CN1212697A - 四氢嘧啶衍生物 - Google Patents
四氢嘧啶衍生物 Download PDFInfo
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- CN1212697A CN1212697A CN97192825A CN97192825A CN1212697A CN 1212697 A CN1212697 A CN 1212697A CN 97192825 A CN97192825 A CN 97192825A CN 97192825 A CN97192825 A CN 97192825A CN 1212697 A CN1212697 A CN 1212697A
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- Prior art keywords
- alkyl
- group
- formula
- alkenyl
- wantonly
- Prior art date
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- 229940058307 antinematodal tetrahydropyrimidine derivative Drugs 0.000 title claims abstract description 10
- 150000005326 tetrahydropyrimidines Chemical class 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 84
- -1 alkenyl halide Chemical group 0.000 claims abstract description 65
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 20
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 18
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000001301 oxygen Substances 0.000 claims abstract description 18
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 18
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 14
- 239000001257 hydrogen Substances 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 10
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 7
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 7
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 125000005108 alkenylthio group Chemical group 0.000 claims abstract description 5
- 125000003302 alkenyloxy group Chemical group 0.000 claims abstract description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 4
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims abstract description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract description 4
- 125000005110 aryl thio group Chemical group 0.000 claims abstract description 4
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 3
- 238000002360 preparation method Methods 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 33
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- 238000006243 chemical reaction Methods 0.000 claims description 14
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- 125000001188 haloalkyl group Chemical group 0.000 claims description 7
- 239000003513 alkali Substances 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- UQOKRDJILZMZKU-UHFFFAOYSA-N 2-nitropyrimidine Chemical class [O-][N+](=O)C1=NC=CC=N1 UQOKRDJILZMZKU-UHFFFAOYSA-N 0.000 claims description 5
- 239000004606 Fillers/Extenders Substances 0.000 claims description 3
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- 239000013543 active substance Substances 0.000 claims description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 3
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- 125000005291 haloalkenyloxy group Chemical group 0.000 claims description 3
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 3
- 239000002917 insecticide Substances 0.000 claims description 3
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 claims description 3
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims description 3
- 150000002500 ions Chemical class 0.000 claims description 2
- OTPDWCMLUKMQNO-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrimidine Chemical compound C1NCC=CN1 OTPDWCMLUKMQNO-UHFFFAOYSA-N 0.000 claims 5
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 abstract description 3
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- 125000005115 alkyl carbamoyl group Chemical group 0.000 abstract 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 1
- 125000006193 alkinyl group Chemical group 0.000 abstract 1
- 125000001769 aryl amino group Chemical group 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 125000004415 heterocyclylalkyl group Chemical group 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 15
- 239000003995 emulsifying agent Substances 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 230000000694 effects Effects 0.000 description 14
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- 241000894006 Bacteria Species 0.000 description 10
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- 241000209094 Oryza Species 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
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- 125000000335 thiazolyl group Chemical group 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 240000007124 Brassica oleracea Species 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
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- 241000500437 Plutella xylostella Species 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 125000002877 alkyl aryl group Chemical group 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 5
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
本发明涉及新的式(Ⅰ)的四氢嘧啶衍生物,其制备方法和其用作杀虫剂的用途,其中,A代表基团(Ⅰa)-(CH2)m-COXR1或(Ⅰb)(见右式)中的一个;Het代表五-或六-元的杂环基,其含有1、2、3或4个氮原子和/或1或2个氧原子或硫原子作为环杂原子-杂环原子数可以是1、2、3或4-,且它可任选被卤素、氰基、硝基、烷基、卤代烷基、链烯基、卤代链烯基、炔基、烷氧基、卤代烷氧基、链烯氧基、卤代链烯氧基、炔氧基、烷硫基、卤代烷硫基、烯硫基、卤代烯硫基、炔硫基、烷基亚磺酰基、卤代烷基亚磺酰基、烷基磺酰基、卤代烷基磺酰基、氨基、烷基氨基、二烷基氨基、芳基、芳氧基、芳硫基、芳氨基、芳烷基、甲酰基氨基、烷基羰基氨基、甲酰基、氨基甲酰基、烷基羰基和/或烷氧基羰基取代;R1代表氢、烷基、卤代烷基、链烯基、卤代链烯基,可任选取代的芳烷基或可任选取代的5-或6-元的杂环基烷基;R2代表可任选取代的烷基或芳烷基;X代表氧或基团-NH-和-N-烷基-;m代表从1到20的整数和;n代表0到2的整数;但除去下述化合物,其中同时地;A代表基团(Ⅰa);Het代表上述Ⅱ式;R1代表氢或乙基;X代表氧;m代表1或2和n代表0。
Description
本发明涉及新的四氢嘧啶衍生物,其制备方法及其防治有害动物的用途。
已知某些双环嘧啶衍生物,特别如,6-取代6,7-二氢-8-硝基-(5H)-1-(2-氯吡啶-5-基-甲基或2-氯-1,3-噻唑-5-基-甲基)-咪唑烷并-[2,3-f]-嘧啶,具有杀虫性能(例如参见:EP-A-0247477)。然而,这些化合物的活性和作用谱,特别是在低施用剂量和浓度下,不是完全的令人满意的。
本发明于是提供了新的式(Ⅰ)的四氢嘧啶衍生物
其中
中的一个
Het 代表五-或六-元杂环基,其中含有1、2、3或4个氮原
子和/或1或2个氧原子或硫原子作为环杂原子-环杂原子
数是1、2、3或4,且它可任选被卤素、氰基、硝基、烷
基、卤代烷基、链烯基、卤代链烯基、炔基、烷氧基、卤代
烷氧基、链烯氧基、卤代链烯氧基、炔氧基、烷硫基、卤代
烷硫基、链烯硫基、卤代链烯硫基、炔硫基、烷基亚磺酰基、
卤代烷基亚磺酰基、烷基磺酰基、卤代烷基磺酰基、氨基、
烷基氨基、二烷基氨基、芳基、芳氧基、芳硫基、芳氨基、
芳烷基、甲酰基氨基、烷基羰基氨基、甲酰基、氨基甲酰基、
烷基羰基和/或烷氧基羰基取代,R1 代表卤素,烷基,卤代烷基,链烯基,卤代链烯基,可任选
取代的芳烷基或可任选取代的5-或6-元杂环基烷基,R2 代表可任选取代的烷基或芳烷基,X 代表氧或-NH-和-N-烷基-基团,m 代表从1到20的整数且n 代表0到2的整数,但除去下述式(Ⅰ)化合物,其中同时地A 代表基团(Ⅰa),Het 代表R1 代表氢或乙基X 代表氧,m 代表1或2且n 代表0。而且,发现式(Ⅰ)的四氢嘧啶衍生物可以如下获得:a)使式(Ⅱ)的硝基亚甲基衍生物与式(Ⅲa)或(Ⅲb)的胺反应,
其中Het和n与上面定义的相同
H2N-(CH2)m-CO-X-R1 (Ⅲa)
其中
R1,R2,X和m与上述定义相同,
胺可任选以其氢卤化物形式,在至少两倍摩尔量的甲醛存在下,如果适合在酸催化剂存在下,和如果适合在稀释剂存在 下,和如果适合在碱存在下,进行反应;b) 使式(Ⅳ)的硝基嘧啶衍生物与式(Ⅴ)的化合物在碱存在
其中
A和n为上述定义,
Het-CH2-L (Ⅴ)
其中
Het为上述定义和
L代表阴离子离去基团。
最后,现已发现新的式(Ⅰ)的四氢嘧啶衍生物具有优越的生物活性且特别适合防治农业、林业、贮藏产品和材料的保护,以及卫生领域中出现的有害动物,特别是昆虫、蜱螨和线虫。
式(Ⅰ)提供了本发明四氢嘧啶衍生物的一般定义。
在上下文中提到的化学式中列出优选的取代基或基团范围说明如下:
Het优选代表五-或六-元基团,这组基团选自呋喃基、噻吩基、
吡咯基、吡唑基、咪唑基、1,2,3-或1,2,4-三唑基、噁唑
基、异噁唑基、1,2,4-或1,3,4-噁二唑基、噻唑基、异噻
唑基、1,2,3-、1,2,4-、1,2,5-或1,3,4-噻二唑基、吡
啶基、哒嗪基、嘧啶基和吡嗪基组成,其中每一个基团可任
选被相同或不同的取代基单或多取代,这组取代基是氟、氯、
溴、碘、氰基、硝基、C1-C4-烷基(其可任选被氟-和/
或氯-取代)、C2-C4-链烯基(其可任选被氟-和/或氯
-取代)、C2-C4-炔基、C1-C4-烷氧基(其可任选被
氟-和/或氯-取代)、C3-C4-链烯氧基(其可任选被氟
-和/或氯-取代)、C3-C4-炔氧基、C1-C4-烷硫基
(其可任选被氟-和/或氯-取代)、C3-C4-烯硫基(其
可任选被氟-和/或氯-取代)、C3-C4-炔硫基、C1-
C4烷基亚磺酰基(可任选被氟-和/或氯-取代)、C1-C4
烷基磺酰基(其可任选被氟-和/或氯-取代)、氨基、C1
-C4-烷基氨基、二-(C1-C4-烷基)-氨基、苯基、
苯氧基、苯硫基、苯氨基、苄基、甲酰氨基、C1-C4-烷基、
羰基氨基、甲酰基、氨基甲酰基、C1-C4-烷基-羰基和/
或C1-C4-烷氧基-羰基。R1 优选代表氢、C1-C12-烷基、C1-C6-卤代烷基、C2-
C6-链烯基,或C2-C6卤代链烯基,或可任选被一到五个
相同或不同的取代基取代的苯基-C1-C4-烷基,适合的苯
基取代基是:
卤素、氰基、硝基、C1-C4-烷基、C1-C4-烷氧基、C1
-C4-烷硫基、C1-C4-卤代烷基、C1-C4-卤代烷氧
基、C1-C4-卤代烷硫基、C1-C4-烷氧基羰基、氨基、
C1-C4-烷基氨基或二-(C1-C4-烷基)-氨基;
或可任选被一到三个相同或不同的取代基取代的5-或6-
元的杂环基-C1-C4-烷基基团、这组杂环基团是呋喃基、
噻吩基、吡咯基、吡唑基、咪唑基、1,2,3-或1,2,4-三唑
基、噁唑基、异噁唑基、1,2,4-或1,3,4-噁二唑基、噻唑
基、异噻唑基、1,2,3-、1,2,4-、1,2,5-或1,3,4-噻二
唑基、吡啶基、哒嗪基、嘧啶基和吡嗪基,其中每一个基团
可任选被相同或不同的取代基单至三取代,这组取代基是
氟、氯、溴、碘、氰基、硝基、C1-C4-烷基(其可任选被
氟-和/或氯-取代)、C2-C4-链烯基(其可任选被氟-
和/或氯-取代)、C2-C4-炔基、C1-C4-烷氧基(其
可任选被氟-和/或氯-取代)、C3-C4-链烯氧基(其可
任选被氟-和/或氯-取代)、C3-C4-炔氧基、C1-C4
-烷硫基(其可任选被氟-和/或氯-取代)、C3-C4-烯
硫基(其可任选被氟-和/或氯-取代)、C3-C4-炔硫
基、C1-C4-烷基亚磺酰基(其可任选被氟-和/或氯-取
代)、C1-C4-烷基磺酰基(其可任选被氟-和/或氯-取
代)、氨基、C1-C4-烷基氨基、二-(C1-C4-烷基)
-氨基、苯基、苯氧基、苯硫基、苯胺基、苄基、甲酰氨基、
C1-C4-烷基、羰基氨基、甲酰基、氨基甲酰基、C1-C4
-烷基-羰基和/或C1-C4-烷氧基-羰基。R2 优选代表C1-C8-烷基或可任选取代的苄基,X 优选代表氧或-NH-和-N-(C1-C8-烷基)-基团,m 优选代表1到12的整数,n 优选代表0到1,在此应除去下述化合物,其中同时地A 代表(Ⅰa)基,Het 代表R1 代表氢或乙基,X 代表氧,m 代表1或2且n 代表0。Het 特别优选代表吡唑基、1,2,4-三唑基、噁唑基、异噁唑基、
噻唑基、异噻唑基、1,2,5-噻二唑基、吡啶基、吡嗪基和嘧
啶基等五-或六-元杂环基团,其中每一个基团可任选被选
自氟、氯、溴、碘、氰基、C1-C2-烷基(其可任选被氟-
和/或氯-取代)、C1-C2-烷氧基(其可任选被氟-和/
或氯-取代)、C1-C2-烷硫基(其可任选被氟-和/或氯
-取代)和C1-C2-烷基磺酰基(其可任选被氟-和/或氯
-取代)相同或不同的取代基单一或三取代。R1 特别优选代表氢、C1-C8-烷基、C1-C4-卤代烷基、C2
-C4-链烯基,或C2-C4-卤代链烯基,或可任选被1到3
个相同或不同的取代基取代的苯基-C1-C2-烷基,适合的
苯基取代基是:氟、氯、溴、氰基、硝基、甲基、乙基、甲
氧基、甲基硫、三氟甲基、三氟甲氧基和三氟甲基硫;
或5-或6-元杂环基-C1-C2-烷基,其可任选被1到3
个相同或不同的取代基取代,杂环基团选自吡唑基、1,2,4-
噻唑基、噁唑基、异噁唑基、噻唑基、异噻唑基、1,2,5-噻
二唑基、吡啶基、吡嗪基和嘧啶基,其中每个基团可任选被
氟、氯、溴、氰基、硝基、C1-C2-烷基(其可任选被氟-
和氯-取代)、C1-C2-烷氧基(其可任选被氟-和氯-取
代)、C1-C2-烷硫基(其可任选被氟-和氯-取代)、和
C1-C2-烷基磺酰基(其可任选被氟-和氯-取代)取代。R2 特别优选代表C1-C4-烷基和可任选被卤素(氟、氯、溴)、
C1-C4-烷基、C1-C2-烷氧基、C1-C2-烷硫基、C1
-C2-卤代烷基、C1-C2-卤代烷氧基、C1-C2-卤代
烷硫基、硝基、氰基取代的苄基;X 特别优选代表氧或基团-NH-、-N(CH3)-和-N(C2H5)-。m 特别优选代表0到10的整数。n 特别优选代表0到1。在此应除去下述化合物,其中同时地A 代表基团(Ⅰa),Het 代表R1 代表氢或乙基,X 代表氧,m 代表1或2和n 代表0。Het 更特别优选代表吡啶基和噻唑基,其中每个基团可任选被1
到2个选自氟、氯和溴的相同或不同的取代基取代。R1 更特别优选代表氢、C1-C8-烷基,或可任选被1到2个相
同或不同的取代基取代的苄基,适合的取代基是:氟、氯、
溴、氰基、硝基、甲基、乙基、甲氧基、甲硫基、三氟甲基、
三氟甲氧基、和三氟甲硫基;
或吡啶基甲基和噻唑基甲基,其中每个基团可任选被1到2
个选自氟、氯和溴的相同或不同的取代基取代。R2 更特别优选代表C1-C4-烷基或苄基。X 更特别优选代表氧或-NH-基团。m 更特别优选代表1到8的整数。n 更特别优选代表0到1。在此应除去下述化合物,其中同时地A 代表基团(Ⅰa),Het 代表R1 代表氢或乙基,X 代表氧,m 代表1或2和n 代表0。
上述提及的一般的或优选的基团定义或说明的适用于终产物和相应地起始原料和中间体。这些基团的定义可根据要求相互结合,即各个优选范围的结合也是可能的。
本发明优选的是含有上述优选定义的组合的式(Ⅰ)化合物。
本发明特别优选的是含有上述特别优选定义的组合的式(Ⅰ)化合物。
本发明更特别优选的是含有上述更特别优选定义的组合的式(Ⅰ)化合物。
在上文和下文限定的基团中,烃基,如烷基或链烯基-,也可与杂原子连接如烷氧基或烷硫基-,在各种情况下,可以是直链或其可能的支链。
其中
Het1 代表可任选取代的吡啶基且
A 为本发明中限定的定义。
其中
Het1 代表可任选取代吡啶基且
A 为本发明中限定的定义。
其中
Het2 代表可任选取代的噻唑基且
A 为本发明中限定的定义。
其中
Het2 代表可任选取代的噻唑基且
A 为本发明中限定的定义。
其中
A 为上述优选,特别优选和更特别优选的定义。
其中
其中
其中
A为上述优选,特别优选和更特别优选的定义。
在根据本发明的方法(a)中被用作起始原料的分子式(Ⅱ)的硝基亚甲基衍生物是已知的(例如参见:EP-A0163855、EP-A0192060、EP-A0247477、EP-A0316843、EP-A0316845)和/或可通过已知方法制备的(参见:欧洲公开专利所述)。
如果硝基亚甲基衍生物以其氢卤化物的形式使用,优选用它们的氢氯化物。
在根据本发明的方法(a)中另外用作起始原料的式(Ⅲ-a)和(Ⅲ-b)的胺是有机化学合成通常已知的和/或可通过常规方法得到的。
在根据本发明的方法(b)中被用作初始原料的式(Ⅳ)的硝基嘧啶是从未公开的。它们可通过式(Ⅱa)的硝基亚甲基衍生物(例如参见:EP-A0247477)与用于方法(a)的式(Ⅲ-a)和(Ⅲ-b)的胺反应得到,
其中
n为上述定义。
在根据本发明的方法(b)中另外被用作起始原料的化合物是通过式(Ⅴ)一般地定义。L优选地代表氯、溴、碘、乙酸基、甲苯磺酰基或甲磺酰基。式(Ⅴ)的化合物是有机化学中通常已知的物质。
本发明的方法(a)优选使用稀释剂进行。在此反应中适合的稀释剂是水和惰性有机溶剂。其优选为脂肪族的和芳香族的,可任选卤化的烃,如戊烷,己烷,庚烷,环己烷,石油醚,汽油,粗汽油,苯,甲苯,二甲苯,二氯甲烷,二氯乙烷,氯仿,四氯化碳,氯苯和邻-二氯苯,醚类,如二乙醚和二丁醚,乙二醇二甲醚和二乙二醇二甲醚,四氢呋喃和二噁烷,醇类,如甲醇,乙醇,正丙醇和异丙醇。优选使用醇和水的混合物。
如果适合,根据本发明的方法(a)是在酸性、非氧化的催化剂存在下进行。氢卤酸如氢氯酸和氢溴酸,磷酸,和低级羧酸如乙酸和丙酸,被证明是特别有用的。
根据本发明的方法(a)的反应温度可以在相对宽的范围内变化。通常,本方法在-20℃至+120℃之间,优选0℃至80℃的温度之间进行。
根据本发明的方法(a)通常在大气压下进行。然而,它同样可以在加压或减压下进行。
当进行根据本发明的方法(a)时,对每摩尔的式(Ⅱ)的硝基亚甲基衍生物通常使用1到1.5mol,优选1到1.2mol的式(Ⅲ)的胺和2到4mol,优选2到3mol的甲醛。
如果适合,式(Ⅲ)的胺可以采用作水溶液。如果使用式(Ⅲ)的气态胺,这些化合物可通入稀释剂、式(Ⅱ)化合物和甲醛的混合物中。在本发明的方法中,甲醛采用水溶液。此反应通常在适合的稀释剂下进行,且反应混合物在每种情况要求的温度下搅拌数小时。本发明方法的后处理,在各种情况下,可在通常方式下进行。
根据本发明的方法(b)优选使用稀释剂进行。适合的稀释剂实际上是所有的惰性有机溶剂。特别是脂肪族的和芳香族的,可任选卤化的烃,如戊烷、己烷、庚烷、环己烷、石油醚、汽油、粗汽油、苯、甲苯、二甲苯、二氯甲烷、二氯乙烷、氯仿、四氯化碳、氯苯和邻-二氯苯,醚类,如二乙醚和二丁醚、乙二醇二甲醚和二乙二醇二甲醚、四氢呋喃和二噁烷,酮类,如丙酮、甲基乙基酮、甲基异丙基酮或甲基异丁基酮,酯类,如乙酸甲酯、乙酸乙酯,腈类,例如,乙腈或丙腈,酰胺类,例如,二甲基甲酰胺、二甲基乙酰胺和N-甲基吡咯烷酮,和二甲亚砜、环丁砜或六甲基磷三酰胺。
根据本发明的方法(a)和(b)中适合的碱是常规用于这类反应的酸结合剂。优选使用碱金属氢化物和碱土金属氢化物,如氢化锂、氢化钠、氢化钾或氢化钙,碱金属氢氧化物或碱土金属氢氧化物,如氢氧化锂、氢氧化钠、氢氧化钾或氢氧化钙,碱金属碳酸盐或碳酸氢盐或碱土金属碳酸盐或碳酸氢盐,如碳酸钠或碳酸氢钠或碳酸钾或碳酸氢钾或碳酸钠,碱金属乙酸盐,如乙酸钠或乙酸钾,碱土金属醇盐,如叔-丁醇钠或叔-丁醇钾,还有碱性含氮化合物,如三甲胺、三乙胺、三丙胺、三丁胺、二异丁胺、二环己胺、乙基二异丙胺、乙基二环己胺、N,N-二甲基苄胺、N,N-二甲基苯胺、吡啶、2-甲基-、3-甲基-、4-甲基-、2,4-二甲基-、2,6-二甲基-、2-乙基-、4-乙基-和5-乙基-2-甲基-吡啶、1,5-二氮杂二环[4.3.0]-壬-5-烯(DBN)、1,8-二氮杂二环-[5.4.0]-十-碳-7-烯(DBN)或1,4-二氮杂二环-[2.2.2]-辛烷(DABCO)。
本发明的方法(b)的反应温度可在相对宽的范围内变化。通常反应进行的温度在0℃到100℃之间,优选温度在10℃和80℃之间。
本发明的方法(b)通常在大气压下进行。然而,它同样可以在加压或减压下进行。
本发明的方法(b)所需要的起始原料通常用大约等摩尔数。然而,在各种情况下也可以使两种组分中的一种相对大的过量。本反应通常在酸受体存在下的适合的稀释剂中进行,且在各种情况下,反应混合物在所需温度下搅拌数小时。用常规的方法进行后处理。
本活性化合物适合防治有害动物,特别是在农业、森林业、储藏产品和材料的保护,和卫生领域中遇到的昆虫,蜱螨类和线虫,这些活性化合物具有好的植物耐受性并对温血动物低毒。它们优选用作作物保护剂。它们对正常敏感和抗性品系以及对所有或一些发育阶段都有活性。上述有害动物包括:
等足目:例如,潮虫、平甲虫和带鼠妇。
倍足目:例如,具斑马陆。
唇足目:例如,食果地蜈蚣和蚰蜒。
综合目:例如,庭园么蚰。
缨尾目:例如,西洋衣鱼。
弹尾目:例如,具刺跳虫。
直翅目:例如,东方蜚蠊、美洲大蠊、马得拉蜚蠊、德国小蠊、家蟋蟀、蝼蛄属、热带飞蝗、长额负蝗和蚱蜢。
革翅目:例如,欧洲球螋。
等翅目:例如,犀白蚁属。
虱目: 例如,体虱、血虱属和颚虱属。
食毛目:例如,畜虱属和啮毛虱。
缨翅目:例如,温室条蓟马和烟蓟马。
半翅目:例如,褐盾蝽属、中棉红蝽、甜菜拟网蝽、臭虫、长红蜡蝽和锥蝽属。
同翅目:例如,甘蓝粉虱、棉粉虱、温室白粉虱、棉蚜、甘蓝蚜、茶藨隐瘤额蚜、甜菜蚜、苹果蚜、苹果绵蚜、桃大尾蚜、葡萄根瘤蚜、瘿绵蚜属、麦长管蚜、瘤额蚜属、忽布疣蚜、粟缢管蚜、微叶蝉属、纹叶蝉、黑尾叶蝉、水土坚蚧、榄珠蜡蚧、灰飞虱、稻褐飞虱、红肾圆盾蚧、春藤园蚧、粉蚧属和木虱属。
鳞翅目:例如,棉红铃虫、松天蛾、冬尺蛾、苹果细蛾、苹果巢蛾、小菜蛾、黄褐天幕毛虫、黄毒蛾、毒蛾属、棉潜叶蛾、桔潜叶蛾、地老虎属、切根虫属、夜蛾属、棉斑实夜蛾、棉铃虫属、甜菜夜蛾、甘蓝夜蛾、小眼夜蛾、斜纹夜蛾、粘虫属、粉纹夜蛾、苹果蠹蛾、粉蝶属、禾草螟属、玉米螟、地中海粉螟、大蜡螟、负袋衣蛾、织网衣蛾、褐织夜蛾、亚麻黄卷蛾、烟卷蛾、云杉卷夜蛾、葡萄果蠹蛾、茶长卷夜蛾和栎纵卷夜蛾。
鞘翅目:例如,具斑窃蠹、谷蠹、豆象、大豆象、家天牛、赤杨紫跳甲、马铃薯甲虫、辣根猿叶甲、条叶甲属、油菜跳甲、墨西哥豆甲、隐翅甲属、锯谷盗、花象甲属、米象属、葡萄黑耳喙象、香蕉根叶甲、甘蓝荚象甲、苜蓿叶象甲、皮蠹属、黑皮蠹属、圆皮蠹属、黑毛皮蠹属、粉蠹属、油菜花露尾甲、蛛甲属、金黄蛛甲、麦蛛甲、拟谷盗属、黄粉甲、叩甲属、宽胸叩甲属、西方五月鳃角金龟、马铃薯鳃角金龟和新西兰肋翅鳃角金龟。
膜翅目:例如,锯角叶蜂属、叶蜂属、田蚁属、小家蚁和胡蜂属。
双翅目:例如,伊蚊属、按蚊属、库蚊属、黄猩猩果蝇、家蝇属、厩蝇属、红头丽蝇、绿蝇属、金蝇属、疽蝇属、胃蝇属、虱蝇属、螫蝇属、鼻蝇属、皮蝇属、虻属、螗蜩属、花园毛蚊、瑞典麦杆蝇、麦花蝇属、甜菜潜叶蝇、地中海实蝇、油橄榄实蝇和欧洲大蚊。
蚤目:例如,东方鼠蚤和栉头蚤属。
蛛形纲:例如,蝎和盗蛛和黑寡妇球腹蛛。
蜱螨目:例如,粗脚粉螨、隐喙蜱、钝喙蜱属、鸡皮刺螨、茶藨兔瘿螨、桔锈螨、牛蜱属、头蜱属、花蜱属、璃眼蜱属、硬蜱属、痒螨属、皮痒螨属、疥螨属、跗线螨属、苜蓿苔螨、全爪螨属和红叶螨属。
对植物有害的线虫包括短体属、相似穿孔线虫、起绒线茎线虫、半穿刺线虫、异皮线虫属、球异皮线虫属、根线属、滑刃属、长针属、剑线虫属和毛刺属。
根据本发明式(Ⅰ)化合物具有特别突出的杀虫活性。
它们用于防治损害植物的昆虫特别有效,上述昆虫例如为辣根猿叶甲幼虫(Phaedon cochleariae)、小菜蛾幼虫(Plutella maculipennis),黑尾叶蝉(Nephotettix cinctriceps)、草地粘虫幼虫(Spodopterafrugiperda)或桃蚜(Myzus persicae)。
本活性化合物可被转化成为常规的制剂,如液剂、乳剂、可湿性粉剂、悬浮剂、粉剂、细粉剂、可溶粉剂、颗粒剂、浓悬浮乳剂、用活性化合物浸渍的天然和合成材料、在聚合物中的微细胶囊。
这些制剂是以已知方法生产的,例如,通过将活性成分与增量剂,即液体溶剂和/或固体载体混合而生产,制剂中可任选使用表面活性剂,即乳化剂和/或分散剂、和/或成泡剂。
在使用水作为增量剂的情况下,例如,也可使用有机溶剂作为助溶剂。适当的液体溶剂主要有:芳香烃类,如二甲苯、甲苯或烷基萘,氯代芳烃类和氯代脂肪烃类,如氯苯、二氯乙烷或二氯甲烷,脂肪烃类,如环己烷或烷属烃,例如矿物油馏份、矿物油和植物油,醇类,如丁醇或乙二醇及其醚和酯类,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。
适当的固体载体有:例如,铵盐和天然矿物粉末,如高岭土、粘土、滑石、白垩、石英、硅镁土、蒙脱土或硅藻土,和合成矿物粉末,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有:例如,粉碎和分级的天然岩石,如方解石、大理石、浮石、海泡石和白云石,以及无机和有机粉末的合成颗粒,和有机材料的颗粒如锯末、坚果壳、玉米穗茎和烟草茎;适当的乳化剂和/或发泡剂有: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、芳基磺酸盐以及蛋白水解产物;适合的分散剂有:例如木质素亚磺酸废液和甲基纤维素。
在制剂中还可使用粘着剂如羧甲基纤维素和粉末、颗粒或胶乳状的天然和合成聚合物,如阿拉伯树胶、聚乙烯醇和聚乙酸乙烯酯,以及天然磷脂如脑磷脂和卵磷脂,和合成磷脂。其它的粘着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,和痕量营养物如金属盐,例如,铁、锰、硼、铜、钴、钼和锌盐。
制剂中通常含有按重量计0.1%-95%,优选按重量计0.5%-90%的活性化合物。
根据本发明的活性化合物可以其市售制剂和从上述制剂制备的应用形式,以及与其它活性化合物的混合物的形式存在,其它活性化合物如杀虫剂、引诱剂、消毒剂、杀细菌剂、杀螨剂、杀线虫剂、杀真菌剂、植物生长调节剂或除草剂。例如,杀虫剂包括:磷酸酯、氨基甲酸酯、羧酸酯、卤代烃类、苯基脲类和从微生物中生产的物质等。
特别优选的成分的实例为下述: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-苯氧基苯基)-乙酰胺;8-羟基喹啉硫酸盐、(E)-2-{2-[6-(2-氰基苯氧基)-嘧啶基-4-基氧]-苯基}-3-甲氧丙烯酸甲酯;(E)-甲氧亚氨基[α-(对甲苯氧基)-对甲苯基]乙酸甲酯;2-苯基苯酚;艾敌吗啉、氨丙磷酸、氨丙磷酸钾、敌菌灵、戊环唑,
苯霜灵、麦锈灵、苯菌灵、乐杀螨、联苯酚、双苯三唑醇、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、苄氯三唑醇、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、吡硫菌、灭菌磷、二噻农、多果定、敌菌酮,
克瘟散、环氧唑(epoxiconazole)、乙菌克、氯唑灵,
乙嘧菌醇、苯氰唑、呋菌胺、种衣酯、拌种咯、苯锈定、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、乙磷钠、四氯苯酞、麦穗宁、呋霜灵、拌种胺,
双胍辛,
氯苯嘧啶醇、己唑醇、土菌消,
抑霉唑、酰胺唑、双胍辛醋酸盐、异稻瘟净、异稻瘟净、异菌脲、稻瘟灵,
春雷霉素、铜制剂如氢氧化铜、环烷酸铜、碱式氯化铜、硫酸铜、氧化铜、喹啉铜和波尔多混合物,
锰铜混剂、代森锰锌、代森锰、嘧菌胺、灭锈胺、甲霜灵、metconazole、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、稻病磷、四氯苯酞、多马霉素、粉病灵、多氧霉素、噻菌灵、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、三唑酮、三唑醇、唑菌嗪、杨菌胺、三环唑、环玛克啉、氟菌唑、嗪氨灵、triticonazole,
有效霉素、乙烯菌核利,
代森锌、福美锌。杀细菌剂:
溴硝丙二醇、双氯酚、氯定、福美镍、春雷霉素、异噻菌酮、呋喃羧酸、土霉素、噻菌灵、链霉素、白叶减、硫酸铜和其它铜制剂。杀虫剂/杀螨剂/杀线虫剂:
齐墩螨素(abamectin)、AC303630、乙酰甲胺磷、氟酯菊酯、棉铃威、涕灭威、甲体氯氰菊酯、虫螨醚、印楝素、谷硫磷、乙基谷硫磷、环唑锡,
苏云菌芽孢杆菌、噁虫威、丙硫克百威、杀虫磺、β-氟氯氰菊酯、联苯菊酯、丁苯威、溴醚菊酯(brofenprox)、溴硫磷、混戊混、噻嗪酮、丁酮威、哒嗪酮,
硫线磷、西维因、呋喃丹、三硫磷、丁硫克百成、杀螟丹、CGA157419、CGA184699、除线威、chlorethoxyfos、毒虫威、定虫隆、氯甲磷、毒死蜱、甲基毒死蜱、顺-苄呋菊酯、三氟氯氰菊酯、四螨嗪、杀螟腈、乙氰菊酯、氟氯氰菊酯、氯氟氰菊酯、三环锡、氯氰菊酯、灭蝇胺,
溴氰菊酯、内吸磷、甲基内吸磷、甲基内吸磷S赶磷酸酯、杀螨隆、二嗪农、除线磷、敌敌畏、dicliphos、百治磷、乙硫磷、伏虫脲、乐果、甲基毒虫威、敌杀磷、乙拌磷、克瘟散、emamectin、高氰戊菊酯、苯虫威、乙硫磷、醚菊酯、灭线磷、氯嘧啶磷,
克线磷、喹螨醚、杀螨锡、杀螟松、仲丁威、苯硫威、双氧威、甲氰菊酯、fenpyrad、唑螨酯、倍硫磷、氰戊菊酯、氟虫腈、氟定胺、氟螨脲、氟氰戊菊酯、氟虫脲、氟醚菊酯(flufenprox)、氟胺氰菊酯、地虫磷、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,
吡虫啉、异稻瘟净、氯唑磷、丙胺磷、异丙威、异噁唑磷、伊维菌素、α-三氟氯氰菊酯、lufenuron,
马拉硫磷、灭蚜磷、速灭磷、甲丙硫磷、蜗牛敌、虫螨畏、甲胺磷、杀扑磷、灭虫威、灭多威、速灭威、米倍尔霉素、久效磷、moxidectin,
二溴磷、NC184、NI25、nitenpyram,
氧化乐果、甲叉丙威、砜吸磷、异砜磷,
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、哒嗪酮、嘧螨醚、蚊蝇磷,
喹硫磷,
RH 5992,
水杨硫磷、硫线磷、氟硅菊酯、治螟磷、异丙硫磷,
虫酰肼、吡螨胺、特丁嘧啶硫磷、伏虫隆、七氟菊酯、双硫磷、叔丁威、特丁甲拌磷、杀虫威、thiafenox、硫双灭多威、特氨叉威、甲基乙拌磷、治线磷、triazuron、敌百虫、杀虫隆、三叉威,
蚜灭多、二甲威、二甲苯威、YI 5301/5302、zetamethrin、
与其它已知活性成分,如除草剂的混合物,或与肥料和生长调节剂的混合物也是可能的。
根据本发明的活性化合物还可以其市售制剂和从上述制剂制备的应用形式,以及与增效剂的混合物的形式存在。增效剂是能够增加活性化合物活性,但加入的增效剂本身不需要有活性的化合物。
从市售制剂制备的应用形式中活性化合物的含量可在很宽的范围内变化。使用形式中活性化合物的浓度为按重量计0.0000001至95%的活性化合物,优选按重量计0.0001至1%。
本化合物以适用于使用形式的常规方法进行使用。
当用于防治卫生害虫和储藏产品的害虫时,本活性化合物对木材和粘土具有极好的残留活性,以及对石灰物质中的碱性有好的稳定性。
根据本发明的活性化合物不仅对植物害虫,卫生领域害虫和储藏产品害虫具有活性,而且在兽医领域,对防治动物寄生虫(外寄生虫)也有活性,例如蜱、隐喙蜱、马疥螨、恙螨科、蝇(叮咬和吸食)、寄生性蝇幼虫、虱、头虱、鸟虱和蚤。上述寄生虫包括:
虱目,例如盲虱属、颚虱属、头虱属、体虱属、盲虱属。
食毛目、钝角亚目和细角亚目,例如毛鸟虱属、短角鸟虱属、毛虱属、牛羽虱属、Werneckiella spp.、Lepikentron spp.、畜虱属、啮毛虱属、猫虱属。
双翅目、长角亚目和短角亚目,例如伊蚊属、按蚊属、库蚊属、蚋属、真蚋属、白蛉属、卢蚊属、库蠓属、斑虻属、瘤虻属、黄虻属、虻属、麻虻属、Philipomyia spp.、蜂蝇属、家蝇属、齿股蝇属、螫蝇属、血蝇属、Morellia spp.、厩蝇属、毛蝇属、丽蝇属、绿蝇属、彩眼蝇属、肉蝇属、麻蝇属、鼻蝇属、皮蝇属、胃蝇属、虱蝇属、蜱蝇属和刺蝇属。
蚤目,例如蚤属、栉头虱属、鼠蚤属、毛列蚤属。
半翅目,例如臭虫属、猎蝽属、红腹猎蝽属、全圆蝽属。
蜚蠊目,例如东方蜚蠊、美洲大蠊、德国蜚蠊、棕带蜚蠊属。
蜱螨亚纲和后-和中胸气门目,例如隐喙螨属、喙蜱属、残喙蜱属、硬蜱属、花蜱属、牛蜱属、革蜱属、血蜱属、眼玻蜱属、扇头蜱属、刺螨属、刺利螨属、肺刺螨属、胸口螨属、瓦螨属。
Actinedida目(口叶前气门)和蜱螨目(Astigmata),例如蜂盾螨属、姬螫螨属、禽螫螨属、肉螨属、疮螨属、蠕形螨属、恙螨属、牦螨属、粉螨属、食酪螨属、嗜木螨属、颈下螨属、翅螨属、瘙螨属、痒螨属、耳癞螨属、疥螨属、痂螨属、疙螨属、胞螨属和皮膜螨属。
根据本发明使用的式(Ⅰ)活性化合物也适用于防治侵扰农业家畜的节肢动物,农业家畜如牛、绵羊、山羊、马、猪、驴、骆驼、水牛、免、鸡、火鸡、鸭、鹅和蜜蜂,其它家养动物,例如狗、猫、笼养鸟和水族馆的鱼,还有所谓的试验动物,例如田鼠、豚鼠、大鼠和小鼠。通过防治上述节肢动物,旨在减少动物死亡和减产(肉、奶、毛、皮、蛋、蜜等),因此,通过使用本发明的活性化合物,可以使畜牧业更经济、更简单。
在兽医部门,根据本发明的活性化合物可用已知方法给药,即经肠给药,例如以片剂、胶囊剂、饮剂、灌药剂、颗粒剂、膏剂、大丸剂、饲养过程和栓剂等形式进行;非经肠给药(肌肉注射、皮下注射、静脉注射、腹膜内注射等)、植入法;经鼻给药,经皮给药,例如以浸泡或洗浴、喷雾、泼上或擦上、洗涤和撒粉形式进行,也可借助于还有活性化合物的成型制品,例如项圈、耳饰物、尾饰物、肢环(带)、笼头、装饰器具等。
当用于牛,家禽,家养动物等时,其中含有按重量计1至80%活性化合物的式(Ⅰ)活性化合物制剂形式(例如粉剂,乳剂,悬浮剂),可直接使用或稀释100至10,000倍后使用,或以化学浴的形式使用。
而且,已发现根据本发明的式(Ⅰ)化合物对损坏工业材料的昆虫具有强的杀虫活性。
下述,以非限定的形式,举例说明优选被处理的昆虫:
甲虫,如
北美家天牛、黄虎天牛、家具窃蠹、报死窃蠹、梳角细脉窃蠹、Dendrobium pertinex、松窃蠹、Priobium carpini、欧洲竹粉蠹、美洲粉蠹、平颈粉蠹、桴粉蠹、柔毛粉蠹、Trogoxylon aequale、鳞毛粉蠹;材小蠹、Tryptodendron spec.、咖啡黑长蠹、槲长蠹、暗褐长蠹、长蠹和竹长毒蠹。
革翅目,如
钢青小树蜂、枞大树蜂、Urocerus gigas taignus和Urocerus augur。
白蚁,如
木白蚁、麻头堆砂白蚁、灰点异白蚁、黄胸散白蚁、黄胸散白蚁、避光散白蚁、达尔文澳州白蚁、湿木古白蚁、台湾家白蚁。
衣鱼如西洋衣鱼。
在本发明中,工业材料可理解为无生命的材料,优选如,聚合物,胶,胶料,纸和纸板,皮革,木材和木制品,和油漆。
受保护免受昆虫攻击的材料特别优选为木材和木制品。
可被根据本发明的组分或包括这种组分的混合物保护的木材和木制品例如为:建筑木材、木梁、枕木、桥梁组件、栈桥、木质运载工具、盒、地铺、容器、电线杆、绝缘材料、木窗和木门、胶合板、聚合板、接头,或通常用于房屋建筑或细木工的木材制品。
本活性化合物可以浓缩物形式或常规制剂形式使用,如粉剂,颗粒剂,液剂,悬浮剂,乳剂或糊剂。
上述制剂可通过现有技术中已知的方法制备,例如,将活性化合物与至少一种溶剂或稀释剂,乳化剂,分散剂和/或粘着剂或固定剂,防水剂混合,如果需要与干燥剂和紫外线稳定剂混合,如果需要与着色剂和颜料,和其它的助剂混合。
用于保护木头或木材的杀虫组合物或浓缩物含有浓度为按重量计0.0001至95%,特别是按重量计0.001至60%的根据本发明活性化合物。
组合物或浓缩物的使用量根据出现的昆虫的种类和所处介质而确定。最佳的使用量在每种情况下根据一系列试验而确定。可是,通常在被保护材料上使用按重量计0.0001至20%,优选按重量计0.001至10%的活性化合物就足够了。
使用的溶剂和/或稀释剂为有机化学溶剂或溶剂混合物和/或低挥发性油性或油样的有机化学溶剂或溶剂混合物和/或极性有机化学溶剂或溶剂混合物和/或水,如果适合,可使用乳化剂和/或湿润剂。
使用的有机化学溶剂优选为挥发度大于35和闪点大于30℃,优选大于45℃的油性或油样溶剂。用作上述不溶于水的低挥发性油性或油样溶剂的物质为适合的矿物油或其芳香馏份或包含溶剂混合物的矿物油,优选石油溶剂,石油和/或烷基萘。
优选使用的物质是沸点范围为170至220℃的矿物油,沸点范围为170至220℃的石油溶剂,沸点范围为250至350℃的锭子油,沸点范围为160至280℃的石油或芳香烃,松节油等。
在优选的实施方案中,可使用熔点范围为180至210℃的液体脂肪烃或沸点范围为180至220℃的芳烃和脂肪烃的高沸点混合物和/或锭子油和/或单氯萘,优选α-单氯萘。
挥发度大于35和闪点大于30℃,优选大于45℃的低挥发性有机油性或油样溶剂,可部分的被高挥发性的有机化学溶剂代替,条件是溶剂混合物也是挥发度大于35和闪点大于30℃,优选大于45℃的,和杀虫剂/杀真菌剂混合物溶于或乳化于该溶剂中。
在优选的实施方案中,部分有机化学溶剂或溶剂混合物被极性脂族有机化学溶剂或溶剂混合物代替。优选使用的物质为含有羟基和/或酯和/或醚基脂族有机化学溶剂,例如乙二醇醚,酯等。
在本发明范围内使用的有机化学粘着剂为本身已知的合成树脂粘着性的干性油和/或它们可用水稀释和/或在使用的有机化学溶剂中可溶,可分散或乳化的,优选的粘着剂包括或包含丙烯酸树脂,乙烯树脂,例如聚乙酸乙烯酯,聚酯树脂,聚缩合或聚加合树脂,聚尿烷树脂,烷基树脂或改性烷基树脂,苯酚树脂,烃树脂,如茚-香豆素酮树脂,硅氧烷树脂,干性植物油和/或干性油和/或以天然和/或合成树脂为基础的物理干性粘着剂。
用作粘着剂的合成树脂可以乳液,分散液或溶液形式使用。还可用作粘着剂的物质为用量多达按重量计10%的沥青或沥青物质。另外,也可使用的现有技术中已知的着色剂、颜料、防水剂、去味剂、和抑制剂或防腐剂等。
根据本发明的组合物或浓缩物优选包括,至少一种烷基树脂或改性烷基树脂和/或干性植物油作为有机化学粘着剂。根据本发明优选使用的物质是油含量超过按重量计45%,优选按重量计50至68%醇酸树脂。
所有的或一些上述粘着剂可被固定剂(混合物)或增塑剂(混合物)代替。上述添加剂的可防止活性化合物的挥发或结晶或沉淀。它们优选代替0.01至30%的粘着剂(以使用的100%粘着剂为基础)
增塑剂是属于下述化学类的物质:邻苯二甲酸酯如邻苯二甲酸二丁基酯、邻苯二甲酸二辛基酯、邻苯二甲酸苄基丁基酯,磷酸酯,如磷酸三丁基酯,己二酸酯如二-(2-乙基己基)己二酸酯,硬酯酸酯如硬酯酸丁基酯或硬酯酸戊基酯,油酸酯如油酸丁基酯,甘油醚或高分子量甘油醚、甘油酯,和对甲苯磺酸酯。
固定剂是以聚乙烯烷基醚为基础的化学物质,例如聚乙烯甲基醚,或酮类如二苯甲酮和亚乙基二苯甲酮。
水同样特别适合作为溶剂或稀释剂,如果需要也可以是水在一或多种上述有机化学溶剂或稀释剂、乳化剂和分散剂的混合物。
通过工业规模的浸渍方法,例如真空,双真空或加压工艺可得到对木材特别有效的保护。
如果适合,现用组合物中可包含其它杀虫剂和,如果需要还可加入一或多种杀真菌剂。
可混合的其它成分优选为描述在WO 94/29268中的杀虫剂和杀真菌剂。上述文件中所述化合物是本申请特别参考的部分。
可以混合的更特别优选的成分是杀虫剂如毒死蜱、辛硫磷、silafluofin、甲体氯氢菊酯、氟氯氰菊酯、氯氰菊酯、溴氰菊酯、氯菊酯、吡虫啉、NI-25、氟虫脲、氟铃脲和杀虫隆、和杀真菌剂、如环氧唑(epoxyconazole)、己唑醇、戊环唑、丙环唑、戊环唑、环唑醇、metconazol、抑霉唑、苯氟磺胺、对甲抑菌灵、氨基甲酸3-碘-2-丙炔基丁基酯、N-辛基-异噻唑啉-3-酮和4,5-二氯-N-辛基异噻唑啉-3-酮。
通过下述实施例,将本发明的物质的制备和用途予以说明。制备实施例:实施例1(方法a)
将5.0g(19.6mmol)的3-(2-氯吡啶-5-基-甲基)-2-硝基-亚甲基-咪唑烷,3.0g(23.9mmol)的甘氨酸甲酯盐酸盐和3.3ml三乙胺与3.6ml浓度为37%的甲醛溶液一起溶解在30ml乙醇中,并且加热回流5小时。
使反应混合物冷却,通过减压蒸去溶剂来浓缩。残余物加水搅拌,抽吸滤出并干燥。
将在20ml乙腈中的1.5g(5.86mmol)的6,7-二氢-6-乙氧基羰基-甲基-8-(5H)-咪唑烷并-[2,3-f]-嘧啶(实施例Ⅳ-1)用1.6g碳酸钾和1.0g(6.0mmol)的2-氯-5-氯甲基噻唑处理。反应混合物在40℃下搅拌6小时。然后滤出不溶解物并将溶液蒸发至干燥。残余物用柱色谱纯化。
将在30ml乙醇中的2.0g(20.2mmol)的2-硝基亚甲基-咪唑烷与2.8g(20.1mmol)甘氨酸乙酯盐酸盐,2.7ml三乙胺和4ml浓度37%的甲醛混合,一起加入并加热回流10小时。将冷却反应混合物冷却,并通过蒸馏掉溶剂来浓缩。残余物在水和二乙醚之间分配,分离出有机相,用无水硫酸钠干燥并浓缩。
得到的2.0g的6,7-二氢-6-乙氧基羰基甲基-8-硝基-(5H)-咪唑烷并-[2,3-f]-嘧啶,熔点为155-158℃。
通过实施例1和2的方法和通常制备的用法说明,获得列于下表1中的式(Ⅰ)化合物:表1
*)Lg.P=在溶剂辛醇和水之间,物质的分配系数P的对数,通过反相HPLC实验测定。
通过实施例2的方法和根据通常制备的用法说明,获得列于下表2中的式(Ⅳ)化合物:
表2
应用实施例
实施例号 | n | m | X | R1 | 物理常数 |
Ⅳ-2 | 0 | 1 | O | CH3 | Mp 183-85℃ |
在下面的应用实施例中,列在下面的化合物作为参考化合物:
(所有化合物公开在EP-A0247477中)实施例A
辣根猿叶甲幼虫试验
溶剂: 7重量份的 二甲基甲酰胺
乳化剂: 1重量份的 烷基芳基聚乙二醇醚
为了生产活性化合物的适合的制剂,将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,并用水稀释浓缩物至所需浓度。
将甘蓝叶(Brassica oleracea)浸沾在所需浓度的活性化合物的制剂中,进行处理,在叶面保持湿润的情况下移入辣根猿叶甲幼虫(Phaedoncochlearia)。
在一段确定的时间后,确定死亡率%。100%意为所有猿叶甲幼虫被杀死;0%意为没有猿叶甲幼虫被杀死。
在此试验中,各自在3天后,例如用制备实施例1,3,4,7,9,10,11,12,14,19,20,22和23的活性化合物,在0.001%的示范活性化合物浓度下,死亡率为100%,同时已知化合物(A),(B),(C)和(E)分别对幼虫无活性,死亡率仅30%,死亡率仅40%和死亡率仅20%。实施例B小菜蛾试验
溶剂: 7重量份的 二甲基甲酰胺
乳化剂: 1重量份的 烷基芳基聚乙二醇醚
为了生产活性化合物的适合的制剂,将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,并用水稀释浓缩物至所需浓度。
将甘蓝叶(Brassica oleracea)浸沾在所需浓度的活性化合物的制剂中,进行处理,在叶面保持湿润的情况下移入小菜蛾幼虫(Plutellamaculipennis)。
在一段确定的时间后,确定死亡率%。100%意为所有幼虫被杀死;0%意为没有幼虫被杀死。
在此试验中,各自在3天后,例如用制备实施例1,6,8,9,10,11,12,13,14,15,17,19,21和22的活性化合物,在0.01%的示范活性化合物浓度下,死亡率为100%,同时已知化合物(E)未显示活性。实施例C粘虫试验
溶剂: 7重量份的 二甲基甲酰胺
乳化剂: 1重量份的 烷基芳基聚乙二醇醚
为了生产活性化合物的适合的制剂,将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,并用水稀释浓缩物至所需浓度。
将甘蓝叶(Brassica oleracea)浸沾在所需浓度的活性化合物的制剂中,进行处理,在叶面保持湿润的情况下移入粘虫幼虫(Spodopterafrugiperda)。
在一段确定的时间后,确定死亡率%。100%意为所有幼虫被杀死;0%意为没有幼虫被杀死。
在此试验中,各自在3天后,例如用制备实施例8,9,10,11,12,14,15,19和20的活性化合物,在0.001%的示范活性化合物浓度下,死亡率为100%,同时已知化合物(A),(D)和(F)未显示活性,且(B),(C)和(G)的死亡率仅为30%。实施例D黑尾叶蝉试验
溶剂: 7重量份的 二甲基甲酰胺
乳化剂: 1重量份的 烷基芳基聚乙二醇醚
为了生产活性化合物的适合的制剂,将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,并用水稀释浓缩物至所需浓度。
将水稻秧苗(Oryza sative)浸沾在所需浓度的活性化合物的制剂中,进行处理,在叶面保持湿润的情况下移入黑尾叶蝉幼虫(Nephotettix cincticeps)。
在一段确定的时间后,确定死亡率%。100%意为所有幼虫被杀死;0%意为没有幼虫被杀死。
在此试验中,各自在6天后,例如用制备实施例6,7,8,9,10,14,15,16,17和18的活性化合物,在0.0001%的示范活性化合物浓度下,死亡率为100%,同时已知的活性化合物(E)的死亡率仅为20%。实施例E桃蚜试验
溶剂: 7重量份的 二甲基甲酰胺
乳化剂: 1重量份的 烷基芳基聚乙二醇醚
为了生产活性化合物的适合的制剂,将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,并用水稀释浓缩物至所需浓度。将被桃蚜(Myzus persicae)侵染的蚕豆(Vicia faba)浸沾在所需浓度的活性化合物的制剂中,然后放入塑料盘中。
在一段确定的时间后,确定死亡率%。100%意为所有幼虫被杀死;0%意为没有幼虫被杀死。
在此试验中,下述制备实施例的化合物得到的死亡率如下:各自在处理1天后,在0.001%的示范活性化合物浓度下,1=99%,4=80%,6和16=90%,15=98%,19=95%和20=100%,同时已知的活性化合物(E)和(F)的死亡率分别仅为10%和无活性。
Claims (9)
1.式(Ⅰ)的四氢嘧啶衍生物
其中
Het 代表五-或六-元的杂环基,其含有1、2、3或4个氮原子和/或1或2个氧原子或硫原子作为环杂原子-杂环原子数可以是1、2、3或4-,且它可任选被卤素、氰基、硝基、烷基、卤代烷基、链烯基、卤代链烯基、炔基、烷氧基、卤代烷氧基、链烯氧基、卤代链烯氧基、炔氧基、烷硫基、卤代烷硫基、烯硫基、卤代烯硫基、炔硫基、烷基亚磺酰基、卤代烷基亚磺酰基、烷基磺酰基、卤代烷基磺酰基、氨基、烷基氨基、二烷基氨基、芳基、芳氧基、芳硫基、芳氨基、芳烷基、甲酰基氨基、烷基羰基氨基、甲酰基、氨基甲酰基、烷基羰基和/或烷氧基羰基取代,
R1 代表氢、烷基、卤代烷基、链烯基、卤代链烯基,可任选取代的芳烷基或可任选取代的5-或6-元的杂环基烷基,
R2 代表可任选取代的烷基或芳烷基,
X 代表氧或基团-NH-和-N-烷基-,
m 代表从1到20的整数和
n 代表0到2的整数,
但除去下述化合物,其中同时地
A 代表基团(Ⅰa),
Het代表
R1 代表氢或乙基
X 代表氧,
m 代表1或2和
n 代表0。
其中
Het 代表五-或六-元的杂环基,其含有1、2、3或4个氮原子和/或1或2个氧原子或硫原子作为环杂原子-杂环原子数可以是1、2、3或4-,且它可任选被卤素、氰基、硝基、烷基、卤代烷基、链烯基、卤代链烯基、炔基、烷氧基、卤代烷氧基、链烯氧基、卤代链烯氧基、炔氧基、烷硫基、卤代烷硫基、烯硫基、卤代烯硫基、炔硫基、烷基亚磺酰基、卤代烷基亚磺酰基、烷基磺酰基、卤代烷基磺酰基、氨基、烷基氨基、二烷基氨基、芳基、芳氧基、芳硫基、芳氨基、芳烷基、甲酰基氨基、烷基羰基氨基、甲酰基、氨基甲酰基、烷基羰基和/或烷氧基羰基取代,
R1 代表氢,烷基,卤代烷基,链烯基,卤代链烯基,可任选取代的芳烷基或可任选取代的5-或6-元的杂环基烷基,
R2 代表可任选取代的烷基或芳烷基,
X 代表氧或基团-NH-和-N-烷基-,
m 代表从1到20的整数和
n 代表0到2的整数,
但除去下述化合物,其中同时地
A 代表基团(Ⅰa),
R1 代表氢或乙基,
X 代表氧,
m 代表1或2和
n 代表0
其特征在于
a)使式(Ⅱ)的硝基亚甲基衍生物与(Ⅲ a)或(Ⅲ b)的胺反应,
其中
Het和n如上述定义
其中
R1,R3,X和m为上述定义,
胺可任选以其氢卤化物形式,在至少两倍摩尔量的甲醛存在下,如果适合在酸催化剂存在下和如果适合在稀释剂存在下和如果适合在碱存在时,进行反应;
其中A为上述定义的,
Het-CH2-L (Ⅴ)
其中Het为上述定义的且
L代表离子离去基团。
5.杀虫剂,其特征在于,其含有至少一种根据权利要求1的式(Ⅰ)的四氢嘧啶。
6.根据权利要求1的式(Ⅰ)四氢嘧啶防治有害动物的用途。
7.防治有害动物的方法,其特征在于,使根据权利要求1的式(Ⅰ)四氢嘧啶作用在害虫和/或它们的栖息处。
8.杀虫剂的制备方法,其特征在于,将根据权利要求1的式(Ⅰ)的四氢嘧啶与增量剂和/或表面活性剂混合。
9.根据权利要求1的式(Ⅰ)的四氢嘧啶制备杀虫剂的用途。
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19608243.9 | 1996-03-04 | ||
DE19608243 | 1996-03-04 | ||
DE19651429A DE19651429A1 (de) | 1996-03-04 | 1996-12-11 | Tetrahydropyrimidin-Derivate |
DE19651429.0 | 1996-12-11 |
Publications (1)
Publication Number | Publication Date |
---|---|
CN1212697A true CN1212697A (zh) | 1999-03-31 |
Family
ID=26023456
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN97192825A Pending CN1212697A (zh) | 1996-03-04 | 1997-02-19 | 四氢嘧啶衍生物 |
Country Status (10)
Country | Link |
---|---|
US (1) | US6177431B1 (zh) |
EP (1) | EP0885225B1 (zh) |
JP (1) | JP2000506846A (zh) |
CN (1) | CN1212697A (zh) |
AU (1) | AU1874797A (zh) |
BR (1) | BR9707911A (zh) |
CA (1) | CA2248018A1 (zh) |
ES (1) | ES2170362T3 (zh) |
IL (1) | IL125904A0 (zh) |
WO (1) | WO1997032878A1 (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111662282A (zh) * | 2019-03-07 | 2020-09-15 | 湖南化工研究院有限公司 | 氮杂环并吡啶类化合物及其中间体 |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ZW5085A1 (en) | 1984-04-13 | 1985-09-18 | Nihon Tokushu Noyaku Seizo Kk | Nitromethylene derivatives,intermediates thereof,processes for production thereof,and insecticides |
ATE67493T1 (de) | 1985-02-04 | 1991-10-15 | Bayer Agrochem Kk | Heterocyclische verbindungen. |
US5001138B1 (en) | 1985-02-04 | 1998-01-20 | Bayer Agrochem Kk | Heterocyclic compounds |
US5204360A (en) | 1985-02-04 | 1993-04-20 | Nihon Bayer Agrochem K.K. | Heterocyclic compounds |
DE3638121A1 (de) | 1986-05-30 | 1987-12-03 | Bayer Ag | 1,2,3,6-tetrahydro-5-nitro-pyrimidin-derivate |
PH25616A (en) | 1987-11-18 | 1991-08-08 | Bayer Ag | 1,2,3,4-tetrahydro-5-nitro-pyrimidine derivatives |
DE3739264A1 (de) | 1987-11-18 | 1989-06-01 | Bayer Ag | 2-chlor-1,3-thiazol-5-yl-methyl substituierte nitrogruppenhaltige imidazolidino-1,2,3,4-tetrahydropyrimidine bzw. hexahydropyrimidino-1,2,3,4-tetrahydropyrimidine |
-
1997
- 1997-02-19 CN CN97192825A patent/CN1212697A/zh active Pending
- 1997-02-19 BR BR9707911A patent/BR9707911A/pt not_active IP Right Cessation
- 1997-02-19 EP EP97905050A patent/EP0885225B1/de not_active Expired - Lifetime
- 1997-02-19 US US09/125,998 patent/US6177431B1/en not_active Expired - Fee Related
- 1997-02-19 IL IL12590497A patent/IL125904A0/xx unknown
- 1997-02-19 WO PCT/EP1997/000775 patent/WO1997032878A1/de active IP Right Grant
- 1997-02-19 AU AU18747/97A patent/AU1874797A/en not_active Abandoned
- 1997-02-19 ES ES97905050T patent/ES2170362T3/es not_active Expired - Lifetime
- 1997-02-19 JP JP9531394A patent/JP2000506846A/ja not_active Ceased
- 1997-02-19 CA CA002248018A patent/CA2248018A1/en not_active Abandoned
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111662282A (zh) * | 2019-03-07 | 2020-09-15 | 湖南化工研究院有限公司 | 氮杂环并吡啶类化合物及其中间体 |
CN111662282B (zh) * | 2019-03-07 | 2021-07-06 | 湖南化工研究院有限公司 | 氮杂环并吡啶类化合物及其中间体 |
Also Published As
Publication number | Publication date |
---|---|
CA2248018A1 (en) | 1997-09-12 |
US6177431B1 (en) | 2001-01-23 |
WO1997032878A1 (de) | 1997-09-12 |
ES2170362T3 (es) | 2002-08-01 |
BR9707911A (pt) | 1999-07-27 |
JP2000506846A (ja) | 2000-06-06 |
AU1874797A (en) | 1997-09-22 |
EP0885225A1 (de) | 1998-12-23 |
EP0885225B1 (de) | 2002-01-23 |
IL125904A0 (en) | 1999-04-11 |
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