CN1119310C - 环戊烷-1,3-二酮衍生物 - Google Patents
环戊烷-1,3-二酮衍生物 Download PDFInfo
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- CN1119310C CN1119310C CN96198921A CN96198921A CN1119310C CN 1119310 C CN1119310 C CN 1119310C CN 96198921 A CN96198921 A CN 96198921A CN 96198921 A CN96198921 A CN 96198921A CN 1119310 C CN1119310 C CN 1119310C
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- LOGSONSNCYTHPS-UHFFFAOYSA-N cyclopentane-1,3-dione Chemical class O=C1CCC(=O)C1 LOGSONSNCYTHPS-UHFFFAOYSA-N 0.000 title 1
- 229910052796 boron Inorganic materials 0.000 claims abstract description 105
- -1 bicyclic cyclopentane-1,3-dione derivatives Chemical class 0.000 claims abstract description 90
- 238000000034 method Methods 0.000 claims abstract description 78
- 238000002360 preparation method Methods 0.000 claims abstract description 54
- 239000004009 herbicide Substances 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 153
- 239000000460 chlorine Substances 0.000 claims description 131
- 229910052801 chlorine Inorganic materials 0.000 claims description 78
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 73
- 238000006243 chemical reaction Methods 0.000 claims description 62
- 229910052736 halogen Inorganic materials 0.000 claims description 47
- 150000002367 halogens Chemical group 0.000 claims description 47
- 239000002253 acid Substances 0.000 claims description 38
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 34
- 239000003795 chemical substances by application Substances 0.000 claims description 34
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 32
- 229910052794 bromium Inorganic materials 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 25
- 150000002431 hydrogen Chemical class 0.000 claims description 25
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
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- 125000000217 alkyl group Chemical group 0.000 claims description 18
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- 125000004119 disulfanediyl group Chemical group *SS* 0.000 claims description 4
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- 125000003545 alkoxy group Chemical group 0.000 description 36
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- 239000002904 solvent Substances 0.000 description 34
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
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- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 11
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—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
- C07D317/72—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 spiro-condensed with carbocyclic rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing keto or thioketo groups as part of a ring, e.g. cyclohexanone, quinone; Derivatives thereof, e.g. ketals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
- C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
- C07C309/66—Methanesulfonates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/455—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation with carboxylic acids or their derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/687—Unsaturated compounds containing a keto groups being part of a ring containing halogen
- C07C49/697—Unsaturated compounds containing a keto groups being part of a ring containing halogen containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
- C07C49/747—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C62/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C62/18—Saturated compounds containing keto groups
- C07C62/26—Saturated compounds containing keto groups containing singly bound oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/013—Esters of alcohols having the esterified hydroxy group bound to a carbon atom of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C69/757—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
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Abstract
本发明涉及新颖的式(I)的二环状环戊烷-1,3-二酮衍生物,其制备方法及其作为杀虫剂和除草剂的应用。式(I)中,A、B、B’、G、Q、X、Y和Z各如说明书中所定义。
Description
本发明涉及新颖的环戊烷-1,3-二酮衍生物,其制备方法及其作为除草剂和杀虫剂(pesticides)的应用。
已知某些取代的2-芳基环戊二酮如2-(2’,4’-二甲基苯基)-4,5,6,7,8,9-六氢-1,3-茚二酮具有除草和杀螨性能(参见,例如US 4283 348;4 338 122;4 436 666;4 526 723;4 551 547和4 626698)。而且,2-(2,4,6-三甲基苯基)-1,3-茚二酮由文献J.EconomicEntomology[经济昆虫学杂志]
66,(1973),584和专利公开说明书DE 2 361 084已知,且提到了除草和杀螨活性。
再者,WO 96/01 798和WO 96/03 366描述了2-芳基-环戊烷-1,3-二酮衍生物作为除草剂和杀虫剂的应用。
然而,这些现有技术化合物的活性,特别是在低施用量和浓度的情况下,并非在所有的应用领域均令人满意。再者,对于作物而言,这些已知化合物并不总是具有充分的植物安全性。
因此,本发明提供了新颖的式(I)的二环状环戊烷-1,3-二酮衍生物
其中
X代表卤素、烷基、链烯基、烷氧基、链烯氧基、烷硫基、烷基亚磺酰基、烷基磺酰基、卤代烷基、卤代烷氧基、卤代链烯氧基、硝基、氰基或均可任选取代的苯基、苯氧基、苯硫基、苄氧基或苄硫基,
Y代表氢、卤素、烷基、链烯基、烷氧基、链烯氧基、烷硫基、烷基亚磺酰基、烷基磺酰基、卤代烷基、卤代烷氧基、卤代链烯氧基、硝基或氰基,
Z代表卤素、烷基、链烯基、烷氧基、链烯氧基、卤代烷基、卤代烷氧基、卤代链烯氧基、硝基或氰基,其条件是X、Y和Z不可同时代表甲基;
或可以由烷二基基团桥接,
B和B’相互独立地各代表氢、卤素或烷基,或一起代表均可任选取代的烷二基或烯二基,
其中
E代表金属离子等价物或铵离子,
L代表氧或硫,和
M代表氧或硫,
R1代表均可任选取代的烷基、链烯基、烷氧基烷基、烷硫基烷基或多烷氧基烷基或环烷基,它们可以含有至少一个杂原子,均可任选取代的苯基、苯烷基、杂芳基、苯氧基烷基或杂芳氧基烷基,
R2代表均可任选取代的烷基、环烷基、链烯基、烷氧基烷基、多烷氧基烷基、苯基或苄基,
R3、R4和R5相互独立地各代表均可任选卤素取代的烷基、烷氧基、烷氨基、二烷氨基、烷硫基、链烯硫基、环烷基硫基或代表均可任选取代的苯基、苯烷基、苯氧基或苯硫基,
R6代表氢,均可任选卤素取代的烷基、链烯基、烷氧基烷基,代表均可任选取代的环烷基、苯基或苄基,
R7代表氢或代表均可任选卤素取代的烷基或链烯基,或
R6和R7与连接的N原子一起形成任选含有氧或硫且任选取代的环,
R8和R9相互独立地各代表氢或均可任选取代的烷基、苯基或苯烷基,或一起代表均可任选取代的烷二基基团,和
R10和R11相互独立地各代表均可任选卤素取代的烷基、链烯基、烷氧基、烷氨基、二烷氨基、链烯基氨基或二链烯基氨基或均可任选取代的苯基或苄基。
根据取代基G的位置,式(I)化合物可以以式(I-A)和(I-B)两种异构体形式存在,它由式(I)中虚线表示:
式(I-A)和式(I-B)化合物也可以以混合物或其纯异构体形式存在。式(I-A)和式(I-B)化合物的混合物任选用常规的物理方法分离,例如通过色谱法。
为了简明起见,下文中,在每一种情形下只示出其可能异构体之一。即使如此,这种提法应理解所讨论的化合物可以以异构体的混合物或以相应的另一异构体形式存在。
包括基团G的各种含意(a)、(b)、(c)、(d)、(e)、(f)和(g),得到下列主结构(Ia)至(Ig):
其中
A、B、B’、E、L、M、Q、X、Y、Z、R1、R2、R3、R4、R5、R6和R7各如上所定义。
由于一或多个手性中心,式(Ia)-(Ig)化合物通常获得的是其立体异构体混合物。它们可以以其非对映异构体混合物或以纯的非对映异构体或对映体形式存在和使用。
此外,业已发现,新颖的式(I)的取代的环戊烷-1,3-二酮衍生物通过描述于下文的方法之一获得:
(A)如下获得式(Ia)的环戊烷-1,3-二酮或其烯醇
其中
A、B、B’、Q、X、Y和Z各如上所定义,
在稀释剂存在下和在碱存在下,
使式(II)的5-芳基-4-酮-戊酸酯进行分子内缩合反应
其中
A、B、B’、Q、X、Y和Z各如上所定义,
且
R12代表烷基(优选C1-C6-烷基);和
(B)如下获得式(Ib)化合物:
其中
A、B、B’、Q、X、Y、Z和R1各如上所定义,
其中
A、B、B’、X、Y、Z和Q各如上所定义,
其中
R1如上所定义
Hal代表卤素(特别是氯或溴);
或
β)如果适当的话在稀释剂存在下,且如果适当的话在酸结合剂存在下,与式(IV)的羧酸酐反应
R1-CO-O-CO-R1 (IV)
其中
R1如上所定义;和
(C)如下获得式(Ic-1)化合物:
其中A、B、B’、Q、X、Y、Z和R2各如上所定义,
且
M代表氧或硫,
如果适当的话在稀释剂存在下,且如果适当的话在酸结合剂存在下,
其中
A、B、B’、Q、X、Y和Z各如上所定义,
R2-M-CO-Cl (V)
其中
R2和M各如上所定义;和
(D)如下获得式(Ic-2)化合物:
其中A、B、B’、Q、X、Y、Z和R2各如上所定义,
且
M代表氧或硫,
使式(Ia)化合物
其中
A、B、B’、Q、X、Y和Z各如上所定义,
其中
M和R2各如上所定义;
或
β)如果适当的话在稀释剂存在下,且如果适当的话在碱存在下,与二硫化碳反应,之后与通式(VII)的烷基卤反应
R2-Hal (VII)
其中
R2如上所定义,且
Hal代表氯、溴或碘;
和
其中A、B、B’、Q、X、Y、Z和R3各如上所定义,
如果适当的话在稀释剂存在下,且如果适当的话在酸结合剂存在下,
使式(Ia)化合物与式(VIII)的磺酰氯反应
其中
A、B、B’、Q、X、Y和Z各如上所定义,
R3-SO2-Cl (VIII)
其中
R3如上所定义;和
(F)如下获得式(Ie)化合物:
其中A、B、L、B’、Q、X、Y、Z、R4和R5各如上所定义,
如果适当的话在稀释剂存在下,且如果适当的话在酸结合剂存在下,
使式(Ia)化合物或其烯醇与式(IX)的磷化合物反应
其中
其中
L、R4和R5各如上所定义
且
Hal代表卤素(特别是氯和溴);
和
(G)如下获得式(If)化合物:
其中A、B、B’、Q、X、Y和Z各如上所定义,
且
E代表金属离子等价物或代表铵离子,
如果适当的话在稀释剂存在下,
其中
A、B、B’、Q、X、Y和Z各如上所定义,
MeR16 (X)
其中
Me代表一或二价金属离子(特别是锂、钠、钾、镁或钙),
t代表数字1或2,
R13、R14和R15相互独立地各代表氢或烷基(特别是C1-C8-烷基);和
R16代表氢、羟基或C1-C4-烷氧基;
(H)再者,现已发现,如下获得式(Ig)化合物:
其中
A、B、L、B’、Q、X、Y、Z、R6和R7各如上所定义,
其中
A、B、B’、Q、X、Y和Z各如上所定义,
α)如果适当的话在稀释剂存在下,且如果适当的话在催化剂存在下,与式(XII)化合物反应
R6-N=C=L (XII)
其中
L和R6如上所定义;
或
β)如果适当的话在稀释剂存在下,且如果适当的话在酸结合剂存在下,与式(XIII)的氨基甲酰氯或硫代氨基甲酰氯反应
其中
L、R6和R7各如上所定义。
此外,已发现,新的式(I)化合物具有突出的杀虫、杀螨和除草活性。
式(I)提供本发明化合物的定义。
在上下文提到的结构式中列出的优选取代基或基团的范围说明如下:
X
优选代表卤素、C1-C6-烷基、C2-C6-链烯基、C1-C6-烷氧基、C2-C6-链烯氧基、C1-C6-烷硫基、C1-C6-烷基亚磺酰基、C1-C6-烷基磺酰基、C1-C6-卤代烷基、C1-C6-卤代烷氧基、C2-C6-卤代链烯氧基、硝基、氰基或均可任选被卤素-、C1-C6-烷基-、C1-C6-烷氧基-、C1-C4-卤代烷基-、C1-C4-卤代烷氧基-、硝基-或氰基-取代的苯基、苯氧基、苯硫基、苄氧基或苄硫基。
Y
优选代表氢、卤素、C1-C6-烷基、C2-C6-链烯基、C1-C6-烷氧基、C2-C6-链烯氧基、C1-C6-烷硫基、C1-C6-烷基亚磺酰基、C1-C6-烷基磺酰基、C1-C6-卤代烷基、C1-C6-卤代烷氧基、C2-C6-卤代链烯氧基、硝基或氰基。
Z
优选代表卤素、C1-C6-烷基、C2-C6-链烯基、C1-C6-烷氧基、C2-C6-链烯氧基、C1-C6-卤代烷基、C1-C6-卤代烷氧基、C2-C6-卤代链烯氧基、硝基或氰基。
A和Q一起优选代表C1-C6-烷二基或C2-C6-烯二基,它们任选被来自由下列这组基团组成的相同或不同取代基单至三取代:由卤素、羟基、巯基,和由C1-C10-烷基、C1-C6-烷氧基、C1-C6-烷硫基、C3-C7-环烷基,它们各任选被相同或不同的卤素单至九取代,和由苄氧基和苯基,它们各任选被来自由卤素、C1-C6-烷基和C1-C6-烷氧基组成的这组相同或不同的取代基单至五取代,上述C1-C6-烷二基或C2-C6-烯二基还可以含有下列基团之一: 或
或由C1-C2-烷二基基团桥接。
B和B’相互独立地各优选代表氢、卤素或C1-C6-烷基或一起优选代表均可任选C1-C6-烷基取代的C1-C6-烷二基或C2-C4-烯二基。
G,
优选代表氢(a)或代表下列基团之一
E(f)或
其中
E代表金属离子等价物或铵离子,
L代表氧或硫,和
M代表氧或硫。
R1优选代表C1-C20-烷基、C2-C10-链烯基、C1-C8-烷氧基-C1-C8-烷基、C1-C8-烷硫基-C1-C8-烷基、多-C1-C8-烷氧基-C1-C8-烷基,它们各任选被相同或不同的卤素单或多取代,或优选代表C3-C8-环烷基,它任选被来自由卤素、C1-C6-烷基和C1-C6-烷氧基组成的这组相同或不同的取代基单或多取代且其中至少一个亚甲基基团可以由氧和/或硫代替,
优选代表苯基,它任选被来自由卤素、硝基、氰基、C1-C6-烷基、C1-C6-烷氧基、C1-C6-卤代烷基和C1-C6-卤代烷氧基组成的这组相同或不同的取代基单或多取代,
优选代表苯基-C1-C6-烷基,它任选被来自由卤素、C1-C6-烷基、C1-C6-烷氧基、C1-C6-卤代烷基和C1-C6-卤代烷氧基组成的这组相同或不同的取代基单或多取代,
优选代表杂芳基,它任选被来自由卤素和C1-C6-烷基组成的这组相同或不同的取代基单或多取代,且具有5或6个环原子和一至三个选自氧、硫和氮的杂原子,
优选代表苯氧基-C1-C6-烷基,它任选被来自由卤素和C1-C6-烷基组成的这组相同或不同的取代基单或多取代,或
优选代表杂芳氧基-C1-C6-烷基,它任选被来自由卤素、氨基和C1-C6-烷基组成的这组相同或不同的取代基单或多取代,且具有5或6个环原子和一至三个选自氧、硫和氮的杂原子。
R2优选代表C1-C20-烷基、C2-C10-链烯基、C1-C8-烷氧基-C2-C8-烷基或多-C1-C8-烷氧基-C2-C8-烷基,它们各任选被相同或不同的卤素单或多取代,
优选代表C3-C6-环烷基,它任选被来自由卤素、C1-C6-烷基和C1-C6-烷氧基组成的这组相同或不同的取代基单或多取代,
优选代表苯基或苄基,它们各任选被来自由卤素、硝基、氰基、C1-C6-烷基、C1-C6-烷氧基、C1-C3-卤代烷氧基和C1-C3-卤代烷基组成的这组相同或不同的取代基单或多取代。
R3优选代表C1-C12-烷基,它任选被相同或不同的卤素单或多取代,或优选代表苯基或苯基-C1-C4-烷基,它们各任选被来自由卤素、C1-C6-烷基、C1-C6-烷氧基、C1-C3-卤代烷基、C1-C3-卤代烷氧基、氰基和硝基组成的这组相同或不同的取代基单或多取代。
R4和R5相互独立地各优选代表C1-C8-烷基、C1-C8-烷氧基、C1-C8-烷基氨基、二-(C1-C8-烷基)氨基、C1-C8-烷硫基、C3-C5-烯硫基、C3-C7-环烷基硫基,它们各任选被相同或不同的卤素单或多取代,或优选代表苯基、苯氧基或苯硫基,它们各任选被来自由卤素、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-烷基和C1-C4-卤代烷基组成的这组相同或不同的取代基单或多取代。
R6优选代表氢,优选代表C1-C10-烷基、C3-C8-烯基、C1-C8-烷氧基-C2-C8-烷基,它们各任选被相同或不同的卤素单或多取代,优选代表C3-C10-环烷基,它任选被来自由卤素、C1-C6-烷基、C1-C6-烷氧基、C1-C3-卤代烷基和C1-C3-卤代烷氧基组成的这组相同或不同的取代基单或多取代,优选代表苯基,该苯基任选被来自由卤素、C1-C3-卤代烷基、C1-C8-烷基、C1-C3-卤代烷氧基和C1-C8-烷氧基组成的这组相同或不同的取代基单或多取代,或优选代表苄基,该苄基任选被来自由卤素、C1-C8-烷基、C1-C3-卤代烷基、C1-C3-卤代烷氧基和C1-C8-烷氧基组成的这组相同或不同的取代基单或多取代,
R7优选代表氢或优选代表C1-C10-烷基或C3-C10-烯基,它们各任选被相同或不同的卤素单或多取代,或
R6和R7优选与连接的N原子结合,形成任选含氧或硫的且任选C1-C6-烷基取代的3-至7-元环。
R8和R9相互独立地各优选代表氢,优选代表C1-C6-烷基,它任选被相同或不同的卤素单或多取代,或优选代表苯基或苯基-C1-C4-烷基,它们各任选被来自由卤素、C1-C6-烷基、C1-C6-烷氧基、C1-C6-卤代烷基、C1-C6-卤代烷氧基、硝基和氰基组成的这组相同或不同的取代基单或多取代,
或一起优选代表C2-C6-烷二基,该烷二基任选被来自由卤素、C1-C6-烷基、C1-C6-烷氧基和C1-C3-卤代烷基组成的这组相同或不同的取代基单或多取代,和
R10和R11相互独立地各优选代表C1-C10-烷基、C2-C10-链烯基、C1-C10-烷氧基、C1-C10-烷基氨基、二-(C1-C10-烷基)氨基、C3-C10-链烯基氨基、二-(C3-C10-链烯基)-氨基,它们各任选被相同或不同的卤素单或多取代,或优选代表苯基或苄基,它们各任选被来自由卤素、C1-C4-烷基、C1-C4-烷氧基、C1-C4-卤代烷基、硝基和氰基组成的这组相同或不同的取代基单或多取代。
X
特别优选代表氟、氯、溴、C1-C4-烷基、C2-C4-链烯基、C1-C4-烷氧基、C2-C4-链烯氧基、C1-C4-烷硫基、C1-C4-烷基亚磺酰基、C1-C4-烷基磺酰基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、C2-C4-卤代链烯氧基、硝基、氰基或特别优选代表均可任选被氟-、氯-、溴-、C1-C4-烷基-、C1-C4-烷氧基-、C1-C2-卤代烷基-、C1-C2-卤代烷氧基-、硝基-或氰基-取代的苯基、苯氧基、苯硫基、苄氧基或苄硫基。
Y
特别优选代表氢、氟、氯、溴、C1-C4-烷基、C2-C4-链烯基、C1-C4-烷氧基、C2-C4-链烯氧基、C1-C4-烷硫基、C1-C4-烷基亚磺酰基、C1-C4-烷基磺酰基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、C2-C4-卤代链烯氧基、硝基或氰基。
Z
特别优选代表氟、氯、溴、C1-C4-烷基、C2-C4-链烯基、C1-C4-烷氧基、C2-C4-链烯氧基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、C2-C4-卤代链烯氧基、硝基或氰基。
A和Q一起特别优选代表C1-C5-烷二基或C2-C5-烯二基,它们任选被来自由下列这组基团组成的相同或不同取代基单或二取代:由氟、氯、溴、羟基、巯基,和由C1-C8-烷基、C1-C4-烷氧基、C1-C4-烷硫基、C5-C7-环烷基或苯基,它们各任选被来自由氟和氯组成的相同或不同的取代基单至五取代,上述C1-C5-烷二基或C2-C5-烯二基还可以含有下列基团之一: 或
或由C1-C2-烷二基基团桥接。
B和B’相互独立地各特别优选代表氢、氟、氯或C1-C4-烷基或一起特别优选代表均可任选被C1-C4-烷基取代的C1-C5-烷二基或C2-C4-烯二基。
E(f)或
其中
E代表金属离子等价物或铵离子,
L代表氧或硫,和
M代表氧或硫。
R1特别优选代表C1-C16-烷基、C2-C8-链烯基、C1-C6-烷氧基-C1-C6-烷基、C1-C6-烷硫基-C1-C6-烷基、多-C1-C6-烷氧基-C1-C6-烷基,它们各任选被相同或不同的氟和氯单至九取代,或特别优选代表C3-C7-环烷基,它任选被来自由氟、氯、C1-C4-烷基和C1-C4-烷氧基组成的这组相同或不同的取代基单至三取代且其中一或二个不直接相邻的亚甲基基团可以选由氧和/或硫原子代替,
特别优选代表苯基,它任选被来自由氟、氯、溴、硝基、氰基、C1-C4-烷基、C1-C4-烷氧基、C1-C3-卤代烷基和C1-C3-卤代烷氧基组成的这组相同或不同的取代基单至三取代,
特别优选代表苯基-C1-C4-烷基,它任选被来自由氟、氯、溴、C1-C4-烷基、C1-C4-烷氧基、C1-C3-卤代烷基和C1-C3-卤代烷氧基组成的这组相同或不同的取代基单至三取代,
特别优选代表呋喃基、噻吩基、吡啶基、嘧啶基、噻唑基或吡唑基,它们各任选被来自由氟、氯、溴和和C1-C4-烷基组成的这组相同或不同的取代基单或二取代,
特别优选代表苯氧基-C1-C5-烷基,它任选被来自由氟、氯和C1-C4-烷基组成的这组相同或不同的取代基单至三取代,或
特别优选代表吡啶氧基-C1-C6-烷基、嘧啶氧基-C1-C6-烷基或噻唑氧基-C1-C6-烷基,它们各任选被来自由氟、氯、氨基和C1-C4-烷基组成的这组相同或不同的取代基单或二取代。
R2特别优选代表C1-C16-烷基、C2-C8-链烯基、C1-C6-烷氧基-C2-C6-烷基或多-C1-C6-烷氧基-C2-C6-烷基,它们各任选被来自由氟和氯组成的这组相同或不同取代基单至七多取代,
特别优选代表C3-C6-环烷基,它任选被来自由氟、氯、C1-C4-烷基和C1-C4-烷氧基组成的这组相同或不同的取代基单至三取代,
特别优选代表苯基或苄基,它们各任选被来自由氟、氯、溴、硝基、氰基、C1-C4-烷基、C1-C4-烷氧基、C1-C2-卤代烷氧基或C1-C2-卤代烷基组成的这组相同或不同的取代基单至三取代。
R3特别优选代表C1-C9-烷基,它任选被来自由氟和氯组成的这组相同或不同的取代基单至五取代,或特别优选代表苯基或苯基-C1-C2-烷基,它们各任选被来自由氟、氯、溴、C1-C4-烷基、C1-C4-烷氧基、C1-C2-卤代烷基、C1-C2-卤代烷氧基、氰基和硝基组成的这组相同或不同的取代基单至三取代。
R4和R5相互独立地各特别优选代表C1-C6-烷基、C1-C6-烷氧基、C1-C6-烷基氨基、二-(C1-C6-烷基)氨基、C1-C6-烷硫基、C3-C4-烯硫基、C3-C6-环烷基硫基,它们各任选被来自由氟和氯组成的这组相同或不同的取代基单至五取代,或特别优选代表苯基、苯氧基或苯硫基,它们各任选被来自由氟、氯、溴、硝基、氰基、Cx-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-烷基和C1-C3-卤代烷基组成的这组相同或不同的取代基单至三取代。
R6特别优选代表氢,特别优选代表C1-C8-烷基、C3-C6-烯基、C1-C6-烷氧基-C2-C6-烷基,它们各任选被选自氟和氯组成的这组相同或不同的取代基单至五取代,特别优选代表C3-C8-环烷基,它任选被来自由氟、氯、C1-C4-烷基、C1-C4-烷氧基、C1-C2-卤代烷基和C1-C2-卤代烷氧基组成的这组相同或不同的取代基单至三取代,特别优选代表苯基,该苯基任选被来自由氟、氯、溴、C1-C2-卤代烷基、C1-C5-烷基、C1-C2-卤代烷氧基和C1-C5-烷氧基组成的这组相同或不同的取代基单至三取代,或特别优选代表苄基,该苄基任选被来自由氟、氯、溴、C1-C5-烷基、C1-C2-卤代烷基、C1-C2-卤代烷氧基和C1-C5-烷氧基组成的这组相同或不同的取代基单至三取代,
R7特别优选代表氢或特别优选代表C1-C8-烷基或C3-C8-烯基,它们各任选被来自由氟和氯组成的这组相同或不同的取代基单至五取代,或
R6和R7特别优选与连接的N原子结合,形成任选含氧或硫的且任选C1-C4-烷基取代的4-至7-元环。
R8和R9相互独立地各特别优选代表氢,C1-C4-烷基,它任选被来自由氟和氯组成的这组相同或不同的取代基单至五取代,或特别优选代表苯基,它任选被来自由氟、氯、C1-C4-烷基、C1-C4-烷氧基、C1-C2-卤代烷基、C1-C2-卤代烷氧基、硝基和氰基组成的这组相同或不同的取代基单至三取代,
或一起特别优选代表C2-C5-烷二基,该烷二基任选被来自由氟、氯、C1-C4-烷基、C1-C4-烷氧基和C1-C2-卤代烷基组成的这组相同或不同的取代基单至三取代,和
R10和R11相互独立地各特别优选代表C1-C8-烷基、C2-C8-链烯基、C1-C8-烷氧基、C1-C8-烷基氨基、C3-C8-链烯基氨基、二-(C1-C8-烷基)氨基或二-(C3-C8-链烯基)-氨基,它们各任选被来自由氟和氯组成的这组相同或不同的取代基单至五取代。
X
非常特别优选代表氟、氯、溴、甲基、乙基、丙基、异丙基、乙烯基、1-丙烯基、甲氧基、乙氧基、丙氧基、异丙氧基、烯丙氧基、甲代烯丙氧基、三氟甲基、二氟甲氧基、三氟甲氧基、三氟乙氧基、甲硫基、甲基亚磺酰基、甲基磺酰基、硝基、氰基,或非常特别优选代表均可由氟-、氯-、溴-、甲基-、乙基-、丙基-、异丙基-、叔丁基-、甲氧基-、乙氧基-、丙氧基-、叔丁氧基-、三氟甲基-、三氟甲氧基-、硝基-或氰基-取代的苯基、苯氧基、苯硫基、苄氧基或苄硫基。
Y
非常特别优选代表氢、氟、氯、溴、甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、乙烯基、1-丙烯基、甲氧基、乙氧基、丙氧基、异丙氧基、烯丙氧基、甲代烯丙氧基、三氟甲基、甲硫基、甲基亚磺酰基、甲基磺酰基、二氟甲氧基、三氟甲氧基、三氟乙氧基、硝基或氰基。
Z
非常特别优选代表氟、氯、溴、甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、乙烯基、1-丙烯基、甲氧基、乙氧基、丙氧基、异丙氧基、烯丙氧基、甲代烯丙氧基、三氟甲基、二氟甲氧基、三氟甲氧基、三氟乙氧基、硝基或氰基。
A和Q一起非常特别优选代表C1-C4-烷二基或C2-C4-烯二基,它们各任选被来自由下列这组基团组成的相同或不同的取代基单或二取代:氟、氯、羟基、C1-C6-烷基和C1-C2-烷氧基,后二者任选被来自由氟和氯组成的这组相同或不同的取代基单至三取代。
B和B’相互独立地各非常特别优选代表氢、甲基或乙基,
G非常特别优选代表氢(a)或下列基团之一:
其中
E代表金属离子等价物或铵离子,
L代表氧或硫,和
M代表氧或硫,
R1非常特别优选代表C1-C14-烷基、C2-C6-链烯基、C1-C4-烷氧基-C1-C6-烷基、C1-C4-烷硫基-C1-C6-烷基、多-C1-C4-烷氧基-C1-C4-烷基,它们各任选被来自由氟和氯组成的这组相同或不同的取代基单至五取代,或非常特别优选代表C3-C6-环烷基,它任选被来自由氟、氯、甲基、乙基、甲氧基和乙氧基组成的这组相同或不同的取代基单或二取代,且其中的一或二个不直接相邻的亚甲基基团可以由氧和/或硫原子代替,
非常特别优选苯基,该苯基任选被来自由氟、氯、溴、甲基、乙基、丙基、异丙基、甲氧基、乙氧基、三氟甲基、三氟甲氧基、氰基和硝基组成的这组相同或不同的取代基单或二取代,
非常特别优选代表苄基,该苄基任选被来自由氟、氯、溴、甲基、乙基、丙基、异丙基、甲氧基、乙氧基、三氟甲基和三氟甲氧基组成的这组相同或不同的取代基单或二取代,
非常特别优选代表噻吩基、呋喃基或吡啶基,它们各任选被来自由氟、氯、溴、甲基和乙基组成的这组相同或不同的取代基单或二取代,
非常特别优选代表苯氧基-C1-C4-烷氧基,它任选被来自由氟、氯、甲基和乙基组成的这组相同或不同的取代基单或二取代,或
非常特别优选代表吡啶氧基-C1-C4-烷基、嘧啶氧基-C1-C4-烷基或噻唑氧基-C1-C4-烷基,它们各任选被来自由氟、氯、氨基、甲基和乙基组成的这组相同或不同的取代基单或二取代。
R2非常特别优选代表C1-C14-烷基、C2-C6-链烯基、C1-C4-烷氧基-C2-C6-烷基或多-C1-C4-烷氧基-C2-C6-烷基,它们各任选被来自由氟和氯组成的这组相同或不同的取代基单至五取代,非常特别优选代表C3-C6-环烷基,它任选被来自由氟、氯、甲基、乙基、甲氧基和乙氧基组成的这组相同或不同的取代基单至三取代,
或非常特别优选代表苯基或苄基,它们各任选被来自由氟、氯、硝基、氰基、甲基、乙基、丙基、异丙基、甲氧基、乙氧基、三氟甲氧基和三氟甲基组成的这组相同或不同的取代基单或二取代。
R3非常特别优选代表C1-C6-烷基,它任选被来自由氟和氯组成的相同或不同的取代基单至三取代,或非常特别优选代表苯基或苄基,它们各任选由氟、氯、溴、甲基、乙基、甲氧基、乙氧基、三氟甲基、三氟甲氧基、氰基或硝基单或二取代。
R4和R5相互独立地各非常特别优选代表C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷氨基、二-(C1-C4-烷基)氨基、C1-C4-烷硫基,它们各任选被由氟和氯组成的这组相同或不同的取代基单至三取代,或非常特别优选代表苯基、苯氧基或苯硫基,它们各任选被来自由氟、氯、溴、硝基、氰基、C1-C2-烷氧基、三氟甲氧基、C1-C2-烷硫基、三氟甲基或C1-C3-烷基组成的这组相同的或不同的取代基单或二取代。
R6非常特别优选代表氢,非常特别优选代表C1-C6-烷基、C1-C6-烷氧基-C2-C4-烷基,它们各任选被来自由氟和氯组成的这组相同或不同的取代基单至三取代,非常特别优选代表C3-C6-环烷基,它任选被来自由氟、氯、甲基、甲氧基、三氟甲基和三氟甲氧基组成的这组相同或不同的取代基单或二取代,非常特别优选代表苯基,该苯基任选被来自由氟、氯、三氟甲基、C1-C4-烷基、三氟甲氧基和C1-C4-烷氧基组成的这组相同或不同的取代基单或二取代,或非常特别优选代表苄基,该苄基任选被来自由氟、氯、C1-C4-烷基、三氟甲基、三氟甲氧基和C1-C4-烷氧基组成的这组相同或不同的取代基单或二取代。
R7非常特别优选代表氢,非常特别优选代表C1-C6-烷基或C3-C6-链烯基,它们各任选被来自由氟和氯组成的这组相同或不同的取代基单至三取代,
R6和R7非常特别优选与连接的N-原子一起结合,形成任选含氧或硫的、任选甲基取代的5-至7-元环。
在每一种情况下,X、Y和Z不可同时代表甲基。
一般性或在优选范围中提到的基团的上述定义或说明可以按需要相互组合,这就是说,包括各范围间和优选范围间的组合。它们适用于终产物且相应地适应于前体或中间体。
上面提到的定义中,饱和或不饱和烃基,在每一情况下,包括与杂原子组合(例如烷氧基或链烯硫基),只要可能,均可以是直链或支链。
根据本发明,式(I)化合物优选的是其中存在上文提到的优选含意之组合的化合物。
根据本发明,式(I)化合物特别优选的是其中存在上文提到的特别优选含意之组合的化合物。
根据本发明,式(I)化合物非常特别优选的是其中存在上文提到的非常特别优选含意之组合的化合物。
除非另有说明,取代的基团可以被相同或不同的可能的取代基单或多取代。
除了在制备实施例提到的化合物外,可以具体提到下列(Ia)的2-苯基-取代的3-羟基-Δ2-环戊烯酮衍生物:
表1
-(CH2)2-CHOCH3- | H | H | Br | CH3 | CH3 |
-CH2-CHCH3-CH2- | H | H | Br | CH3 | CH3 |
-CH2-CHOCH3-CH2- | H | H | Br | CH3 | CH3 |
-CH2-CHCH3-CHCH3- | H | H | Br | CH3 | CH3 |
-CH2-CHOCH3-CHOCH3- | H | H | Br | CH3 | CH3 |
-(CH2)4- | H | H | Br | CH3 | CH3 |
-(CH2)3-CHCH3- | H | H | Br | CH3 | CH3 |
-(CH2)3-CHOCH3- | H | H | Br | CH3 | CH3 |
表2
A、Q、B和B’各如表1中所定义
X=CH3 Y=Br Z=CH3
表3
A、Q、B和B’各如表1中所定义
X=C2H5 Y=Br Z=CH3
表4
A、Q、B和B’各如表1中所定义
X=Cl Y=CH3 Z=CH3
表5
A、Q、B和B’各如表1中所定义
X=CH3 Y=Cl Z=CH3
表6
A、Q、B和B’各如表1中所定义
X=OCH3 Y=CH3 Z=CH3
表7
A、Q、B和B’各如表1中所定义
X=CH3 Y=OCH3 Z=CH3
表8
A、Q、B和B’各如表1中所定义
X=OCH3 Y=H Z=CH3
表9
A、Q、B和B’各如表1中所定义
X=Cl Y=H Z=CH3
表10
A、Q、B和B’各如表1中所定义
X=Cl Y=H Z=Cl
表11
A、Q、B和B’各如表1中所定义
X=CH3 Y=H Z=CH3
表12
A、Q、B和B’各如表1中所定义
X=Cl Y=Cl Z=CH3
表13
A、Q、B和B’各如表1中所定义
X=Cl Y=CH3 Z=Cl
表14
A、Q、B和B’各如表1中所定义
X=Cl Y=H Z=OCH3
表15
A、Q、B和B’各如表1中所定义
X=CH3 Y=CN Z=CH3
表16
A、Q、B和B’各如表1中所定义
X=CN Y=CH3 Z=CH3
如果在方法(E)中,用2-(4-溴-2,6-二甲基苯基)-4,5-(3-甲氧基)-四亚甲基-3-羟基-2-环戊烯-1-酮和甲磺酰氯作为起始物,则此反应之过程可以由下列反应式代表:
如果在方法(F)中,用2-(4-溴-2,6-二甲基苯基)-4,5-(4-甲基)-四亚甲基-3-羟基-2-环戊烯-1-酮和氯甲硫代磷酸(2,2,2-三氟乙基)酯作为起始物,则此反应之过程可以由下列反应式代表:
如果在方法(Hβ)中,用2-(4-甲氧基-2,6-二甲基苯基)-4,5-四亚甲基-3-羟基-2-环戊烯-1-酮和二甲基氨甲酰氯作为起始物,则此反应之过程可以由下列反应式代表:
其中
A、B、B’、Q、X、Y、Z和R12各如上所定义,
它们可以通过原则上已知的方法制备。式(II)的5-芳基-4-酮羧酸酯例如通过将式(XIV)的5-芳基-4-酮羧酸酯化而获得(参见例如Organikum,第15版,柏林,1977,第499页)
其中
A、B、B’、Q、X、Y和Z各如上所定义。
式(XIV)的5-芳基-4-酮羧酸是新的;但它们可以用原则上已知的方法制备。
其中
A、B、B’、Q、X、Y和Z各如上所定义。
其中
A、B、B’和Q各如上所定义,
其中
X、Y和Z各如上所定义,
Me代表单或二价金属离子(例如锂或镁),
Hal代表氯或溴
且
l代表数字0或1。
一些化合物(XV)和(XVI)是已知的和/或可以通过已知的方法用简单的方式制备(参见,例如Organikum,第15版,柏林,1977,第525、526和623页)。
此外,式(XIV)的5-芳基-4-酮羧酸可以如下获得:使式(XVII)的取代的2-苯基-3-氧代-己二酸酯脱羧基化,
其中
A、B、B’、Q、X、Y和Z各如上所定义,
其中
A、B、B’、Q、X、Y和Z各如上所定义,且
R12和R12’各代表烷基(优选C1-C6-烷基),
如果适当的话在稀释剂存在下,且如果适当的话在碱或酸存在下进行反应(参见,例如Organikum,第15版,柏林,1977,第519至521页)。
其中
A、B、B’、Q、X、Y、Z、R12和R12’各如上所定义,且
其中
A、B、B’、Q和R12各如上所定义,且
其中
A、B、B’和Q各如上所定义,
其中
X、Y、Z和R12’各如上所定义,
反应在稀释剂存在下和在碱存在下进行(参见,例如M.S.Chambers,E.J.Thomas,D.J.Williams,J.Chem.Soc.Chem.Commun.,(1987),1228)。
一些式(XVIII)和(XIX)化合物是已知的和/或它们可以用已知方法制备。
在每一种情况下,本发明式(Ib)至(Ig)的活性化合物由式(Ia)化合物为原料制备,而式(Ia)化合物可由本发明方法(A)获得。它们是制备式(Ib)至(Ig)化合物的重要的中间体。
此外,进行本发明方法(B)、(C)、(D)、(E)、(F)、(G)和(H)所需的起始物——式(III)酰基卤、式(IV)的羧酸酐、式(V)的氯甲酸酯或氯甲酸硫醇酯、式(VI)的氯单硫代甲酸酯或氯二硫代甲酸酯、式(VII)的烷基卤、式(VIII)的磺酰氯、式(IX)磷化合物和式(X)和(XI)的金属化合物或胺和式(XII)的异氰酸酯和式(XIII)的氨基甲酰氯或硫代氨基甲酰氯类是有机或无机化学的一般已知化合物。
方法(A)的特征在于,使式(II)化合物(其中A、B、B’、Q、X、Y、Z和R12各如上所定义)在碱存在下进行分子内缩合。
适合于本发明方法(A)的稀释剂是对反应参与者是惰性的所有有机溶剂。可优选利用的是烃,如甲苯和二甲苯,还有醚类,如二丁基醚、四氢呋喃、二噁烷、乙二醇二甲基醚和二乙二醇二甲醚,还可以是极性溶剂,如二甲基亚砜、环丁砜、二甲基甲酰胺和N-甲基-吡咯烷酮。此外,也可以使用醇类如甲醇、乙醇、丙醇、异丙醇、丁醇、异丁醇、叔丁醇。
适合于进行本发明方法(A)的碱(脱质子剂)是所有的常规质子受体。
可优选利用的是碱金属或碱土金属氧化物、氢氧化物和碳酸盐,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,它们也可以在相转移催化剂存在下被采用。相转移催化剂如三乙基苄基氯化铵、四丁基溴化铵、Adogen 464(甲基三烷基(C8-C10-)氯化铵)或TDA1(三-(甲氧基乙氧基乙基)胺)。也可以使用碱金属如钠和钾。再者,可以采用碱金属和碱土金属氨化物和氢化物,如氨化钠、氢化钠和氢化钙,以及碱金属醇盐如甲醇钠、乙醇钠和叔丁醇钾。
当进行本发明方法(A)时,反应温度可以在相对宽的范围内变化。通常,此反应是在0℃至250℃间,优选50℃至150℃间的温度下进行。
本发明方法(A)通常是在常压下进行。
当进行本发明方法(A)时,通常采用大致等摩尔量的式(II)的反应组分和脱质子碱。然而,也可以相对大的过量使用一种组分或另一种(至多3摩尔)。
方法(Bα)的特征在于,使式(Ia)化合物与式(III)的羧酰卤反应。
适合于本发明方法(Bα)的稀释剂是对酰基卤惰性的所有溶剂。可优选利用的是烃,如汽油、苯、甲苯、二甲苯和四氢化萘,还有卤代烃,如二氯甲烷、氯仿、四氯化碳,氯苯和邻二氯苯,此外还有酮类,如丙酮和甲基异丙基酮,还有醚类,如乙醚、四氢呋喃和二噁烷,以及羧酸酯类,如乙酸乙酯,和强极性溶剂,如二甲基亚砜和环丁砜。如果酰基卤的水解稳定性许可,此反应也可以在水存在下进行。
适合于本发明方法(Bα)的酸结合剂是所有的常规酸受体。可优选利用的是叔胺类,如三乙胺、吡啶、二氮杂二环辛烷(DABCO)、二氮杂二环十一碳烯(DBU)、二氮杂二环壬烯(DBN)、Hünig碱和N,N-二甲基苯胺,还有碱土金属氧化物,如氧化镁和氧化钙,以及碱金属碳酸盐和碱土金属碳酸盐,如碳酸钠、碳酸钾和碳酸钙。
在本发明方法(Bα)中,反应温度可以在相对宽的范围内变化。通常,反应可以在-20℃至+150℃间,优选在0℃至100℃间的温度下进行。
当进行本发明方法(Bα)时,通常采用大致等摩尔量的式(Ia)起始物和式(III)的羧酰卤。然而,也可以相对大的过量使用羧酰卤(至多5摩尔)。后处理是用常规方法进行的。
方法(Bβ)的特征在于,使式(Ia)化合物与式(IV)的羧酸酐反应。
优选用于本发明方法(Bβ)中的稀释剂是采用酰基卤时同样是优选的那些。再则,还可以过量采用羧酸酐,用作稀释剂。
在本发明方法(Bβ)中,反应温度可以在较宽的范围内变化。通常,反应可以在-20℃至+150℃间,优选在0℃至100℃间的温度下进行。
当进行本发明方法(Bβ)时,通常采用大致等摩尔量的式(Ia)起始物和式(IV)的羧酸酐。然而,也可以相对大的过量使用羧酸酐(至多5摩尔)。后处理是用常规方法进行的。
通常,使用这样一步骤,其中通过蒸馏或通过用有机溶剂或用水洗涤脱出稀释剂和过量的羧酸酐和所得的羧酸。
方法(C)的特征在于,使式(Ia)化合物与式(V)的氯甲酸酯或氯甲酸硫醇酯反应。
适合于本发明方法(C)的酸结合剂是所有的常规酸受体。可优选利用的是叔胺类,如三乙胺、吡啶、DABCO、DBU、DBN、Hünig碱和N,N-二甲基苯胺,还有碱土金属氧化物,如氧化镁和氧化钙,以及碱金属碳酸盐和碱土金属碳酸盐,如碳酸钠、碳酸钾和碳酸钙。
适合于本发明方法(C)的稀释剂是对起始物惰性的所有溶剂。可优选利用的是烃,如汽油、苯、甲苯、二甲苯和四氢化萘,还有卤代烃,如二氯甲烷、氯仿、四氯化碳,氯苯和邻二氯苯,此外还有酮类,如丙酮和甲基异丙基酮,还有醚类,如乙醚、甲基叔丁基醚、四氢呋喃和二噁烷,以及羧酸酯类,如乙酸乙酯,和强极性溶剂,如二甲基亚砜和环丁砜。
在本发明方法(C)中,反应温度可以在相对宽的范围内变化。如果反应在稀释剂和酸结合剂存在下,反应温度通常是在-20℃至+100℃间,优选在0℃至50℃间。
本发明方法(C)通常是在常压下进行。
进行本发明方法(C)时,通常采用大致等摩尔量的式(Ia)起始物和式(V)的相应的氯甲酸酯或氯甲酸硫醇酯。然而,也可以相对大地过量采用一种组分或另一种组分(至多2摩尔)。后处理是用常规方法进行的。通常使用这样一步骤,脱出其中沉淀出的盐,并将留下的反应混合物通过汽提掉稀释剂而浓缩。
在制备方法(Dα)中,使每摩尔的式(Ia)起始物与约1摩尔的式(VI)氯单硫代甲酸酯或氯二硫代甲酸酯在0至120℃,优选在20至60℃下反应。
如果适当的话,可以加入的稀释剂是所有的惰性有机溶剂,如卤代烃、醚类、酰胺类、醇类、腈类、砜类和亚砜类。
优选的是使用乙腈、二甲基亚砜、甲基叔丁基醚、四氢呋喃、二甲基甲酰胺、乙酸乙酯或二氯甲烷。
如果,在优选的实施方案中,式(Ia)化合物的烯醇盐是通过加入强脱质子剂(如氢化钠和叔丁醇钾)而制备的,则可以省去另外加入酸结合剂。
如果使用酸结合剂,则常规的无机或有机碱是适合的。可以例举的有氢氧化钠、碳酸钠、碳酸钾、吡啶和三乙胺。
此反应可以在常压下或在加压下进行。优选的是在常压下进行。后处理是根据常规方法进行的。
在制备方法(Dβ)中,每摩尔的式(II)起始物加入等摩尔量或过量的二硫化碳。此反应优选是在0至50℃,且特别是在20至30℃下进行的。
适合于方法(Dβ)的碱是所有的常规质子受体。可优选利用的是碱金属氢化物、碱金属醇盐、碱金属或碱土金属碳酸盐或碳酸氢盐或氮碱。实例包括氢化钠、甲醇钠、氢氧化钠、氢氧化钙、碳酸钾、碳酸氢钠、三乙胺、二苄基胺、二异丙胺、吡啶、喹啉、二氮杂二环辛烷(DABCO)、二氮杂二环壬烯(DBU)和二氮杂二环十一碳烯(DBU)。
在此方法中适合于作为稀释剂使用的是所有的常规溶剂。
可优选利用的是芳烃,如苯或甲苯,醇类,如甲醇、乙醇、异丙醇或乙二醇,腈类,如乙腈,醚类,如四氢呋喃或二噁烷,酰胺类,如二甲基甲酰胺,或其它极性溶剂,如二甲基亚砜或环丁砜。
在许多情况下,有利地是先由式(Ia)化合物通过添加脱质子剂(如叔丁醇钾或氢化钠)制备出相应的盐。使式(Ia)化合物与二硫化碳反应,直到中间体形成结束,例如在室温下搅拌几小时后。
与式(VII)烷基卤的进一步反应优选是在0至70℃,且特别是在20至50℃下进行的。采用至少等摩尔量的烷基卤。
此反应是在常压下或在加压下进行的,优选是在常压下。
后处理同样是用常规方法进行的。
在制备方法(E)中,在0至150℃下,优选在20至70℃下,每摩尔式(Ia)起始物采用约1摩尔的式(VIII)磺酰氯。
如果适当的话,可以加入的稀释剂是所有的惰性有机溶剂,如卤代烃、醚类、酰胺类、羧酸酯类、腈类、砜类或亚砜类。
优选的是使用乙腈、二甲基亚砜、乙酸乙酯、甲基叔丁基醚、四氢呋喃、二甲基甲酰胺或二氯甲烷。
如果,在优选的实施方案中,式(Ia)化合物的烯醇盐是通过加入强脱质子剂(如氢化钠或叔丁醇钾)而制备的,则可以省去另外加入酸结合剂。
如果使用酸结合剂,则常规的无机或有机碱是适合的。可以例举的有氢氧化钠、碳酸钠、碳酸钾和吡啶。
此反应可以在常压下或在加压下进行。优选的是在常压下进行。后处理是根据常规方法进行的。
如果适当的话,制备方法(E)可以在相转移条件下进行(W.J.Spillane等;J.Chem.Soc.,Perkin Trans I,(3)677-9(1982))。在此情况下,在0至150℃,优选在20至70℃下,每摩尔的式(Ia)起始物采用0.3至5摩尔,优选1摩尔的式(VIII)磺酰氯。
适合的相转移催化剂是所有的季铵盐,优选四辛基溴化铵和苄基三乙基氯化铵。在此情况下,所有的非极性惰性溶剂均可作为有机溶剂,优选的是使用苯或甲苯。
在制备方法(F)中,在-40℃至150℃间,优选在-10至110℃间的温度下,每摩尔的式(Ia)化合物采用1至2,优选1至1.3摩尔的式(IX)磷化合物,获得式(Ie)化合物。
如果适当的话,可以加入的稀释剂是所有的惰性有机溶剂如卤代烃、醚类、酰胺类、腈类、羧酸酯类、砜类、亚砜类等。
优选的是使用乙腈、二甲基亚砜、乙酸乙酯、甲基叔丁基醚、四氢呋喃、二甲基甲酰胺或二氯甲烷。
如果适当的话可以加入的酸结合剂是所有的常规无机或有机碱,如氢氧化物、氨基化物类、碳酸盐。实例包括氢氧化钠、碳酸钠、碳酸钾、吡啶、三乙胺或DABCO。
反应可以在常压下或加压下进行,优选是在常压下进行。后处理是用有机化学的常规方法进行的。所得的终产物优选通过结晶法、色谱纯化法或通过所谓的“初始蒸馏”(即减压去除挥发性组分)来纯化。
方法(G)的特征在于,使式(Ia)化合物与式(X)的金属化合物或式(XI)的胺反应。
对于本发明的此方法优选的稀释剂是醚类,如四氢呋喃、二噁烷、乙醚,或是醇类,如甲醇、乙醇、异丙醇,且也可以是水。本发明的方法(G)通常是在常压下进行的。反应温度通常是在-20℃至100℃间,优选0℃至50℃。
进行本发明方法(H)时,通常以大致等摩尔量使用式(Ia)和(XII)或(XIII)起始物。然而,也可以相对大地过量使用一或另一种组分(至多2摩尔)。通常,使用这样一步骤,其中通过汽提掉稀释剂来浓缩反应混合物。
在制备方法(Hα)中,在0至100℃下,优选在20至50℃下,每摩尔式(Ia)起始物优选采用约1摩尔的式(XII)异氰酸酯或异硫氰酸酯。
如果适当的话,可以加入的稀释剂是所有的惰性有机溶剂,如烃、卤代烃、醚类、羧酸酯类、酰胺类、腈类、砜类或亚砜类。
优选的是使用甲苯、二氯甲烷、四氢呋喃、乙酸乙酯、二甲基甲酰胺或二甲基亚砜。
如果适当的话,可以加入催化剂以加速此反应。可以非常有利地采用的催化剂是有机锡化合物,如二丁基锡二月桂酸酯。
此反应优选在常压下进行。
在制备方法(Hβ)中,在0℃至150℃间,优选在20至70℃间的温度下,每摩尔的式(Ia)化合物采用约1摩尔的式(XIII)氨基甲酰氯或硫代氨基甲酰氯。
如果适当的话,可以加入的稀释剂是所有的惰性有机溶剂如卤代烃、羧酸酯类、醚类、酰胺类、腈类、砜类或亚砜类等。
优选的是使用乙腈、乙酸乙酯、二甲基亚砜、甲基叔丁基醚、四氢呋喃、二甲基甲酰胺或二氯甲烷。
如果,在优选的实施方案中,式(Ia)化合物的烯醇盐是通过加入强脱质子剂(如氢化钠和叔丁醇钾)而制备的,则可以省去另外加入酸结合剂。
如果使用酸结合剂,则所有的常规无机或有机碱都是适合物。可以例举的实例有氢氧化钠或碳酸钠、碳酸钾、吡啶、三乙胺或DABCO。
反应可以在常压下或加压下进行,优选是在常压下进行。后处理是用有机化学的常规方法进行的。
本发明活性化合物适合防治动物害虫,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的昆虫、蜱螨和线虫。它们优选被用作作物保护剂。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,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(Blatella germanica)、家蟋蟀(Acheta domesticus)、蝼蛄属(Gryllotalpa spp.)、热带飞蝗(Locusta migratoriamigratorioides)、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_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)、美核桃根瘤蚜(Phylloxera vaststrix)、瘿绵蚜属(Pemphigus spp.)、麦长管蚜(Macrosiphum avenae)、瘤额蚜属(Myzus spp.)、忽布疣蚜(Phorodon humili)、禾谷缢管蚜(Rhopalosiphum padi)、微叶蝉属(Empoasca spp.)、钝鼻叶蝉(Euscelis bilobatus)、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(Nilaparvatalugens)、红肾园盾蚧(Aonidiella aurantii)、夹竹桃园蚧(Aspidiotus hederae)、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(Hyponomeutapadella)、小菜蛾(Plutella maculipennis)、天幕毛虫(Malacosoma neustria)、黄毒蛾(Euproctis chrysorrhoea)、毒蛾属(Lymantria spp.)、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(Spodotera 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)、Bruchidius obtectus、大豆象(Acanthoscelides 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(Atomariaspp.)、锯谷盗(Oryzaephilus surinamensis)、花象甲属(Anthonomus spp.)、米象属(Sitophilus spp.)、葡萄黑耳喙象(Otiorrhynchus sulcatus)、香蕉根象甲(Cosmopolitessordidus)、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(At tagenus spp.)、粉蠹属(Lyctus spp.)、油菜花露尾甲(Meligethes aeneus)、蛛甲属(Ptinus spp.)、金黄蛛甲(Niptushololeucus)、裸蛛甲(Gibbium psylloides)、拟谷盗属(Triboliumspp.)、黄粉虫(Tenebrio molitor)、叩头虫属(Agriotes spp.)、宽胸叩头虫属(Conoderus spp.)、西方五月鳃角金龟(Melolonthamelolontha)、马铃薯鳃角金龟(Amphimallon sostitialis)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_瘿螨(Eriophyes ribis)、柑桔锈螨(Phyllocoptruta oleivora)、牛蜱属(Boophilus spp.)、扇头蜱属(Rhipicephalus spp.)、花蜱属(Amblyomma spp.)、玻眼蜱属(Hyalomma spp.)、硬蜱属(Ixodes spp.)、瘙螨属(Psoroptesspp.)、皮螨属(Chorioptes spp.)、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(Pratylenchus spp.)、毕肖穿孔线虫(Radopholus similis)、Ditylenchus dipsaci、Tylenchulus semipenetrans、异皮线虫(Heterodera spp.)、囊线虫(Globodera spp.)、根结线虫(Meloidogyne spp.)、滑刃线虫(Aphelechoides spp.)、Longidorus spp.、剑线虫(Xiphinemaspp.)和髦根线虫(Trichodorus spp.)。
特别是,本发明式(I)化合物具有优异的杀虫活性。例如,它们对辣根猿叶甲(Phaedon cochleariae)毛虫和小菜蛾(Plutellamaculipennis)幼虫具有强的活性。
本发明活性化合物可以用作脱叶剂、干燥剂、杀茎杆剂,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、母草属、春黄菊属、牛膝属、藜属、荨麻属、千里光属、苋属、马齿苋赂、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、焊菜属、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、野豌豆属、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、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、_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、草皮和牧场中的杂草,和选择性地防治一年生作物中的杂草。
本发明式(I)化合物特别适合于选择性地以芽前和芽后二种方式防治双子叶作物中的单子叶杂草。可以用它们来非常成功地防治例如棉花或甘蔗中的有害禾草。
活性化合物可以转化成常规的剂型,如溶液、乳剂、可湿性粉剂、悬浮剂、粉剂、喷粉剂、膏剂、水溶性粉剂、颗粒剂、悬浮乳剂、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。
这些型剂可以用已知的方式生产,例如,将活性化合物与填充剂,即液体溶剂和/或固体载体混合,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,也可以用例如有机溶剂作助溶剂。作为液体溶剂,适合的主要有: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,例如矿物油馏份、矿物和植物油,醇类,如丁醇或乙二醇以及其醚和酯,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;用于颗粒剂的固体载体适合的有: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粉状、颗粒或乳胶形式的羧甲基纤维素和天然和合成聚合物,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。可能的其他添加剂是矿物油和植物油。
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,和微量营养素如铁、锰、硼、铜、钴、钼和锌盐。
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%。
本发明活性化合物可以其商业上可行的制剂和由这些制剂制备的使用形式存在,所述的制剂为与如下的其它活性化合物的混合物:如杀虫剂、引诱剂、不育剂、杀细菌剂、杀螨剂、杀线虫剂、杀真菌剂、生长调节剂或除草剂。杀虫剂包括例如磷酸酯类、氨基甲酸酯类、羧酸酯类、氯代烃类、苯基脲类和由微生物生产的物质。
特别有利的混合物组分是例如下列:
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-甲酰苯胺;2,6-二氯-N-(4-三氟甲基苯甲基)苯甲酰胺;(E)-2-甲氧基亚氨基-N-甲基-2-(2-苯氧苯基)乙酰胺;8-羟基喹啉硫酸盐;(E)-2-{2-[6-(2-氰基-苯氧基)嘧啶-4-氧基]苯基}-3-甲氧基丙烯酸甲酯;(E)-甲氧基亚氨基[α-(邻甲苯氧基)-邻甲苯基]乙酸甲酯;2-苯基苯酚(OPP)、aldimorph、氨丙磷酸、敌菌灵、戊环唑、苯霜灵、碘萎灵、苯菌灵、乐杀螨、联苯、双苯三唑醇、灭瘟素、糠菌唑、磺酸丁嘧啶、丁赛特、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、乙菌利、硫杂灵、霜脲氰、环唑醇、酯菌胺、防霉酚、苄氯三唑醇、抑菌灵、哒菌清、氯硝胺、乙霉威、噁醚唑、甲嘧醇、烯酰吗啉、烯唑醇、清螨普、二苯胺、吡菌硫、灭菌磷、二噻农、十二烷胍、腙菌酮、克菌散、环氧唑(epoxyconazole)、乙嘧啶、氯唑灵、双氯苯嘧啶、苯氰唑、呋菌胺、种衣酯、拌种咯、苯锈啶、丁苯吗啉、乙酸三苯基锡、三苯羟基锡、福美铁、嘧菌腙、氟啶胺、fludioxonil、氟氯菌核利、fluquinconazole、氟哇唑、磺菌胺、氟酰胺、粉唑醇、灭菌丹、乙磷铝、四氯苯酞、麦穗宁、呋霜灵、拌种胺、双胍辛、六氯苯、己唑醇、甲羟异恶唑、抑霉唑、酰胺唑、双胍辛醋酸盐、异稻瘟净、异菌脲、稻瘟灵、春日霉素、铜制剂(如氢氧化铜、环烷酸铜、氯氧化铜、硫酸铜、氧化铜、喹啉酮和波尔多混合物)、双代混剂、代森锰锌、代森锰、嘧菌胺、灭锈胺、甲霜灵、metconazole、磺菌威、担菌胺、代森联、噻菌胺、腈菌唑、福美镍、异丙消、氟苯嘧啶醇、甲呋酰胺、噁酰胺、oxamocarb、氧化萎锈灵、稻瘟酯、戊菌唑、戊菌隆、稻病磷、稻瘟酞、匹马菌素、哌啶宁、多氧霉素、烯丙异噻唑、咪鲜安、二甲菌核利、霜霉威、丙环唑、甲基代森锌、定菌磷、啶斑肟、pyrimethanil、咯喹酮、五氯硝基苯、硫磺和硫制剂、戊唑醇、酞枯酸、四氯硝基苯、氟醚唑、噻菌灵、噻菌腈、甲基托布津、福美双、甲基立枯灵、对甲抑菌灵、三唑酮、三唑醇、唑菌嗪、杨菌胺、三环唑、环吗啉、氟菌唑、嗪氨灵、triticonazole、稻纹散、乙烯菌核利、代森锌、福美锌。
杀细菌剂:
拌棉酚、防霉酚、氯定、福美镍、春日霉素、异噻菌酮、呋喃羧酸、土霉素、烯丙异噻唑、链霉素、酞枯酸、硫酸铜和其它铜制剂。
杀虫剂/杀螨剂/杀线虫剂:
齐墩螨素、AC 303 630、乙酰甲胺磷、氟酯菊酯、棉铃威、涕灭威、甲体氯氰菊酯、双甲脒、阿维螨素(avermectin)、AZ 60541、azadifachtin、乙基谷硫磷、谷硫磷、三唑锡、苏芸金杆菌、苯噁威、丙硫克百威、杀虫磺、乙体氟氯氰菊酯、联苯菊酯、丁苯威、溴醚菊酯(brofenprox)、溴硫磷、混戊威、噻嗪酮、丁酮威、丁基哒螨酮、硫线磷、西维因、克百威、三硫磷、丁硫克百威、巴丹、CGA157419、CGA 184 699、除线威、chlorethoxyfos、毒虫畏、定虫隆、氯甲硫磷、毒死蜱、甲基毒死蜱、顺式苄呋菊酯、三氟氯氰菊酯、四螨嗪、杀螟腈、乙氰菊酯、氟氯氰菊酯、氯氟氰菊酯、三环锡、氯氰菊酯、灭蝇胺、溴氰菊酯、甲基内吸磷、内吸磷、异吸磷II、杀螨隆、地亚农、氯线磷、敌敌畏、dicliphos、百治磷、乙硫磷、伏虫脲、乐果、甲基毒虫畏、二恶硫磷、乙拌磷、克瘟散、emamectin、高氰戊菊酯、除蚜威、乙硫磷、醚菊酯、丙线磷、乙嘧硫磷、克线磷、喹螨醚、螨完锡、杀螟硫磷、仲丁威、苯硫威、双氧威、甲氰菊酯、fenpyrad、唑螨酯、倍硫磷、氰戊菊酯、锐劲特(fipronil)、氟啶胺、氟螨脲、氟氰戊菊酯、氟虫脲、氟醚菊酯(flufenprox)、氟胺氰菊酯、地虫硫磷、安果、噻唑硫磷、溴醚菊酯(fubfenprox)、呋线威、六六六、庚虫磷、氟铃脲、噻螨酮、咪蚜胺、异稻瘟净、氯唑磷、异丙胺磷、异丙威、噁唑磷、伊维菌素、λ-三氟氯氰菊酯、lufenuron、马拉硫磷、灭蚜硫磷、速灭磷、倍硫磷亚砜、蜗牛敌、虫螨畏、甲胺磷、甲噻硫磷、甲硫威、灭多威、速灭威、米尔倍菌素、久效磷、moxidectin、二溴磷、NC 184、NI 25、nitenpyram、氧乐果、草肟威、砜吸硫磷、异砜磷、对硫磷、甲基对硫磷、氯菊酯、稻丰散、甲拌磷、伏杀硫磷、亚胺硫磷、磷胺、辛硫磷、抗蚜威、甲基嘧啶硫磷、嘧啶硫磷、丙溴磷、甲丙威、丙虫威、残杀威、低毒硫磷、发果、pymetrozin、吡唑硫磷、苯哒嗪硫磷、反灭菊酯、除虫菊酯、哒螨酮、pyrimidifen、蚊蝇醚、喹硫磷、RH 5992、水杨硫磷、硫线磷、施乐宝(silafluofen)、治螟磷、甲丙硫磷、米满(tebufenozid)、吡螨胺(tebufenpyrad)、特丁嘧啶硫磷、伏虫隆、七氟菊酯、双硫磷、叔丁威、特丁甲拌磷、杀虫畏、thiafenox、硫双灭多威、己酮肟威、甲基乙拌磷、喹线磷、苏芸金菌素、四溴菊酯、苯赛螨、三唑磷、triazuron、敌百虫、杀虫隆、trimethacarb、完灭硫磷、二甲威、二甲苯威、YI 5301/5302、zetamethrin。
除草剂:
例如酰苯胺类如吡氟草胺和敌稗;芳基羧酸类如二氯吡啶甲酸、麦草畏和毒草定;芳氧羧酸类如2,4-滴、2,4-滴丁酸、2,4-滴丙酸、氟草烟、2甲4氯、2甲4氯丙酸和绿草定;芳氧基苯氧链烷酸酯类如禾草灵、恶唑禾草灵、吡氟禾草灵、吡氟氯禾灵和喹禾灵;连氮酮类如杀草敏和哒草伏;氨基甲酸酯类如氯苯胺灵、甜菜安、甜菜宁和苯胺灵;氯乙酰苯胺类如甲草胺、乙草胺、丁草胺、吡草胺、异丙草胺、丙草胺和毒草胺;二硝基苯胺类如安磺灵、二甲戊乐灵和氟乐灵;二苯醚类如三氟羧草醚、甲羧除草醚、乙羧氟草醚、氟黄胺草醚、halosafen、乳氟禾草灵和乙氧氟草醚;脲类如绿麦隆、敌草隆、伏草隆、异丙隆、利谷隆和甲基苯噻隆;羟胺类如禾草灭、烯草酮、噻草酮、稀禾定和肟草酮;咪唑啉酮类如咪草烟、咪草酯、灭草烟和灭草喹;腈类如溴苯腈、敌草腈和碘苯腈;氧乙酰胺类如苯噻草胺;磺酰脲类如amidosufuron、苄嘧黄隆、氯嘧黄隆、绿黄隆、醚黄隆、甲黄隆、烟嘧黄隆、氟嘧黄隆、吡嘧黄隆、噻黄隆、醚苯黄隆和苯黄隆;硫代氨基甲酸酯类如丁草特、灭草特、燕麦敌、菌达灭、禾草畏、草达灭、苄草丹、杀草丹和野麦畏;三嗪类如莠去津、氰草津、西玛津、西草净、特丁津和特丁净;三嗪酮类如环嗪酮、苯嗪草酮和嗪草酮;其它除草剂如杀草强、呋草黄、灭草松、环庚草醚、异噁草酮、二氯吡啶酸、双苯唑快、氟硫草定、乙呋草黄、氟咯草酮、草铵膦、草甘膦、isoxaben、哒草特、二氯喹啉酸、喹草酸、草硫膦和灭草环。
此外,本发明活性化合物可以以其市售的制剂和以由这些制剂制备的使用形式存在。这些制剂可以是与增效剂的混合物。增效剂是可以增加活性化合物活性而所添加的增效剂本身无需有活性的化合物。
由市售的制剂制备的使用形式中的活性化合物的含量可以在相当宽的范围内变化。使用形式的活性化合物浓度可以是按重量计0.0000001至95%的活性化合物,优选在按重量计0.0001至1%间。
使用形式是以适合之的常规形式采用的。
当防治卫生和贮藏产品方面的害虫时,活性化合物的突出之处在于其在木材和陶土上的显著残留作用和对石灰处理过的底物上的碱的良好的稳定性。
本发明活性化合物不仅对植物、卫生和贮藏产品害虫有活性,而且在兽医方面,对动物寄生虫(体外寄生虫)如硬蜱、隐喙蜱科、疥螨、恙螨科、(叮咬和吸吮)蝇、寄生蝇幼虫、虱、头虱、鸟虱和蚤有活性。这些寄生虫包括:
虱目,例如,血虱属(Haematopinus spp.)、颚虱属(Linognathus spp.)、虱属(Pediculus spp.)、阴虱属(Phthirusspp.)、盲虱属(Solenoptes spp.)。
食毛目及amblycerina和细角亚目(Ischnocerina),例如,毛鸟虱属(Trimenopon spp.)、短角鸟虱属(Menopon spp.)、豆虱属(Trinoton spp.)、牛羽虱属(Bovicola spp.)、Werneckiellaspp.、Lepikentron spp.、畜虱属(Damalinea spp.)、啮毛虱属(Trichodectes spp.)和猫虱属(Felicola spp.)。
双翅目及长角亚目和短角亚目,例如,伊蚊属(Aedes spp.)、按蚊属(Anopheles spp.)、库蚊属(Culex spp.)、蚋属(Simuliumspp.)、真蚋属(Eusimulium spp.)、白蛉属(Phlebotomus spp.)、卢蚊属(Lutzomyia spp.)、库蠓属(Culicoides spp.)、斑虻属(Chrysops spp.)、瘤虻属(Hybomitra spp.)、黄虻属(Atylotusspp.)、虻属(Tabanus spp.)、麻虻属(Haematopota spp.)、Philipomyia spp.、Braula spp.、蝇属(Musca spp.)、齿股蝇属(Hydrotaea spp.)、螫蝇属(Stomoxys spp.)、血蝇属(Haematobia spp.)、Morellia spp.、厕蝇属(Fannia spp.)、舌蝇属(Glossina spp.)、丽蝇属(Calliphora spp.)、绿蝇属(Lucilia spp.)、金蝇属(Chrysomyia spp.)、肉蝇属(Wohlfahrtia spp.)、麻蝇属(Sarcophaga spp.)、狂蝇属(Oestrus spp.)、皮蝇属(Hypoderma spp.)、胃蝇属(Gastrophilus spp.)、虱蝇属(Hippobosca spp.)、蜱蝇属(lipoptena spp.)和羊虱蝇属(Melophagus spp.)。
蚤目,例如,蚤属(Pulex spp.)、栉头蚤属(Ctenocephalidesspp.)、鼠客蚤属(Xenopsylla spp.)和毛列蚤属(Ceratophyllusspp.)。
半翅目,例如,臭虫属(Cimex spp.)、锥蝽属(Triatomaspp.)、红腹猎蝽属(Rhodnius spp.)和全圆蝽属(Panstrongylusspp.)。
蜚蠊目,例如,东方蜚蠊(Blatta orientalis)、美洲大蠊(Periplaneta americana)、德国小蠊(Blattela germanica)和棕带蠊属(Suppella spp.)。
螨亚纲及后气亚目(Metastigmata)和中气亚目(mesostigmata),例如,隐喙蜱属(Argas spp.)、钝喙蜱属(Ornithodorus spp.)、残喙蜱属(Otabius spp.)、硬蜱属(Ixodesspp.)、花蜱属(Amblyomma spp.)、牛蜱属(Boophilus spp.)、革蜱属(Dermacentor spp.)、血蜱属(Haemaphysalis spp.)、眼玻蜱属(Hyalomma spp.)、扇头蜱属(Rhipicephalus spp.)、刺皮螨属(Dermanyssus spp.)、刺利螨属(Raillietia spp.)、肺刺螨属(Pneumonyssus spp.)、胸口螨属(Sternostoma spp.)和瓦螨属(Varroa spp.)。
Actinedida(前气孔亚目)和粉螨目(无气孔亚目),例如,蜂盾螨属(Acarapis spp.)、姬螯螨属(Cheyletiella spp.)、禽螯螨属(Ornithocheyletia spp.)、肉螨属(Myobia spp.)、疮螨属(Psorergates spp.)、蠕形属(Demodex spp.)、恙螨属(Trombicula spp.)、牦螨属(Listrophorus spp.)、粉螨属(Acarus spp.)、食酪螨属(Tyrophaus spp.)、嗜木螨属(Caloglyphus spp.)、颈下螨属(Hypodectes spp.)、翅螨属(Pterolichus spp.)、瘙螨属(Psoroptes spp.)、痒螨属(Chorioptes spp.)、耳癞螨属(Otodectes spp.)、疥螨属(Sarcoptes spp.)、痂螨属(Notoedres spp.)、疙螨属(Knemidocoptes spp.)、胞螨属(Cytodites spp.)和皮膜螨属(Laminosioptes spp.)。
例如,它们对微小牛蜱和铜绿蝇显示出突出的活性。
本发明式(I)活性化合物也适合防治侵害如下动物的节肢动物:牲畜例如牛、绵羊、山羊、马、猪、猴、骆驼、水牛、兔、鸡、火鸡、鸭、鹅、蜜蜂,其它家养动物,如狗、猫、笼养鸟、水箱中的鱼,和所谓的实验动物,例如仓鼠、豚鼠、大鼠和小鼠。防治这些节肢动物时,死亡和产量(如肉、毛、皮、蛋、蜜等)降低的情况将会减少。这样,采用本发明活性化合物使更经济有效的动物饲养成为可能。
在兽医方面,本发明活性化合物可以以已知的方式通过经胃肠道施用,例如以片剂、胶囊、药水、兽用顿服剂、颗粒剂、膏剂、大丸剂、食入法、栓剂的方式,通过非肠道施药,例如注射(肌内、皮下、静脉内、腹腔内等)、植入,经鼻施用,经皮施用,例如通过沐浴或浸蘸、喷雾、浇泼、点涂、洗刷、喷粉的方式,以及借助含有活性化合物的成形物件,如颈环、耳标、尾牌、腿箍、笼头、标记设备等。
当用于畜禽、家养动物等时,式(I)的活性化合物可以以制剂的形式(例如粉剂、乳剂、悬浮剂)的使用,所述的制剂中含有按重量计1至80%的活性化合物,该制剂可以直接施用或稀释100至10000倍后施用,或者它们可以以化学浴的形式使用。
然而,现已发现,本发明式(I)化合物对破坏工业材料的昆虫具有强的杀虫作用。
可以列举且是优选的昆虫是下列,但不限于这些昆虫:
甲虫如
北美家天牛(Hylotrupes bajulus)、长毛天牛(Chlorophoruspilosis)、具斑窃蠹(Anobium punctatum)、报死窃蠹(Xestobiumrufovillosum)、梳角细脉窃蠹(Ptilinus pecticornis)、Dendrobium pertinex、松窃蠹(Ernobium mollis)、Priobiumcarpini、褐粉蠹(Lyctus brunneus)、非洲粉蠹(Lyctusafricanus)、南方粉蠹(Lyctus planicollis)、桴粉蠹(Lyctuslinesris)、柔毛粉蠹(Lyctus pubescens)、Trogoxylon aequale、鳞毛粉蠹(Minthes rugicollis)、材小蠹(Xyleborus spec.)、Tryptodendron spec.、咖啡黑长蠹(Apate monachus)、槲长蠹(Bostyrchus capucins)、暗褐长蠹(Heterobostrychusbrunneus)、长蠹属(Sinoxylon spec.)和竹长蠹(Dinoderusminutus)。
革翅目,如
小钢青树蜂(Sirex juvencus)、大树蜂(Urocerus gigas)、U.gigas taignus、U.augur。
白蚁,如
木白蚁(Kalotermes flavicollis)、麻头堆砂白蚁(Cryptotermes brevis)、灰点异白蚁(Heterotermesindicola)、黄胸散白蚁(Reticulitermes flavipes)、Reticulitermes santonecsis、避光散白蚁(Reticulitermeslucifugus)、达尔文澳白蚁(Mastotermes darwiniensis)、湿木白蚁(Zootermopsis nevadensis)和家白蚁(Coptotermesformosanus)。
衣鱼
如西洋衣鱼(Lepisma saccharina)。
在本文中,工业材料应理解为无生命的材料如优选的是聚合物、胶水、粘性材料、纸和板、皮革、木材和木制品、和漆。
木材和木制品是非常特别优选的受保护而使之不被昆虫侵害的材料。
可以用本发明的药剂或含有之的组合物保护的木材和衍生的木制品应理解为有下列含意,例如,建筑木料、木梁、铁道枕木、桥梁组件、船用跳板、木制车辆、板箱、模板、包装箱、电线杆、木质矿道顶木、木制的门窗、胶合板、碎料板、木工的制品、或通常用在建筑或细木工中的木制品。
本发明活性化合物可以以其原样、以其浓缩物或通常的常规制剂使用。所述的常规制剂是例如可湿性粉剂、颗粒剂、溶液、悬浮剂、乳剂或膏剂。
上述制剂可以以本身已知的方式制备,例如通过将活性化合物与至少一种溶剂或稀释剂、乳化剂、分散剂和/或粘合剂或固定剂、防水剂、如果需要脱水剂和UV稳定剂和如果需要着色剂和染料和其它加工辅助剂。
用于保护木材和木制品的杀虫组合物或浓缩物包含浓度为按重量计0.0001至95%,特别是按重量计0.001至60%的活性化合物。
所采用的组合物或浓缩物的量取决于昆虫的种类和密度,以及介质。最佳施用率可以在每种情况下由一系列试验来确定。然而,一般而言,以所要保护的材料为基准,采用按重量计0.0001至20%,优选按重量计0.001至10%的活性化合物已足矣。
所用的溶剂和/或稀释剂是有机化学溶剂或溶剂混合物和/或低挥发性的油性或油样溶剂或溶剂混合物和/或极性有机化学溶剂或溶剂混合物和/或水,且如果需要是乳化剂和/或润湿剂。
所用的有机化学溶剂优选是油性或油样溶剂,所述的溶剂具有大于35的挥发度和高于30℃的闪点,优选高于45℃。用作这种油性或油样溶剂的物质是低挥发性的,且不溶于水,这类物质适合的有矿物油或其芳族馏份或含有矿物油的溶剂混合物,优选是石油溶剂、石油和/或烷基苯。
使用沸程为170到220℃的矿物油、沸程为170到220℃的石油溶剂、沸程为250到350℃的碇子油、沸程为160到280℃的石油或芳族化合物、松节油精油等是有利的。
在优选的实施方案中,所用的物质是沸程为180至210℃的液体脂族烃或沸程为180至220℃的芳族和脂族烃的高沸点混合物和/或碇子油和/或单氯萘,优选α-单氯萘。
挥发度高于35且闪点高于30℃,优选高于45℃的低挥发性有机油性或油样溶剂,可以部分地由高或中挥发性的有机化学溶剂代替,其前提条件是,溶剂混合物也具有高于35的挥发度且闪点高于30℃,优选高于45℃,且杀虫剂/杀真菌剂混合物在此溶剂混合物中是可溶的或可乳化的。
在优选的实施方案中,部分有机化学溶剂或溶剂混合物由脂族极性有机化学溶剂或溶剂混合物被代替。优选采用的物质是含有羟基和/或酯和/或醚基团的脂族有机化学溶剂,如例如乙二醇醚、酯类等。
在本发明范围内使用的有机化学粘合剂是本身已知的合成树脂和/或粘合干性油,它们可以用水稀释和/或在所采用的有机化学溶剂中是可溶的、可分散的或可乳化的,特别是那些由如下组成,或包含如下成分的粘合剂:丙烯酸树酯、乙烯树脂,例如聚乙酸乙烯酯、聚酯树酯、缩聚或加聚树脂、聚氨酯树脂、醇酸树脂或改性的醇酸树脂、苯酚树脂、烃类树脂如茚-香豆酮树脂、硅氧烷树脂、干性植物油和/或干性油和/或以天然和/或合成树脂为基础的物理干性粘合剂。
用作粘合剂合成树脂可以以乳液、分散液或溶液的形式使用。沥青或沥青状物质也可以用作粘合剂,其量至多为按重量计10%。此外,可以采用特别是本身已知的着色剂、染料、防水剂、味掩蔽剂和抑制剂或抗腐蚀剂等。
根据本发明,组合物或浓缩物优选含有至少一种醇酸树脂或改性醇酸树脂和/或干性植物油作为有机化学粘合剂。根据本发明所优选采用的物质是油含量超过按重量计45%,优选50至68%的醇酸树脂。
所有的或部分上述粘合剂可以由固定剂(混合物)或增塑剂(混合物)代替。这些添加剂是旨在防止活性化合物的挥发和结晶或沉淀。它们优选代替0.01至30%的粘合剂(以所用的粘合剂的100%为基准)。
增塑剂来自属于下列化学分类的物质:邻苯二甲酸酯类,如邻苯二甲酸二丁酯、邻苯二甲酸二辛酯或邻苯二甲酸苄基丁基酯,磷酸酯类,如磷酸三丁酯,己二酸酯类,如二(2-乙基己基)己二酸酯,硬脂酸酯,如硬脂酸丁酯或硬脂酸戊酯,油酸酯类,如油酸丁酯,甘油醚类或较高分子量乙二醇醚类、甘油酯类和对甲苯磺酸酯类。
固定剂化学上基于聚乙烯烷基醚类如聚乙烯甲基醚,或酮类如二苯甲酮或亚乙基二苯甲酮。
特别适合的溶剂或稀释剂也可以是水,如果需要是水与一或多种上述有机化学溶剂或稀释剂、乳化剂和分散剂的混合物。
特别有效的木材保护通过大规模的工业浸渍工艺,例如真空、双真空或压力工艺的方式获得。
如果需要,直接可用的组合物还可以包含其它杀虫剂和(如果需要)也可以有一或多种杀真菌剂。
可能混合于其中的另外的组分优选是WO 94/29 268中提到的杀虫剂和杀真菌剂。在上述文献中提到的化合物明确地说是本发明申请的一部分。
可以非常特别优选地混合于其中的组分是杀虫剂如毒死蜱、辛硫磷、施乐宝(silafluofen)、甲体氯氰菊酯、氟氯氰菊酯、氯氰菊酯、溴氰菊酯、氯菊酯、咪蚜胺、NI-25、氟虫脲、氟铃脲和杀虫隆,
以及杀真菌剂如环氧唑(epoxyconazole)、己唑醇、戊环醇、丙环唑、戊唑醇、环唑醇、metconazole、抑霉唑、苯氟磺胺、甲苯氟磺胺、3-碘代-2-丙炔基丁基氨基甲酸酯、N-辛基-异噻唑啉-3-酮和4,5-二氯-N-辛基异噻唑啉-3-酮。
本发明活性化合物的制备和应用可以参见下列实施例。
制备实施例
实施例Ia-1
将10.5克甲醇钠加入到实施例II-1化合物(21克;68.6毫摩尔)的DMF(30毫升)溶液中,并将此混合物在60℃下搅拌2小时。加入5毫升乙酸,并将混合物浓缩,经硅胶(1∶1乙酸乙酯∶己烷)色谱。分离出5克(25%)上述化合物,为顺-反式混合物。
无色固体,熔点:128℃。
类似于实施例Ia-1和/或根据-般制备方法,制备出列于下表中的式(Ia)化合物:
表17
Ex. | X | Y | Z | mp.:℃ | 立体化学 |
I-a-2 | CH3 | CH3 | Br | 227 | 顺/反 |
I-a-3 | Cl | Cl | CH3 | 184 | 顺/反 |
I-a-4 | C2H5 | Br | CH3 | 168-173 | 顺/反 |
I-a-5 | Cl | CH3 | CH3 | 210 | 顺/反 |
I-a-6 | Cl | CH3 | Cl | 231-233 | 顺/反 |
I-a-7 | CH3 | Cl | CH3 | 165-169 | 反 |
I-a-8 | CH3 | Cl | CH3 | 147-149 | 顺 |
I-a-9 | Cl | H | CH3 | 131-140 | 顺/反 |
I-a-10 | Cl | H | OCH3 | 185-189 | 顺/反 |
I-a-11 | Cl | Br | CH3 | 203-206 | 顺/反 |
I-a-12 | CH3 | Br | CH3 | 190-194 | 反 |
I-a-13 | CH3 | Br | CH3 | 171-174 | 顺 |
I-a-14 | Br | CH3 | Br | 225-230 | 顺/反 |
I-a-15 | CH3 | OCH3 | CH3 | 162-165 | 顺/反 |
I-a-16 | Br | CH3 | Cl | 202 | 顺/反 |
I-a-17 | Br | Cl | CH3 | 228-231 | 顺/反 |
Ex. | X | Y | Z | mp.:℃ | 立体化学 |
I-a-18 | C2H5 | Br | C2H5 | 194-197 | 反 |
I-a-19 | C2H5 | Br | C2H5 | 190-192 | 顺 |
实施例Ib-1
在冰浴下,将0.56毫升(4.55毫摩尔)戊酰氯的30毫升无水二氯甲烷溶液逐滴加入到于15毫升二氯甲烷中的1.0克(3.5毫摩尔)实施例(Ia-1)化合物和0.73毫升三乙胺中。将混合物在室温下搅拌2小时,用浓度10%柠檬酸水溶液洗涤二次,并将酸性水相用二氯甲烷萃取。合并的有机相用1N NaOH洗涤二次,碱性水相用二氯甲烷萃取,最后将合并的有机相干燥并浓缩。
获得1.32克(理论值的100%)上述化合物,为油状物(异构体混合物)。
1H NMR(CDCl3,500MHz)
δ=1.12-1.18(9H);2.02-2.30(6H);3.63-3.73(3H);6.48-6.65(2H).
类似地,和/或根据一般性制备方法,获得下列式(I-b)化合物:
表18
Ex.No. | X | Y | Z | R1 | 立体化学 | NMR数据δ |
I-b-2 | Cl | CH3 | CH3 | t-C4H9- | 顺/反 | 1.15(s,9H,C(CH3)3);6.90(s,1H,ArH);7.05(s,1H,ArH) |
I-b-3 | C2H5 | Br | CH3 | t-C4H9- | 顺/反 | 1.10(s,9H,C(CH3)3);7.2(bs,2H,ArH) |
I-b-4 | C2H5 | Br | CH3 | C2H5-O-CH2- | 顺/反 | 3.6(bs,2H,COCH2O);7.2(bs,2H,ArH) |
I-b-5 | Cl | CH3 | Cl | t-C4H9- | 顺/反 | 1.1(bs,9H,C(CH3)3);7.35(bs,2H,ArH) |
I-b-6 | Cl | H | CH3 | C2H5-O-CH2- | 顺/反 | 1.0-1.1(m,3H,CH2C H 3);2.1-2.2(m,3H,ArCH3) |
I-b-7 | CH3 | Cl | CH3 | t-C4H9- | 反 | 1.1(s,9H,C(CH3)3);7.0(s,2H,ArH) |
Ex.No. | X | Y | Z | R1 | 立体化学 | NMR数据δ |
I-b-8 | CH3 | Cl | CH3 | t-C4H9- | 顺 | 1.1(s,9H,C(CH3)3);7.0(bs,2H,ArH) |
I-b-9 | Cl | H | CH3 | t-C4H9- | 顺/反 | 1.1(s,9H,C(CH3)3);2.1(s,3H,ArCH3) |
I-b-10 | CH3 | Br | CH3 | t-C4H9- | 顺/反 | 1.05(s,9H,C(CH3)3);7.3(bs,2H,ArH) |
I-b-11 | Cl | H | OCH3 | t-C4H9- | 顺/反 | 1.15(s,9H,C(CH3)3;3.7(d,3H,OCH3) |
I-b-12 | CH3 | OCH3 | CH3 | t-C4H9- | 顺/反 | 1.1(s,9H,C(CH3)3);6.6(d,2H,ArH) |
I-b-13 | Br | CH3 | Cl | t-C4H9- | 顺/反 | 1.15(bs,9H,C(CH3)3);2.3(m,3H,ArCH3) |
I-b-14 | C2H5 | Br | C2H5 | t-C4H9- | 顺/反 | 1.1(s,9H,C(CH3)3);7.2(m,2H,ArH) |
I-b-15 | C2H5 | Br | C2H5 | C2H5-O-CH2- | 反 | 4.1(5,2H,COCH2O);7.2(bs,2H,ArH) |
在冰冷却下,将0.59毫升(4.55毫摩尔)的氯甲酸异丁酯在3毫升无水二氯甲烷中的溶液逐滴加入到于15毫升无水二氯甲烷中的1.17克(3.5毫摩尔)实施例(Ia-2)化合物和0.73ml三乙胺中。将此混合物在室温下搅拌2小时,之后如实施例(Ib-1)中的方法进行后处理。
获得1.55克(理论值的100%)上述化合物,为油状物(异构体混合物)。
1H NMR(CDCl3,500MHz)
δ=0.85-0.90(6H);2.10-2.30(6H);3.85-3.95(2H);6.97-7.24(2H).
类似地,和/或根据一般制备方法,获得下列式(I-c)化合物:
表19
Ex.No. | X | Y | Z | M | R2 | 立体化学 | NMR数据δ(ppm) |
I-c-2 | Cl | CH3 | CH3 | O | i-C4H9- | 顺/反 | 0.8-1.0(m,3H,CH2C H 3);7.0(d,2H,ArH) |
I-c-3 | Cl | CH3 | CH3 | S | i-C3H7- | 顺/反 | 1.2-1.3(m,6H,CH(C H 3)2);7.0(d.2H,ArH) |
I-c-4 | C2H5 | Br | CH3 | O | i-C4H9- | 顺/反 | 4.5-4.7(m,1H,OC H);7.2(bs,2H,ArH) |
I-c-5 | C2H5 | Br | CH3 | S | i-C3H7- | 顺/反 | 1.2-1.4(m,6H,CH(C H 3)2);7.2(d,2H,ArH) |
I-c-6 | Cl | CH3 | Cl | O | i-C4H9- | 顺/反 | 4.6-4.7(m,1H,OCH);7.35(s,2H,ArH) |
I-c-7 | CH3 | Cl | CH3 | O | i-C4H9- | 顺 | 4.5-4.6(m,1H,OCH);7.05(bs,2H,ArH) |
Ex.No. | X | Y | Z | M | R2 | 立体化学 | NMR数据δ(ppm) |
I-c-8 | CH3 | Cl | CH3 | S | i-C3H7- | 顺 | 1.2-1.3(m,6H,CH(C H 3)2;7.05(s,2H,ArH) |
I-c-9 | Cl | H | CH3 | O | i-C4H9- | 顺/反 | 2.1(m,3H,ArCH3);4.5-4.7(m,1H,OCH) |
I-c-10 | Cl | H | CH3 | S | i-C3H7- | 顺/反 | 1.2-1.3(m,6H,CH(C H 3)2;2.1(m,3H,ArCH3) |
I-c-11 | Cl | H | OCH3 | O | i-C4H9- | 顺/反 | 3.75(d,3H,OCH3);4.6-4.7(m,1H,OCH) |
I-c-12 | CH3 | OCH3 | CH3 | O | i-C4H9- | 顺/反 | 4.5-4.6(m,1H,OCH);6.6(s,2H,ArH) |
I-c-13 | CH3 | Br | CH3 | O | i-C4H9- | 顺/反 | 4.5-4.6(m,1H,OCH);7.3(s,2H,ArH) |
I-c-14 | CH3 | Br | CH3 | S | i-C3H7- | 顺/反 | 1.1-1.2(m,6H,CH(C H 3)2);7.3(s,2H,ArH) |
I-c-15 | C2H5 | Br | C2H5 | O | s-C4H9- | 顺 | 4.6-4.7(m,1H,OCH);7.3(s,2H,ArH) |
I-c-16 | C2H5 | Br | C2H5 | S | i-C3H7- | 顺 | 0.95-1.05(m,6H,CH(CH3)2;7.3(s,2H,ArH) |
在冰冷却下,将0.35毫升(4.55毫摩尔)甲磺酰氯的3毫升无水二氯甲烷溶液逐滴加入到于15毫升二氯甲烷中的1.0克(3.5毫摩尔)实施例(Ia-1)化合物和0.73毫升三乙胺中。将混合物在室温下搅拌2小时,之后如实施例(Ib-1)中的方法进行后处理。在将有机相浓缩后余下的残留物用环己烷/乙酸乙酯3/1搅拌,抽滤掉色料,并干燥。
产量:0.50克(理论值的39%);熔点:132℃。
起始物的制备
将实施例XIV-1化合物(33克,113毫摩尔)、碳酸钾(46克)、丙酮(460毫升)的混合物和碘甲烷(46毫升)回流加热5小时,用乙醚(100毫升)稀释,滤过硅胶,并浓缩。将残留物色谱(硅胶,二氯甲烷∶石油醚1∶1)。获得21克(60%)的无色油状物。
1H-NMR(CDCl3,δppm):6.62(bs,1H);6.53(bs,1H);3.74(s,3H);3.60(s,3H).
类似地实施例II-1和/或根据一般制备方法,制备出列于表20中的式(II)化合物:
表20
Ex. | X | Y | Z | 1HNMR(CDCl3,δppm) |
II-2 | CH3 | CH3 | Br | 7.22(s,1H);6.91(s,1H);3.61(s,3H);2.26(s,3H) |
II-3 | Cl | Cl | CH3 | 7.23(s,1H);7.08(s,1H);3.62(s,3H);2.21(s,3H) |
II-4 | C2H5 | Br | CH3 | 2.15(s,3H,ArCH3;7.18(d,2H,ArH) |
II-5 | Cl | CH3 | CH3 | 2.10/2.22(s,6H,ArCH3);6.95/7.08(s,2H,ArH) |
II-6 | Cl | CH3 | Cl | 2.29(s,3H,ArCH3);7.28(s,2H,ArH) |
II-7 | CH3 | Cl | CH3 | 2.16(s,6H,ArCH3);7.00(s,2H,ArH) |
II-8 | Cl | H | CH3 | 2.14(s,3H,ArCH3);7.1-7.3(m,3H,ArH) |
II-9 | Cl | H | OCH3 | 3.77(s,3H,ArOCH3);6.7-7.2(m,3H,ArH) |
II-10 | Cl | Br | CH3 | 2.21(s.3H,ArCH3);7.23/7.38(s,2H,ArH) |
II-11 | CH3 | Br | CH3 | 2.09(s,3H,ArCH3);7.20(s,2H,ArH) |
Ex. | X | Y | Z | 1HNMR(CDCl3,δppm) |
II-12 | Br | CH3 | Br | 2.26(s,3H,ArCH3);7.32(s,2H,ArH) |
II-13 | CH3 | OCH3 | CH3 | 2.07(s,6H,ArCH3);6.58(s,2H,ArH) |
II-14 | Br | CH3 | Cl | 2.29(s,3H,ArCH3);7.32/7.45(s,2H,ArH) |
II-15 | Br | Cl | CH3 | 2.22(s,3H,ArCH3);7.12/7.41(s,2H,ArH) |
II-16 | C2H5 | Br | C2H5 | 2.47(q,4H,ArCH2);7.19(s,2H,ArH) |
实施例XIV-1
将24.8克(119毫摩尔)2,4-二甲基-6-甲氧基苯基乙酸甲酯加入到二异丙基氨基锂(130毫摩尔)的四氢呋喃(THF)(100毫升)溶液中。在室温下30分钟之后,加入17克3,4-四亚甲基琥珀酸甲酯酰氯,并将混合物在室温下搅拌(1小时)。之后加入100毫升水和30克氯化铵。将中间体用乙醚萃取,并滤过硅胶。浓缩后,将残留物(油,44克)用88克氢氧化钾和250毫升水在回流下沸腾(2天)。将混合物冷却,并酸化(浓HCl),滤出固体。给出33克示上述化合物XIV-1。
无色固体,mp.128℃。
类似于实施例XIV-1和/或根据一般制备方法,制备出列于表21中的式(XIV)化合物:
表21
Ex. | X | Y | Z | 1HNMR(CDCl3,δppm) |
XIV-3 | Cl | Cl | CH3 | 3.85(s,2H);2.80(m,2H) |
XIV-2 | CH3 | CH3 | Br | 6.93(s,1H);7.25(s,1H);2.80(m,2H) |
在某些情况下,在式(II)化合物的合成中采用式(XIV)化合物的粗制产物
其中
B、B’、X、Y和Z各如上所定义。
应用实施例
实施例A
二点叶螨试验(抗性)
溶剂:7份重量的二甲基甲酰胺
乳化剂:1份重量的烷芳基聚乙二醇醚
制备活性化合物的合适制剂时,将1份重量的活性化合物与所述量的溶剂和乳化剂混合,并将该乳油用水稀释至所需浓度。
将严重滋生所有生长阶段的温室二点叶螨(Tetranychusurticae)的菜豆植株(Phaseolus vulgaris),浸入所需浓度的活性化合物制剂中。
经过所希望的时间后,确定杀死%。100%是指所有的叶螨均被杀死;0%是指没有叶螨被杀死。
在此试验中,例如,在示范的0.01%的活性化合物浓度下,制备实施例Ia-1化合物在13天后达到100%死亡率。
实施例B
辣根猿叶甲幼虫试验
溶剂:7份重量的二甲基甲酰胺
乳化剂:1份重量的烷芳基聚乙二醇醚
制备活性化合物的合适制剂时,将1份重量的活性化合物与所述量的溶剂和乳化剂混合,并将该乳油用水稀释至所需浓度。
将甘蓝(Brassica oleracea)叶片通过浸入所需浓度的活性化合物制剂中来处理,当叶片仍湿润时,放入辣根猿叶甲(Phaedoncochleariae)幼虫。
经过所希望的时间后,确定杀死%。100%是指所有的幼虫均被杀死;0%是指没有幼虫被杀死。
在此试验中,例如,在示范的0.1%的活性化合物浓度下,制备实施例Ia-1、Ia-2和Ia-3化合物在7天后达到100%死亡率。
实施例C
小菜蛾幼虫试验
溶剂:7份重量的二甲基甲酰胺
乳化剂:1份重量的烷芳基聚乙二醇醚
制备活性化合物的合适制剂时,将1份重量的活性化合物与所述量的溶剂和乳化剂混合,并将该乳油用水稀释至所需浓度。
将甘蓝(Brassica oleracea)叶片通过浸入所需浓度的活性化合物制剂中来处理,当叶片仍湿润时,放入小菜蛾(Plutellamaculipennis)幼虫。
经过的时间后,确定杀死%。100%是指所有的幼虫均被杀死;0%是指没有幼虫被杀死。
在此试验中,例如,在示范的0.1%的活性化合物浓度下,制备实施例Ia-1、Ia-2和Ia-3在7天后达到100%死亡率。
实施例D
黑尾叶蝉试验
溶剂:7份重量的二甲基甲酰胺
乳化剂:1份重量的烷芳基聚乙二醇醚
制备活性化合物的合适制剂时,将1份重量的活性化合物与所述量的溶剂和乳化剂混合,并将该乳油用水稀释至所需浓度。
将稻秧(Oryza sativa)通过浸入所需浓度的活性化合物制剂中来处理,当稻秧仍润湿时,放上黑尾叶蝉(Nephotettixcincticeps)。
经过了所需的时间后,确定杀死%。100%是指所有的黑尾叶蝉均被杀死;0%是指没有黑尾叶蝉被杀死。
在此试验中,例如,在示范的0.1%的活性化合物浓度下,制备实施例Ia-1、Ia-2和Ia-3化合物在6天后达到100%死亡率。
实施例E
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,24小时后,用活性化合物制剂浇水。最好使每单位面积的水量保持恒定。制剂中活性化合物的浓度是不重要的,只有每单位施用的活性化合物的量是关键的。三周后,将植物的损害程度与未处理对照的发育进行目视比较,定出损害%。数值的含意如下:
0%=无作用(与未处理相同)
100%=完全损害
在此试验中,在示范的60克/公顷的施用量下,例如制备实施例Ia-1化合物对看麦娘属、雀麦属、蜀黍属和母菊属显示出至少90%的活性,而大麦和棉花则对之有非常好的耐受性。
在此试验中,在示范的250克/公顷的施用量下,例如制备实施例Ia-2化合物对看麦娘属、狗尾草属和芥属显示出100%的活性。
在此试验中,在示范的250克/公顷的施用量下,例如制备实施例Ia-3化合物对看麦娘属显示出至少80%的活性,而甘蔗对之有非常好的耐受性。
实施例F
桃蚜试验
溶剂:3份重量的二甲基甲酰胺
乳化剂:1份重量的烷芳基聚乙二醇醚
制备活性化合物的合适制剂时,将1份重量的活性化合物与所述量的溶剂和乳化剂混合,并将该乳油用水稀释至所需浓度。
将严重滋生桃蚜(Myzus persicae)的甘蓝叶(Brassicaoleracea)通过浸入所需浓度的活性化合物制剂中来处理。
经过所希望的时间后,确定杀死%。100%是指所有的蚜虫均被杀死;0%是指没有蚜虫被杀死。
在此试验中,例如,在示范的0.1%的活性化合物浓度下,制备实施例Ia-1、Ia-2和Ia-3化合物在6天后达到至少90%死亡率。
Claims (10)
2.根据权利要求1的式(I)化合物,其中
X代表氯、溴、C1-C4-烷基,
Y代表氢、氯、溴、C1-C4-烷基、C1-C4-烷氧基,
Z代表氯、溴、C1-C4-烷基、C1-C4-烷氧基,
其中X、Y和Z不同时代表甲基,
R1代表C1-C16-烷基、C1-C6-烷氧基C1-C6-烷基,
R2代表C1-C16-烷基,
R3代表C1-C9-烷基。
3.根据权利要求1的式(I)化合物,其中
X代表氯、溴、甲基、乙基,
Y代表氢、氯、溴、甲基、甲氧基,
Z代表氯、溴、甲基、乙基、甲氧基,
X、Y和Z不同时代表甲基,
R1代表t-C4H9-,C2H5-O-CH2,
R2代表i-C4H9-,i-C3H7-,s-C4H9-,
R3代表CH3。
4.制备权利要求1的式(I)化合物的方法,其特征在于
其中
A、B、B’、Q、X、Y和Z各如权利要求1中所定义,
在稀释剂存在下和在碱存在下,
使式(II)化合物进行分子内缩合反应
其中
A、B、B’、Q、X、Y和Z各如上所定义,
且
R12代表烷基;和
(B)如下获得式(I-b)化合物:
其中
A、B、B’、Q、X、Y、Z和R1各如权利要求1中所定义,
使式(Ia)化合物
其中
A、B、B’、X、Y、Z和Q各如上所定义,
α) 如果适当的话在稀释剂存在下,且如果适当的话在酸结合剂存在下,与式(III)的酰氯反应
其中
R1如上所定义且
Hal代表卤素;
或
β)如果适当的话在稀释剂存在下,且如果适当的话在酸结合剂存在下,与式(IV)的羧酸酐反应
R1-CO-O-CO-R1 (IV)
其中
R1如上所定义;和
(C)如下获得式(Ic-1)化合物:
其中A、B、B’、Q、X、Y、Z和R2各如权利要求1中所定义,
且
M代表氧或硫,
如果适当的话在稀释剂存在下,且如果适当的话在酸结合剂存在下,
使式(Ia)化合物与式(V)的氯甲酸酯或氯甲酸硫醇酯反应
其中
A、B、B’、Q、X、Y和Z各如上所定义,
R2-M-CO-Cl (V)
其中
R2和M各如上所定义;和
其中A、B、B’、Q、X、Y、Z和R2各如权利要求1中所定义,
且
M代表氧或硫,
其中
A、B、B’、Q、X、Y和Z各如上所定义,
其中
M和R2各如上所定义;
或
β)如果适当的话在稀释剂存在下,且如果适当的话在碱存在下,与二硫化碳反应,之后与通式(VII)的烷基卤反应
R2-Hal (VII)
其中
R2如上所定义,且
Hal代表氯、溴或碘;
和
其中A、B、B’、Q、X、Y、Z和R3各如权利要求1中所定义,
如果适当的话在稀释剂存在下,且如果适当的话在酸结合剂存在下,
使式(Ia)化合物与式(VIII)的磺酰氯反应
其中
A、B、B’、Q、X、Y和Z各如上所定义,
R3-SO2-Cl (VIII)
其中
R3如上所定义;
其中A、B、L、B’、Q、X、Y、Z、R4和R5各如权利要求1中所定义,
如果适当的话在稀释剂存在下,且如果适当的话在酸结合剂存在下,
其中
A、B、B’、Q、X、Y和Z各如上所定义,
其中
L、R4和R5各如上所定义
且
Hal代表卤素;
和
(G)如下获得式(If)化合物:
其中A、B、B’、Q、X、Y和Z各如权利要求1中所定义,
且
E代表金属离子等价物或代表铵离子,
如果适当的话在稀释剂存在下,
其中
其中
Me代表一或二价金属离子,
t代表数字1或2,
R13、R14和R15相互独立地各代表氢或烷基;和
R16代表氢、羟基或C1-C4-烷氧基;
(H)如下获得式(Ig)化合物:
其中
A、B、L、B’、Q、X、Y、Z、R6和R7各如权利要求1中所定义,
其中
A、B、B’、Q、X、Y和Z各如上所定义,
α)如果适当的话在稀释剂存在下,且如果适当的话在催化剂存在下,与式(XII)化合物反应
R6-N=C=L (XII)
其中
L和R6如上所定义;
或
其中
L、R6和R7各如上所定义。
5.式(II)化合物,
其中
A、B、B’、Q、X、Y和Z各如权利要求1中所定义,
且
R12代表烷基。
6.杀虫剂和除草剂,其特征在于,它们包含至少一种权利要求1的式(I)化合物。
7.权利要求1的式(I)化合物防治害虫和杂草的应用。
8.防治害虫和杂草的方法,其特征在于,使权利要求1的式(I)化合物作用于害虫、杂草和/或其栖生地。
9.制备杀虫剂和除草剂的方法,其特征在于,将权利要求1的式(I)化合物与填充剂和/或表面活性剂混合。
10.权利要求1的式(I)化合物制备杀虫剂和除草剂的应用。
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EP (1) | EP0854852B1 (zh) |
JP (1) | JP4115523B2 (zh) |
KR (1) | KR100444928B1 (zh) |
CN (1) | CN1119310C (zh) |
AU (1) | AU707451B2 (zh) |
BR (1) | BR9611075B1 (zh) |
CA (1) | CA2234719A1 (zh) |
DE (2) | DE19538218A1 (zh) |
ES (1) | ES2165523T3 (zh) |
PL (1) | PL326224A1 (zh) |
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WO (1) | WO1997014667A1 (zh) |
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DE19808261A1 (de) | 1998-02-27 | 1999-10-28 | Bayer Ag | Arylphenylsubstituierte cyclische Ketoenole |
DE19813354A1 (de) | 1998-03-26 | 1999-09-30 | Bayer Ag | Arylphenylsubstituierte cyclische Ketoenole |
DE19818732A1 (de) * | 1998-04-27 | 1999-10-28 | Bayer Ag | Arylphenylsubstituierte cyclische Ketoenole |
DE19935963A1 (de) | 1999-07-30 | 2001-02-01 | Bayer Ag | Biphenylsubstituierte cyclische Ketoenole |
DE10139465A1 (de) * | 2001-08-10 | 2003-02-20 | Bayer Cropscience Ag | Selektive Herbizide auf Basis von substituierten, cayclischen Ketoenolen und Safenern |
DE10249055A1 (de) * | 2002-10-22 | 2004-05-06 | Bayer Cropscience Ag | 2-Phenyl-2-substituierte-1,3-diketone |
DE10311300A1 (de) * | 2003-03-14 | 2004-09-23 | Bayer Cropscience Ag | 2,4,6-Phenylsubstituierte cyclische Ketoenole |
DE10326386A1 (de) | 2003-06-12 | 2004-12-30 | Bayer Cropscience Ag | N-Heterocyclyl-phenylsubstituierte cyclische Ketoenole |
DE102004014620A1 (de) * | 2004-03-25 | 2005-10-06 | Bayer Cropscience Ag | 2,4,6-phenylsubstituierte cyclische Ketoenole |
CA2566084C (en) * | 2004-06-07 | 2014-01-21 | Syngenta Participations Ag | Methods of reducing nematode damage |
DE102005059469A1 (de) | 2005-12-13 | 2007-06-14 | Bayer Cropscience Ag | Insektizide Zusammensetzungen mit verbesserter Wirkung |
DE102006007882A1 (de) | 2006-02-21 | 2007-08-30 | Bayer Cropscience Ag | Cycloalkyl-phenylsubstituierte cyclische Ketoenole |
GB0715454D0 (en) | 2007-08-08 | 2007-09-19 | Syngenta Ltd | Novel herbicides |
GB0715576D0 (en) | 2007-08-09 | 2007-09-19 | Syngenta Ltd | Novel herbicides |
GB0812310D0 (en) | 2008-07-03 | 2008-08-13 | Syngenta Ltd | Novel herbicides |
BRPI1008949B1 (pt) | 2009-03-11 | 2018-07-10 | Bayer Intellectual Property Gmbh | Cetoenóis haloalquilmetilenóxi-fenil-substituídos e seu uso, composição, seu uso e seu método de produção, métodos para combate de pestes animais e/ou crescimento de plantas indesejadas |
JP2012526732A (ja) * | 2009-05-16 | 2012-11-01 | シンジェンタ リミテッド | 新規除草剤 |
GB0912385D0 (en) * | 2009-07-16 | 2009-08-26 | Syngenta Ltd | Novel herbicides |
DE102010008644A1 (de) | 2010-02-15 | 2011-08-18 | Bayer Schering Pharma Aktiengesellschaft, 13353 | Zyklische Ketoenole zur Therapie |
DE102010008642A1 (de) | 2010-02-15 | 2011-08-18 | Bayer Schering Pharma Aktiengesellschaft, 13353 | Zyklische Ketoenole zur Therapie |
DE102010008643A1 (de) | 2010-02-15 | 2011-08-18 | Bayer Schering Pharma Aktiengesellschaft, 13353 | Zyklische Ketoenole zur Therapie |
JP6180936B2 (ja) | 2010-11-02 | 2017-08-16 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングBayer Intellectual Property GmbH | フェニル置換ビシクロオクタン−1,3−ジオン誘導体 |
DE102011011040A1 (de) | 2011-02-08 | 2012-08-09 | Bayer Pharma Aktiengesellschaft | (5s,8s)-3-(4'-Chlor-3'-fluor-4-methylbiphenyl-3-yl)-4-hydroxy-8-methoxy-1-azaspiro[4.5]dec-3-en-2-on (Verbindung A) zur Therapie |
AU2012293611B2 (en) | 2011-08-11 | 2017-02-09 | Bayer Cropscience Ag | 1,2,4-triazolyl-substituted keto-enols |
AU2013211636B2 (en) | 2012-01-26 | 2016-09-29 | Bayer Intellectual Property Gmbh | Phenyl-substituted ketoenols for controlling fish parasites |
AR094054A1 (es) * | 2012-12-19 | 2015-07-08 | H Lundbeck As | 6-cloro-3-(fenil-d₅)-inden-1-ona y uso de la misma |
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US4283348A (en) * | 1978-09-22 | 1981-08-11 | Union Carbide Corporation | Method of preparing 2-aryl-3-cyclopentanedione compounds |
US5840661A (en) * | 1994-07-07 | 1998-11-24 | Bayer Aktiengesellschaft | 2-aryl cyclopentane-1,3-dione derivatives |
WO1996003366A1 (de) * | 1994-07-21 | 1996-02-08 | Bayer Aktiengesellschaft | 2-(2,4,6-trimethylphenyl)-cyclopentan-1,3-dion-derivate |
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- 1996-10-01 KR KR10-1998-0702362A patent/KR100444928B1/ko not_active IP Right Cessation
- 1996-10-01 DE DE59607961T patent/DE59607961D1/de not_active Expired - Lifetime
- 1996-10-01 PL PL96326224A patent/PL326224A1/xx unknown
- 1996-10-01 CA CA002234719A patent/CA2234719A1/en not_active Abandoned
- 1996-10-01 AU AU72837/96A patent/AU707451B2/en not_active Ceased
- 1996-10-01 ES ES96934507T patent/ES2165523T3/es not_active Expired - Lifetime
- 1996-10-01 WO PCT/EP1996/004283 patent/WO1997014667A1/de active IP Right Grant
- 1996-10-01 BR BRPI9611075-9A patent/BR9611075B1/pt not_active IP Right Cessation
- 1996-10-01 CN CN96198921A patent/CN1119310C/zh not_active Expired - Fee Related
- 1996-10-01 TR TR1998/00584T patent/TR199800584T1/xx unknown
- 1996-10-01 EP EP96934507A patent/EP0854852B1/de not_active Expired - Lifetime
- 1996-10-01 JP JP51546197A patent/JP4115523B2/ja not_active Expired - Fee Related
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US4551547A (en) * | 1980-11-10 | 1985-11-05 | Union Carbide Corporation | Biocidal 2-aryl-1, 3-cyclopentanedione enol ester compounds |
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Publication number | Publication date |
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EP0854852A1 (de) | 1998-07-29 |
KR19990063890A (ko) | 1999-07-26 |
KR100444928B1 (ko) | 2004-12-08 |
PL326224A1 (en) | 1998-08-31 |
BR9611075A (pt) | 1999-07-13 |
CN1204313A (zh) | 1999-01-06 |
BR9611075B1 (pt) | 2010-07-27 |
AU707451B2 (en) | 1999-07-08 |
DE59607961D1 (de) | 2001-11-22 |
EP0854852B1 (de) | 2001-10-17 |
AU7283796A (en) | 1997-05-07 |
DE19538218A1 (de) | 1997-04-17 |
JP2000517286A (ja) | 2000-12-26 |
US6569810B1 (en) | 2003-05-27 |
JP4115523B2 (ja) | 2008-07-09 |
CA2234719A1 (en) | 1997-04-24 |
WO1997014667A1 (de) | 1997-04-24 |
TR199800584T1 (xx) | 1998-06-22 |
ES2165523T3 (es) | 2002-03-16 |
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