CN111433192A - 杀微生物的苯基脒衍生物 - Google Patents
杀微生物的苯基脒衍生物 Download PDFInfo
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- CN111433192A CN111433192A CN201880077724.2A CN201880077724A CN111433192A CN 111433192 A CN111433192 A CN 111433192A CN 201880077724 A CN201880077724 A CN 201880077724A CN 111433192 A CN111433192 A CN 111433192A
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- ethyl
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- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
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- QPDUQKTYZRXRBC-UHFFFAOYSA-N triazole-4-thione Chemical class S=C1C=NN=N1 QPDUQKTYZRXRBC-UHFFFAOYSA-N 0.000 description 1
- ZBZJXHCVGLJWFG-UHFFFAOYSA-N trichloromethyl(.) Chemical compound Cl[C](Cl)Cl ZBZJXHCVGLJWFG-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/14—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- 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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/20—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom three- or four-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/02—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D305/04—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D305/06—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/06—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/20—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/12—Radicals substituted by halogen atoms or nitro or nitroso radicals
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catching Or Destruction (AREA)
- Furan Compounds (AREA)
- Epoxy Compounds (AREA)
Abstract
披露了具有式(I)的化合物,其中取代基是如权利要求1中所定义的。此外,本发明涉及包含具有式(I)的化合物的农用化学组合物,涉及这些组合物的制备,并且涉及所述化合物或组合物在农业或园艺中用于对抗、预防或控制植物、收获的粮食作物、种子或非生命材料被植物病原性微生物、特别是真菌侵染的用途。
Description
本发明涉及杀微生物的苯基脒衍生物,例如作为活性成分,所述苯基脒衍生物具有杀微生物活性,特别是杀真菌活性。本发明还涉及这些苯基脒衍生物的制备,涉及在这些苯基脒衍生物的制备中有用的中间体,涉及这些中间体的制备,涉及包括这些苯基脒衍生物中至少一种的农用化学组合物,涉及这些组合物的制备并且涉及这些苯基脒衍生物或组合物在农业或园艺中用于控制或防止植物、收获的粮食作物、种子或非生命材料被植物病原性微生物、特别是真菌侵染的用途。
在WO 2000/046184中描述了某些杀真菌的苯基脒化合物。
现在已经出人意料地发现某些新颖的苯基脒衍生物具有有利的杀真菌特性。
因此,本发明提供了具有式(I)的化合物
其中
R1和R2各自独立地选自C1-C4烷基和C3-C8环烷基;或者
R1和R2与它们所附接的氮原子一起形成三元至六元饱和的环状基团;
R3是氢、卤素或C1-C4烷基;
R4和R5各自独立地选自氢和C1-C4烷基;或者
R4和R5与它们所附接的碳原子一起形成羰基(C=O);
X是O、S或NCH3;
n是0或1;
以及其盐、金属络合物、立体异构体和N-氧化物。
在第二方面,本发明提供了一种农用化学组合物,所述组合物包含具有式(I)的化合物。
具有式(I)的化合物可以用于控制植物病原性微生物。因此,为了控制植物病原体,可以将根据本发明的具有式(I)的化合物、或包含具有式(I)的化合物的组合物直接施用到所述植物病原体、或植物病原体的场所,特别是易受植物病原体攻击的植物。
因此,在第三方面,本发明提供了如本文描述的具有式(I)的化合物、或包含具有式(I)的化合物的组合物用于控制植物病原体的用途。
在另一个方面,本发明提供了控制植物病原体的方法,所述方法包括将如本文所描述的具有式(I)的化合物、或包含具有式(I)的化合物的组合物施用到所述植物病原体、或所述植物病原体的场所,特别是易受植物病原体攻击的植物。
具有式(I)的化合物在控制植物病原性真菌上是特别有效的。
因此,在又另一个方面,本发明提供了如本文描述的具有式(I)的化合物、或包含具有式(I)的化合物的组合物用于控制植物病原性真菌的用途。
在另一个方面,本发明提供了控制植物病原性真菌的方法,所述方法包括将如本文所描述的具有式(I)的化合物、或包含具有式(I)的化合物的组合物施用到所述植物病原性真菌、或所述植物病原性真菌的场所、特别是易受植物病原性真菌攻击的植物。
在取代基被指示为任选地被取代的情况下,这意指它们可以带有或可以不带有一个或多个相同的或不同的取代基,例如一至四个取代基。通常地,同时存在不多于三个这样的任选的取代基。优选地,同时存在不超过两个这样的任选的取代基(即,所述基团可以任选地被一个或两个指示为“任选的”的取代基取代)。在“任选的取代基”基团是较大的基团的情况下,如环烷基或苯基,最优选的是仅存在一个这样的任选的取代基。在基团被指示为被取代时,例如烷基,这包括是其他基团的一部分的那些基团,例如烷硫基中的烷基。
术语“卤素”是指氟、氯、溴或碘,优选是氟、氯或溴。
烷基取代基(单独或作为较大基团的一部分,如烷氧基-、烷硫基-)可以是直链的或支链的。取决于提到的碳原子的数量,烷基其本身或作为另一取代基的部分是例如甲基、乙基、正丙基、正丁基、正戊基、正己基和它们的异构体,例如异丙基、异丁基、仲丁基、叔丁基或异戊基。
环烷基取代基可以是饱和的或部分不饱和的,优选地是完全饱和的,并且是例如环丙基、环丁基、环戊基或环己基。
卤代烷基(单独或作为较大基团的一部分,例如卤代烷基氧基)可能包含一个或多个相同或不同的卤素原子并且,例如,可以代表CH2Cl、CHCl2、CCl3、CH2F、CHF2、CF3、CF3CH2、CH3CF2、CF3CF2或CCl3CCl2。
烷氧基意指基团-OR,其中R是正如以上所定义的烷基。烷氧基包括,但不限于:甲氧基、乙氧基、1-甲基乙氧基、丙氧基、丁氧基、1-甲基丙氧基和2-甲基丙氧基。
在具有式(I)的化合物中存在一个或多个可能的不对称碳原子意指化合物能以光学异构体形式(即对映异构体或非对映异构体的形式)存在。作为围绕单键的受限旋转的结果,还可能存在阻转异构体。式(I)旨在包括所有那些可能的异构形式及其混合物。本发明包括具有式(I)的化合物的所有那些可能的异构体形式及其混合物。同样地,式(I)旨在包括所有可能的互变异构体。本发明包括具有式(I)的化合物的所有可能的互变异构形式。
在每种情况下,根据本发明的具有式(I)的化合物是处于游离形式、被氧化的形式如N-氧化物、或盐的形式(例如农艺学上可用的盐的形式)。
N-氧化物是叔胺的氧化形式或含氮杂芳香族化合物的氧化形式。例如,A.Albini和S.Pietra于1991年在博卡拉顿(Boca Raton)CRC出版社出版的名为“Heterocyclic N-oxides[杂环N-氧化物]”一书中描述了它们。
R1、R2、R3、R4、R5、X和n的优选值以其任何组合如下所示:
优选地,R1和R2各自独立地是C1-C4烷基。
更优选地,R1和R2各自独立地选自甲基、乙基和异丙基。
甚至更优选地,R1是甲基、乙基或异丙基,并且R2是甲基或乙基。
最优选地,R1是乙基或异丙基并且R2是甲基。
优选地,R3是卤素或C1-C3烷基。
更优选地,R3是氟、氯或甲基。
甚至更优选地,R3是氯或甲基。
最优选地,R3是甲基。
优选地,R4和R5各自独立地选自氢和甲基,或R4和R5与它们所附接的碳原子一起形成羰基。
更优选地,R4和R5都是氢,或R4和R5与它们所附接的碳原子一起形成羰基。
最优选地,R4和R5都是氢。
优选地,X是O或S。
最优选地,X是O。
最优选地,n是1。
提供了根据本发明的实施例,如下面列出的。
实施例1提供了如以上所定义的具有式(I)的化合物,或其盐、立体异构体或N-氧化物。
实施例2提供了根据实施例1所述的化合物,或其盐、立体异构体或N-氧化物,其中R1和R2各自独立地是C1-C4烷基。
实施例3提供了根据实施例1或2所述的化合物,或其盐、立体异构体或N-氧化物,其中R3是卤素或C1-C3烷基。
实施例4提供了根据实施例1、2或3中任一项所述的化合物,或其盐、立体异构体或N-氧化物,其中R4和R5各自独立地选自氢和甲基,或R4和R5与它们所附接的碳原子一起形成羰基。
实施例5提供了根据实施例1、2、3或4中任一项所述的化合物,或其盐、立体异构体或N-氧化物,其中X是O或S。
实施例6提供了根据实施例1、2、3、4或5中任一项所述的化合物,或其盐、立体异构体或N-氧化物,其中R1和R2各自独立地选自甲基、乙基和异丙基。
实施例7提供了根据实施例1、2、3、4、5或6中任一项所述的化合物,或其盐、立体异构体或N-氧化物,其中R3是氟、氯或甲基。
实施例8提供了根据实施例1、2、3、4、5、6或7中任一项所述的化合物,或其盐、立体异构体或N-氧化物,其中R4和R5都是氢,或R4和R5与它们所附接的碳原子一起形成羰基。
实施例9提供了根据实施例1、2、3、4、5、6、7或8中任一项所述的化合物,或其盐、立体异构体或N-氧化物,其中R1是甲基、乙基或异丙基并且R2是甲基或乙基。
实施例10提供了根据实施例1、2、3、4、5、6、7、8或9中任一项所述的化合物,或其盐、立体异构体或N-氧化物,其中R3是氯或甲基。
实施例11提供了根据实施例1、2、3、4、5、6、7、8、9或10中任一项所述的化合物,或其盐、立体异构体或N-氧化物,其中R1是乙基或异丙基并且R2是甲基。
实施例12提供了根据实施例1、2、3、4、5、6、7、8、9、10或11中任一项所述的化合物,或其盐、立体异构体或N-氧化物,其中R3是甲基。
实施例13提供了根据实施例1、2、3、4、5、6、7、8、9、10、11或12中任一项所述的化合物,或其盐、立体异构体或N-氧化物,其中R4和R5都是氢。
实施例14提供了根据实施例1、2、3、4、5、6、7、8、9、10、11、12或13中任一项所述的化合物,或其盐、立体异构体或N-氧化物,其中n是1。
实施例15提供了根据实施例1、2、3、4、5、6、7、8、9、10、11、12、13或14中任一项所述的化合物,或其盐、立体异构体或N-氧化物,其中X是O。
根据本发明的一组优选的化合物是具有式(I-1)的那些,其是具有式(I)的化合物,其中
R1和R2各自独立地是C1-C4烷基;
R3是卤素或C1-C3烷基;
R4和R5各自独立地选自氢和甲基,或R4和R5与它们所附接的碳原子一起形成羰基;
X是O、S或NCH3;
n是0或1;
或其盐、立体异构体或N-氧化物。
根据此实施例的一组化合物是具有式(I-1a)的化合物,其是具有式(I-1)的化合物,其中X是O。
根据此实施例的另一组化合物是具有式(I-1b)的化合物,其是具有式(I-1)的化合物,其中X是S。
根据此实施例的另一组化合物是具有式(I-1c)的化合物,其是具有式(I-1)的化合物,其中X是NCH3。
根据本发明的另一组优选的化合物是具有式(I-2)的那些,其是具有式(I)的化合物,其中
R1和R2各自独立地选自甲基、乙基和异丙基;
R3是氟、氯或甲基;
R4和R5都是氢,或R4和R5与它们所附接的碳原子一起形成羰基;
X是O、S或NCH3;
n是0或1;
或其盐、立体异构体或N-氧化物。
根据此实施例的一组化合物是具有式(I-2a)的化合物,其是具有式(I-2)的化合物,其中X是O。
根据此实施例的另一组化合物是具有式(I-2b)的化合物,其是具有式(I-2)的化合物,其中X是S。
根据此实施例的另一组化合物是具有式(I-2c)的化合物,其是具有式(I-2)的化合物,其中X是NCH3。
根据本发明的另一组优选的化合物是具有式(I-3)的那些,其是具有式(I)的化合物,其中
R1是甲基、乙基或异丙基并且R2是甲基或乙基;
R3是氯或甲基;
R4和R5都是氢,或R4和R5与它们所附接的碳原子一起形成羰基;
X是O、S或NCH3;
n是0或1;
或其盐、立体异构体或N-氧化物。
根据此实施例的一组化合物是具有式(I-3a)的化合物,其是具有式(I-3)的化合物,其中X是O。
根据此实施例的另一组化合物是具有式(I-3b)的化合物,其是具有式(I-3)的化合物,其中X是S。
根据此实施例的另一组化合物是具有式(I-3c)的化合物,其是具有式(I-3)的化合物,其中X是NCH3。
根据本发明的另一组优选的化合物是具有式(I-4)的那些,其是具有式(I)的化合物,其中
R1是乙基或异丙基并且R2是甲基;
R3是甲基;
R4和R5都是氢;
X是O或S;
n是0或1(优选地n是1);
或其盐、立体异构体或N-氧化物。
根据此实施例的一组化合物是具有式(I-4a)的化合物,其是具有式(I-4)的化合物,其中X是O。
根据此实施例的另一组化合物是具有式(I-4b)的化合物,其是具有式(I-4)的化合物,其中X是S。
某些优选的具有式(I)的化合物是:
N-乙基-N’-[5-羟基-2-甲基-4-[2-(三氟甲基)四氢呋喃-2-基]苯基]-N-甲基-甲脒;
N’-[5-羟基-2-甲基-4-[2-(三氟甲基)四氢呋喃-2-基]苯基]-N-异丙基-N-甲基-甲脒;
N’-[2-氯-5-羟基-4-[2-(三氟甲基)四氢呋喃-2-基]苯基]-N-乙基-N-甲基-甲脒;
N-乙基-N’-[5-羟基-2-甲基-4-[4-氧代-2-(三氟甲基)四氢呋喃-2-基]苯基]-N-甲基-甲脒;
N-乙基-N’-[5-羟基-2-甲基-4-[2-(三氟甲基)四氢噻吩-2-基]苯基]-N-甲基-甲脒;
N-乙基-N’-[5-羟基-2-甲基-4-[2-(三氟甲基)氧杂环丁烷-2-基]苯基]-N-甲基-甲脒。
根据本发明的化合物可以具有许多益处,尤其包括针对保护植物对抗由真菌引起的疾病的有利水平的生物活性或对于用作农用化学品活性成分的优越特性(例如,更高的生物活性、有利的活性谱、增加的安全性、改进的物理-化学特性、或增加的生物可降解性)。
在下表1至4中阐明了具有式(I)的化合物的具体实例。
在下表P之后的表1至4中的每一个使得48种具有式(I-A)的化合物可得
其中R2、R3、X和n是如(下面)表P中所定义的,并且R4和R5是分别如表1至4中所定义的。
因此表1个体化了48种具有式(I-A)的化合物,其中对于表P的每一行,R4和R5是如在表1中定义的;类似地,表2个体化了48种具有式(I-A)的化合物,其中对于表P的每一行,R4和R5是如在表2中所定义的;表3和4以此类推。
表P
表1:此表披露了48种具有式I-A的化合物1.01至1.48,其中R4和R5都是氢,并且其中变量R2、R3、X和n具有在表P的相应行中给出的具体含义。例如,化合物1.01具有以下结构:
表2:此表披露了48种具有式I-A的化合物2.01至2.48,其中R4和R5都是甲基,并且其中变量R2、R3、X和n具有在表P的相应行中给出的具体含义。
表3:此表披露了48种具有式I-A的化合物3.01至3.48,其中R4和R5都是乙基,并且其中变量R2、R3、X和n具有在表P的相应行中给出的具体含义。
表4:此表披露了48种具有式I-A的化合物4.01至4.48,其中R4和R5一起形成羰基,并且其中变量R2、R3、X和n具有在表P的相应行中给出的具体含义。
本发明的化合物可以如在以下方案中所示来制备,其中(除非另外说明)每一变量的定义是如以上针对具有式(I)的化合物所定义的。
具有式(I)的化合物(其中R1、R2、R3、R4、R5、X和n是如针对式(I)所定义)可以通过经由若干已知的方法转化具有式(II)化合物(其中R3、R4、R5、X和n是如针对式(I)所定义)来获得,在这些方法中最广泛使用的是以下:
a)在0℃与100℃之间的温度下在有机溶剂如甲苯或甲醇中用具有式(III-a)的化合物处理,其中R1和R2是如针对式(I)所定义,并且R6是C1-C4烷基。
b)在20℃与100℃之间的温度下在有机溶剂如甲醇中用具有式(III-b)的原酸酯(其中R6是C1-C4烷基)处理,接着用具有式(III-c)的胺(其中R1和R2是如针对式(I)所定义)处理。
c)在-20℃与40℃之间的温度下在惰性溶剂如二氯甲烷中用具有式(III-d)的甲酰胺(其中R1和R2是如针对式(I)所定义)和活化剂如POCl3处理
这在下面的方案1中示出。
方案1
具有式(II)的化合物(其中R3、X和n是如针对式(I)所定义的并且R4和R5是氢)可以通过在还原条件下例如通过催化氢化转化具有式(IV)的化合物(其中R3、X和n是如针对式(I)所定义的)来获得。这在下面的方案2中示出。
方案2
具有式(IV)的化合物(其中R3、X和n是如针对式(I)所定义的)可以通过在烯烃复分解的条件下用过渡金属催化剂体系转化具有式(V)的化合物(其中R3、X和n是如针对式(I)所定义的)来获得。这在下面的方案3中示出。
方案3
具有式(V)的化合物(其中R3和X是如针对式(I)所定义的并且n是1)可以通过用具有式(VII)的化合物(其中R7是卤素,优选氯或溴)与碱转化具有式(VI)的化合物(其中R3和X是如针对式(I)所定义的)来获得。这在下面的方案4中示出。
方案4
可替代地,具有式(I)的化合物(其中R1、R2、R3、X和n是如针对式(I)所定义的并且R4和R5是氢)可以通过在还原条件下例如通过催化氢化转化具有式(VIII)的化合物(其中R1、R2、R3、X和n是如针对式(I)所定义的)来获得。这在下面的方案5中示出。
方案5
具有式(VIII)的化合物(其中R1、R2、R3、X和n是如针对式(I)所定义的)可以通过在烯烃复分解的条件下用过渡金属催化剂体系转化具有式(IX)的化合物(其中R1、R2、R3、X和n是如针对式(I)所定义的)来获得。这在下面的方案6中示出。
方案6
具有式(IX)的化合物(其中R1、R2、R3和X是如针对式(I)所定义的并且n是1)可以通过用具有式(VII)的化合物(其中R7是卤素,优选氯或溴)与碱转化具有式(X)的化合物(其中R1、R2、R3和X是如针对式(I)所定义的)来获得。这在下面的方案7中示出。
方案7
具有式(X)的化合物(其中R1、R2、R3和X是如针对式(I)所定义的)可以通过用具有式(XII)的化合物(其中R8是MgBr或Li)转化具有式(XI)的化合物(其中R1、R2、R3和X是如针对式(I)所定义的)来获得。这在下面的方案8中示出。
方案8
具有式(XI)的化合物(其中R1、R2和R3是如针对式(I)所定义的并且X是O)可以通过用具有式(XIV)的化合物与强碱(如丁基锂)转化具有式(XIII)的化合物(其中R1、R2和R3是如针对式(I)所定义的并且R7是卤素,优选溴或碘)来获得。这在下面的方案9中示出。
方案9
具有式(XIII)的化合物(其中R1、R2和R3是如针对式(I)所定义并且R7是卤素,优选溴或碘)可以通过经由若干已知的方法转化具有式(XV)的化合物(其中R3是如针对式(I)所定义并且R7是卤素,优选溴或碘))来获得,在这些方法中最广泛使用的是以下:
a)在0℃与100℃之间的温度下在有机溶剂如甲苯或甲醇中用具有式(III-a)的化合物处理,其中R1和R2是如针对式(I)所定义,并且R6是C1-C4烷基。
b)在20℃与100℃之间的温度下在有机溶剂如甲醇中用具有式(III-b)的原酸酯(其中R6是C1-C4烷基)处理,接着用具有式(III-c)的胺(其中R1和R2是如针对式(I)所定义)处理。
c)在-20℃与40℃之间的温度下在惰性溶剂如二氯甲烷中用具有式(III-d)的甲酰胺(其中R1和R2是如针对式(I)所定义)和活化剂如POCl3处理
这在下面的方案10中示出。
方案10
具有式(XV)的化合物(其中R3是如针对式(I)所定义的并且R7是卤素,优选溴或碘)可以通过用卤化剂(如溴、N-溴代琥珀酰亚胺或N-碘代琥珀酰亚胺)转化具有式(XVI)的化合物(其中R3是如针对式(I)所定义的)来获得。这在下面的方案11中示出。
方案11
具有式(XVI)的化合物(其中R3是如针对式(I)所定义的)可以通过在还原条件下(例如通过催化氢化)或在贝尚(Bechamp)反应的条件下转化具有式(XVII)的化合物(其中R3是如针对式(I)所定义的)来获得。这在下面的方案12中示出。
方案12
具有式(XVII)的化合物(其中R3是如针对式(I)所定义的)可以通过用甲基溴或甲基碘和碱(如氢化钠或碳酸钾)转化具有式(XVIII)的化合物(其中R3是如针对式(I)所定义的)来获得。这在下面的方案13中示出。
方案13
以上方案中所述的某些中间体是新颖的并且如此形成本发明的另一个方面。
具有式(I)的这些化合物可以例如作为活性成分用于农业部门和相关领域,来控制植物有害生物或用于非生物材料上来控制腐败微生物或潜在地对人类有害的生物。这些新颖化合物的特色是在低施用率下具有优异的活性,植物耐受良好以及不危害环境。它们具有非常有用的治疗、预防和系统特性,并且可以用于保护许多栽培植物。具有式(I)的化合物可以用于抑制或破坏在多种不同的有用植物作物的植物或植物部分(果实、花、叶子、茎、块茎、根)上出现的有害生物,同时还保护了例如稍后生长的那些植物部分免于植物病原性微生物的侵害。
还可能使用具有式(I)的化合物作为杀真菌剂。如本文使用的,术语“杀真菌剂”意指控制、改变或防止真菌生长的化合物。术语“杀真菌有效量”意指能够对真菌生长产生影响的这样一种化合物或这样的化合物的组合的量。控制或修饰的影响包括所有从自然发育的偏离,如杀死、阻滞等,并且防止包括在植物内或上面防止真菌感染的屏障或其他防御构造。
还有可能使用具有式(I)的化合物作为用于处理植物繁殖材料,例如种子(例如果实、块茎或谷粒)或植物插条(例如稻)的拌种剂(dressing agent),用于保护对抗真菌侵染连同对抗在土壤中存在的植物病原性真菌。可以在种植以前用包含具有式(I)的化合物的组合物处理繁殖材料:例如可以在播种前拌种。还可以通过在液体配制品中浸渍种子或通过用固体配制品包衣它们,从而将具有式(I)的化合物施用至谷物(包衣)。还可以在种植繁殖材料时,将组合物施用至种植位点,例如在播种期间施用至种子的犁沟。本发明还涉及处理植物繁殖材料的这样的方法,并且涉及如此处理的植物繁殖材料。
此外,根据本发明的化合物可以用于控制相关领域的真菌,这些领域是例如在工业材料(包括木材以及与木材有关的工业产品)的保护中、在食品存储中、在卫生管理中。
此外,本发明还可以用于保护非生命材料(例如木料、墙板和涂料)免受真菌攻击。
具有式(I)的化合物和含有它们的杀真菌组合物可以用于控制由广泛的真菌植物病原体引起的植物疾病。它们有效地控制广泛的植物疾病,如观赏植物、草皮、蔬菜、大田、谷类、以及水果作物的叶病原体。
可以被控制的疾病的这些真菌和真菌载体连同植物病原性细菌和病毒是例如:
伞枝梨头霉、链格孢属物种、丝囊霉属物种、壳二孢属物种、曲霉属物种(包括黄曲霉、烟曲霉、构巢曲霉、黑曲霉、土曲霉)、短梗霉属物种(包括出芽短梗霉(A.pullulans))、皮炎芽生菌、小麦白粉病菌、莴苣盘梗霉(Bremia lactucae)、葡萄座腔菌属物种(包括葡萄溃疡病菌(B.dothidea)、树花地衣葡萄座腔菌(B.obtusa))、葡萄孢属物种(包括灰葡萄孢(B.cinerea))、假丝酵母属物种(包括白色念珠菌、光滑球念珠菌(C.glabrata)、克鲁斯念珠菌(C.krusei)、萄牙念珠菌(C.lusitaniae)、近平滑念珠菌(C.parapsilosis)、热带念珠菌(C.tropicalis))、Cephaloascus fragrans、长喙壳属物种、尾孢属物种(包括褐斑病菌(C.arachidicola))、晚斑病菌(Cercosporidium personatum)、枝孢霉属物种、麦角菌、
粗球孢子菌、旋孢腔菌属物种、炭疽菌属物种(包括香蕉炭疽病菌(C.musae))、
新型隐球菌、间座壳属物种(Diaporthe spp)、亚隔孢壳属物种、内脐蠕孢属物种、痂囊腔菌属物种、
表皮癣菌属物种、梨火疫病菌、白粉菌属物种(包括菊科白粉菌(E.cichoracearum))、
葡萄顶枯病菌(Eutypa lata)、镰刀菌属物种(包括大刀镰刀菌、禾谷镰刀菌、F.镰刀菌、串珠镰刀菌、胶孢镰刀菌、茄病镰刀菌、尖孢镰刀菌、层出镰刀菌)、小麦全蚀病菌(Gaeumannomyces graminis)、藤仓赤霉菌(Gibberella fujikuroi)、煤烟病菌(Gloeodespomigena)、香蕉炭疽盘长孢菌(Gloeosporium mmusarum)、苹果炭疽病菌(Glomerellacingulate)、葡萄球座菌(Guignardia bidwellii)、植物受桧胶锈菌(Gymnosporangiumjuniperi-virginianae)、长蠕孢属物种、驼孢锈菌属物种、组织胞浆菌属物种(包括荚膜组织胞浆菌(H.capsulatum))、红线病菌、Leptographium lindbergi、辣椒白粉病菌(Leveillula taurica)、松针散盘壳(Lophodermium seditiosum)、雪霉叶枯菌(Microdochium nivale)、小孢子菌属物种、链核盘菌属物种、毛霉属物种、球腔菌属物种(包括禾生球腔菌、苹果黑点病菌(M.Pomi))、树梢枯病菌、云杉病菌、副球孢子菌属物种、青霉属物种(包括指状青霉、意大利青霉)、霉样真霉属物种、指霜霉属物种(包括玉蜀黍指霜霉、菲律宾霜指霉和高粱指霜霉)、霜霉属物种、颖枯壳针孢、豆薯层锈菌、桑黄火木针层孔菌(Phellinu igniarus)、瓶霉蚁属物种、茎点霉属物种、葡萄生拟茎点菌(Phomopsisviticola)、疫霉菌属物种(包括致病疫霉菌)、单轴霉属物种(包括霍尔斯单轴霉菌、葡萄霜霉病菌(P.viticola))、格孢腔菌属物种、叉丝单囊壳属物种(包括白叉丝单囊壳(P.leucotricha))、禾谷多粘菌(Polymyxa graminis)、甜菜多粘菌(Polymyxa betae)、小麦基腐病菌(Pseudocercosporella herpotrichoides)、假单胞菌属物种、假霜霉属物种(包括黄瓜霜霉病菌、葎草假霜霉)、Pseudopeziza tracheiphila、霜霉属物种(包括大麦柄锈菌(P.hordei)、小麦叶锈病菌(P.recondita)、条形柄锈菌(P.Striiformis)、小麦褐锈菌(P.triticina))、埋核盘菌属物种、核腔菌属物种、梨孢属物种(包括稻瘟病菌(P.oryzae))、腐霉属物种(包括终极腐霉菌)、柱隔孢属物种、丝核菌属物种、微小根毛霉(Rhizomucor pusillus)、少根根霉、喙孢属物种、丝孢菌属物种(包括尖端赛多孢子菌和多育赛多孢子菌)、煤点病(Schizothyrium pomi)、
核盘菌属物种、小核菌属物种、壳针孢属物种(包括颖枯壳针孢(S.nodorum)、小麦壳针孢(S.tritici))、草莓白粉病菌(Sphaerotheca macularis)、棕丝单囊壳(Sphaerotheca fusca)(黄瓜白粉病菌(Sphaerotheca fuliginea))、孢子丝菌属物种(Sporothorix)、颖枯壳多孢(Stagonospora nodorum)、匍柄霉属物种(Stemphylium)、毛韧革菌(Stereum hirsutum)、水稻枯纹病菌(Thanatephorus cucumeris)、根串珠霉(Thielaviopsis basicola)、腥黑粉菌属物种、木霉属物种(包括哈茨木霉、拟康氏木霉、绿色木霉)、
毛癣菌属物种、核瑚菌属物种、葡萄钩丝壳、条黑粉菌属物种(Urocystis)、黑粉菌属物种(Ustilago)、黑星菌属物种(包括苹果黑星菌(V.inaequalis))、轮枝孢属物种以及黄单胞菌属物种。
具体地,具有式(I)的化合物和含有它们的杀真菌组合物可以用于控制由担子菌纲、子嚢菌纲、卵菌纲和/或半知菌纲、Blasocladiomycete、壶菌纲、球囊菌纲(Glomeromycete)和/或粒毛盘菌纲(Mucoromycete)中的广谱的真菌植物病原体引起的植物疾病。
这些病原体可以包括:
卵菌纲,包括疫霉病,如由辣椒疫霉菌、致病疫霉菌、大豆疫霉菌、草莓疫莓菌(Phytophthora fragariae)、烟草疫霉菌(Phytophthora nicotianae)、樟疫霉(Phytophthora cinnamomi)、柑橘生疫霉(Phytophthora citricola)、柑橘褐腐疫霉(Phytophthora citrophthora)和马铃薯绯腐病菌(Phytophthora erythroseptica)引起的那些;腐霉病,例如由瓜果腐霉菌、强雄腐霉菌(Pythium arrhenomanes)、禾生腐霉菌、畸雌腐霉菌(Pythium irregulare)和终极腐霉菌引起的那些;由霜霉目如大葱霜霉菌(Peronospora destructor)、白菜霜霉菌、葡萄霜霉菌、向日葵霜霉菌、黄瓜霜霉菌、白锈菌(Albugo Candida)、水稻霜霉病和莴苣霜霉菌引起的疾病;以及其他,例如螺壳状丝囊霉、Labyrinthula zosterae、高梁霜指霉(Peronosclerospora sorghi)和禾生指梗霉(Sclerospora graminicola)。
子囊菌纲,包括斑纹病、斑点病、瘟病或疫病和/或腐病,例如由如下引起的那些:格孢菌目如大蒜白斑病菌(Stemphylium solani)、Stagonospora tainanensis、油橄榄环梗孢菌、玉米大斑病菌(Setosphaeria turcica)、Pyrenochaeta lycoperisici、枯叶格孢腔菌、实腐茎点霉(Phoma destructiva)、Phaeosphaeria herpotrichoides、Phaeocryptocus gaeumannii、Ophiosphaerella graminicola、小麦全蚀病(Ophiobolusgraminis)、十字花科小球腔菌(Leptosphaeria maculans)、软腐病菌(Hendersoniacreberrima)、壳针孢叶枯病菌(Helminthosporium triticirepentis)、玉米大斑病菌(Setosphaeria turcica)、大豆内脐蠕孢(Drechslera glycines)、西瓜蔓枯病菌(Didymella bryoniae)、油橄榄孔雀斑病菌(Cycloconium oleagineum)、多主棒孢菌、禾旋孢腔菌、火龙果黑斑病菌(Bipolaris cactivora)、苹果黑星病菌、圆核腔菌、燕麦草核腔菌(Pyrenophora tritici-repentis)、互隔链格孢菌、芸苔链格孢菌(Alternariabrassicicola)、茄链格孢菌和西红柿链格孢菌(Alternaria tomatophila);煤炱目(Capnodiales)如小麦壳针孢、颖枯壳针孢、大豆壳针孢(Septoria glycines)、落花生尾孢菌(Cercospora arachidicola)、大豆灰斑病菌、玉米灰斑病菌、荠白斑病菌(Cercosporella capsellae)以及麦叶白霉(Cercosporella herpotrichoides)、桃疮痂病菌(Cladosporium carpophilum)、散生枝孢(Cladosporium effusum)、褐孢霉(Passalorafulva)、尖孢枝孢(Cladosporium oxysporum)、Dothistroma septosporum、葡萄褐斑病菌(Isariopsis clavispora)、香蕉黑条叶斑病菌、禾生球腔菌(Mycosphaerellagraminicola)、散梗菌绒孢菌(Mycovellosiella koepkeii)、Phaeoisariopsisbataticola、葡萄褐斑病菌(Pseudocercospora vitis)、小麦基腐病菌、甜菜叶斑病菌、柱隔孢叶斑病菌(Ramularia collo-cygni);粪壳菌目如小麦全蚀病菌、稻瘟病菌(Magnaporthe grisea)、稻梨孢、间座壳目如榛子东部枯萎病菌、Apiognomoniaerrabunda、Cytospora platani、大豆北方茎溃疡病菌、毁灭性座盘孢(Disculadestructiva)、草莓日规壳菌(Gnomonia fructicola)、葡萄苦腐病菌、核桃黑盘壳菌(Melanconium juglandinum)、葡萄生拟茎点菌(Phomopsis viticola)、胡桃溃疡病菌(Sirococcus clavigignenti-juglandacearum)、干孢盾壳椿启介菌(Tubakia dryina)、Dicarpella spp.、苹果树腐烂病菌(Valsa ceratosperma);以及其他,如Actinothyriumgraminis、豌豆壳二孢、黄曲霉、烟曲霉菌、构巢曲霉、番木瓜座糙孢菌、叶斑病菌(Blumeriella jaapii)、假丝酵母属、煤炱病菌(Capnodium ramosum)、Cephaloascusspp.、麦类条斑病菌(Cephalosporium gramineum)、奇异长喙壳(Ceratocystisparadoxa)、毛壳菌属、拟白膜盘菌(Hymenoscyphus pseudoalbidus)、球孢子菌属、李属柱孢霉(Cylindrosporium padi)、双壳菌(Diplocarpon malae)、Drepanopezizacampestris、痂囊腔菌(Elsinoe ampelina)、黑附球菌、表皮癣菌属、葡萄顶枯病、白地霉、禾谷绒座壳(Gibellina cerealis)、高粱胶尾孢(Gloeocercospora sorghi)、煤烟病菌(Gloeodes pomigena)、Gloeosporium perennans;毒麦内生真菌(Gloeotiniatemulenta)、Griphospaeria corticola、利尼球梗孢(Kabatiella lini)、小孢粘束孢(Leptographium microsporum)、Leptosphaerulinia crassiasca、Lophodermiumseditiosum、禾谷盘二孢菌(Marssonina graminicola)、雪霉叶枯菌、美澳型核果褐腐病菌、稻云形病(Monographella albescens)、甜瓜黑点根腐病菌、丝环盘菌属(Naemacyclusspp.)、新榆枯萎病菌、巴西副球孢子菌、扩展青霉、杜鹃盘多毛孢霉(Pestalotiarhododendri)、霉样真霉属(Petriellidium)、无柄盘菌属、大豆茎褐腐病菌、Phyllachorapomigena、杂食动物瘤梗孢(Phymatotrichum omnivora)、隐秘囊孢菌(Physalosporaabdita)、烟草囊孢壳(Plectosporium tabacinum)、马铃薯皮斑病菌、苜蓿假盘菌(Pseudopeziza medicaginis)、芸薹埋核盘菌(Pyrenopeziza brassicae)、高粱座枝孢(Ramulispora sorghi)、Rhabdocline pseudotsugae、大麦云纹病菌(Rhynchosporiumsecalis)、稻帚枝杆孢(Sacrocladium oryzae)、足放线病菌属(Scedosporium)、仁果裂盾菌、核盘菌、小核盘菌;小核菌属、雪腐病核瑚菌(Typhula ishikariensis)、玛丽盘双端毛孢(Seimatosporium mariae)、Lepteutypa cupressi、Septocyta ruborum、Sphacelomaperseae、Sporonema phacidioides、千年枣眼点病菌(Stigmina palmivora)、Tapesiayallundae、梨外囊菌(Taphrina bullata)、棉花黑根腐病菌(Thielviopsis basicola)、Trichoseptoria fructigena、蝇粪病菌(Zygophiala jamaicensis);白粉病,例如由白粉菌目如小麦白粉病菌、蓼白粉病菌、葡萄钩丝壳、黄瓜白粉病菌(Sphaerotheca fuligena)、白叉丝单囊壳、Podospaera macularis、二孢白粉菌(Golovinomyces cichoracearum)、鞑靼内丝白粉菌(Leveillula taurica)、扩散叉丝壳、Oidiopsis gossypii、榛球针壳(Phyllactinia guttata)以及Oidium arachidis引起的那些;霉,例如由葡萄座腔菌如小穴壳菌(Dothiorella aromatica)、连续色二孢(Diplodia seriata)、比德瓦里球座菌(Guignardia bidwellii)、灰霉菌(Botrytis cinerea)、大葱孢盘菌(Botryotiniaallii)、蚕豆孢盘菌(Botryotinia fabae)、扁桃壳梭菌(Fusicoccum amygdali)、龙眼焦腐病菌(Lasiodiplodia theobromae)、茶生大茎点霉(Macrophoma theicola)、菜豆壳球孢菌、葫芦科叶点霉(Phyllosticta cucurbitacearum)引起的那些;炭疽病,例如由小丛壳(Glommerelales)如盘长孢状刺盘孢、瓜类炭疽菌、棉花炭疽病菌、围小丛壳、以及禾生炭疽菌引起的那些;以及枯萎病或疫病,例如由肉座菌目如笔直顶孢霉、紫麦角菌、黄色镰刀菌、禾谷镰刀菌、大豆猝死综合症病菌(Fusarium virguliforme)、尖孢镰刀菌、胶孢镰刀菌、古巴尖孢镰孢(Fusarium oxysporum f.sp.cubense)、Gerlachia nivale、藤仓赤霉、玉米赤霉、胶枝霉属物种、疣孢漆斑菌、Nectria ramulariae、绿色木霉、粉红聚端孢菌和鳄梨根腐病原菌(Verticillium theobromae)引起的那些。
担子菌纲,包括黑穗病,例如由黑粉菌目如稻曲病菌、小麦散黑穗病菌、小麦散黑粉菌菌、玉米黑粉病菌引起的那些,锈病例如由柄锈菌如Cerotelium fici、云杉帚锈病菌(Chrysomyxa arctostaphyli)、番薯鞘锈菌(Coleosporium ipomoeae)、咖啡驼孢锈菌(Hemileia vastatrix)、落花生柄锈菌、Puccinia cacabata、禾柄锈菌、隐匿柄锈菌、高粱柄锈菌、大麦柄锈菌、大麦条形柄锈菌(Puccinia striiformis f.sp.Hordei)、小麦条形柄锈菌(Puccinia striiformis f.sp.Secalis)、榛膨痂锈菌(Pucciniastrum coryli);或锈菌目如松疱锈病菌、美洲苹果锈病菌(Gymnosporangium juniperi-virginianae)、杨树叶锈病菌(Melampsora medusae)、豆薯层锈菌(Phakopsora pachyrhizi)、短尖多胞锈菌(Phragmidium mucronatum)、Physopella ampelosidis、变色疣双胞锈菌(Tranzscheliadiscolor)以及蚕豆单孢锈菌(Uromyces viciae-fabae)引起的那些;以及其他腐病和疾病,例如由隐球菌属物种、茶饼病菌、Marasmiellus inoderma、小菇属物种、丝黑穗病菌(Sphacelotheca reiliana)、雪腐病核瑚菌(Typhula ishikariensis)、冰草条黑粉菌(Urocystis agropyri)、Itersonilia perplexans、伏革菌(Corticium invisum)、地衣状伏革菌(Laetisaria fuciformis)、Waitea circinata、立枯丝核菌、Thanetephoruscucurmeris、大丽花叶黑粉菌(Entyloma dahliae)、Entylomella microspora、沼湿草尾孢黑粉菌(Neovossia moliniae)和小麦网腥黑穗病菌(Tilletia caries)引起的那些。
芽枝霉纲,如玉蜀黍节壶菌(Physoderma maydis)。
粒毛盘菌纲(Mucoromycete),如笋瓜花腐病菌(Choanephora cucurbitarum);毛霉属;少根根霉,
连同由与以上列出的那些紧密相关的其他物种和属引起的疾病。
除了它们的杀真菌活性之外,这些化合物和包含它们的组合物还可以具有针对细菌如梨火疫病菌、软腐欧文氏菌(Erwinia caratovora)、野油菜黄单胞菌、丁香假单胞菌、马铃薯疮痂病菌(Strptomyces scabies)和其他相关物种以及某些原生动物的活性。
在本发明的范围内,有待保护的目标作物和/或有用植物典型地包括多年生和一年生作物,如浆果植物,例如黑莓、蓝莓、蔓越莓、树莓以及草莓;谷类,例如大麦、玉蜀黍(玉米)、小米、燕麦、稻、黑麦、高粱、黑小麦和小麦;纤维植物,例如棉花、亚麻、大麻、黄麻和剑麻;大田作物,例如糖甜菜和饲料甜菜、咖啡豆、啤酒花、芥菜、油菜(卡诺拉)、罂粟、甘蔗、向日葵、茶以及烟草;果树,例如苹果、杏、鳄梨、香蕉、樱桃、柑橘、油桃、桃、梨以及李子;草,例如百慕达草、蓝草、本特草、蜈蚣草、牛毛草、黑麦草、圣奥古斯丁草以及结缕草;药草,例如罗勒、琉璃苣、细香葱、胡荽、薰衣草、独活草、薄荷、牛至、荷兰芹、迷迭香、鼠尾草以及百里香;豆类,例如菜豆、小扁豆、豌豆和大豆;坚果,例如杏仁、腰果、落花生、榛子、花生、山核桃、开心果和核桃;棕榈植物,例如油棕榈;观赏植物,例如花、灌木和树;其他树木,例如可可、椰子、橄榄和橡胶;蔬菜,例如芦笋、茄子、西兰花、卷心菜、胡萝卜、黄瓜、大蒜、莴苣、西葫芦、甜瓜、秋葵、洋葱、胡椒、马铃薯、南瓜、大黄、菠菜和番茄;和葡萄藤,例如葡萄。
根据本发明的有用植物和/或目标作物包括常规的连同遗传增强或遗传工程处理的品种,例如像抗虫的(例如Bt.和VIP品种)连同抗病的、耐除草剂的(例如耐草甘膦和草丁膦的玉米品种,在商品名和下可商购)以及耐受线虫的品种。通过举例的方式,适合的遗传增强或遗传工程处理的作物品种包括Stoneville 5599BR棉花和Stoneville 4892BR棉花品种。
术语“有用植物”和/或“目标作物”应当理解为还包括由于常规育种方法或基因工程方法而赋予了对除草剂(像溴草腈)或除草剂类的(例如像HPPD抑制剂、ALS抑制剂,如氟嘧磺隆、氟丙磺隆和三氟啶磺隆、EPSPS(5-烯醇-丙酮酰-莽草酸-3-磷酸-合酶(5-enol-pyrovyl-shikimate-3-phosphate-synthase))抑制剂、GS(谷氨酰胺合酶)抑制剂或PPO(原卟啉原氧化酶)抑制剂)的耐受性的有用植物。已经通过常规育种方法(诱变)致使对咪唑啉酮(例如甲氧咪草烟)耐受的作物的实例是夏季油菜(卡诺拉)。已经通过基因工程方法使其对除草剂或除草剂类耐受的作物的实例包括抗草甘膦和抗草丁膦玉蜀黍品种,它们是在Herculex和商标名下可商购的。
术语“有用植物”和/或“目标作物”应被理解为包括天然地或已经赋予对有害昆虫的抗性的那些。这包括通过使用重组DNA技术转化从而例如能够合成一种或多种选择性作用毒素的植物,这些毒素例如是从如产毒素的细菌已知的。可以被表达的毒素的实例包括δ-内毒素,营养期杀虫蛋白(Vip),细菌定殖线虫的杀虫蛋白,以及由蝎子、蛛形纲动物、黄蜂和真菌产生的毒素。已经被修饰为表达苏云金杆菌毒素的作物的实例是Bt maize(先正达种子公司(Syngenta Seeds))。包括编码杀昆虫抗性并且由此表达多于一种毒素的多于一种基因的作物的实例是(先正达种子公司)。作物或其种子材料还可以是对多种类型的有害生物具有抗性(当通过遗传修饰产生时的所谓的叠加转基因事件)。例如,植物可以具有表达杀昆虫蛋白而同时耐受除草剂的能力,例如Herculex(陶氏益农公司(Dow AgroSciences),先锋良种国际公司(Pioneer Hi-BredInternational))。
术语“有用植物”和/或“目标作物”可以理解为也包括已经通过使用重组DNA技术转换了的,以至于能够合成有选择性活性的抗致病性物质,例如,所谓的“致病机理相关的蛋白”(PRPs,见例EP-A-0 392 225)。这些抗病原物质和能够合成这些抗病原物质的转基因植物的实例是已知的,例如从EP-A-0 392 225、WO 95/33818以及EP-A-0 353 191得知的。生产此类转基因植物的方法对于本领域技术人员而言通常是已知的并且描述于例如以上提及的公开物中。
可由转基因植物表达的毒素包括例如,来自蜡样芽孢杆菌或日本金龟子芽孢杆菌的杀昆虫蛋白;或来自苏云金芽孢杆菌的杀昆虫蛋白,如δ-内毒素,例如Cry1Ab、Cry1Ac、Cry1F、Cry1Fa2、Cry2Ab、Cry3A、Cry3Bb1或Cry9C,或营养期杀昆虫蛋白(Vip),例如Vip1、Vip2、Vip3或Vip3A;或线虫寄生性细菌的杀昆虫蛋白,例如光杆状菌属物种或致病杆菌属物种,如发光杆状菌、嗜线虫致病杆菌;由动物产生的毒素,如蝎毒素、蜘蛛毒素、黄蜂毒素和其他昆虫特异性神经毒素;由真菌产生的毒素,如链霉菌毒素;植物凝集素,如豌豆凝集素、大麦凝集素或雪花莲凝集素;凝集素类;蛋白酶抑制剂,如胰蛋白酶抑制剂、丝氨酸蛋白酶抑制剂、马铃薯贮存蛋白(patatin)、半胱氨酸蛋白酶抑制剂、木瓜蛋白酶抑制剂;核糖体失活蛋白(RIP),如蓖麻蛋白、玉米-RIP、相思豆毒蛋白、丝瓜籽毒蛋白、皂草毒素蛋白或异株泻根毒蛋白;类固醇代谢酶,如3-羟基类固醇氧化酶、蜕化类固醇-UDP-糖基-转移酶、胆固醇氧化酶、蜕化素抑制剂、HMG-COA-还原酶、离子通道阻断剂如钠通道或钙通道阻断剂、保幼激素酯酶、利尿激素受体、芪合酶、联苄合酶、几丁质酶和葡聚糖酶。
进一步地,在本发明的背景下,δ-内毒素(例如Cry1Ab、Cry1Ac、Cry1F、Cry1Fa2、Cry2Ab、Cry3A、Cry3Bb1或Cry9C)或营养期杀虫蛋白(Vip)(例如Vip1、Vip2、Vip3或Vip3A)应理解为显然还包括混合型毒素、截短的毒素和经修饰的毒素。混合型毒素是通过那些蛋白的不同结构域的新组合重组产生的(参见例如,WO 02/15701)。截短的毒素,例如截短的Cry1Ab是已知的。在经修饰的毒素的情况下,天然存在的毒素的一个或多个氨基酸被置换。在这种氨基酸置换中,优选将非天然存在的蛋白酶识别序列插入毒素中,例如像在Cry3A055的情况下,一种组织蛋白酶-G-识别序列被插入Cry3A毒素中(参见WO 03/018810)。
这样的毒素或能够合成这样的毒素的转基因植物的更多实例披露于例如EP-A-0374 753、WO 93/07278、WO 95/34656、EP-A-0 427 529、EP-A-451 878以及WO 03/052073中。
用于制备这样的转基因植物的方法通常是本领域技术人员已知的并且描述在例如以上提及的公开物中。CryI型脱氧核糖核酸及其制备例如从WO 95/34656、EP-A-0 367474、EP-A-0 401 979和WO 90/13651中已知。
含有在转基因植物中的毒素使得植物对有害昆虫有耐受性。这样的昆虫可以存在于任何昆虫分类群,但尤其常见于甲虫(鞘翅目)、双翅昆虫(双翅目)和蛾(鳞翅目)。
含有一种或多种编码杀昆虫剂抗性并且表达一种或多种毒素的基因的转基因植物是已知的并且其中一些是可商购的。此类植物的实例是:(玉米品种,表达Cry1Ab毒素);YieldGard (玉米品种,表达Cry3Bb1毒素);YieldGard(玉米品种,表达Cry1Ab和Cry3Bb1毒素);(玉米品种,表达Cry9C毒素);Herculex(玉米品种,表达Cry1Fa2毒素和获得对除草剂草铵膦铵的耐受性的酶膦丝菌素N-乙酰基转移酶(PAT));NuCOTN(棉花品种,表达Cry1Ac毒素);Bollgard(棉花品种,表达Cry1Ac毒素);Bollgard(棉花品种,表达Cry1Ac和Cry2Ab毒素);(棉花品种,表达Vip3A和Cry1Ab毒素); (马铃薯品种,表达Cry3A毒素);GT Advantage(GA21耐草甘膦性状)、CB Advantage(Bt11玉米螟(CB)性状)以及
此类转基因作物的另外的实例是:
1.Bt11玉米,来自先正达种子公司(Syngenta Seeds SAS),霍比特路(Chemin del’Hobit)27,F-31 790圣苏维尔(St.Sauveur),法国,登记号C/FR/96/05/10。遗传修饰的玉蜀黍,通过转基因表达截短的Cry1Ab毒素,使之能抵抗欧洲玉米螟(玉米螟和粉茎螟)的侵袭。Bt11玉米还转基因表达PAT酶以获得对除草剂草铵膦铵盐的耐受性。
2.Bt176玉米,来自先正达种子公司,霍比特路27,F-31 790圣苏维尔,法国,登记号C/FR/96/05/10。遗传修饰的玉蜀黍,通过转基因表达Cry1Ab毒素,使之能抵抗欧洲玉米螟(玉米螟和粉茎螟)的侵袭。Bt176玉米还转基因表达酶PAT以获得对除草剂草铵膦铵盐的耐受性。
3.MIR604玉米,来自先正达种子公司,霍比特路27,F-31 790圣苏维尔,法国,登记号C/FR/96/05/10。通过转基因表达经修饰的Cry3A毒素使之具有昆虫抗性的玉米。此毒素是通过插入组织蛋白酶-G-蛋白酶识别序列而经修饰的Cry3A055。此类转基因玉米植物的制备描述于WO 03/018810中。
4.MON 863玉米,来自孟山都欧洲公司(Monsanto Europe S.A.),270-272特弗伦大道(Avenue de Tervuren),B-1150布鲁塞尔,比利时,登记号C/DE/02/9。MON 863表达Cry3Bb1毒素,并且对某些鞘翅目昆虫有抗性。
5.IPC 531棉花,来自孟山都欧洲公司,270-272特弗伦大道(Avenue deTervuren),B-1150布鲁塞尔,比利时,登记号C/ES/96/02。
6.1507玉米,来自先锋海外公司(Pioneer Overseas Corporation),特德斯科大道(Avenue Tedesco),7B-1160布鲁塞尔,比利时,登记号C/NL/00/10。遗传修饰的玉米,表达蛋白质Cry1F以获得对某些鳞翅目昆虫的抗性,并且表达PAT蛋白质以获得对除草剂草丁膦铵的耐受性。
7.NK603×MON 810玉米,来自孟山都欧洲公司270-272特弗伦大道,B-1150布鲁塞尔,比利时,登记号C/GB/02/M3/03。通过将遗传修饰的品种NK603和MON 810杂交,由常规育种的杂交玉米品种构成。NK603×MON 810玉米转基因地表达由土壤杆菌属菌株CP4获得的蛋白质CP4 EPSPS(使之耐除草剂(含有草甘膦)),以及还有由苏云金芽孢杆菌库尔斯塔克亚种(Bacillus thuringiensis subsp.kurstaki)获得的Cry1Ab毒素(使之耐某些鳞翅目昆虫,包括欧洲玉米螟)。
如本文使用的,术语“场所”意指植物在其中或其上生长的地方,或栽培植物的种子被播种的地方,或者种子将要被置于土壤中的地方。它包括土壤、种子以及幼苗,连同建立的植被。
术语“植物”是指植物的所有有形部分,包括种子、幼苗、幼树、根、块茎、茎、秆、叶和果实。
术语“植物繁殖材料”应当理解为表示植物的生殖部分,如种子,所述部分可以用于植物的繁殖,以及营养性材料,如插条或块茎(例如马铃薯)。可以提及例如种子(在严格意义上)、根、果实、块茎、球茎、根茎以及植物的部分。还可以提及在发芽后或破土后将被移植的发芽植物和幼小植物。这些幼小植物可以通过浸渍进行完全或部分处理而在移植之前进行保护。优选地,“植物繁殖材料”应当理解为表示种子。
本文提及的使用其俗名的杀有害生物剂是已知的,例如,从“The PesticideManual[杀有害生物剂手册]”,第15版,英国作物保护委员会(British Crop ProtectionCouncil)2009。
具有式(I)的化合物能以未修饰的形式使用,或者优选地,连同配制品领域中常规使用的辅助剂一起使用。为此目的,它们可以按已知方式便利地配制为可乳化浓缩物、可包衣的糊剂、直接可喷雾的或可稀释的溶液或悬浮液、稀释乳液、可湿性粉剂、可溶性粉剂、尘剂、颗粒以及还有封装物,例如在聚合物的物质中。对于组合物的类型,根据预期的目的以及盛行环境来选择施用方法,如喷雾、雾化、撒粉、播散、包衣或倾倒。这些组合物还可以含有另外的辅助剂,如稳定剂、消泡剂、粘度调节剂、粘合剂或增粘剂,以及肥料、微量营养素供体或其他用于获得特殊效果的配制品。
合适的载体以及辅助剂,例如对于农业用途,可以是固体或液体的并且是在配制品技术中有用的物质,例如天然或再生的矿物物质,溶剂、分散体、湿润剂、增粘剂、增稠剂、粘合剂或肥料类。这样的载体例如描述在WO 97/33890中。
悬浮液浓缩物是活性化合物的高度分散的固体颗粒悬浮于其中的水性配制品。此类配制品包括抗沉降剂和分散剂,并且可以进一步包括湿润剂以增强活性,以及消泡剂和晶体生长抑制剂。在使用时,将这些浓缩物稀释在水中,并且通常作为喷雾剂施用至有待处理的区域。活性成分的量的范围可以是从所述浓缩物的0.5%到95%。
可湿性粉剂是处于在水中或其他液态载体中容易分散的高度分散的颗粒形式。这些颗粒含有保存在固体基质里的活性成分。典型的固体基质包括漂白土、高岭土、硅石和其他容易湿化的有机或无机固体。可湿性粉剂通常包含从5%到95%的活性成分加上少量的润湿剂、分散剂或乳化剂。
可乳化的浓缩物是在水中或其他液体中可分散的均匀的液体组合物并且可以完全由活性化合物与液体或固体乳化剂组成,或者还可以含有液态载体,如二甲苯、重芳族石脑油、异佛尔酮和其他不挥发有机溶剂。在使用时,将这些浓缩物分散在水中或其他液体中,并且通常作为喷雾剂施用至有待处理的区域。活性成分的量的范围可以是从所述浓缩物的0.5%到95%。
颗粒配制品包括挤出物和较粗颗粒两者,并且通常不用稀释地施用至需要处理的区域。用于颗粒配制品的典型载体包括沙、漂白土、凹凸棒石粘土、膨润土、蒙脱土、蛭石、珍珠岩、碳酸钙、砖、浮石、叶蜡石、高岭土、白云石、灰泥、木粉、碎玉米穗轴、碎花生壳、糖、氯化钠、硫酸钠、硅酸钠、硼酸钠、氧化镁、云母、氧化铁、氧化锌、氧化钛、氧化锑、冰晶石、石膏、硅藻土、硫酸钙以及其他有机或无机的吸收活性化合物或被活性化合物包衣的材料。颗粒配制品通常含有5%至25%的活性组分,这些成分可包括表面活性剂例如重芳烃挥发油、煤油和其他石油馏分,或植物油;和/或粘着剂如糊精、胶或合成树脂。
尘粉剂是活性成分与高度分散的固体(例如滑石、粘土、面粉以及其他有机与无机的作为分散剂和载体的固体)的可自由流动的混合物。
微囊典型地是包裹在惰性多孔壳内的活性成分的微滴或颗粒,所述惰性多孔壳允许以可控的速率让包住的材料逃逸到环境中。包囊的微滴的直径典型地为1微米到50微米。包裹的液体典型地构成胶囊重量的50%至95%并且除了活性化合物外还可以包括溶剂。包囊的颗粒通常是多孔颗粒,其中多孔膜将颗粒孔口密封,从而将活性种类以液体形式保存在颗粒孔内部。颗粒的直径的范围典型地是从1毫米至1厘米并且优选地1毫米至2毫米。颗粒通过挤出、凝聚或成球形成,或者是天然存在的。这样的材料的实例为蛭石、烧结粘土、高岭土、凹凸棒石粘土、锯屑和碳精粒。壳或膜材料包括天然和合成橡胶、纤维材料、苯乙烯-丁二烯共聚物、聚丙烯腈、聚丙烯酸酯、聚酯、聚酰胺、聚脲、聚氨酯和淀粉黄原酸酯。
用于农用化学应用的其他有用配制品包括活性成分在溶剂(例如丙酮、烷基化萘、二甲苯和其他有机溶剂)中的简单溶液,在所述溶剂中活性成分以所希望的浓度完全溶解。也可以使用加压的喷雾剂,其中由于低沸点分散剂溶剂载体的蒸发活性成分以高度分散的形式分散。
在上述配制品类型中对于配制本发明的组合物有用的合适的农用辅助剂和载体是本领域的普通技术人员熟知的。
可以利用的液态载体包括例如水、甲苯、二甲苯、石脑油、作物油、丙酮、甲基乙基酮、环己酮、乙酸酐、乙腈、乙酰苯、乙酸戊酯、2-丁酮、氯苯、环己烷、环己醇、乙酸烷基酯、二丙酮醇、1,2-二氯丙烷、二乙醇胺、对-二乙基苯、二甘醇、松香酸二甘醇酯、二甘醇丁醚、二甘醇乙醚、二甘醇甲醚、N,N-二甲基甲酰胺、二甲基亚砜、1,4-二噁烷、二丙二醇、二丙二醇甲醚、二丙二醇二苯甲酸酯、二丙二醇(diproxitol)、烷基吡咯烷酮、乙酸乙酯、2-乙基己醇、碳酸亚乙酯、1,1,1-三氯乙烷、2-庚酮、α-蒎烯、d-苧烯、乙二醇、乙二醇丁醚、乙二醇甲醚、γ-丁内酯、甘油、甘油二乙酸酯、甘油一乙酸酯、甘油三乙酸酯、十六烷、己二醇、乙酸异戊酯、乙酸异冰片酯、异辛烷、异佛尔酮、异丙苯、肉豆蔻酸异丙酯、乳酸、月桂胺、异丙叉丙酮、甲氧基丙醇、甲基异戊酮、甲基异丁基酮、月桂酸甲酯、辛酸甲酯、油酸甲酯、二氯甲烷、间二甲苯、正己烷、正辛胺、十八酸、乙酸辛胺酯、油酸、油胺、邻二甲苯、苯酚、聚乙二醇(PEG400)、丙酸、丙二醇、丙二醇单甲醚、对二甲苯、甲苯、磷酸三乙酯、三甘醇、二甲苯磺酸、石蜡、矿物油、三氯乙烯、全氯乙烯、乙酸乙酯、乙酸戊酯、乙酸丁酯、甲醇、乙醇、异丙醇、以及更高分子量的醇类如戊醇、四氢糠醇、己醇、辛醇等,乙二醇、丙二醇、甘油以及N-甲基-2-吡咯烷酮。水通常是用以稀释浓缩物的选用载体。
合适的固体载体包括例如滑石、二氧化钛、叶腊石粘土、硅石、凹凸棒石粘土、硅藻土(kieselguhr)、白垩、硅藻土(diatomaxeous earth)、石灰、碳酸钙、膨润土、漂白土、棉子壳、小麦粉、大豆粉、浮石、木粉、核桃壳粉以及木质素。
在所述液体和固体组合物中可有利地采用广泛的表面活性剂,尤其是被设计为可在施用前用载体稀释的那些。这些试剂在使用时通常按重量计组成配制品的从0.1%到15%。它们在性质上可以是阴离子的、阳离子的、非离子的或聚合的并且可以作为乳化剂、润湿剂、悬浮剂或以其他目的采用。典型的表面活性剂包括烷基硫酸盐如月桂基硫酸二乙醇铵;烷基芳基磺酸盐,如十二烷基苯磺酸钙;烷基酚/氧化烯加成产物,如壬基苯酚-C.sub.18乙氧基化物;醇-氧化烯加成产物,如十三烷醇-C.sub.16乙氧基化物;皂,如硬脂酸钠;烷基萘磺酸盐,如二丁基萘磺酸钠;磺基琥珀酸二烷基酯的盐,如二(2-乙基己基)磺基琥珀酸钠;山梨糖醇酯,如山梨糖醇油酸酯;季胺类,如月桂基三甲基氯化铵;脂肪酸的聚氧乙烯酯,如聚乙二醇硬脂酸酯;环氧乙烷和环氧丙烷的嵌段共聚物;以及磷酸单和二烷基酯的盐。
通常在农业组合物中使用的其他辅助剂包括结晶作用抑制剂、粘度调节剂、悬浮剂、喷雾液滴改性剂、颜料、抗氧化剂、发泡剂、防泡剂、遮光剂、相容性试剂、消泡剂、掩蔽剂、中和剂和缓冲剂、腐蚀抑制剂、染料、增味剂、铺展剂、渗透助剂、微量营养素、柔润剂、润滑剂以及固着剂。
此外,进一步地,其他杀生物的活性成分或组合物可以与本发明的组合物组合,并且用于本发明的方法中并且同时地或顺序地随着本发明的组合物施用。当同时施用时,这些另外的活性成分可以连同本发明的组合物一起配制或混合于例如喷雾罐中。这些另外的杀生物的活性成分可以是杀真菌剂、除草剂、杀昆虫剂、杀细菌剂、杀螨剂、杀线虫剂和/或植物生长调节剂。
此外,本发明的组合物还可以与一种或多种系统获得性抗性诱导剂(“SAR”诱导剂)一起施用。SAR诱导剂是已知的并且描述于例如美国专利号US 6,919,298中,并且包括例如水杨酸盐以及商用的SAR诱导剂阿拉酸式苯-S-甲基。
具有式(I)的化合物通常以组合物的形式使用并且可同时地或与另外的化合物顺序地施用于作物区域或有待处理的植物。例如,这些另外的化合物可以是影响植物生长的肥料或微量营养素供体或其他制剂。它们还可以是选择性除草剂或非选择性除草剂,连同杀昆虫剂、杀真菌剂、杀细菌剂、杀线虫剂、杀软体动物剂或几种这些制剂的混合物,如果希望的话连同配制品领域中通常使用的另外的载体、表面活性剂或促进施用的辅助剂一起。
具有式(I)的这些化合物可以按控制或保护抵抗植物病原性微生物的(杀真菌的)组合物的形式使用,这些组合物包含至少一种具有式(I)的化合物或至少一种优选的如上所定义的个别化合物作为活性成分(处于游离形式或以农业上可用的盐形式),并且包含至少一种上述辅助剂。
因此,本发明提供了如下组合物,优选地是杀真菌组合物,其包含至少一种具有式(I)的化合物、农业上可接受的载体以及任选地辅助剂。农业上可接受的载体是例如适合农业用途的载体。农业载体在本领域是熟知的。优选地,除了包含具有式(I)的化合物,所述组合物可以包含至少一种或多种杀有害生物活性化合物,例如另外的杀真菌活性成分。
具有式(I)的化合物可以是组合物的唯一活性成分,或者适当时它可以与一种或多种另外的活性成分(如杀有害生物剂、杀真菌剂、增效剂、除草剂或植物生长调节剂)混合。在一些情况下,另外的活性成分会导致出人意料的协同活性。
合适的另外的活性成分的实例包括以下项:1,2,4-噻二唑、2,6-二硝基苯胺、酰基丙氨酸、脂族含氮化合物、脒、氨基嘧啶醇、苯胺、苯胺-嘧啶类、蒽醌类、抗生素、芳基-苯基酮、苯甲酰胺、苯-磺酰胺、苯并咪唑、苯并噻唑、苯并硫代二唑(benzothiodiazole)、苯并噻吩、苯并吡啶、苯并噻二唑(benzthiadiazole)、苄基氨基甲酸酯、丁胺、氨基甲酸酯、甲酰胺、环丙酰菌胺(carpropamid)、氯腈(chloronitrile)、肉桂酸酰胺、含铜化合物、氰基乙酰胺、氰基丙烯酸酯、氰基咪唑、氰基亚甲基-噻唑烷、二腈(dicarbonitrile)、二羧酰胺、二甲酰亚胺、二甲基氨基磺酸盐、二硝基苯酚碳酸盐、二硝基苯酚、二硝基苯基巴豆酸酯、二苯基磷酸酯、二噻烯化合物、二硫代氨基甲酸酯、二硫醚、二硫戊环、乙基-氨基-噻唑甲酰胺、乙基-膦酸酯、呋喃甲酰胺、吡喃葡萄糖基、葡萄糖醛酸基、戊二腈、胍、除草剂/植物生长调节剂、己吡喃糖基抗生素、羟基(2-氨基)嘧啶、羟基苯胺、羟基异噁唑、咪唑、咪唑啉酮、杀虫剂/植物生长调节剂、异苯并呋喃酮、异噁唑烷基-吡啶、异噁唑啉、马来酰亚胺、扁桃酸酰胺、果胶衍生物、吗啉、去甲吗啉、N-苯基氨基甲酸酯、有机锡化合物、氧硫杂环己烷甲酰胺、噁唑、噁唑烷二酮、苯酚、苯氧基喹啉、苯基-乙酰胺、苯基酰胺、苯基苯甲酰胺、苯基-氧代-乙基-噻吩酰胺、苯基吡咯、苯基脲、硫代磷酸酯、磷酸、邻苯二甲酸、邻苯二甲酰亚胺、吡啶酰胺、哌嗪、哌啶、植物提取物、多氧霉素、丙酰胺、邻苯二甲酰亚胺、吡唑-4-甲酰胺、吡唑啉酮、哒嗪酮、吡啶、吡啶甲酰胺、吡啶基-乙基苯甲酰胺、嘧啶胺、嘧啶、嘧啶-胺、嘧啶酮-腙、吡咯烷、吡咯喹啉、喹唑啉酮、喹啉、喹啉衍生物、喹啉-7-甲酸、喹喔啉、螺缩酮胺、嗜球果伞素、氨磺酰三唑、磺酰胺、四唑肟、噻二嗪、噻二唑甲酰胺、噻唑羧酰胺、硫氰酸酯、噻吩羧酰胺、甲苯酰胺、三唑苯并噻唑、三唑、三唑-硫酮、三唑-嘧啶胺、缬氨酰胺氨基甲酸酯、甲基膦酸铵、含砷化合物、苯并咪唑基氨基甲酸酯、羰腈、羧酰苯胺、甲酰胺酰胺、羧基苯酰胺、二苯基吡啶、呋喃酰苯胺、肼甲酰胺、咪唑啉乙酸酯、间苯二甲酸酯、异噁唑酮、汞盐、有机汞化合物、有机磷酸酯、噁唑烷二酮、戊基磺酰基苯、苯基苯甲酰胺、硫代膦酸酯、硫代磷酸酯、吡啶甲酰胺、吡啶基糠基醚、吡啶基甲基醚、SDHI、噻二嗪硫酮、噻唑烷。
本发明的另一方面涉及控制或防止植物(例如有用植物(例如作物))、它们的繁殖材料(例如种子)、收获的作物(例如收获的粮食作物)、或非生命材料免于被植物病原性或腐败微生物或对人潜在有害的有机体(尤其是真菌有机体)侵染的方法,所述方法包括将具有式(I)的化合物或优选的如以上定义的单独的化合物作为活性成分施用至这些植物、植物的各部分或至其场所、它们的繁殖材料、或非生命材料的任何部分。
控制或防止是指将被昆虫或植物病原性微生物或腐败微生物或对人潜在有害的有机体(尤其是真菌有机体)的侵染减少至这样一个被证明改进的水平。
控制或预防作物植物被植物病原性微生物(尤其是真菌有机体)或昆虫侵染的优选的方法是叶面施用,所述方法包括施用具有式(I)的化合物、或含有至少一种所述化合物的农用化学组合物。施用频率和施用比率将取决于受相应的病原体或昆虫侵染的风险。然而,具有式(I)的化合物还可以通过用液体配制品浸泡所述植物的场所或者通过将处于固体形式的化合物例如以颗粒形式施用到土壤(土壤施用)而经由土壤通过根(内吸作用)渗透所述植物。在水稻作物中,可以将这样的颗粒施用到灌水的稻田中。具有式(I)的化合物还可以通过用杀真菌剂的液体配制品浸渍种子或块茎、或用固体配制品对其进行涂覆而施用到种子(包衣)上。
配制品(例如包含具有式(I)的化合物、以及(如果希望的话)固体或液体辅助剂或用于封装具有式(I)的化合物的单体的组合物)可以按已知方式进行制备,典型地通过将化合物与增充剂(例如溶剂、固体载体以及任选地表面活性化合物(表面活性剂))进行密切地混合和/或研磨。
这些组合物的施用方法,即控制上述类型的有害生物的方法,如喷雾、雾化、撒粉、刷涂、包衣、撒播或浇灌-它们被选择以适于普遍情况的预期目的-以及这些组合物用于控制上述类型的有害生物的用途是本发明的其他主题。典型的浓度比是在0.1与1000ppm之间、优选在0.1与500ppm之间的活性成分。每公项的施用量优选是每公项1g到2000g活性成分,更优选是10到1000g/ha,最优选是10到600g/ha。当作为种子浸泡试剂使用时,适宜的剂量是从10mg至1g活性物质/kg种子。
当本发明所述的组合用于处理种子时,比率为0.001至50g具有式(I)的化合物/kg种子、优选从0.01至10g/kg种子,这一般是足够的。
适当地,预防性(意指在疾病发展之前)或治愈性(意指疾病发展之后)施用根据本发明的具有式(I)的化合物的组合物。
本发明的组合物能以任何常规形式使用,例如,以双包装、干种子处理用的粉剂(DS)、种子处理用的乳液(ES)、种子处理用的可流动性浓缩物(FS)、种子处理用的溶液(LS)、种子处理用的水分散性粉剂(WS)、种子处理用的胶囊悬浮液(CF)、种子处理用的凝胶(GF)、乳液浓缩物(EC)、悬浮液浓缩物(SC)、悬浮乳液(SE)、胶囊悬浮液(CS)、水分散性颗粒(WG)、可乳化性颗粒(EG)、油包水型乳液(EO)、水包油型乳液(EW)、微乳液(ME)、分散性油悬剂(OD)、油悬剂(OF)、油溶性液剂(OL)、可溶性浓缩物(SL)、超低容量悬浮剂(SU)、超低容量液剂(UL)、母药(TK)、可分散性浓缩物(DC)、可湿性粉剂(WP)或与农业上可接受的辅助剂组合的任何技术上可行的配制品的形式。
能以常规方式生产这样的组合物,例如通过混合活性成分与适当的配制惰性剂(稀释剂、溶剂、填充剂及任选地其他配制成分,如表面活性剂、杀生物剂、防冻剂、粘着剂、增稠剂及提供辅佐效果的化合物)。还可以使用意欲长期持续药效的常规缓释配制品。特别得,待以喷雾形式,如水可分散性浓缩物(例如EC、SC、DC、OD、SE、EW、EO以及类似物)、可湿性粉剂及颗粒施用的配制品,可包含表面活性剂例如湿润剂和分散剂及提供辅佐效果的其他化合物,例如甲醛与萘磺酸盐、烷芳基磺酸盐、木质素磺酸盐、脂肪烷基硫酸盐及乙氧基化烷基酚和乙氧基化脂肪醇的缩合产物。
使用本发明的组合及稀释剂,以合适的拌种配制品形式,例如具有对种子的良好粘着性的水性悬浮液或干粉剂形式,用自身已知的方式将拌种配制品施用至种子。这样的拌种配制品在本领域是已知的。拌种配制品可以含有包囊形式的单一活性成分或活性成分的组合,例如作为缓释胶囊或微胶囊。
通常,配制品包括按重量计从0.01%至90%的活性成分,从0至20%的农业上可接受的表面活性剂及10%至99.99%的固体或液体配制惰性剂和一种或多种辅助剂,所述活性剂是由至少具有式(I)的化合物与组分(B)和(C)一起,以及任选地其他活性剂(特别是杀微生物剂或防腐剂或类似物)组成的。按重量计,组合物的浓缩形式通常含有在约2%与80%之间、优选在约5%与70%之间的活性剂。按重量计,配制品的施用形式可以例如含有从0.01%至20%、优选从0.01%至5%的活性剂。然而商用的产品将优选地被配制为浓缩物,最终使用者将通常使用稀释的配制品。
然而优选的是将商用的产品配制为浓缩物,最终使用者将通常使用稀释的配制品。
实例
接下来的实例用来阐明本发明。本发明的某些化合物与已知的化合物的区别可以在于在低施用率下更大的疗效,这可以由本领域的普通技术人员使用在实例中概述的实验程序,使用更低的施用率(如果必要的话)例如,50ppm、12.5ppm、6ppm、3ppm、1.5ppm、0.8ppm或0.2ppm来证实。
贯穿本说明书,以摄氏度给出温度并且“m.p.”意指熔点。LC/MS意指液相色谱法质谱法。
配制品实例
将所述活性成分与这些辅助剂充分混合并且将混合物在适合的研磨机中充分研磨,从而提供可以用水稀释而给出所希望的浓度的悬浮液的可湿性粉剂。
将所述活性成分与这些辅助剂充分混合并且将混合物在适当的研磨机中充分研磨,从而提供可以直接用于种子处理的粉末。
可乳化浓缩物
在植物保护中可以使用的具有任何所要求的稀释的乳液可以通过用水稀释从这种浓缩物中获得。
通过将所述活性成分与载体混合并且将混合物在适合的研磨机中研磨而获得即用型尘剂。此类粉剂还可以用于种子的干拌种。
挤出机颗粒
将所述活性成分与这些辅助剂混合并且研磨,并且将所述混合物用水润湿。将混合物挤出并且然后在空气流中干燥。
包衣颗粒剂
活性成分[具有式(I)的化合物] 8%
聚乙二醇(分子量200) 3%
高岭土 89%
将精细研磨的活性成分在混合器中均匀地施用到用聚乙二醇湿润的高岭土上。以所述方式获得非尘的包衣颗粒剂。
悬浮液浓缩物
将精细研磨的活性成分与辅助剂紧密地混合,得到悬浮液浓缩物,从所述悬浮液浓缩液可以通过用水稀释获得任何所希望的稀释度的悬浮液。使用此类稀释物,可以对活的植物连同植物繁殖材料进行处理并且对其针对微生物侵染通过喷雾、浇灌或浸渍进行保护。
种子处理用的可流动性浓缩物
将精细研磨的活性成分与辅助剂紧密地混合,得到悬浮液浓缩物,从所述悬浮液浓缩液可以通过用水稀释获得任何所希望的稀释度的悬浮液。使用此类稀释物,可以对活的植物连同植物繁殖材料进行处理并且对其针对微生物侵染通过喷雾、浇灌或浸渍进行保护。
缓释的胶囊悬浮液
将28份的具有式(I)的化合物的组合与2份的芳族溶剂以及7份的甲苯二异氰酸酯/多亚甲基-聚苯基异氰酸酯-混合物(8:1)进行混合。将此混合物在1.2份的聚乙烯醇、0.05份的消泡剂和51.6份的水的混合物中进行乳化直至达到所希望的粒度。向所述乳液中添加在5.3份水中的2.8份1,6-己二胺混合物。将混合物搅拌直至聚合反应完成。
将获得的胶囊悬浮液通过添加0.25份的增稠剂和3份的分散剂进行稳定。所述胶囊悬浮液配制品含有28%的活性成分。中等胶囊的直径是8-15微米。
将所得配制品作为适用于此目的装置中的水性悬浮液施用到种子上。
制备实例
实例1:此实例阐明了N-乙基-N’-[5-甲氧基-2-甲基-4-[2-(三氟甲基)四氢呋喃-2-基]苯基]-N-甲基-甲脒(化合物1.22)的制备
N-乙基-N’-[5-甲氧基-2-甲基-4-(2,2,2-三氟乙酰基)苯基]-N-甲基-甲脒的制备
将N’-(4-溴-5-甲氧基-2-甲基-苯基)-N-乙基-N-甲基-甲脒(6.0g,21.04mmol)溶解于四氢呋喃(84mL)中并冷却至-78℃。逐滴添加2N在环己烷中的正丁基锂溶液(18.9mL,37.87mmol)。将所得黄色溶液在-78℃下搅拌1h。逐滴添加纯的2,2,2-三氟乙酸乙酯(8.97g,63.128mmol)。在添加结束时,除去冷却槽,并将反应升温至0℃-5℃,并且然后用饱和氯化铵溶液淬灭。将混合物用乙酸乙酯萃取。将有机层用盐水洗涤、经硫酸钠干燥、过滤并减压浓缩。
使用乙酸乙酯/二氯甲烷作为洗脱体系,将残余物通过硅胶色谱法纯化,以得到N-乙基-N’-[5-甲氧基-2-甲基-4-(2,2,2-三氟乙酰基)苯基]-N-甲基-甲脒(5.1g,16.89mmol)。
主要异构体:1H-NMR(400MHz,CDCl3):δ=1.27(t,3H),2.22(s,3H),3.08(s,3H),3.41(d,2H),3.90(s,3H),6.36(br.s,1H),7.56(br.s,2H)
次要异构体:1H-NMR(400MHz,CDCl3):δ=1.27(t,3H),2.22(s,3H),3.08(s,3H),3.62(d,2H),3.90(s,3H),6.36(br.s,1H),7.50(s,1H),7.56(br.s,1H)
比率E/Z:3:5
N-乙基-N’-[4-[1-羟基-1-(三氟甲基)烯丙基]-5-甲氧基-2-甲基-苯基]-N-甲基-甲脒的制备
在-5℃下向N-乙基-N’-[5-甲氧基-2-甲基-4-(2,2,2-三氟乙酰基)苯基]-N-甲基-甲脒(2.00g,6.29mmol)在四氢呋喃(7mL)中的溶液中逐滴添加溴(乙烯基)镁(7.23mL,7.23mmol),并且将反应混合物在0℃下搅拌45min。将反应混合物过滤并倒在冷却的水(15mL)上,然后添加氯化铵水溶液直至沉淀消失,并且将混合物用乙酸乙酯(3×20mL)萃取。将合并的有机层用盐水洗涤,经硫酸钠干燥,过滤并在真空下浓缩,以提供N-乙基-N’-[4-[1-羟基-1-(三氟甲基)烯丙基]-5-甲氧基-2-甲基-苯基]-N-甲基-甲脒(2.20g,5.99mmol)。将材料作为粗品用于下一步骤中。
1H-NMR(400MHz,CDCl3):δ=7.46(1H,m),7.07(1H,s),6.42(2H,m),6.31(1H,s),5.77(1H,d),5.52(1H,d),3.93(3H,br s),3.36(2H,m),3.03(3H,s),2.21(3H,s),1.24(3H,t)
N’-[4-[1-烯丙基氧基-1-(三氟甲基)烯丙基]-5-甲氧基-2-甲基-苯基]-N-乙基-N-甲基-甲脒的制备
向N-乙基-N’-[4-[1-羟基-1-(三氟甲基)烯丙基]-5-甲氧基-2-甲基-苯基]-N-甲基-甲脒(2.25g,6.13mmol)在N,N-二甲基甲酰胺(24.5mL)中的溶液中分批添加氢化钠(0.258g,6.74mmol)。将反应混合物在室温下搅拌30min。然后,逐滴添加溴丙烯(0.536mL,6.13mmol),并且将反应混合物在室温下搅拌过夜。将反应混合物通过缓慢添加饱和氯化铵溶液(20mL)淬灭,并然后用乙酸乙酯(3×15mL)萃取。将合并的有机层用水(2×100mL)、盐水洗涤,经硫酸钠干燥,过滤并在真空下浓缩。使用乙酸乙酯/环己烷作为洗脱体系,将粗材料通过硅胶色谱法纯化,以得到N’-[4-[1-烯丙基氧基-1-(三氟甲基)烯丙基]-5-甲氧基-2-甲基-苯基]-N-乙基-N-甲基-甲脒(1.99g,5.3mmol)。
1H-NMR(400MHz,DMSO):δ=1.14(t,3H),2.12(s,3H),2.86-3.08(m,3H),3.44(m,2H),3.70(s,3H),3.85(d,2H),5.17(dd,1H),5.33(m,2H),5.49(d,1H),5.93(1H,m),6.32(dd,1H),6.52(s,1H),7.17(s,1H),7.59-7.86(m,1H)
N-乙基-N’-[5-甲氧基-2-甲基-4-[5-(三氟甲基)-2H-呋喃-5-基]苯基]-N-甲基-甲脒的制备
将N’-[4-[1-烯丙基氧基-1-(三氟甲基)烯丙基]-5-甲氧基-2-甲基-苯基]-N-乙基-N-甲基-甲脒(1.00g,2.7mmol)在二氯甲烷(54.0mL)中的溶液用氩气脱气,之后添加苯亚甲基-双(三环己基膦)二氯钌(0.113g,0.135mmol)。将反应混合物在室温下搅拌过夜。将反应混合物在真空下浓缩,然后将残余物溶于水(60mL)中并用HCl 2M酸化。将混合物用二乙醚(2×20mL)萃取,然后将水层用碳酸氢钠水溶液碱化(直至pH 10)。将溶液用二氯甲烷(3×20mL)萃取,并且将合并的有机层用盐水洗涤,经硫酸钠干燥,过滤并在真空下浓缩。
使用乙酸乙酯/环己烷作为洗脱体系,将粗材料通过硅胶色谱法纯化,以得到N-乙基-N’-[5-甲氧基-2-甲基-4-[5-(三氟甲基)-2H-呋喃-5-基]苯基]-N-甲基-甲脒(0.90g,2.6mmol)。
1H-NMR(400MHz,DMSO):δ=8.22-8.62(1H,m),7.49(1H,s),7.14(2H,m),6.26-6.69(2H,m),4.59-4.92(2H,m),3.86(3H,s),3.57-3.78(2H,m),3.28-3.36(3H,m),2.30(3H,m),1.28(3H,t)。
N-乙基-N’-[5-甲氧基-2-甲基-4-[2-(三氟甲基)四氢呋喃-2-基]苯基]-N-甲基-甲脒(化合物1.22)的制备
将N-乙基-N’-[5-甲氧基-2-甲基-4-[5-(三氟甲基)-2H-呋喃-5-基]苯基]-N-甲基-甲脒(200mg,0.58mmol)在乙醇(6mL)中的溶液用氩气脱气,并添加钯炭(0.01869g,催化剂)。将反应混合物在室温下在氢气氛下搅拌4h。将反应混合物通过硅藻土过滤并且将滤液在真空下浓缩。将固体溶于水(20mL)中,并用HCl酸化直至达到pH1。将混合物用二乙醚(10mL)萃取并且将水层用NaHCO3碱化。将混合物用二氯甲烷(3×10mL)萃取,并将合并的有机层用盐水洗涤、经硫酸钠干燥、过滤并在真空下浓缩,以提供N-乙基-N’-[5-甲氧基-2-甲基-4-[2-(三氟甲基)四氢呋喃-2-基]苯基]-N-甲基-甲脒(化合物1.22,98mg,0.29mmol)。
1H-NMR(400MHz,DMSO):δ=7.72(1H,s),7.27(1H,s),6.48(1H,s),3.77(4H,s),3.33(2H,m),2.99(3H,br s),2.64(1H,ddd),2.38(1H,dt),2.10(3H,s),2.00(2H,m),1.14(3H,m)。
表E:某些具有式(I)的化合物的物理(LC/MS)数据
所使用的LC/MS(液相色谱法质谱法)方法:
(来自沃特斯公司(Waters)的ACQUITY UPLC,Phenomenex Gemini C18,3μm粒度,110埃,30×3mm柱,1.7mL/min.,60℃,H2O+0.05%HCOOH(95%)/CH3CN/MeOH 4:1+0.04%HCOOH(5%)-2min.-CH3CN/MeOH 4:1+0.04%HCOOH(5%)-0.8min.,来自沃特斯公司的ACQUITY SQD质谱仪,电离法:电喷雾(ESI),极性:正离子,毛细管(kV)3.00,锥孔(V)20.00,萃取器(V)3.00,源温度(℃)150,去溶剂化温度(℃)400,锥孔气体流量(L/Hr)60,去溶剂化气体流量(L/Hr)700))。
生物学实例
小麦白粉病菌(Blumeria graminis f.sp.tritici,Erysiphe graminis
f.sp.Tritici)/小麦/叶圆片预防性(小麦上的白粉病)
将小麦叶段栽培品种Kanzler置于多孔板(24孔规格)的琼脂上,并且用在水中稀释的配制的测试化合物喷雾。在施用后1天,通过在测试板之上摇动白粉病感染的植物来接种叶圆片。在气候箱中,在24h黑暗、随后是12h光照/12h黑暗的光照方案下,在20℃和60%rh下孵育经接种的叶圆片,并且在未处理的对照叶段上出现适当水平的疾病损害时(施用后6-8天),作为与未处理的相比的疾病控制百分比来评估化合物的活性。
在此测试中,当与在相同条件下示出大规模的疾病发展的未处理的对照叶圆片相比时,以下化合物在200ppm下给出至少80%的疾病控制:
1.21和1.22
豆薯层锈菌/大豆/叶圆片预防法(大豆锈病)
在喷雾室中,将四周龄大豆植物用稀释于水中的配制的测试化合物进行喷雾。在施用后一天,从处理的植物上切割下叶圆片并置于24孔板中的琼脂上。将叶圆片通过用孢子悬浮液在它们的下方叶表面上进行喷雾来接种。在气候室中在黑暗下在20℃和75%rh下经过24-36小时的温育期后,然后将叶圆片保持在20℃与12h光照/天和75%rh下。在未处理的检验植物上出现适当水平的疾病时(施用后12-14天),评估被疾病覆盖的百分比叶圆片面积。
在此测试中,当与在相同条件下示出大规模的疾病发展的未处理的对照叶圆片相比时,以下化合物在200ppm下给出至少80%的疾病控制:
1.21和1.22
小麦隐匿柄锈菌/小麦/叶圆片预防法(褐锈病)
将小麦叶段栽培品种Kanzler置于多孔板(24孔规格)的琼脂上,并且用在水中稀释的配制的测试化合物喷雾。在施用后1天,用真菌的孢子悬液接种叶圆片。在气候室中,在12h光照/12h黑暗的光照方案下,在19℃和75%rh下孵育经接种的叶段,并且在未处理的对照叶段中出现适当水平的疾病损害时(施用后7-9天),作为与未处理的相比的疾病控制百分比来评估化合物的活性。
在此测试中,当与在相同条件下示出大规模的疾病发展的未处理的对照叶圆片相比时,以下化合物在200ppm下给出至少80%的疾病控制:
1.21和1.22
小麦隐匿柄锈菌(Puccinia recondita f.sp.tritici)/小麦/叶圆片治疗法(褐
锈病)
将小麦叶段栽培品种Kanzler置于多孔板(24孔规格)内的琼脂上。用真菌的孢子悬浮液接种这些叶碎片。在19℃和75%rh下,在黑暗中储存这些板。在接种后1天,施用在水中稀释的经配制的测试化合物。在气候室中,在12h光照/12h黑暗的光照方案下,在19℃和75%rh下孵育叶段,并且在未处理的对照叶段中出现适当水平的疾病损害时(施用后6-8天),作为与未处理的相比的疾病控制百分比来评估化合物的活性。
在此测试中,当与在相同条件下示出大规模的疾病发展的未处理的对照叶圆片相比时,以下化合物在200ppm下给出至少80%的疾病控制:
1.21和1.22
Claims (15)
2.根据权利要求1所述的化合物,其中,R1和R2各自独立地是C1-C4烷基。
3.根据权利要求1或2所述的化合物,其中,R3是卤素或C1-C3烷基。
4.根据权利要求1、2或3中任一项所述的化合物,其中,R4和R5各自独立地选自氢和甲基,或R4和R5与它们所附接的碳原子一起形成羰基。
5.根据权利要求1、2、3或4中任一项所述的化合物,其中,R1和R2各自独立地选自甲基、乙基和异丙基。
6.根据权利要求1、2、3、4或5中任一项所述的化合物,其中,R3是氟、氯或甲基。
7.根据权利要求1、2、3、4、5或6中任一项所述的化合物,其中,R4和R5都是氢,或R4和R5与它们所附接的碳原子一起形成羰基。
8.根据权利要求1、2、3、4、5、6或7中任一项所述的化合物,其中,R1是甲基、乙基或异丙基并且R2是甲基或乙基。
9.根据权利要求1、2、3、4、5、6、7或8中任一项所述的化合物,其中,R3是氯或甲基并且R4和R5都是氢。
10.根据权利要求1所述的化合物,其中,
R1和R2各自独立地选自甲基、乙基和异丙基;
R3是氟、氯或甲基;
R4和R5都是氢,或R4和R5与它们所附接的碳原子一起形成羰基;
X是O、S或NCH3;
n是0或1;
或其盐、金属络合物、立体异构体或N-氧化物。
11.根据权利要求1所述的化合物,其中,所述化合物选自:
N-乙基-N’-[5-羟基-2-甲基-4-[2-(三氟甲基)四氢呋喃-2-基]苯基]-N-甲基-甲脒;
N’-[5-羟基-2-甲基-4-[2-(三氟甲基)四氢呋喃-2-基]苯基]-N-异丙基-N-甲基-甲脒;
N’-[2-氯-5-羟基-4-[2-(三氟甲基)四氢呋喃-2-基]苯基]-N-乙基-N-甲基-甲脒;
N-乙基-N’-[5-羟基-2-甲基-4-[4-氧代-2-(三氟甲基)四氢呋喃-2-基]苯基]-N-甲基-甲脒;
N-乙基-N’-[5-羟基-2-甲基-4-[2-(三氟甲基)四氢噻吩-2-基]苯基]-N-甲基-甲脒;或者
N-乙基-N’-[5-羟基-2-甲基-4-[2-(三氟甲基)氧杂环丁烷-2-基]苯基]-N-甲基-甲脒;
或其盐、金属络合物、立体异构体或N-氧化物。
12.根据权利要求1、2、3、4、5、6、7、8、9或10中任一项所述的化合物,其中,X是O或S。
13.一种组合物,其包含杀真菌有效量的如权利要求1–12中任一项所定义的具有式(I)的化合物。
14.根据权利要求13所述的组合物,其中,所述组合物进一步包含至少一种另外的活性成分和/或稀释剂。
15.一种对抗、预防或控制植物病原性真菌的方法,所述方法包括向植物病原性真菌、植物病原性真菌的场所、或易受植物病原性真菌攻击的植物、或其繁殖材料施用杀真菌有效量的如权利要求1–12中任一项所定义的具有式(I)的化合物、或包含杀真菌有效量的如权利要求1–12中任一项所定义的具有式(I)的化合物的组合物。
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US10934265B2 (en) | 2021-03-02 |
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EP3720846A1 (en) | 2020-10-14 |
AR113865A1 (es) | 2020-06-17 |
BR112020011083A2 (pt) | 2020-11-17 |
CL2020001466A1 (es) | 2020-09-25 |
CO2020006821A2 (es) | 2020-06-19 |
IL275046A (en) | 2020-07-30 |
MX2020005759A (es) | 2020-08-20 |
WO2019110427A1 (en) | 2019-06-13 |
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