CN88101407A - 苯甲醛肟衍生物 - Google Patents
苯甲醛肟衍生物 Download PDFInfo
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- CN88101407A CN88101407A CN198888101407A CN88101407A CN88101407A CN 88101407 A CN88101407 A CN 88101407A CN 198888101407 A CN198888101407 A CN 198888101407A CN 88101407 A CN88101407 A CN 88101407A CN 88101407 A CN88101407 A CN 88101407A
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
- C07C317/48—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/60—Thiocarboxylic acids having sulfur atoms of thiocarboxyl groups further doubly-bound to oxygen atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/10—Sulfones; Sulfoxides
-
- 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
- A01N43/10—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 sulfur 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
- 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
- A01N47/02—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 no bond to a nitrogen atom
- A01N47/06—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 no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
-
- 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
- C07D333/26—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 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
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Abstract
如通式(I)所示的具抗真菌活性的苯甲醛肟衍生物,式(I)中R,R1,R2,R3,R4,R5如说明书中所定义。
Description
本发明是有关新型的苯甲醛肟衍生物,其制备方法以及其作为防止害虫药剂,尤其是抗真菌剂的应用。
多种乙醛肟衍生物是已知的,例如芳基磺酰基苯甲醛肟类(如α-苯基磺酰基-2,6-二氯一苯甲醛肟)及其用于防治害虫的应用,尤其是其用于防止小麦腥黑穗病的应用是众所周知的(参见瑞士专利423,350号)。苯基-吡啶-苯甲醛肟类(如苯基-O-乙基羰基-吡啶苯甲醛肟)及其抗组胺的作用也是已知的(参见J.Plarm.Sci.56(1967),10号,1354-1357页)。
已经发现如通式(Ⅰ)所示的新型的苯甲醛肟衍生物,式(Ⅰ)中:
R表示烷基,烷氧基,卤代烷基,卤代烷氧基或链烯氧基,或芳基或芳氧基,在各种情况下,可选择性地被相同的或不相同的一个或多个取代基所取代,或芳烷氧基,其中芳基可选择性地被相同的或不相同的一个或多个取代基所取代,或表示环烷氧基,该基团可选择性地被相同的或不相同的一个或多个取代基所取代,或表示杂环基,该基团可选择性地被相同的或不相同的一个或多个取代基所取代,
R1表示氢,卤素,烷基或烷氧基,
R2表示氢,烷基或卤代烷基,
R3表示氢或卤素,
R4表示卤素,以及
R5表示氢或卤素。
此外还发现如式(Ⅰ)所示的苯甲醛肟衍生物的制法,即可通过将通式(Ⅱ)所示的苯基磺酰基苯甲醛肟与通式(Ⅲ)所示的碳酰化合物反应而制得。需要时,反应在溶剂或稀释剂存在下进行,并且需要时,可在酸结合剂存在下进行。
式(Ⅰ)中,
R表示烷基,烷氧基,卤代烷基,卤代烷氧基或链烯氧基,或芳基或芳氧基,在各种情况下,可选择性地被相同的或不相同的一个或多个取代基取代,或芳烷氧基,其中芳基可选择性地被相同的或不相同的,一个或多个取代基所取代,或表示环烷氧基,该基团可选择性地被相同的或不相同的一个或多个取代基取代,或表示杂环基,该基团可选择性地被相同的或不相同的一个或多个取代基取代,
R1表示氢,卤素,烷基或烷氧基,
R2表示氢,烷基或卤代烷基,
R3表示氢或卤素,
R4表示卤素,以及
R5表示氢或卤素。
式(Ⅱ)中,R1,R2,R3,R4和R5如上述所定义。
式(Ⅲ)中,R具有上述定义,并且X表示卤原子(最好是氯原子)或-O-COR-基团,其中R具上述定义。
按本发明的式(Ⅰ)苯甲醛肟衍生物具有很强的生化性能,特别是抗真菌特性。
令人出乎意料的是,按本发明的化合物显示出较高的活性,特别是抗真菌活性,其活性与先有技术已知的化合物对比来看,虽然已知的各化合物在结构上来看和/或从它们的作用来看都密切相关,但本发明化合物活性要高很多。
按本发明的式(Ⅰ)化合物可制备成顺式或反式异构体,或是其不同组份的异构体混合物。因此,本发明涉及到其纯异构体及其异构体混合物。
R,R1和R2中的烷基,R和R1中的烷氧基的烷基部分,可以是直链或支链的,而且最好在各种情况下,各带1-6个,特别是1-4个碳原子。可举出的例子是:甲基,乙基,正丙基,异丙基,正丁基,仲丁基,异丁基,叔丁基,正戊基,异戊基,仲戊基,正己基,仲己基,甲氧基,乙氧基,正丙氧基,异丙氧基,正丁氧基,异丁氧基,仲丁氧基,叔丁氧基,正戊氧基,异戊氧基,仲戊氧基,正己氧基和仲己氧基。
R表示的链烯氧基中优选含有2-6个,最好含2-5个(特别是2或3个)碳原子。可举出例子是:乙烯基,烯丙基,丙烯-1-基,丁烯基和戊烯基。
R和R2表示的卤代烷基或卤代烷氧基的卤代烷基部分,在各种情况下优选含有1-6个,最好含1-4个(特别是1或2个)碳原子;并且优选含有1-9个,最好是1-5个(特别是1-4个)相同的或不相同的卤原子。可举出的例子是:一氯代甲基,三氯甲基,三氟甲基,二氯氟代甲基,三氯乙基,四氯乙基,三氯甲氧基,三氯乙氧基和四氯乙氧基。
R至R5中的卤素,包括例如卤代烷基和卤代烷氧基或芳基取代基等的卤素,是指氟,氯,溴或碘,若非特别指出,尤其是指氟或氯。
芳基,包括R所表示的芳氧基中的芳基,可表示带6-10个碳原子的芳香烃。可举出的例子是:苯基和萘基,优选用苯基。
R表示的芳烷氧基中的芳烷基可表示带7-18个碳原子的基团,可以是被带6-10碳原子的芳基所取代的直链的或支链的烷基(带1-6个碳原子)。可举出的例子是:苄基,苯乙基和苯丙基,优选用苄基。
环烷氧基中的环烷基可表示带5-7个碳原子的环烃,优选单环烃。可以举出的例子是:环戊基,环己基和环庚基。优选用环戊基和环己基。
杂环基可以是饱和的,或部分和完全不饱和的5-8元环基团,优选5元或6元环,并带有1-3个,优选带1或2个(特别是1个)杂原子。可举例的杂原子是:硫,氧或氮,特别是硫。
所述的芳基,芳氧基和芳烷氧基可以是未被取代的或被取代的;取代基可以是1-5个,优选1-3个,特别是1或2个,所述取代基可选自:带1-4个碳原子的低级烷基(如甲基,乙基,丙基,异丙基,丁基和异丁基),带1-4个碳原子的低级烷氧基(如甲氧基,乙氧基,丙氧基,异丙氧基,丁氧基和异丁氧基),以及卤素(如氟,氯和溴)。其它的取代基可以是:硝基和乙酰基。
所述环烷氧基可以是未被取代的或被取代的,取代基可以是1-5个,优选1-3个,特别是1或2个,所述取代基可选自:带1-4个碳原子的低级烷基(如甲基,乙基,丙基,异丙基,正丁基和仲丁基,异丁基和叔丁基)。
所述的杂环基可以是未被取代的或被取代的。取代基可以1-3个,优选1个。所述取代基可以选自如上述所列出的带1-4个碳原子的低级烷基。
式(Ⅰ)给出了按本发明的苯甲醛肟的一般定义。优选的式(Ⅰ)化合物中,
R表示带1-6碳原子的直链或支链烷基,或表示带1-6个碳原子的直链或支链烷氧基,或表示卤代烷基或卤代烷氧基,在各种情况下,其中在直链或支链的卤代烷基中带1-6个碳原子,及带1-9个相同或不相的卤原子,或表示带2-6个碳原子的直链或支链的链烯氧基,或表示带6-10个碳原子的芳基或芳氧基,可以是未取代的,或在各种情况下被1个至5个相同的或不相同的取代基所取代,所述取代基选自带1-4个碳原子的直链或支链烷基,带1-4个碳原子的支链或支链烷氧基,卤素,硝基和乙酰基,或表示芳烷氧基,其中芳基部分带6-12个碳原子,直链或支链烷基部分带1-6个碳原子,可以是未取代的,或是被相同的或不相同的一个至5个取代基所取代,所述取代基选自:带1-4个碳原子的直链或支链烷基和烷氧基,卤素,硝基和乙酰基,或表示环烷氧基,其中环烷基部分带5-7个碳原子,可以是未被取代的,或是被相同的或不相同的1个至5个取代基所取代,所述取代基选自带1-4个碳原子的直链或支链烷基,或带5-8元环的饱和的或部分或完全不饱和的杂环基,可含有1-3个杂原子,并且可以是未取代的,或是被相同的或不相同的1个至3个取代基取代,所述取代基选自带1-4个碳原子的直链或支链烷基,
R1表示氢,卤素,带1-6个碳原子的直链或支链烷基,或带1-6个碳原子的直链或支链烷氧基,
R2表示氢,或带1-6个碳原子的直链或支链烷基,或表示带1-6个碳原子和1-9个相同或不相同卤原子的直链或支链卤代烷基,
R3表示氢或卤素,
R4表示卤素,并且
R5表示氢或卤素。
比较优选的式(Ⅰ)化合物中,
R表示带1-4个碳原子的直链或支链烷基,或表示带1-4个碳原子的直链或支链烷氧基,或表示卤代烷基或卤代烷氧基,其中在直链或支链的卤代烷基中带1-4个碳原子,及带1-5个相同的或不相同的卤原子,或表示带2-5个碳原子的直链或支链链烯氧基,或表示苯基或苯氧基,可以是未取代的,或是在各情况下被1个至5个相同的或不相同的1个至5个取代基所取代,所述取代基选自带1-3个碳原子的直链或支链烷基,带1-3个碳原子的直链或支链烷氧基,卤素,硝基和乙酰基,或表示苄氧基,苯乙氧基或苯丙氧基,可以是未被取代的,或者是被相同的或不相同的一个至3个取代基所取代,所述取代基选自带1-3个碳原子的直链或支链烷基和烷氧基,卤素,硝基和乙酰基,或表示环烷氧基,其中环烷基部分带5-7个碳原子,可以是未取代的,或是被相同的或不相同的1个至3个取代基所取代,所述取代基选自带1-3个碳原子的直链或支链烷基,或表示带5-7元环的饱和的或部分或全部不饱和的杂环基,可含有1或2个硫,氮和/或氧原子,可以是未被取代的,或者被带1-3个碳原子的直链或支链烷基单取代,
R1表示氢,卤素,带1-4个碳原子的直链或支链烷基,或带1-4个碳原子的直链或支链烷氧基,
R2表示氢,或带1-4个碳原子的直链或支链烷基,或表示带1-4个碳原子和1-5个相同的或不相同卤原子的直链或支链卤代烷基,
R3表示氢或卤素,
R4表示卤素,以及
R5表示氢或卤素。
特别优选的式(Ⅰ)化合物中,
R表示带1-6个碳原子的直链或支链烷基,或表示带1-6个碳原子的直链或支链烷氧基,或表示卤代烷基或卤代烷氧基,在各种情况下,其中在直链或支链的卤代烷基中带1或2个碳原子,及带1-4个相同的或不相同的卤原子,或表示带2-3个碳原子的直链或支链的链烯氧基,或表示苯基或苯氧基,可以是未取代的,或者是在各种情况下被相同的或不相同的1个或2个取代基所取代,所述取代基选自带1个或2个碳原子的烷基,带1个或2个碳原子的烷氧基,卤素,硝基和乙酰基,或表示苄基,可以是未取代的,或是被相同的或不相同的1个至3个取代基取代,所述取代基选自带1个或2个碳原子的烷基、烷氧基和卤素,或表示环烷氧基,其中环烷基部分带5个或6个碳原子,可以是未被取代的,或是被相同的或不相同的1个至3个取代基所取代,所述取代基选自带1或2个碳原子的烷基,或表示带5或6元环的不饱和杂环基,可含有氮原子或硫原子,可以是未被取代的,或者是被相同的或不相同的1个或2个取代基所取代,所述取代基选自带1个或2个碳原子的烷基;
R1表示氢,卤素,带1个或2个碳原子的烷基,或带1个或2个碳原子的烷氧基,
R2表示氢或带1个或2个碳原子的烷基,或表示带1个或2个碳原子和带1-3个相同的或不相同的卤原子的卤代烷基,
R3表示氢或卤素,
R4表示卤素,并且
R5表示氢或卤素。
特别应提出的式(Ⅰ)化合物中,
R表示甲基,乙基,甲氧基,乙氧基,正丙氧基,异丙氧基,异丁氧基,烯丙氧基,2,2,2-三氯乙氧基,苄氧基,氯代甲基,苯基,2,6-二氯苯基,2,4-二氯苯基,苯氧基,噻吩基或环己氧基,
R1表示氢,氟,氯,甲基或甲氧基,
R2表示氢或三氟甲基,
R3表示氢,氟或氯,
R4表示氟或氯,并且
R5表示氢或氯。
如果用2,6-二氟-α-(4-甲基苯基磺酰基)-苯甲醛肟和乙酸酐作为起始原料,按本发明方法的反应过程可由下列反应式表示:
实施本发明方法所需的作为起始原料的通式(Ⅱ)苯基磺酰基-苯甲醛肟,在有些情况下是已知的。各已知化合物和新化合物可按各相似方法制备,例如瑞士专利432,350号,例Ⅶ中所述的方法,其中用式(Ⅳ)所示的α-卤代-苯甲醛肟与式(Ⅴ)所示的苯亚磺酸反应,需要时反应在溶剂存在下和需要时在酸结合剂存在下进行。
式(Ⅳ)中,R3,R4和R5如上述所定义,Hal表示卤素,最好是氯。
式(Ⅴ)中,R1和R2如上述所定义,M表示氢或一相当的碱金属。
亚磺酸为一已知化合物。
式(Ⅲ)给出了另一所需的起始原料物的定义。它们在有机化学中是已知化合物。
需要时,按本发明方法,反应可在溶剂或稀释剂存在下进行。可以应用的溶剂或稀释剂基本上都是惰性的有机溶剂。优选的有机溶剂为烃类,可以是卤代烃,例如苯,甲苯,二甲苯,二氯甲烷,氯仿,四氯化碳,氯代苯和二氯代苯,还有可用醚类,例如二乙醚和二丁醚,甘醇二甲醚和二甘醇二甲醚,四氢呋喃和二噁烷,还可用酮类,例如丙酮,甲乙酮,甲基异丙基酮和甲基异丁基酮,还可用酯类,例如乙酸甲酯和乙酸乙酯,还可用腈类,例如乙腈,丙腈,苯腈和戊二酸二腈,此外还可用酰胺类,例如二甲基甲酰胺。
按本发明方法可应用的酸结合剂是常用的无机或有机酸结合剂。可列举的酸结合剂是例如:叔胺类,如三乙胺,吡啶,三亚乙基二胺及其它。
按本发明的方法,反应温度可在一定范围内变化。反应温度一般为0-120℃,最好是20-70℃。
反应一般在常压下进行。实施本发明方法时,通常将式(Ⅱ)化合物与等摩尔量的酸结合剂溶于溶剂中,加入式(Ⅲ)的碳酰化合物,最好也是以等摩尔量加入。并且按一般常用方法进行处理。
应举出的特别情况是,如果X代表-O-COR,即应用了式(Ⅲ)的羧酸酐时,反应中不用溶剂,而应用过量的酐,它既是作为起始原料物,也是溶剂。并且按一般常用方法进行处理。
按本发明的活性化合物具很强的生化作用,在实际应用中可用来防止无益害虫。活性化合物适用于作为防治害虫药剂,尤其是作为抗真菌剂。
保护植物的抗真菌药剂用于对抗下列各种菌类,如根肿病菌纲,卵菌纲,壶菌纲,接合菌纲,子囊菌纲,担子菌纲和半知菌纲。
保护植物的抗菌药剂用于对抗下列各种菌类,例假单胞菌科,根瘤菌科,肠杆菌科,棒状杆菌科和链霉菌科。
上列的真菌和细菌病害的各种成因生物体属种中,可举例如下(但不限于此):黄杆菌属种,如黄杆菌属Campestris pv.oryzae;假单胞菌属种,如假单胞菌属syringae pv.lachrymans;Erwinia属种,如Erwinia amylovora;腐霉属种,如腐霉属ultimum;疫霉属种,如疫霉属infestans;假霜霉菌属种,如假霜霉菌属humuli或假霜霉菌属cubensis;葡萄霜霉属种,如葡萄霜霉菌属Viticola;霜霉属种,如霜霉属pisi或P.brassicae;白粉菌属种,如白粉菌属graminis;直丝单囊属种,如直丝单囊属fulginea;叉丝单囊壳属种,如叉丝单囊壳属leucotricha;黑星菌属种,如黑星菌属inaequalis;核腔菌属种,如核腔菌属teres或P.graminea(分生孢子型:Drechslera,联:Helminthosporium);旋孢腔菌属种,如旋孢腔菌属sativus(分生孢子型:Drechslera,联Helminthosporium);单胞锈属种,如单胞锈属appendiculatus;柄锈属种,如柄锈属recondita;腥黑粉菌属种,如腥黑粉菌属caries;黑粉菌属种,如黑粉菌属nuda或黑粉菌属avenae;薄膜革菌属种,如薄膜革菌属sasakii;Pyricularia菌属种,如Pyricularia oryzae;镰刀菌属种,如镰刀菌属culmorum;葡萄孢属种,如葡萄孢属cinerea;壳针孢属种,如壳针孢属nodorum;小球腔属种,如小球腔属nodorum;尾孢菌属种,如尾孢菌属canescens;交链孢属种,如交链孢属brassicae和假单尾孢属种,如假单尾孢属herpotrichoides。
应用对抗植物病虫害所需浓度时,各种植物对所述活性化合物的耐药力良好,因而可应用于对各种植物体的处理,如出土的植物体,营养体繁殖苗木和种子,以及对土镶的处理。
所述活性化合物可转化成各种常用的配方剂型,如溶液,乳化液,悬浮液,粉剂,泡沫剂,糊剂,颗粒剂,烟雾剂,聚合物中的微囊剂,种子包敷组合物以及ULV剂型等。
这些剂型可用各种已知方法制备,例如,将活性化合物与各种增充剂混合起来,所述增充剂如液体溶剂,加压液化气和/或固态载体,并且可任选用表面活性剂,如乳化剂和/或分散剂,和/或起泡剂。在用水作为增充剂的情况下,如可用有机溶剂作为辅助溶剂。作为液体溶剂,可举例的适用的主要化合物是,芳香族,如二甲苯,甲苯或烷基萘,氯代芳族或氯代脂肪烃,如氯代苯,氯代乙烯或二氯甲烷,脂肪烃,如环己烷或石蜡,如矿物油馏分,醇类,如丁醇或甘醇及其醚和酯,酮类,如丙酮,甲乙酮,甲基异丁基酮或环己酮,强极性溶剂,如二甲基甲酰胺和二甲基亚砜,还有水。液化气增充剂或载体是指,在常温、常压下呈气态的各种液体,例如烟雾剂促成剂,如卤代烃和丁烷,丙烷,氮和二氧化碳。适用的固态载体为例如磨细的天然矿物质,如高岭土,粘土,滑石,白垩,石英,活性白土,蒙脱土或藻土,以及磨细的合成矿物质,如高度分散的硅酸,矾土和硅酸盐。适用的颗粒剂固态载体为例如经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,还有无机和有机质的合成颗粒物,以及有机材料的颗粒物,如锯屑,花生壳,玉米蕊和烟草杆。适用的乳化剂和/或起泡剂为例如非离子型和阴离子型乳化剂,如聚氧乙烯-脂肪酸酯,聚氧乙烯-脂肪醇醚,如烷芳基聚乙二醇醚,烷基磺酸盐,烷基硫酸盐,芳基磺酸盐以及清蛋白水解产物。适用的分散剂为例如木质素亚硫酸盐废液和甲基纤维素。
药剂配方中可应用的各种粘合剂为例如羧甲基纤维素,和粉状,颗粒状或晶格状的天然或合成的聚合物,如阿拉伯树胶,聚乙烯醇和聚乙酸乙烯酯,以及天然磷酯,如脑磷酯和卵磷酯,和各种合成的磷酯。其它可应用的附加剂为矿物油和植物油。
可以应用各种加色剂,例如无机颜料如氧化铁,氧化钛和普鲁土蓝,有机染料如茜素染料,偶氮染料和金属钛菁染料,以及微量的营养剂如铁盐,锰盐,硼盐,铜盐,钴盐,钼盐和锌盐。
药剂中一般含有0.1-95%(重量),最好含0.5-90%(重量)的活性化合物。
按本发明的活性化合物在药剂中可与下列各已知的其它化合物以混合物形式存在,如杀菌剂,杀虫剂,杀螨剂和除草剂,也可以和肥料和其它生长调节剂混合。
本发明活性化合物可单独使用,或以它们的药剂配方形式,或由其制备的各种应用形式来使用,如各种备用的溶液,可乳化浓缩液,乳化液,泡沫剂,悬浮液,可湿性粉末,糊剂,可溶粉末,粉剂和颗粒剂,它们可以各种常用的方式使用,如浇水,喷洒,喷雾,撒布,撒粉,喷泡沫,刷布及类似方法。另外也可采用微容方式使用活性化合物,或以注入活性化合物配方或活性化合物本身的方式,将活性化合物施用于土壤中。各种植物种子也可以处理。
处理各种植物体时,在使用剂型中的活性化合物浓度可以在相当的范围内变化。一般来说浓度范围为1-0.0001%(重量),而最好是0.5-0.001%(重量)。
处理种子时,活性化合物的一般需用量为每公斤种子用量0.001-50克,最好是0.01-10克。
处理土壤时,施用于作用地方的活性化合物浓度为0.00001-0.1%(重量),而最好是0.0001-0.02%(重量)。
按本发明的式(Ⅰ)化合物对于蔬菜,果类,谷类和稻类病害的病原生物体显示了极强的对抗作用,其中的病原体可举例的是,黑星菌种,疫霉属infestans,小球腔属nodorum和Pyricularia oryzav,以及核腔菌属teres,旋孢腔菌属sativus和柄锈属recondita。此外,在试管内试验,一定浓度的活性化合物也显示了抗细菌作用,
按本发明的物质,在适当浓度下也显示出了除草作用。
应用实施例
在以下各应用实施例中,用如下化合物作为对照物,即α-苯磺酰2,6-二氯苯甲醛肟(见瑞士专利423,350号;例Ⅶ)。
例A
Pyricularia试验(稻)/保护性,
溶剂:12.5份(重量)丙酮,
乳化剂:0.3份(重量)烷芳基聚乙二醇醚,
为制备活性化合物的适用制剂,将1份(重量)的活性化合物与所述份量的溶剂混合,并用水和所述份量的乳化剂将浓液稀释至所需浓度。
为试验保护活性,用活性化合物制剂来喷洒稻幼苗至湿透滴水。喷洒后,将表层整干,将Pyrucularia oryzae的芽孢水悬液接种至稻苗体上。植体置于温室中,保持100%相对大气湿度和25℃。
移植后4日进行观测病害情况。
通过本实验表明,按本发明各化合物与先有技术比较,在活性化合物浓度如0.025%时,可清楚地显示出其优越的活性。
例B.
小球腔属nodorum试验(小麦)/保护性
溶剂:100份(重量)二甲基甲酰胺
乳化剂:0.25份(重量)烷芳基聚乙二醇醚
为制备活性化合物的适用制剂,将1份(重量)的活性化合物与所述份量的溶剂和乳化剂相混合,并将浓液用水稀释至所需的浓度。
为试验保护活性,用活性化合物制剂喷洒植物体幼苗至结露水湿透。喷洒后,将表层整干,用小球腔属nodorum的分生孢子悬液来喷洒植物体。植物体于培育室中放置48小时,并保持20℃和100%大气相对湿度。
然后将植物体置于温室中,并保持15℃及80%大气相对湿度。
接种后10日观测病害情况。
与先有技术比较,按本发明的大多数化合物,在活性化合物浓度如0.025%时可清楚地显示出其优越的活性。
例C.
疫霉属试验(番茄)/保护性
溶剂:4.7份(重量)丙酮
乳化剂:0.3份(重量)烷芳基聚乙二醇醚
为制备活性化合物的适用制剂,将1份(重量)的活性化合物与所述份量的溶剂和乳化剂混合,并用水将浓液稀释到所需浓度。
为试验保护活性,用活性化合物制剂来喷洒植物体幼苗至湿透滴水。喷洒后,将表层整干,将疫霉属infestans孢子水悬液接种至植物体。
植物体置于培养室中,并保持100%相对大气湿度和20℃。
接种后3日进行观测。
与先有技术比较,按本发明的多种化合物当浓度为10ppm时可显示出其优越的活性。
例D.
黑星菌属(苹果)/保护性
溶剂:4.7份(重量)丙酮
乳化剂:0.3份(重量)烷芳基聚乙二醇醚
为制备活性化合物的适用制剂,将1份(重量)的活性化合物与所述份量的溶剂和乳化剂混合,并将浓液用水稀释至所需浓度。
为试验保护性,用活性化合物制剂喷洒植物体幼苗至湿透滴水,喷洒后将表层整干,然后将苹果痂斑病原生物体(黑星菌属inaequalis)接种到植物体上。植物体于培育室中设置1日,并保持20℃及100%大气相对湿度。
然后将植物置于温室中,并保持20℃和70%大气相对湿度。
接种后12日进行观测。
与先有技术比较,各化合物于活性性浓度为10ppm时清楚地显示出具优越的活性。
制备实施例
实施例1
将25.8克(0.075摩尔)的2,6-二氯-α-(4-甲基-苯基磺酰基)-苯甲醛肟与100毫升乙酸酐在70-80℃下加热24小时。然后将反应混合物浓缩,热残余物与异丙醇搅拌,热吸滤,洗涤并干燥。制得23.8克(82%收率)的所需产物,熔点为179℃。
用类似方法制得式(Ⅰ)各化合物。
起始物质的制备
实施例1A
将19.2克(0.1摩尔)的α-氯-2,6-二氯-苯甲醛肟溶于200毫升甲醇,并于室温下加入23.2克(0.1摩尔)的3-三氟甲基苯亚磺酸钠。反应混合物在该温度下保持15小时,然后倒入1升冰水中,搅拌下抽提,将产物吸滤,洗涤及干燥。反应产物在甲苯中重结晶。制得24克(62.5%收率)的α-3-三氟甲基苯基磺酰基-2,6-二氟苯甲醛肟,熔点为127℃。
用类似的方法可制得式(Ⅱ)各化合物。
实施 R1R2R3R4R5物理数据
例号 (熔点℃)
2A CH3H H Cl Cl 143
3A Cl H Cl F H 158
4A CH3H Cl F H 170
5A H H Cl F H 143
6A OCH3H Cl F H 145
7A CH3H H Cl H 147
8A H H Cl Cl H 148
9A F H Cl Cl H 154
10A Cl H Cl Cl H 111
11A H H F F H 149
12A Cl H F F H 171
13A CH3H F F H 166
14A OCH3H Cl Cl H 163
15A -OCH3H F F H 145
16A -OCH3H Cl H H 141
17A H CF3Cl Cl H 148
Claims (10)
2、按权利要求1的苯甲醛肟衍生物及其异构体或其异构体的混合物,其中式(Ⅰ)中,
R表示带1-6个碳原子的直链或支链的烷基,或表示带1-6个碳原子的直链或支链的烷氧基,或表示卤代烷基或卤代烷氧基,其中在直链或支链的卤代烷基中带1-6个碳原子,及带1-9个相同的或不相同的卤原子,或表示带2-6个碳原子的直链的或支链的链烯氧基,或表示带6-10个碳原子的芳基或芳氧基,可以是未取代的,或者在各种情况下被1个至5个相同的或不相同的取代基所取代,所述取代基选自下列基团,即带1-4个碳原子的直链或支链烷基,带1-4个碳原子的直链或支链烷氧基,卤素,硝基和乙酰基,或表示芳烷氧基,其中芳基部分带6-12个碳原子,烷基部分为带1-6个碳原子的直链或支链烷基,可以是未取代的,或者被相同的或不相同的1个至5个取代基所取代,所述取代基选自下列基团,即带1-4个碳原子的直链或支链的烷基和烷氧基,卤素,硝基和乙酰基,或表示环烷氧基,其中环烷基部分带5-7个碳原子,可以是未取代的,或者是被相同的或不相同的1个至5个取代基所取代,所述取代基选自下列基团,即带1-4个碳原子的直链或支链烷基,或表示带5-8元环的饱和的或部分或全部不饱和的杂环基,可含有1-3个杂原子,并可以是未取代的,或者是被相同的或不相同的1个至3个取代基所取代,所述取代基选自带1-4个碳原子的直链或支链烷基;
R1表示氢,卤素,带1-6个碳原子的直链或支链烷基,或带1-6个碳原子的直链或支链烷氧基,
R2表示氢,或带1-6个碳原子的直链或支链烷基,或表示带1-6个碳原子和1-9个相同或不同卤原子的直链或支链的卤代烷基,
R3表示氢或卤素
R4表示卤素,以及
R5表示氢或卤素。
3、按权利要求1的苯甲醛肟衍生物及其异构体或异构体的混合物,其中式(Ⅰ)中,
R表示带1-4个碳原子的直链或支链烷基,或表示带1-4个碳原子的直链或支链烷氧基,或表示卤代烷基或卤代烷氧基,在各种情况下,其中在直链或支链的卤代烷基中带1-4个碳原子,及带1-5个相同的或不相同的卤原子,或表示带2-5个碳原子的直链或支链的链烯氧基,或表示苯基或苯氧基,可以是未取代的,或在各情况下被1个至5个相同的或不相同的取代基所取代,所述取代基选自带1-3个碳原子的直链或支链烷基,带1-3个碳原子的直链或支链烷氧基,卤素,硝基和乙酰基,或表示苄氧基,苯乙基氧基或苯丙基氧基,可以是未取代的,或者是被相同的或者不相同的1个至3个取代基所取代,所述取代基选自带1-3个碳原子的直链或支链烷基和烷氧基,卤素,硝基和乙酰基,或表示环烷氧基,其中环烷基部分带5-7个碳原子,可以是未取代的,或者是被相同的或不相同的1个至3个取代基所取代,所述取代基选自带1-3个碳原子的直链或支链烷基,或表示带5-7元环的饱和的或部分或全部不饱和的杂环基,可含有1-2个硫,氮和/或氧原子,可以是未取代的,或被带1-3个碳原子的直链或支链烷基单取代;
R1表示氢,卤素,带1-4个碳原子的直链或支链烷基,或带1-4个碳原子的直链或支链烷氧基,
R2表示氢或带1-4个碳原子的直链或支链烷基,或表示带1-4个碳原子和1-5个相同或不相同卤原子的直链或支链卤代烷基,
R3表示氢或卤素,
R4表示卤素,以及
R5表示氢或卤素。
4、按权利要求1的苯甲醛肟衍生物及其异构体或其异构体的混合物,其中式(Ⅰ)中,
R表示带1-6个碳原子的直链或支链烷基,或表示带1-6个碳原子的直链或支链烷氧基,或表示卤代烷基或卤代烷氧基,在各种情况下,其中在卤代烷基中带1或2个碳原子,及带1-4个相同的或不相同的卤原子,或表示带2-3个碳原子的直链或支链的链烯氧基,或表示苯基或苯氧基,可以是未取代的,或者是在各种情况下被相同的或不相同的一个或2个取代基所取代,所述取代基选自带1或2个碳原子的烷基,带1或2个碳原子的烷氧基,卤素,硝基和乙酰基,或表示苄基,可以是未取代的,或者被相同的或不相同的1个至3个取代基所取代,所述取代基选自带1或2个碳原子的烷基、烷氧基和卤素,或表示环烷氧基,其中环烷基部分带5-6个碳原子,可以是未取代的,或是被相同的或不相同的1个至3个取代基所取代,所述取代基选自带1或2个碳原子的烷基,或表示带5-6元环的不饱和杂环基,可含有氮原子和/或硫原子,可以是未被取代的,或是被相同的或不相同的1个或2个取代基所取代,所述取代基选自带1或2个碳原子的烷基;
R1表示氢,卤素,带1或2个碳原子的烷基或带1或2个碳原子的烷氧基,
R2表示氢或带1或2个碳原子的烷基,或表示带1或2个碳原子和1-3个相同的或不相同的卤原子的卤代烷基,
R3表示氢或卤素,
R4表示卤素,以及
R5表示氢或卤素。
5、按权利要求1的苯甲醛肟衍生物及其异构体或其异构体混合物,其中式(Ⅰ)中,
R表示甲基,乙基,甲氧基,乙氧基,正丙氧基,异丙氧基,异丁氧基,烯丙氧基,2,2,2-三氯乙氧基,苄氧基,氯代甲基,苯基,2-6二氯苯基,2-4-二氯苯基,苯氧基,噻吩基或环己氧基,
R1表示氢,氟,氯,甲基或甲氧基,
R2表示氢或三氟甲基,
R3表示氢,氟或氯,
R4表示氟或氯,以及
R5表示氢或氯。
6、制备通式(Ⅰ)所示的苯甲醛肟衍生物及其异构体或异构体混合物的方法,式(Ⅰ)中,
R表示烷基,烷氧基,卤代烷基,卤代烷氧基或链烯氧基,或芳基或芳氧基,在各种情况下,可选择性地被相同的或不相同的一个或多个取代基所取代,或芳烷氧基,其中芳基可选择性地被相同的或不相同的一个或多个取代基所取代,或表示环烷氧基,该基团可选择性地被相同的或不相同的一个或多个取代基所取代,或表示杂环基,该基团可选择性地被相同的或不相同的一个或多个取代基所取代,
R1表示氢,卤素,烷基或烷氧基,
R2表示氢,烷基或卤代烷基,
R3表示氢或卤素,
R4表示卤素,以及
R5表示氢或卤素,
该方法的特征在于,将通式(Ⅱ)所示的苯基磺酰基-苯甲醛肟与通式(Ⅲ)所示的碳酰化合物反应,需要时反应在溶剂或稀释剂存在下进行,并且需要时,可在酸结合剂存在的情形下进行,
式(Ⅱ)中R1,R2,R3,R4,R5如以上所定义,
式(Ⅲ)中R如上述定义,X表示卤原子,或表示-O-COR基,其中R如上述定义。
7、用于防治害虫的药剂,其特征在于其中包括至少一种按权利要求1和6的式(Ⅰ)苯甲醛肟衍生物。
8、按权利要求1和6的式(Ⅰ)苯甲醛肟衍生物应用于防治害虫。
9、防治害虫的方法,其特征在于,将按权利要求1和6的式(Ⅰ)苯甲醛衍生物作用于害虫和/或其周围环镜。
10、用于防治害虫的药剂的制备方法,其特征在于,将按权利要求1和6的式(Ⅰ)苯甲醛肟衍生物与增充剂和/或表面活性剂混合。
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DEP3708320.1 | 1987-03-14 | ||
DE19873708320 DE3708320A1 (de) | 1987-03-14 | 1987-03-14 | Benzaldoxim-derivate |
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DE3712631A1 (de) * | 1987-04-14 | 1988-10-27 | Bayer Ag | (alpha)-methylsulfonyl-benzaldoxim-derivate |
WO1992003050A1 (en) * | 1990-08-16 | 1992-03-05 | E.I. Du Pont De Nemours And Company | Fungicidal sulfoneoxime esters |
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US3903303A (en) * | 1970-07-06 | 1975-09-02 | Stauffer Chemical Co | Controlling fungi and bacteria with certain oxime esters |
US4052194A (en) * | 1974-01-24 | 1977-10-04 | Merrill Wilcox | Oxime abscission agents |
IT1110460B (it) * | 1977-03-02 | 1985-12-23 | Ciba Geigy Ag | Prodotti che favoriscono la crescita delle piante e prodotti che proteggono le piante a base di eteri di ossime e di esteri di ossime loro preparazione e loro impiego |
US4278613A (en) * | 1978-08-28 | 1981-07-14 | Ciba-Geigy Corporation | Sulfur-containing oxime compounds, processes for producing them, and their use for protecting cultivated plants |
US4566901A (en) * | 1982-05-06 | 1986-01-28 | Ciba-Geigy Corporation | Novel oxime ethers, the preparation thereof, compositions containing them and the use thereof |
HU196288B (en) * | 1985-06-04 | 1988-11-28 | Egyt Gyogyszervegyeszeti Gyar | Fungicides containing as active substance new derivatives of fenantren and process for production of the active substance |
DE3520943A1 (de) * | 1985-06-12 | 1986-12-18 | Bayer Ag, 5090 Leverkusen | Benzaldoxim-carbamat-derivate |
US4747678A (en) | 1986-12-17 | 1988-05-31 | The Perkin-Elmer Corporation | Optical relay system with magnification |
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- 1988-03-10 US US07/166,335 patent/US4886832A/en not_active Expired - Fee Related
- 1988-03-11 KR KR1019880002514A patent/KR880011092A/ko not_active Application Discontinuation
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