CN1177345A - 氨基酸酰胺衍生物及其作为农药的应用 - Google Patents
氨基酸酰胺衍生物及其作为农药的应用 Download PDFInfo
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- CN1177345A CN1177345A CN96192263A CN96192263A CN1177345A CN 1177345 A CN1177345 A CN 1177345A CN 96192263 A CN96192263 A CN 96192263A CN 96192263 A CN96192263 A CN 96192263A CN 1177345 A CN1177345 A CN 1177345A
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- 150000001413 amino acids Chemical class 0.000 title abstract description 12
- 239000000575 pesticide Substances 0.000 title abstract 2
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 96
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 35
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 28
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 22
- 239000001257 hydrogen Substances 0.000 claims abstract description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 22
- 238000000034 method Methods 0.000 claims abstract description 20
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 20
- 239000001301 oxygen Substances 0.000 claims abstract description 20
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000005864 Sulphur Substances 0.000 claims abstract description 19
- 125000003118 aryl group Chemical group 0.000 claims abstract description 19
- 238000002360 preparation method Methods 0.000 claims abstract description 17
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 16
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 13
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000002837 carbocyclic group Chemical group 0.000 claims abstract description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 7
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- 239000011737 fluorine Substances 0.000 claims description 101
- 229910052731 fluorine Inorganic materials 0.000 claims description 101
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 99
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 89
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 57
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 40
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- 125000005843 halogen group Chemical group 0.000 claims description 33
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- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 28
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 28
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 12
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- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 10
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- 125000002541 furyl group Chemical group 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
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- 125000004076 pyridyl group Chemical group 0.000 claims description 10
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- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 8
- ZRNSSRODJSSVEJ-UHFFFAOYSA-N 2-methylpentacosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC(C)C ZRNSSRODJSSVEJ-UHFFFAOYSA-N 0.000 claims description 8
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- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
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- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 8
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- 125000005702 oxyalkylene group Chemical group 0.000 claims description 8
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- WIHIUTUAHOZVLE-UHFFFAOYSA-N 1,3-diethoxypropan-2-ol Chemical compound CCOCC(O)COCC WIHIUTUAHOZVLE-UHFFFAOYSA-N 0.000 claims description 7
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- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical group [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 6
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/40—Acylated substituent nitrogen atom
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/81—Radicals substituted by nitrogen atoms not forming part of a nitro radical
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
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Abstract
本发明涉及新颖的取代氨基酸酰胺,其多种制备方法和其作为农药的应用,其中A代表单键或任选取代的亚烷基,Q1、Q2、Q3相同或不同且各代表氧或硫,R1代表各任选取代的烷基、链烯基、炔基、环烷基、环烯基、芳基烷基、芳基、杂环基烷基或杂环基,R2、R5相同或不同且各代表氢或各任选取代的烷基,R3代表氢、或代表各任选取代的烷基或环烷基,R4代表各任选取代的烷基或环烷基,或R3和R4同与之相连的碳原子一起形成任选取代的碳环,且R6代表各任选取代的环烷基、环烯基、芳基或杂环基。
Description
本发明涉及新颖的取代氨基酸酰胺、其多种制备方法和其作为农药的应用。
已知某些取代的氨基酸酰胺例如化合物N-(叔丁氧羰基)-L-缬氨酸-[N-(1-苯基乙基)-酰胺]或化合物N-(叔丁氧羰基)-L-缬氨酸-(N-[1-(2-氯苯基)乙基]-酰胺}或化合物N-(叔丁氧羰基)-L-缬氨酸-{N-甲基-N-[1-(4-氯苯基)乙基]-酰胺}具有杀真菌性能(参见例如EP 398072)。
然而,这些现有技术中的化合物的活性,特别是在低施用量和浓度下,并不是在所有的施用领域总令人满意
基、芳基、杂环基烷基或杂环基,R2、R5相同或不同且各代表氢或各任选取代的烷基,R3 代表氢,或代表各任选取代的烷基或环烷基,R4 代表各任选取代的烷基或环烷基,或R3和R4同与之相连的碳原子一起形成任选取代的碳环,且R6 代表各任选取代的环烷基、环烯基、芳基或杂环基。
在定义中,饱和或不饱和烃链,如烷基、烷二基、链烯基或炔基,包括与杂原子相连,如在烷氧基、烷硫基或烷基氨基中,各是直链或支链的。
卤素通常代表氟、氯、溴或碘,优选氟、氯或溴,特别是氟或氯。
芳基代表芳族的单或多环烃环,如苯基、萘基、蒽基或菲基,优选苯基或萘基,特别是苯基。
杂环代表饱和或不饱和的环形式的芳族化合物,其中至少一个环原子是杂原子,即不同于碳的原子。如果环含有几个杂原子,则它们可以是相同或不同。杂原子优选是氧、氮或硫。这些环形式的化合物任选与另外的碳环或杂环的稠合的或桥连的环一起形成多环体系。优选的是单或二环体系,特别是单或二环芳环体系。
环烷基代表饱和的环形式的碳环化合物,它任选与另外的碳环的、稠合或桥连的环一起形成多环体系。
环烯基代表含有至少一个双键的环形式的碳环化合物,且任选与另外的碳环的稠合或桥连的环一起形成多环。
还发现,新颖的通式(I)氨基酸酰胺可以通过如下方法获得:使通式(II)的N-取代氨基酸其中Q1、Q2、Q3、R1、R2、R3和R4各具有上述含意,如果需要在反应助剂存在下,如果需要在稀释剂存在下,与通式(III)的胺反应其中A、R5和R6具有上述含意。
最后,业已发现,新颖的通式(I)的氨基酸酰胺具有非常强的杀真菌作用。
本发明化合物任选以各种可能异构体形式的混合物形式存在,特别是立体异构体,如E和Z、苏型和赤型和光学异构体。本文描述且要求保护E和Z异构体、苏型和赤型异构体以及光学异构体和这些异构体的任意混合物。
本发明优选涉及这样的式(I)化合物,其中A 代表单键,或代表具有1至6个碳原子的亚烷基,它任选由相同或
不同的取代基单或多取代,其中可能的取代基优选选自:
卤素、氰基、硝基、氨基、羟基、甲酰基、羧基、氨基甲酰基或硫
代氨基甲酰基;
直链或支链烷氧基、烷硫基、烷基亚磺酰基或烷基磺酰基,它们各
具有1至6个碳原子;
直链或支链链烯基或链烯氧基,它们各具有2至6个碳原子;
直链或支链卤代烷氧基、卤代烷硫基、卤代烷基亚磺酰基或卤代烷
基磺酰基,它们各具有1至6个碳原子和1至13个相同或不同的卤
原子;
直链或支链卤代链烯基或卤代链烯氧基,它们各具有2至6个碳原
子和1至13个相同或不同的卤原子;
直链或支链烷基氨基、二烷基氨基、烷基羰基、烷基羰氧基、烷氧
羰基、烷基磺酰氧基、肟基烷基或烷氧基亚氨基烷基,它们各在其
烷基部分具有1至6个碳原子;
具有3至6个碳原子的环烷基;和
芳基或杂环基,它们各任选由相同或不同的下列取代基单或多取
代:
卤素、氰基和/或具有1至4个碳原子的直链或支链烷基
和/或具有1至4个碳原子和1至9个相同或不同卤原子的直链或支
链卤代烷基
和/或具有1至4个碳原子的直链或支链烷氧基或烷硫基
和/或具有1至4个碳原子和1至9个相同或不同卤原子的直链或支
链卤代烷氧基或卤代烷硫基
和/或两次键连的(twice attached)亚烷基或二氧亚烷基,它们各具
有1至6个碳原子且任选由相同或不同的下列取代基单或多取代:
卤素和/或具有1至4个碳原子的直链或支链烷基和/或具有1至4个
碳原子和1至9个相同或不同卤原子的直链或支链卤代烷基;Q1、Q2、Q3相同或不同且各代表氧或硫,R1 代表具有1至8个碳原子的烷基,它任选由相同或不同的下列取代
基单或多取代:卤素、氰基、羟基、氨基、C1-C4-烷氧基、C1-C4-
烷硫基、C1-C4-烷基亚磺酰基和C1-C4-烷基磺酰基(它们各可由卤
素取代);
或代表各任选卤代的链烯基或炔基,它们各具有至多8个碳原子;
或代表具有3至7个碳原子的环烷基或环烯基,它们各任选由下列
相同或不同的取代基单或多取代:卤素、氰基、羧基、苯基(它任选
由卤素、氰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基或
C1-C4-卤代烷氧基取代)、C1-C4-烷基或C1-C4-烷氧羰基;
或代表具有3至12个环原子的芳基、芳烷基或杂环基,它们各任选
由相同或不同的取代基单或多取代,其中可能的取代基优选选自:
卤素、氰基、硝基、氨基、羟基、甲酰基、羧基、氨基甲酰基或硫
代氨基甲酰基;
直链或支链烷基、烷氧基、烷硫基、烷基亚磺酰基或烷基磺酰基,
它们各具有1至6个碳原子;
直链或支链链烯基或链烯氧基,它们各具有2至6个碳原子;
直链或支链卤代烷基、卤代烷氧基、卤代烷硫基、卤代烷基亚磺酰
基或卤代烷基磺酰基,它们各具有1至6个碳原子和1至13个相同
或不同的卤原子;
直链或支链卤代链烯基或卤代链烯氧基,它们各具有2至6个碳原
子和1至13个相同或不同的卤原子;
直链或支链烷基氨基、二烷基氨基、烷基羰基、烷基羰氧基、烷氧
羰基、烷基磺酰氧基、肟基烷基或烷氧基亚氨基烷基,它们各在其
烷基部分具有1至6个碳原子;
二次键连的亚烷基或二氧亚烷基,它们具有1至6个碳原子,各任
选由相同或不同的下列取代基单或多取代:卤素和/或具有1至4个
碳原子的直链或支链烷基和/或具有1至4个碳原子和1至9个相同
或不同卤原子的直链或支链卤代烷基,
具有3至6个碳原子的环烷基;和
芳基、芳氧基、芳硫基、芳烷基、芳基烷氧基、芳基烷硫基、杂环
基、杂环基氧基、杂环基硫基、杂环基烷基、杂环基烷氧基或杂环
基烷硫基,它们各任选由相同或不同的下列取代基单或多取代:
卤素、氰基和/或具有1至4个碳原子的直链或支链烷基
和/或具有1至4个碳原子和1至9个相同或不同卤原子的直链或支
链卤代烷基
和/或具有1至4个碳原子的直链或支链烷氧基或烷硫基
和/或具有1至4个碳原子和1至9个相同或不同卤原子的直链或支
链卤代烷氧基或卤代烷硫基
和/或二次键连的亚烷基或二氧基亚烷基,它们各具有1至6个碳原
子,任选由相同或不同的下列取代基单或多取代:卤素和/或具有1
至4个碳原子的直链或支链烷基和/或具有1至4个碳原子和1至9
个相同或不同卤原子的直链或支链卤代烷基。R2、R3相同或不同且各代表氢,或代表具有1至4个碳原子的烷基或
具有3至6个碳原子的环烷基,它们各任选由相同或不同的下列取
代基单或多取代:卤素、氰基、羟基、氨基、C1-C4-烷氧基、C1-
C4-烷硫基、C1-C4-烷基亚磺酰基或C1-C4-烷基磺酰基(它们各任选
由卤素取代)R3 代表氢,或代表具有1至8个碳原子的烷基,它各任选由相同或不
同的取代基单或多取代:卤素、氰基、羟基、氨基、C1-C4-烷氧基、
C1-C4-烷硫基、C1-C4-烷基亚磺酰基或C1-C4-烷基磺酰基(它们各
任选由卤素取代);
或代表各任选卤代的链烯基或炔基,它们各具有至多8个碳原子;
或代表具有3至6个碳原子的环烷基,它们各任选由相同或不同的
下列取代基单或多取代:卤素、氰基、羧基、苯基(它任选由卤素、
氰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基或C1-C4-卤代
烷氧基取代)、C1-C4-烷基和C1-C4-烷氧羰基;R4 代表具有1至8个碳原子的烷基,它各任选由相同或不同的下列取
代基单或多取代:卤素、氰基、羟基、氨基、C1-C4-烷氧基、C1-
C4-烷硫基、C1-C4-烷基亚磺酰基或C1-C4-烷基磺酰基(它们各任选
由卤素取代);
或代表各任选卤代的链烯基或炔基,它们各具有至多8个碳原子;
或代表具有3至6个碳原子的环烷基,它们各任选由相同或不同的
下列取代基单或多取代:卤素、氰基、羧基、苯基(它任选由卤素、
氰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基或C1-C4-卤代
烷氧基取代)、C1-C4-烷基和C1-C4-烷氧羰基;或R3和R4同与之相连的碳原子一起形成具有3至8个碳原子的碳环,该
碳环任选由相同或不同的下列取代基单或多取代:卤素、氰基、羟
基、氨基、C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷硫基、C1-C4-
烷基亚磺酰基或C1-C4-烷基磺酰基(它们各任选由卤素取代)且R6 代表具有3至8个碳原子的环烷基或环烯基,它们任选由相同或不
同的下列取代基单或多取代:卤素、氰基、羧基、苯基(它任选由卤
素、氰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基或C1-C4-
卤代烷氧基取代)、C1-C4-烷基和C1-C4-烷氧羰基;
或代表具有3至12个环原子的芳基或杂环基,它们各任选由相同或
不同的取代基单或多取代,可能的取代基优选选自:
卤素、氰基、硝基、氨基、羟基、甲酰基、羧基、氨基甲酰基或硫
代氨基甲酰基;
直链或支链烷基、烷氧基、烷硫基、烷基亚磺酰基或烷基磺酰基,
它们各具有1至6个碳原子;
直链或支链链烯基或链烯氧基,它们各具有2至6个碳原子;
直链或支链卤代烷基、卤代烷氧基、卤代烷硫基、卤代烷基亚磺酰
基或卤代烷基磺酰基,它们各具有1至6个碳原子和1至13个相同
或不同的卤原子;
直链或支链卤代链烯基或卤代链烯氧基,它们各具有2至6个碳原
子和1至13个相同或不同的卤原子;
直链或支链烷基氨基、二烷基氨基、烷基羰基、烷基羰氧基、烷氧
羰基、烷基磺酰氧基、肟基烷基或烷氧基亚氨基烷基,它们各在其
烷基部分具有1至6个碳原子;
二次键连的亚烷基或二氧亚烷基,它们各具有1至6个碳原子且任
选由相同或不同的下列取代基单或多取代:卤素和/或具有1至4个
碳原子的直链或支链烷基和/或具有1至4个碳原子和1至9个相同
或不同卤原子的直链或支链卤代烷基,
具有3至6个碳原子的环烷基;和
芳基、芳氧基、芳硫基、芳烷基、芳基烷氧基、芳基烷硫基、杂环
基、杂环基氧基、杂环基硫基、杂环基烷基、杂环基烷氧基或杂环
基烷硫基,它们各任选由相同或不同的下列取代基单或多取代:
卤素、氰基和/或具有1至4个碳原子的直链或支链烷基;
和/或具有1至4个碳原子和1至9个相同或不同卤原子的直链或支
链卤代烷基;
和/或具有1至4个碳原子的直链或支链烷氧基或烷硫基;
和/或具有1至4个碳原子和1至9个相同或不同卤原子的直链或支
链卤代烷氧基或卤代烷硫基;
和/或二次键连的亚烷基或二氧基亚烷基,它们各具有1至6个碳原
子且任选各由相同或不同的下列取代基单或多取代:卤素和/或具有1
至4个碳原子的直链或支链烷基和/或具有1至4个碳原子和1至9
个相同或不同卤原子的直链或支链卤代烷基。
本发明特别涉及这样的式(I)化合物,其中A 代表单键,或代表亚甲基、1,1-亚乙基、1,2-亚乙基、1,1-、
1,2-、1,3-或2,2-亚丙基、1,1-、1,2-、1,3-、1,4-、2,2-、2,3-亚丁
基或1,1-、1,2-或1,3-(2-甲基亚丙基),它们任选由相同或不同的下
列取代基单或多取代:氟、氯、氰基、甲氧基、苯基、甲苯基、乙
苯基、甲氧基苯基、乙氧基苯基、氯苯基、氟苯基、三氟甲基苯基
或二甲苯基,Q1、Q2、Q3相同或不同且各代表氧或硫,R1 代表甲基、乙基、正或异丙基、正、异、仲或叔丁基、1-、2-、3-、
新戊基、1-、2-、3-、4-(2-甲基丁基)、1-、2-、3-己基、1-、2-、
3-、4-、5-(2-甲基戊基)、1-、2-、3-、(3-甲基戊基)、2-乙基丁基、
1-、3-、4-(2,2-二甲基丁基)、1-、2-(2,3-二甲基丁基),它们任选由
下列取代基单至五取代:氟、氯、溴、氰基、羟基、氨基、甲氧基、
乙氧基、甲硫基、乙硫基、甲基亚磺酰基、乙基亚磺酰基、甲磺酰
基、乙磺酰基(它们各任选由氟和/或氯取代),
或代表烯丙基、丁烯基、1-甲基烯丙基、炔丙基或1-甲基炔丙基,
它们各任选由氟、氯或溴单至三取代;
或代表环丙基、环丁基、环戊基或环己基,它们各任选由下列取代
基单至六取代:氟、氯、溴、甲氧基、乙氧基、氰基、羧基、苯基(它
任选由氟、氯、溴、氰基、甲基、乙基、正或异丙基、正、异、仲
或叔丁基、三氟甲基、甲氧基、乙氧基、正或异丙氧基、二氟甲氧
基或三氟甲氧基取代)、甲基、乙基、正或异丙基、甲氧羰基或乙氧
羰基;
或代表苯基、萘基、苄基、苯乙基、呋喃基、苯并呋喃基、吡咯基、
吲哚基、噻吩基、苯并噻吩基、噁唑基、异噁唑基、噻唑基、异噻
唑基、噁二唑基、噻二唑基、吡啶基、喹啉基、嘧啶基、哒嗪基、
吡嗪基、环氧乙烷基、氧杂环丁烷基、四氢呋喃基、全氢吡喃基、
吡咯烷基、哌啶基或吗啉基,它们各任选单至三取代,可能的取代
基优选选自:
氟、氯、溴、氰基、硝基、氨基、羟基、甲酰基、羧基、氨基甲酰
基、硫代氨基甲酰基、甲基、乙基、正或异丙基、正、异、仲或叔
丁基、甲氧基、乙氧基、正或异丙氧基、甲硫基、乙硫基、正或异
丙硫基、甲基亚磺酰基、乙基亚磺酰基、甲磺酰基或乙磺酰基、三
氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟氯甲氧基、三
氟乙氧基、二氟甲硫基、二氟氯甲硫基、三氟甲硫基、三氟甲基亚
磺酰基或三氟甲磺酰基、甲氨基、乙氨基、正或异丙氨基、二甲氨
基、二乙氨基、乙酰基、丙酰基、乙酰氧基、甲氧羰基、乙氧羰基、
甲基磺酰氧基、乙基磺酰氧基、肟基甲基、肟基乙基、甲氧基亚氨
基甲基、乙氧基亚氨基甲基、甲氧基亚氨基乙基或乙氧基亚氨基乙
基;
三亚甲基(丙-1,3-二基)、亚甲二氧基或亚乙二氧基,它们各被键连两
次且各任选由相同或不同的下列取代基单或多取代:氟、氯、甲基、
三氟甲基、乙基或正或异丙基,
环丙基、环丁基、环戊基或环己基;R2、R5相同或不同且各代表氢、或代表甲基、乙基、正或异丙基、或
正、异、仲或叔丁基,R3 代表氢,或代表甲基、乙基、正或异丙基、正、异、仲或叔丁基,
它们各任选由下列取代基单至五取代:氟、氯、溴、氰基、羟基、
氨基、甲氧基、乙氧基、甲硫基、乙硫基、甲基亚磺酰基、乙基亚
磺酰基、甲磺酰基、乙磺酰基(它们各任选由氟和/或氯取代),
或代表烯丙基、丁烯基、1-甲基烯丙基、炔丙基或1-甲基炔丙基,
它们各任选由氟、氯或溴单至三取代;
或代表环丙基、环丁基、环戊基或环己基,它们各任选由下列取代
基单至六取代:氟、氯、溴、氰基、羧基、甲基、乙基、正或异丙
基、甲氧羰基或乙氧羰基,R4 代表甲基、乙基、正或异丙基、正、异、仲或叔丁基,它们各任选
由下列取代基单至五取代:氟、氯、溴、氰基、羟基、氨基、甲氧
基、乙氧基、甲硫基、乙硫基、甲基亚磺酰基、乙基亚磺酰基、甲
磺酰基、乙磺酰基(它们各任选由氟和/或氯取代),
或代表烯丙基、丁烯基、1-甲基烯丙基、炔丙基或1-甲基炔丙基,
它们各任选由氟、氯或溴单至三取代;
或代表环丙基、环丁基、环戊基或环己基,它们各任选由下列取代
基单至六取代:氟、氯、溴、氰基、羧基、甲基、乙基、正或异丙
基、甲氧羰基或乙氧羰基,或R3和R4同与之相连的碳原子一起形成环丙基、环丁基、环戊基、环己
基,它们任选由下列取代基单至六取代:氟、氯、溴、氰基、羧基、
甲基、乙基、正或异丙基、甲氧羰基或乙氧羰基,且R6 代表环丙基、环丁基、环戊基或环己基,它们各任选由下列取代基
单至六取代:氟、氯、溴、氰基、羧基、甲基、乙基、甲氧基、乙
氧基、正或异丙基、甲氧羰基或乙氧羰基;
或代表苯基、萘基、苄基、苯乙基、呋喃基、苯并呋喃基、吡咯基、
吲哚基、噻吩基、苯并噻吩基、噁唑基、异噁唑基、噻唑基、异噻
唑基、噁二唑基、噻二唑基、吡啶基、喹啉基、嘧啶基、哒嗪基、
吡嗪基、环氧乙烷基、氧杂环丁烷基、四氢呋喃基、全氢吡喃基、
吡咯烷基、哌啶基或吗啉基,它们各任选单至三取代,可能的取代
基优选选自:
氟、氯、溴、氰基、硝基、氨基、羟基、甲酰基、羧基、氨基甲酰
基、硫代氨基甲酰基、甲基、乙基、正或异丙基、正、异、仲或叔
丁基、甲氧基、乙氧基、正或异丙氧基、甲硫基、乙硫基、正或异
丙硫基、甲基亚磺酰基、乙基亚磺酰基、甲磺酰基或乙磺酰基、三
氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟氯甲氧基、三
氟乙氧基、二氟甲硫基、二氟氯甲硫基、三氟甲硫基、三氟甲基亚
磺酰基或三氟甲磺酰基、甲氨基、乙氨基、正或异丙氨基、二甲氨
基、二乙氨基、乙酰基、丙酰基、乙酰氧基、甲氧羰基、乙氧羰基、
甲基磺酰氧基、乙基磺酰氧基、肟基甲基、肟基乙基、甲氧基亚氨
基甲基、乙氧基亚氨基甲基、甲氧基亚氨基乙基或乙氧基亚氨基乙
基;
各键连二次的三亚甲基(丙-1,3-二基)、亚甲二氧基或亚乙二氧基,它
们各任选由相同或不同的下列取代基单或多取代:氟、氯、甲基、
三氟甲基、乙基或正或异丙基;
环丙基、环丁基、环戊基或环己基。
特别优选的是这样的式(I)化合物,其中A 代表单键,或代表亚甲基、1,1-亚乙基、1,2-亚乙基、1,1-、
1,2-、1,3-或2,2-亚丙基、1,1-、1,2-、1,3-、1,4-、2,2-、2,3-亚丁
基或1,1-、1,2-或1,3-(2-甲基亚丙基),它们任选由相同或不同的下
列取代基单或多取代:氟、氯、氰基、甲氧基、苯基、甲苯基、乙
苯基、甲氧基苯基、乙氧基苯基、氯苯基、氟苯基、三氟甲基苯基
或二甲苯基,Q1、Q2、Q3相同或不同且各代表氧或硫,R1 代表甲基、乙基、正或异丙基、正、异、仲或叔丁基,它们任选由
下列取代基单至三取代:氟、氯、溴、甲氧基、乙氧基、甲硫基、
乙硫基(它们各任选由氟和/或氯取代),
或代表烯丙基、丁烯基、1-甲基烯丙基、炔丙基或1-甲基炔丙基,
它们各任选由氟或氯单至三取代;
或代表环丁基、环戊基或环己基,它们各任选由下列取代基单至六
取代:氟、氯、溴、甲氧基、乙氧基、苯基(它任选由氟、氯、溴、
氰基、甲基、乙基、正或异丙基、正、异、仲或叔丁基、三氟甲基、
甲氧基、乙氧基、正或异丙氧基、二氟甲氧基或三氟甲氧基取代)、
甲基、乙基、正或异丙基;
或代表苯基、萘基、苄基、呋喃基、苯并呋喃基、噻吩基、苯并噻
吩基、吡啶基、喹啉基、四氢呋喃基、全氢吡喃基,它们各任选单
至三取代,可能的取代基优选选自:
氟、氯、溴、氰基、硝基、甲基、乙基、正或异丙基、正、异、仲
或叔丁基、甲氧基、乙氧基、正或异丙氧基、甲硫基、乙硫基、正
或异丙硫基、甲基亚磺酰基、乙基亚磺酰基、甲磺酰基或乙磺酰基、
三氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟氯甲氧基、
三氟乙氧基、二氟甲硫基、二氟氯甲硫基、三氟甲硫基、三氟甲基
亚磺酰基或三氟甲磺酰基、乙酰基、丙酰基、乙酰氧基、甲氧羰基、
乙氧羰基、甲基磺酰氧基、乙基磺酰氧基、肟基甲基、肟基乙基、
甲氧基亚氨基甲基、乙氧基亚氨基甲基、甲氧基亚氨基乙基或乙氧
基亚氨基乙基;
三亚甲基(丙-1,3-二基)、亚甲二氧基或亚乙二氧基,它们各键连两次
且各任选由相同或不同的下列取代基单或多取代:氟、氯、甲基、
三氟甲基、乙基或正或异丙基,R2、R5相同或不同且各代表氢、或代表甲基,R3 代表氢,或代表甲基、乙基,正或异丙基、正、异、仲或叔丁基,
它们各任选由下列取代基单至五取代:氟、氯、溴、氰基、羟基、
氨基、甲氧基、乙氧基、甲硫基、乙硫基、甲基亚磺酰基、乙基亚
磺酰基、甲磺酰基、乙磺酰基(它们各任选由氟和/或氯取代),
或代表烯丙基、丁烯基、1-甲基烯丙基、炔丙基或1-甲基炔丙基,
它们各任选由氟、氯或溴单至三取代;
或代表环丙基、环丁基、环戊基或环己基,它们各任选由下列取代
基单至六取代:氟、氯、溴、氰基、羧基、甲基、乙基、正或异丙
基、甲氧羰基或乙氧羰基,R4 代表甲基、乙基、正或异丙基、正、异、仲或叔丁基,它们各任选
由下列取代基单至五取代:氟、氯、溴、氰基、羟基、氨基、甲氧
基、乙氧基、甲硫基、乙硫基、甲基亚磺酰基、乙基亚磺酰基、甲
磺酰基、乙磺酰基(它们各任选由氟和/或氯取代),
或代表烯丙基、丁烯基、1-甲基烯丙基、炔丙基或1-甲基炔丙基,
它们各任选由氟、氯或溴单至三取代;
或代表环丙基、环丁基、环戊基或环己基,它们各任选由下列取代
基单至六取代:氟、氯、溴、氰基、羧基、甲基、乙基、正或异丙
基、甲氧羰基或乙氧羰基,R3和R4同与之相连的碳原子一起形成环丙基、环丁基、环戊基、环己
基,它们任选由下列取代基单至六取代:氟、氯、溴、氰基、羧基、
甲基、乙基、正或异丙基、甲氧羰基或乙氧羰基,且R6 代表环丙基、环丁基、环戊基或环己基,它们各任选由下列取代基
单至六取代:氟、氯、溴、氰基、羧基、甲基、乙基、甲氧基、乙
氧基、正或异丙基、甲氧羰基或乙氧羰基;
或代表苯基、萘基、苄基、苯乙基、呋喃基、苯并呋喃基、吡咯基、
吲哚基、噻吩基、苯并噻吩基、噁唑基、异噁唑基、噻唑基、异噻
唑基、噁二唑基、噻二唑基、吡啶基、喹啉基、嘧啶基、哒嗪基、
吡嗪基、环氧乙烷基、氧杂环丁烷基、四氢呋喃基、全氢吡喃基、
吡咯烷基、哌啶基或吗啉基,它们各任选单至三取代,可能的取代
基优选选自:
氟、氯、溴、氰基、硝基、氨基、羟基、甲酰基、羧基、氨基甲酰
基、硫代氨基甲酰基、甲基、乙基、正或异丙基、正、异、仲或叔
丁基、甲氧基、乙氧基、正或异丙氧基、甲硫基、乙硫基、正或异
丙硫基、甲基亚磺酰基、乙基亚磺酰基、甲磺酰基或乙磺酰基、三
氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟氯甲氧基、三
氟乙氧基、二氟甲硫基、二氟氯甲硫基、三氟甲硫基、三氟甲基亚
磺酰基或三氟甲磺酰基、甲氨基、乙氨基、正或异丙氨基、二甲氨
基、二乙氨基、乙酰基、丙酰基、乙酰氧基、甲氧羰基、乙氧羰基、
甲基磺酰氧基、乙基磺酰氧基、肟基甲基、肟基乙基、甲氧基亚氨
基甲基、乙氧基亚氨基甲基、甲氧基亚氨基乙基或乙氧基亚氨基乙
基;
各键连二次的三亚甲基(丙-1,3-二基)、亚甲二氧基或亚乙二氧基,它
们各任选由相同或不同的下列取代基单或多取代:氟、氯、甲基、
三氟甲基、乙基或正或异丙基;
环丙基、环丁基、环戊基或环己基。
非常特别优选的本发明式(I)化合物是这样的一组化合物,其中A 代表单键或代表亚甲基、1,1-亚乙基、1,2-亚乙基、1,1-亚丙基、
1,2-亚丙基或2,2-亚丙基,Q1、Q2、Q3各代表氧,R1 代表甲基、乙基、正或异丙基、正、并、仲或叔丁基、 环戊基、环
己基或代表任选由甲基、乙基、甲氧基、乙氧基、溴、氯或氟取代
的苯基或苄基,R2、R5各代表氢,R3 代表氢、甲基、乙基或环丙基,R4 代表甲基、乙基或环丙基,或R3和R4同与之相连的碳原子一起形成环戊烷环或环己烷环,且R6 代表环己基,它各任选由甲基、乙基、甲氧基或乙氧基单或二取代;
或代表苯基、萘基、呋喃基、苯并呋喃基、吡咯基、吲哚基、噻吩
基、苯并噻吩基、吡啶基、喹啉基、嘧啶基、哒嗪基、吡嗪基,它
们各任选单至三取代,可能的取代基优选选自:
氟、氯、溴、氰基、硝基、氨基、羟基、甲酰基、羧基、氨基甲酰
基、硫代氨基甲酰基、甲基、乙基、正或异丙基、正、异、仲或叔
丁基、甲氧基、乙氧基、正或异丙氧基、甲硫基、乙硫基、正或异
丙硫基、甲基亚磺酰基、乙基亚磺酰基、甲磺酰基或乙磺酰基、三
氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟氯甲氧基、三
氟乙氧基、二氟甲硫基、二氟氯甲硫基、三氟甲硫基、三氟甲基亚
磺酰基或三氟甲磺酰基、甲氨基、乙氨基、正或异丙氨基、二甲基
氨基、二乙基氨基、乙酰基、丙酰基、乙酰氧基、甲氧羰基、乙氧
羰基、甲基磺酰氧基、乙基磺酰氧基、肟基甲基、肟基乙基、甲氧
基亚氨基甲基、乙氧基亚氨基甲基、甲氧基亚氨基乙基或乙氧基亚
氨基乙基;
三亚甲基(丙-1,3-二基)、亚甲二氧基或亚乙二氧基,它们各被键连两
次且各任选由相同或不同的下列取代基单或多取代:氟、氯、甲基、
三氟甲基、乙基或正或异丙基。
所给的上述一般或优选基团定义适合于式(I)终产物,且相应地适合于在每种制备情况下所需的原料或中间体。
这些基团定义可以按需要相互组合,优选化合物所述范围间的组合也是可能的。
式(II)提供进行本发明方法所需的原料氨基酸的一般定义。在此式(II)中,Q1、Q2、Q3、R1、R2、R3和R4各优选或特别是具有与本发明式(I)化合物描述相关的定义中已经给出的优选或特别优选的Q1、Q2、Q3、R1、R2、R3和R4的含意。
式(II)的原料是已知的和/或可以通过已知的方法制备(参见例如Shin,Chung,Gi等人《化学药物公报》(Chem.Pharm.Bull.)1984,3934-3944)。
式(III)提供进行本发明方法所需的另一种原料胺的一般定义。在此式(III)中,A、R5和R6优选或特别是具有与本发明式(I)化合物描述相关的定义中已经给出的优选或特别优选的A、R5和R6的含意。
式(III)的胺是有机化学已知的试剂。
如果需要,本发明的方法在稀释剂存在下进行。进行本发明方法的适合的稀释剂是所有的惰性有机溶剂。这些溶剂包括特别是脂族、脂环族或芳族烃类,如,石油醚、己烷、庚烷、环己烷、甲基环己烷、苯、甲苯、二甲苯或十氢化萘,卤代烃类,如,氯苯、二氯苯、二氯甲烷、氯仿、四氯化碳、二氯乙烷或三氯乙烷;醚类,如,乙醚、二异丙醚、甲基叔丁基醚、甲基叔戊基醚、二噁烷、四氢呋喃、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷或苯甲醚;酮类,如,丙酮、丁酮、甲基异丁基酮或环己酮;腈类,如,乙腈、丙腈、正或异丁腈或苯甲腈;酰胺类,如N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基甲酰苯胺、N-甲基吡咯烷酮或六甲基磷酰三胺;酯类,如,乙酸甲酯或乙酸乙酯;亚砜类,如二甲亚砜;砜类如环丁砜。
如果需要,本发明是在适合的缩合剂存在下进行的。可能的缩合剂是所有的通常可以用于这种酰胺化反应的缩合剂。形成酰基卤的试剂实例有,例如,光气、三溴化磷、三氯化磷、五氯化磷、磷酰氯或亚硫酰二氯;形成酸酐的试剂是例如,氯甲酸乙酯、氯甲酸甲酯、氯甲酸异丙酯、氯甲酸异丁酯或甲磺酰氯;碳化二亚胺,如N,N’-二环己基碳化二亚胺(DCC)、或其它常规缩合剂,如五氧化磷、多磷酸、N,N’-羰基二咪唑、2-乙氧基-N-乙氧羰基-1,2-二氢喹啉(EEDQ)或三苯基膦/四氯化碳。
如果需要,本发明的方法是在适用的酸受体存在进行的。适合的酸受体是所有的常规无机或有机碱。这些碱包括例如:碱金属或碱土金属氢化物、氢氧化物、氨化物、醇化物、乙酸盐、碳酸盐或碳酸氢盐,如氢化钠、氨化钠、甲醇钠、乙醇钠、叔丁醇钾、氢氧化钠、氢氧化钾、氢氧化铵、乙酸钠、乙酸钾、乙酸钙、乙酸铵、碳酸钠、碳酸钾、碳酸氢钾、碳酸氢钠或碳酸铵,以及叔胺如三甲胺、三乙胺、三丁胺、N,N-二甲基苯胺、N,N-二甲基苄胺、吡啶、N-甲基哌啶、N-甲基吗啉、N,N-二甲基氨基吡啶、二氮杂双环辛烷(DABCO)、二氮杂双环壬烯(DBN)和二氮杂双环十一碳烯(DBU)。
如果需要,本发明方法是在催化剂存在下进行的。实例包括例如4-二甲基氨基吡啶、1-羟基苯并三唑和二甲基甲酰胺。
进行本发明方法时,反应温度可以在相当宽的范围内变化。一般而言,温度是在-78℃和+120℃之间,优选采用-60℃至+25℃间的温度。
实施本发明方法制备式(I)化合物时,每摩尔式(II)氨基酸衍生物,一般采用0.5至5摩尔,优选采用等摩尔的式(III)胺。
反应的进行以及反应产物的收集和分离是通过已知的方法来完成的(参见例如制备实施例)。
本发明的方法也可以分二个阶段进行。在这种情况下,首先将通式(II)的氨基酸衍生物转化成活化的形式,并在随后的步骤中,与通式(III)的胺反应,给出本发明通式(I)的氨基酸酰胺。
式(II)氨基酸衍生物的适合活化形式是所有的羧基活化衍生物,如酰基卤,优选酰基氯,酰基叠氮以及对称或混合的酸酐,如混合的O-烷基羧酸酐,和活化的酯,如对硝基苯基酯或N-羟基琥珀酰亚胺酯,以及与缩合剂如二环己基碳化二亚胺的加合物,或原位产生的氨基酸活化形式。
实施两步法,优选的是使用相应于式(II)氨基酸的酰基氯和混合酸酐。它们可以通过以常规的方式使式(11)的氨基酸或其盐与卤化剂或制备混合酸酐的已知试剂反应来制备,如例如五氯化磷、亚硫酰二氯、草酰氯或氯甲酸酯。
如果需要,两步法中的每一步是在稀释剂存在下,如果需要是在催化剂存在下进行的。优选的稀释剂和催化剂是那些已经提到的与一步法的描述相关的稀释剂和催化剂。
反应的进行以及反应产物的收集和分离是通过已知的方法来完成的。
本发明的活性化合物具有强的杀微生物活性,且可以实际上用来防治有害微生物。本发明活性化合物适合用作作物保护剂,特别是杀真菌剂。
杀真菌剂用在作物保护中,用于防治根肿菌纲,卵菌纲,壶菌纲,接合菌纲,子囊菌纲,担子菌纲和半知菌类。
上面列出的某些病原真菌病害以属名给出, 可以提到的有例如下列,但决不限于此:腐霉属,如终极腐霉(Pythium ultimum);疫霉属,如蔓延疫霉(Phytophthora infestans);假霜霉属,如葎草假霜霉(Pseudoperonospora humuli)或古巴假霜霉(P.cubensis);单轴霉属,如葡萄生单轴霉(Plasmopara viticola);霜霉属,如豌豆霜霉(Peronospora pisi)或芸苔霜霉(P.brassicae);白粉菌属,如禾白粉菌(Erysiphe graminis);单丝壳属,如苍耳单丝壳菌(Sphaerotheca fuliginea);柄球菌属,如苹果白粉病柄球菌(Podosphaera leucotricha);黑星菌属,如苹果黑星菌(Venturia inaequalis);核腔菌属, 如圆核腔菌(Pyrenophora teres)或麦类核腔菌(Pgrammea)(分生孢子形式:Drechslera,异名:长蠕孢属(Helminthosporium));旋孢腔菌属,如禾旋孢腔菌(Cochliobolus sativus)(分生孢子形式:Drechslera,异名:长蠕孢属(Helminthosporium));单孢锈属,如菜豆单孢锈菌(Uromyces appendiculatus);柄锈属,如隐匿柄锈菌(Puccinia recondita);腥黑粉菌属,如小麦网腥黑粉菌(Tilletia caries);黑粉菌属,如裸黑粉菌(Ustilago nuda)或燕麦散黑粉菌(U.avenae);薄膜革菌属,如佐佐木氏薄膜革菌(Pellicularia sasakii);梨孢菌属,如稻梨孢菌(Pvricularia oryzae);镰孢属,如大刀镰孢(Fusarium culmorum);葡萄孢属,如灰色葡萄孢(Botrytis cinerea);壳针孢属,如颖枯壳针孢(Septoria nodorum);小球腔菌属,如颍枯病小球腔菌(Leptosphaeria nodorum);尾孢属,如变灰尾孢菌(Cercospora canescens);链格孢属,如甘蓝黑斑病链格孢菌(Alternaria brassicae),和假小尾孢菌属,如麦类眼斑病菌(Pseudocercosporalla herpotrichoides)。
在防治植物病害所需浓度下,植物对活性化合物的良好耐药性,使活性化合物可以处理植物的地上部分、繁殖根茎和种子以及土壤。
本发明的活性化合物可以特别成功地用于防治葡萄、果树栽培和园艺中的病害,如防治单轴霉和疫霉菌属种类引起的病害。
根据其具体的物理和/或化学特性,活性化合物可以转化成常规剂型,如溶液、乳剂、悬浮剂、粉剂、泡沫剂、膏剂、颗粒剂、气雾剂、聚合物中的细微胶囊和转化成种子包衣组合物、以及ULV冷和热雾剂。
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、压力下的液化气体)混合,和/或与固体载体混合,并任选使用表面活性剂(即乳化剂和/或分散剂和/或起泡剂)。用水作填充剂的情况下,也可以用有机溶剂作助溶剂。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,例如石油馏份,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亚砜,以及水;液化气填充剂或载体是指环境温度和大气压力下是气体的液体,例如气雾抛射剂,例如卤代烃类,或丁烷、丙烷、氮气和二氧化碳; 固体载体适合的有: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:例如压碎和破碎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;乳化剂和/或起泡剂适合的有: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质水解产物;分散剂适合的有: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。其它的粘合剂可以是矿物油和植物油。
也可能使用染料,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%。
当用于植物保护时,本发明的活性化合物可以其本身或以其制剂形式,与已知的杀真菌剂、杀细菌剂、杀螨剂、杀线虫剂或杀虫剂的混合物的形式使用,以扩大作用谱,或为防止抗性的逐步建立。
在许多情况下,可以获得增效作用。
适合用于混合物的组分是例如下列化合物:杀真菌剂:
2-氨基丁烷、2-苯胺基-4-甲基-6环丙基-嘧啶;2′,6′-二溴-2-甲基-4′-三氟甲氧基-4′-三氟甲基-1,3-噻唑-5-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、一甲呋萎灵、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 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、碱式氯化铜、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、perfurazoat、戊菌唑、戊菌隆、稻病磷、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、齐墩螨素(avermectin)、AZ 60541、azadirachtin、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、CGA 157 419、CGA 184699、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、氧氰菊酯、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、二噁硫磷、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、fipronil、氟啶胺、fluazuron、氟螨脲、氟氰戊菊酯、氰虫脲、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、pyrachlophos、吡唑硫磷、苯哒嗪硫磷、反灭菊酯、除虫菊、哒螨酮、pyrimidifen、蚊蝇醚、喹硫磷、RH 5992、水杨硫磷、硫线磷、silafluofen、治螟磷、甲丙硫磷、tebufenozide、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、zetamethrin。
本发明活性化合物也可与其它已知活性化合物如除草剂、或与化肥和生长调节剂混合。
活性化合物可以以其原样或以其制剂或由其制备的使用形式使用,所述的制备使用形式有例如可直接使用溶液、悬浮剂、可湿性粉剂、膏剂、可溶性粉剂、粉剂和颗粒剂。它们以常规方法使用,例如浇泼、喷雾、弥雾、撒施、喷粉、起泡、涂刷等等。此外可用超低容量方法使用化合物,或将活性化合物制剂或活性化合物本身注入土壤。也可处理植物的种子。
处理植物部分时,使用形式中的活性化合物浓度可在大范围内变化:通常,在按重量计1和0.0001%之间,优选在按重量计0.5和0.001%间使用。
处理种子时,通常每公斤种子需要0.001至50g,优选0.01至10g量的活性化合物。
处理土壤时,在作用点需要活性化合物的浓度为按重量计0.00001至0.1%,优选按重量计0.0001至0.02%。
在-20℃,将0.5g(0.005mol)N-甲基哌啶加入、之后在-20℃搅拌下将0.7g(0.005mol)氯甲酸异丁酯滴加入含1.0g(0.005mol)2-(异丙氧羰基氨基)-丁-2-烯酸的10ml二氯甲烷中。添加完毕后,在-20℃下继续搅拌10分钟,加入0.75g(0.005mol)的1-(4-甲氧基苯基)-乙胺,将温度保持在低于-15℃。之后在-15℃再搅拌2小时,并在室温下搅拌15小时,滤出沉淀出的固体物,并用二氯甲烷洗涤,滤液在减压下浓缩,残留物用水消化,并重复用乙酸乙酯萃取,合并的有机相用碳酸氢钠水溶液和水洗涤,并经硫酸钠干燥,在减压下去除溶剂,获得0.8g(理论值的47%)的N-[1-(4-甲氧基苯基)-乙基]-2-(异丙氧羰基氨基)-丁-2-烯酸酰胺,为无色油状物。1H-NMR(CDCl3,TMS):δ(ppm):1.25(m,6H)、1.50(d,3H)、1.74(d,3H)、3.79(s,3H)。表1:表1(续)表1(续)表1(续)表1(续)表1(续)表1(续)表1(续)表1(续)表1(续)表1(续)表1(续)*) 1H-NMR谱是采用四甲基硅烷作内标在氘氯仿(CDCl3)或六氘二甲基亚砜(DMSO-d)中记录的。所述的值是化学位移值,为以ppm计的d值。用途实施例实施例A葡萄生单轴霉病保护性防治试验溶剂:4.7份重量的丙酮乳化剂:0.3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。
测试保护性活性时,将幼株用活性化合物制剂喷雾。喷液层变干后,将植株用葡萄生单轴霉病菌(Plasmopara viticola)的孢子水悬浮液接种。之后,将植株放在20-22℃和100%相对湿度的培养箱中1天。接着将植物放置于21℃和约90%相对湿度的温室中。再将植物在培养箱中湿润和放置1天。
接种6天后进行评价。
在此试验中,在活性化合物浓度为100ppm的情况下,显示大于90%效力的有例如化合物(2)、(8)、(10)、(11)、(12)、(15)、(19)、(20)、(23)、(36)、(39)和(41)。实施例B马铃薯蔓延疫霉病保护性防治试验溶剂:12.5份重量的丙酮乳化剂:0.3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。
测试保护性活性时,将幼株用活性化合物制剂喷雾至喷雾液向下滴流。喷液层变干后,将植株用蔓延疫霉(Phytophthora infestans)的孢子水悬浮液接种。
之后,将植物放置于约20℃和100%相对湿度的培养箱中。
接种4天后进行评价。
在此试验中,在活性化合物浓度为0.05%的情况下,显示100%效力的有例如制备实施例的化合物(2)。
Claims (9)
2.根据权利要求1的式(1)化合物,其中A 代表单键,或代表具有1至6个碳原子的亚烷基,它任选由相同或
不同的取代基单或多取代,可能的取代基优选选自下列:
卤素、氰基、硝基、氨基、羟基、甲酰基、羧基、氨基甲酰基或硫
代氨基甲酰基;
直链或支链烷氧基、烷硫基、烷基亚磺酰基或烷基磺酰基,它们各
具有1至6个碳原子;
直链或支链链烯基或链烯氧基,它们各具有2至6个碳原子;
直链或支链卤代烷氧基、卤代烷硫基、卤代烷基亚磺酰基或卤代烷
基磺酰基,它们各具有1至6个碳原子和1至13个相同或不同的卤
原子;
直链或支链卤代链烯基或卤代链烯氧基,它们各具有2至6个碳原
子和1至13个相同或不同的卤原子:
直链或支链烷基氨基、二烷基氨基、烷基羰基、烷基羰氧基、烷氧
羰基、烷基磺酰氧基、肟基烷基或烷氧基亚氨基烷基,它们各在其
烷基部分具有1至6个碳原子;
具有3至6个碳原子的环烷基;和
芳基或杂环基,它们各任选由相同或不同的下列取代基单或多取
代:
卤素、氰基和/或具有1至4个碳原子的直链或支链烷基
和/或具有1至4个碳原子和1至9个相同或不同卤原子的直链或支
链卤代烷基
和/或具有1至4个碳原子的直链或支链烷氧基或烷硫基
和/或具有1至4个碳原子和1至9个相同或不同卤原子的直链或支
链卤代烷氧基或卤代烷硫基
和/或键连二次的亚烷基或二氧亚烷基,它们各具有1至6个碳原子
且任选由相同或不同的下列取代基单或多取代:卤素和/或具有1至
4个碳原子的直链或支链烷基和/或具有1至4个碳原子和1至9个
相同或不同卤原子的直链或支链卤代烷基;Q1、Q2、Q3相同或不同且各代表氧或硫,R1 代表具有1至8个碳原子的烷基,它任选由相同或不同的下列取代
基单或多取代:卤素、氰基、羟基、氨基、C1-C4-烷氧基、C1-C4-
烷硫基、C1-C4-烷基亚磺酰基和C1-C4-烷基磺酰基(它们各可由卤
素取代);
或代表各任选卤代的链烯基或炔基,它们各具有至多8个碳原子;
或代表具有3至7个碳原子的环烷基或环烯基,它们各任选由下列
相同或不同的取代基单或多取代:卤素、氰基、羧基、苯基(它任选
由卤素、氰基、C1-C4烷基、C1-C4-卤代烷基、C1-C4-烷氧基或
C1-C4-卤代烷氧基取代)、C1-C4-烷基和C1-C4-烷氧羰基;
或代表具有3至12个环原子的芳基、芳烷基或杂环基,它们各任选
由相同或不同的取代基单或多取代,可能的取代基优选选自:
卤素、氰基、硝基、氨基、羟基、甲酰基、羧基、氨基甲酰基或硫
代氨基甲酰基;
直链或支链烷基、烷氧基、烷硫基、烷基亚磺酰基或烷基磺酰基,
它们各具有1至6个碳原子;
直链或支链链烯基或链烯氧基,它们各具有2至6个碳原子;
直链或支链卤代烷基、卤代烷氧基、卤代烷硫基、卤代烷基亚磺酰
基或卤代烷基磺酰基,它们各具有1至6个碳原子和1至13个相同
或不同的卤原子;
直链或支链卤代链烯基或卤代链烯氧基,它们各具有2至6个碳原
子和1至13个相同或不同的卤原子;
直链或支链烷基氨基、二烷基氨基、烷基羰基、烷基羰氧基、烷氧
羰基、烷基磺酰氧基、肟基烷基或烷氧基亚氨基烷基,它们各在其
烷基部分具有1至6个碳原子;
键连二次的亚烷基或二氧亚烷基,它们具有1至6个碳原子,且各
任选由相同或不同的下列取代基单或多取代:卤素和/或具有1至4
个碳原子的直链或支链烷基和/或具有1至4个碳原子和1至9个相
同或不同卤原子的直链或支链卤代烷基,
具有3至6个碳原子的环烷基;
和芳基、芳氧基、芳硫基、芳烷基、芳基烷氧基、芳基烷硫基、杂
环基、杂环基氧基、杂环基硫基、杂环基烷基、杂环基烷氧基或杂
环基烷硫基,它们各任选由相同或不同的下列取代基单或多取代:
卤素、氰基和/或具有1至4个碳原子的直链或支链烷基
和/或具有1至4个碳原子和1至9个相同或不同卤原子的直链或支
链卤代烷基
和/或具有1至4个碳原子的直链或支链烷氧基或烷硫基
和/或具有1至4个碳原子和1至9个相同或不同卤原子的直链或支
链卤代烷氧基或卤代烷硫基
和/或键连二次的亚烷基或二氧亚烷基,它们各具有1至6个碳原
子,且任选由相同或不同的下列取代基单或多取代:卤素和/或具有
1至4个碳原子的直链或支链烷基和/或具有1至4个碳原子和1至
9个相同或不同卤原子的直链或支链卤代烷基,R2、R5相同或不同且各代表氢,或代表具有1至4个碳原子的烷基或
具有3至6个碳原子的环烷基,它们各任选由相同或不同的下列取
代基单或多取代:卤素、氰基、羟基、氨基、C1-C4-烷氧基、C1-
C4-烷硫基、C1-C4-烷基亚磺酰基或C1-C4-烷基磺酰基(它们各任选
由卤素取代)R3 代表氢,或代表具有1至8个碳原子的烷基,它各任选由相同或不
同的取代基单或多取代:卤素、氰基、羟基、氨基、C1-C4-烷氧基、
C1-C4-烷硫基、C1-C4-烷基亚磺酰基或C1-C4-烷基磺酰基(它们各
任选由卤素取代);
或代表各任选卤代的链烯基或炔基,它们各具有至多8个碳原子;
或代表具有3至6个碳原子的环烷基,它们各任选由相同或不同的
下列取代基单或多取代:卤素、氰基、羧基、苯基(它任选由卤素、
氰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基或C1-C4-卤
代烷氧基取代)、C1-C4-烷基和C1-C4-烷氧羰基;R4 代表具有1至8个碳原子的烷基,它各任选由相同或不同的下列取
代基单或多取代:卤素、氰基、羟基、氨基、C1-C4-烷氧基、C1-
C4-烷硫基、C1-C4-烷基亚磺酰基或C1-C4-烷基磺酰基(它们各任选
由卤素取代);
或代表各任选卤代的链烯基或炔基,它们各具有至多8个碳原子;
或代表具有3至6个碳原子的环烷基,它们各任选由相同或不同的
下列取代基单或多取代:卤素、氰基、羧基、苯基(它任选由卤素、
氰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基或C1-C4-卤
代烷氧基取代)、C1-C4-烷基或C1-C4-烷氧羰基;或R3和R4同与之相连的碳原子一起形成具有3至8个碳原子的碳环,该
碳环任选由相同或不同的下列取代基单或多取代:卤素、氰基、羟
基、氨基、C1-C4烷基、C1-C4-烷氧基、C1-C4-烷硫基、C1-C4-
烷基亚磺酰基或C1-C4-烷基磺酰基(它们各任选由卤素取代),且R6 代表具有3至8个碳原子的环烷基或环烯基,它们任选由相同或不
同的下列取代基单或多取代:卤素、氰基、羧基、苯基(它任选由卤
素、氰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基或C1-C4-
卤代烷氧基取代)、C1-C4-烷基和C1-C4-烷氧羰基;
或代表具有3至12个环原子的芳基或杂环基,它们各任选由相同或
不同的取代基单或多取代,可能的取代基优选选自:
卤素、氰基、硝基、氨基、羟基、甲酰基、羧基、氨基甲酰基或硫
代氨基甲酰基;
直链或支链烷基、烷氧基、烷硫基、烷基亚磺酰基或烷基磺酰基,
它们各具有1至6个碳原子;
直链或支链链烯基或链烯氧基,它们各具有2至6个碳原子;
直链或支链卤代烷基、卤代烷氧基、卤代烷硫基、卤代烷基亚磺酰
基或卤代烷基磺酰基,它们各具有1至6个碳原子和1至13个相同
或不同的卤原子;
直链或支链卤代链烯基或卤代链烯氧基,它们各具有2至6个碳原
子和1至13个相同或不同的卤原子;
直链或支链烷基氨基、二烷基氨基、烷基羰基、烷基羰氧基、烷氧
羰基、烷基磺酰氧基、肟基烷基或烷氧基亚氨基烷基,它们各在其
烷基部分具有1至6个碳原子;
键连二次的亚烷基或二氧亚烷基,它们各具有1至6个碳原子且任
选由相同或不同的下列取代基单或多取代:卤素和/或具有1至4个
碳原子的直链或支链烷基和/或具有1至4个碳原子和1至9个相同
或不同卤原子的直链或支链卤代烷基,
具有3至6个碳原子的环烷基;和
芳基、芳氧基、芳硫基、芳烷基、芳基烷氧基、芳基烷硫基、杂环
基、杂环基氧基、杂环基硫基、杂环基烷基、杂环基烷氧基或杂环
基烷硫基,它们各任选由相同或不同的下列取代基单或多取代:
卤素、氰基和具有1至4个碳原子的直链或支链烷基
和/或具有1至4个碳原子和1至9个相同或不同卤原子的直链或支
链卤代烷基
和/或具有1至4个碳原子的直链或支链烷氧基或烷硫基
和/或具有1至4个碳原子和1至9个相同或不同卤原子的直链或支
链卤代烷氧基或卤代烷硫基
和/或键连二次的亚烷基或二氧亚烷基,它们各具有1至6个碳原子
且任选各被相同或不同的下列取代基单或多取代:卤素和/或具有1
至4个碳原子的直链或支链烷基和/或具有1至4个碳原子和1至9
个相同或不同卤原子的直链或支链卤代烷基。
3 根据权利要求1的式(I)化合物,其中A 代表单键,或代表亚甲基、1,1-亚乙基、1,2-亚乙基、1,1-、
1,2-、1,3-或2,2-亚丙基、1,1-、1,2-、1,3-、1,4-、2,2-、2,3-亚丁
基或1,1-、1,2-或1,3-(2-甲基亚丙基),它们任选由相同或不同的下
列取代基单或多取代:氟、氯、氰基、甲氧基、苯基、甲苯基、乙
苯基、甲氧基苯基、乙氧基苯基、氯苯基、氟苯基、三氟甲基苯基
或二甲苯基,Q1、Q2、Q3相同或不同且各代表氧或硫,R1 代表甲基、乙基、正或异丙基、正、异、仲或叔丁基、1-、2-、3-、
新戊基、1-、2-、3-、4-(2-甲基丁基)、1-、2-、3-己基、1-、
2-、3-、4-、5-(2-甲基戊基)、1-、2-、3-、(3-甲基戊基)、2-乙基
丁基、1-、3-、4-(2,2-二甲基丁基)、1-、2-(2,3-二甲基丁基),它
们任选由下列取代基单至五取代:氟、氯、溴、氰基、羟基、氨基、
甲氧基、乙氧基、甲硫基、乙硫基、甲基亚磺酰基、乙基亚磺酰基、
甲磺酰基、乙磺酰基(它们各任选由氟和/或氯取代),
或代表烯丙基、丁烯基、1-甲基烯丙基、炔丙基或1-甲基炔丙基,
它们各任选由氟、氯或溴单至三取代;
或代表环丙基、环丁基、环戊基或环己基,它们各任选由下列取代
基单至六取代:氟、氯、溴、甲氧基、乙氧基、氰基、羧基、苯基(它
任选由氟、氯、溴、氰基、甲基、乙基、正或异丙基、正、异、仲
或叔丁基、三氟甲基、甲氧基、乙氧基、正或异丙氧基、二氟甲氧
基或三氟甲氧基取代)、甲基、乙基、正或异丙基、甲氧羰基或乙氧
羰基;
或代表苯基、萘基、苄基、苯乙基、呋喃基、苯并呋喃基、吡咯基、
吲哚基、噻吩基、苯并噻吩基、噁唑基、异噁唑基、噻唑基、异噻
唑基、噁二唑基、噻二唑基、吡啶基、喹啉基、嘧啶基、哒嗪基、
吡嗪基、环氧乙烷基、氧杂环丁烷基、四氢呋喃基、全氢吡喃基、
吡咯烷基、哌啶基或吗啉基,它们各任选单至三取代,可能的取代
基优选选自:
氟、氯、溴、氰基、硝基、氨基、羟基、甲酰基、羧基、氨基甲酰
基、硫代氨基甲酰基、甲基、乙基、正或异丙基、正、异、仲或叔
丁基、甲氧基、乙氧基、正或异丙氧基、甲硫基、乙硫基、正或异
丙硫基、甲基亚磺酰基、乙基亚磺酰基、甲磺酰基或乙磺酰基、三
氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟氯甲氧基、三
氟乙氧基、二氟甲硫基、二氟氯甲硫基、三氟甲硫基、三氟甲基亚
磺酰基或三氟甲磺酰基、甲氨基、乙氨基、正或异丙氨基、二甲氨
基、二乙氨基、乙酰基、丙酰基、乙酰氧基、甲氧羰基、乙氧羰基、
甲基磺酰氧基、乙基磺酰氧基、肟基甲基、肟基乙基、甲氧基亚氨
基甲基、乙氧基亚氨基甲基、甲氧基亚氨基乙基或乙氧基亚氨基乙
基;
三亚甲基(丙-1,3-二基)、亚甲二氧基或亚乙二氧基,它们各被键连
两次且各任选由相同或不同的下列取代基单或多取代:氟、氯、甲
基、三氟甲基、乙基或正或异丙基,
环丙基、环丁基、环戊基或环己基;R2、R3相同或不同且各代表氢、或代表甲基、乙基、正或异丙基、或
正、异、仲或叔丁基,R3 代表氢,或代表甲基、乙基、正或异丙基、正、异、仲或叔丁基,
它们各任选由下列取代基单至五取代:氟、氯、溴、氰基、羟基、
氨基、甲氧基、乙氧基、甲硫基、乙硫基、甲基亚磺酰基、乙基亚
磺酰基、甲磺酰基、乙磺酰基(它们各任选由氟和/或氯取代),
或代表烯丙基、丁烯基、1-甲基烯丙基、炔丙基或1-甲基炔丙基,
它们各任选由氟、氯或溴单至三取代;
或代表环丙基、环丁基、环戊基或环己基,它们各任选由下列取代
基单至六取代:氟、氯、溴、氰基、羧基、甲基、乙基、正或异丙
基、甲氧羰基或乙氧羰基,R4 代表甲基、乙基、正或异丙基、正、异、仲或叔丁基,它们各任选
由下列取代基单至五取代:氟、氯、溴、氰基、羟基、氨基、甲氧
基、乙氧基、甲硫基、乙硫基、甲基亚磺酰基、乙基亚磺酰基、甲
磺酰基、乙磺酰基(它们各任选由氟和/或氯取代),
或代表烯丙基、丁烯基、1-甲基烯丙基、炔丙基或1-甲基炔丙基,
它们各任选由氟、氯或溴单至三取代;
或代表环丙基、环丁基、环戊基或环己基,它们各任选由下列取代
基单至六取代:氟、氯、溴、氰基、羧基、甲基、乙基、正或异丙
基、甲氧羰基或乙氧羰基,或R3和R4同与之相连的碳原子一起形成环丙基、环丁基、环戊基、环己
基,它们任选由下列取代基单至六取代:氟、氯、溴、氰基、羧基、
甲基、乙基、正或异丙基、甲氧羰基或乙氧羰基,且R6 代表环丙基、环丁基、环戊基或环己基,它们各任选由下列取代基
单至六取代:氟、氯、溴、氰基、羧基、甲基、乙基、甲氧基、乙
氧基、正或异丙基、甲氧羰基或乙氧羰基;
或代表苯基、萘基、苄基、苯乙基、呋喃基、苯并呋喃基、吡咯基、
引哚基、噻吩基、苯并噻吩基、噁唑基、异噁唑基、噻唑基、异噻
唑基、噁二唑基、噻二唑基、吡啶基、喹啉基、嘧啶基、哒嗪基、
吡嗪基、环氧乙烷基、氧杂环丁烷基、四氢呋喃基、全氢吡喃基、
吡咯烷基、哌啶基或吗啉基,它们各任选单至三取代,可能的取代
基优选选自:
氟、氯、溴、氰基、硝基、氨基、羟基、甲酰基、羧基、氨基甲酰
基、硫代氨基甲酰基、甲基、乙基、正或异丙基、正、异、仲或叔
丁基、甲氧基、乙氧基、正或异丙氧基、甲硫基、乙硫基、正或异
丙硫基、甲基亚磺酰基、乙基亚磺酰基、甲磺酰基或乙磺酰基、三
氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟氯甲氧基、三
氟乙氧基、二氟甲硫基、二氟氯甲硫基、三氟甲硫基、三氟甲基亚
磺酰基或三氟甲磺酰基、甲氨基、乙氨基、正或异丙氨基、二甲氨
基、二乙氨基、乙酰基、丙酰基、乙酰氧基、甲氧羰基、乙氧羰基、
甲基磺酰氧基、乙基磺酰氧基、肟基甲基、肟基乙基、甲氧基亚氨
基甲基、乙氧基亚氨基甲基、甲氧基亚氨基乙基或乙氧基亚氨基乙
基;
各键连两次的三亚甲基(丙-1,3-二基)、亚甲二氧基或亚乙二氧基,
它们各任选由相同或不同的下列取代基单或多取代:氟、氯、甲基、
三氟甲基、乙基或正或异丙基;
环丙基、环丁基、环戊基或环己基。
4.根据权利要求1的式(1)化合物,其中A 代表单键,或代表亚甲基、1,1-亚乙基、1,2-亚乙基、1,1-、
1,2-、1,3-或2,2-亚丙基、1,1-、1,2-、1,3-、1,4-、2,2-、2,3-亚丁
基或1,1-、1,2-或1,3-(2-甲基亚丙基),它们任选由相同或不同的下
列取代基单或多取代:氟、氯、氰基、甲氧基、苯基、甲苯基、乙
苯基、甲氧基苯基、乙氧基苯基、氯苯基、氟苯基、三氟甲基苯基
或二甲苯基,Q1、Q2、Q3相同或不同且各代表氧或硫,R1 代表甲基、乙基、正或异丙基、正、异、仲或叔丁基,它们任选由
下列取代基单至三取代:氟、氯、溴、甲氧基、乙氧基、甲硫基、
乙硫基(它们各任选由氟和/或氯取代),
或代表烯丙基、丁烯基、1-甲基烯丙基、炔丙基或1-甲基炔丙基,
它们各任选由氟或氯单至三取代;
或代表环丁基、环戊基或环己基,它们各任选由下列取代基单至六
取代:氟、氯、溴、甲氧基、乙氧基、苯基(它任选由氟、氯、溴、
氰基、甲基、乙基、正或异丙基、正、异、仲或叔丁基、三氟甲基、
甲氧基、乙氧基、正或异丙氧基、二氟甲氧基或三氟甲氧基取代)、
甲基、乙基、正或异丙基;
或代表苯基、萘基、苄基、呋喃基、苯并呋喃基、噻吩基、苯并噻
吩基、吡啶基、喹啉基、四氢呋喃基、全氢吡喃基,它们各任选单
至三取代,可能的取代基优选选自:
氟、氯、溴、氰基、硝基、甲基、乙基、正或异丙基、正、异、仲
或叔丁基、甲氧基、乙氧基、正或异丙氧基、甲硫基、乙硫基、正
或异丙硫基、甲基亚磺酰基、乙基亚磺酰基、甲磺酰基或乙磺酰基、
三氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟氯甲氧基、
三氟乙氧基、二氟甲硫基、二氟氯甲硫基、三氟甲硫基、三氟甲基
亚磺酰基或三氟甲磺酰基、乙酰基、丙酰基、乙酰氧基、甲氧羰基、
乙氧羰基、甲基磺酰氧基、乙基磺酰氧基、肟基甲基、肟基乙基、
甲氧基亚氨基甲基、乙氧基亚氨基甲基、甲氧基亚氨基乙基或乙氧
基亚氨基乙基;
三亚甲基(丙-1,3-二基)、亚甲二氧基或亚乙二氧基,它们各被键连
两次且各任选由相同或不同的下列取代基单或多取代:氟、氯、甲
基、三氟甲基、乙基或正或异丙基,R2、R5相同或不同且各代表氢、或代表甲基,R3 代表氢,或代表甲基、乙基,正或异丙基、正、异、仲或叔丁基,
它们各任选由下列取代基单至五取代:氟、氯、溴、氰基、羟基、
氨基、甲氧基、乙氧基、甲硫基、乙硫基、甲基亚磺酰基、乙基亚
磺酰基、甲磺酰基、乙磺酰基(它们各任选由氟和/或氯取代),
或代表烯丙基、丁烯基、1-甲基烯丙基、炔丙基或1-甲基炔丙基,
它们各任选由氟、氯或溴单至三取代;
或代表环丙基、环丁基、环戊基或环己基,它们各任选由下列取代
基单至六取代:氟、氯、溴、氰基、羧基、甲基、乙基、正或异丙
基、甲氧羰基或乙氧羰基,R4 代表甲基、乙基、正或异丙基、正、异、仲或叔丁基,它们各任选
由下列取代基单至五取代:氟、氯、溴、氰基、羟基、氨基、甲氧
基、乙氧基、甲硫基、乙硫基、甲基亚磺酰基、乙基亚磺酰基、甲
磺酰基、乙磺酰基(它们各任选由氟和/或氯取代),
或代表烯丙基、丁烯基、1-甲基烯丙基、炔丙基或1-甲基炔丙基,
它们各任选由氟、氯或溴单至三取代;
或代表环丙基、环丁基、环戊基或环己基,它们各任选由下列取代
基单至六取代:氟、氯、溴、氰基、羧基、甲基、乙基、正或异丙
基、甲氧羰基或乙氧羰基,R3和R4同与之相连的碳原子一起形成环丙基、环丁基、环戊基、环己
基,它们任选由下列取代基单至六取代:氟、氯、溴、氰基、羧基、
甲基、乙基、正或异丙基、甲氧羰基或乙氧羰基,且R6 代表环丙基、环丁基、环戊基或环己基,它们各任选由下列取代基
单至六取代:氟、氯、溴、氰基、羧基、甲基、乙基、甲氧基、乙
氧基、正或异丙基、甲氧羰基或乙氧羰基;
或代表苯基、萘基、苄基、苯乙基、呋喃基、苯并呋喃基、吡咯基、
吲哚基、噻吩基、苯并噻吩基、噁唑基、异噁唑基、噻唑基、异噻
唑基、噁二唑基、噻二唑基、吡啶基、喹啉基、嘧啶基、哒嗪基、
吡嗪基、环氧乙烷基、氧杂环丁烷基、四氢呋喃基、全氢吡喃基、
吡咯烷基、哌啶基或吗啉基,它们各任选单至三取代,可能的取代
基优选选自:
氟、氯、溴、氰基、硝基、氨基、羟基、甲酰基、羧基、氨基甲酰
基、硫代氨基甲酰基、甲基、乙基、正或异丙基、正、异、仲或叔
丁基、甲氧基、乙氧基、正或异丙氧基、甲硫基、乙硫基、正或异
丙硫基、甲基亚磺酰基、乙基亚磺酰基、甲磺酰基或乙磺酰基、三
氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟氯甲氧基、三
氟乙氧基、二氟甲硫基、二氟氯甲硫基、三氟甲硫基、三氟甲基亚
磺酰基或三氟甲磺酰基、甲氨基、乙氨基、正或异丙氨基、二甲氨
基、二乙氨基、乙酰基、丙酰基、乙酰氧基、甲氧羰基、乙氧羰基、
甲基磺酰氧基、乙基磺酰氧基、肟基甲基、肟基乙基、甲氧基亚氨
基甲基、乙氧基亚氨基甲基、甲氧基亚氨基乙基或乙氧基亚氨基乙
基;
各键连两次的三亚甲基(丙-1,3-二基)、亚甲二氧基或亚乙二氧基,
它们各任选由相同或不同的下列取代基单或多取代:氟、氯、甲基、
三氟甲基、乙基或正或异丙基;
环丙基、环丁基、环戊基或环己基。
5.根据权利要求1的式(I)化合物,其中A 代表单键或代表亚甲基、1,1-亚乙基、1,2-亚乙基、1,1-亚丙基、
1,2-亚丙基或2,2-亚丙基,Q1、Q2、Q3各代表氧,R1 代表甲基、乙基、正或异丙基、正、异、仲或叔丁基、环戊基、
环己基或代表任选由甲基、乙基、甲氧基、乙氧基、溴、氯或氟取
代的苯基或苄基,R2、R5各代表氢,R3 代表氢、甲基、乙基或环丙基,R4 代表甲基、乙基或环丙基,或R3和R4同与之相连的碳原子一起形成环戊烷环或环己烷环,且R6 代表环己基,它各任选由甲基、乙基、甲氧基或乙氧基单或二取代;
或代表苯基、萘基、呋喃基、苯并呋喃基、吡咯基、吲哚基、噻吩
基、苯并噻吩基、吡啶基、喹啉基、嘧啶基、哒嗪基、吡嗪基,它
们各任选单至三取代,可能的取代基优选选自:
氟、氯、溴、氰基、硝基、氨基、羟基、甲酰基、羧基、氨基甲酰
基、硫代氨基甲酰基、甲基、乙基、正或异丙基、正、异、仲或叔
丁基、甲氧基、乙氧基、正或异丙氧基、甲硫基、乙硫基、正或异
丙硫基、甲基亚磺酰基、乙基亚磺酰基、甲磺酰基或乙磺酰基、三
氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟氯甲氧基、三
氟乙氧基、二氟甲硫基、二氟氯甲硫基、三氟甲硫基、三氟甲基亚
磺酰基或三氟甲磺酰基、甲氨基、乙氨基、正或异丙氨基、二甲氨
基、二乙氨基、乙酰基、丙酰基、乙酰氧基、甲氧羰基、乙氧羰基、
甲基磺酰氧基、乙基磺酰氧基、肟基甲基、肟基乙基、甲氧基亚氨
基甲基、乙氧基亚氨基甲基、甲氧基亚氨基乙基或乙氧基亚氨基乙
基;
各键连两次的三亚甲基(丙-1,3-二基)、亚甲二氧基或亚乙二氧基,
它们各任选由相同或不同的下列取代基单或多取代:氟、氯、甲基、
三氟甲基、乙基或正或异丙基。
6.一种农药,其特征在于,它含有至少一种根据权利要求1的式(I)化合物。
7.防治有害生物的方法,其特征在于,使权利要求1的式(I)化合物作用于有害生物和/或其栖息地。
8.根据权利要求1至5的式(I)化合物防治有害生物的应用。
9.制备农药的方法,其特征在于,将权利要求1至5的式(I)化合物与填充剂和/或表面活性剂混合。
10.制备权利要求1的式(I)化合物的方法,其特征在于,使通式(II)的N-取代氨基酸其中Q1、Q2、Q3、R1、R2、R3和R4各具有权利要求1中所定义的含意,如果需要在反应助剂存在下,如果需要在稀释剂存在下,与通式(III)的胺反应其中A、R5和R6各具有权利要求1中所定义的含意。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19501841A DE19501841A1 (de) | 1995-01-23 | 1995-01-23 | Aminosäureamide |
DE19501841.9 | 1995-01-23 |
Publications (1)
Publication Number | Publication Date |
---|---|
CN1177345A true CN1177345A (zh) | 1998-03-25 |
Family
ID=7752047
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN96192263A Pending CN1177345A (zh) | 1995-01-23 | 1996-01-10 | 氨基酸酰胺衍生物及其作为农药的应用 |
Country Status (9)
Country | Link |
---|---|
US (1) | US5935979A (zh) |
EP (1) | EP0805798B1 (zh) |
JP (1) | JPH10512574A (zh) |
CN (1) | CN1177345A (zh) |
AU (1) | AU4485296A (zh) |
DE (2) | DE19501841A1 (zh) |
ES (1) | ES2143176T3 (zh) |
PL (1) | PL321454A1 (zh) |
WO (1) | WO1996022970A1 (zh) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102020592A (zh) * | 2010-11-26 | 2011-04-20 | 湖南科技大学 | 具有杀菌活性的氨基甲酸脲甲基取代芳基酯 |
CN106508936A (zh) * | 2015-09-15 | 2017-03-22 | 南京华洲药业有限公司 | 一种含苯噻菌胺和多菌灵的杀菌组合物及其应用 |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2000051998A1 (en) | 1999-03-02 | 2000-09-08 | Boehringer Ingelheim Pharmaceuticals, Inc. | Compounds useful as reversible inhibitors of cathepsin s |
US6420364B1 (en) | 1999-09-13 | 2002-07-16 | Boehringer Ingelheim Pharmaceuticals, Inc. | Compound useful as reversible inhibitors of cysteine proteases |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
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JPS63122659A (ja) * | 1986-11-13 | 1988-05-26 | S K I Baitsu Kk | α,β−デヒドロ−α−アミノ酸残基を有する特定物質の製造方法 |
DE3915755A1 (de) * | 1989-05-13 | 1990-11-29 | Bayer Ag | Fungizide mittel sowie substituierte aminosaeureamid-derivate und deren herstellung |
DE3936298A1 (de) * | 1989-11-01 | 1991-05-02 | Bayer Ag | Substituierte aminosaeureamid-derivate deren herstellung und verwendung |
DE4203084A1 (de) * | 1992-02-04 | 1993-08-05 | Bayer Ag | Substituierte aminosaeureamide |
-
1995
- 1995-01-23 DE DE19501841A patent/DE19501841A1/de not_active Withdrawn
-
1996
- 1996-01-10 WO PCT/EP1996/000071 patent/WO1996022970A1/de active IP Right Grant
- 1996-01-10 EP EP96900932A patent/EP0805798B1/de not_active Expired - Lifetime
- 1996-01-10 JP JP8522576A patent/JPH10512574A/ja active Pending
- 1996-01-10 DE DE59604115T patent/DE59604115D1/de not_active Expired - Fee Related
- 1996-01-10 CN CN96192263A patent/CN1177345A/zh active Pending
- 1996-01-10 US US08/875,035 patent/US5935979A/en not_active Expired - Fee Related
- 1996-01-10 PL PL96321454A patent/PL321454A1/xx unknown
- 1996-01-10 AU AU44852/96A patent/AU4485296A/en not_active Abandoned
- 1996-01-10 ES ES96900932T patent/ES2143176T3/es not_active Expired - Lifetime
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102020592A (zh) * | 2010-11-26 | 2011-04-20 | 湖南科技大学 | 具有杀菌活性的氨基甲酸脲甲基取代芳基酯 |
CN106508936A (zh) * | 2015-09-15 | 2017-03-22 | 南京华洲药业有限公司 | 一种含苯噻菌胺和多菌灵的杀菌组合物及其应用 |
Also Published As
Publication number | Publication date |
---|---|
US5935979A (en) | 1999-08-10 |
AU4485296A (en) | 1996-08-14 |
ES2143176T3 (es) | 2000-05-01 |
DE19501841A1 (de) | 1996-07-25 |
JPH10512574A (ja) | 1998-12-02 |
DE59604115D1 (de) | 2000-02-10 |
EP0805798A1 (de) | 1997-11-12 |
WO1996022970A1 (de) | 1996-08-01 |
PL321454A1 (en) | 1997-12-08 |
EP0805798B1 (de) | 2000-01-05 |
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