CN112079800B - 被取代的烯胺羰基化合物及其制备方法和应用 - Google Patents
被取代的烯胺羰基化合物及其制备方法和应用 Download PDFInfo
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- CN112079800B CN112079800B CN201910514297.6A CN201910514297A CN112079800B CN 112079800 B CN112079800 B CN 112079800B CN 201910514297 A CN201910514297 A CN 201910514297A CN 112079800 B CN112079800 B CN 112079800B
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- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
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- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
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- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-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
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three 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
- C07D307/66—Nitrogen atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—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
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Abstract
本发明涉及一种被取代的烯胺羰基化合物及其制备方法和应用;具体地,本发明涉及式(I)所示的被取代的烯胺羰基化合物或式(I)所示被取代的烯胺羰基化合物的立体异构体、氮氧化物及其盐,及被取代的烯胺羰基化合物的制备方法,及它们在农业中作为杀虫剂的用途,及其杀虫剂组合物的形式,以及用这些化合物或组合物来防治害虫的方法;其中,环A、R1、R2、R3、R4、B、B1、B2、X、X1和n具有本发明所述的含义。
Description
技术领域
本发明涉及新的被取代的烯胺羰基化合物、其制备方法及其在农业或园艺中作为有害害虫防治剂的应用。
背景技术
已知被取代的烯胺羰基化合物可以用于杀灭害虫(参见EP 0539588、CN101466705和CN101454316),本发明的目的之一为提供一种新的用于杀灭害虫的被取代的烯胺羰基化合物。
发明内容
具体地,
一方面,本发明提供一种化合物,其为具有式(I)所示的化合物或式(I)所示的化合物的立体异构体、氮氧化物及其盐:
其中,
R1为氢、C1-6烷基、卤代C1-6烷基、C1-6烷氧基、卤代C1-6烷氧基、C2-6烯基、卤代C2-6烯基、C2-6炔基、卤代C2-6炔基、C3-6环烷基、卤代C3-6环烷基、C3-6环烷基-C1-3烷基、卤代C3-6环烷基-C1-3烷基、-C(=O)Ra、-C(=O)ORb、-C(=O)NRcRd或-S(=O)2Re;
Ra、Rb和Re各自独立地为C1-6烷基;
Rc和Rd各自独立地为氢或C1-6烷基;
R2和R3各自独立地为氢、卤素、羟基、巯基、氰基、硝基、C1-6烷基、卤代C1-6烷基、C1-6烷氧基、卤代C1-6烷氧基、C2-6烯基、C2-6炔基、C3-6环烷基或C3-6环烷基-C1-3烷基;
环A为苯基或5-6元杂芳基;
n为0、1、2、3、4、5、6或7;
各R4独立地为卤素、羟基、巯基、氰基、硝基、C1-6烷基、卤代C1-6烷基、C1-6烷氧基或卤代C1-6烷氧基;
X和X1各自独立地为O或S;
B为-CH2-;其中,B任选地被1或2个选自Rx的取代基取代;
B1为键、-CH2-或-CH2CH2-;其中,B1任选地被1、2、3或4个选自Ry的取代基取代;
B2为CRz或N;
Rx和Ry各自独立地为卤素、羟基、巯基、硝基、氰基或C1-6烷基;
Rz为氢或C1-6烷基。
在一些实施方案中,为萘基、苯并5元杂芳基或苯并6元杂芳基。
还在一些实施方案中,中的环A为苯基、噻吩、吡咯、呋喃、异噁唑、噁唑、噻唑、咪唑、吡唑或吡啶。
在另一些实施方案中,为以下子结构式:
在一些实施方案中,n为0、1、2、3、4、5、6或7;
各R4独立地为卤素、羟基、巯基、氰基、硝基、C1-4烷基、卤代C1-4烷基、C1-4烷氧基或卤代C1-4烷氧基。
还在一些实施方案中,其中,n为0、1、2、3、4、5、6或7;
各R4独立地为氟、氯、溴、碘、羟基、巯基、氰基、硝基、-CH3、-CH2CH3、-CH2CH2CH3、-CH(CH3)2、-CH2CH2CH2CH3、-C(CH3)3、-CF3、-OCH3、-OCH2CH3、-OCH2CH2CH3、-OCH(CH3)2、-OC(CH3)3或-OCF3。
在一些实施方案中,为以下子结构式:
其中,n和R4具有本发明所述的含义。
结构式中,/>表示/>基团可以通过该基团中任意合适的位置与-CR2R3-中的碳原子进行连接,如当/>为/>时,表示/>基团可以通过如下连接方式与-CR2R3-中的碳原子进行连接:
结构式中,/>表示为/>基团上的n个氢原子被R4取代,其中当n≥2,各R4相同或不同,如当/>为/>时,当n为0时,/>为当n为1时,/>为
在另一些实施方案中,为以下子结构式:
在一些实施方案中,R1为氢、C1-4烷基、卤代C1-4烷基、C1-4烷氧基、卤代C1-4烷氧基、C2-4烯基、卤代C2-4烯基、C2-4炔基、卤代C2-4炔基、C3-6环烷基、卤代C3-6环烷基、C3-6环烷基-C1-3烷基或卤代C3-6环烷基-C1-3烷基。
在另一些实施方案中,R1为氢、-CH3、-CH2CH3、-CH2CH2CH3、-CH(CH3)2、-CH2CH2CH2CH3、-C(CH3)3、-CHF2、-CF3、-CH2CHF2、-CH2CH2CH2F或-CH2CH=CCl2。
在一些实施方案中,R2和R3各自独立地为氢、卤素、羟基、巯基、氰基、硝基、C1-4烷基、卤代C1-4烷基、C1-4烷氧基、卤代C1-4烷氧基、C2-4烯基、C2-4炔基、C3-6环烷基或C3-6环烷基-C1-3烷基。
在另一些实施方案中,R2和R3各自独立地为氢、卤素、羟基、巯基、氰基、硝基、-CH3、-CH2CH3、-CH2CH2CH3、-CH(CH3)2、-CH2CH2CH2CH3或-C(CH3)3。
在一些实施方案中,X为O。
在一些实施方案中,X1为O或S。
在一些实施方案中,B为-CH2-。
在一些实施方案中,B1为键、-CH2-或-CH2CH2-。
在另一些实施方案中,B1为键。
在一些实施方案中,B2为CRz或N;
Rz为氢或C1-4烷基。
在另一些实施方案中,B2为CH或N。
在一些实施方案中,本发明提供一种化合物,其为具有式(II)所示的化合物或式(II)所示化合物的立体异构体、氮氧化物及其盐:
其中环A、n和R4具有本发明所述的含义。
还在一些实施方案中,本发明提供一种化合物,其为具有下列之一结构的化合物或具有下列之一结构化合物的立体异构体、氮氧化物及其盐:
一方面,本发明提供一种组合物,其包含本发明所述的化合物。
进一步地,本发明所述的组合物包含农药学上可接受的辅料。
再进一步地,本发明所述农药学上可接受的辅料为表面活性剂和/或载体。
另一方面,本发明提供本发明所述的化合物或本发明所述的组合物在防治农业害虫中的应用。
又另一方面,本发明提供本发明所述的化合物或本发明所述的组合物防治农业害虫的方法。
本发明的详细说明
定义和一般术语
现在详细描述本发明的某些实施方案,其实例由随附的结构式和化学式说明。本发明意图涵盖所有的替代、修改和等同技术方案,它们均包括在如权利要求定义的本发明范围内。本领域技术人员应认识到,许多与本发明所述类似或等同的方法和材料能够用于实践本发明。本发明绝不限于本发明所述的方法和材料。在所结合的文献、专利和类似材料的一篇或多篇与本申请不同或相矛盾的情况下(包括但不限于所定义的术语、术语应用、所描述的技术,等等),以本申请为准。
应进一步认识到,本发明的某些特征,为清楚可见,在多个独立的实施方案中进行了描述,但也可以在单个实施例中以组合形式提供。反之,本发明的各种特征,为简洁起见,在单个实施方案中进行了描述,但也可以单独或以任意适合的子组合提供。
除非另外说明,本发明所使用的所有科技术语具有与本发明所属领域技术人员的通常理解相同的含义。本发明涉及的所有专利和公开出版物通过引用方式整体并入本发明。
除非另外说明,应当应用本发明所使用的下列定义。出于本发明的目的,化学元素与元素周期表CAS版,和《化学和物理手册》,第75版,1994一致。此外,有机化学一般原理可参考"Organic Chemistry",Thomas Sorrell,University Science Books,Sausalito:1999,和"March's Advanced Organic Chemistry"by Michael B.Smith and JerryMarch,John Wiley&Sons,New York:2007中的描述,其全部内容通过引用并入本发明。
除非另有说明或者上下文中有明显的冲突,本发明所使用的冠词“一”、“一个(种)”和“所述”旨在包括“至少一个”或“一个或多个”。因此,本发明所使用的这些冠词是指一个或多于一个(即至少一个)宾语的冠词。例如,“一组分”指一个或多个组分,即可能有多于一个的组分被考虑在所述实施方案的实施方式中采用或使用。
术语“包含”为开放式表达,即包括本发明所指明的内容,但并不排除其他方面的内容。
“立体异构体”是指具有相同化学构造,但原子或基团在空间上排列方式不同的化合物。立体异构体包括对映异构体、非对映异构体、构象异构体(旋转异构体)、几何异构体(顺/反)异构体、阻转异构体,等等。
“对映异构体”是指一个化合物的两个不能重叠但互成镜像关系的异构体。
“非对映异构体”是指有两个或多个手性中性并且其分子不互为镜像的立体异构体。非对映异构体具有不同的物理性质,如熔点、沸点、光谱性质和反应性。非对映异构体混合物可通过高分辨分析操作如电泳和色谱,例如HPLC来分离。
本发明所使用的立体化学定义和规则一般遵循S.P.Parker,Ed.,McGraw-HillDictionary of Chemical Terms(1984)McGraw-Hill Book Company,New York;andEliel,E.and Wilen,S.,“Stereochemistry of Organic Compounds”,John Wiley&Sons,Inc.,New York,1994中的描述。
许多有机化合物以光学活性形式存在,即它们具有使平面偏振光的平面发生旋转的能力。在描述光学活性化合物时,使用前缀D和L或R和S来表示分子关于其一个或多个手性中心的绝对构型。前缀d和l或(+)和(-)是用于指定化合物所致平面偏振光旋转的符号,其中(-)或l表示化合物是左旋的。前缀为(+)或d的化合物是右旋的。一种具体的立体异构体是对映异构体,这种异构体的混合物称作对映异构体混合物。对映异构体的50:50混合物称为外消旋混合物或外消旋体,当在化学反应或过程中没有立体选择性或立体特异性时,可出现这种情况。
本发明公开化合物的任何不对称原子(例如,碳等)都可以以外消旋或对映体富集的形式存在,例如(R)-、(S)-或(R,S)-构型形式存在。在某些实施方案中,各不对称原子在(R)-或(S)-构型方面具有至少50%对映体过量,至少60%对映体过量,至少70%对映体过量,至少80%对映体过量,至少90%对映体过量,至少95%对映体过量,或至少99%对映体过量。
依据起始物料和方法的选择,本发明化合物可以以可能的异构体中的一个或它们的混合物,例如外消旋体和非对应异构体混合物(这取决于不对称碳原子的数量)的形式存在。光学活性的(R)-或(S)-异构体可使用手性合成子或手性试剂制备,或使用常规技术拆分。如果化合物含有一个双键,取代基可能为E或Z构型;如果化合物中含有二取代的环烷基,环烷基的取代基可能有顺式或反式构型。
所得的任何立体异构体的混合物可以依据组分物理化学性质上的差异被分离成纯的或基本纯的几何异构体,对映异构体,非对映异构体,例如,通过色谱法和/或分步结晶法。
可以用已知的方法将任何所得终产物或中间体的外消旋体通过本领域技术人员熟悉的方法拆分成光学对映体,如,通过对获得的其非对映异构的盐进行分离。外消旋的产物也可以通过手性色谱来分离,如,使用手性吸附剂的高效液相色谱(HPLC)。特别地,对映异构体可以通过不对称合成制备。
像本发明所描述的,本发明的化合物可以任选地被一个或多个取代基所取代,如上面的通式化合物,或者像实施例里面特殊的例子,子类,和本发明所包含的一类化合物。应了解“任选取代的”这个术语与“取代或非取代的”这个术语可以交换使用。一般而言,术语“取代的”表示所给结构中的一个或多个氢原子被具体取代基所取代。除非其他方面表明,一个任选的取代基团可以在基团各个可取代的位置进行取代。当所给出的结构式中不只一个位置能被选自具体基团的一个或多个取代基所取代,那么取代基可以相同或不同地在各个位置取代。具体地,“一个或多个”的实例是指1、2、3、4、5、6、7、8、9或10个。其中所述的取代基可以是,但并不限于,氘,氟,氯,溴,碘,氰基,羟基,硝基,氨基,羧基,烷基,烷氧基,烷氧基烷基,烷氧基烷氧基,烷氧基烷氨基,芳氧基,杂芳基氧基,杂环基氧基,芳基烷氧基,杂芳基烷氧基,杂环基烷氧基,环烷基烷氧基,烷氨基,烷氨基烷基,烷氨基烷氨基,环烷基氨基,环烷基烷氨基,烷硫基,卤代烷基,卤代烷氧基,羟基取代的烷基,羟基取代的烷氨基,氰基取代的烷基,氰基取代的烷氧基,氰基取代的烷氨基,氨基取代的烷基,烷基酰基,杂烷基,环烷基,环烯基,环烷基烷基,杂环基,杂环基烷基,杂环基酰基,芳基,芳基烷基,芳氨基,杂芳基,杂芳基烷基,杂芳基氨基,酰胺基,磺酰基,氨基磺酰基等等。
另外,需要说明的是,除非以其他方式明确指出,在本发明中所采用的描述方式“各…独立地为”与“…各自独立地为”和“…独立地为”可以互换,均应做广义理解,其既可以是指在不同基团中,相同符号之间所表达的具体选项之间互相不影响,也可以表示在相同的基团中,相同符号之间所表达的具体选项之间互相不影响。
在本说明书的各部分,本发明公开化合物的取代基按照基团种类或范围公开。特别指出,本发明包括这些基团种类和范围的各个成员的每一个独立的次级组合。例如,术语“C1-C6烷基”或“C1-6烷基”特别指独立公开的甲基、乙基、C3烷基、C4烷基、C5烷基和C6烷基。
本发明使用的术语“烷基”或“烷基基团”,表示含有1至20个碳原子,饱和的直链或支链一价烃基基团;其中所述烷基基团任选地被一个或多个本发明描述的取代基所取代。除非另外详细说明,烷基基团含有1-20个碳原子。在一实施方案中,烷基基团含有1-12个碳原子;在一实施方案中,烷基基团含有1-8个碳原子;在另一实施方案中,烷基基团含有1-6个碳原子;在又一实施方案中,烷基基团含有1-4个碳原子;还在一实施方案中,烷基基团含有1-3个碳原子。
烷基基团的实例包含,但并不限于,甲基(Me、-CH3),乙基(Et、-CH2CH3),正丙基(n-Pr、-CH2CH2CH3),异丙基(i-Pr、-CH(CH3)2),正丁基(n-Bu、-CH2CH2CH2CH3),异丁基(i-Bu、-CH2CH(CH3)2),仲丁基(s-Bu、-CH(CH3)CH2CH3),叔丁基(t-Bu、-C(CH3)3),正戊基(-CH2CH2CH2CH2CH3),2-戊基(-CH(CH3)CH2CH2CH3),3-戊基(-CH(CH2CH3)2),2-甲基-2-丁基(-C(CH3)2CH2CH3),3-甲基-2-丁基(-CH(CH3)CH(CH3)2),3-甲基-1-丁基(-CH2CH2CH(CH3)2),2-甲基-1-丁基(-CH2CH(CH3)CH2CH3),等等。
术语“烯基”表示含有2-12个碳原子的直链或支链一价烃基,其中至少有一个不饱和位点,即有一个碳-碳sp2双键,其中,所述烯基基团可以任选地被一个或多个本发明所描述的取代基所取代,其包括“cis”和“tans”的定位,或者“E”和“Z”的定位。在一实施方案中,烯基基团包含2-8个碳原子;在另一实施方案中,烯基基团包含2-6个碳原子;在又一实施方案中,烯基基团包含2-4个碳原子。烯基基团的实例包括,但并不限于,乙烯基(-CH=CH2),烯丙基(-CH2CH=CH2),丙烯基(CH3-CH=CH-),氧代的丁烯基(CH3-C(=O)-CH=CH-)等等。
术语“炔基”表示含有2-12个碳原子的直链或支链一价烃基,其中至少有一个碳-碳sp三键,其中,所述炔基基团可以任选地被一个或多个本发明所描述的取代基所取代。在一实施方案中,炔基基团包含2-10个碳原子;在一实施方案中,炔基基团包含2-8个碳原子;在另一实施方案中,炔基基团包含2-6个碳原子;在又一实施方案中,炔基基团包含2-4个碳原子。炔基基团的实例包括,但并不限于,-C≡CH、-C≡CCH3、-CH2-C≡CH、-CH2-C≡CCH3、-CH2CH2-C≡CH、-CH2-C≡CCH2CH3、-CH2CH2-C≡CH2CH3等等。
术语“烷氧基”表示烷基基团通过氧原子与分子其余部分相连,其中烷基基团具有如本发明所述的含义。烷氧基基团的实例包括,但并不限于,甲氧基(MeO、-OCH3),乙氧基(EtO、-OCH2CH3),1-丙氧基(n-PrO、n-丙氧基、-OCH2CH2CH3),2-丙氧基(i-PrO、i-丙氧基、-OCH(CH3)2)等等。
术语“环烷基”表示含有3-12个碳原子的,单价或多价的饱和单环、双环或三环体系。在一实施方案中,环烷基包含3-10个碳原子;在另一实施方案中,环烷基包含3-8个碳原子;在又一实施方案中,环烷基包含3-6个碳原子。所述环烷基基团任选地被一个或多个本发明所描述的取代基所取代。这样的实例包括,但并不限于,环丙基,环丁基,环戊基,环己基,环庚基,环辛基,环壬基,环癸基,环十一烷基,环十二烷基,等等。
术语“环烷基-烷基”表示烷基基团被一个或多个环烷基基团所取代,其中烷基和环烷基基团具有如本发明所述的含义。
术语“杂原子”是指O、S、N、P和Si,包括N、S和P任何氧化态的形式;伯、仲、叔胺和季铵盐的形式;或者杂环中氮原子上的氢被取代的形式,例如,N(像3,4-二氢-2H-吡咯基中的N),NH(像吡咯烷基中的NH)或NR(像N-取代的吡咯烷基中的NR)。
术语“卤素”是指氟(F)、氯(Cl)、溴(Br)或碘(I)。
术语“杂芳基”表示含有5-12个环原子,或5-10个环原子,或5-6个环原子的单环、双环和三环体系,其中至少一个环体系是芳香族的,且至少一个环体系包含一个或多个杂原子,其中每一个环体系包含5-7个原子组成的环,且有一个或多个附着点与分子其余部分相连。术语“杂芳基”可以与术语“杂芳环”或“杂芳族化合物”交换使用。所述杂芳基基团任选地被一个或多个本发明所描述的取代基所取代。在一实施方案中,5-10个原子组成的杂芳基包含1,2,3或4个独立选自O,S和N的杂原子。
杂芳基基团的实例包括,但并不限于,2-呋喃基,3-呋喃基,N-咪唑基,2-咪唑基,4-咪唑基,5-咪唑基,3-异噁唑基,4-异噁唑基,5-异噁唑基,2-噁唑基,4-噁唑基,5-噁唑基,N-吡咯基,2-吡咯基,3-吡咯基,2-吡啶基,3-吡啶基,4-吡啶基,2-嘧啶基,4-嘧啶基,5-嘧啶基,哒嗪基(如3-哒嗪基),2-噻唑基,4-噻唑基,5-噻唑基,四唑基(如5-四唑基),三唑基(如2-三唑基和5-三唑基),2-噻吩基,3-噻吩基,吡唑基,异噻唑基,1,2,3-噁二唑基,1,2,5-噁二唑基,1,2,4-噁二唑基,1,2,3-三唑基,1,2,3-硫代二唑基,1,3,4-硫代二唑基,1,2,5-硫代二唑基,吡嗪基,1,3,5-三嗪基,嘧啶酮基,吡啶酮基;也包括以下的双环,但绝不限于这些双环:苯并咪唑基,苯并呋喃基,苯并四氢呋喃基,苯并噻吩基,吲哚基(如2-吲哚基),苯并哌啶基,等等。
术语“卤代烷基”表示烷基基团被一个或多个卤素原子所取代,这样的实例包含,但并不限于,-CF3,-CHF2,-CH2Cl,-CH2CF3,-CH2CHF2,-CH2CH2CF3等。
术语“卤代烷氧基”表示烷氧基基团被一个或多个卤素原子所取代,这样的实例包含,但并不限于,-OCF3,-OCHF2,-OCHCl2,-OCH2CHF2,-OCH2CHCl2,-OCH(CH3)CHF2等。
术语“卤代环烷基-烷基”表示“环烷基-烷基”基团被一个或多个卤素原子所取代。
术语“卤代烯基”表示烯基基团被一个或多个卤素原子所取代。
术语“卤代炔基”表示炔基基团被一个或多个卤素原子所取代。
术语“卤代环烷基”表示环烷基基团被一个或多个卤素原子所取代。
术语“巯基”是指-SH。
本发明所述化合物的盐,包括衍生自碱金属或碱土金属的那些以及衍生自氨和胺的那些。优选的阳离子包括钠、钾、镁以及具有化学式N+(RAARBBRCCRDD)的铵阳离子,其中RAA、RBB、RCC和RDD独立地选自氢、C1-C6烷基和C1-C6羟基烷基。具有式(I)或式(II)的化合物的盐可以通过用金属氢氧化物(例如氢氧化钠)或胺(例如氨、三甲胺、二乙醇胺、2-甲硫基丙胺、双烯丙基胺、2-丁氧基乙胺、吗啉、环十二胺或苄胺)对具有式(I)或式(II)的化合物进行处理来制备。
当本发明的化合物包含一个碱部分时,可接受的盐可以由有机酸和无机酸形成,例如乙酸、丙酸、乳酸、柠檬酸、酒石酸、琥珀酸、富马酸、马来酸、丙二酸、扁桃酸、苹果酸、邻苯二甲酸、盐酸、氢溴酸、磷酸、硝酸、硫酸、甲磺酸、萘磺酸、苯磺酸、甲苯磺酸、樟脑磺酸以及类似地已知可接受的酸。
本发明化合物的组合物和制剂
本发明的化合物一般可用作组合物即制剂中的杀虫剂活性成分,通常还包括农药学上可接受的表面活性剂和/或载体。
上述表面活性剂可以为农药剂型领域所公知的各种表面活性剂,本发明优选为乳化剂、分散剂和润湿剂中的一种或多种。
除上述表面活性剂外的其它载体可以为农药剂型领域所公知的各种载体,包括各种硅酸盐类、碳酸盐类、硫酸盐类、氧化物类、磷酸盐类、植物载体类、合成载体类。具体地,例如:白炭黑、高岭土、硅藻土、粘土、滑石、有机膨润土、浮石、二氧化钛、糊精、纤维素粉、轻质碳酸钙、可溶性淀粉、玉米淀粉、锯末粉、尿素、胺肥、尿素和胺肥的混合物、葡萄糖、麦芽糖、蔗糖、无水碳酸钾、无水碳酸钠、无水碳酸氢钾、无水碳酸氢钠、凹凸棒土、无水碳酸钾与无水碳酸氢钾的混合物和无水碳酸钠与无水碳酸氢钠的混合物中的一种或多种。
上述乳化剂可以为农药剂型领域所公知的各种乳化剂,具体地,该乳化剂可以为十二烷基苯磺酸钙、三苯乙基酚聚氧乙烯醚磷酸酯、脂肪醇聚氧乙烯醚、烷基酚聚氧乙烯醚、烷基酚聚氧乙烯聚氧丙烯醚、脂肪胺、脂肪酰胺的环氧乙烷加成物、脂肪酸聚氧乙烯酯、松香酸环氧乙烷加成物、多元醇脂肪酸酯及其环氧乙烷加成物、苯乙烯基苯基聚氧乙烯醚、烷基酚甲醛树脂聚氧乙烯醚、端羟基聚氧乙烯聚氧丙烯醚、苯乙烯基苯酚甲醛树脂聚氧乙烯聚氧丙烯醚和蓖麻油聚氧乙烯醚中的一种或多种。
上述分散剂可以为农药剂型领域所公知的各种分散剂,具体地,该分散剂为丙烯酸均聚物钠盐、马来酸二钠盐、萘磺酸甲醛缩合物钠盐、松香嵌段聚氧乙烯醚聚氧丙烯醚磺酸盐、端羟基聚氧乙烯聚氧丙烯醚嵌段共聚物、三苯乙基酚聚氧乙烯醚磷酸酯、脂肪醇聚氧乙烯醚磷酸酯和对羟苯基木质素磺酸钠盐中的一种或多种。
上述润湿剂可以为农药剂型领域所公知的各种润湿剂,具体地,该润湿剂可以为十二烷基硫酸钠、仲烷基硫酸钠、十二烷基苯磺酸钠、脂肪醇聚氧乙烯醚、烷基萘磺酸盐、烷基酚树脂聚氧乙烯醚硫酸盐中的一种或多种。
根据本发明的杀虫剂组合物,该杀虫剂组合物还可以含有农药剂型领域所常用的各种制剂用助剂,具体地,该制剂用助剂可以为溶剂、助溶剂、增稠剂、防冻剂、囊材、保护剂、消泡剂、崩解剂、稳定剂、防腐剂和粘结剂中的一种或多种。
上述溶剂可以为农药剂型领域所公知的各种溶剂,具体地,该溶剂可以为有机溶剂、植物油、矿物油、溶剂油和水中的一种或多种。
其中,所述有机溶剂包括N-甲基吡咯烷酮、四氢呋喃、二甲基亚砜、N,N-二甲基癸酰胺、N,N-二甲基甲酰胺、三甲苯、四甲苯、二甲苯、甲苯、辛烷、庚烷、甲醇,异丙醇、正丁醇、四氢糠醇、磷酸三丁酯、1,4-二氧六环和环己酮中的一种或多种。
所述植物油包括甲基化植物油,松脂基植物油,松节油,环氧大豆油、大豆油、花生油、菜籽油、蓖麻油、玉米油和松籽油中的一种或多种。
所述矿物油包括液蜡、机油、煤油和润滑油中的一种或多种。
同时,上述溶剂也可以作为助溶剂使用。
上述防冻剂可以为农药剂型领域所公知的各种防冻剂,本发明优选为乙二醇、丙二醇、甘油和尿素中的一种或多种。
上述增稠剂可以为农药剂型领域所公知的各种增稠剂,具体地,该增稠剂可以为黄原胶、聚乙烯醇、聚丙烯醇、聚乙二醇、白炭黑、硅藻土、高岭土、粘土、海藻酸钠、硅酸铝镁、硅酸铝钠、羧甲基纤维素、羟丙基纤维素钠和有机膨润土中的一种或多种。
上述囊材可以为农药剂型领域所公知的各种囊材,本发明优选为聚氨酯、聚脲和脲醛树脂中的一种或多种。
上述保护剂可以为农药剂型领域所公知的各种保护剂,本发明优选为聚乙烯醇和/或聚乙二醇。
上述消泡剂可以为农药剂型领域所公知的各种消泡剂,本发明优选为有机硅氧烷、磷酸三丁酯和硅酮中的一种或多种。
上述稳定剂选自亚磷酸三苯酯、环氧氯丙烷和醋酐中的一种或多种。
上述防腐剂选自苯甲酸、苯甲酸钠、1,2-苯并异噻唑啉-3-酮(简称BIT)、卡松和山梨酸钾中的一种或多种。
本发明还提供一种由上述杀虫剂组合物所制备的制剂,所述制剂的剂型为乳油、水乳剂、微乳剂、可溶性液剂、水悬浮剂、悬乳剂、超低容量喷雾剂、油悬浮剂、微囊悬浮剂、水面展膜油剂、可湿性粉剂、水分散性颗粒剂、干悬浮剂、可溶性粉剂、可溶性粒剂、可乳化粉剂、可乳化颗粒剂、颗粒剂、固体微胶囊制剂、泡腾片剂、泡腾颗粒剂、水漂浮分散颗粒剂或种衣剂。上述剂型均可由本领域的常规方法来制备。
上述乳油制剂的制备方法例如可以包括将各活性组分、溶剂、助溶剂及乳化剂混合搅拌使其形成均匀透明油相,即可得到乳油制剂。
上述水乳剂制备方法例如可以包括将活性成分、乳化剂、助溶剂和溶剂混合,使其成为均匀油相;将水、增稠剂、防冻剂等混合,使其成均一水相。在高速剪切下,将水相加入到油相或将油相加入到水相,形成分散性良好的水乳剂。
上述微乳剂的制备方法例如可以是将活性成分,乳化剂,溶剂混合搅拌成均一透明的油相。在搅拌的条件下,逐渐的加入水,使其形成均一透明的微乳液。
上述水/油悬浮剂的制备方法:例如可以是以水或油为介质,将活性组分、表面活性剂等助剂加入砂磨釜中,进行研磨至一定粒径后,过滤。再将计量好的增稠剂加入到研磨好的母液中,剪切分散均匀。制成油悬浮剂或水悬浮剂。
上述水分散性粒剂及可溶性粒剂的制备方法:例如可以是将各活性组分、分散剂、润湿剂、载体等混合均匀,然后通过气流粉碎至一定粒径,再加入水进行捏合,最后加入造粒机中进行造粒,干燥后即可得到水分散性粒剂或可溶性粒剂。
上述可溶性粉剂及可湿性粉剂的制备方法:例如可以是将各活性组分、各种助剂及其他载体等填料充分混合,用超细粉碎机粉碎。
本发明的杀虫剂组合物可以以成品制剂形式提供,即组合物中各物质已经混合;也可以以单独制剂形式提供,使用前在桶或罐中自行混合,并根据所需活性物质的浓度选择性地与水混合进行稀释即可。
与制剂领域相关的其他信息,参见T.S.Woods的“The Formulator’s Toolbox-Product Forms for Modern Agriculture”,Pesticide Chemistry and Bioscience,TheFood-Environment Challenge,T.Brooks和T.R.Roberts编辑,Proceedings of the 9thInternational Congress on Pesticide Chemistry,The Royal Society of Chemistry,Cambridge,1999,第120-133页。还可参见U.S.3,235,361第6栏,第16行至第7栏,第19行和实施例10-41;U.S3,309,192第5栏,第43行至第7栏,第62行和实施例8、12、15、39、41、52、53、58、132、138-140、162-164、166、167和169-182;U.S.2,891,855第3栏,第66行至第5栏,第17行和实施例1-4;Klingman的Weed Control as a Science,John Wiley and Sons,Inc.,New York,1961,第81-96页;Hance等人的Weed Control Handbook,第8版,BlackwellScientific Publications,Oxford,1989;以及Developments in formulationtechnology,PJB Publications,Richmond,UK,2000。
本发明化合物及组合物的应用
本发明化合物尤其适合防治有用植物中的动物害虫如节肢动物、腹足动物和线虫,包括但不限于:
半翅目(Hemiptera):飞虱(飞虱科(Delphacidae))如褐飞虱(Nilaparvatalugens)、小灰飞虱(Laodelphax striatellus);叶蝉(角顶叶蝉科(Deltocephalidae))如绿稻叶蝉(黑尾叶蝉(Nephotettix cincticeps));蚜虫(蚜科(Aphididae))如棉蚜(Aphisgossypii)、苜蓿蚜(Aphis craccivora Koch);蝽科(Pentatomidae)如花角绿蝽(Nezaraantennata);粉虱(Aleyrodidae)如温室粉虱(Trialeurodes vaporariorum);蚧(Coccidae)如加州红蚌质蚧(Calformia red scale)(Aonidiella aurantii);网蝽科(Tingidae);木虱(Homoptera,Psyllidea);
鳞翅目(Lepidoptera):螟蛾(Pyralidae)如二化螟(Chilo suppressalis);夜蛾(Noctuidae)如斜纹贪夜蛾(Spodoptera litura)、粘虫(Pseudaletia separata)、实夜蛾属(Heliothis spp.)和铃夜蛾属(Helicoverpa spp.);粉蝶(Pieridae)如菜粉蝶(Pierisrapae);卷蛾(Tortricidae)如褐带卷蛾属(Adoxophyes);细蛾(Gracillariidae)如茶细蛾(Caloptilia theivora)和苹果细蛾(Phyllonorycter ringoneella);蛀果蛾(Carposinidae)如桃蛀果蛾(Carposina niponensis);潜蛾(Lyonetiidae)如潜蛾属(Lyonetia spp.);毒蛾(Lymantriidae)如毒蛾属(Lymantria spp.)和黄毒蛾属(Euproctis spp.);巢蛾(Yponomeutidae)如小菜蛾(Plutella xylostella);麦蛾(Gelechiidae)如红铃麦蛾(Pectinophora gossypiella)和马铃薯麦蛾(Phthorimaeaoperculella);灯蛾(Arctiidae)如美国白蛾(Hyphantria cunea);以及谷蛾(Tineidae)如衣蛾(Tineatranslucens)和幕谷蛾(Tineola bisselliella);
缨翅目(Thysanoptera):西花蓟马(Frankliniella occidentalis)、棕榈蓟马(Thrips palmi)、黄色硬蓟马(Scirtothrips dorsalis)、烟蓟马(Thrips tabaci)、丽花蓟马(Frankliniella intonsa)和马铃薯蓟马(Frankliniella fusca);
双翅目(Diptera):家蝇(Musca domestica)、淡色库蚊(Culex popienspallens)、三膝虻(Tabanus trigonus)、葱蝇(Hylemya anitqua)、灰地种蝇(Hylemyaplatura)、中华按蚊(Anopheles sinensis)、日本稻潜蝇(Agromyza oryzae)、稻潜蝇(Hydrellia griseola)、稻秆蝇(Chlorops oryzae)、瓜寡鬃实蝇(Dacus cucurbitae)、地中海果实蝇(Ceratitis capitata)和三叶草斑潜蝇(Liriomyza trifolii);
鞘翅目(Coleoptera):茄二十八星瓢虫(Epilachna vigintioctopunctata)、黄曲条菜跳甲(Phyllotreta striolata)、水稻负泥虫(Oulema oryzae)、稻象(Echinocnemussquameus)、稻水象(Lissorhoptrus oryzophilus)、棉铃象(Anthonomus grandis)、绿豆象(Callosobruchus chinensis)、寄生谷象(Sphenophorus venatus)、日本弧丽金龟(Popillia japonica)、古铜异丽金龟(Anomala cuprea)、根萤叶甲属(Diabrotica spp.)、马铃薯叶甲(Leptinotarsa decemlineata)、叩甲属(Agriotes spp.)、烟草窃蠹(Lasioderma serricorne)、小圆皮蠹(Anthrenus verbasci)、赤拟谷盗(Triboliumcastaneum)、褐粉蠹(Lyctus brunneus)、白斑星天牛(Anoplophora malasiaca)和纵坑切梢小蠹(Tomicus piniperda);
直翅目(Orthoptera):东亚飞蝗(Locusta migratoria)、非洲蝼蛄(Gryllotalpaafficana)、北海道稻蝗(Oxya yezoensis)和日本稻蝗(Oxya japanica);
膜翅目(Hymenoptera):新疆菜叶蜂(Athalia rosae)、切叶蚁属(Acromyrmexspp.)和火蚁属(Solenopsis spp.);
线虫(Nematodes):水稻干尖线虫(Aphelenchoides besseyi)、草莓芽线虫(Nothotylenchus acris)、大豆孢囊线虫(Heterodera glycines)、南方根结线虫(Meloidogyne incognita)、短体线虫属(Pratylenchus penetrans)和异常珍珠线虫(Nacobbus aberrans);
蜚蠊目(Blattariae):德国小蠊(Blattella germanica)、黑胸大蠊(Periplanetafuliginosa)、美洲大蠊(Periplaneta Americana)、褐斑大蠊(Periplaneta brunnea)和东方蜚蠊(Blatta orientalis);
蜱螨目(Acarina):叶螨科(Tetranychidae)(例如,朱砂叶螨(Tetranychuscinnabarinus)、二斑叶螨(Tetranychusurticae)、柑橘全爪螨(Panonychus citri)和小爪螨属(Oligonychus spp.));瘿螨科(Eriophyidae)(例如,橘刺皮瘿螨(Aculopspelekassi));跗线螨科(Tarsonemidae);细须螨科(Tenuipalpidae);杜克螨科(Tuckerellidae);粉螨科(Tuckerellidae Acaridae);麦食螨科(Pyroglyphidae)(例如,粉尘螨(Dermatophagoides farinae)和屋尘螨(Dermatophagoides ptrenyssnus));肉食螨科(Cheyletidae)、马六甲肉食螨(Cheyletus malaccensis)和马六甲肉食螨(Cheyletusmoorei);以及皮刺螨科(Dermanyssidae)。
在本发明的范围内,有用植物包括以下植物种类:谷物(小麦、大麦、黑麦、燕麦、稻、玉米、高粱以及相关物种);甜菜(糖萝卜以及饲用甜菜);梨果、核果以及软水果(苹果、梨、李子、桃、扁桃、樱桃、草莓、覆盆子和黑莓);豆科植物(扁豆、宾豆、豌豆、大豆);油料作物(油菜、芥菜、橄榄、向日葵、椰子、蓖麻油植物、可可豆、落花生或大豆);瓜类植物(南瓜、黄瓜、甜瓜);纤维植物(棉花、亚麻、黄麻);柑橘属水果(桔子、柠檬、葡萄柚、柑橘);蔬菜(菠菜、莴苣、芦笋、甘蓝、胡萝卜、洋葱、番茄、马铃薯、红椒);月桂类植物(鳄梨、樟属、樟脑)或植物,例如烟草、坚果、咖啡、茄子、甘蔗、茶、胡椒、葡萄藤、啤酒花、香蕉以及天然橡胶植物,连同草皮、观赏和森林植物,例如花卉、灌木、阔叶树或常绿树,例如针叶树,以及植物繁殖材料。
术语“植物繁殖材料”应当被理解为表示该植物的生殖部分,例如种子,这些部分可以用于该植物的繁殖,以及营养性材料,例如插条或块茎(例如马铃薯)。
本发明的化合物或组合物通过有效量的活性物质可杀灭害虫。因此,本发明还涉及用于防治害虫的方法,所述方法通过将本发明的化合物或组合物施用于种子、植物或植物部位、果实或植物生长的土壤进行。施用可以在种子、植物或植物部位、果实或植物生长的土壤被害虫侵染之前和之后进行。
所用术语“有效量”表示足以在栽培植物上或在材料保护中防治害虫且不对被处理植物引起显著损害的量的本发明化合物或组合物。该量可以在宽范围内变化且取决于各种因素如害虫品种、被处理的栽培植物或材料、气候条件以及所用具体化合物。
本发明化合物或组合物使用方法简单,将本发明化合物或组合物施于所述的害虫或其生长介质上。本发明化合物或组合物的施用剂量根据天气条件、剂型、施用时机、施用方法、施用面积、目标病害、目标作物等变化。
一般合成过程
下述方案描述本发明化合物的制备。除非有进一步的说明,本发明的化合物可以通过本发明所描述的方法制备得到。制备本发明的化合物所使用的原料、试剂等等均是可以商购的,或者可以通过本领域常规的方法制备得到。在本说明书中,如果在化学名称和化学结构间存在任何差异,结构是占优的。另外,在一些实施方案中,如无特殊说明,本发明所述的反应是在室温下进行,其中室温为0~35℃。
本发明核磁共振氢谱的测试条件是:室温条件下,布鲁克(Bruker)400MHz或600MHz的核磁仪,以CDC13,d6-DMSO,CD3OD或d6-丙酮为溶剂(报导以ppm为单位),用TMS(0ppm)或氯仿(7.26ppm)作为参照标准。当出现多重峰的时候,将使用下面的缩写:s(singlet,单峰),d(doublet,双峰),t(triplet,三重峰),q(quartet,四重峰),m(multiplet,多重峰),br(broadened,宽峰),dd(doublet of doublets,双二重峰),dt(doublet of triplets,双三重峰)。偶合常数,用赫兹(Hz)表示。
本发明所用质谱测试条件为:低分辨率质谱(MS)数据测定的条件是:Agilent6120Quadrupole HPLC-MS(柱子型号:Zorbax SB-C18,2.1x 30mm,3.5μm,6min,流速为0.6mL/min,流动相:5%-95%(含0.1%甲酸的CH3CN)在(含0.1%甲酸的H2O)中的比例)),在210/254nm用UV检测,用电喷雾电离模式(ESI)。
合成方案
合成方案一
中间体化合物d可以通过合成方案一制备得到。化合物a与化合物b经过取代反应后得到化合物c;化合物c在甲醇钠/甲醇体系中进行分子内关环,得到中间体化合物d。
合成方案二
中间体化合物g可以通过合成方案二制备得到。化合物e与化合物f在碱性体系中进行反应得到中间体化合物g;
其中X为氟、氯、溴或碘;环A、R4和n具有本发明所述的含义。
合成方案三
目标化合物II可以通过合成方案三制备得到。中间体化合物g与中间体化合d经过加热反应,脱水、脱羧后,即可得到目标化合物II;
其中,环A、R4和n具有本发明所述的含义。
实施例
中间体O:4-(甲氧基羰基)-5-氧代-2,5-二氢呋喃-3-醇钠盐的合成
第一步:2-甲氧基-2-氧代乙基丙二酸甲酯的合成
室温下,将丙二酸单甲酯钾盐(16.24g,104mmol)溶于N,N-二甲基甲酰胺(100mL)后将其加热至35℃,而后滴加溴乙酸甲酯(15.3g,100mmol),滴加完毕后在35℃下继续搅拌8小时。反应完成后,减压蒸馏除去溶剂,加入水(100mL),用乙酸乙酯萃取(100mL x 3),合并有机相,用无水硫酸钠干燥,过滤,滤液减压浓缩后得到浅黄色油状液体18.65g,收率为98%。
第二步:4-(甲氧基羰基)-5-氧代-2,5-二氢呋喃-3-醇钠盐的合成
将2-甲氧基-2-氧代乙基丙二酸甲酯(4.0g,21.0mmol)溶于10mL甲醇中,将其加热至40℃后滴加30%甲醇钠(15mL,21mmol)甲醇溶液,滴加完毕后,将得到的混合物加热至70℃搅拌回流3小时。冷却至0℃,静置2小时,过滤,滤饼于50℃下真空干燥,得到白色固体2.47g,收率为66%。
1H NMR(400MHz,D2O)δ(ppm):3.73(s,3H),4.42(s,2H)。
实施例1:4-((2,2-二氟乙基)(萘-2-基甲基)胺)呋喃-2(5H)-酮的合成
步骤1:2,2-二氟-N-(萘-2-基甲基)乙胺的合成
将2,2-二氟乙胺(356mg,4.4mmol)溶于N,N-二甲基甲酰胺(8mL),加入碳酸钾(828mg,6mmol),室温搅拌30分钟后,滴加2-氯甲基萘(707mg,4mmol)的N,N-二甲基甲酰胺(5mL)溶液;滴加完成后,升至60℃反应12小时。反应完成后,冷却至室温,加入水(15mL),用乙酸乙酯萃取(20mL x 3),合并有机相,用洗涤饱和食盐水(20mL x 2),无水硫酸钠干燥,过滤,将滤液减压浓缩,残留物经柱层析分离[石油醚/乙酸乙酯(v:v)=10/1],得到黄色油状液体275mg,收率31.5%。
MS(ES-API,pos.ion)m/z:222.10[M+H]+。
步骤2:4-((2,2-二氟乙基)(萘-2-基甲基)胺)呋喃-2(5H)-酮的合成
在氮气保护下,将2,2-二氟-N-(萘-2-基甲基)乙胺(275mg,1.24mmol)溶于丁腈(20mL),加入丁烯酸内酯钠盐(414mg,2.29mmol),升温到65℃反应3小时。反应完成后,冷却到室温,有浅黄色固体析出,过滤出固体;将得到的浅黄色固体和硫酸氢钾(142mg,1.04mmol)溶于丁腈(15mL),在氮气保护下,升温120℃回流反应16小时。反应完成后,减压蒸除溶剂,加入20mL水,再用乙酸乙酯萃取(20mL x 3),合并有机相,无水硫酸钠干燥,过滤,将滤液减压浓缩,残留物经柱层析[石油醚/乙酸乙酯(v/v)=1/1]分离,得到白色固体140mg,收率37.2%。
1H NMR(400MHz,CDCl3)δ7.90(s,1H),7.87(s,1H),7.86-7.80(m,2H),7.62(s,1H),7.58-7.50(m,2H),5.90(t,J=54.4Hz,1H),4.94(s,1H),4.86(s,2H),4.63(s,2H),3.54(td,J=14.4,3.6Hz,2H);
MS(ES-API,pos.ion)m/z:304.00[M+H]+。
参照常规的制备方法,本发明还制备得到以下表1中的中间体化合物。
表1
使用相应的物料及条件,参照实施例1的合成方法进行制备,即可得到表2中的目标化合物。
表2
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活性测试
1.试验方法-供试靶标:粘虫
浸叶法:供试靶标为粘虫,将适量玉米叶片在配好的药液中充分浸润后自然阴干,放入垫有滤纸的培养皿中,接粘虫3龄中期幼虫10头/皿,置于24~27℃观察室内培养,72h后调查结果,样品试验浓度200mg/L。
试验结果表明实施例2,实施例3和实施例4对粘虫致死率≥90%。
2.试验方法-供试靶标:桃蚜
喷雾法:选取生长一致的豇豆叶片,用打孔器做成叶碟,每皿两个叶碟,在培养皿里放置湿海绵块,海绵上放叶碟,加水与叶碟齐平,备用。将室内饲养的2-3龄桃蚜接种到准备好的叶碟上,每碟15头以上。采用喷雾塔进行处理,每处理喷药液量为0.5mL。药剂处理后的试材置于观察室,2d后观察结果。以毛笔触动虫体,无反应视为死虫,试验浓度200mg/L。
试验结果表明实施例6,实施例10,实施例11对桃蚜致死率≥80%。
3.试验方法-供试靶标:粉虱
喷雾法:将长势一致的茄子苗放入粉虱饲养笼中,24h后将已产卵的植株转移到无虫笼中正常培养,待若虫长至3龄,采用直径为12mm打孔器进行取样,将所取叶碟置于9cm培养皿中(以琼脂保湿),在体式显微镜下计数若虫数,然后用potter喷雾塔将配制好的药液进行药剂处理,自然阴干后放入人工气候箱中,3天后在体视显微镜下计数若虫死、活虫数,计算死亡率,试验浓度200mg/L。
试验结果表明实施例6,实施例10,实施例11对粉虱致死率≥80%。
以上详细描述了本发明的优选实施方式,但是,本发明并不限于上述实施方式中的具体细节,在本发明的技术构思范围内,可以对本发明的技术方案进行多种简单变型,这些简单变型均属于本发明的保护范围。
Claims (6)
1.一种化合物,其为具有下列之一结构的化合物或其盐:
2.一种组合物,包含权利要求1所述的化合物和农药学上可接受的辅料。
3.权利要求1所述的化合物或权利要求2所述的组合物在防治粘虫中的应用。
4.一种化合物,其为具有下列之一结构的化合物或其盐:
5.一种组合物,包含权利要求4所述的化合物和农药学上可接受的辅料。
6.权利要求4所述的化合物或权利要求5所述的组合物在防治桃蚜和/或粉虱中的应用。
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