CN1217903C - 取代联苯基噁唑啉 - Google Patents
取代联苯基噁唑啉 Download PDFInfo
- Publication number
- CN1217903C CN1217903C CN011112611A CN01111261A CN1217903C CN 1217903 C CN1217903 C CN 1217903C CN 011112611 A CN011112611 A CN 011112611A CN 01111261 A CN01111261 A CN 01111261A CN 1217903 C CN1217903 C CN 1217903C
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- acid
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- YEBXJRBNPTUQKG-UHFFFAOYSA-N 1,1'-biphenyl;4,5-dihydro-1,3-oxazole Chemical class C1CN=CO1.C1=CC=CC=C1C1=CC=CC=C1 YEBXJRBNPTUQKG-UHFFFAOYSA-N 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims description 220
- 229910052801 chlorine Inorganic materials 0.000 claims description 26
- 239000000460 chlorine Substances 0.000 claims description 22
- 229910052731 fluorine Inorganic materials 0.000 claims description 21
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 18
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 15
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 15
- 229910052794 bromium Inorganic materials 0.000 claims description 15
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 239000000543 intermediate Substances 0.000 abstract description 4
- 230000000361 pesticidal effect Effects 0.000 abstract 1
- 238000000034 method Methods 0.000 description 194
- 238000002360 preparation method Methods 0.000 description 81
- -1 difluoro methyl halide Chemical class 0.000 description 71
- 238000006243 chemical reaction Methods 0.000 description 70
- 239000003513 alkali Substances 0.000 description 55
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 54
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 47
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- 239000000047 product Substances 0.000 description 33
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- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 13
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 12
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- 238000011010 flushing procedure Methods 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical class CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 11
- 238000000967 suction filtration Methods 0.000 description 11
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- 206010039509 Scab Diseases 0.000 description 10
- 125000003342 alkenyl group Chemical group 0.000 description 10
- 125000003545 alkoxy group Chemical group 0.000 description 10
- 150000003851 azoles Chemical class 0.000 description 10
- 238000002425 crystallisation Methods 0.000 description 10
- 230000008025 crystallization Effects 0.000 description 10
- 229930195733 hydrocarbon Natural products 0.000 description 10
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- 238000012360 testing method Methods 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 9
- 241000238631 Hexapoda Species 0.000 description 9
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 8
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
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- 244000025254 Cannabis sativa Species 0.000 description 7
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- 125000000217 alkyl group Chemical group 0.000 description 7
- 230000031709 bromination Effects 0.000 description 7
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- 238000010438 heat treatment Methods 0.000 description 7
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- 150000002825 nitriles Chemical group 0.000 description 7
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 description 6
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- 238000007738 vacuum evaporation Methods 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
- LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
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- 150000003751 zinc Chemical class 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
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D263/14—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with radicals substituted by oxygen atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/64—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/67—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/68—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/73—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/81—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/82—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/87—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C251/44—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups being part of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
-
- 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
- C07C45/46—Friedel-Crafts reactions
-
- C—CHEMISTRY; METALLURGY
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Abstract
本发明涉及式(I)的新的取代联苯基噁唑啉,其制备方法,新的中间体以及应用取代联苯基噁唑啉防治有害动物,其中R,X,m和n为说明书中给定的定义。
Description
本申请是申请号为95115331.4的专利申请的分案申请。
本发明涉及新的取代联苯基噁唑啉,其多种制备方法,新的中间体,以及应用取代联苯基噁唑啉防治有害动物。
已知一些取代联苯基噁唑啉,如2-(2,6-二氟苯基)-4-(4′-氯联苯基-4)-2-噁唑啉,具有杀虫和杀螨活性(参见EP-A-O432661)。
可是,在各种使用领域,特别是防治一些生物体或当以低剂量使用时,这些已知化合物的活性水平和/或特效性不能令人完全满意。
现已发现了式(I)的新的取代联苯基噁唑啉
其中
R代表R1和R2,其中
R1代表在各种情况下至少具有一个氟原子和另外至少一个氢原子或
氯原子的卤代烷基或卤代环烷基,或代表至少具有一个氟原子的卤代环链烯基,
R2代表氢,链烯基,链炔基,或代表可选择取代的环烷基,
或代表可选择取代的环烷基烷基,
或代表可选择取代的环链烯基烷基,
或代表可选择取代的环链烯基,
或代表各自可选择取代的苯基烷基或萘基烷基,
或代表可选择取代的杂芳基烷基,
或代表COR3基,
其中
R3代表烷基,烷氧基,链烯基,链烯氧基,
或代表各自可选择取代的环烷基,环烷氧基或环烷基烷氧基,
或代表各自可选择取代的苯基或萘基,
或代表NR4R5基,
其中
R4代表氢或烷基和
R5代表烷基,卤代烷基,或代表各自可选择取代的环烷基或环烷基烷基,或代表各自可选择取代的苯基或苯基烷基,
X代表卤素,烷基或烷氧基,
m代表0,1或2和
n代表1或2。
由于存在一个或多个手性中心,通常获得的是立体异构体混合物形式的式(I)化合物。它们可以是非对映异构体的混合物且也可以纯的非对映异构体或对映体的形式使用。
而且,已发现式(I)的新的取代联苯基噁唑啉是通过下述方法获得的,其中
A)在第一个步骤中,制备式(II)化合物
其中
R1,X,m和n如上述定义,
α)为了制备式(IIa)化合物,将式(III)的羟基联二苯与式(IV)化合物进行反应
其中
W和Y各自独立地代表氟,氯或三氟甲基,
B代表氢或氟,
Z代表氟或
W和Z一起代表-(CF2)1
其中
l代表2,3或4,
n代表1或2和
m代表0,1或2,
其中X,m和n如上述定义,
其中
W,Y和Z如上述定义,
如果适宜反应在碱存在下,如果适宜,在催化剂存在下和如果适宜,在稀释剂存在下进行,且如果适宜,随后氢化产物,
或
β)为了制备式(IIb)化合物,将上述式(III)的羟基联二苯与式(V)的二氟卤代甲烷反应
其中
X,m和n如上述定义,
CHF2Hal (V)
其中
Hal代表氯或溴,
如果适宜,在碱存在下,如果适宜,在催化剂存在下,和如果适宜,在稀释剂存在下进行反应,
或
γ)为了制备式(IIc)的化合物,将式(VI)的氨基苯酚衍生物重氮化,且所得的重氮盐与苯在酸和铁粉存在下或在碱存在下,且在每种情况下,如果适宜,在稀释剂存在下进行反应。
其中
X,R1,m和n如上述定义,
其中
X,R1,m和n如上述定义,
或
δ)为了制备式(IId)的化合物,将上述式(III)的羟基联二苯与四氯化碳在氢氟酸存在下,如果适宜,在稀释剂存在下反应。
其中
X,m和n如上述定义,
B)在第二步中,制备式(VII)化合物
其中
X,R1,m和n如上述定义,
α)由方法A)制备的式(II)化合物与乙酰氯,在酸或路易斯酸存在下,且在稀释剂存在下进行反应,
或
β)为了制备式(VIIa)的化合物,将式(IIIa)的羟基联二苯衍生物与式(IV)的化合物反应
其中
B,X,m,n,W,Y和Z如上述定义,
其中
X,m和n如上述定义
其中
W,Y和Z如上述定义,
如果适宜在碱存在下,如果适宜在催化剂存在下且如果适宜在溶剂存在下进行反应,且如果适宜,可随后氢化产物,
或
γ)为了制备式(VIIb)的化合物
其中
X,m和n如上述定义,
将上述式(IIIa)的羟基联二苯衍生物与上述式(V)的二氟卤代甲烷,如果适宜在碱存在下,如果适宜在催化剂存在下,且如果适宜在稀释剂存在下进行反应,
C)在第三步中,制备式(VIII)的化合物
其中
X,R1,m和n如上述定义和
Hal代表氯或溴,
α)将通过方法B)制备的上述式(VII)化合物,如果适宜,在稀释剂存在下,进行氯化或溴化,
或
β)通过方法A)制备的上述式(II)化合物与式(IX)的卤代酰氯在酸或路易斯酸存在下和在稀释剂存在下进行反应,
HalCH2COCl (IX)
其中
Hal代表氯或溴,
D)在第四步中,制备式(X)化合物
其中
X,R1,m和n如上述定义
将通过方法C)制备的上述式(VIII)化合物与甲酸盐,在稀释剂存在下,且如果适宜,在催化剂存在下进行反应,
E)在第五步中,制备式(XI)化合物
其中
X,R1,m和n如上述定义,
将通过方法D)制备的上述式(X)化合物,与式(XII)化合物,如果适宜在稀释剂存在下进行反应
H2N-OCH3 (XII),
F)在第六步中,制备式(XIII)化合物
其中
R1,X,m和n如上述定义,
将通过方法E)制备的上述式(XI)化合物,在酸存在下,如果适宜,在稀释剂存在下用还原剂还原,
G)在第七步中,制备式(XIV)化合物
其中
R1,X,m和n如上述定义,
或者是
α)将通过方法F)制备的上述式(XIII)化合物,与2,6-二氟苯甲酰氯反应,如果适宜反应在碱存在下,且如果适宜在稀释剂存在下进行,
或者是
β)将通过方法A)制备的上述式(II)化合物,首先与式(XV)化合物,在酸性催化剂存在下,且如果适宜,在稀释剂存在下反应
其中
V代表氯,羟基或C1-C4-烷氧基和
R6代表氢或烷基,优选代表氢或C1-C6-烷基,
并将所得的式(XVI)化合物,在稀释剂存在下用还原剂还原,
其中
R1,X,m,n和R6如上述定义,
H)在第八步中,制备式(XVII)化合物
其中
X,m和n如上述定义,
R′代表R1或COR3,其中
R1和R3如上述定义
或者是
α)将通过方法G)制备的上述式(XIV)化合物,与氯化剂反应,如果适宜,反应在稀释剂存在下进行,
或者是
β)将通过方法A)制备的上述式(II)化合物,或下式(IIe)化合物,与式(XVIII)化合物在酸性催化剂存在下,且如果适宜在稀释剂存在下反应,
其中
R3,X,n和m如上述定义,
且
I)在第九步中,将通过方法H)制备的上述式(XVII)化合物,在碱存在下环化,如果适宜,反应在催化剂存在下,且如果适宜,在稀释剂存在下进行,
且,如果适宜
J)将对于R=COR3制备的式(Ia)化合物水解,得到式(Ib)化合物
其中
R3,X,n和m如上述定义
其中
X,n和m如上述定义
且,如果适宜,将这些化合物随后
Kα)与式(XIX)化合物反应
HalCOR3 (XIX)
其中
R3如上述定义且
Hal代表卤素,优选代表氯或溴,如果适宜反应在稀释剂存在下且如果适宜在碱存在下进行,或
β)与式(IV)化合物反应
其中
W,Y和Z如上述定义,
如果适宜反应在碱存在下,如果适宜,在催化剂存在下和如果适宜,在稀释剂存在下进行,且如果适宜,随后氢化产物,
或
γ)与式(V)的二氟卤代甲烷反应
CHF2Hal (V)
其中
Hal代表氯或溴,
如果适宜在碱存在下,如果适宜在催化剂存在下,且如果适宜在稀释剂存在下进行反应,
或
δ)在氢氟酸存在下,如果适宜在稀释剂存在下与四氯化碳反应,或
ε)与式(XX)化合物反应
M-R2 (XX)
其中
R2如上述定义且
M代表离去基,如果适宜在稀释剂存在下,且如果适宜在碱存在下进行反应。
而且,已经发现新的式(I)取代联苯基噁唑啉非常适合用于防治农业、造林业、贮藏品和材料的保护以及卫生领域中存在的有害动物,特别是昆虫,螨类和线虫。
式(I)提供了根据本发明化合物的总定义,
列示于上述和下述式中的优选取代基或基团的范围被解释如下。
R优选代表R1或R2,其中
R1代表在各种情况下至少具有一个氟原子和另外至少一个氢原子或氯原子的C1-C6-卤代烷基或C3-C6-卤代环烷基,或代表至少具有一个氟原子的C4-C6-卤代环链烯基和
R2代表氢,C3-C12-链烯基,C3-C12-链炔基,或代表可被C1-C4-烷基,C2-C4-链烯基,C2-C4-卤代链烯基,苯基,卤代苯基,苯乙烯基或卤代苯乙烯基可选择取代的C3-C6-环烷基,
或代表可被卤素,C1-C4-烷基,C2-C4-链烯基,C2-C4-卤代链烯基,苯基,卤代苯基,苯乙烯基或卤代苯乙烯基可选择取代的C3-C6-环烷基-C1-C4-烷基,或代表可被卤素或C1-C4-烷基可选择取代的C4-C6-环链烯基-C1-C4-烷基,
或代表可被C1-C4-烷基可选择取代的C4-C6-环链烯基,
或代表苯基-C1-C6-烷基,萘基-C1-C3-烷基或四氢萘基-C1-C3-烷基,它们各自可被相同或不同的取代基可选择地单取代至四取代,这些取代基为由硝基,卤素,C1-C12-烷基,C1-C12-卤代烷基,C1-C12-烷氧基或C1-C12-卤代烷氧基组成的一系列基团,
或代表5-或6-元杂芳基-C1-C4-烷基,其可被相同或不同的取代基可选择地单取代或双取代,这些取代基为由硝基,卤素,C1-C12-烷基,C1-C12-卤代烷基,C1-C12-烷氧基或C1-C12-卤代烷氧基组成的一系列基团,且其具有1或2个相同或不同的杂原子,杂原子为由氮,氧和硫组成的一系列原子,
或代表COR3基。
R3优选代表C1-C12-烷基,C1-C12-烷氧基,C3-C12-链烯基,C3-C12-链烯氧基,或代表各自可被卤素,C1-C4-烷基,C1-C4-卤代烷基,C2-C4-链烯基或C2-C4-卤代链烯基可选择取代的C3-C10-环烷基,C3-C10-环烷氧基或C3-C10-环烷基-C1-C6-烷氧基,
或代表苯基或萘基,它们各自可被相同或不同的取代基可选择地单取代至四取代,取代基为由卤素,C1-C12-烷基,C1-C12-卤代烷基,C1-C12-烷氧基或C1-C12-卤代烷氧基组成的一系列基团,或代表NR4R5基。
R4优选代表氢或C1-C12-烷基。
R5优选代表C1-C12-烷基,C1-C12-卤代烷基,或代表各自可被卤素,C1-C4-烷基,C1-C4-卤代烷基或C2-C4-卤代链烯基可选择取代的C3-C10-环烷基或C3-C10-环烷基-C1-C6-烷基,或代表苯基或苯基-C1-C6-烷基,它们各自可被相同或不同的取代基可选择地单取代至四取代,取代基为由卤素,C1-C12-烷基,C1-C12-卤代烷基,C1-C12-烷氧基或C1-C12-卤代烷氧基组成的一系列基团。
X优选代表卤素,C1-C6-烷基或C1-C12-烷氧基,
m优选代表0,1或2。
n优选代表1或2。
R特别优选地代表R1或R2,其中,
R1代表在各种情况下至少具有一个氟原子和另外至少一个氢原子或氯原子的C1-C3-卤代烷基或C4-C5-卤代环烷基,或代表至少具有一个氟原子的C4-C6-卤代环链烯基,和
R2代表氢,C3-C12-链烯基,C3-C5-链炔基,或代表可被C1-C4-烷基,,C2-C4-链烯基,C2-C3-卤代链烯基,苯基,卤代苯基,苯乙烯基或卤代苯乙烯基可选择取代的C3-C6-环烷基,
或代表可被卤素,C1-C4-烷基,C2-C4-链烯基,C2-C3-卤代链烯基,苯基,卤代苯基,苯乙烯基或卤代苯乙烯基可选择取代的C3-C6-环烷基-C1-C4-烷基,或代表可被卤素可选择取代的C4-C6-环链烯基甲基,或代表C4-C6-环链烯基,
或代表苯基-C1-C6-烷基,萘基甲基,四氢萘基甲基,吡啶基-,呋喃基-,噻唑基-,噁唑基-或异噁唑基-C1-C3-烷基,它们各自可被相同或不同的取代基可选择地单取代或二取代,这些取代基为由硝基,卤素,C1-C4-烷基,C1-C4-卤代烷基,C1-C4-烷氧基或C1-C4-卤代烷氧基组成的一系列基团,或代表COR3基。
R3更优选地代表C1-C6-烷基,C1-C6-烷氧基,C3-C6-链烯基,C3-C6-链烯氧基,或代表各自可被氟,氯,C1-C3-烷基,C1-C2-卤代烷基或C2-C3-卤代链烯基可选择取代的C3-C6-环烷基,C3-C6-环烷氧基或C3-C6-环烷基-C1-C2-烷氧基,或代表苯基,
其可被相同或不同的取代基可选择地单取代或双取代,取代基为由卤素,C1-C4-烷基,C1-C3-卤代烷基,C1-C4-烷氧基或C1-C4-卤代烷氧基组成的一系列基团,或代表NHR5基。
R5更优选地代表C1-C4-烷基,各自可被相同或不同的取代基可选择地单取代或双取代的苯基或苄基,取代基为由氟、氯、溴,C1-C4-烷基,C1-C4-卤代烷基或C1-C4-卤代烷氧基组成的一系列基团。
X更优选地代表氟,氯或溴。
m更优选地代表0或1。
n更优选地代表1。
R更特别优选地代表R1或R2,其中
R1代表下述基团之一:-CHF2,-CClF2,-CF2CHFCl,-CF2CH2F,-CF2CHF2,-CF2CCl3,-CF2CHFCF3,-CH2CF3,-CH2CF2CHF2,-CH2CF2CF3,
和
R2代表氢,或代表丙烯基,丁烯基,戊烯基,己烯基,丙炔基,丁炔基,戊炔基,
或代表下述任一个基团:
或代表环链烯基烷基:
或代表下述任一个苯基烷基:
或代表
或代表下述任一个杂芳基烷基:
或代表-COR3基。
R3最特别优选地代表甲基,乙基,丙基;
或代表甲氧基,乙氧基,丙氧基,丁氧基;
或代表环丙基,环己基;
或代表环己氧基;
或代表苯基,2-氯苯基,3-氯苯基,2,6-二氟苯基,2-三氟甲氧苯基,4-三氟甲氧苯基;2,4-二氯苯基;3,4-二氯苯基;
或代表-NHR5基。
R5最特别优选地代表甲基,乙基,或代表可被氯可选择地单取代的苯基。
X最特别优选地代表氟氯或溴。
m最特别优选地代表0或1。
n最特别优选地代表1。
其它优选的化合物是那些式(Ic)的化合物
其中
R1,X和m具有上述一般地,优选地,更优选地或最特别优选的定义。
根据本发明化合物的定义在上述已述及的烃基,如烷基或链烯基,在直链或支链的各种情况下,尽可能地,还可与杂原子如烷氧基连接。
上述基团的定义或解释,已述及的一般或其中优选的范围,根据需要彼此可以组合,即各自范围和优选范围之间的组合范围也是可能的。它们使用了类似的终产物以及前体和中间体。
根据本发明优选的是上述优选(优选的)定义组合的那些式(I)化合物。
根据本发明更优选的是上述更优选定义组合的那些式(I)化合物。
根据本发明本发明更特别优选的是上述更特别优选定义组合的那些式(I)化合物。
例如,如果根据方法Aα),将4-羟基联二苯和三氟氯乙烯用作起始物,根据本发明方法的进程可用下式表示:
例如,如果根据方法Aβ),将4-羟基联二苯和三氟溴甲烷用作起始物,根据本发明方法的进程可用下式表示:
例如,如果根据方法Aγ),将4-二氟甲氧苯胺用作起始物,根据本发明方法的进程可用下式表示:
例如,如果根据方法Aδ),将4-羟基联二苯用作起始物,根据本发明方法的进程可用下式表示:
例如,如果根据方法Bα),将4-二氟氯甲氧基联二苯用作起始物,根据本发明方法的进程可用下式表示:
例如,如果根据方法Bβ),将4-乙酰基-4′-羟基联二苯和六氟环丁烯用作起始物,根据本发明方法的进程可用下式表示:
例如,如果根据方法Bγ),将4-乙酰基-4′-羟基联二苯和氯二氟甲烷用作起始物,根据本发明方法的进程可用下式表示:
例如,如果根据方法Cα),将4-乙酰基-4′-二氟甲氧基联二苯用作起始物,根据本发明方法的进程可用下式表示:
例如,如果根据方法Cβ),将4-二氟氯甲氧基联二苯和氯乙酰氯用作起始物,根据本发明方法的进程可用下式表示:
例如,如果根据方法D),将4-氯乙酰基-4′-二氟甲氧基联二苯用作起始物,根据本发明方法的进程可用下式表示:
例如,如果根据方法E),将4-羟基乙酰基-4′-二氟氯甲氧基联二苯用作起始物,根据本发明方法的进程可用下式表示:
例如,如果根据方法F),将4-羟基乙酰基-肟O-甲基醚4′-三氟氯乙氧基联二苯用作起始物,根据本发明方法的进程可用下式表示:
例如,如果根据方法Gα),将2-氨基-2-(4′-二氟氯甲氧基联二苯)-4)-乙-1-醇用作起始物,根据本发明方法的进程可用下式表示:
例如,如果根据方法Gβ),将N-(羧甲基氯甲基)-2,6-二氟苯甲酰胺和4-二氟甲氧基联二苯用作起始物,根据本发明方法的进程可用下式表示:
例如,如果根据方法Hα),将N-(1-(4′-二氟甲氧联二苯基-4-)-乙基-2-醇)-2,6-二氟苯甲酰胺和亚硫酰氯用作起始物,根据本发明方法的进程可用下式表示:
例如,如果根据方法Hβ),将N-1-甲氧基-2-氯乙基)-2,6-二氟苯甲酰胺和4-二氟甲氧基联二苯用作起始物,根据本发明方法的进程可用下式表示:
例如,如果根据方法I),将N-(1-(4′-二氟甲氧基联二苯-4-)2-氯乙基)-2,6-二氟苯甲酰胺用作起始物,根据本发明方法的进程可用下式表示:
例如,如果根据方法J),将2-(2,6-二氟苯基)-4-(4′-叔丁基羰基氧联苯基-4-)-2-噁唑啉用作起始物,根据本发明方法的进程可用下式表示:
例如,如果根据方法Kα),将2-(2,6-二氟苯基)-4-(4′-羟基联苯基-4-)-2-噁唑啉和氯甲酸乙酯用作起始物,根据本发明方法的进程可用下式表示:
例如,如果根据方法Kβ),将2-(2,6-二氟苯基)-4-(4′-羟基联苯基-4)-2-噁唑啉和三氟氯乙烯用作起始物,根据本发明方法的进程可用下式表示:
例如,如果根据实例Kγ),将2-(2,6-二氟苯基)-4-(4′-羟基联苯基-4)-2-噁唑啉和三氟氯甲烷用作起始物,根据本发明方法的进程可用下式表示:
例如,如果根据实施例Kδ),将2-(2,6-二氟苯基)-4-(4′-羟基联苯基-4)-2-噁唑啉和四氯化碳用作起始物,根据本发明方法的进程可用下式表示:
例如,如果根据实例Kε),将2-(2,6-二氟苯基)-4-(4′-羟基联苯基-4)-2-噁唑啉和烯丙基溴用作起始物,根据本发明方法的进程可用下式表示:
进行根据本发明的方法Aα)中所需要的起始物式(III)化合物是已知的和/或可通过简单的已知方法制备的。
例如,制备式(III)化合物可通过磺化可选择取代的联二苯,然后使产物与碱金属氢氧化物反应得到羟基联二苯,或者通过氨基联二苯的重氮化作用并蒸发产物(参见,例如,Houben-Weyl,VI/lc卷(1976),216和251页)而获得。
进行根据本发明的方法Aα),Bβ)和Kβ)中还需要的起始物式(IV)化合物是已知的,和/或可通过简单的已知方法制备的(参见,例如,Houben-Weyl,V/3卷(1962),187页等,317,346页以及下列等等,和377页等)。
进行根据本发明方法Aβ)和Kγ)中需要的起始物式(V)的二氟卤代甲烷是有机化学中一般已知的化合物。
进行根据本发明方法Aγ)中需要的起始物式(VI)化合物是已知的,和/或通过简单已知方法制备的。
例如式(VI)化合物是通过还原相应的硝基芳族化合物或处理相应的甲酰胺,例如,进行霍夫曼重排制得的。
进行根据本发明的方法(β)时需要的起始物式(IX)的卤代乙酰氯是有机化学中常用的,公知的化学品。
进行根据本发明的方法E)时需要的化合物(XII)是有机化学中公知的化学品。
进行根据本发明的方法Gβ)时需要的起始物式(XV)化合物是已知的,和/或可通过简单的已知方法制备的(参见,例如,WO 93/24 270)。
进行根据本发明的方法Hβ)时需要的起始物式(XVIII)化合物是已知的,和/或可通过简单的已知方法制备的(参见,例如,EP-A-0 594 179)。进行根据本发明的方法Hβ)时还需要的起始物式(IIe)化合物是已知的,和/或可通过简单的方法制备的,例如通过相应的羟基联二苯的酰化作用。
进行根据本发明的方法Kα)时需要的起始物式(XIX)化合物是有机化学中公知的化合物。
进行根据本发明的方法Kε)时需要的起始物式(XX)化合物是有机化学中公知的化合物。
M代表常规的离去基,如果R2定义为-COR3,M优选代表卤素,特别例如氯或溴,酸酐和咪唑烷基,如果R2为上述其它定义,M优选代表卤素,特别例如,氯或溴,烷基磺酰氧基,特别例如,甲基磺酰氧基;和可选择取代的芳基磺酰氧基,特别例如,苯基磺酰氧基,对氯苯基磺酰氧基,或甲苯基磺酰氧基。
式(Ia),(Ib),(II),(IIa),(IIb),(IIc),(IId),(VII),(VIIa),(VIIb),(VIII),(X),(XI),(XIII),(XIV),(XVI)和(XVII)的中间体是新的,且也是本发明的主题。在一些情况下,它们本身具有杀虫和杀螨的性质,例如式(Ia),(Ib),(XIV)和(XVII)的化合物。
方法Aα)用于制备式(IIa)化合物,它包括一种方法,其中式(III)化合物与式(IV)化合物进行反应,如果适宜反应在碱存在下,如果适宜,在催化剂存在下和如果适宜,在稀释剂存在下进行,且如果适宜,随后氢化产物。
可以使用的稀释剂是各种常规溶剂。可优选使用的物质例如为腈类,如乙腈和丁腈,或醚类,如甲基叔丁基醚,甲基叔戊基醚,二异丙基醚,1,2-二甲氧乙烷,四氢呋喃和二噁烷。
可以使用的碱是各种常规的质子接受体。可述及的实例为叔胺,如三乙胺,吡啶,二氮杂二环辛烷(DABCO),二氮杂二环十一烷(DBU),以及碱金属氢氧化物和碱土金属氢氧化物。可优选使用的物质是碱金属氢氧化物,特别是氢氧化钠或氢氧化钾,所有的物质还可以水溶液的形式使用。
可使用相转移催化剂作为催化剂,可述及的实例为季铵盐,如溴化四辛基铵和氯化苄基三乙基铵。
反应温度可在很大范围内变化。通常,本方法在20℃至100℃,优选25℃至70℃的温度下进行。
通常,反应在大气压力下或加压进行。通常,反应在1巴至25巴,优选1巴至6巴的压力下进行。
碱与式(III)起始物的比例可在相当大的范围内变化。原则上,需要催化量的碱,但也可使用等摩尔量或过量的碱。通常对每摩尔的式(III)化合物使用0.1至5mol,优选0.5至2mol的碱。
通常,本发明如下述进行,将式(III)化合物和碱加入到稀释剂中,达到所需的反应温度,并计量加入大约等摩尔量的式(IV)烯烃。
如果本方法在密封的容器或在高压釜中进行,可获得一定的内压,且通过通入惰性气体,例如,氮气,可将该压力提高。
以常规的方法对反应混合物进行加工处理,例如,通过提取或过滤。
通过一个附加的反应,开链的式(IV)化合物与式(III)化合物反应。
通过取代反应,式(IV)的环化合物与式(III)化合物在双链反应,随后可氢化剩下的双链,例如,如果适合,用贵金属催化剂,例如铂或钯存在下的氢气(如果需要在加压条件下)氢化。氢化作用优选在稀释剂中进行,适合的稀释剂是各种常规溶剂,例如,(卤代)烃类,醚类和醇类,如果Y代表氟或氯,优选使用质子惰性溶剂。
方法Aβ)制备式(IIb)化合物时包括的方法,其中式(III)化合物与式(V)的二氟卤代甲烷反应,如果适宜反应在碱存在下,如果适宜在催化剂存在下且如果适宜在稀释存在下进行。
可以使用的稀释剂是各种常规溶剂。可优选使用的物质例如为腈类,如乙腈和丁腈,或醚类,如甲基叔丁基醚,甲基叔戊基醚,二异丙基醚,1,2-二甲氧乙烷,四氢呋喃和二噁烷,或醇类,如乙醇,丙醇异构体或丁醇异构体。
可以使用的碱是各种常规的质子接受体。下述碱可被优选地使用:碱金属氢氧化物,如氢氧化钠或氢氧化钾,各种碱也可以水溶液的形式使用。
可使用相转移催化剂作为催化剂,可述及的实例为季铵盐,如溴化四辛基铵和氯化苄基三乙基铵,和磷鎓盐,如四丁基溴化鏻。
反应温度可在相当大的范围内变化。通常,本方法在20℃至150℃,优选40℃至100℃的温度下进行。
通常,反应在大气压力下或加压进行。通常,本方法在1巴至25巴,优选1巴至10巴的压力下进行。
碱与式(III)起始物的比例可在相当大的范围内变化。通常对每摩尔的式(III)化合物使用1至10mol,优选1-5mol的碱。
通常以过量5-倍使用式(V)的二氟卤代甲烷。
方法Aγ)用于制备式(IIc)化合物,包括一种方法,其中将式(VI)的化合物重氮化,且在酸和铁粉存在下,或在碱存在下,如果适宜,在稀释剂存在下使产物与苯反应。
适合的稀释剂为各种惰性溶剂。可选择地,对每摩尔的式(VI)化合物,可使用大量过量的反应物苯作为稀释剂,优选苯的量为≤30mol,更优选地为≤5mol。
如果反应在酸和铁粉的存在下进行,则适合的酸优选为有机酸如三氯乙酸。
如果反应在碱存在下进行,适合的碱例如为有机酸盐,如碱金属乙酸盐,特别是乙酸钠或乙酸钾。
通常使用二当量的碱。
反应温度可在相当大的范围内变化。通常本方法在-40℃至140℃,优选在-20℃至80℃的温度下进行。
反应通常在大气压力下进行。
通常,重氮盐是从酸,如盐酸或硫酸存在下的式(VI)化合物,以常规的方法通过与碱金属亚硝酸盐,如亚硝酸钠,或亚硝酸烷基酯,如亚硝酸苯酯或亚硝酸甲酯反应,或通过与亚硝酰氯反应而制备的。
含有式(IIc)产物的反应混合物是借助常规方法加工处理的。
方法Aδ)用于制备式(IId)化合物包括一种方法,其中式(III)化合物在无水氢氟酸存在下,如果适宜在稀释剂存在下与四氯化碳反应。
适合的稀释剂是惰性有机溶剂。优选使用过量2至3倍的四氯化碳作为稀释剂。
无水氢氟酸的量可在很大范围内变化。通常对每摩尔的式(III)化合物使用2至40mol,优选5至20mol的无水氢氟酸。
反应温度可在很大范围内变化。通常,本方法在60℃至150℃,优选80℃至125℃的温度下进行。
通常,方法如下述进行,在高压釜中,将式(III)化合物与四氯化碳和无水氢氟酸混合,将混合物加热到所需温度并在有力的压力下搅拌。
在加工后处理中,例如采用蒸馏的方法,分离掉反应混合物中较高挥发性的成分,如氢氟酸,氟利昂和过量的四氯化碳。
剩余物用合适的惰性溶剂吸收,用碱冲洗混合物并通过蒸馏纯化。
方法Bα)用于制备式(VII)化合物,包括一种方法,其中在酸或路易斯酸的存在下和在稀释剂存在下,式(II)化合物与乙酰氯反应。
适合的稀释剂是合适于弗瑞德-克来福次反应的各种常规溶剂,优选使用氯化烃,例如二氯甲烷或二氯乙烷。
适合的酸或路易酸是适合于弗瑞德-克来福次反应的各种酸。优选使用氯化铝,无水氢氟酸,四氟硼酸或BF3醚合物。
反应温度可在很大范围内变化。通常,本方法在-30℃至80℃,优选-15℃至50℃的温度下进行。
反应通常在大气压力下或升压下进行。
通常使用大约等摩尔量的乙酰氯和式(II)化合物。
当反应结束时,用常规的方法对产物加工处理。
方法Bβ)用于制备式(VIIa)化合物,包括一种方法,其中式(IIIa)化合物与式(IV)化合物反应,如果适宜,反应在碱存在下,如果适宜,在催化剂存在下和如果适宜,在稀释剂存在下进行,且如果适宜,随后氢化混合物。
对于碱,催化剂,稀释剂和其它反应条件,在方法Aα)中已描述过的都适用于本方法。
方法Bγ)用于制备式(VIIb)化合物,包括一种方法,其中式(IIIa)化合物与式(V)化合物反应,如果适宜,反应在碱存在下,如果适宜,在催化剂存在下和如果适宜,在稀释剂存在下进行。
对于碱,催化剂,稀释剂和其它反应条件,在方法Aα)中已描述过的都适用于本方法。
方法Cα)用于制备式(VIII)化合物,包括一种方法,其中如果适合,在稀释存在下氯化或溴化式(VIII)化合物。
适合的稀释剂是对氯或溴惰性的各种溶剂,优选使用的稀释剂的实例为烃类,如二氯甲烷,氯仿或四氯化碳,或醇类如甲醇或乙醇。
反应温度可在相当大的范围内变化。通常,本方法在-30℃至50℃,优选-10℃至25℃的温度下进行。
反应通常在大气压力下进行。
通常,本方法如下述进行,将式(VI)化合物导入到适合稀释剂中,然后在所需温度下,计量加入大约等摩尔量的氯或溴。还可能使用少量过量,或稍不足于化学计算量的卤素。
方法Cβ)用于制备式(VIII)化合物,包括一种方法,其中在酸或路易斯酸存在下和在稀释剂存在下,由式(II)化合物与式(IX)卤代乙酰氯反应。
适合的稀释剂是合适于弗瑞德-克来福次反应的各种常规溶剂,优选使用氯化烃,例如二氯甲烷或二氯乙烷。
适合的酸或路易酸是适合于弗瑞德-克来福次反应的各种酸。优选使用氯化铝或四氟硼酸。
反应温度可在很大范围内变化。通常,本方法在-30℃至50℃,优选-15℃至30℃的温度下进行。
反应通常在大气压力下或升压下进行。
通常使用大约等摩尔量的式(IX)卤代乙酰氯和式(II)化合物。
当反应结束时,用常规的方法对产物加工处理。
方法D)用于制备式(X)化合物,包括一种方法,其中式(VIII)化合物与甲酸的盐反应,如果适合反应在催化剂存在下进行。
适合的稀释剂是在反应条件下惰性的各种常规的溶剂,优选使用下述的:烃类,如甲苯二甲苯,,环己烷,甲基环己烷,氯代烃类,如氯苯,对二氯苯,四氯化碳,醇类,如甲醇,乙醇,丙醇异构体,丁醇异构体和戊醇异构体,醚类,如二异丙基醚,四氢呋喃,二噁烷,腈类,如乙腈和丁腈,酰胺类,如二甲基甲酰胺,还有强极性溶剂,如二甲基亚砜和环丁砜。
如果适宜,上述稀释剂还可以以与水的混合物形式使用,如果适宜,可存在相转移催化剂,例如:季铵盐类,如溴化四辛基铵或氯化苄基三乙基铵。
可优选使用的甲酸盐为甲酸钠和甲酸钾。
反应温度可在很大范围内变化。通常,本方法在50℃至200℃,优选80℃至160℃的温度下进行。
通常,本方法如下述进行,将式(VIII)化合物与1至20mol,优选1至5mol的甲酸盐在稀释剂中加热,然后,如果适宜,加入水,进行相分离,蒸馏掉稀释剂。
方法E)用于制备式(XI)化合物,包括一种方法,其中式(X)化合物与式(XII)化合物反应,如果适宜反应在稀释剂存在下进行。
适合的稀释剂是各种常规的溶剂。优选使用的稀释剂的实例为醇类,如甲醇,乙醇,丙醇异构体,丁醇异构体和戊醇异构体,醚类,如二异丙基醚,四氢呋喃,二噁烷,如果适宜,所有的溶剂可以其和水的混合物的形式使用。
式(XII)的O-甲基羟基胺可以其游离碱的形式或者以其酸盐的形式使用。在第二种情况中本方法在碱,优选乙酸钠的存在下进行。式(XII)化合物通常以等摩尔量使用。
反应温度可在很大的范围内变化。通常本方法在-20℃至100℃,优选0℃至60℃的温度下进行。
本方法通常在大气压力下进行。
以常规方法,例如通过过滤或提取,进行加工处理。
方法F)用于制备式(XIII)化合物,包括一种方法,其中在酸存在下,如果适宜在稀释剂存在下,式(XI)化合物与还原剂反应。
适合的稀释剂是对反应物情性的各种溶剂,优选使用的稀释剂是醚类,例如,二异丙基醚,甲基叔丁基醚,四氢呋喃,1,2-二甲氧基乙烷和二噁烷。
优选的还原剂是以等摩尔量或过量使用的硼酸钠。
优选的酸是以等摩尔量或过量使用的三氟乙酸。
反应温度可在相当大的范围内变化。通常反应开始在0℃至50℃的温度下进行,在反应过程中提高温度,如果适宜升至120℃。
反应通常在大气压力下进行。
借助常规的方法进行加工处理。
优选以盐的形式分离式(XIII)反应产物,例如盐酸盐。
方法Gα)包括一种方法,其中式(XIII)化合物与2,6-二氟苯甲酰氯,如果适宜在碱存在下,和如果适宜在稀释剂存在下反应。
可使用的稀释剂是对这些化合物惰性的各种溶剂。优选使用下述的:烃类,如汽油,苯,甲苯,二甲苯和1,2,3,4-四氢化萘,还有卤代烃类,如二氯甲烷,氯仿,四氯化碳,氯苯和对二氯苯,还有酮类,如丙酮和甲基异丙基酮,还有醚类,如***,四氢呋喃和二噁烷,还有羧酸酯类,如乙酸乙酯,还有强极性溶剂,如二甲基亚砜和环丁砜。如果酰基卤对水解足够稳定,反应还可在水存在下进行。
在反应中适合的碱是各种常规酸吸收剂。优选使用下述的:季胺类,如三乙基胺,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,还有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,和碱金属氢氧化物或碱土金属氢氧化物,如氢氧化钠或氢氧化钾。
反应温度可在相当大的范围内变化。通常反应在-20℃至+100℃,优选在0℃至30℃的温度下进行。
反应通常在大气压力下进行。
进行本方法时,通常使用大约等摩尔量的式(XIII)起始物和2,6-二氯苯甲酰氯。可是还可能使用大量过量(多至5mol)的羧酰基卤。通过常规方法进行加工处理。
方法Gβ)用于制备式(XIV)化合物,包括一种方法,其中(步骤1)在酸性催化剂存在下,和如果适宜在稀释剂存在下,由式(II)化合物首先与式(XV)化合物反应,然后(步骤2)在稀释剂存在下,所得的式(XVI)化合物与还原剂反应。
适合第一步的稀释剂是对反应物惰性的各种溶剂。
优选使用下述的:烃类,如甲苯,二甲苯,1,2,3,4-四氢化萘,卤代烃类如二氯甲烷,氯仿,氯苯,对二氯苯,醚类如二异丙基醚,甲基叔丁基醚,四氢呋喃,二噁烷,二甲氧乙烷,酮类如丙酮或甲基乙基酮,醇类如甲醇,乙醇和丙醇,酰胺类如二乙基甲酰胺,和亚砜类如二甲基亚砜。
原则上,适合的酸性催化剂是各种无机酸或有机酸或路易斯酸。优选使用的酸的实例为硫酸,甲磺酸,苯磺酸,氯化铝,四氯化钛,三氯氧化磷,三氟化硼醚合物。如果适合,过量的酸也可用作稀释剂。
反应温度可在很大范围内变化。通常,本方法在-20℃至150℃,优选在0℃至50℃的温度下进行。
反应通常在大气压力下进行。
通常以等摩尔量使用式(II)化合物和式(XV)化合物,但是也可能使用过量的一种或另一种化合物。
在第二步中特别适合的稀释剂是醇类和醚类。可述及的实施例是甲醇,乙醇,丙醇异构体,丁醇异构体和戊醇异构体,还有***,二异丙基醚,甲基叔丁基醚,四氢呋喃,二噁烷和二甲氧基乙烷。
对每mol的式(XVI)化合物,优选使用1至5mol的还原剂硼氢化钠。
如果式(XVI)化合物是一种酸(R6=H)形式,在与硼氢化钠进行反应之前,必须将该酸转化成烷基酯。
反应温度可在很大的范围内变化。通常,本方法在20℃至150℃,优选50℃至100℃的温度下进行。
通常反应在大气压力下进行。
借助常规方法加工处理产物。
方法Hα)用于制备式(XVII)化合物,包括一种方法,其中式(XIV)化合物与氯化剂反应,如果适宜反应在稀释剂存在下进行。
适合的稀释剂是各种惰性有机溶剂。优选使用的稀释剂是烃类如甲苯,二甲苯,己烷,环己烷,卤代烃类如氯苯,氯仿,二氯甲烷,和醚类如***,二异丙基醚,二甲氧乙烷,四氢呋喃和二噁烷。
适合的氯化剂是常规用于此目的的各种反应物。可述及的实施例是硫酰氯,光气和三氯氧化磷,通常至少以等摩尔量使用这些氯化剂。
反应温度可在很大范围内变化。通常,本方法在0℃至120℃,优选20℃至100℃的温度下进行。
如果适宜,反应在碱,特别是季胺,如三乙基胺或吡啶存在下反应。
方法Hβ)用于制备式(XVII)化合物,包括一种方法,其中在酸催化剂存在下和如果适宜在稀释剂存在下式(II)或(IIe)化合物与式(XVIII)化合物反应。
适合的稀释剂是对反应物惰性的各种溶剂。
优选使用下述的:烃类,如甲苯,二甲苯,1,2,3,4-四氢化萘,卤代烃类如二氯甲烷,氯仿,氯苯,对二氯苯,醚类如二异丙基醚,甲基叔丁基醚,四氢呋喃,二噁烷,二甲氧乙烷,酮类如丙酮或甲基乙基酮,醇类如甲醇,乙醇和丙醇,酰胺类如二乙基甲酰胺,和亚砜类如二甲基亚砜。
原则上,适合的酸性催化剂是各种无机酸或有机酸或路易斯酸。优选使用的酸的实例为硫酸,甲磺酸,苯磺酸,无水氢氟酸,氯化铝,四氯化钛,三氯氧化磷,三氟化硼醚合物。如果适合,过量的酸也可用作稀释剂。
反应温度可在很大范围内变化。通常,本方法在-20℃至150℃,优选在0℃至80℃的温度下进行。
反应通常在大气压下或升压下进行。
通常,以等摩尔量使用式(II)或式(IIe)化合物和式(XVIII)化合物;可是也可过量使用一种或另一种化合物。
方法I)用于制备式(I)化合物,包括一种方法,其中,在碱存在下使式(XVII)化合物环化,如果适宜在催化剂存在下,且如果适宜在稀释剂存在下进行反应。
适合的稀释剂是各种有机溶剂。如果适宜,它们可以以与水的混合物形式使用。优选使用下述的:烃类如甲苯,二甲苯,1,2,3,4-四氢化萘,己烷,环己烷,卤代烃类如二氯甲烷,氯仿,氯苯,对二氯苯,醇类如甲醇,乙醇,乙二醇,丙醇异构体,丁醇异构体和戊醇异构体,醚类如***,二异丙醚,二甲氧乙烷,四氢呋喃,二噁烷,腈类如乙腈或丁腈,酰胺类如二甲基甲酰胺,亚砜类如二甲基亚砜,还有环丁砜。特别优选使用醇类。
适合的碱是各种常用的酸接受剂。
优选使用下述的:叔胺如三乙基胺,吡啶,DABCO,DBU,DBN,N,N-二甲基苯胺,还有碱土金属氧化物如氧化镁和氧化钙,另外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,碱金属氢氧化物如氢氧化钠和氢氧化钾,还有醇化物如乙醇钠或叔丁基化钾。
如果适宜,本方法在相转移催化剂存在下进行。适合的相转移催化剂的实例是铵化合物,如溴化四辛基铵或氯化苄基三乙基铵。
反应温度可在很大范围内变化。通常本方法在-10℃至150℃,优选在0℃至100℃的温度下进行。
反应通常在常压下进行。
通常,使用等摩尔量的碱。可是,还可能使用过量的碱。
以常规方法进行加工处理。
方法J用于制备式(Ib)化合物,其特征在于水解式(Ia)化合物。
方法J优选在稀释剂存在下进行。优选使用的稀释剂是水/醇混合物,例如,水/甲醇,水/乙醇或水/丙醇,或水/酰胺,例如,水/二甲基甲酰胺(DMF)或水/二甲基乙酰胺。
方法J)在碱存在下进行。适合的碱是无机碱和有机碱,特别是碱金属氢氧化物,如氢氧化钠或氢氧化钾,或氨。
反应温度可在很大范围内变化。通常,本方法在-10℃至60℃,优选0℃至40℃的温度下进行。反应通常在大气压力下进行。
方法Kα)的特征在于式(Ib)化合物与式(XIX)化合物反应,如果适宜在稀释剂存在下,和如果适宜在碱存在下进行反应。
可使用的稀释剂是对这些化合物惰性的各种溶剂。优选使用下述的:烃类,如汽油,苯,甲苯,二甲苯和1,2,3,4-四氢化萘,还有卤代烃类,如二氯甲烷,氯仿,四氯化碳,氯苯和对二氯苯,还有酮类,如丙酮和甲基异丙基酮,还有醚类,如***,四氢呋喃和二噁烷,还有羧酸酯类,如乙酸乙酯,还有强极性溶剂,如二甲基亚砜和环丁砜。如果酰基卤对水解足够稳定,反应还可在水存在下进行。
适合于反应的酸接合剂是各种常规的酸接受剂。优选使用下述的:季胺类,如三乙基胺,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),Hunig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,还有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,和碱金属氢氧化物或碱土金属氢氧化物,如氢氧化钠或氢氧化钾。
反应温度可在相当大的范围内变化。通常反应在-20℃至+100℃,优选在0℃至30℃的温度下进行。
反应通常在大气压力下进行。
进行本方法时,通常使用大约等摩尔量的式(Ib)和(XIX)起始物。可是还可能使用大量过量(多至5mol)的式(XIX)化合物。通过常规方法加工处理。
方法Kβ)的特征在于式(Ib)化合物与式(IV)化合物反应,如果适宜反应在碱存在下,如果适宜在催化剂存在下,和如果适宜在稀释剂存在下进行,和如果适宜随后氢化产物。
使用类似于上述方法Aα)中的有关稀释剂,碱,催化剂,温度压力,对式(Ib)起始物的碱的比例进行本方法并加工处理产物。
方法Kγ)的特征在于式(Ib)化合物与式(V)的二氟卤代甲烷反应,如果适宜反应在碱存在下,如果适宜在催化剂存在下且如果适宜在催化剂存在下进行。
使用类似于上述方法Aβ)中有关的稀释剂,碱,催化剂,温度,压力和有关物质的重量比。
方法Kδ)的特征在于式(Ib)化合物与四氯化碳在盐酸存在下反应,如果适宜反应在稀释剂存在下进行。
使用类似于上述方法Aδ)中有关的稀释剂,氢氟酸量,温度,进行本方法和加工处理产物。
方法Kε)的特征在于式(Ib)化合物与式(XX)化合物反应,如果适宜反应在稀释剂存在下和如果适宜在碱存在下进行。
适合的稀释剂是各种常规溶剂。优选使用下述的:可选择卤化的,芳族烃或脂肪烃,酮类,腈类和酰胺类。可述及的实例为甲苯,丙酮,乙腈,二甲基甲酰胺和二甲基乙酰胺。
适合的碱是各种常规的无机碱和有机碱,可述及的实例是叔胺如三乙胺,DBN,DBU,DABCO,碱金属氢氧化物和碱土金属氢氧化物,例如,氢氧化钠,氢氧化钾和氢氧化钙,还有碱金属碳酸盐和碱土金属碳酸盐,例如,碳酸钠或碳酸钾。
反应温度可在很大范围内变化。通常,本方法在-20℃至100℃,优选0℃至60℃的温度下进行。
反应通常在大气压力下进行。
通常,以大约等摩尔量使用式(Ib)化合物和式(XX)化合物。可是,还可能应用过量的式(XX)化合物。
该活性化合物适用于防治有害动物,特别是农业、林业、储物防护、兽医及卫生领域中的节肢动物和线虫,尤其是有害的昆虫和蜘蛛类。该化合物能有效地防治一般敏感的和有抗性的种类,并能防治所有各虫期的害虫(或这些害虫的某些发育阶段)。上述害虫包括:
等足目,如潮虫,平甲虫和鼠帚。
倍足亚纲,如具斑马陆。
唇足纲,如食果地蜈蚣和蚰蜒属的种类。
综合纲,如庭院么蚰。
缨尾目,如西洋衣鱼。
弹尾目,如具剌跳虫。
直翅目,如东方蜚蠊,美洲大蠊,马得拉蜚蠊,德国小蠊,家蟋蟀,蝼蛄属的种类,热带飞蝗,殊种蚱蜢,荒地蚱蜢和蜚蠊属(Supella)的种类。
革翅目,如欧洲球螋。
等翅目,如白蚁属的种类。
虱目,如葡萄根瘤蚜,绵蚜属的种类,头虱属的种类,体虱属的种类,血虱属的种类,长颚虱属的种类和盲虱属的种类。
食毛目,如嚼虱属的种类,畜虱属的种类,毛羽虱属种类,皮羽虱属种类,毛虱属的种类,羽虱属的种类,绿领虱属种类,鳞角虱属种类和兽羽虱属的种类。
缨翅目,如温室条蓟马和葱蓟马。
异翅亚目,如褐盾蝽属的种类,介中红蝽,方背皮蝽,温带臭虫,长红蜡蝽,猎蝽属的种类和全坚蝽属的种类。
同翅亚目,如甘蓝粉虱,木薯粉虱,温室粉虱,棉蚜,甘蓝蚜,茶麓隐瘤蚜,甜菜蚜,波密角蚜,苹果绵蚜,桃大尾蚜,麦长管蚜,瘤蚜属的种类,忽布疣蚜,禾谷缢管蚜,小绿叶蝉属的种类,双叶叶蝉,黑尾叶蝉,李蜡蚧,油榄黑盔蚧,灰飞虱,稻褐飞虱,红圆蚧,夹竹桃圆蚧,粉蚧属的木虱属的种类。
鳞翅目,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,棕尾毒蛾,舞毒蛾属的种类,棉叶穿孔潜蛾,桔细潜蛾,地老虎属的种类,切根虫属的种类,夜蛾属种类,埃及金刚钻,实夜蛾属的种类,甜菜夜蛾,甘蓝夜蛾,松夜蛾,斜纹夜蛾,粘虫属的种类,粉纹夜蛾,苹果蠹蛾,菜粉蝶属的种类,螟属的种类,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;云杉卷叶蛾,葡萄果蠹蛾,茶长卷蛾和栎绿卷叶蛾。
鞘翅目,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,叶甲属的种类,油菜兰跳甲,墨西哥豆瓢虫,隐食甲属的种类,锯谷盗,花象甲属的种类,谷象属的种类,葡萄黑象甲,香蕉蛀基象甲,甘蓝夹象甲,苜蓿叶象甲,皮蠹属的种类,斑皮蠹属的种类,圆皮蠹属的种类,毛皮蠹属的种类,粉蠹属种类,油菜花露尾甲,蛛甲属的种类,金黄蛛甲,麦蛛甲,拟谷盗属的种类,大黄粉虫,叩甲属的种类,金针虫属种类,西方五月鳃角金龟子,六月金龟子和褐新西兰肋翅鳃角金龟子。
膜翅目,如锯角叶蜂属的种类,叶蜂属的种类,蚁属的种类,厨蚁和胡蜂属的种类。
双翅目,如伊蚊属的种类,按蚊属的种类,库蚊属的种类,黄猩猩果蝇,家蝇属种类,厕蝇属种类,丽蝇属种类,绿蝇属种类,金蝇属种类,疽蝇属种类,胃蝇属种类,虱蝇属种类,厩螯蝇属种类,狂蝇属种类,皮蝇属种类,虻属种类,螗蜩属种类,花圈毛蚊,瑞典麦杆蝇,草种蝇属种类,藜花蝇,地中海实蝇,油榄实蝇,欧洲大蚊,蚋属种类,真蚋属种类,白蛉属种类,路蛉属种类,蠓属种类,斑虻属种类,瘤虻属种类,黄虻属种类,虻属种类,麻虻属种类,菲虻属种类,蜂蝇属种类,齿股蝇属种类,螫蝇属种类,血蝇属种类,莫蝇属种类,厕蝇属种类,螯螯蝇属种类,丽蝇属种类,污蝇属种类,麻蝇属种类,狂蝇属种类,皮蝇属种类,胃蝇属种类,虱蝇属种类,羊虱蝇属种类,蜱蝇属种类和腐蝇属种类。
蚤目,如客蚤属种类,角叶蚤属种类,蚤属种类和栉首蚤属种类。
蛛形纲,如蝎和盗蛛。
蜱螨目,如癣螨属种类,耳痒螨属种类,粗脚粉螨,锐缘蜱属种类,钝缘蜱属种类,禽剌螨属种类,皮剌螨属种类,茶藨瘿螨,桔芸锈螨,牛蜱属种类,扇头蜱属种类,花蜱属种类,璃眼蜱属种类,硬蜱属种类,痒螨属种类,皮痒螨属种类,疥螨属种类,附线螨属种类,苜蓿苔螨,全爪螨属种类,叶螨属种类,革蜱属种类,血蜱属种类,剌利螨属种类,肺剌螨属种类,胸孔螨属种类和蜂螨属种类。
前气门亚目和粉螨总科,如盾螨属种类,拒螯螨属种类,禽螯螨属种类,肉螨属种类,生疥螨属种类,蠕形螨属种类,恙螨属种类,螨属种类,粉螨属种类,食酪螨属种类,嗜木螨属种类,颈下螨属种类,翅螨属种类,瘙螨属种类,痒螨属种类,耳癞螨属种类,疥螨属种类,痂螨属种类,疙螨属种类,胞螨属种类和皮膜螨属种类。
本发明的活性化合物具有突出的强力杀虫和杀螨活性。
它们可特别成功地防治对植物有害的昆虫,例如,防治卷叶蛾(Phaedon cochleariae)幼虫或防治黑尾叶蝉(Nephotettixcincticeps)幼虫或防治小菜蛾(Plutella maculipennis)幼虫。
可将活性化合物转化成常规的制剂,如液剂,乳剂,可湿性粉剂,悬浮剂,粉剂,粉尘剂,可溶粉剂,颗粒剂,乳油,活性化合物浸渍的天然和合成材料,和聚合物的微细胶囊。
这些制剂是以已知方法生产的,例如通过将活性化合物与填充剂,即液体溶液和/或固体载体混合,可选择地可使用表面活性剂,即乳化剂和/或分散剂,和/或成泡剂。
在用水作为填充剂时,例如,有机溶剂也可用作助溶剂。适合的液体溶剂主要有,芳烃类,如二甲苯,甲苯或烷基萘,氯化芳烃和氯化脂肪烃类,如氯苯,二氯乙烷或二氯甲烷,脂族烃,如环己烷或链烷烃,例如矿物油馏分,矿物油和植物油,醇类,如丁醇或乙二醇以及它们的醚类和酯类,酮类如丙酮,甲基乙基酮,甲基异丁基酮或环己酮,强极性溶剂,如二甲基甲酰胺和二甲基亚砜,以及水。
适合的固体载体是:例如铵盐和天然矿物颗粒,如高岭土,粘土,滑石,白垩,石英,硅镁土,蒙脱石或硅藻土,和合成矿物颗粒,如高分散二氧化硅,氧化铝和硅酸盐;适合颗粒剂的固体载体是:例如碾碎并分级的天然岩石如方解石,大理石,浮石,海泡石和白云石,以及无机合成颗粒和有机粉末,且有机材料的颗粒如锯末,坚果壳,玉米轴芯和烟茎;适合的乳化和/或成泡剂为: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,例如烷基芳基聚乙二醇醚,烷基磺酸盐,烷基硫酸盐,芳基磺酸盐以及白蛋白水解产物;适合的分散剂为,例如木质素亚硫酸废液和甲基纤维素。
可在制剂中应用的粘着剂如羧甲基纤维素和以粉末,颗粒或胶乳形式的天然和合成聚合物,如***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。其它添加剂可以是矿物油和植物油。
可能使用的着色剂如无机颜料,例如氧化铁,氧化钛和普鲁士兰,和有机染料,如茜素染料,偶氮染料和金属酞菁染料,和痕量营养物如铁,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%。
根据本发明的活性化合物可以其市售制剂或从这些制剂制备的应用形式存在,如与其它活性化合物,如杀虫剂,吸诱剂,消毒剂,杀细菌剂,杀螨剂,杀线虫剂,杀真菌剂,生长调节剂或除草剂的混合物。例如这些杀虫剂特别包括磷酸酯类,氨基甲酸酯类,羧酸酯类,氯化烃类,苯基脲类和通过微生物生产的物质。
特别优选的混合物成分的实例为下述化合物:
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-甲酰苯胺;2,6-二氯-N-(4-三氟甲基苄基)-苯甲酰胺;(E)-2-甲氧亚氨基-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-基氧]-苯基}-3-甲氧丙烯酸甲基酯;(E)-甲氧亚氨基[α-(对甲苯氧基)-对甲苯基]乙酸甲酯;2-苯基酚(OPP),艾敌吗啉,ampropylfos,敌菌灵,戊环唑,
苯霜灵,麦锈灵,苯菌灵,binapacryl,联苯酚,双苯***醇,灭瘟素,糠菌唑,乙嘧酚磺酸酯,粉病定,
多硫化钙,敌菌丹,克菌丹,多菌灵,萎锈灵,灭螨猛,地茂散,氯化苦,百菌清,乙菌利,硫杂灵,霜脲氰,环唑醇,酯菌胺,
双氯酚,苄氯***醇,苯氟磺胺,哒菌清,氯硝胺,乙霉威,噁醚唑,甲菌定,烯酰吗啉,烯唑醇,敌螨普,二苯胺,dipyrithion,灭菌磷二噻农,多果定,敌菌酮,
克瘟散,Epoxyconazole,乙菌克,氯唑灵,
异嘧菌醇,Fenbuconazole,呋菌胺,种衣酯,拌种咯,苯锈啶,丁苯吗啉,薯瘟锡,毒菌锡,福美铁,嘧菌腙,氟啶胺,Fludioxonil,氟菌安,Fluquinconazole,氟硅唑,磺菌胺,氟酰胺,粉唑醇。灭菌丹,乙磷铝,四氯苯酞,麦穗宁,呋氨丙灵,拌种胺,
双胍盐,
氯苯嘧啶醇,己唑醇,土菌消,
烯菌灵,酰胺唑,双胍辛醋酸盐,iprobenfos(IBP),异丙定,富士一号,
春雷霉素,铜制备物如:氢氧化铜,环烷酸铜,氯氧化铜,硫酸铜,氧化铜,8-羟基喹啉铜,和波尔多液混合物,
锰铜混剂,代森锰锌,代森锰,嘧菌胺,灭锈胺,氨丙灵,
metconazol,磺菌威,甲呋菌胺,代森联,嘧菌胺,腈菌唑,
福美镍,异丙消,环菌灵,
甲呋酰胺,噁霜灵,oxamocarb,氧化萎锈灵,稻瘟酯,戊菌唑,戊醇隆,phosdiphen,四氯苯酞,多马霉素,粉病灵,福美锌,多氧霉素,噻菌灵,丙氯灵,杀菌利,百维灵,丙环唑,甲基代森锌,定菌磷,啶斑肟,pyrimethanil,毛醌素五氯硝基苯(PCNB),
硫和硫制剂,
戊唑醇,白叶减,四氯硝基苯,氟醚唑,涕必灵,噻菌腈,甲基托布津,福美双,甲基立枯磷,对甲抑菌灵,唑菌酮,唑菌醇,唑菌嗪,扬菌胺,三环唑,克啉菌,氟菌唑,嗪氨灵,triticonazole,
有效霉素,烯菌酮,代森锌,福美锌。
杀细菌剂:
拌棉醇,双氯酚,四氯草定,福美镍,春雷霉素,octhilinone,furanecarboxylic,羟基喹啉,噻菌灵,链霉素,白叶减,硫酸铜和其它铜制备物。
杀虫剂/杀螨剂/杀线虫剂:
苏云菌杆菌,噁虫威,丙硫克百成,杀虫磺,氟氯氰菊酯,氯氰菊酯,丁苯威,brofenprox,溴硫磷,全杀威,噻嗪酮,丁叉威,哒端酮,硫线磷,西维因,呋喃丹,三硫磷,丁硫克百威,杀螟丹,CGA157419,CGA184699,毒虫畏,定虫隆,氯甲磷,毒死蜱,甲基毒死蜱,顺-苄呋菊酯,clocythrin,四螨嗪,杀螟腈,乙氰菊酯,β-氟氯氰菊酯,三氟氯氰菊酯,三环锡,氯氰菊酯,灭蝇胺,
溴氰菊酯,甲基内吸磷,内吸磷硫赶式异构体,甲基内吸磷硫赶式异构体,杀螨隆,二嗪农,除线磷,敌敌畏,dicliphos,百治磷,乙硫磷,氟脲杀,乐果,甲基毒虫畏,敌杀磷,乙拌磷,克瘟散,emamectin,高氰戊菊酯,苯虫威,乙硫磷,醚菊酯,氯嘧啶磷,克线磷,喹螨醚,杀螨锡,杀螟松,fenobucarb,苯硫威,双氧威,分扑菊酯,fenpyrad,唑螨酯,倍硫磷,氰戊菊酯,fipronil,氟啶胺,氟螨脲,氟氰戊菊酯,氟虫脲,flufenprox,氟胺氰菊酯,地虫磷,安果,噻唑硫磷,呋线威,
六六六,庚虫磷,氟铃脲,噻螨酮,
咪蚜胺,iprobenfos,异唑磷,丙胺磷,异丙威,异噁唑磷,α-三氟氯氰菊酯,lufenuron,马拉硫磷,灭蚜磷,mervinphos,甲丙硫磷,多聚乙醛,虫螨畏,甲胺磷,杀扑磷,灭虫威,灭多威,metolcarb,milbemectin,久效磷,moxidectin,
二溴磷,NC184,NI25,nitenpyram,
氧化乐果,甲叉丙威,吸磷,oxydeprofos,对硫磷,甲基对硫磷,氯菊酯,稻丰散,甲拌磷,伏杀磷,亚胺硫磷,磷胺,辛硫磷,抗蚜威,虫螨磷,乙基虫螨磷,溴丙磷,猛杀威,丙虫磷,残杀威,丙硫磷,发果,pymetrozin,吡唑硫磷,哒嗪硫磷,反灭菊酯,除虫菊酯,哒螨酮,pyrimidifen,蚊蝇醚,
喹硫磷,
RH5992,
杀抗松,克线丹,silafluofen,治螟磷,乙丙硫磷。
tebufenozid,tebufenpyrad,tebupirimiphos,伏虫隆,七氟菊酯,双硫磷,叔丁威,特丁磷,杀虫威,Thiafenox,硫双灭多威,特氨叉威,甲基乙拌磷,治线磷,苏云菌杆菌,四溴菊酯,triarathen,***磷,triazuron,敌百虫,triflumuron,三甲威,
蚜灭多,二甲威,
除草剂:
例如苯胺类,如吡氟草胺,敌稗;芳基羧酸类,例如二氯甲酸,麦草畏和毒莠定;芳氧基链烷酸,例如,2,4-滴,2,4-滴丁酸,2,4-滴丙酸,氟草定,2甲4氯,2甲4氯丙酸和绿草定;芳氧基-苯氧基-链烷酸酯,例如禾草灵,恶唑禾草灵,精吡氟禾草灵,盖草能和喹禾灵;吖嗪酮类,例如杀草敏和达草灭;氨基甲酸酯类,例如氯苯胺灵,异苯敌草,甜菜宁和苯胺灵,氯乙酰苯胺类,例如甲草胺,乙草胺,去草胺,吡草胺,乙基乙草胺,丙草胺和扑草胺;二硝基苯胺类,例如胺磺灵,胺硝草,氟乐灵;二苯基醚类,例如氟锁草醚,甲羧除草醚,乙羧氟草醚,氟磺胺草醚,halosafen,克阔乐和氟硝草醚;脲类,例如绿麦隆,敌草隆,伏草隆,异丙隆,利谷隆和甲基苯噻隆,羟基胺类,例如枯杀达,稀草酮,噻草酮,稀禾定和肟草酮;咪唑啉类,例如咪草烟,咪草酯,灭草烟和灭草喹;腈类,例如溴苯腈,敌草腈和碘苯腈;氧乙酰胺类,例如苯噻草胺;磺酰脲类,例如amidosulfuron,苄嘧磺隆,氯嘧磺隆,绿磺隆,醚黄隆,甲磺隆,烟嘧磺隆,氯嘧磺隆,吡嘧磺隆,赛苯隆,醚苯磺隆和苯磺隆;硫代氨基甲酸酯类,例如苏达灭,草灭特,燕麦敌,扑草灭,禾草畏,草达灭,苄草丹,杀草丹和野麦畏;三嗪类,例如莠去津,草净津,西玛津,西草净,去草净和特丁津;三嗪酮类,例如六嗪同,苯嗪草和喹草酮;其它类例如氨基***,呋草黄,噻草平,恶庚草烷,广灭宁,clopyralid,燕麦枯,氟硫草定,唑草定,氟咯草酮,草铵膦,草甘膦,异恶草胺,达草止,快杀稗,喹草酸,草硫膦和灭草环。
根据本发明的活性化合物可以其市售制剂或从这些制剂制备的应用形式存在,如与增效剂的混合物。增效剂是能够增加活性化合物活性,而加入的增效剂本身不一定具有活性的化合物。
从市售制剂制备的应用形式的活性化合物含量可在很宽范围内变化。应用形式的活性化合物浓度可从按重量计0.0000001至95%的活性化合物,优选按重量计0.0001至1%。
适宜的应用形式是以常规方法使用本化合物。
根据本发明的活性化合物不仅对植物害虫,卫生害虫和贮藏品害虫起作用,而且在兽药领域对动物寄生虫(外寄生虫)如蜱,隐喙螨科,马痒螨,恙螨科,蝇类(剌吸),寄生蝇幼虫,虱,头虱,鸟虱和跳蚤起作用。例如,它们对蜱例如微小牛蜱显示出优越的活性。
根据本发明的式(I)活性化合物还适合于防治攻击农业家畜例如牛,羊,山羊,马,猪,驴,骆驼,水牛,兔,鸡,火鸡,鸭,鹅,蜜蜂,其它家养动物例如狗,猫,笼养鸟,缸养鱼,和所谓的实验动物例如仓鼠,豚鼠,大鼠和小鼠的节肢动物。通过防治这些节肢动物,目的在于降低养殖死亡率并降低节肢动物的影响(在肉,牛奶,羊毛,皮革,蛋,蜂蜜等中),由此通过使用本发明的活性化合物,使更经济和简单的动物饲养成为可能。
在兽医领域,根据本发明的活性化合物以已知方法使用,通过内部给药的方法以例如片剂,胶囊剂,饮剂,浸液,颗粒剂,糊剂,清油,栓剂的形式饲喂给药,通过非肠道给药,例如通过注射(肌内,皮下,静脉,腹膜),包埋给药,通过经鼻施用,经过表皮施用的方法,例如以浸泡或浸沾,喷布,泼浇和点涂,冲洗涂粉的形式施用,并可借助包括活性化合物的成形物品,如轭,耳箍,尾记,肢带,马络头,标记设备给药。
当向牛,家禽,家养动物等使用时,式(I)活性化合物可以其包含按重量计1至80%的活性化合物的制剂形式(例如粉剂,乳剂,悬浮剂)或直接使用或将其稀释100至10,000倍后使用,或其可以化学浴的形式使用。
从下述的实施例中可以看到根据本发明的活性化合物的制备和应用。
制备实施例
实施例(I-1)
将6.1g(0.012mol)的实施例(XVII-1)化合物悬浮于50ml干燥乙醇中,不需冷却滴加入6.4g(0.048mol)的30%浓氢氧化钠溶液,在滴加过程中温度上升到27℃。加热混合物,使其沸腾20分钟然后冷却。过滤混合物,用水冲洗滤液并干燥。
产率:4.8g白色结晶(理论值的84%)
M.p.:101-103℃
实施例(I-2)
将17.6g(0.042mol)的实施例(XIV-1)的2,6-二氟-N-[2-羟乙基-1-苯基-4-(4′-二氟甲氧苯基)]-苯甲酰胺悬浮于150ml甲苯中,滴加入20g(0.168mol)的硫酰氯,并将混合物加热到70℃。将混合物保持在此温度下1.5小时,然后使之冷却,真空蒸发掉甲苯。将剩余物溶解在150ml甲醇中。然后加入22.4g(0.168mol)的30%浓氢氧化钠,并将混合物在70℃下加热20分钟。冷却后,浓缩混合物,用二氯甲烷吸收产物,并用水冲洗混合物三次。干燥并浓缩得到14.9g黄色结晶,将其用硅胶充分纯化(石油醚/乙酸乙酯1∶1)。获得13.0g的白色结晶m.p.112℃。
产率:理论值的82%。
类似于实施例I-1或I-2,并根据一般的制备方法得到下述的式(I)化合物
表1a(n=1,m=0)
实施例(I-7)
在5℃将4ml(0.045mol)的50%浓氢氧化钠溶液滴加到在120ml二甲基甲酰胺中的19.8g(0.043mol)的实施例(XVII-3)化合物中。在室温下2小时后,分批倒入500ml冰水中,并吸滤掉已沉淀的催化剂。
产率:15.1g(理论值的83%),m.p.:98至100℃。
实施例(I-8)
将10.9g(0.026mol)的实施例(I-7)化合物悬浮于50ml甲醇中,然后在室温下滴加35.4ml(0.52mol)的25%浓氨水溶液。在室温下28小时后,抽吸过滤掉沉淀,并用少量甲醇冲洗。产率7.6g(理论值的97.4%),m.p.180至182℃。
实施例(I-9)
将在DMF中的9.6g实施例(XVII-3)化合物与如实施例(I-7)中所述的氢氧化钠溶液反应,然后在5℃下,用稀盐酸中和混合物。加入相应量的氨水溶液(参见实施例I-8)后,搅拌混合物15小时,将混合物导入冰水中并用抽洗过滤。产率7g(理论值的94.5%)。
实施例(I-10)
在40至50℃将二氟氯甲烷通入到1.2g(3.4mmol)实施例(I-8)的化合物和2.7g(50mmol)KOH在20ml异丙醇的溶液中。冷却混合物后,将其倒入100ml冰水中,并用每次50ml的二氯甲烷提取两次,干燥提取物,蒸发掉溶剂。应用石油醚/乙酸乙酯1/1作为洗脱剂,在硅胶上色谱分离后,得到0.8g(理论值的50%)无色结晶,m.p.112℃。
实施例(I-11)
将1.4ml(0.01ml)三乙胺加入到悬浮于20ml乙酸乙酯中的3.5g(0.01mol)实施例(I-8)化合物中,然后用15分钟的时间滴加入1.2g(0.01mol)氯甲酸异丙酯,在此过程中反应混合物的温度升至30℃。在室温下搅拌混合物18小时,并用20ml水冲洗,干燥有机相,浓缩后,用二氯甲烷作洗脱剂,在硅胶上对有机层进行色谱分离。产率2.1g(理论值的48%)m.p.104℃。
类似地或遵从一般的制备方法获得下述式(I)化合物:
表1b(m=0,n=1)
表1b-续
*应用实施例I-8化合物的实施例
实施例I-37
实施例I-38
起始化合物的制备
实施例(IIa-1)
将250g 4-羟基联二苯的1000ml丙酮液和50g粉状的氢氧化钠加入反应容器的底部装有进气管的搅拌设备中,并将反应混合物加热至沸腾。随后通入三氟氯乙烯直到混合物饱和。混合物冷却到室温后,计量加入2000ml水,除去分离的有机相。干燥后,蒸馏产物,沸点范围:170-174℃/20mbar。产率:295g。
实施例(IIa-2)
将250g 4-羟基联二苯,1000ml N-甲基吡咯烷酮和50g氢氧化钠粉末导入装有进气管的搅拌设备中,并把混合物加热至130℃。然后通入四氟乙烯直到没有四氟乙烯被吸收。产物冷却到室温后,在3000ml水中搅拌,抽吸过滤掉固体,用水冲洗并在真空干燥。
获得391g 4-氟乙氧基-联二苯=理论产率的98%;熔点65℃。
实施例(IIa-3)
类似地,250g 4-羟基联二苯与六氟丙烷反应,得到4-六氟丙氧基-联二苯。
产率:180g;沸点:96-98℃/0.3mbar,熔点:60℃。
实施例(IIb-1)
将51.1g(0.3mol)的4-羟基联二苯溶于250ml二噁烷中,并加入38.3ml,45%的浓氢氧化钠溶液。将混合物加热到60℃,在此温度下,随后通入100g(1.15mol)的二氟氯甲烷。冷却后,加入75ml水,抽吸过滤掉不溶沉淀,用叔丁基甲基醚提取水相三次。将合并有机相干燥并浓缩。得到55.9g的粗产物;产物中还含有20.9%的起始物苯酚,用氢氧化钠除去苯酚。
产率:40g(理论值的60%)
熔点:35℃
实施例(IIe-1)
在10℃,用15分钟,将22g(0.2mol)氯甲酸乙酯滴加入34g(0.2mol)的4-羟基联二苯和28ml三乙胺的200ml乙酸乙酯溶液。在室温下持续搅拌30分钟,抽吸过滤掉沉淀,用200ml水冲洗液体相,干燥并真空浓缩。剩余物用50ml二异丙醚吸收,抽吸过滤掉催化剂。产率47.5g(理论值的98.5%),m.p.70℃。
实施例(Ic-1)
将800ml苯,40g铁粉和350g 4-二氟甲氧苯胺导入反应容器中,在30-38℃,用5小时,将1000g三氯乙酸的1600ml苯溶液滴加入反应容器。同时,按份加入210g亚硝酸钠(每15分钟12g)。反应稍微放热,在加入过程中有气体放出。加入结束时,在室温下大约连续搅拌20小时。随后将混合物加热至回流温度(75-76℃),伴随气体放出,继续搅拌直到气体放出结束(大约4小时)。冷却反应物,加入2.4升,5%浓盐酸,并首先蒸馏掉苯直到内部温度达到100℃,接着蒸馏水蒸气。分离有机相(液体),用水冲洗,干燥并蒸馏。
产率:109g,熔点55℃。沸点:135-140℃/26巴。
实施例(VII-1)
将5.3g(0.025mol)的4-乙酰基-4′-羟基联二苯导入35ml甲苯中。在60℃下向此悬浮液中加入6.7g(0.075mol)的45%浓氢氧化钠溶液。随后加入0.42g(0.00125mol)的溴化四丁基鏻,在95°至100℃,用2小时通入20g(0.23mol)的二氟氯甲烷。冷却混合物,用水稀释并过滤(0.4g)。分离掉甲苯相,用甲苯提取水相二次。用水冲洗合并的甲苯相,干燥并浓缩。得到5.9g(理论值的83%)米色结晶,熔点:79-81℃。
实施例(VIIa-1)
在40℃下,将三氟氯乙烯通入到50g 4-乙酰基-4′-羟基联二苯,400ml乙腈,60ml水和10g氢氧化钾的混合物中,直到饱和。然后除去乙腈,且剩余物用100ml水搅拌。抽吸过滤掉固体产物并干燥。随后用20ml热环己烷搅拌粗产物并过滤。
产量:45g。M.p:92-94℃。
实施例(VIIa-2)
类似于实施例(VIIa-1),使96g 4-乙酰基-4′-羟基联二苯和四氟乙烯反应得到107g粗产物,将产物溶于甲基叔丁基醚中,并用300ml,5%浓氢氧化钠溶液提取,浓缩醚相。
产量:58g,M.p.95-97℃。
实施例(VIIa-3)
类似于实施例(VIIa-1),用50g 4-乙酰基-4′-羟基联二苯和六氟丙烷得到50g产物。M.p.86-87℃。
实施例(VIII-1)
将29g(0.08mol)的实施例(VIIa-3)的4-六氟丙氧苯基苯乙酮悬浮于200ml甲醇中,在0℃滴加入13.4g(0.084mol)的溴。连续搅拌12小时,浓缩混合物。得到41.3g棕色结晶。用二氯甲烷作为洗脱液,将其在硅胶上纯化。产率:24.6g(理论值的71%)的黄色结晶m.p.69-71℃。
类似的并根据一般的制备方法获得下述的式(VIII)化合物:
表2(m=0,n=1)
实施例号 | OR | Hal | M.p.[℃] | 产率(占理论值的%) |
VIII-2 | 4-OCHF2 | Br | 83-85 | 62 |
VIII-3 | 4-OCF2CHFCl | Br | 72-74 | 63 |
VIII-4 | 4-OCF2CF2H | Br | 56-61℃ | 85 |
实施例(VIII-5)
将7g(0.0525mol)氯化铝悬浮于50ml 1,2-二氯乙烷中。然后在5至10℃滴加入5.9g(0.0525mol)氯乙酰氯。将13.5g(0.05mol)4-四氟乙氧基联二苯,溶于10ml二氯乙烷中,然后在-10℃进行滴加。再将混合物保持在-10℃一小时,并在室温下连续搅拌12小时。将反应混合物倒入150ml冰水中,加入乙酸乙酯,并分离掉有机相。有机相用碳酸氢盐溶液冲洗,然后用水冲洗两次,干燥并浓缩。粗产物用硅胶纯化(二氯甲烷为洗脱液)。得到14.7g浅米色结晶(理论产率的85%)。熔点74℃。
实施例(X-1)
将24.3g(0.055mol)的实施例(VIII-1)的溴化酮导入145ml乙醇/水中。将22.5g(0.33mol)甲酸钠加入到悬浮液中,然后将混合物加热至沸腾12小时。蒸发掉一部分乙醇,并过滤混合物。用水冲洗和过滤后,干燥产物。得到20.7g(理论值的93%)结晶。m.p.135℃。
类似地并根据常规的制备方法得到下述式(X)化合物:
表3(m=0,n=1)
实施例号 | OR | M.p.[℃] | 产率[占理论值的%] |
X-2 | 4-OCHF2 | 115-118 | 91 |
X-3 | 4-OCF2CHFCl | 160 | 97 |
X-4 | 4-OCF2CF2H | 155-160 | 90 |
实施例(XI-1)
将5g(0.018mol)实施例(X-2)的4-二氟甲氧苯基-ω-羟基苯乙酮溶于50ml的1,2-二甲氧乙烷中,并加入5ml水。随后加入1.85g(0.0225mol)乙酸钠和1.9g(0.0225mol)O-甲基羟基胺盐酸盐,并在室温下搅拌混合物过夜。将反应混合物倒入180ml冰水中并通过抽吸过滤,用水冲洗产物并干燥。由此得到5.4g浅米色结晶,m.p.65-81℃(E/Z混合物:43/57)。
类似地并根据常规的制备方法得到下述式(XI)化合物:
表4(m=0,n=1)
实施例号 | OR | M.p.[℃] | 产率(占理论值的%) |
XI-2 | 4-OCF2CHFCl | *) | 89 |
XI-3 | 4-OCF2CHF2 | *) | 83 |
XI-4 | 4-OCF2CHFCF3 | *) | 82 |
*)由于所得E/Z混合物的熔点范围非常宽,则熔点不是特征值。
实施例(XIII-1)
将9.2g(0.2425mol)的硼酸钠导入250ml无水THF中,然后在20℃,用10分钟滴加入27.6g(0.2425mol)三氟乙酸的25ml THF溶液。将14.9g(0.0485mol)实施例(XI-1)的肟醚,溶于25mlTHF,随后在15℃用15分钟,将其滴加入雾状,无色的反应混合物中。在室温下搅拌混合物2小时,并在沸点连续搅拌2小时。冷却后,在大约10℃,小心地加入150ml水,并在室温下连续搅拌12小时。过滤混合物,浓缩滤液。用2N HCl搅拌后,抽吸过滤掉白色结晶,用二氯甲烷冲洗并干燥。
得到13g白色结晶,m.p.180℃(分解)。
产率:理论值的82%。
实施例(XIII-2)
类似于实施例(XIII-1)获得式(XIII-2)的化合物
m.p.197℃。
产率:理论值的91%。
实施例(XIII-3)
类似于实施例(XIII-1)获得式(XIII-3)的化合物
m.p.250℃。
产率:理论值的53%。
实施例(XIV-1)
将1.52g(0.0086mol)的2,6-二氟苯甲酰氯滴加入(在10至20℃)2.5g(0.0086mol)的实施例(XIII-1)的2-氨基-2-苯基-(4-二氟甲氧苯基)-乙醇和0.9g(0.009mol)的三乙基胺的50ml THF混合物中。随后将混合物搅拌3小时并浓缩,产物用二氯甲烷吸收,混合物用水冲洗三次,干燥并浓缩。
得到3.3g浅米色结晶,m.p.146℃。
产率:理论值的83.5%。
类似地并根据常规的制备方法得到下述的式(XIV)化合物:
表5(m=0,n=1)
实施例号 | OR | M.p.[℃] | 产率[理论值的%] |
XIV-2 | 4-OCF2CHFCl | 194-195 | 54 |
XIV-3 | 4-OCF2CHFCF3 | 142-145 | 73 |
XIV-4 | 4-OCF2CF2H | 184-186 | 81 |
实施例(XVII-1)
将10.6g(0.022mol)的实施例(XIV-2)的羟基乙基酰胺悬浮于100ml干燥甲苯中。不需要冷却,滴加入10.5g(0.088mol)的硫酰氯,形成清澈的黄色溶液。将溶液加热至70℃,并在此温度下保持2小时。冷却到0℃后,过滤混合物,并用少量的甲苯冲洗产物并干燥。
由此得到8.8g(理论值的79%)白色结晶,m.p.190-192℃。
实施例(XVII-2)
类似于实施例XVII-1得到下式的白色结晶
m.p.161-164℃(理论值的83%)。
实施例(XVII-3)
在5℃,用30分钟的时间将130.4g(0.98mol)的氯化铝按份加入到53g(0.213mol)的2-(2.6-二氟苯甲酰氨基)-2-甲氧-1-氯乙烷,48.4g(0.2mol)的4-乙氧羰基氧联二苯和12ml冰醋酸的200ml二氯甲烷溶液的混合物中。在此过程中,反应物的颜色从兰变成红紫色。将反应混合物在5℃搅拌1小时并在10℃搅拌1小时,并小心地倒入冰中,从水中小心地倾析悬浮液并在旋转蒸发器中浓缩,剩余物用50ml乙腈处理,抽吸过滤掉已沉淀的结晶,产率42.8g(理论值的47%),m.p.209℃。
类似地并根据制备的常规方法,获得下述式(XVII)化合物
表6:(m=0,n=1)
应用实施例(I-8)化合物的实施例
首先将0.22ml(0.005mol)的45%NaOH溶液,然后在0℃,将0.5g(0.005mol)乙基溴化物滴加入1.75g实施例(I-8)化合物的10ml二甲基甲酰胺溶液中。在室温下搅拌混合物2小时,并将混合物倒入50ml冰水中,抽吸过滤掉结晶,用乙酸乙酯提取滤液,干燥乙酸乙酯相并在真空浓缩。合并结晶,用20ml二异丙基酯搅拌并用抽吸过滤。产率1.1g(理论值的58%)m.p.148至150℃。
在下述应用实施例中,从EP-A-0 432661中已知的式(A)化合物用作对比物
应用实施例
实施例A
菜蛾试验
溶剂:7重量份二甲基甲酰胺
乳化剂:1重量份烷基芳基聚乙二醇醚
为了生产活性化合物的适合的制备物,用1重量份的活性化合物与预定量的溶剂和预定量的乳化剂混合,用水稀释浓缩物得到所需浓度。
通过在所需浓度的活性化合物的制备物中浸沾,处理甘兰叶(Brassica oleracea),在叶片仍然潮湿时,用小菜蛾幼虫(Plutella maculipennis)侵染。
一定时间后,测定杀伤率%。100%意为所有的幼虫已被杀死;0%意为没有幼虫被杀死。
在本试验中,例如用制备实施例(I-2)的化合物,在典型的0.01%的活性化合物浓度下,三天后,杀伤率达100%,且用制备实施例I-11的化合物在典型的0.1%的活性化合物浓度下,七天后,杀伤率达100%。
实施例B
粘虫试验
溶剂:7重量份二甲基甲酰胺
乳化剂:1重量份烷基芳基聚乙二醇醚
为了生产活性化合物的适合的制备物,用1重量份的活性化合物与预定量的溶剂和预定量的乳化剂混合,用水稀释浓缩物得到所需浓度。
通过在所需浓度的活性化合物的制备物中浸沾,处理甘兰叶(Brassica oleracea),在叶片仍然潮湿时,用草地粘虫(Spodoptera frugiperda)幼虫侵染。
一定时间后,测定杀伤率%。100%意为所有的幼虫已被杀死;0%意为没有幼虫被杀死。
在本试验中,例如用制备实施例(I-11)的化合物,在典型的0.1%的活性化合物浓度下,七天后,杀伤率达100%。
实施例C
红叶螨试验(有机磷抗性/喷雾处理)
溶剂:3重量份二甲基甲酰胺
乳化剂:1重量份烷基芳基聚乙二酵醚
为了生产活性化合物的适合的制备物,用1重量份的活性化合物与预定量的溶剂和预定量的乳化剂混合,用水稀释浓缩物得到所需浓度。
对已被各种发育阶段的棉红蜘蛛(Tetranychus urticae)严重侵染的大豆(phaaeolus vulgaris)植株,用所需浓度的活性化合物制备物喷雾。
一定时间后,测定杀伤率%。100%意为所有的幼虫已被杀死;0%意为没有幼虫被杀死。
在本实验中,例如用制备实施例(I-2)的化合物,在典型的0.000032%活性化合物浓度下,七天后,杀伤率达95%,同时已知的化合物(A)仅得到80%的杀伤率。
实施例D
多食性蜱若虫蜕皮试验
供试动物:花蜱(Amblyomma variegatum),已吸食饱的若虫阶段
溶剂:35重量份的乙烯基乙二醇单甲基醚
乳化剂:35重量份的壬基酚聚乙二醇醚
为了生产适合的制剂,将3重量份的活性化合物与7份上述溶剂-乳化剂混合物混合,并用水稀释所得乳油得到各种情况下所需浓度。
将已吸食饱的10只幼虫,在供试活性化合物的制备物中浸没1分钟。将动物转移到装有滤纸片的培替代表面皿(φ9.5cm)中并盖上盖。幼虫在控制环境的室内放置5-6周后,测定蜕皮率。
100%意为所有的动物进行了正常蜕皮;0%意为没有动物进行正常蜕皮。
在本试验中,例如用制备实施例(I-2)的化合物,在典型的1000ppm的活性化合物浓度下,蜕皮率为0%。
实施例E
丽蝇幼虫试验/发育抑制作用
供试动物:丽蝇幼虫
溶剂:35重量份的乙烯基乙二醇单甲基醚
乳化剂:35重量份的壬基酚聚乙二醇醚
为了生产适合的制剂,将3重量份的活性化合物与7份上述溶剂-乳化剂混合物混合,并用水稀释所得乳油得到各种情况下所需浓度。
大约20只丽蝇幼虫被放入试验管中,管中含有大约1cm3的马肉和0.5ml供试活性化合物制剂。24和48小时后,测定活性化合物的制剂的效果。将试验管转移到底部捕满砂子的烧杯中。再过2天后,移去试验管,数蛹。
活性化合物制备物的活性的评价是通过计算1.5倍发育期后出现的蝇数,和未处理对照的蝇数。100%意为无丽蝇出现;0%意为所有的蝇都正常出现。
在本试验中,例如用制备实施例(I-2)的化合物,在典型的1000ppm的活性化合物浓度下,活性为100%。
实施例F
叶蝉试验
溶剂:7重量份二甲基甲酰胺
乳化剂:1重量份烷基芳基聚乙二醇醚
为了生产活性化合物的适合的制备物,用1重量份的活性化合物与预定量的溶剂和预定量的乳化剂混合,用水稀释浓缩物得到所需浓度。
水稻秧(Oryza sativa)在叶片仍潮湿时,用黑尾叶蝉(Nephotettix cincticeps)侵染。
一定时间后,测定杀伤率%。100%意为所有的黑尾叶蝉已被杀死;0%意为没有黑尾叶蝉被杀死。
在本实验中,例如用制备实施例I-7,I-8和I-11的化合物,在典型的0.1%的活性化合物浓度下,六天后,杀伤率至少90%。
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DE4428536 | 1994-08-12 | ||
DEP4428536.1 | 1994-08-12 | ||
DEP4444108.8 | 1994-12-12 | ||
DE4444108A DE4444108A1 (de) | 1994-08-12 | 1994-12-12 | Substituierte Biphenyloxazoline |
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CN95115337A Expired - Fee Related CN1098844C (zh) | 1994-08-12 | 1995-08-11 | 取代联苯基噁唑啉 |
CN011112611A Expired - Fee Related CN1217903C (zh) | 1994-08-12 | 2001-03-09 | 取代联苯基噁唑啉 |
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US (2) | US6172093B1 (zh) |
EP (1) | EP0696584B1 (zh) |
JP (1) | JPH0859636A (zh) |
CN (2) | CN1098844C (zh) |
AU (1) | AU711555B2 (zh) |
BR (1) | BR9503632A (zh) |
CA (1) | CA2155821A1 (zh) |
CZ (1) | CZ206995A3 (zh) |
DK (1) | DK0696584T3 (zh) |
ES (1) | ES2126817T3 (zh) |
GR (1) | GR3029434T3 (zh) |
HU (1) | HUT73546A (zh) |
NZ (1) | NZ272747A (zh) |
TR (1) | TR199500945A1 (zh) |
TW (1) | TW440429B (zh) |
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Publication number | Priority date | Publication date | Assignee | Title |
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TW440429B (en) * | 1994-08-12 | 2001-06-16 | Bayer Ag | Substituted biphenyloxazolines |
DE4444111A1 (de) * | 1994-12-12 | 1996-06-13 | Bayer Ag | Substituierte m-Biphenyloxazolin-Derivate |
DE19520936A1 (de) * | 1995-06-08 | 1996-12-12 | Bayer Ag | Ektoparasitizide Mittel |
JP2000500755A (ja) * | 1995-11-17 | 2000-01-25 | バイエル・アクチエンゲゼルシヤフト | ビフェニルエーテルオキサゾリン及びその有害生物防除剤としての使用 |
AU2558397A (en) * | 1996-05-01 | 1997-11-19 | E.I. Du Pont De Nemours And Company | Arthropodicidal benzamides |
DE19649307A1 (de) * | 1996-11-28 | 1998-06-04 | Bayer Ag | 4-Cyclohexylphenyl-oxazoline |
US6410581B1 (en) | 1997-03-05 | 2002-06-25 | Bayer Aktiengesellschaft | Disubstituted biphenyloxazolines |
DE19717228A1 (de) * | 1997-04-24 | 1998-10-29 | Bayer Ag | Substituierte Oxazolin-Derivate |
DE19727889A1 (de) * | 1997-07-01 | 1999-01-07 | Bayer Ag | 2-(2-Methylphenyl)-oxazoline |
CO5031296A1 (es) | 1997-11-04 | 2001-04-27 | Novartis Ag | Derivados de azolina, compuestos que la contienen y metodo para la preparacion y aplicacion de dicho compuesto |
BR0009357A (pt) * | 1999-03-26 | 2002-03-05 | Novartis Ag | Preparação e utilização de enanciÈmeros puros das oxazolinas 2,4-dissubstituìdas |
TWI275589B (en) * | 2000-06-22 | 2007-03-11 | Dow Agrosciences Llc | 2-(3,5-disubstituted-4-pyridyl)-4-(thienyl, thiazolyl or arylphenyl)-1,3-oxazoline compounds |
US7534894B2 (en) | 2003-09-25 | 2009-05-19 | Wyeth | Biphenyloxy-acids |
CA2620440C (en) * | 2005-08-29 | 2014-01-28 | Novartis Ag | Use of oxazole derivatives for controlling fish parasites |
CN101836626A (zh) * | 2010-05-17 | 2010-09-22 | 天津师范大学 | 一种含有氟啶胺的农药水悬浮剂及其制备方法 |
CN102643177B (zh) * | 2012-04-13 | 2014-06-18 | 阜新恒通氟化学有限公司 | 一种芳香族氢氟醚的制备方法 |
CN107556260B (zh) * | 2017-10-20 | 2019-07-09 | 南通泰禾化工股份有限公司 | 一种乙螨唑制备方法 |
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GB1400448A (en) | 1971-08-25 | 1975-07-16 | Boots Co Ltd | Oxazoline derivatives arylalkanoic acids their preparation and therapeutic compositions containing them |
US4960884A (en) * | 1989-03-02 | 1990-10-02 | Fmc Corporation | Pesticidal 2-fluoroethyl ethers |
AU634608B2 (en) * | 1989-12-09 | 1993-02-25 | Kyoyu Agri Co., Ltd. | 2-substituted phenyl-2-oxazoline or thiazoline derivatives, process for producing the same and insectides and acaricides containing the same |
AU658955B2 (en) * | 1992-01-28 | 1995-05-04 | Sumitomo Chemical Company, Limited | An oxazoline derivative, its production and its use |
ES2118816T3 (es) * | 1992-04-28 | 1998-10-01 | Yashima Kagaku Kogyo Kk | 2-(2,6-difluorofenil)-4-(2-etoxi-4-terc-butilfenil)-2-oxazolina. |
JP3209576B2 (ja) | 1992-06-12 | 2001-09-17 | 八洲化学工業株式会社 | ダニ防除剤 |
TW259693B (zh) * | 1993-08-04 | 1995-10-11 | Du Pont | |
JP3279818B2 (ja) * | 1994-06-09 | 2002-04-30 | 八洲化学工業株式会社 | 殺虫・殺ダニ剤 |
TW440429B (en) * | 1994-08-12 | 2001-06-16 | Bayer Ag | Substituted biphenyloxazolines |
CZ104797A3 (en) * | 1994-10-06 | 1997-07-16 | Bayer Ag | Substituted biphenyloxazolines, process of their preparation, intermediates for their preparation, preparations in which said substances are comprised and their application |
CN1173172A (zh) | 1995-01-20 | 1998-02-11 | 纳幕尔杜邦公司 | 杀虫和杀螨的噁唑啉和噻唑啉 |
JP2000500755A (ja) * | 1995-11-17 | 2000-01-25 | バイエル・アクチエンゲゼルシヤフト | ビフェニルエーテルオキサゾリン及びその有害生物防除剤としての使用 |
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- 1995-08-02 TR TR95/00945A patent/TR199500945A1/xx unknown
- 1995-08-04 EP EP95112277A patent/EP0696584B1/de not_active Expired - Lifetime
- 1995-08-04 ES ES95112277T patent/ES2126817T3/es not_active Expired - Lifetime
- 1995-08-04 DK DK95112277T patent/DK0696584T3/da active
- 1995-08-04 US US08/511,212 patent/US6172093B1/en not_active Expired - Fee Related
- 1995-08-08 AU AU28445/95A patent/AU711555B2/en not_active Ceased
- 1995-08-09 NZ NZ272747A patent/NZ272747A/en unknown
- 1995-08-09 JP JP7224786A patent/JPH0859636A/ja active Pending
- 1995-08-10 CA CA002155821A patent/CA2155821A1/en not_active Abandoned
- 1995-08-11 CZ CZ952069A patent/CZ206995A3/cs unknown
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- 1995-08-11 BR BR9503632A patent/BR9503632A/pt not_active IP Right Cessation
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NZ272747A (en) | 1997-01-29 |
CZ206995A3 (en) | 1996-02-14 |
CN1122801A (zh) | 1996-05-22 |
TR199500945A1 (tr) | 1996-10-21 |
HUT73546A (en) | 1996-08-28 |
AU711555B2 (en) | 1999-10-14 |
US6172093B1 (en) | 2001-01-09 |
CN1098844C (zh) | 2003-01-15 |
ES2126817T3 (es) | 1999-04-01 |
HU9502378D0 (en) | 1996-05-28 |
GR3029434T3 (en) | 1999-05-28 |
JPH0859636A (ja) | 1996-03-05 |
EP0696584A1 (de) | 1996-02-14 |
EP0696584B1 (de) | 1999-01-20 |
BR9503632A (pt) | 1996-05-28 |
AU2844595A (en) | 1996-02-22 |
US5969147A (en) | 1999-10-19 |
CN1318536A (zh) | 2001-10-24 |
CA2155821A1 (en) | 1996-02-13 |
TW440429B (en) | 2001-06-16 |
DK0696584T3 (da) | 1999-09-13 |
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