、坚果林、香蕉林、咖啡园、茶园、橡胶林、油棕榈林、可可林、浆果园和蛇麻草田)中的杂草,草坪、草皮、牧场中的杂草,以及选择性地清除一年生栽培作物中的杂草。
本发明的活性化合物特别适用于有选择地清除双子叶栽培作物中的单子叶杂草(通过在杂草出现之前和出现以后施用本发明的化合物)。例如,它们用于清除棉田或甜菜地里的杂草就非常成功。
这类活性化合物可被制成通常的各种制剂,例如溶液、乳剂、可湿性粉剂、悬浮剂、粉剂、细粉剂、糊剂、可溶性粉剂、颗粒剂、悬乳剂、用本发明的活性化合物浸泡的天然和合成的材料、以及用聚合物作外衣的微胶囊。
这些制剂用已知方法制成,例如将这类活性化合物和增量剂(即液体溶剂和/或固体载体)混合,并任意使用表面活性剂(即乳化剂和/或分散剂和/或起泡剂)。
如果采用水作增量剂,则也可用例如有机溶剂作助溶剂。适用的液体溶剂主要有:芳族化合物(如二甲苯、甲苯或烷基萘类);氯化芳族化合物和氯化脂肪烃(如氯苯类,氟乙烯类或二氯甲烷);脂肪烃(如环己烷或烷属烃,例如石油馏分);矿物油和植物油;醇类(如丁醇或乙二醇)以及它们的醚和酯;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、二甲基亚砜)以及水。
适用的固体载体有:
例如,铵盐和研碎的天然矿物(例如高岭土、粘土、滑石粉、白垩、石英、绿坡缕石、蒙脱石或硅藻土)和研碎的合成矿物(如高分散度硅石、三氧化二铝和硅酸盐);适用作颗粒剂的固体载体有:如粉碎并分级的天然岩石(例如方解石、大理石、浮石、海泡石和白云石)及合成的无机和有机粉的颗粒和有机材料颗粒(如锯末、椰壳、玉米芯碎块和烟杆);适用的乳化剂和/或起泡剂有: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,例如烷基芳基聚乙二醇醚,烷基磺酸盐、烷基硫酸盐、芳基磺酸盐及白蛋白水解产物);适用的分散剂有:如木素-亚硫酸盐废液和甲基纤维素。
在制剂中可采用的粘合剂有:例如羧甲基纤维素和粉状、颗粒状或胶乳状的天然和合成聚合物(如阿拉伯树胶、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。其它的添加剂可为矿物油和植物油。
可以采用着色剂,如无机颜料(例如氧化铁、二氧化钛和普鲁士蓝)和有机染料(如茜素染料、偶氮染料和金属酞菁染料)以及微量的营养素(如铁、锰、硼、铜、钴、钼和锌的盐)。
制剂中一般含有0.1至95%(重量)的活性化合物,优选的含量为0.5至90%。
本发明的活性化合物可以其市售制剂和由这些制剂制得的使用形式存在,作为与其它活性化合物(如杀虫剂、引诱剂、消毒剂、杀螨剂、杀线虫剂、杀真菌剂、生长调节剂或除草剂)的混合物存在。这些杀虫剂包括,例如磷酸酯类、氨基甲酸酯类、羧酸酯类、氯化烃类、苯脲类和特别是微生物产出的物质。
在混合物中特别有利的组分的实例为下列化合物:
杀真菌剂:
2-氨基丁烷、2-苯胺基-4-甲基-6-环丙基嘧啶、2′,6′-二溴-2-甲基-4′-三氟甲氧基-4′-三氟甲基-1,3-噻唑-5-N-羧酰苯胺、2,6-二氯-N-(4-三氟甲基苄基)苯甲酰胺、(E)-2-甲氧基亚氨基-N-甲基-2-(2-苯氧基苯基)乙酰胺、8-羟基喹啉硫酸盐、(E)-2-{2-[6-(2-氰基苯氧基)嘧啶-4-基氧基]-苯基}-3-甲氧基丙烯酸甲酯、(E)-甲氧基亚氨基[α-(o-甲苯氧基)-o-甲苯基]乙酸甲酯、2-苯基酚(OPP)、aldimorph、ampropylfos、敌菌灵、azaconazole、benalaxyl、碘萎灵、苯菌灵、乐杀螨、联苯、bitertanol、灭瘟素、bromuconazole、磺酸丁嘧啶、粉病定;
石硫合剂、敌菌丹、克菌丹、多菌灵、萎锈灵、甲基克杀螨、地茂散、氯化苦、百菌清、chlozolinate、硫杂灵、cymoxanil、cyproconazole、cyprofuram;
双氯酚、diclobutrazol、diclofluanid、diclomezin、防霉酚、diethofencarb、消螨普、甲嘧醇、dimethomorph、diniconazole、敌螨普、二苯胺、dipyrithion、灭菌磷、二噻农、多果定、腙菌酮、克瘟散、epoxyconazole、乙嘧醇、氯唑灵、双氯苯嘧醇、fenbuconazole、甲呋萎灵、fenitropan、fenpiclonil、fenpropidin、fenpropimorph、薯瘟锡、毒菌锡、福美铁、ferimzone、fluazinam、fludioxonil、氟菌安、fluquinconazole、flusilazole、flusulfamide、flutolanil、flutriafol、灭菌丹、fosetylaluminum、稻氨酞、麦穗宁、呋氨丙灵、furmecyclox、双辛胍胺;
六氯苯、hexaconazole、甲羟异噁唑、烯菌灵、imibenconazole、iminoctadin、iprobenfos(IBP)、异丙定、稻瘟灵;
春日霉素、铜制剂(如:氢氧化铜、环烷酸铜、王铜、硫酸铜、氧化亚铜、喹啉酮和波尔多液)、双代混剂、代森锰锌、代森锰、mepanipyrim、mepronil、氨丙灵、metconazole、methasulfocarb、甲呋菌胺、代森联、metsulfovax、myclobutanil、福美镍、异丙消、环菌灵、ofurace、oxadixyl、oxamocarb、萎锈散、pefurazoate、penconazole、pencycuron、phosdiphen、稻瘟酞、匹马菌素、哌啶宁、代森联福美锌、多氧霉素、噻菌烯、丙氯灵、杀菌利、百维灵、propiconazole、甲基代森锌、定菌磷、pyrifenox、pyrimethanil、pyroquilon、五氯硝基苯(PCNB)、硫黄粉和硫制剂、tebuconazole、tecloftalam、tecnazene、tetraconazole、噻菌灵、thicyofen、甲基托布津、福美双、tolclophos-methyl、对甲抑菌灵、三唑二甲酮、唑菌醇、triazoxide、trichlamide、三唑苯噻、环吗啉、triflumizole、嗪胺灵、triticonazole、有效霉素、烯菌酮、代森锌、福美锌:
杀菌剂:
拌棉醇、防霉酚、氯定、福美镍、春日霉素、octhilinone、呋喃羧酸、土霉素、噻菌烯、链霉素、tecloftalam、硫酸铜和其他铜制剂。
杀虫剂/杀螨剂/杀线虫剂:
abamectin、A C 303 630、乙酰甲胺磷、acrinathrin、alanycarb、丁醛肟威、alphamethrin、胺三氮螨、avermectin、A Z 60541、azadirachtin、谷硫磷A、谷硫磷M、azocyclotin、苏云金杆菌、苯噁威、benfuracarb、bensultap、beta-cyluthrin、bifenthrin、丁苯威、brofenprox、溴硫磷A、混戊威、buprofezin、butocarboxin、butylpyridaben、cadusafos、西维因、呋喃丹、三硫磷、carbosulfan、巴丹、CGA 157 419、CGA 184699、chloethocarb、chlorethoxyfos、毒虫畏、chlorfluazuron、氯甲硫磷、毒死蜱、甲基毒死蜱、cisresmethrin、clocythrin、clofentezine、杀螟腈、cycloprothrin、cyfluthrin、cyhalothrin、三环锡、氯菊酯、cyromazine、溴氰菊酯、甲基一0五九、异一0五九Ⅱ、异吸硫磷Ⅱ、diafenthiuron、二嗪农、氯线磷、敌敌畏、dicliphos、百治磷、乙硫磷、伏虫脲、乐果、dimethylvinphos、二噁硫磷、乙拌磷、克瘟散、emamectin、esfenvalerate、乙硫甲威、乙硫磷、ethofenprox、丙线磷、乙嘧硫磷、克线磷、fenazaquin、螨完锡、杀螟松、fenobucarb、fenothiocarb、fenoxycarb、fenpropathrin、fenpyrad、fenpyroximate、倍硫磷、腈氯苯苯醚菊酯、fipronil、fluazinam、flucycloxuron、flucythrinate、flufenoxuron、flufenprox、fluvalinate、地虫硫磷、安果、fosthiazate、fubfenprox、furathiocarb、六六六、heptenophos、hexaflumuron、hexythiazox、imidacloprid、iprobenfos、异丙三唑硫磷、异丙胺磷、异丙威、异噁唑硫磷、ivermectin、lambda-cyhalothrin、Lufenuron、马拉硫磷、灭蚜硫磷、速灭磷、mesulfenphos、蜗牛敌、丁烯硫磷、甲胺磷、甲噻硫磷、甲硫威、乙肟威、metolcarb、milbemectin、久效磷、moxidectin、二溴磷、NC 184、NI 25、nitenpyram、氧化乐果、草肟威、砜吸硫磷、oxydeprofos、一六0五、甲基一六0五、二氯苯醚菊酯、稻丰散、三九一一、phosalone、phosmet、phosphamidon、辛硫磷、灭定威、甲基嘧啶硫磷、嘧啶硫磷、profenofos、甲丙威、丙虫磷、残杀威、低毒硫磷、发果、pymetrozin、pyraclofos、苯哒嗪硫磷、pyresmethrin、除虫菊、pyridaben、pyrimidifen、pyriproxifen、喹噁硫磷、RH 5992、水杨硫磷、sebufos、silafluofen、硫特普、sulprofos、tebufenozid、tebufenpyrad、tebupirimiphos、teflubenzuron、tefluthrin、双硫磷、terbam、特丁三九、杀虫畏、thiafenox、thiodicarb、己酮肟威、甲基乙拌磷、嗪线磷、苏云金菌素、tralomethrin、triarathen、三唑硫磷、triazuron、敌百虫、triflumuron、trimethacarb、完灭硫磷、二甲威、xylylcarb、YI5301/5302、zetamethrin。
除草剂:
例如N-酰苯胺类,如diflufenican和敌稗;芳基羧酸类,如二氯吡啶甲酸、麦草畏和毒莠定;芳氧基链烷酸类,如2,4-D、2,4-滴丁酸、2,4-滴丙酸、氟氧吡啶、2甲4氯、2甲4氯丙酸和乙氯草定;芳氧基-苯氧基链烷酸酯,如2,4-滴苯甲酸甲酯;乙基酚丙酸、禾草枯、haloxyfop-methyl和quizalofop-ethyl;azinone类,例如chloridazon和氟哒酮;氨基甲酸酯类,例如氯苯胺灵、甜草灵、甲二威灵和苯胺灵;乙酰氯苯胺类,例如杂草锁、乙基乙草安、丁草锁、metazachlor、甲氧毒草安、氯苯胺和毒草安;二硝基苯胺类,例如磺胺乐灵、芽草平和氟乐灵;二苯醚类,例如氟锁草醚、治草醚、fluoroglycofen、虎威、halosafen、乳酚和乙氧氟甲草醚;脲类,例如绿麦隆、敌草隆、伏草隆、异丙隆、利谷隆和噻唑隆;羟胺类,例如枯杀达、乙氧定、环氧定、禾莠净和烷氧定;咪唑啉酮类,例如咪唑乙畏、咪唑甲苯、咪唑吡啶和咪唑喹啉;腈类,例如溴苯腈、敌草腈和碘苯腈;氧乙酰胺类,例如mefenacet;磺酰脲类,例如氨基磺隆、甲基苯磺隆、乙基氯默隆、阔草脲、华磺隆、甲基甲磺隆、烟磺隆、原磺隆、乙基吡唑磺隆、甲基西酚磺隆、三硫隆和甲三苯隆;硫代氨基甲酸酯类,例如苏灭达、草灭特、燕麦敌、扑草灭、esprocarb、草达灭、扑硫威、杀草丹和野麦畏;三嗪类,例如阿特拉津、草净津、西玛津、西草净、去草净和特丁津;三嗪酮类,例如敌草灵、灭它通和赛克津;及其它除草剂,例如氨三唑、benfuresate、灭草松、辛甲灵、氯马腙、氯吡啶、草吡唑、二硫吡啶、甜菜呋、fluorochloridone、glufosinate、草甘膦、异噁苯、草利达、quinchlorac、quinmerac、sulphosate和tridiphane。
本发明的活性化合物还可以以其市售制剂形式和由这些制剂制备的使用形式、作为与增效剂的混合物存在。增效剂是这样的化合物,它们可提高活性化合物的作用,而所加入的增效剂本身不必是具有活性的。
由市售制剂制得的使用形式中的活性化合物的含量可在宽的范围内变化。使用形式中的活性化合物浓度可以为0.0000001~95%(重量)活性化合物,优选0.0001~1%(重量)。
所述化合物是以适于该使用形式的习用方式使用的。
当用于对抗卫生学上的害虫及贮存产品的害虫时,本发明活性化合物对于木头和粘土具有优良的残余作用(residual action),并对于用石灰处理过的底物上的碱具有好的稳定性。
本发明活性化合物的制备和使用可以从下列实施例中发现。
制备例:
实施例(Ⅰa-1):
将12.42g叔丁醇钾加入到35ml无水四氢呋喃中,并在回流下加入16gN-(4-氯-2-甲基苯基)-乙酰基-1-氨基-环己烷羧酸甲酯在100ml无水甲苯中的溶液,并将该混合物回流90分钟。冷却后,向反应溶液中加入150ml水,并分离出水相。使用75ml水对有机相再进行洗涤。合并水相,混合物用16ml浓盐酸酸化,并抽滤出沉淀,干燥。得到11.7g(理论值的81%),m.p.162℃。
类似地制得下列化合物:
表8:
表8(续)
实施例(Ⅰb-1)
将2.1ml三乙胺加入到在70ml无水二氯甲烷中的4.38g实施例Ⅰa-1化合物中,并在0~10℃加入在5ml无水二氯甲烷中的1.58ml异丁酰氯。反应溶液用50ml 0.5N氢氧化钠溶液洗涤两次,并用硫酸镁干燥,蒸掉溶剂。剩余2.6g(理论值的47%),m.p.186℃。
类似地制得下列化合物并且按照下列一般的制备条件:
表9:
实施例(Ⅰc-1)
将2.1ml三乙胺加入到在70ml无水二氯甲烷中的4.36g实施例Ⅰa-1化合物中,并在0~10℃加入在5ml无水二氯甲烷中的1.5ml氯甲酸乙酯。反应溶液用50ml 0.5N氢氧化钠溶液洗涤两次,并用硫酸镁干燥,蒸掉溶剂。剩余4.1g(理论值的75%),m.p.184℃。
类似地制得下列化合物,并且按照下列一般制备条件:
表10
实施例Ⅰd-1
将1.4ml三乙胺加入到在70ml无水二氯甲烷中的3.05g实施例Ⅰa-8化合物中,并在0~10℃加入在5ml无水二氯甲烷中的1.15ml甲磺酰氯。反应溶液用50ml 0.5N氢氧化钠溶液洗涤两次,并用硫酸镁干燥,蒸掉溶剂。剩余3g(理论值的78%),m.p.198℃。
实施例Ⅰe-1
将3.06g(10mmol)化合物Ⅰa-8悬浮于50ml无水二氯甲烷中,并加入1.02ml(12mmol)无水异丙胺。15分钟后,真空蒸发溶剂。得到3.6g(理论值的98%)化合物Ⅰe-1,m.p.152℃。
实施例Ⅰg-1
将2.28g二氮杂双环十一碳烯加入到在50ml无水四氢呋喃中的4.59g实施例Ⅰa-8化合物中,并在0~10℃加入在5ml无水四氢呋喃中的1.76ml吗啉氨基甲酰氯,随后将该混合物回流3小时。反应溶液用50ml 0.5N氢氧化钠溶液洗涤两次,并用硫酸钠干燥,并蒸掉溶剂。剩余2.6g(理论值47%),m.p.182℃。
起始化合物的制备
实施例(Ⅱ-1):
将14.5g(75mmol)1-氨基-环己烷羧酸甲酯盐酸盐加入到180ml无水四氢呋喃中,加入21ml三乙胺,并在0~10℃滴加在20ml无水四氢呋喃中的15.2g(75mmol)4-氯-2-甲基-苯乙酰氯,并在室温继续搅拌1小时。将反应混合物倾入500ml冰-水+200ml HCl中,抽滤出沉淀出的产物并干燥。用甲基叔丁基醚/正己烷重结晶后,得到16g(理论值的65%)上面所示产物,m.p.151℃。
实施例(Ⅱ-2)
将70.4g(0.253mol)N-(2-氯-4-甲基苯乙酰基)-2-氨基-2,3-二甲基-丁腈的500ml二氯甲烷溶液滴加到124.4g(1.27mol)浓硫酸中,滴加方式要使溶液保持在中等沸腾。2小时后,滴加176ml无水甲醇,并将混合物回流6小时。将反应混合物倾入1.25kg冰中并用二氯甲烷萃取。合并的二氯甲烷相用饱和碳酸氢钠溶液洗涤并干燥,真空蒸发溶剂,残余物用甲基叔丁基醚/正己烷重结晶。
以此方式,得到69.6g(理论值的88%)化合物Ⅱ-2,m.p.96℃。
用类似于实施例(Ⅱ-1)和(Ⅱ-2)的方法制得列于表11中的实施例。
表11:
实施例(ⅩⅦ-1)
将33.6g(0.3mol)2-氨基-2,3-二甲基-丁腈加入到450ml无水四氢呋喃中,加入42ml三乙胺,并在0~10℃滴加60.9g 2-氯-4-甲基-苯乙酰氯。在室温继续搅拌1小时,将该批物料在搅拌下加入1.3升冰-水和200ml 1N HCl中,抽滤出沉淀,干燥,并用甲基叔丁基醚/正己烷重结晶。以此方式,制得70.4g(理论值的84%)上面所示产物,m.p.112℃。
类似地制得列于表12中的式(ⅩⅦ)化合物。
表12
应用实施例
实施例A
猿叶虫幼虫试验
溶剂:7份(重量)二甲基甲酰胺
乳化剂:1份(重量)烷基芳基聚乙二醇醚
为制得合适的活性化合物的制剂,将1份(重量)活性化合物与所述量的溶剂和所述量的乳化剂混合,用水将此浓缩液稀释到所需要的浓度。
将卷心菜叶在含有所需浓度的活性化合物的制剂中做浸泡处理,在叶子还湿的时候接种上辣根猿叶虫的幼虫。
经过一段规定的时间后,测定百分死亡率。100%表示所有的幼虫(beetle larvae)均被杀死,0%则表示没有幼虫(beetle larvae)被杀死。
在本试验中,例如用制备实施例Ⅰa-4和Ⅰa-5的化合物在典型的活性化合物浓度为0.01%时,7天后死亡率为100%。
实施例B
小菜蛾(Plutella)试验
溶剂:7份(重量)二甲基甲酰胺
乳化剂:1份(重量)烷基芳基聚乙二醇醚
为制得合适的活性化合物的制剂,将1份(重量)活性化合物与所述量的溶剂和所述量的乳化剂混合,用水将此浓缩液稀释到所需要的浓度。
将卷心菜叶在含有所需浓度的活性化合物的制剂中做浸泡处理,在叶子还湿的时候接种上小菜蛾的幼虫。
经过一段规定的时间后,测定百分死亡率。100%表示所有的幼虫均被杀死,0%则表示没有幼虫被杀死。
在本试验中,例如用制备实施例Ⅰa-4和Ⅰa-7的化合物在典型的活性化合物浓度为0.01%时,7天后死亡率为100%。
例如用制备实施例Ⅰb-9和Ⅰb-11的化合物在典型活性化合物浓度为0.01%时,3天后死亡率为100%。
用制备实施例Ⅰa-7(0.01%,7天)、Ⅰb-8(0.01%,3天)和Ⅰc-7(0.01%,3天)的化合物,在其活性化合物的浓度和所经历的时间如括弧中所示时,死亡率为100%。
实施例C
黑尾叶蝉(Nephotettix)试验
溶剂:7份(重量)二甲基甲酰胺
乳化剂:1份(重量)烷基芳基聚乙二醇醚
为制得合适的活性化合物的制剂,将1份(重量)活性化合物与所述量的溶剂和所述量的乳化剂混合,用水将此浓缩液稀释到所需要的浓度。
将稻秧在含有所需浓度的活性化合物的制剂中做浸泡处理,在稻秧还湿的时候接种上黑尾叶蝉。
经过一段规定的时间后,测定百分死亡率。100%表示所有的黑尾叶蝉均被杀死,0%则表示没有黑尾叶蝉被杀死。
在本试验中,例如用制备实施例Ⅰa-4、Ⅰa-5、Ⅰb-8、Ⅰb-9和Ⅰb-11的化合物在所含典型活性化合物的浓度为0.01%时,6天后死亡率为100%。
实施例D
蚜虫(Myzus)试验
溶剂:7份(重量)二甲基甲酰胺
乳化剂:1份(重量)烷基芳基聚乙二醇醚
为制得合适的活性化合物的制剂,将1份(重量)活性化合物与所述量的溶剂和所述量的乳化剂混合,用水将此浓缩液稀释到所需要的浓度。
将严重寄生有桃蚜的卷心菜叶在含有所需浓度的活性化合物的制剂中做浸泡处理。
经过一段规定的时间后,测定百分死亡率。100%表示所有的蚜虫均被杀死,0%则表示没有蚜虫被杀死。
在本试验中,例如用制备实施例Ⅰa-4、Ⅰa-7、和Ⅰa-8的化合物在典型的活性化合物浓度为0.01%时,6天后死亡率至少为70%。
例如用制备实施例Ⅰb-11的化合物在典型活性化合物浓度为0.1%时,6天后死亡率达90%。
实施例E
全爪螨试验
溶剂:3份(重量)二甲基甲酰胺
乳化剂:1份(重量)烷基芳基聚乙二醇醚
为制得合适的活性化合物的制剂,将1份(重量)活性化合物与所述量的溶剂和所述量的乳化剂混合,用乳化剂-水将此浓缩液稀释到所需要的浓度。
将含有所需浓度的活性化合物的制剂喷洒在被各发育阶段的榆后叶螨(苹果全爪螨)严重寄生的约30cm高的洋李树上。
经过一段规定的时间后,测定百分死亡率。100%表示所有的叶螨均被杀死,0%则表示没有叶螨被杀死。
在本试验中,例如用制备实施例Ⅰa-8、Ⅰb-8、Ⅰb-9、Ⅰc-7、Ⅰb-10、Ⅰb-11、Ⅰc-8、Ⅰa-4和Ⅰa-5的化合物在典型的活性化合物浓度为0.02%时,7天后死亡率至少为95%。
实施例F
红叶螨(Tetranychus)试验(有机磷(OP)抗性/喷洒处理)
溶剂:3份(重量)二甲基甲酰胺
乳化剂:1份(重量)烷基芳基聚乙二醇醚
为制得合适的活性化合物的制剂,将1份(重量)活性化合物与所述量的溶剂和所述量的乳化剂混合,用乳化剂-水将此浓缩液稀释到所需要的浓度。
将含有所需浓度的活性化合物的制剂喷洒在被各发育阶段的普通红叶螨(greenhouse red spider mite)(二点叶螨)严重寄生的菜豆植株上。
经过一段规定的时间后,测定百分死亡率。100%表示所有的叶螨均被杀死,0%则表示没有叶螨被杀死。
在本试验中,例如用制备实施例Ⅰa-7、Ⅰa-8、Ⅰb-8、Ⅰb-9、Ⅰc-7、Ⅰb-10、Ⅰb-11、Ⅰc-8、Ⅰa-4和Ⅰa-5的化合物在典型的活性化合物浓度为0.02%时,7天后死亡率至少为95%。
实施例G
出苗前试验
溶剂:5份(重量)丙酮
乳化剂:1份(重量)烷基芳基聚乙二醇醚
为制得合适的活性化合物的制剂,将1份(重量)活性化合物与所述量的溶剂混合,再加入所述量的乳化剂,用水将此浓缩液稀释到所需要的浓度。
将试验植物的种子播种在正常的土壤中,24小时后用活性化合物的制剂浇灌。最好每单位面积的土壤中使浇灌的水的量保持一致。制剂中活性化合物的浓度并不重要,每单位面积土壤中施用的活性化合物的量才是决定性的。三周后,通过与未处理的对照组植物的发育情况相比较,以百分破坏率来评价对试验植物的破坏程度。数字表示:
0%=无作用(像未处理的对照组一样)
100%=完全破坏
在本试验中,例如用制备实施例(Ⅰc-14)的化合物在典型用量为250g/公顷时,甜菜有很好的耐受力,而对下列试验植物的破坏率至少为95%:看麦粮草(Alopecurus myosuroides)、马唐草、芒稗草、多年生黑麦草和狗尾草。
Claims (14)
1、式(Ⅰ)的1H-3-芳基-吡咯烷-2,4-二酮衍生物、其非对映体混合物、纯的非对映体和对映体:
其中
A代表氢、或烷基、链烯基、烷氧基烷基或烷硫基烷基,它们各自任选被卤素取代,或代表环烷基,该环烷基任选被至少一个杂原子所间断并任选被取代,
或代表芳基、芳烷基或杂芳基,它们各自任选被卤素、烷基、卤代烷基、烷氧基或硝基所取代;
B代表氢、烷基或烷氧基烷基;或
A和B与它们所键合的碳原子一起代表饱和或不饱和的、未取代的或取代的环,该环任选被至少一个杂原子所间断;
X代表卤素或烷基;
Y代表卤素或烷基;
G代表氢(a)或下列基团之一:
E代表金属离子等同物(metal ion equivalent)或铵离子;
L和M在每种情况下代表氧或硫;
R1代表烷基、链烯基、烷氧基烷基、烷硫基烷基或多烷氧基烷基(polyalkoxyalkyl),它们各自任选被卤素所取代,或代表环烷基,该环烷基任选被卤素或烷基所取代并可被至少一个杂原子所间断,或
在每种情况下代表任选取代的苯基、苯基烷基、杂芳基、苯氧基烷基或杂芳基氧基烷基;
R2代表烷基、链烯基、烷氧基烷基或多烷氧基烷基(polyalkoxyalkyl),它们各自任选被卤素所取代,或
在每种情况下代表任选取代的环烷基、苯基或苄基;
R3、R4和R5彼此独立地代表烷基、烷氧基、烷氨基、二烷基氨基、烷硫基、链烯基硫基或环烷基硫基,它们各自任选被卤素所取代,或
在每种情况下代表任选取代的苯基、苯氧基或苯硫基;和
R6和R7彼此独立地代表氢、或烷基、环烷基、链烯基、烷氧基或烷氧基烷基,它们各自任选被卤素所取代,或
在每种情况下代表任选取代的苯基或苄基,或
与它们所键合的N原子一起代表环,该环任选被氧或硫所间断;
条件是:X和Y不同时代表烷基并且不同时代表卤素。
3、权利要求1中式(Ⅰ)的1H-3-芳基-吡咯烷-2,4-二酮衍生物,
其中
A代表氢、或C1-C12烷基、C3-C8链烯基、C1-C10烷氧基-C1-C8烷基、C1-C8-多烷氧基(polyalkoxy)-C1-C8烷基或C1-C10烷硫基-C1-C6烷基,它们各自任选被卤素取代,或代表具有3-8个环原子的环烷基,该环烷基任选被卤素、C1-C4烷基或C1-C4烷氧基取代,并可被氧和/或硫间断,或代表芳基、5~6元杂芳基或芳基-C1-C6烷基,它们各自任选被卤素、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基和/或硝基取代,
B代表氢、C1-C12烷基或C1-C8烷氧基烷基,或
A、B和它们所键合的碳原子代表饱和或不饱和的C3-C10螺环,该螺环任选被氧或硫间断,并任选被C1-C10烷基、C3-C10环烷基、C1-C6卤代烷基、C1-C10烷氧基、C1-C10烷硫基、卤素或苯基一取代或多取代,或者
A、B和它们所键合的碳原子代表C3-C6螺环,该螺环可被任选被一个或两个氧和/或硫原子所间断的亚烷二基取代,或可被亚烷二氧基或被亚烷二硫基取代,该亚烷二基、亚烷二氧基或亚烷二硫基与它们所键合的碳原子一起形成另一个五至八元螺环,或者
A、B和它们所键合的碳原子代表C3-C8螺环,其中两个取代基一起代表饱和的或不饱和的3~8元环,所述环任选被C1-C6烷基、C1-C6烷氧基或卤素取代,并可被氧或硫间断。
X代表卤素或C1-C6烷基,
Y代表卤素或C1-C6烷基,
G代表氢(a)或下列基团之一:
其中:
E代表金属离子等同物(metal ion equivalent)或铵离子,和
L和M在每种情况下代表氧或硫,
R1代表C1-C20烷基、C2-C20链烯基、C1-C8烷氧基-C1-C8烷基、C1-C8烷硫基-C1-C8烷基或C1-C8多烷氧基(polyalkoxy)-C1-C8烷基,它们各自任选被卤素取代,或代表具有3-8个环原子的环烷基,该环烷基任选被卤素或C1-C6烷基取代并可被至少一个氧和/或硫原子间断,或代表苯基,它任选被卤素、硝基、C1-C6烷基、C1-C6烷氧基、C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6烷硫基或C1-C6烷基磺酰基取代,
或代表苯基-C1-C6烷基,它任选被卤素、C1-C6烷基、C1-C6烷氧基、C1-C6卤代烷基或C1-C6卤代烷氧基取代,
或代表5或6元杂芳基,它任选被卤素和/或C1-C6烷基取代,或代表苯氧基-C1-C6烷基,它任选被卤素和/或C1-C6烷基取代,
或代表5或6元杂芳氧基-C1-C6烷基,它任选被卤素、氨基和/或C1-C6烷基取代。
R2代表C1-C20烷基、C3-C20链烯基、C1-C8烷氧基-C1-C8烷基或C1-C8多烷氧基(polyalkoxy)-C1-C8烷基,它们各自任选被卤素取代,
或代表C3-C8环烷基,它任选被卤素、C1-C4烷基和/或C1-C4烷氧基取代,
或代表苯基或苄基,它们各自任选被卤素、硝基、C1-C6烷基、C1-C6烷氧基和/或C1-C8卤代烷基取代,
R3、R4和R5彼此独立地代表C1-C8烷基、C1-C8烷氧基、C1-C8烷氨基、二(C1-C8)烷氨基、C1-C8烷硫基、C2-C8链烯基硫基或C3-C7环烷基硫基,它们各自任选被卤素取代,
或代表苯基、苯氧基或苯硫基,它们各自任选被下列基团取代:卤素、硝基、氰基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4卤代烷硫基、C1-C4烷基或C1-C4卤代烷基;和
R6和R7彼此独立地代表氢、或代表C1-C8烷基、C3-C8环烷基、C1-C8烷氧基、C3-C8链烯基或C1-C8烷氧基-C1-C8烷基,它们各自任选被卤素取代,
或代表苯基,它任选被卤素、C1-C8卤代烷基、C1-C8烷基和/或C1-C8烷氧基取代,
或代表苄基,它任选被卤素、C1-C8烷基、C1-C8卤代烷基和/或C1-C8烷氧基取代,
或一起代表C3-C6亚烷基环,它任选被氧或硫间断。
条件是:X和Y不同时代表烷基且不同时代表卤素。
4、权利要求1中式(Ⅰ)的1H-3-芳基-吡咯烷-2,4-二酮衍生物,
其中
A代表氢、或C1-C10烷基、C3-C6链烯基、C1-C8烷氧基-C1-C6烷基、C1-C6多烷氧基(polyalkoxy)-C1-C6烷基或C1-C6烷硫基-C1-C6烷基,它们各自任选被氟和/或氯取代,或代表具有3~7个环原子的环烷基,该环烷基任选被氟、氯、C1-C3烷基或C1-C3烷氧基取代并可被1或2个氧和/或硫原子间断,
或代表苯基、呋喃基、吡啶基、咪唑基、三唑基、吡唑基、吲哚基、噻唑基、噻吩基或苯基-C1-C4烷基,它们各自被氟、氯、溴、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基和/或硝基任选取代,
B代表氢、C1-C10烷基或C1-C6烷氧基烷基,或
A、B和它们所键合的碳原子代表饱和的或不饱和的C3-C9螺环,该螺环任选被氧或硫间断并任选被C1-C6烷基、C3-C8环烷基、C1-C3卤代烷基、C1-C6烷氧基、C1-C6烷硫基、氟、氯或苯基一取代或多取代,或者
A、B和它们所键合的碳原子代表C3-C6螺环,该螺环可被任选被一个或两个氧或硫原子间断的亚烷二基取代或可被亚烷二氧基或被亚烷二硫基取代,该亚烷二基、亚烷二氧基或亚烷二硫基与它们所键合的碳原子一起形成另一个5~7元螺环,或者
A、B和它们所键合的碳原子代表C3-C6螺环,其中两个取代基一起代表饱和或不饱和的5-8元环,所述环任选被C1-C3烷基、C1-C3烷氧基、氟、氯或溴取代,并可被氧或硫间断。
X代表氟、氯、溴或C1-C4烷基,
Y代表氟、氯、溴或C1-C4烷基,
G代表氢(a)或下列基团之一:
其中
E代表金属离子等同物(metal ion equivalent)或铵离子,和L和M在每种情况下代表氧或硫,
R1代表C1-C16烷基、C2-C16链烯基、C1-C6烷氧基-C1-C6烷基、C1-C16烷硫基-C1-C6烷基或C1-C6多烷氧基(polyalkoxy)-C1-C6烷基,它们各自任选被氟和/或氯取代,或代表具有3-7个环原子的环烷基,该环烷基任选被卤素或C1-C5烷基取代,并可被1或2个氧和/或硫原子间断,或代表苯基,它任选被下列基团取代:卤素、硝基、C1-C4烷基、C1-C4烷氧基、C1-C3卤代烷基、C1-C3卤代烷氧基、C1-C4烷硫基或C1-C4烷基磺酰基,
或代表苯基-C1-C4烷基,它任选被卤素、C1-C4烷基、C1-C4烷氧基、C1-C3卤代烷基或C1-C3卤代烷氧基取代,
或代表吡唑基、噻唑基、吡啶基、嘧啶基、呋喃基或噻吩基,它们各自任选被氟、氯、溴和/或C1-C4烷基取代,
或代表苯氧基-C1-C5烷基,它任选被氟、氯、溴和/或C1-C4烷基取代,
或代表吡啶氧基-C1-C5烷基、嘧啶氧基-C1-C5烷基或噻唑氧基-C1-C5烷基,它们各自任选被氟、氯、溴、氨基和/或C1-C4烷基取代,
R2代表C1-C16烷基、C3-C16链烯基、C1-C6烷氧基-C1-C6烷基或C1-C6多烷氧基(polyalkoxy)-C1-C6烷基,它们各自任选被卤素取代,
或代表C3-C7环烷基,它任选被卤素、C1-C3烷基和/或C1-C3烷氧基取代,
或代表苯基或苄基,它们各自任选被卤素、硝基、C1-C4烷基、C1-C3烷氧基和/或C1-C3卤代烷基取代。,
R3、R4和R5彼此独立地代表C1-C6烷基、C1-C6烷氧基、C1-C6烷氨基、二(C1-C6)烷基氨基、C1-C6烷硫基、C3-C4链烯基硫基或C3-C6环烷基硫基,它们各自任选被卤素取代,
或代表苯基、苯氧基或苯硫基,它们各自任选被下列基团取代:氟、氯、溴、硝基、氰基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3卤代烷硫基、C1-C3烷基或C1-C3卤代烷基;和
R6和R7彼此独立地代表氢、或代表C1-C8烷基、C3-C8环烷基、C1-C6烷氧基、C3-C6链烯基或C1-C6烷氧基-C1-C6烷基,它们各自任选被卤素取代,
或代表苯基,它任选被卤素、C1-C5卤代烷基、C1-C5烷基和/或C1-C5烷氧基取代,
或代表苄基,它任选被卤素、C1-C5烷基、C1-C5卤代烷基和/或C1-C5烷氧基取代,
或一起代表C3-C6亚烷基环,它任选被氧或硫间断。
条件是:X和Y不同时代表烷基且不同时代表卤素。
5、权利要求1中式(Ⅰ)的1H-3-芳基-吡咯烷-2,4-二酮衍生物,
其中
A代表氢、或C1-C8烷基、C3-C4链烯基、C1-C6烷氧基-C1-C4烷基、C1-C4多烷氧基(polyalkoxy)-C1-C4烷基、或C1-C6烷硫基-C1-C4烷基,它们各自任选被氟和/或氯取代,或代表具有3-6个环原子的环烷基,该环烷基任选被氟、氯、甲基、乙基、甲氧基或乙氧基取代,并可被1或2个氧和/或硫原子间断,
或代表苯基、呋喃基、吡啶基、咪唑基、吡唑基、三唑基、吲哚基、噻唑基、噻吩基或苄基,它们各自任选被氟、氯、溴、甲基、乙基、丙基、异丙基、甲氧基、乙氧基、三氟甲基和/或硝基取代,
B代表氢、C1-C8烷基或C1-C4烷氧基烷基,或
A、B和它们所键合的碳原子代表饱和的或不饱和的C3-C8螺环,该螺环任选被氧或硫间断,并任选被下列基团一取代或多取代:甲基、乙基、丙基、异丙基、丁基、异丁基、仲丁基、叔丁基、环己基、三氟甲基、甲氧基、乙氧基、丙氧基、异丙氧基、丁氧基、异丁氧基、仲丁氧基、叔丁氧基、甲硫基、乙硫基、氟、氯或苯基,或
A、B和它们所键合的碳原子代表C3-C6螺环,该螺环可被任选被氧或硫原子间断的亚烷二基取代,或代表亚烷二氧基,该亚烷二基或亚烷二氧基与它们所键合的碳原子一起形成另一个5~7元螺环,或者
A、B和它们所键合的碳原子代表C3-C6螺环,其中两个取代基一起代表饱和的或不饱和的5或6元环,该环可被氧或硫间断,
X代表氯、溴、甲基、乙基、丙基或异丙基,
Y代表氯、溴、甲基、乙基、丙基或异丙基,
G代表氢(a)或下列基团之一:
其中:
E代表金属离子等同物(metal ion equivalent)或铵离子,和
L和M在每种情况下代表氧或硫,
R1代表C1-14烷基、C2-C14链烯基、C1-C4烷氧基-C1-C6烷基、C1-C4烷硫基-C1-C6烷基或C1-C4多烷氧基(polyalkoxy)-C1-C4烷基,它们各自任选被氟和/或氯取代,或代表具有3-6个环原子的环烷基,它任选被氟、氯、甲基、乙基、丙基、异丙基、丁基、异丁基或叔丁基取代,并可被1或2个氧和/或硫原子间断,
或代表苯基,它任选被氟、氯、溴、硝基、甲基、乙基、丙基、异丙基、甲氧基、乙氧基、三氟甲基、三氟甲氧基、甲硫基、乙硫基、甲磺酰基、或乙磺酰基取代,
或代表苯基-C1-C3烷基,它任选被氟、氯、溴、甲基、乙基、丙基、异丙基、甲氧基、乙氧基、三氟甲基或三氟甲氧基取代,
或代表呋喃基、噻吩基、吡啶基、嘧啶基、噻唑基或吡唑基,它们各自任选被氟、氯、溴、甲基或乙基取代,
或代表苯氧基-C1-C4烷基,它们各自任选被氟、氯、甲基和/或乙基取代,
或代表吡啶氧基-C1-C4烷基、嘧啶氧基-C1-C4烷基或噻唑氧基-C1-C4烷基,它们各自任选被氟、氯、氨基、甲基或乙基取代,
R2代表C1-14烷基、C3-C14链烯基、C1-C4烷氧基-C1-C6烷基或C1-C4多烷氧基(polyalkoxy)-C1-C6烷基,它们各自任选被氟和/或氯取代,
或代表C3-C6环烷基,它任选被氟、氯、甲基、乙基、丙基、异丙基、或甲氧基取代,
或代表苯基或苄基,它们各自任选被氟、氯、硝基、甲基、乙基、丙基、异丙基、甲氧基、乙氧基或三氟甲基取代,
R3、R4和R5彼此独立地代表C1-C4烷基、C1-C4烷氧基、C1-C4烷氨基、二(C1-C4)烷基氨基、或C1-C4烷硫基,它们各自任选被氟和/或氯取代,
或代表苯基、苯氧基或苯硫基,它们各自任选被氟、氯、溴、硝基、氰基、C1-C2烷氧基、C1-C2氟代烷氧基、C1-C2烷硫基、C1-C2氟代烷硫基或C1-C3烷基取代,和
R6和R7彼此独立地代表氢、或代表C1-C4烷基、C3-C6环烷基、C1-C4烷氧基、C3-C4链烯基或C1-C4烷氧基-C1-C4烷基,它们各自任选被氟、氯或溴取代,或代表苯基,它任选被氟、氯、溴、C1-C4卤代烷基、C1-C4烷基和/或C1-C4烷氧基取代,
或代表苄基,它任选被氟、氯、溴、C1-C4烷基、C1-C4卤代烷基和/或C1-C4烷氧基取代,
或一起代表C4-C6亚烷基环,它任选被氧或硫间断。
条件是:X和Y不同时代表烷基且不同时代表卤素。
6、用于制备权利要求1中式(Ⅰ)的取代的1H-3-芳基-吡咯烷-2,4-二酮衍生物的方法,其中:
(A)式(Ⅰa)的1H-3-芳基-吡咯烷-2,4-二酮类化合物或它们的烯醇类化合物可这样制得:
其中:
A、B、X和Y具有权利要求1中所给出的意义,
即在稀释剂和在碱的存在下,使式(Ⅱ)的N-酰基氨基酸酯类进行分子内缩合反应,
其中:
A、B、X和Y具有上述意义,和
R8代表烷基,或者
(B)式(Ⅰb)化合物可如下制得:
其中:
A、B、X、Y和R1具有权利要求1中所给出的意义,即使式(Ⅰa)化合物
其中:
A、B、X和Y具有上述意义,
α)与式(Ⅲ)的酰基卤类化合物反应,
其中:
R1具有上述意义,和
Hal 代表卤素,
如果必要在稀释剂的存在下进行,以及如果必要,在酸结合剂的存在下进行,或者
β)与式(Ⅳ)的羧酸酐类化合物反应:
其中:
R1具有上述意义,
如果必要在稀释剂的存在下进行,以及如果必要在酸结合剂的存在下进行;或者
(C)式(Ⅰc-a)化合物可如下制得:
其中:
A、B、X、Y和R2具有权利要求1中所给出的意义,和
M代表氧或硫,
即使式(Ⅰa)化合物与式(Ⅴ)的氯甲酸酯类或氯甲酸硫酯类化合物反应,
其中:
A、B、X和Y具有上述意义,
其中:
R2和M具有上述意义,
如果必要在稀释剂存在下反应,以及如果必要在酸结合剂的存在下进行;或者
(D)式(Ⅰc-b)化合物可如下制得:
其中:
A、B、R2、X和Y具有上述意义,和
M代表氧或硫,
即使式(Ⅰa)化合物
其中:
A、B、X和Y具有上述意义
α)与式(Ⅵ)的氯代一硫代甲酸酯类或氯代二硫代甲酸酯类化合物反应,
其中:
M和R2具有上述意义,
如果必要在稀释剂存在下反应,并且如果必要在酸结合剂存在下反应,或者
β)与二硫化碳反应,并随后与式(Ⅶ)的烷基卤类化合物反应,
其中:
R2具有上述意义,和
Hal 代表氯、溴或磺;
或者
(E)式(Ⅰd)化合物可如下制得:
其中:
A、B、X、Y和R3具有权利要求1中所给出的意义,即使式(Ⅰa)化合物与式(Ⅷ)的磺酰氯类化合物反应,
其中:
A、B、X和Y具有上述意义,
其中:
R3具有上述意义,
如果必要在稀释剂的存在下进行,并且如果必要在酸结合剂的存在下进行;或者
(F)式(Ⅰe)的3-芳基-吡咯烷-2,4-二酮类化合物可如下制得:
其中:
A、B、L、X、Y、R4和R5具有权利要求1中所给出的意义,
即使式(Ⅰa)的1H-3-芳基吡咯烷-2,4-二酮类化合物或其烯醇类化合物与式(Ⅸ)的磷化合物反应,
其中:
A、B、X和Y具有上述意义,
其中:
L、R4和R5具有上述意义,和
Hal 代表卤素,
如果必要在稀释剂的存在下进行,并且如果必要在酸结合剂的存在下进行,或者
(G)式(Ⅰf)化合物可如下制得:
其中:
A、B、X和Y具有上述意义,和
E代表金属离子等同物(metal ion equivalent)或铵离子,即使式(Ⅰa)化合物与式(Ⅹ)和(Ⅺ)的金属氢氧化物、金属醇盐或胺反应,
其中:
A、B、X和Y具有上述意义,
其中:
Me代表一价或二价的金属离子,
t代表数字1或2;和
R10、R11和R12彼此独立地代表氢和/或烷基,
如果必要在稀释剂的存在下进行,或者
(H)式(Ⅰg)化合物可如下制得:
其中:
A、B、L、X、Y、R6和R7具有权利要求1中所给出的意义,
即使式(Ⅰa)化合物
其中:
A、B、X和Y具有上述意义,
α)与式(Ⅻ)的异氰酸酯类或异硫氰酸酯类化合物反应,
其中:
L和R6具有上述意义,
如果必要,在稀释剂存在下进行,并且如果必要在催化剂存在下进行,或者
β)与式(ⅩⅢ)的氨基甲酰氯类或硫代氨基甲酰氯类化合物反应,
其中:
L、R6和R7具有上述意义,
如果必要在稀释剂存在下进行,并且如果必要在酸结合剂存在下进行。
9、式(ⅩⅦ)化合物,
其中
A、B、X和Y具有权利要求1中所给出的意义。
11、一种杀虫剂或除草剂,它包含至少一种权利要求1中式(Ⅰ)的1H-3-芳基-吡咯烷-2,4-二酮衍生物。
12、权利要求1中式(Ⅰ)的1H-3-芳基-吡咯烷-2,4-二酮衍生物用于防治害虫和不希望的赘生物的用途。
13、防治害虫的方法,其中使权利要求1中式(Ⅰ)的1H-3-芳基-吡咯烷-2,4-二酮衍生物作用于害虫、不希望的赘生物和/或其环境。
14、用于制备杀虫剂和除草剂的方法,该方法包含使权利要求1中式(Ⅰ)的1H-3-芳基-吡咯烷-2,4-二酮衍生物与增量剂和/或表面活性剂混合。
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DE4404001 | 1994-02-09 | ||
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DEP4431730.1 | 1994-09-06 | ||
DE4431730A DE4431730A1 (de) | 1994-02-09 | 1994-09-06 | Substituierte 1H-3-Aryl-pyrrolidin-2,4-dion-Derivate |
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CN (1) | CN1080719C (zh) |
AU (1) | AU1157095A (zh) |
BR (1) | BR9500475A (zh) |
CA (1) | CA2141923A1 (zh) |
DE (2) | DE4431730A1 (zh) |
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WO2019197620A1 (de) | 2018-04-13 | 2019-10-17 | Bayer Cropscience Aktiengesellschaft | Verwendung von tetramsäurederivaten zur bekämpfung von speziellen insekten |
WO2019197617A1 (de) | 2018-04-13 | 2019-10-17 | Bayer Cropscience Aktiengesellschaft | Verwendung von tetramsäurederivaten zur bekämpfung von tierischen schädlingen durch angiessen, tröpfchenapplikation. pflanzlochbehandlung oder furchenapplikation |
AU2019250600A1 (en) | 2018-04-13 | 2020-10-22 | Bayer Aktiengesellschaft | Use of tetramic acid derivatives for controlling specific insects |
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ES2063108T3 (es) * | 1989-01-07 | 1995-01-01 | Bayer Ag | Derivados de 3-aril-pirrolidin-2,4-diona. |
DE4107394A1 (de) * | 1990-05-10 | 1991-11-14 | Bayer Ag | 1-h-3-aryl-pyrrolidin-2,4-dion-derivate |
DE4121365A1 (de) * | 1991-06-28 | 1993-01-14 | Bayer Ag | Substituierte 1-h-3-aryl-pyrrolidin-2,4-dion-derivate |
DE4223015A1 (de) * | 1992-07-13 | 1994-01-20 | Bayer Ag | Substituierte 3-Benzoyl-pyrrolidin-2,4-dion-Derivate |
DE4236400A1 (de) * | 1992-10-28 | 1994-05-05 | Bayer Ag | N-Phenylacetaminonitrile |
AU666040B2 (en) * | 1992-10-28 | 1996-01-25 | Bayer Aktiengesellschaft | Substituted 1-H-3-aryl-pyrrolidine-2,4-dione derivatives |
DE4306259A1 (de) * | 1993-03-01 | 1994-09-08 | Bayer Ag | Dialkyl-1-H-3-(2,4-dimethylphenyl)-pyrrolidin-2,4-dione, ihre Herstellung und ihre Verwendung |
DE4306257A1 (de) * | 1993-03-01 | 1994-09-08 | Bayer Ag | Substituierte 1-H-3-Phenyl-5-cycloalkylpyrrolidin-2,4-dione, ihre Herstellung und ihre Verwendung |
-
1994
- 1994-09-06 DE DE4431730A patent/DE4431730A1/de not_active Withdrawn
-
1995
- 1995-01-03 US US08/383,801 patent/US5622917A/en not_active Expired - Lifetime
- 1995-01-27 TW TW084100725A patent/TW370450B/zh active
- 1995-01-27 EP EP95101136A patent/EP0668267B1/de not_active Expired - Lifetime
- 1995-01-27 ES ES95101136T patent/ES2114238T3/es not_active Expired - Lifetime
- 1995-01-27 DE DE59501802T patent/DE59501802D1/de not_active Expired - Fee Related
- 1995-02-06 KR KR1019950002074A patent/KR100377349B1/ko not_active IP Right Cessation
- 1995-02-06 AU AU11570/95A patent/AU1157095A/en not_active Abandoned
- 1995-02-06 CA CA002141923A patent/CA2141923A1/en not_active Abandoned
- 1995-02-08 RU RU95101836/04A patent/RU95101836A/ru unknown
- 1995-02-08 BR BR9500475A patent/BR9500475A/pt not_active IP Right Cessation
- 1995-02-08 JP JP04261395A patent/JP3626235B2/ja not_active Expired - Fee Related
- 1995-02-09 CN CN95101670A patent/CN1080719C/zh not_active Expired - Fee Related
-
1996
- 1996-12-03 US US08/759,352 patent/US5847211A/en not_active Expired - Fee Related
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1319929C (zh) * | 1998-03-26 | 2007-06-06 | 拜尔公司 | 芳基苯基取代的环状酮烯醇类化合物 |
CN101056852B (zh) * | 2004-09-16 | 2013-05-01 | 拜尔农作物科学股份公司 | 碘代苯基取代的环状酮烯醇 |
Also Published As
Publication number | Publication date |
---|---|
EP0668267B1 (de) | 1998-04-08 |
US5622917A (en) | 1997-04-22 |
JP3626235B2 (ja) | 2005-03-02 |
DE4431730A1 (de) | 1995-08-10 |
KR100377349B1 (ko) | 2003-08-25 |
BR9500475A (pt) | 1996-02-27 |
US5847211A (en) | 1998-12-08 |
CA2141923A1 (en) | 1995-08-10 |
AU1157095A (en) | 1995-08-17 |
EP0668267A1 (de) | 1995-08-23 |
RU95101836A (ru) | 1996-11-20 |
CN1080719C (zh) | 2002-03-13 |
JPH07252222A (ja) | 1995-10-03 |
KR950032115A (ko) | 1995-12-20 |
ES2114238T3 (es) | 1998-05-16 |
TW370450B (en) | 1999-09-21 |
DE59501802D1 (de) | 1998-05-14 |
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