CN100354260C - 邻苯二酰胺衍生物、农业或园艺业杀虫剂及其使用方法 - Google Patents
邻苯二酰胺衍生物、农业或园艺业杀虫剂及其使用方法 Download PDFInfo
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- CN100354260C CN100354260C CNB038146509A CN03814650A CN100354260C CN 100354260 C CN100354260 C CN 100354260C CN B038146509 A CNB038146509 A CN B038146509A CN 03814650 A CN03814650 A CN 03814650A CN 100354260 C CN100354260 C CN 100354260C
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- LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
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- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 0.000 description 1
- CHNQZRKUZPNOOH-UHFFFAOYSA-J zinc;manganese(2+);n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[Zn+2].[S-]C(=S)NCCNC([S-])=S.[S-]C(=S)NCCNC([S-])=S CHNQZRKUZPNOOH-UHFFFAOYSA-J 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
-
- 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
- A01N41/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom not containing sulfur-to-oxygen bonds, e.g. polysulfides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/1651—Esters of thiophosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2454—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic
- C07F9/2458—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic of aliphatic amines
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- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (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)
- Plural Heterocyclic Compounds (AREA)
Abstract
通式(I)代表的邻苯二酰胺衍生物:式(I)中R1代表氢、C1-6烷基、被C1-6烷硫基取代的C1-6烷基等;R2和R3可以相同或不同,各自代表氢、C1-6烷基、C1-6卤代烷基等;X可以相同或不同并且各自代表卤素、硝基等;Y可以相同或不同并且各自代表卤素、硝基、C1-6烷基等;m是0—2;n是0—3。含有该邻苯二酰胺衍生物作为活性成分的农业或园艺业杀虫剂具有优异的杀虫作用,即使是当使用少量活性成分时。
Description
技术领域
本发明涉及一种含有邻苯二酰胺衍生物作为活性成分的农业园艺业杀虫剂及其使用方法。
背景技术
与本发明类似的邻苯二酰胺衍生物已知可用作农业园艺业杀虫剂(见例如日本专利申请公开(KOKAI)号11-240857、2001-131141、2001-158764、2001-240580和2001-335563)。然而,通式(I)代表的具有特殊取代基的邻苯二酰胺衍生物尚未被公开或暗示。
在种植业如农业和园艺业中,仍因害虫虫害等造成大量损失。由于如害虫虫害对已有杀虫剂表现抗性的原因,因此需要研制新的农业园艺业杀虫剂。此外,由于农民日渐年长,希望有各种节省劳力的施药方法,并且希望制造出具有适用于上述施药方法的特征的农业园艺业杀虫剂。
发明内容
本发明人为研制出新的农业园艺业杀虫剂进行了深入的研究,结果通过发现通式(I)代表的邻苯二酰胺衍生物是一种文献中描述的新化合物;在比现有文献中描述的那些化合物更低的剂量下显示出优异的杀虫作用;特别是通过土壤处理,显示出提高了从根部的吸收易位作用,并因此具有出色的杀虫作用而完成了本发明。
更确切地说,本发明涉及通式(I)代表的邻苯二酰胺衍生物和含有该化合物作为活性成分的农业园艺业杀虫剂以及其使用方法:
其中R1代表氢;C3-6环烷基;卤代C3-6环烷基;苯基;具有一个或多个取代基的被取代的苯基,所述取代基可以相同或不同,并且选自卤素、C1-6烷基、卤代C1-6烷基、C1-6烷氧基、卤代C1-6烷氧基、C1-6烷硫基、卤代C1-6烷硫基、C1-6烷基亚磺酰基、卤代C1-6烷基亚磺酰基、C1-6烷基磺酰基或卤代C1-6烷基磺酰基;杂环基;具有一个或多个取代基的被取代的杂环基,所述取代基可以相同或不同,并且选自卤素、C1-6烷基、卤代C1-6烷基、C1-6烷氧基、卤代C1-6烷氧基、C1-6烷硫基、卤代C1-6烷硫基、C1-6烷基亚磺酰基、卤代C1-6烷基亚磺酰基、C1-6烷基磺酰基或卤代C1-6烷基磺酰基;或-A-(G)r,其中A代表C1-6亚烷基、C3-6亚烯基或C3-6亚炔基;G可以相同或不同并且各自代表氢;卤素;氰基;硝基;卤代C1-6烷基;C3-6环烷基;卤代C3-6环烷基;相同或不同的二C1-6烷氧基磷酰基;相同或不同的二C1-6烷氧基硫代磷酰基;二苯基膦基;二苯基膦酰基;相同或不同的C1-6二烷基锍;苯基;具有一个或多个取代基的被取代的苯基,所述取代基可以相同或不同,并且选自卤素、C1-6烷基、卤代C1-6烷基、C1-6烷氧基、卤代C1-6烷氧基、C1-6烷硫基、卤代C1-6烷硫基、C1-6烷基亚磺酰基、卤代C1-6烷基亚磺酰基、C1-6烷基磺酰基或卤代C1-6烷基磺酰基;杂环基;具有一个或多个取代基的被取代的杂环基,所述取代基可以相同或不同,并且选自卤素、C1-6烷基、卤代C1-6烷基、C1-6烷氧基、卤代C1-6烷氧基、C1-6烷硫基、卤代C1-6烷硫基、C1-6烷基亚磺酰基、卤代C1-6烷基亚磺酰基、C1-6烷基磺酰基或卤代C1-6烷基磺酰基;-Z-R4,其中Z代表-O-;-N(R5)-(R5代表氢;C1-6烷基羰基;卤代C1-6烷基羰基;C1-6烷氧基羰基;苯基羰基;具有一个或多个取代基的取代的苯基羰基,所述取代基可以相同或不同,并且选自卤素、C1-6烷基、卤代C1-6烷基、C1-6烷氧基、卤代C1-6烷氧基、C1-6烷硫基、卤代C1-6烷硫基、C1-6烷基亚磺酰基、卤代C1-6烷基亚磺酰基、C1-6烷基磺酰基或卤代C1-6烷基磺酰基;C1-6烷基磺酰基;或卤代C1-6烷基磺酰基);R4代表氢;C1-6烷基;卤代C1-6烷基;C3-6烯基;卤代C3-6烯基;C3-6炔基;卤代C3-6炔基;C3-6环烷基;卤代C3-6环烷基;C1-6烷氧基C1-6烷基;C1-6烷硫基C1-6烷基;甲酰基;C1-6烷基羰基;卤代C1-6烷基羰基;C1-6烷氧基羰基;单C1-6烷基氨基羰基;相同或不同的二C1-6烷基氨基羰基;单C1-6烷基氨基硫代羰基;相同或不同的二C1-6烷基氨基硫代羰基;相同或不同的二C1-6烷氧基磷酰基;相同或不同的二C1-6烷氧基硫代磷酰基;苯基;具有一个或多个取代基的取代的苯基,所述取代基可以相同或不同,并且选自卤素、C1-6烷基、卤代C1-6烷基、C1-6烷氧基、卤代C1-6烷氧基、C1-6烷硫基、卤代C1-6烷硫基、C1-6烷基亚磺酰基、卤代C1-6烷基亚磺酰基、C1-6烷基磺酰基或卤代C1-6烷基磺酰基;苯基C1-4烷基;环上具有一个或多个取代基的被取代的苯基C1-4烷基,所述取代基可以相同或不同,并且选自卤素、C1-6烷基、卤代C1-6烷基、C1-6烷氧基、卤代C1-6烷氧基、C1-6烷硫基、卤代C1-6烷硫基、C1-6烷基亚磺酰基、卤代C1-6烷基亚磺酰基、C1-6烷基磺酰基或卤代C1-6烷基磺酰基;杂环基;或具有一个或多个取代基的取代的杂环基,所述取代基可以相同或不同,并且选自卤素、C1-6烷基、卤代C1-6烷基、C1-6烷氧基、卤代C1-6烷氧基、C1-6烷硫基、卤代C1-6烷硫基、C1-6烷基亚磺酰基、卤代C1-6烷基亚磺酰基、C1-6烷基磺酰基或卤代C1-6烷基磺酰基;或-W-R6,其中W代表-S-、-SO-、-SO2-、-C(=O)-、-C(=S)-或-C(=NOR7)-(R7代表氢;C1-6烷基;卤代C1-6烷基;C3-6烯基;卤代C3-6烯基;C3-6炔基;C3-6环烷基;苯基C1-4烷基;或在环上具有一个或多个取代基的被取代的苯基C1-4烷基,所述取代基可以相同或不同,并且选自卤素、C1-6烷基、卤代C1-6烷基、C1-6烷氧基、卤代C1-6烷氧基、C1-6烷硫基、卤代C1-6烷硫基、C1-6烷基亚磺酰基、卤代C1-6烷基亚磺酰基、C1-6烷基磺酰基或卤代C1-6烷基磺酰基);R6代表氢;C1-6烷基;卤代C1-6烷基;C3-6烯基;卤代C3-6烯基;C3-6炔基;卤代C3-6炔基;C3-6环烷基;卤代C3-6环烷基;C1-6烷氧基C1-6烷基;C1-6烷硫基C1-6烷基;C1-6烷氧基;卤代C1-6烷氧基;C1-6烷硫基;卤代C1-6烷硫基;氨基;单C1-6烷基氨基;相同或不同的二C1-6烷基氨基;C1-6烷氧基C1-6烷基氨基;C1-6烷硫基C1-6烷基氨基;苯基;具有一个或多个取代基的取代苯基,所述取代基可以相同或不同,并且选自卤素、C1-6烷基、卤代C1-6烷基、C1-6烷氧基、卤代C1-6烷氧基、C1-6烷硫基、卤代C1-6烷硫基、C1-6烷基亚磺酰基、卤代C1-6烷基亚磺酰基、C1-6烷基磺酰基或卤代C1-6烷基磺酰基;苯基C1-4烷基;环上具有一个或多个取代基的被取代的苯基C1-4烷基,所述取代基可以相同或不同,并且选自卤素、C1-6烷基、卤代C1-6烷基、C1-6烷氧基、卤代C1-6烷氧基、C1-6烷硫基、卤代C1-6烷硫基、C1-6烷基亚磺酰基、卤代C1-6烷基亚磺酰基、C1-6烷基磺酰基或卤代C1-6烷基磺酰基;苯基氨基;环上具有一个或多个取代基的被取代的苯基氨基,所述取代基可以相同或不同,并且选自卤素、C1-6烷基、卤代C1-6烷基、C1-6烷氧基、卤代C1-6烷氧基、C1-6烷硫基、卤代C1-6烷硫基、C1-6烷基亚磺酰基、卤代C1-6烷基亚磺酰基、C1-6烷基磺酰基或卤代C1-6烷基磺酰基;苯基C1-4烷基氨基;环上具有一个或多个取代基的被取代的苯基C1-4烷基氨基,所述取代基可以相同或不同,并且选自卤素、C1-6烷基、卤代C1-6烷基、C1-6烷氧基、卤代C1-6烷氧基、C1-6烷硫基、卤代C1-6烷硫基、C1-6烷基亚磺酰基、卤代C1-6烷基亚磺酰基、C1-6烷基磺酰基或卤代C1-6烷基磺酰基;杂环基;具有一个或多个取代基的被取代的杂环基,所述取代基可以相同或不同,并且选自卤素、C1-6烷基、卤代C1-6烷基、C1-6烷氧基、卤代C1-6烷氧基、C1-6烷硫基、卤代C1-6烷硫基、C1-6烷基亚磺酰基、卤代C1-6烷基亚磺酰基、C1-6烷基磺酰基或卤代C1-6烷基磺酰基;杂环基氨基;或环上具有一个或多个取代基的被取代的杂环氨基,所述取代基可以相同或不同,并且选自卤素、C1-6烷基、卤代C1-6烷基、C1-6烷氧基、卤代C1-6烷氧基、C1-6烷硫基、卤代C1-6烷硫基、C1-6烷基亚磺酰基、卤代C1-6烷基亚磺酰基、C1-6烷基磺酰基或卤代C1-6烷基磺酰基;r代表1-3的整数;R4或R6与A一起可形成四元至八元环,该环可被一个或两个相同或不同的氧、硫或氮间断;
R2和R3可以相同或不同,并且各自代表氢、C1-6烷基、卤代C1-6烷基、C3-6烯基、卤代C3-6烯基、C3-6炔基、卤代C3-6炔基、C3-6环烷基、卤代C3-6环烷基、C1-6烷氧基C1-6烷基、C1-6烷硫基C1-6烷基、甲酰基、C1-6烷基羰基、卤代C1-6烷基羰基、C1-6烷氧基羰基、单C1-6烷基氨基羰基、或相同或不同的二C1-6烷基氨基羰基;和R2与A、R1、G、R4或R6一起可形成四元至八元环,该环可被一个或两个相同或不同的氧、硫或氮间断;
X可以相同或不同,并且各自代表卤素,硝基,氨基,单C1-6烷基氨基,相同或不同的二C1-6烷基氨基,C1-6烷基羰基氨基,卤代C1-6烷基羰基氨基,C1-6烷基磺酰基氨基,卤代C1-6烷基磺酰基氨基,氰基,C1-6烷基,卤代C1-6烷基,C2-6烯基,卤代C2-6烯基,C2-6炔基,卤代C2-6炔基,C1-6烷氧基,卤代C1-6烷氧基,C1-6烷基羰氧基,卤代C1-6烷基羰氧基,C1-6烷基磺酰氧基,卤代C1-6烷基磺酰氧基,C1-6烷硫基,卤代C1-6烷硫基,C1-6烷基亚磺酰基,卤代C1-6烷基亚磺酰基,C1-6烷基磺酰基或卤代C1-6烷基磺酰基;和芳环上彼此相邻的两个X可一起形成稠合环,该稠合环可有一个或多个取代基,所述取代基可以相同或不同,并且选自卤素、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、C1-6烷硫基、卤代C1-6烷硫基、C1-6烷基亚磺酰基、卤代C1-6烷基亚磺酰基、C1-6烷基磺酰基或卤代C1-6烷基磺酰基;
m代表0-2的整数;
Y可以相同或不同,并且各自代表卤素;硝基;氰基;C1-6烷基;卤代C1-6烷基;环C3-6烷基;C1-6烷氧基;卤代C1-6烷氧基;单C1-6烷基氨基,相同或不同的二C1-6烷基氨基,C1-6烷硫基;卤代C1-6烷硫基;C1-6烷基亚磺酰基;卤代C1-6烷基亚磺酰基;C1-6烷基磺酰基;卤代C1-6烷基磺酰基;苯基;具有一个或多个取代基的被取代的苯基,所述取代基可以相同或不同,并且选自卤素、C1-6烷基、卤代C1-6烷基、C1-6烷氧基、卤代C1-6烷氧基、C1-6烷硫基、卤代C1-6烷硫基、C1-6烷基亚磺酰基、卤代C1-6烷基亚磺酰基、C1-6烷基磺酰基或卤代C1-6烷基磺酰基;苯基C1-4烷基;环上有一个或多个取代基的被取代的苯基C1-4烷基,所述取代基可以相同或不同,并且选自卤素、C1-6烷基、卤代C1-6烷基、C1-6烷氧基、卤代C1-6烷氧基、C1-6烷硫基、卤代C1-6烷硫基、C1-6烷基亚磺酰基、卤代C1-6烷基亚磺酰基、C1-6烷基磺酰基或卤代C1-6烷基磺酰基;苯氧基;有一个或多个取代基的被取代的苯氧基,所述取代基可以相同或不同,并且选自卤素、C1-6烷基、卤代C1-6烷基、C1-6烷氧基、卤代C1-6烷氧基、C1-6烷硫基、卤代C1-6烷硫基、C1-6烷基亚磺酰基、卤代C1-6烷基亚磺酰基、C1-6烷基磺酰基或卤代C1-6烷基磺酰基;苯硫基;有一个或多个取代基的被取代的苯硫基,所述取代基可以相同或不同,并且选自卤素、C1-6烷基、卤代C1-6烷基、C1-6烷氧基、卤代C1-6烷氧基、C1-6烷硫基、卤代C1-6烷硫基、C1-6烷基亚磺酰基、卤代C1-6烷基亚磺酰基、C1-6烷基磺酰基或卤代C1-6烷基磺酰基;杂环基;或具有一个或多个取代基的被取代的杂环基,所述取代基可以相同或不同,并且选自卤素、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、C1-6烷硫基、卤代C1-6烷硫基、C1-6烷基亚磺酰基、卤代C1-6烷基亚磺酰基、C1-6烷基磺酰基或卤代C1-6烷基磺酰基;芳环上彼此相邻的两个Y可一起形成稠合环,该稠合环可有一个或多个取代基,所述取代基可以相同或不同,并且选自卤素、C1-6烷基、卤代C1-6烷基、C1-6烷氧基、卤代C1-6烷氧基、C1-6烷硫基、卤代C1-6烷硫基、C1-6烷基亚磺酰基、卤代C1-6烷基亚磺酰基、C1-6烷基磺酰基或卤代C1-6烷基磺酰基;和Y与R3一起可形成五元至七元环,该环可被一个或两个相同或不同的氧、硫或氮间断;
n代表0-3的整数。
本发明的化合物在小剂量下显示出优异的杀虫效果,特别是通过土壤处理,显示出从根部的吸收易位作用提高。
本发明的最佳实施方式
在本发明通式(I)的邻苯二酰胺衍生物的定义中,“卤素”指氯、溴、碘或氟;“C1-6烷基”指有1-6个碳原子的直链或支链烷基如甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正戊基、新戊基和正己基;“卤代C1-6烷基”指被相同或不同的一个或多个卤素取代的具有1-6个碳原子的直链或支链烷基,可以提及例如三氟甲基、二氟甲基、全氟乙基、全氟异丙基、氯甲基、溴甲基、1-溴乙基和2,3-二溴丙基;“C1-8亚烷基”指具有1-8个碳原子的直链或支链亚烷基如亚甲基、亚乙基、亚丙基、三亚甲基、二甲基亚甲基、四亚甲基、亚异丁基、二甲基亚乙基和八亚甲基;“C3-6亚烯基”或“C3-6亚炔基”也指具有3-6个碳原子的直链或支链亚烯基或亚炔基;“C3-6环烷基”指具有3-6个碳原子的脂环族烷基如环丙基、环丁基、环戊基和环己基。
“杂环基”指有一个或多个杂原子的五元或六元杂环基,杂原子选自氧、硫或氮,实例包括吡啶基、吡啶N-氧化物、嘧啶基、呋喃基、四氢呋喃基、噻吩基、四氢噻吩基、四氢吡喃基、四氢噻喃基、唑基、异唑基、二唑基、噻唑基、异噻唑基、噻二唑基、咪唑基、三唑基和吡唑基;“稠环”的实例包括萘、四氢萘、茚、二氢化茚、喹啉、喹唑啉、吲哚、二氢吲哚、苯并二氢吡喃、异色满(isochromane)、苯并二烷、苯并间二氧杂环戊烯、苯并呋喃、二氢苯并呋喃、苯并噻吩,二氢苯并噻吩、苯并唑、苯并噻唑、苯并咪唑和吲唑。
本发明通式(I)代表的邻苯二酰胺衍生物有时含有一个或多个不对称碳原子或结构中的不对称中心,并且有时还具有两个或多个光学异构体和非对映体。本发明旨在包括所有各个异构体和含任意比例的上述异构体的混合物。而且,本发明通式(I)代表的邻苯二酰胺衍生物有时含有得自碳-碳双键或碳-氮双键的两种几何异构体。本发明还旨在包括所有这些各个几何异构体以及含任意比例的上述异构体的混合物。
在本发明通式(I)代表的邻苯二酰胺衍生物中,优选化合物的实例可包括其中R1代表C1-6烷基、C1-6烷硫基C1-6烷基、C1-6烷基亚磺酰基C1-6烷基或C1-6烷基磺酰基C1-6烷基;R2和R3代表氢;X代表卤素;m代表1;Y代表卤素或C1-6烷基;n代表0-2的整数的邻苯二酰胺衍生物。
本发明通式(I)代表的邻苯二酰胺衍生物可通过例如下文所示方案由通式(II)代表的苯胺衍生物制备,通式(II)化合物可通过在UK专利2276379、WO94/21606等种公开的方案制备,还可通过在日本专利公开号11-240857和2001-131141种公开的方案制备。
方案
其中各R1、R2、R3、X、Y、m和n具有如上所述相同的含义;“halo”代表卤素。
本发明通式(I-1)代表的邻苯二酰胺衍生物可通过通式(II)代表的苯胺衍生物与通式(III-1)代表的邻苯异二甲酰亚胺(phthalisoimide)衍生物在有或无酸或碱的条件下在惰性溶剂中反应制备,所述式(III-1)化合物可通过日本专利公开号11-240857和2001-131141等中公开的方案制备。
通式(I-2)代表的邻苯二酰胺衍生物的制备可通过由通式(II)代表的苯胺衍生物按照日本专利公开号11-240857和2001-131141等中公开的方案制造通式(III-2)代表的邻苯异酰亚胺衍生物,然后将该邻苯异酰亚胺衍生物与通式(IV)代表的胺在有或无酸或碱的存在下在惰性溶剂中反应。
通式(I)代表的邻苯二酰胺衍生物可通过通式(I-1)或(I-2)代表的邻苯二酰胺衍生物与通式(V-1)或(V-2)代表的卤化物在脱卤化氢(non-hydrogen halide)试剂的存在下在惰性溶剂中反应制备。
在通式(I)的R1定义中,当R1代表-A-(G)r并且G代表-W-R6时,W代表-SO-或-SO2-的化合物可通过以常规方式例如使用氧化剂如间-氯过苯甲酸和过氧化氢对W代表-S-的化合物进行氧化反应制备。
1-1.通式(II)→通式(I-1)或通式(III-2)→通式(I-2)
依照J.Med.Chem.,10,982(1967)所述方法,此反应可制备所需产物。必要时,此反应可在催化量至过量的酸或碱的存在下进行。
可用于此反应的酸的实例包括有机酸如乙酸和三氟乙酸,和无机酸如盐酸和硫酸。其用量可在催化量至相对于通式(III-1)或(III-2)的邻苯异酰亚胺衍生物过量摩尔的范围内适当地选择。碱的实例包括有机碱例如三乙基胺和吡啶;和无机碱如碳酸钾、碳酸氢钠、碳酸钠和氢氧化钠。其用量可在催化量至相对于通式(III-1)或(III-2)邻苯异酰亚胺衍生物过量摩尔的范围内适当地选择。
反应温度可以是从0℃至所用惰性溶剂的沸点。反应时间不是恒定的,这取决于反应规模、反应温度等,但是在几分钟至48小时范围内。反应完成后,以常规方式将所需产物从含有所需产物的反应系统中分离,必要时通过重结晶、柱色谱等进行纯化以制备出需要产物。
1-2.通式(I-1)→通式(I)或(I-2)→通式(I)
任何惰性溶剂均可用于此反应,只要其不显著抑制此反应进程。其实例包括芳族烃如苯、甲苯和二甲苯;卤代芳族烃如氟苯、氯苯和二氯苯;卤代烃如二氯甲烷、氯仿和四氯化碳;链型或环状醚如二乙醚、二烷和四氢呋喃;酯类如乙酸乙酯;酰胺类如二甲基甲酰胺和二甲基乙酰胺;酸如乙酸;和惰性溶剂如二甲基亚砜和1,3-二甲基-2-咪唑烷酮。这些惰性溶剂可单独或作为其混合物使用。
脱卤化氢试剂的实例包括有机碱如三乙基胺和吡啶;和无机碱如碳酸钾、碳酸氢钠、碳酸钠和氢氧化钠。此反应是等摩尔反应,因此可使用等摩尔量的各反应试剂,但任何反应试剂均可过量使用。
反应温度可以是从室温至所用惰性溶剂的回流温度。反应时间不恒定,这取决于反应规模、反应温度等,但可在几分钟至48小时范围内适当地选择。
反应完成后,以常规方式将所需产物从含有所需产物的反应系统中分离,必要时通过重结晶、柱色谱等进行纯化以制备出需要产物。
通式(I)代表的邻苯二酰胺的典型化合物示于下表1至3中,但本发明并不限于此。
在表中,“n-”指正的,“s-”指仲,“t”指叔,“c-”指环,“ph”指苯基,“pyr”指吡啶基,“C(*)”指不对称碳原子。
通式(I-3)
表1(R2=R3=H)
编号 | R1 | Xm | Yn | 熔点(℃) |
1-11-21-31-41-51-61-71-81-91-101-111-121-131-141-151-161-171-181-191-201-211-221-231-241-251-261-271-281-291-301-31 | CH3C2H5n-C3H7i-C3H7c-C3H5n-C4H9s-C4H9t-C4H9i-C4H9n-C5H11s-C5H11t-C5H11c-C5H9CH2CH=CH2CH2C≡CHCH(CH3)CH=CH2C(CH3)2CH=CH2CH(CH3)CH=CH-PhC(CH3)2CH=CH-2-PyrCH(CH3)C≡CHC(CH3)2C≡CHC(CH3)2C≡C-PhC(CH3)2C≡C-2-PyrC(CH3)2C≡CHCH(CH3)CF3CH(CH3)CH2CF3CH(CH3)CH2CH2FCH(CH3)CH2CH2ClC(CH3)2CH2CH2FC(CH3)2CH2CH2ClCH2Ph | 3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I | 2-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH3 |
表1(续)
编号 | R1 | Xm | Yn | 熔点(℃) |
1-321-331-341-351-361-371-381-391-401-411-421-431-441-451-461-471-481-491-501-511-521-531-541-551-561-571-581-591-601-611-621-631-641-651-661-671-681-691-701-71 | CH(CH3)PhC(CH3)2PhCH(CH3)CH2PhC(CH3)2CH2PhCH(CH3)-2-PyrCH(CH3)-3-PyrC(CH3)2-2-PyrC(CH3)3-3-PyrPh(3-SCH3)Ph(4-SCH3)Ph(3-CH2SCH3)Ph(4-CH2SCH3)Ph(3-SO2NH2)Ph(4-SO2NH2)Ph(3-CONH2)Ph(4-CONH2)Ph3-Pyr3-(4-SCH3)Pyr3-(2-CH3-4-SCH3)Pyri-C3H7s-C4H9t-C4H9s-C5H11t-C5H11CH2CO2CH3CH(CH3)CO2CH3CH(CH3)CO2C2H5C(CH3)2CO2CH3C(CH3)2CO2C2H5CH(CH3)CH2CO2CH3CH(CH3)CH2CO2C2H5C(CH3)2CH2CO2CH3C(CH3)2CH2CO2C2H5CH(CH3)(CH2)2CO2CH3CH(CH3)(CH2)2CO2C2H5C(CH3)2(CH2)2CO2CH3C(CH3)2(CH2)2CO2C2H5CH(CH3)CH=CHCO2CH3CH(CH3)CH=CHCO2C2H5 | 3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I | 2-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-Cl2-Cl2-Cl2-Cl2-Cl2-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH3 |
表1(续)
编号 | R1 | Xm | Yn | 熔点(℃) |
1-721-731-741-751-761-771-781-791-801-811-821-831-841-851-861-871-881-891-901-911-921-931-941-951-961-971-981-991-1001-1011-1021-1031-1041-1051-1061-1071-1081-1091-1101-111 | C(CH3)2CH=CHCO2CH3C(CH3)2CH=CHCO2C2H5CH(CH3)C≡CCO2CH3CH(CH3)C≡CCO2C2H5C(CH3)2C≡CCO2CH3C(CH3)2C≡CCO2C2H5CH2CNCH(CH3)CNC(CH3)2CNCH(CH3)CH2CNC(CH3)2CH2CNCH(CH3)CONH2C(CH3)2CONH2CH(CH3)CONHC2H5C(CH3)2CONHC2H5CH(CH3)CON(C2H5)2C(CH3)2CON(C2H5)2CH(CH3)CH2CONHC2H5C(CH3)2CH2CONHC2H5CH(CH3)CH2CON(C2H5)2C(CH3)2CH2CON(C2H5)2C(CH3)2(CH2)2CONHC2H5C(CH3)2(CH2)2CON(C2H5)2CH(CH3)CH=CHCONHC2H5CH(CH3)CH=CHCON(C2H5)2C(CH3)2CH=CHCONHC2H5C(CH3)2CH=CHCON(C2H5)2CH(CH3)C≡CCONHC2H5CH(CH3)C≡CCON(C2H5)2C(CH3)2C≡CCONHC2H5C(CH3)2C≡CCON(C2H5)2CH(CH3)CH=OC(CH3)2CH=OCH(CH3)C(=O)CH3C(CH3)2C(=O)CH3CH(CH3)CH=NOHC(CH3)2CH=NOHCH(CH3)C(=O)CH3C(CH3)2C(=O)CH3CH(CH3)CH=NOCH3 | 3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I | 2-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH3 |
表1(续)
编号 | R1 | Xm | Yn | 熔点(℃) |
1-1121-1131-1141-1151-1161-1171-1181-1191-1201-1211-1221-1231-1241-1251-1261-1271-1281-1291-1301-1311-1321-1331-1341-1351-1361-1371-1381-1391-1401-1411-1421-1431-1441-1451-1461-1471-1481-1491-1501-151 | C(CH3)2CH=NOCH3CH(CH3)CH=NOC2H5C(CH3)2CH=NOC2H5CH(CH3)CH2CH=NOCH3C(CH3)2CH2CH=NOCH3CH(CH3)CH2CH=NOC2H5C(CH3)2CH2CH=NOC2H5CH(CH3)CH2CH=NOCH2PhC(CH3)2CH2CH=NOCH2PhCH(CH3)CH=NOCH2CH=CH2C(CH3)2CH=NOCH2CH=CH2CH(CH3)CH=NOCH2C≡CHC(CH3)2CH=NOCH2C≡CHCH(CH3)CH=NO(CH2)2OCH3C(CH3)2CH=NO(CH2)2OCH3CH(CH3)2CH=NO(CH2)2OC2H5C(CH3)2CH=NO(CH2)2OC2H5CH(CH3)CH=NO(CH2)2SCH3C(CH3)2CH=NO(CH2)2SCH3CH(CH3)CH=NOCH2CO2C2H5C(CH3)2CH=NOCH2CO2C2H5CH(CH3)C(CH3)=NOCH3C(CH3)2C(CH3)=NOCH3CH(CH3)C(CH3)=NOC2H5C(CH3)2C(CH3)=NOC2H5C(CH3)2CH2CO2C2H5C(CH3)2(CH2)2CO2C2H5CH(CH3)CH=CHCO2C2H5C(CH3)2CH=CHCO2C2H5C(CH3)2C≡CCO2C2H5C(CH3)2CH2CNC(CH3)2CONHC2H5C(CH3)2CON(C2H5)2C(CH3)2CH2CONHC2H5C(CH3)2CH2CON(C2H5)2C(CH3)2(CH2)2CONHC2H5C(CH3)2(CH2)2CON(C2H5)2C(CH3)2CH=CHCONHC2H5C(CH3)2CH=CHCON(C2H5)2C(CH3)2CH=NOH | 3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I | 2-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-Cl2-Cl2-Cl2-Cl2-Cl2-Cl2-Cl2-Cl2-Cl2-Cl2-Cl2-Cl2-Cl2-Cl2-Cl |
表1(续)
编号 | R1 | Xm | Yn | 熔点(℃) |
1-1521-1531-1541-1551-1561-1571-1581-1591-1601-1611-1621-1631-1641-1651-1661-1671-1681-1691-1701-1711-1721-1731-1741-1751-1761-1771-1781-1791-1801-1811-1821-1831-1841-1851-1861-1871-1881-1891-1901-191 | C(CH3)2CH=NOCH3C(CH3)2CH=NOCH2CH=CH2C(CH3)2CH=NOCH2C≡CHC(CH3)2CH2CH=NOHC(CH3)2CH2CH=NOCH3(CH2)2OCH3(CH2)3OCH3(CH2)2OC2H5CH(CH3)CH2OHC(CH3)2CH2OHCH(CH3)CH2OCH3C(CH3)2CH2OCH3CH(CH3)CH2OC2H5C(CH3)2CH2OC2H5CH(CH3)CH2OCH2CH=CH2C(CH3)2CH2OCH2CH=CH2CH(CH3)CH2OCH2C≡CHC(CH3)2CH2OCH2C≡CHCH(CH3)(CH2)2OCH3C(CH3)2(CH2)2OCH3CH(CH3)(CH2)3OCH3C(CH3)2(CH2)3OCH3CH(CH3)(CH2)4OCH3C(CH3)2(CH2)4OCH3CH(CH3)CH2OCH2CF3C(CH3)2CH2OCH2CF3CH(CH3)CH2OCH2CNC(CH3)2CH2OCH2CNCH(CH3)CH2OCH2CO2N(CH3)2C(CH3)2CH2OCH2CO2N(CH3)2CH(CH3)CH2O(CH2)2OCH3C(CH3)2CH2O(CH2)2OCH3CH(CH3)CH2OCH2PhC(CH3)2CH2OCH2PhCH(CH3)CH2O-PhC(CH3)2CH2O-PhCH(CH3)CH2O-2-PyrC(CH3)2CH2O-2-PyrCH(CH3)CH2O-3-PyrC(CH3)2CH2O-3-Pyr | 3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I | 2-Cl2-Cl2-Cl2-Cl2-Cl2-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-Cl2-Cl2-Cl2-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH3 |
表1(续)
编号 | R1 | Xm | Yn | 熔点(℃) |
1-1921-1931-1941-1951-1961-1971-1981-1991-2001-2011-2021-2031-2041-2051-2061-2071-2081-2091-2101-2111-2121-2131-2141-2151-2161-2171-2181-2191-2201-2211-2221-2231-2241-2251-2261-2271-2281-2291-2301-231 | CH(CH3)CH2OC(=O)CH3C(CH3)2CH2OC(=O)CH3CH(CH3)CH2OC(=O)CF3C(CH3)2CH2OC(=O)CF3CH(CH3)CH2OCO2CH3C(CH3)2CH2OCO2CH3CH(CH3)CH2OC(=O)NHCH3C(CH3)2CH2OC(=O)NHCH3CH(CH3)CH2OC(=O)NH(C2H5)C(CH3)2CH2OC(=O)NH(C2H5)CH(CH3)CH2OC(=O)N(CH3)2C(CH3)2CH2OC(=O)N(CH3)2CH(CH3)CH2OC(=O)N(C2H5)2C(CH3)2CH2OC(=O)N(C2H5)2CH(CH3)CH2OC(=O)NHCH2PhC(CH3)2CH2OC(=O)NHCH2PhC(CH3)2CH2OCONH(CH2)3SCH3C(CH3)2CH2OCONH(CH2)2OCH3CH(CH3)CH2OC(=S)NHCH3C(CH3)CH2OC(=S)NHCH3CH(CH3)CH2OC(=S)N(C2H5)2C(CH3)CH2OC(=S)N(C2H5)2CH(CH3)CH2OCONH(C2H5)CH(CH3)CH2OCON(CH3)2CH(CH3)CH2OCON(C2H5)2CH(CH3)CH2OP(=O)(OCH3)2C(CH3)2CH2OP(=O)(OCH3)2CH(CH3)CH2OP(=O)(OC2H5)2C(CH3)2CH2OP(=O)(OC2H5)2CH(CH3)CH2OP(=S)(OCH3)2C(CH3)2CH2OP(=S)(OCH3)2CH(CH3)CH2OP(=S)(OC2H5)2C(CH3)2CH2OP(=S)(OC2H5)2CH(CH3)CH2OCH3C(CH3)2CH2OCH3CH(CH3)CH2OC2H5C(CH3)2CH2OC2H5CH(CH3)(CH2)2OCH3C(CH3)2(CH2)2OCH3C(CH3)2(CH2)3OCH3 | 3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I | 2-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-Cl2-Cl2-Cl2-Cl2-Cl2-Cl2-Cl |
表1(续)
编号 | R1 | Xm | Yn | 熔点(℃) |
1-2321-2331-2341-2351-2361-2371-2381-2391-2401-2411-2421-2431-2441-2451-2461-2471-2481-2491-2501-2511-2521-2531-2541-2551-2561-2571-2581-2591-2601-2611-2621-2631-2641-2651-2661-2671-2681-2691-2701-271 | C(CH3)2(CH2)4OCH3C(CH3)2CH2OP(=S)(OCH3)2CH(CH3)CH2OP(=S)(OC2H5)2C(CH3)2CH2OP(=S)(OC2H5)2CH(CH3)CH2NHCOCH3C(CH3)2CH2NHCOCH3CH(CH3)CH2N(CH3)COCH3C(CH3)2CH2N(CH3)COCH3CH(CH3)CH2NHCOC2H5C(CH3)2CH2NHCOC2H5CH(CH3)CH2NHCO2CH3C(CH3)2CH2NHCO2CH3CH(CH3)CH2NHCO2C2H5C(CH3)2CH2NHCO2C2H5CH(CH3)CH2NHSO2CH3C(CH3)2CH2NHSO2CH3CH(CH3)CH2NHSO2C2H5C(CH3)2CH2NHSO2C2H5CH(CH3)CH2N(CH3)SO2CH3C(CH3)2CH2N(CH3)SO2CH3CH(CH3)CH2NHCONHCH3C(CH3)2CH2NHCONHCH3CH(CH3)CH2NHCON(CH3)2C(CH3)2CH2NHCON(CH3)2CH(CH3)CH2N(CH3)CON(CH3)2C(CH3)2CH2N(CH3)CON(CH3)2CH(CH3)CH2NHCON(C2H5)2C(CH3)2CH2NHCON(C2H5)2CH(CH3)CH2NHSO2NHCH3C(CH3)2CH2NHSO2NHCH3CH(CH3)CH2NHSO2N(CH3)2C(CH3)2CH2NHSO2N(CH3)2CH(CH3)CH2NHSO2N(C2H5)2C(CH3)2CH2NHSO2N(C2H5)2CH(CH3)CH2NHP(=O)(OCH3)2C(CH3)2CH2NHP(=O)(OCH3)2CH(CH3)CH2N(CH3)P(=O)(OCH3)2C(CH3)2CH2N(CH3)P(=O)(OCH3)2CH(CH3)CH2NHP(=S)(OCH3)2C(CH3)2CH2NHP(=S)(OCH3)2 | 3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I | 2-Cl2-Cl2-Cl2-Cl2-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH3 |
表1(续)
编号 | R1 | Xm | Yn | 熔点(℃) |
1-2721-2731-2741-2751-2761-2771-2781-2791-2801-2811-2821-2831-2841-2851-2861-2871-2881-2891-2901-2911-2921-2931-2941-2951-2961-2971-2981-2991-3001-3011-3021-303 | CH(CH3)CH2NHP(=S)(OC2H5)2C(CH3)2CH2NHP(=S)(OC2H5)2CH(CH3)CH2NHCOCH3C(CH3)2CH2NHCOCH3CH(CH3)CH2NHCO2C2H5C(CH3)2CH2NHCO2C2H5CH(CH3)CH2NHSO2CH3C(CH3)2CH2NHSO2CH3CH(CH3)CH2NHSO2N(CH3)2C(CH3)2CH2NHSO2N(CH3)2(CH2)2SCH3(CH2)3SCH3(CH2)2SC2H5(CH2)2SC3H7-iCH(CH3)CH2SHCH(CH3)CH2SCH3CH(CH3)CH2SOCH3CH(CH3)CH2SO2CH3C(*)H(CH3)CH2SCH3(S)-异构体C(*)H(CH3)CH2SOCH3(S)-异构体C(*)H(CH3)CH2SO2CH3(S)-异构体C(*)H(CH3)CH2SCH3(R)-异构体C(*)H(CH3)CH2SOCH3(R)-异构体C(*)H(CH3)CH2SO2CH3(R)-异构体C(CH3)2CH2SCH3C(CH3)2CH2SOCH3C(CH3)2CH2SO2CH3CH(CH3)CH2SC2H5CH(CH3)CH2SOC2H5CH(CH3)CH2SO2C2H5C(*)H(CH3)CH2SC2H5(S)-异构体C(*)H(CH3)CH2SOC2H5(S)-异构体 | 3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I | 2-CH32-CH32-Cl2-Cl2-Cl2-Cl2-Cl2-Cl2-Cl2-Cl2-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH3 | 180-18387-90216-21785-89115-118 |
表1(续)
编号 | R1 | Xm | Yn | 熔点(℃) |
1-3041-3051-3061-3071-3081-3091-3101-3111-3121-3131-3141-3151-3161-3171-3181-3191-3201-3211-3221-3231-3241-3251-3261-3271-3281-3291-3301-3311-3321-3331-3341-3351-3361-3371-3381-339 | C(*)H(CH3)CH2SO2C2H5(S)-异构体C(*)H(CH3)CH2SC2H5(R)-异构体C(*)H(CH3)CH2SOC2H5(R)-异构体C(*)H(CH3)CH2SO2C2H5(R)-异构体C(CH3)2CH2SC2H5C(CH3)2CH2SOC2H5C(CH3)2CH2SO2C2H5CH(CH3)CH2SC3H7-nCH(CH3)CH2SC3H7-iCH(CH3)CH2SCH2CH=CH2CH(CH3)CH2SCH2C≡CHCH(CH3)(CH2)2SCH3C(CH3)2(CH2)2SCH3CH(CH3)(CH2)3SCH3C(CH3)2(CH2)3SCH3CH(CH3)(CH2)4SCH3C(CH3)2(CH2)4SCH3CH(C2H5)(CH2)2SCH3CH(CH3)CH2SCH2CF3CH(CH3)CH2SCH2CNCH(CH3)CH2S(CH2)2OCH3CH(CH3)CH2S(CH2)2SCH3CH(CH3)CH2SCH2CO2N(CH3)2CH(CH3)CH2SCH2CO2N(C2H5)2CH(CH3)CH2SCH2PhCH(CH3)CH2S-PhC(CH3)2CH2S-PhCH(CH3)CH2S-2-PyrC(CH3)2CH2S-2-PyrCH(CH3)CH2S-3-PyrC(CH3)2CH2S-3-PyrCH(CH3)CH2S-4-PyrC(CH3)2CH2S-4-PyrCH(Ph)CH2SCH3CH(CH3)CH2SCOCH3CH(CH3)CH2SCONHCH3 | 3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I | 2-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH3 |
表1(续)
编号 | R1 | Xm | Yn | 熔点(℃) |
1-3401-3411-3421-3431-3441-3451-3461-3471-3481-3491-3501-3511-3521-3531-3541-3551-3561-3571-3581-3591-3601-3611-3621-3631-3641-3651-3661-3671-3681-3691-3701-3711-3721-3731-3741-3751-3761-3771-3781-379 | C(CH3)2CH2SCONHCH3CH(CH3)CH2SCON(C2H5)2C(CH3)2CH2SCON(C2H5)2CH(CH3)CH2SC(=S)NHCH3C(CH3)2CH2SC(=S)NHCH3CH(CH3)CH2SC(=S)N(C2H5)2C(CH3)2CH2SC(=S)N(C2H5)2CH(CH3)CH2S-SCH3C(CH3)2CH2S-SCH3CH(CH3)CH2SO2NH2C(CH3)2CH2SO2NH2CH(CH3)CH2SO2NHCH3C(CH3)2CH2SO2NHCH3CH(CH3)CH2SO2NHC2H5C(CH3)2CH2SO2NHC2H5CH(CH3)CH2SO2N(CH3)2C(CH3)2CH2SO2N(CH3)2CH(CH3)CH2SO2N(C2H5)2C(CH3)2CH2SO2N(C2H5)2CH(CH3)CH2S(=O)OCH3C(CH3)2CH2S(=O)OCH3CH(CH3)CH2S(=O)OC2H5C(CH3)2CH2S(=O)OC2H5CH(CH3)CH2S(CH3)=N-SO2CH3C(CH3)2CH2S(CH3)=N-SO2CH3CH(CH3)CH2S(CH3)=N-SO2PhC(CH3)2CH2S(CH3)=N-SO2PhCH(CH3)CH2S+(CH3)2 I-C(CH3)2CH2S+(CH3)2 I-CH(CH3)CH2SCH3CH(CH3)CH2SOCH3CH(CH3)CH2SO2CH3C(CH3)2CH2SCH3C(CH3)2CH2SOCH3C(CH3)2CH2SO2CH3CH(CH3)CH2SC2H5CH(CH3)CH2SOC2H5CH(CH3)CH2SO2C2H5C(CH3)2CH2SC2H5C(CH3)2CH2SOC2H5 | 3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I | 2-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-Cl2-Cl2-Cl2-Cl2-Cl2-Cl2-Cl2-Cl2-Cl2-Cl2-Cl | 170-17383-87196-198 |
表1(续)
编号 | R1 | Xm | Yn | 熔点(℃) |
1-3801-3811-3821-3831-3841-3851-3861-3871-3881-3891-3901-3911-3921-3931-3941-3951-3961-3971-3981-3991-4001-4011-4021-4031-4041-4051-4061-4071-4081-4091-4101-4111-4121-4131-4141-4151-4161-4171-4181-419 | C(CH3)2CH2SO2C2H5CH(CH3)(CH2)2SCH3C(CH3)2(CH2)2SCH3CH(CH3)(CH2)3SCH3C(CH3)2(CH2)3SCH3CH(CH3)(CH2)4SCH3C(CH3)2(CH2)4SCH3CH(CH3)CH2SO2NH2CH(CH3)CH2SO2NHCH3CH(CH3)CH2SO2NHC2H5CH(CH3)CH2SO2N(CH3)2CH(CH3)CH2SO2N(C2H5)2CH(CH3)CH2P(=O)(OCH3)2C(CH3)2CH2P(=O)(OCH3)2CH(CH3)CH2P(=O)(OC2H5)2C(CH3)2CH2P(=O)(OC2H5)2C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SOCH3C(CH3)2CH2SO2CH3C(CH3)2CH2SCH3C(CH3)2CH2SOCH3C(CH3)2CH2SO2CH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3 | 3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-IH3-F3-Cl3-Cl3-Cl3-Br3-Br3-Br3.4-Cl24-Cl4-Br4-I4-Cl3-CH33-C2H53-i-C3H73-CF33-CH=CH23-C≡CH3-C≡CC(CH3)33-C≡CCF33-NO23-NH23-N(CH3)2 | 2-Cl2-CI2-Cl2-Cl2-Cl2-Cl2-Cl2-Cl2-Cl2-Cl2-Cl2-Cl2-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH3 |
表1(续)
编号 | R1 | Xm | Yn | 熔点(℃) |
1-4201-4211-4221-4231-4241-4251-4261-4271-4281-4291-4301-4311-4321-4331-4341-4351-4361-4371-4381-4391-4401-4411-4421-4431-4441-4451-4461-4471-4481-4491-4501-4511-4521-4531-4541-4551-4561-4571-4581-459 | C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SOCH3C(CH3)2CH2SO2CH3C(CH3)2CH2SCH3C(CH3)2CH2SOCH3C(CH3)2CH2SO2CH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3 | 3-NHCOCH33-NHCOCF33-NHCO2CH33-NHSO2CH33-NHSO2CF33-OCH33-OCF33-OCOCH33-OCOCF33-OCONHCH33-OCON(CH3)23-SCH33-SOCH33-SO2CH33-SCF33-SOCF33-SO2CF33-OSO2CH33-OSO2CF33-CH=CHCH=CH-43-OCH2O-43-OCF2O-43-OCF2CF2O-4H3-F3-Cl3-Cl3-Cl3-Br3-Br3-Br3.4-Cl23-CF33-NO23-OCF33-SCF33-OSO2CH33-OSO2CF33-I3-I | 2-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-Cl2-Cl2-Cl2-Cl2-Cl2-Cl2-Cl2-Cl2-Cl2-Cl2-Cl2-Cl2-Cl2-Cl2-ClHH | 231-232119-122 |
表1(续)
编号 | R1 | Xm | Yn | 熔点(℃) |
1-4601-4611-4621-4631-4641-4651-4661-4671-4681-4691-4701-4711-4721-4731-4741-4751-4761-4771-4781-4791-4801-4811-4821-4831-4841-4851-4861-4871-4881-4891-4901-4911-4921-4931-4941-4951-4961-4971-4981-4991-500 | C(CH3)2CH2SCH3C(CH3)2CH2SCH3CH(CH3)CH2SCH3CH(CH3)CH2SCH3CH(CH3)CH2SCH3CH(CH3)CH2SCH3CH(CH3)CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH3SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3CH(CH3)CH2SCH3CH(CH3)CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3 | 3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I | H3-CH32.3-(CH3)22.5-(CH3)22.6-(CH3)22-(CH2)3-32-(CH2)4-32-C2H52-n-C3H72-i-C3H72-t-C4H92-CH2OH2-CH2OCH32-CH2SCH32-CH2SOCH32-CH2SO2CH32-Ph2-F2-Cl-3-F2.3-Cl22.5-Cl22-Br2-I2-CF32-CHO2-COCH32-CN2-CF32-OCH32-OCF32-OCH2O-32-OCF2O-32-SCH32-NO22-N(CH3)22-CH3-3-F2-CH3-5-F2-CH3-3-Cl2-CH3-5-Cl2-CH3-3-OH2-CH3-3-OCH3 | 118-121 |
通式(I-3)
表2
编号 | R1 | R2 | R3 | Xm | Yn | 熔点(℃) |
2-12-22-32-42-52-62-72-82-92-102-112-122-132-142-152-162-172-182-192-202-212-222-232-242-222-232-24 | CH3C2H5C2H5C2H5n-C3H7n-C3H7n-C3H7i-C3H7i-C3H7i-C3H7i-C3H7i-C3H7i-C3H7i-C3H7i-C3H7i-C3H7CH2CH2SCH3CH2CH2SCH3CH(CH3)CH2SCH3CH(CH3)CH2SOCH3CH(CH3)CH2SO2CH3C(CH3)2CH2SCH3C(CH3)2CH2SOCH3C(CH3)2CH2SO2CH3C(CH3)2CH2SCH3C(CH3)2CH2SOCH3C(CH3)2CH2SO2CH3 | CH3CH3C2H5C2H5CH3C2H5n-C3H7CH3C2H5HCOCH3HCH3CH3CH3HCH3C2H5HHHHHHHHH | HHHHHHHHHCH3CH3C2H5CH3COCH3HCH3HHCH3CH3CH3CH3CH3CH3C2H5C2H5C2H5 | 3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I | 2-CH32-CH32-CH32-Cl2-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-Cl2-Cl2-CH32-CH32-CH32-CH32-CH3HHHHHH | 54-5686-8881-83 |
表2(续)
编号 | R1 | R2 | R3 | Xm | Yn | 熔点(℃) |
2-252-262-272-282-292-302-312-322-332-342-352-362-372-382-392-402-412-42 | C(CH3)2CH2SCH3C(CH3)2CH2SOCH3C(CH3)2CH2SO2CH3C(CH3)2CH2SCH3C(CH3)2CH2SOCH3C(CH3)2CH2SO2CH3CH(CH3)CH2SC2H5CH(CH3)CH2SOC2H5CH(CH3)CH2SO2C2H5CH(CH3)CH2SCH3CH(CH3)CH2SOCH3CH(CH3)CH2SO2CH3C(CH3)2CH2SCH3C(CH3)2CH2SOCH3C(CH3)2CH2SO2CH3CH(CH3)CH2SC2H5CH(CH3)CH2SOC2H5CH(CH3)CH2SO2C2H5 | HHHHHHHHHHHHHHHHHH | CH3CH3CH3C2H5C2H5C2H5CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | 3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I | 2-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-CH32-Cl2-Cl2-Cl2-Cl2-Cl2-Cl2-Cl2-Cl2-Cl |
通式(I-4)
表3(R2=R3=H)
编号 | R1 | Xm | Yn | 熔点(℃) |
3-13-23-33-43-53-63-73-83-9 | i-C3H7CH(CH3)CH2SCH3CH(CH3)CH2SOCH3CH(CH3)CH2SO2CH3C(CH3)2CH2SCH3C(CH3)2CH2SOCH3C(CH3)2CH2SO2CH3CH(CH3)CH2SCH3C(CH3)2CH2SCH3 | 3-I3-I3-I3-I3-I3-I3-I3-I3-I | HHHHHHH2-CH32-CH3 | 170-171115-118120-123 |
表3(续)
编号 | R1 | Xm | Yn | 熔点(℃) |
3-103-113-123-133-143-153-163-173-183-193-203-213-223-233-243-253-263-273-283-293-303-313-323-333-343-353-363-373-383-393-403-413-423-433-44 | CH(CH3)CH2SCH3C(CH3)2CH2SCH3CH(CH3)CH2SCH3C(CH3)2CH2SCH3CH(CH3)CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SOCH3C(CH3)2CH2SO2CH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3C(CH3)2CH2SCH3 | 3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I3-I | 6-CH36-CH32-C2H52-C2H56-C2H56-C2H52-CH2SCH32-CH2SOCH32-CH2SO2CH36-GH2SCH36-CH2SOCH36-CH2SO2CH32-F6-F2-Cl2-Cl2-Cl4-Cl6-Cl2-Br4-Br6-8r2-I4-I6-I2-CN6-CN2.4-Cl24.6-Cl22.4-Br22-Cl-4-Br2-Cl-4-I2-CH3-4-Cl2-CH3-4-Br2-CH3-4-I | 205204221 |
具体实施方式
下面是本发明的典型实施例,但本发明并不限于此。
实施例1.N1-(2-氯-4-五氟硫烷基(sulfanyl)苯基)-N2-(1,1-二甲基-2-甲硫基乙基)-3-碘邻苯二甲酰胺(化合物1-372)的制备
将750mg(2.0mmol)N-(1,1-二甲基-2-甲硫基乙基)-6-碘代邻苯二甲酸异酰亚胺溶解于10ml乙腈中,添加510mg(2.0mmol)2-氯-4-五氟烷硫基苯胺和10mg三氟乙酸,混合物在室温下搅拌2小时。过滤收集沉淀的晶体,用少量乙醚洗涤,获得1.0g所需产物。
产率:79%
物理性质:熔点170-173℃。
实施例2.N1-(2-氯-4-五氟硫烷基苯基)-N2-(1,1-二甲基-2-甲基磺酰基乙基)-3-碘邻苯二甲酰胺(化合物1-374)的制备
将0.63g(1.0mmol)N1-(2-氯-4-五氟硫烷基苯基)-N2-(1,1-二甲基-2-甲硫基乙基)-3-碘邻苯二甲酰胺溶解于10ml氯仿中,将混合物冷却至0℃。向溶液中添加0.38g(2.2mmol)间-氯过苯甲酸。搅拌1小时后,将反应混合物溶液用硫代硫酸钠水溶液和10%碳酸钾水溶液洗涤,过无水硫酸镁干燥,减压蒸馏除去溶剂,获得0.55g所需产物。
产率:84%
物理性质:熔点196-198℃。
含有本发明通式(I)代表的邻苯二酰胺衍生物作为活性成分的农业园艺业杀虫剂适用于防治各种害虫虫害如农业园艺业害虫、储藏谷物害虫、卫生害虫、线虫等,这些害虫对水稻、果树、蔬菜、其他作物、花卉、观赏植物等有害。上述杀虫剂具有显著的杀虫作用,例如对鳞翅目,包括棉褐带卷蛾(Adoxophyes orana fasciata)、茶小卷夜蛾(褐带卷蛾属)、苹小食心虫(Grapholita inopinata)、梨小食心虫(Grapholita molesta)、大豆食心虫(Leguminivoraglycinivorella)、桑小卷蛾(Olethreutes mori)、茶细蛾(Caloptilia thevivora)、猛花细蛾(Caloptilia zachrysa)、金纹小潜细蛾(Phyllonorycter ringoniella)、梨潜皮细蛾(Spulerrinaastaurota)、菜粉蝶日本亚种(Piers rapae crucivora)、烟实夜蛾(Heliothis属)、苹果皮小卷蛾(Laspevresia pomonella)、小菜蛾(Plutella xylostella)、苹果银蛾(Argyresthia conjugella)、桃柱果蛾(Carposina niponensis)、二化螟(Chilo suppressalis)、稻纵卷叶野螟(Cnaphalocrocia medinalis)、烟草粉斑螟(Ephestiaeluteia)、桑绢野螟(Glyphodes pyloalis)、三化螟(Scirpophagaincertulas)、直纹稻弄蝶(Parnara guttata)、粘虫(Pseudaletiaseparata)、稻蛀茎夜蛾(Sesamia inferens)、斜纹贪夜蛾(Spodoptera litura)、贪夜蛾(Spodoptera egigua)等;半翅目,包括二点叶蝉(Macrosteles fascifrons)、黑尾叶蝉(Nephotettixcincticepts)、褐飞虱(Nilaparvata lugens)、白背飞虱(Sogatellafurcifera)、橘木虱(Diaphorina citri)、日本葡萄粉虱(Aleurolobus taonabae)、甘薯粉虱(Bemisia tabaci)、温室粉虱(Trialeurodes vaporariorum)、萝卜蚜(Lipaphis erysimi)、桃蚜(Myzus persicae)、角蜡蚧(Ceroplastes ceriferus)、橘棉蚧(Pulvinaria aurantii)、樟网盾蚧(Pseudaonidia duplex)、圣琼斯康盾蚧(Comstockaspis perniciosa)、矢尖盾蚧(Unaspisyanonensis)等;垫忍线虫科,包括根斑线虫(Pratylenchus sp.)、多色异丽金龟(Anomala rufocuprea)、日本弧丽金龟(Popillajaponica)、烟草窃蠹(Lasioderma serricorne)、褐粉蠹(Lyctusbrunneus)、马铃薯瓢虫(Epilachna vigintiotopunctata)、绿豆象(Callosobruchus chinensis)、番茄象(Listroderescostirostris)、玉米象(Sitophilus zeamais)、棉铃象(Anthonomusgrandis grandis)、稻水象(Lissorhoptrus oryzophilus)、黄守瓜(Aulacophora femoralis)、水稻负泥虫(Oulema oryzae)、黄曲条菜跳甲(Phyllotreta striolata)、纵坑切梢小蠹(Tomicuspiniperda)、马铃薯叶甲(Leptinotarsa decemlineata)、墨西哥豆瓢虫(Epilachna varivestis)、南瓜十二星叶甲(Diabrotica sp.)等;双翅目,包括瓜寡鬃实蝇(Dacus(Zeugodacus)cucurbitae)、橘果实蝇(Dacus(Bactrocera)dorsalis)、大麦毛眼水蝇(Agromyzaoryzae)、葱地种蝇(Delia antiqua)、灰地种蝇(Delia platura)、大豆英瘿蚊(Asphondylia sp.)、家蝇(Musca domestica)、尖音库蚊(Culex pipiens pipiens)等;和垫刃线虫科,包括咖啡短体线虫(Pratylenchus coffeae)、马铃薯金线虫(Glaboderarostchiensis)、根结线虫(Meloidogyne sp.)、半穿刺线虫(Tylenchulus semipenetrans)、Aphelenchus sp.(Aphelenchusavenae)、菊叶芽滑刃线虫(Aphelenchoides ritzemabosi)等;和蜱螨目,包括柑桔全爪螨(Panonychus citri)、苹果全爪螨(Panonychusuimi)、朱砂叶螨(Tetranychus cinnabarinus)、神泽叶螨(Tetranychus Kanzawai Kishida)、二点叶螨(Tetranychus urticaeKoch)、茶尖叶瘿螨(Acaphylla theae)、桔刺皮瘿螨(Aculopspelekassi)、龙首丽瘿螨(Calacarus carinatus)、梨上瘿螨(Epitrimerus pyri)等。
含有本发明的通式(I)代表的邻苯二酰胺衍生物作为活性成分的农业园艺业杀虫剂对上述种类的危害水田作物、旱田作物、果树、蔬菜、其他作物、花卉和观赏植物等的害虫有显著的杀虫作用。因此,将本发明的农业园艺业杀虫剂施用到苗圃设施;水田;旱田;水果、蔬菜、其他作物、花卉和观赏植物的种子或茎和叶;培养基质如水田水、土壤等;在预期害虫出现的季节、其出现前或确认其出现时,可以获得本发明农业园艺业杀虫剂的所需效果。特别是,用于使用本发明农业园艺业杀虫剂的优选施药方式是采用所谓的“渗透和易位”的施药方式,其中将本发明的农业园艺业杀虫剂施用到作物、花卉和观赏植物等的苗圃土壤;移栽时的picking-in hole土壤;植物根部;灌溉水;或水培的培养水,以便使本申请的化合物通过或不通过土壤从根部被吸收。
本发明的农业园艺业杀虫剂通常按照常规的制备农业化学品的方式被制备成常规使用的形式。
也就是说,将通式(I)代表的邻苯二酰胺衍生物和任选的助剂与适宜的惰性载体以合适的比例混合,并通过溶解、分散、悬浮、混合、浸渍、吸附或粘着制备成适宜的制剂形式如悬浮剂、乳油、胶悬剂、可湿性粉剂、粒状可湿性粉剂、颗粒剂、粉剂、片剂、药包等。
可用于本发明的惰性载体可以是固体或液体。可用作固体载体的材料包括大豆粉、谷物粉、木粉、树皮粉、锯屑、烟草茎粉、胡桃壳粉、糠、纤维素粉、蔬菜提取残余物、合成聚合物如合成树脂粉、粘土(例如高岭土、膨润土和酸性粘土)、滑石(例如滑石和叶蜡石)、二氧化硅(例如硅藻土、硅沙、云母和白炭[合成的、高度分散的硅酸,也称为细分散的水合二氧化硅或水合硅酸,有些市售产品含有硅酸钙为主要成分])、活性炭、硫磺粉、浮石、煅烧硅藻土、砖粉、粉煤灰、沙、碳酸钙、磷酸钙和其他无机或矿物粉、塑料载体如聚乙烯、聚丙烯、聚(偏二氯乙烯)、化学肥料如硫酸铵、磷酸铵、硝酸铵、脲和氯化铵和堆肥。这些载体可单独或作为其混合物使用。
可用作液体载体的物质选自本身具有溶解性或虽不具有上述溶解性但借助于助剂能够分散活性成分的物质。下列物质是液体载体的典型实例,并且可以单独或作为其混合物使用:水,醇类(例如甲醇、乙醇、异丙醇、丁醇和乙二醇),酮类(例如丙酮、甲乙酮、甲基异丁酮、二异丁酮和环己酮),醚类(例如乙醚、二烷、溶纤剂、二丙醚和四氢呋喃),脂族烃(例如煤油和矿物油),芳族烃(例如苯、甲苯、二甲苯、溶剂石脑油和烷基萘),卤代烃(例如二氯乙烷、氯仿、四氯化碳和氯苯),酯类(例如乙酸乙酯、邻苯二甲酸二异丙酯、邻苯二甲酸二丁酯和邻苯二甲酸二辛酯),酰胺类(例如二甲基甲酰胺、二乙基甲酰胺和二甲基乙酰胺),腈类(例如乙腈)和二甲基亚砜。
下面是其他助剂的典型实例,根据目的而使用,并且可以单独或有时以其组合使用,或根本不需使用。
为了乳化、分散、溶解和/或湿润作为活性成分的化合物,使用表面活性剂。表面活性剂的实例包括聚氧乙烯烷基醚、聚氧乙烯烷基芳基醚、聚氧乙烯高级脂肪酸酯、聚氧乙烯树脂酸酯、聚氧乙烯脱水山梨醇一月桂酸酯、聚氧乙烯脱水山梨醇一油酸酯、烷基芳基磺酸盐、萘磺酸缩合产物、木质素磺酸盐和高级醇硫酸酯。
此外,为了稳定作为活性成分的化合物的分散体、使之增粘和/或粘合之,还可使用下文例举的助剂,即,还可使用助剂如酪蛋白、明胶、淀粉、甲基纤维素、羧甲基纤维素、阿拉伯胶、聚(乙烯醇)、松节油、糠油、膨润土和木质素磺酸盐。
为了改善固体产品的可流动性,还可使用下列助剂,即,可使用助剂如蜡、硬脂酸盐、磷酸烷基酯等。
助剂如萘磺酸缩合产物和磷酸酯的缩聚物可用作可分散产品的胶溶剂。
助剂如硅油还可用作消泡剂。
助剂如1,2-苯并异噻唑啉-3-酮、对-氯-间-二甲苯酚、对羟基苯甲酸丁酯还可用作防腐剂。
此外,必要时,还可添加功能性展着剂(functional spreadingagents)、活性增效剂如代谢分解抑制剂如胡椒基丁醚、防冻剂如丙二醇、抗氧化剂如BHT、紫外线吸收剂等。
作为活性成分的化合物的含量可根据需要变化,作为活性成分的化合物可以以合适的比例使用,其可以在0.01-90重量份/100份农业园艺业杀虫剂范围内加以选择。例如,在粉剂或颗粒剂中,作为活性成分的化合物的适宜含量是0.01-50重量%。在乳油或可湿性粉剂中,也是0.01-50重量%。
本发明的农业园艺业杀虫剂可用于以下列方式防治各种害虫:按原状或用水等适当地稀释或悬浮后,以防治害虫有效量将其施用到预期会出现害虫的作物上,或不希望出现害虫的场所。
本发明农业园艺业杀虫剂的用量根据各种因素如目的、需防治的害虫、植物的生长阶段、害虫出现的趋势、天气、环境条件、制剂形式、施用方法、施药场所和施药时间而变化。根据目的,可在每10公亩0.001g-10kg(以作为活性成分的化合物计),优选0.01g-1kg范围内进行适当地选择。
本发明的农业园艺业杀虫剂可与其他农业园艺业杀虫剂、杀螨剂、杀线虫剂、杀真菌剂、生物农药等混合使用以便拓宽可防治害虫种类谱和延长有效施药时间或降低剂量。此外,根据施药情况,本发明的农业园艺业杀虫剂可与除草剂、植物生长调节剂、肥料等混合使用。
作为用于上述目的的其他的农业园艺业杀虫剂、杀螨剂和杀线虫剂,可例举的农业园艺业杀虫剂、杀螨剂和杀线虫剂如乙硫磷、敌百虫、甲胺磷、高灭磷、敌敌畏、速灭磷、久效磷、马拉松、乐果、安果、灭蚜磷、蚜灭多、甲基乙拌磷、乙拌磷、异砜磷、二溴磷、甲基一六零五、杀螟松、杀螟腈、丙虫磷、倍硫磷、丙硫磷、丙溴磷、丙胺磷、双硫磷、稻丰散、甲基毒虫畏、毒虫畏、杀虫畏、腈肟磷、异唑磷、吡唑硫磷、杀扑磷、毒死蜱、甲基毒死蜱、打杀磷、二嗪农、虫螨磷、伏杀磷、亚胺硫磷、杀抗松、喹喔啉、特丁磷、灭克磷、硫线磷、甲亚砜磷、DPS(NK-0795)、乙丙磷威、克线磷、Isoamidophos、噻唑酮磷、氧唑磷、灭克磷、倍硫磷、伐线丹、除线磷、硫磷嗪、乙丙硫磷、丰索磷、除线特、除虫菊酯、丙烯聚酯、炔酮菊酯、苄呋菊酯、氯菊酯、七氟菊酯、氟氯菊酯、甲氰菊酯、氯氰菊酯、α-氯氰菊酯、氯氟氰菊酯、λ-氯氟氰菊酯、溴氰菊酯、氟酯菊酯、杀灭菊酯、高氰戊菊酯、氟氰戊菊酯、氟胺氰菊酯、乙氰菊酯、醚菊酯、卤醚菊酯、灭虫硅醚、灭多虫、甲氨叉威、硫双灭多威、涕灭威、棉铃威、巴丹、速灭威、灭杀威、残杀威、Xylylcarb、Propoxur、Phenoxycarb、丁苯威、苯虫威、苯硫威、联苯肼酯、BPMC、西维因、抗蚜威、虫螨威、丁硫克百成、呋线威、丙硫克百威、砜灭威、杀螨硫隆、氟脲杀、伏虫隆、氟铃脲、双苯氟脲、氟丙氧脲、氟虫脲、定虫隆、杀螨锡、三环锡、油酸钠、油酸钾、蒙五一五、蒙五一二、乐杀螨、虫螨脒、开乐散、Kersen、Chrorobenzilate、溴螨酯、三氯杀螨砜、杀虫磺、苯螨特、双苯酰肼、甲氧苯酰肼、环虫酰肼、克螨特、杀螨醌、硫丹、茂醚、氟唑虫清、唑螨酯、唑虫酰胺、锐劲特、吡螨胺、唑蚜威、特苯唑、噻螨酮、烟碱、硝胺烯啶、吡虫清、噻虫啉、吡虫啉、噻虫嗪、噻虫胺、呋虫胺、氟啶胺、蚊蝇醚、灭蚁腙、嘧胺苯醚、哒螨酮、灭蝇胺、TPIC(异氰脲酸三丙酯)、拒嗪酮、四螨嗪、噻嗪酮、硫环杀、喹螨醚、灭螨猛、二唑虫、复合杀螨霉素、米尔螨素、齐墩螨素、埃玛菌素、艾克敌105、BT(苏云金芽孢杆菌)、艾扎丁、鱼藤酮、羟丙基淀粉、保松噻、威百亩、Morantel tartrate、棉隆、杨菌胺、侵入巴斯德氏芽菌、Monacrosporium-phymatophagum等。作为用于上述相同目的的农业园艺业杀真菌剂,可例举的农业园艺业杀真菌剂如硫、石灰硫、碱性硫酸铜、异稻瘟净、克瘟散、甲基立枯磷、福美双、福代锌、代森锌、代森锰、代森锰锌、甲基代森锌、托布津、甲基托布津、苯菌灵、双胍辛醋酸盐、双八胍盐、丙氧灭锈胺、氟酰胺、戊菌隆、呋吡唑灵、溴氟唑菌、甲霜灵、霜灵、氯环丙酰胺、抑菌灵、磺菌胺、百菌清、亚胺菌、氰菌胺(NNF-9425)、Himexazole、氯唑灵、氟菌安、杀菌利、烯菌酮、异丙定、三唑酮、氟菌唑、双苯三唑醇、氟菌唑、环戊唑醇、氟康唑、丙环唑、Diphenoconazole、腈菌唑、氟醚唑、己唑醇、戊唑醇、酰胺唑、丙氯灵、稻瘟酯、环唑醇、富士一号、异嘧菌醇、二甲嘧菌胺、嘧菌胺、啶斑肟、氟啶胺、嗪氨灵、哒菌清、腈嘧菌酯、代森环、克菌丹、噻菌灵、噻二唑素-S-甲基(CGA-245704)、四氯苯酞、三环唑、咯喹酮、灭螨猛、喹菌酮、二嗪农、Trifloxystrobin、Cyazofamid、Thiadinil、Dichlosimet、春雷霉素、有效霉素、多氧霉素、灭瘟素、链霉素等。同样地,作为除草剂,可例举的除草剂如草甘膦、草硫膦、草甘双膦、双丙氨酰膦、草铵膦、禾草畏、苄草丹、杀草丹、稗草畏、黄草灵、利谷隆、香草隆、苄嘧磺隆、环丙磺隆、醚磺隆、吡嘧磺隆、四唑磺隆、啶咪磺隆、Tenylchlor、草不绿、丙草胺、稗草胺、乙苯酰草、苯噻草胺、胺硝草、治草醚、氟锁草醚、乳氟禾草灵、氰氟草酯、碘苯腈、溴丁酰草胺、枯杀达、稀禾啶、草萘胺、茚草酮、吡唑特、吡草酮、氟唑草酯、灭草烟、磺胺草唑、唑草胺、Bentoxazon、草灵、对草快、敌草快、肟啶草、西玛津、阿特拉津、戊草津、苯氧丙氨津、Benflesate、达草氟、喹禾灵、Bentazon、Oxaziclomefone、Azafenidin、噻草平、过氧化钙等。
至于生物农药,使用本发明的农业园艺业杀虫剂混合例如下列物质预期可以获得与上述相同的效果:从细胞核多角体病毒(NPV)、微粒子病病毒(GV)、细胞质多角体病毒(CPV)、昆虫痘病毒(EPV)等获得的病毒制剂;用作杀虫剂或杀线虫剂的微生物农药,例如Monacrosporium phymatophagum、小卷蛾斯氏线虫、Steinernemakushidai、侵入巴斯德氏芽菌等;用作杀真菌剂的微生物农药,例如木质素木霉(Trichoderma lignorum)、 放射形土壤杆菌(Agrobacterium radiobactor)、非致病的胡萝卜欧文氏杆菌(Erwinia carotovora)、枯草芽孢杆菌(Baccillus subtilis)等;和用作除草剂的生物农药,例如田野黄单孢菌(Xanthomonascampestris)等。
另外,本发明的农业园艺业杀虫剂可以与生物农药结合使用,所述生物农药包括天敌,例如寄生蜂(丽恩蚜小蜂)、寄生蜂(蚜茧蜂)、Gall-mildge(Aphidoletes aphidimyza)、寄生蜂(潜蝇姬小蜂)、寄生螨(西伯利亚离颚茧蜂)、捕食螨(智利小植绥螨)、捕食螨(黄瓜钝绥螨)、捕食虫(东亚小花蝽)等;微生物农药,例如布氏白僵菌等;和性外激素类,例如(Z)-10-十四碳烯基=乙酸酯,(E,Z)-4,10-十四碳烯二烯基=乙酸酯,(Z)-8-十二碳烯=乙酸酯,(Z)-11-十四碳烯基=乙酸酯,(Z)-13-二十碳烯-10-酮,(Z)-8-十二碳烯基=乙酸酯,(Z)-11-十四碳烯基=乙酸酯、(Z)-13-二十碳烯-10-酮、14-甲基-1-十八碳烯等。
下面描述了本发明的典型制剂实施例和试验实施例,但其不应被解释为是对本发明范围的限制。
制剂实施例中所用的术语“份”以重量计。
制剂实施例1
表1-3中所列各化合物 10份
二甲苯 70份
N-甲基吡咯烷酮 10份
聚氧乙烯壬基苯基醚和烷基苯磺酸钙的混合物 10份
将上述成分均匀混合进行溶解,制得乳油。
制剂实施例2
表1-3所列各化合物 3份
粘土粉 82份
硅藻土粉 15份
将上述成分均匀混合并研磨,制得粉剂。
制剂实施例3
表1-3所列各化合物 5份
膨润土和粘土的混合粉 90份
木质素磺酸钙 5份
将上述成分均匀混合,将所得混合物与适量的水一起捏合,然后造粒并干燥,制得颗粒剂。
制剂实施例4
表1-3所列各化合物 20份
高岭土和合成的高分散硅酸 75份
聚氧乙烯壬基苯基醚和烷基苯磺酸钙的混合物 5份
将上述成分均匀混合并研磨,制得可湿性粉剂。
试验实施例1:对小菜蛾(Plutella xylostella)的杀虫测试
将小菜蛾成虫释出,使其在中国卷心菜幼苗上产卵。释放后两天,将有卵沉积的幼苗浸在液体化学品中约30秒,所述液体化学品是通过对含表1-3中所列各化合物为活性成分的制剂进行稀释,调节其浓度至50ppm而制得的。风干后,将其放置在恒温25℃的房间内。浸药后六天,统计孵化的昆虫数。按照下列方程计算死亡率,按照下文所示标准评价杀虫效果。试验进行三组重复,每组10只昆虫。
标准:
A---死亡率100%
B---死亡率99-90%
C---死亡率89-80%
D---死亡率79-50%
E---死亡率49%或更低
结果示于下表4中。
试验实施例2:对斜纹贪夜蛾(Spodoptera litura)的杀虫测试
将一片卷心菜叶(栽培品种:Shikidori)浸在液体化学品中约30秒,所述液体化学品是通过对含表1-3中所列各化合物为活性成分的制剂进行稀释,调节其浓度至50ppm而制得的。风干后,将其放置在直径9cm的塑料培替氏培养皿中并用斜纹贪夜蛾的二龄幼虫接种,之后盖上培养皿,然后放置在恒温25℃的房间内。接种后八天,统计死的和活的昆虫数。按照下列方程计算死亡率,按照试验实施例1中所示标准评价杀虫效果。试验进行三组重复,每组10只昆虫。
结果示于下表4中。
试验实施例3:对茶小卷蛾(褐带卷蛾属)的杀虫测试
将茶叶浸在液体化学品中约30秒,所述液体化学品是通过对含表1-3中所列各化合物为活性成分的制剂进行稀释,调节其浓度至50ppm而制得的。风干后,将茶叶放置在直径9cm的塑料培替氏培养皿中并用茶小卷蛾幼虫接种,之后将培养皿放置在恒温25℃和湿度70%的房间内。接种后八天,统计死的和活的幼虫数。按照试验实施例2中所示方程计算死亡率,按照试验实施例1中所示标准评价杀虫效果。试验进行三组重复,每组10只昆虫。
结果示于下表4中。
表4
编号 | 试验实施例1 | 试验实施例2 | 试验实施例3 |
1-2901-2921-2961-2971-2981-3721-3741-4581-4591-4602-222-232-243-53-63-73-243-26 | AAAAAAAAAAAAAAAAAA | AAAAAAAAAAAAAEDAAA | AAAAAAAAAAAEAAEAAA |
Claims (3)
1.一种通式(I)代表的邻苯二酰胺衍生物:
其中R1代表C1-6烷基、C1-6烷硫基C1-6烷基、C1-6烷基亚磺酰基C1-6烷基或C1-6烷基磺酰基C1-6烷基;R2和R3代表氢;X代表卤素;m代表1;Y代表卤素或C1-6烷基;n代表0-2的整数。
2.一种农业园艺业杀虫剂,其特征在于含有权利要求1所述的邻苯二酰胺衍生物作为活性成分。
3.农业园艺业杀虫剂的使用方法,其特征在于将有效量的权利要求2所述农业园艺业杀虫剂用于需保护作物或土壤中,以保护有益作物免于害虫虫害。
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US7317124B2 (en) | 2003-11-13 | 2008-01-08 | Sanofi-Aventis Deutschland Gmbh | Ortho-substituted pentafluorosulfanylbenzenes, process for their preparation and their use as valuable synthetic intermediates |
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