CN1037965C - 新的三唑衍生物及杀虫剂和杀螨剂 - Google Patents
新的三唑衍生物及杀虫剂和杀螨剂 Download PDFInfo
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- CN1037965C CN1037965C CN93106496A CN93106496A CN1037965C CN 1037965 C CN1037965 C CN 1037965C CN 93106496 A CN93106496 A CN 93106496A CN 93106496 A CN93106496 A CN 93106496A CN 1037965 C CN1037965 C CN 1037965C
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
一种新的具有通式(Ⅰ)的、用作杀虫剂或杀螨剂的三唑衍生物。它可控制多种有害昆虫和螨类,特别是螨类和蚜虫,而不会对作物造成伤害。
(其中R1是一个烷基,X是一个氢原子,卤原子,烷基或类似基团,n值为1-5的整数,Y是一个烯基,炔基,烷氧基烷基或类似基团)。
Description
本发明涉及新的三唑衍生物以及包含它们作为活性组分的杀虫剂和杀螨剂。
日本专利公开号56-154464和DE-A-363-1511公开了多种具有杀虫和杀螨活性的三唑衍生物。但是,还不能说在这些专利说明书中所描述的化合物的杀虫和杀螨活性是令人满意的。
直到现在,有许多种化合物,诸如有机磷化合物,有机锡化合物及类似的化合物,被用来控制农场和园艺作物中的害虫和螨。但是这些化合物已经使用了很多年,以致上述有害昆虫已对这些化学品产生了一定程度的耐药性,並且近来已难于控制这些害虫。特别是,这一趋势在鳞翅目害虫、螨和蚜虫中变得十分明显並已成为严重的问题。结果,急需发展新型的、具有不同功能的杀虫剂和杀螨剂。
本发明人已经进行了种种研究,用来开创新的、对多种有害昆虫具有很高效力並能安全使用的杀虫剂和杀螨剂,它们还从来没有在普通的技术中被发现,因而可望开发出具有与普通技术得到的产品性能不同的杀虫剂和杀螨剂。
进一步,发明人已经合成了许多三唑衍生物並检验了它们的生理活性。结果,发明人发现具有后面要叙述的通式〔I〕的新的三唑衍生物对许多农场和园艺作物中的有害昆虫具有优良的杀虫效果,特别是对鳞翅目的有害昆虫、螨和蚜虫;並且对那些对通常的化学品已有耐药性的螨的卵和幼虫以及蚜虫的幼虫也有很高的药效,本发明已经完成。
按照本发明,可提供具有下列通式〔I〕的三唑衍生物:〔其中R1是一个烷基,x是一个氢原子,卤原子,烷基,烷氧基,烷硫基,硝基,氰基或三氟甲基,n值是1-5的整数,若当n值是2或更大时,X可以是相同或不同的原子或基团的任意组合;Y是一个烯基,炔基,烷氧基烷基,烷氧基烷氧基,烷硫基烷基,环烷基,环烷基烷氧基,环烷基烷基,环烷基烯基,环烷基炔基,三烷基甲硅烷基烷基,三烷基甲硅烷基烷氧基,含有不少于7个碳原子数的烷基,含有不少于7个碳原子数的烷氧基,含有不少于7个碳原子数的烷硫基,含有不少于7个碳原子数的烷基亚磺酰基,含有不少于7个碳原子数的烷基磺酰基,或一个可被下列通式(1)表示的基团:(其中A是一个氧原子,硫原子,低级亚烷基,低级亚烷基氧基,氧一低级亚烷基或一个低级亚烷基氧亚烷基,k值为0或1,Q是CH或一个氮原子,R2是一个氢原子,卤原子,烷基,烷氧基,三氟甲基或三氟甲氧基,m是1-5的整数,假如当m值是2或更大时,R2可以是相同或不同原子或基团的任意组合)〕。
进一步,本发明还提供包含上述三唑衍生物作为活性组分的杀虫剂和杀螨剂。
在整个专利说明书中,术语“低级的”是指加有这一术语的基团中的碳原子数目不超过6。
进一步,术语“烷基”是指含有1-30个碳原子数的直链或叉链烷基,例如,甲基,乙基,正丙基,异丙基,正丁基,异丁基,第二丁基,叔丁基,正戊基,异戊基,新戊基,正己基,异己基,3,3-二甲基丁基,正庚基,5-甲基己基,4-甲基己基,3-甲基己基,4,4-二甲基戊基,正辛基,6-甲基庚基,正壬基,7-甲基辛基,正癸基8-甲基壬基,正十一碳烷基,9-甲基癸基,正十二碳烷基,10-甲基十一碳烷基,正十三碳烷基,11-甲基-十二碳烷基,正十四碳烷基,12-甲基-十三碳烷基,正十五碳烷基,13-甲基-十四碳烷基,正十六碳烷基,正十七碳烷基,正十八碳烷基,正十九碳烷基,正廿碳烷基及类似的基团。
术语“烷氧基”,“烷硫基”,“烷基亚磺酰基”和“烷基磺酰基”是指(烷基)-O-基,(烷基)-S-基,(烷基)-SO-基和(烷基)-SO2-基,其中烷基部分的意义各自与上面叙述的相同。
术语“卤原子”是指氟,氯,溴和碘。
术语“烯基”是指含有2-20个碳原子数的直链或叉链的烯基,它包括,例如,乙烯基,丙烯基,异丙烯基,丁烯基,戊烯基,己烯基,庚烯基,辛烯基,3-甲基-1-丁烯基,4-甲基-1-戊烯基和类似的基团。
术语“炔基”是指含有2-20个碳原子数的直链或叉链的炔基,它包括,例如,乙炔基,丙炔基,丁炔基,戊炔基,己炔基,3,3-二甲基-1-丁炔基,4-甲基-1-戊炔基,3-甲基-1-戊炔基 5-甲基-1-己炔基4-甲基-1-己炔基,3-甲基-1-己炔基,庚炔基,辛炔基,壬炔基,癸炔基,十一碳炔基,十二碳炔基,十三碳炔基,十四碳炔基,十五碳炔基,十六碳炔基以及类似的基团。
术语“环烷基”是指含有3-12个碳原子数的环烷基,它包括,例如,环丙基,环丁基,环戊基,环己基,环庚基,环辛基以及类似的基团。
术语“环烷基烷基”是指含有6-12个碳原子数的环烷基烷基,它包括,例如,环戊基甲基,环己基甲基,环戊基乙基,环己基乙基,环戊基丙基,环己基丙基,环己基戊基以及类似的基团。
术语“环烷基烷氧基”是指(环烷基烷基)-O-基团,其中的环烷基烷基部分的意义与上面叙述的相同。
术语“环烷基烯基”是指含有5-12个碳原子数的环烷基烯基,它包括,例如,环戊基乙烯基,环己基乙烯基 3-环戊基-1-丙烯基,3-环己基-1-丙烯基,5-环己基-1-戊烯基以及类似的基团。
术语“环烷基炔基”是指含有5-12个碳原子数的环烷基炔基,它包括,例如,环戊基乙炔基,环己基乙炔基,3-环戊基-1-丙炔基,3-环己基-1-丙炔基以及类似的基团。
术语“三(低级烷基)甲硅烷基低级烷基”包括,例如,三甲基甲硅烷基甲基,二甲基乙基甲硅烷基甲基,丁基二甲基甲硅烷基甲基以及类似的基团。
术语“三(低级烷基)甲硅烷基低级烷氧基”是指〔三(低级烷基)甲硅烷基低级烷基〕-O-基团,其中的三(低级烷基)甲硅烷基低级烷基部分具有与上面叙述的相同意义。
术语“低级亚烷基”是指含有1-4个碳原子数的直链或叉链的亚烷基,它包括,例如,-CH2-,-CH2-CH2-,-CH(CH3)-,-CH2-CH2-CH2-,-CH(CH3)CH2-,-C(CH3)2-,-CH2CH2CH2CH2-,-CH(CH3)CH2CH2-,-CH2CH(CH3)CH2-以及类似的基团。
术语“低级亚烷氧基”是指一(低级亚烷基)-O-基团,其中的低级亚烷基部分具有与上面叙述的相同意义。
术语“氧-低级亚烷基”是指-O-(低级亚烷基)-基团,其中的低级亚烷基部分具有与上面叙述的相同意义。
术语“低级亚烷基氧亚烷基”是指-(低级亚烷基)-O-(低级亚烷基)-基团,其中的低级亚烷基部分具有与上面叙述的相同意义。
以下叙述的具有通式〔I〕的化合物可作为本发明的优选化合物,即式〔I〕中的R1是具有1-6个碳原子数的直链或叉链的烷基,最好是甲基;x是一个氢原子,卤原子,有1-4个碳原子的直链或叉链烷基,硝基,氰基或三氟甲基,n值为1-3的整数,如果当n值是2或3,则X可以是相同或不同的原子或基团的任意组合;Y是含有7-20个碳原子数的直链或叉链烷基,含有3-12个碳原子数的环烷基,含有6-12个碳原子数的环烷基烷基,含有7-16个碳原子数的直链或叉链的烷氧基,含有7-12个碳原子数的环烷基烷氧基,含有7-16个碳原子数的直链或叉链的烷硫基,烷基亚磺酰基,烷基磺酰基,含有3-16个碳原子数的直链或叉链的烯基,含有5-12个碳原子数的环烷基烯基,含有3-16个碳原子数的直链或叉链的炔基,含有5-12个碳原子数的环烷基炔基,三(低级烷基)甲硅烷基低级烷基,三(低级烷基)甲硅烷基低级烷氧基或一个可被式(I)代表的基团(其中的A是一个氧原子,硫原子,含有1-4个碳原子数的低级亚烷基,亚甲基氧基或氧亚甲基,k值为0或1,Q是CH基或一个氮原子,R2是一个氢原子,卤原子,低级烷基,低级烷氧基,三氟甲基或三氟甲氧基,m值是1-3的整数,並且当m值是2或3时,R2可以是相同或不同原子或基团的任意组合)。
表1至10列出了按照本发明的具有通式〔I〕的化合物的具体实例。还有,化合物的编号是参照后面所描述的编号编排的。
表1
化合物编号 | R1 | Xn | Y | 熔点(℃)或折射率(nD 20) |
123456789101112131415161718192021222324 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | H2-F2-Cl2-Br2-I2,3,4,5,6-F52-CH32-OCH32-SCH32-CN2-NO22-CF32-Cl2,6-F22-Cl,6-F2-Cl2-Cl,6-F2,6-F22,6-Cl22-F2-Cl2-Br2-I2-CH3 | 4-C7H154-C7H154-C7H154-C7H154-C7H154-C7H154-C7H154-C7H154-C7H154-C7H154-C7H154-C7H154-C8H174-C8H174-C8H174-C9H194-C9H194-C9H194-C9H194-C10H214-C10H214-C10H214-C10H214-C10H21 | 1.58191.56501.58161.59241.60251.52521.58031.58401.600350.0-53.51.57801.54071.58001.55321.56521.57661.56121.55181.56981.55951.57081.57801.587548.0-50.0 |
表2
化合物编号 | R1 | Xn | Y | 熔点(℃)或折射率(nD 20) |
25262728293031323334353637383940414243444546474849505152 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | 2-OCH32-SCH32-CN2-NO22-CF32-Cl,6-F2,6-F22,6-Cl22,4,6-F32-Cl2-Cl,6-F2,6-Cl22,6-F22-Cl2-Cl,6-F2,6-F22,6-Cl22-Cl2-Cl,6-F2,6-F22,6-Cl22-Cl2-Cl,6-F2,6-F22,6-Cl22-Cl2-Cl,6-F2,6-F2 | 4-C10H214-C10H214-C10H214-C10H214-C10H214-C10H214-C10H214-C10H214-C10H214-C11H234-C11H234-C11H234-C11H234-C12H254-C12H254-C12H254-C12H254-C13H274-C13H274-C13H274-C13H274-C14H294-C14H294-C14H294-C14H294-C15H314-C15H314-C15H31 | 1.564937.0-40.055.0-58.056.0-57.01.55701.54821.56781.534052.0-54.01.549558.0-60.01.543762.0-63.051.0-52.043.0-44.553.0-54.555.0-57.043.0-47.037.0-40.052.0-55.066.0-67.556.0-58.061.0-62.547.0-49.062.0-65.061.0-63.054.0-56.0 |
表3
化合物编号 | R1 | Xn | Y | 熔点(℃)或折射率(nD 20) |
535455565758596061626364656667686970717273747576777879 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3C2H5CH(CH3)2CH(CH3)2CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | 2,6-Cl22-Cl2-Cl,6-F2,6-F22,6-Cl22-Cl2-Cl,6-F2,6-F22-Cl2-Cl,6-F2,6-F22-Cl,6-F2-Cl2-Cl,6-F2-Cl2-Cl,6-F2,6-F22-Cl2-Cl,6-F2-Cl2-Cl,6-F2-Cl2-Cl,6-F2,6-F22-Cl2-Cl2-Cl,6-F | 4-C15H314-C16H334-C16H334-C16H334-C16H334-C17H354-C17H354-C17H354-C18H374-C18H374-C18H374-C12H254-C12H254-C12H254-CH2CH2CH2CH2CH(CH3)24-CH2CH2CH2CH2CH(CH3)24-CH2CH2CH2CH2CH(CH3)24-CH2CH2CH2CH(C2H5)CH34-CH2CH2CH2CH(C2H5)CH34-CH2CH2CH(CH3)CH2CH2CH34-CH2CH2CH(CH3)CH2CH2CH34-CH2CH2CH2C(CH3)34-CH2CH2CH2C(CH3)34-CH2CH2CH2C(CH3)34-OC8H174-O(CH2)4CH(CH3)24-O(CH2)4CH(CH3)2 | 61.5-64.070.0-73.065.0-67.055.0-57.069.5-71.043.0-45.063.0-66.064.0-67.01.56141.55781.59351.57591.58791.569358.0-59.5 |
表6
表8
化合物编号 | R1 | Xn | 取代基位置 | A | R2m | 熔点(℃)或折射率(nD 20) |
165166167168169170171172173174175176177178179180181182183184185186187 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | 2-Cl2,6-F22-Cl2-Cl,6-F2-Cl2-Cl,6-F2,6-F22,6-Cl22-Cl2-Cl2-Cl2-Cl2-Cl,6-F2-Cl2-Cl,6-F2-Cl2-Cl,6-F2-Cl2-Cl,6-F2-Cl2-Cl,6-F2-Cl2-Cl,6-F | 4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4- | -----------CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2OCH2OOCH2OCH2 | H4-C3H74-C3H74-C3H74-C6H134-C6H134-C6H134-C6H134-Cl4-OCH33-CH3HH4-Cl4-Cl4-C4H94-C4H9HHHHHH | 152.0-154.5112.0-116.0111.5-114.0158.0-160.5112.0-114.093.0-95.096.0-98.096.0-97.5137.0-141.0137.0-139.068.0-71.01.624868.0-69.0160.0-162.099.0-102.0103.0-106.083.0-87.0143.0-153.0 |
表9
化合物编号 | R1 | Xn | 取代基位置 | A | R2m | 熔点(℃)或折射率(nD 20) |
188189190191192193194195196197198199200201202203204205206207208209210211212213214215 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | 2-Cl2-Cl,6-F2-Cl2-Cl2-Cl,6-F2,6-F22-Cl2-Cl,6-F2-Cl2-Cl,6-F2-Cl2-Cl,6-F2-Cl2-Cl,6-F2-Cl2-Cl,6-F2-Cl2-Cl,6-F2-Cl2-Cl,6-F2-Cl2-Cl,6-F2-Cl2-Cl,6-F2-Cl2-Cl,6-F2-Cl2-Cl,6-F | 4-4-3-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4- | CH2OCH2CH2OCH2OOOOOOOOOOOO----------CH2OCH2OCH2OCH2O | HHHHHH4-CH34-CH34-C4H94-C4H92-Cl2-Cl2-Cl,4-CF32-Cl,4-CF34-CH34-CH34-OCF34-OCF34-CF34-CF33,4-Cl23,4-Cl22,4-Cl22,4-Cl24-CH34-CH34-C4H94-C4H9 | 87.0-92.093.0-98.01.6354106.0-108.0165.0-168.085.0-89.0未能测量未能测量1.63881.6251151.0-154.0207.0-211.0119.0-122.0114.0-116.0155.0-159.0146.0-149.0135.0-138.0149.0-152.0 |
表10
化合物编号 | R1 | Xn | 取代基位置 | A | R2m | 熔点(℃)或折射率(nD 20) |
216217218219220221222223224225226227228229230231232233234235 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | 2-Cl2-Cl,6-F2-Cl2-Cl,6-F2-Cl2-Cl,6-F2-Cl2-Cl,6-F2-Cl2-Cl,6-F2-Cl,6-F2-Cl2-Cl,6-F2-Cl,6-F2-Cl,6-F2-Cl2-Cl,6-F2-Cl2-Cl,6-F2-Cl,6-F | 4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4- | OCH2OCH2OCH2OCH2OOOOOO-----CH2CH2CH2CH2OOO | 4-CH34-CH32,3,4,5,6-F52,3,4,5,6-F54-C6H134-C6H133,4-Cl23,4-Cl22,4-Cl22,4-Cl24-OCH34-OC4H94-OC4H93-CH34-Cl4-CH34-CH33,5-Cl23,5-Cl24-Cl | 108.0-110.0150.0-155.01.60601.5891115.0-118.0103.0-106.0未能测量未能测量191.0-192.0118.0-121.0141.0-144.0131.0-134.0105.0-107.095.0-97.0188.0-192.0105.0-108.0121.0-123.0未能测量 |
表11
化合物编号 | R1 | Xn | 取代基位置 | A | R2m | 熔点(℃)或折射率(nD 20) |
236237238239240241242243244245246247248249250251252253254255256257258259260261262263264 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | 2-Cl2-Cl,6-F2,6-F22-Cl,6-F2-Cl,6-F2-Cl,6-F2-Cl,6-F2,6-F22-Cl,6-F2-Cl,6-F2-Cl,6-F2-Cl,6-F2-Cl2,6-F22-Cl2,6-F22-Cl,6-F2,6-F22,6-F22-Cl2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F2 | 3-3-3-3-3-3-3-4-4-4-4-4-3-3-3-3-3-3-3-4-4-4-4-3-3-4-4-3-3- | ---O-OO-OCH2OOOOOSSSOSOOO-CH2CH2CH2CH2CH2CH2CH2CH2 | 4-CF34-CF34-CF34-CF34-OCF34-OCF32-Cl,4-CF34-CF34-CF34-CF34-OCF33,4-F24-CF34-CF34-CF34-CF34-CF34-OCF34-OCF34-CF34-CF34-CF34-OCF34-CF34-CF34-CF34-CF34-CF34-CF3 | 未能测量未能测量114.0-117.0101.0-102.095.0-99.0 |
表12
化合物编号 | R1 | Xn | 取代基位置 | A | R2m | 熔点(℃)或折射率(nD 20) |
265266267268269270271272273274275276277278279280281282283284285286287288289290291292293 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | 2-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F | 4-4-3-3-4-4-3-3-4-4-3-3-4-4-3-3-4-4-3-3-3-3-4-4-3-3-4-4-3- | CH2CH2CH2CH2CH2CH2CH2CH2CH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OOCH2OCH2OCH2OCH2OOCH2OCH2OCH2OCH2OOOOOCH2O | 4-CF34-CF34-OCF34-OCF34-OCF34-OCF34-CF34-CF34-CF34-CF34-OCF34-OCF34-OCF34-OCF34-CF34-CF34-CF34-CF32-Cl,4-CF32-Cl,4-CF32-Cl,4-CF32-Cl,4-CF32-Cl,4-CF32-Cl,4-CF32,6-Cl2,4-CF32,6-Cl2,4-CF32,6-Cl2,4-CF32,6-Cl2,4-CF32,6-Cl2,4-CF3 |
表13
化合物编号 | R1 | Xn | 取代基位置 | A | R2m | 熔点(℃)或折射率(nD 20) |
294295296297298299300301302303304305306307308309310311312313314315316317318319320321322 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | 2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2, 6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F2 | 3-4-4-3-3-4-4-3-3-4-4-3-3-4-4-3-3-4-4-4-4-4-4-4-4-4-4-4-4- | CH2OCH2OCH2OOOOOOOOOOOOOOOOOCH2OCH2OOOCH2OCH2OOOCH2OCH2O | 2,6-Cl2,4-CF32,6-Cl2,4-CF32,6-Cl2,4-CF33,5-(CF3)23,5-(CF3)23,5-(CF3)23,5-(CF3)24-Cl,3-CF34-Cl,3-CF34-Cl,3-CF34-Cl,3-CF33-F,5-CF33-F,5-CF33-F,5-CF33-F,5-CF34-Br4-Br4-Br4-Br4-Br4-Br2,4,6-Br32,4,6-Br32,4,6-Br32,4,6-Br32,4-Br22,4-Br22,4-Br22,4-Br2 |
表14
化合物编号 | R1 | Xn | 取代基位置 | A | R2m | 熔点(℃)或折射率(nD 20) |
323324325326327328329330331332333334335336337338339340341342343344345346347348349350351 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | 2-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F | 4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4- | OOCH2OCH2OOOCH2OCH2OOOCH2OCH2OOOCH2OCH2OOOCH2OCH2OOOCH2OCH2OCH2OCH2OCH2OCH2OO | 4-Br,3,5-(CH3)24-Br,3,5-(CH3)24-Br,3,5-(CH3)24-Br,3,5-(CH3)24-Br,3-CH34-Br,3-CH34-Br,3-CH34-Br,3-CH33-Cl,4-F3-Cl,4-F3-Cl,4-F3-Cl,4-F2,6-Cl2,5-CF32,6-Cl2,5-CF32,6-Cl2,5-CF32,6-Cl2,5-CF33,4,5-F33,4,5-F33,4,5-F33,4,5-F34-F,2-CF34-F,2-CF34-F,2-CF34-F,2-CF33,4-Cl23,4-Cl22,4-Cl22,4-Cl22,4,5-Cl3 |
表15
化合物编号 | R1 | Xn | 取代基位置 | A | R2m | 熔点(℃)或折射率(nD 20) |
352353354355356357358359360361362363364365366367368369370371372373374375376377378379380 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | 2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl, 6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F2 | 4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4- | OCH2OCH2OOOCH2OCH2OOOCH2OCH2OOOCH2OCH2OOOCH2OCH2OOOCH2OCH2OOOCH2OCH2OOCH2OCH2 | 2,4,5-Cl32,4,5-Cl32,4,5-Cl32,4,6-Cl32,4,6-Cl32,4,6-Cl32,4, 6-Cl34-Cl,3-CH34-Cl,3-CH34-Cl,3-CH34-Cl,3-CH34-Cl,3,5-(CH3)24-Cl,3,5-(CH3)24-Cl,3,5-(CH3)24-Cl,3,5-(CH3)24-Cl,3-C2H54-Cl,3-C2H54-Cl,3-C2H54-Cl,3-C2H54-Cl,3-F4-Cl,3-F4-Cl,3-F4-Cl,3-F4-Cl,2-F4-Cl,2-F4-Cl,2-F4-Cl,2-F4-Cl4-Cl |
表16
化合物编号 | R1 | Xn | 取代基位置 | A | R2m | 熔点(℃)或折射率(nD 20) |
381382383384385386387388389390391392393394395396397398399400401402403404405406407408409 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | 2-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22,6-F22-Cl,6-F2,6-F2 | 4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-3-4-4- | OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2--- | 3,4-Cl23,4-Cl22,4-Cl22,4-Cl24-F4-F3,4-F23,4-F22,4-F22,4-F24-Br4-Br4-F,3-CF34-F,3-CF34-OCF34-OCF33-OCF33-OCF33,4,5-F33,4,5-F32,4-(CF3)22,4-(CF3)22-F,4-CF32-F,4-CF34-F,2-CF34-F,2-CF34-OCF34-Cl,2-CH34-Cl,2-CH3 |
表17
化合物编号 | R1 | Xn | 取代基位置 | A | R2m | 熔点(℃)或折射率(nD 20) |
410411412413414415416417418419420421422423 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | 2-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F2 | 4-4-4-4-4-4-4-4-4-4-4-4-4-4- | -------------- | 3,5-Cl23,5-Cl23-Cl,4-F3-Cl,4-F2-Cl,4-CF32-Cl,4-CF32,4,6-Cl32,4,6-Cl32,4-F22,4-F23,4-F23,4-F22,4-(CF3)22,4-(CF3)2 |
表18
化合物编号 | R1 | Xn | 取代基位置 | A | R2m | 熔点(℃)或折射率(nD 20) |
424425426427428429430431432433434435436437438439440441442443444445446447 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | 2-Cl2,6-F22-Cl2-Cl,6-F2-Cl2-Cl,6-F2-Cl2-Cl2-Cl,6-F2-Cl,6-F2-Cl,6-F2-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2-Cl,6-F2-Cl,6-F2-Cl,6-F2-Cl,6-F2-Cl2-Cl,6-F2,6-F22-Cl,6-F | 4-4-4-4-4-4-4-4-4-2-3-3-3-3-3-3-3-3-3-3-3-3-3-3- | OOOOOOSCH2OCH2OOOOOOOOOOOOOOOO | HH5-CF35-CF33-Cl,5-CF33-Cl,5-CF33-Cl,5-CF3HH5-CF3H5-Cl5-Cl6-Cl6-Cl4-CH35-CH36-CH34-C2H56-C3H73-CF33-CF33-CF34-CF3 | 122.0-127.0107.0-109.094.0-96.0未能测量未能测量127.0-131.0126.0-129.0未能测量未能测量124.0-127.0未能测量未能测量未能测量122.0-124.01.5820 |
表19
化合物编号 | R1 | Xn | 取代基位置 | A | R2m | 熔点(℃)或折射率(nD 20) |
448449450451452453454455456457458459460461462463464465466467468469470471472473474475476 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | 2,6-F22-Cl,6-F2-Cl2-Cl,6-F2,6-F22,6-Cl22-Cl,6-F2-Cl,6-F2-Cl2-Cl,6-F2,6-F22,6-Cl22-Cl,6-F2-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl2-Cl,6-F2,6-F22-Cl2-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F2 | 3-3-3-3-3-3-3-3-3-3-3-3-3-3-3-3-3-3-3-3-3-3-3-3-3-3-3-3-3- | OOOOOOSCH2CH2OCH2OCH2OCH2OC2H4OOOOOOOOOOOOOOOOO | 4-CF35-CF35-CF35-CF35-CF35-CF35-CF35-CF35-CF35-CF35-CF35-CF35-CF36-CF36-CF35-Cl,3-CF35-Cl,3-CF35-Cl,3-CF35-Cl,3-CF35-Cl,3-CF33-Cl,5-CF33-Cl,5-CF33-Cl,5-CF33,5-(CF3)23,5-(CF3)26-Cl,5-CF36-Cl,5-CF34,5-(CF3)24,5-(CF3)2 | 未能测量65.0-68.0未能测量82.0-86.098.0-102.071.0-73.0109.0-111.0未能测量未能测量91.0-95.0未能测量122.0-126.0 |
表20
化合物编号 | R1 | Xn | 取代基位置 | A | R2m | 熔点(℃)或折射率(nD 20) |
477478479480481482483484485486487488489490491492493494495496497498499500501502503504505 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3C2H5CH(CH3)2CH3CH3C6H13CH3CH3CH3 | 2-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2-Cl,6-F2-Cl,6-F2-Cl,6-F2-Cl,6-F2-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2-Cl,6-F2,6-F22,6-Cl22-Cl,6-F2-Cl2-Cl,6-F2,6-F2 | 3-3-3-3-3-3-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4- | OOOOOOOOOOOOOOOOOOO--OOOOOSSS | 6-Cl,4-CF36-Cl,4-CF34,6-(CF3)24,6-(CF3)26-CH3,4-CF36-CH3,4-CF35-Cl5-Cl6-Cl6-Cl4-CH34-C2H55-CH36-CH36-C3H73-CF33-CF34-CF34-CF35-CF35-CF35-CF35-CF35-CF35-CF35-CF35-CF35-CF35-CF3 | 未能测量1.5453121.0-123.0136.0-139.0134.0-136.0136.0-140.0154.0-157.0未能测量158.0-159.9110.0-114.0未能测量未能测量127.0-131.0127.0-130.01.5573未能测量111.0-115.0 |
表21
化合物编号 | R1 | Xn | 取代基位置 | A | R2m | 熔点(℃)或折射率(nD 20) |
506507508509510511512513514515516517518519520521522523524525526527528529530531532533 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | 2,6-Cl22-Cl,6-F2,6-F22-Cl2-Cl,6-F2,6-F22,6-Cl22-Cl,6-F2-Cl,6-F2-Cl,6-F2-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F2 | 4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4- | SCH2CH2CH2OCH2OCH2OCH2OC2H4OOOOOSSCH2OCH2OOOOOOOOOOOOO | 5-CF35-CF35-CF35-CF35-CF35-CF35-CF35-CF36-CF33,5-Cl25-Cl,3-CF35-Cl,3-CF33-Cl,5-CF33-Cl,5-CF33-Cl,5-CF33-Cl,5-CF33,5-(CF3)23,5-(CF3)26-Cl,5-CF36-Cl,5-CF34,5-(CF3)24,5-(CF3)26-Cl,4-CF36-Cl,4-CF34,6-(CF3)24,6-(CF3)26-CH3,4-CF36-CH3,4-CF3 | 1.585997.0-101.0未能测量未能测量1.577885.0-89.0108.0-112.0158.0-160.0未能测量125.0-129.098.0-101.0 |
表22
化合物编号 | R1 | Xn | 取代基位置 | A | R2m | 熔点(℃)或折射率(nD 20) |
534535536537538539540541542543544545546547548549550551552553554555556557558559560561562 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | 2,6-F22,6-F22,6-F22,6-Cl22-Cl2-Cl,6-F2,6-F22,6-Cl22-Cl2-Cl,6-F2,6-F22,6-Cl22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F | 3-3-3-3-3-3-3-3-3-3-3-3-3-3-3-3-3-3-3-3-3-3-3-3-3-3-3-3-3- | -SCH2OSSSSCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2O | 5-CF35-CF35-CF33-Cl,5-CF33-Cl,5-CF33-Cl,5-CF33-Cl,5-CF33-Cl,5-CF33-Cl,5-CF33-Cl,5-CF33-Cl,5-CF33-Cl,5-CF33,5-(CF3)23,5-(CF3)24,5-(CF3)24,5-(CF3)24,6-(CF3)24,6-(CF3)26-CH3,4-CF36-CH3,4-CF35-Cl5-Cl5-CH35-CH33,5-Cl23,5-Cl25-Cl,3-CF35-Cl,3-CF36-Cl,5-CF3 |
表23
化合物编号 | R1 | Xn | 取代基位置 | A | R2m | 熔点(℃)或折射率(nD 20) |
563564565566567568569570571572573574575576577578579580581582583584585586587588589590591 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | 2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl2-Cl,6-F2,6-F22,6-Cl22-Cl2-Cl,6-F2,6-F22,6-Cl2 | 3-3-3-3-3-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4- | CH2OCH2OCH2OOOCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2O | 6-Cl,5-CF36-Cl,4-CF36-Cl,4-CF33,5-Cl23,5-Cl25-Cl5-Cl6-Cl6-Cl4-CH34-CH35-CH35-CH36-CH36-CH33-CF33-CF34-CF34-CF36-CF36-CF33,5-Cl23,5-Cl23,5-Cl23,5-Cl25-Cl,3-CF35-Cl,3-CF35-Cl,3-CF35-Cl,3-CF3 |
表24
化合物编号 | R1 | Xn | 取代基位置 | A | R2m | 熔点(℃ )或折射率(nD 20) |
592593594595596597598599600601602603604605606607608609610611612613614615616617618619620 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | 2-Cl2,6-Cl22-Cl2-Cl,6-F2,6-F22,6-Cl22-Cl2-Cl,6-F2,6-F22,6-Cl22-Cl2-Cl,6-F2,6-F22,6-Cl22-Cl2-Cl,6-F2,6-F22,6-Cl22-Cl2-Cl,6-F2,6-F22,6-Cl22-Cl2-Cl,6-F2,6-F22,6-Cl22-Cl,6-F2,6-F22-Cl,6-F | 4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4- | CH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2OCH2CH2OCH2CH2OCH2CH2O | 3-Cl,5-CF33-Cl,5-CF33,5-(CF3)23,5-(CF3)23,5-(CF3)23,5-(CF3)26-Cl,5-CF36-Cl,5-CF36-Cl,5-CF36-Cl,5-CF34,5-(CF3)24,5-(CF3)24,5-(CF3)24,5-(CF3)26-Cl,4-CF36-Cl,4-CF36-Cl,4-CF36-Cl,4-CF34,6-(CF3)24,6-(CF3)24,6-(CF3)24,6-(CF3)26-CH3,4-CF36-CH3,4-CF36-CH3,4-CF36-CH3,4-CF33-Cl,5-CF33-Cl,5-CF33,5-(CF3)2 |
表25
化合物编号 | R1 | Xn | 取代基位置 | A | R2m | 熔点(℃)或折射率(nD 20) |
621622623624625626627628629630631632633634635636637638639640641642643644645646647 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | 2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F22-Cl,6-F2,6-F2 | 4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4-4- | CH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OSSSSSSSSSSSS | 3,5-(CF3)26-Cl,5-CF36-Cl,5-CF35-Cl,3-CF35-Cl,3-CF34,5-(CF3)24,5-(CF3)26-Cl,4-CF36-Cl,4-CF34,6-(CF3)24,6-(CF3)26-CH3,4-CF36-CH3,4-CF33,5-Cl23,5-Cl23,5-Cl23,5-Cl25-Cl,3-CF35-Cl,3-CF33,5-(CF3)23,5-(CF3)26-Cl,5-CF36-Cl,5-CF34,5-(CF3)24,5-(CF3)24,6-(CF3)24,6-(CF3)2 |
本发明的化合物可用下面的方法来生产。但是,並不想将本发明限制于这些方法。
生产方法A
按照本发明,具有通式〔I〕的化合物可以通过下面的反应式(I),在一种惰性溶剂中,把具有通式〔II〕的N-酰基(硫代)亚胺羧酸酯衍生物与具有通式〔III〕的肼衍生物进行反应而制得:(其中W是硫原子或氧原子,L是含有1-4个碳原子数的烷基,R1,x,n和y的意义与上面叙述的相同)。
作为溶剂,任何一种不妨碍反应进行的溶剂都可以使用,它包括,例如一种醇类诸如甲醇、乙醇或类似物;一种醚类诸如二乙醚,四氢呋喃,二噁烷,乙二醇二甲醚或类似物;一种芳香烃类诸如苯、甲苯、氯苯或类似物;一种脂肪烃类诸如戊烷、己烷、石油醚或类似物;一种卤代烃诸如二氯甲烷、二氯乙烷、氯仿、四氯化碳或类似物;一种腈类诸如乙腈或类似物;一种非质子极性溶剂诸如N,N-二甲基甲酰胺,N,N-二甲基乙酰胺,二甲基亚砜或类似物;水以及它们的混合物。
一般,具有通式〔III〕的化合物的用量是相对每1摩尔具有通式〔II〕的化合物用1.0-5.0摩尔。
反应温度可任意选择在0℃至溶剂沸点之间的范围内,但最好是在0℃-50℃之间。反应时间依赖于所用化合物的种类,但通常是在1~72小时之间。
这一反应的一个具体实例已公开发表在,例如,Synthesis,第483页(1983年)。
作为原料的具有通式〔II〕的化合物可用下面的方法来生产。
生产方法B
具有通式〔II〕的化合物可按照下面的反应式(2),在一种惰性溶剂中,在一种碱存在的条件下,把具有通式〔IV〕和〔V〕的化合物进行反应而制得:(其中具有通式〔IV〕的衍生物可以是一种与酸加成的盐(例如与四氟化硼、氯化氢、溴化氢、碘化氢或类似物形成的盐),Z是卤原子,L,W,x,n和y的意义与上面叙述的相同)。
作为碱,可使用一种无机碱诸如碳酸钠、碳酸钾、碳酸氢钠、氢氧化钠、氢氧化钾或类似物;和一种有机碱诸如二乙胺,三乙胺,二异丙基乙胺,吡啶,4-N,N-二甲胺基吡啶或类似物。
作为溶剂,可使用一种酮诸如丙酮,甲乙酮或类似物;一种醚诸如二乙醚、四氢呋喃、二噁烷、乙二醇二甲醚或类似物;一种芳香烃诸如苯、甲苯、氯苯或类似物;一种脂肪烃诸如戊烷、己烷、石油醚或类似物;一种卤代烃诸如二氯甲烷、二氯乙烷、氯仿、四氯化碳或类似物;一种腈类诸如乙腈或类似物;一种非质子极性溶剂诸如N,N-二甲基甲酰胺、N,N-二甲基乙酰胺,二甲基亚砜或类似物以及上述溶剂的混合物。
一般,具有通式〔V〕的化合物的用量是相对于1摩尔具有通式〔IV〕的化合物用0.8-1.3摩尔。碱的用量是相对于每1摩尔具有通式〔IV〕的化合物用1.0-2.0摩尔。
反应时间依赖于所用化合物的种类,但一般是在1-24小时范围内。反应温度在0℃至溶剂沸点之间的范围内。
生产方法C
按照本发明,具有通式〔I〕的化合物可按照下面的反应式(3),在一种惰性溶剂中,在一种Lewis酸存在的条件下,把具有通式〔VI〕的N-(苯磺酰基)苯甲腙酰基氯化物衍生物与一种具有通式〔VIII〕的苯腈衍生物进行反应而制得:(其中R1,x,n和y的意义与上面叙述的相同,R3是苯或被一个含有1-4个碳原子数的烷基所取代的苯)。
作为溶剂,可使用任意一种不妨碍反应进行的溶剂,它包括,例如一种醚诸如二乙醚、四氢呋喃、二噁烷、乙二醇二甲醚或类似物;一种芳香烃诸如苯、甲苯、氯苯、二氯苯或类似物;一种脂肪烃诸如戊烷、己烷、石油醚或类似物;一种卤代烃诸如二氯甲烷、二氯乙烷、氯仿、四氯化碳或类似物;一种非质子极性溶剂诸如硝苯、N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、二甲基亚砜或类似物;以及上述溶剂的混合物。
作为Lewis酸,可使用溴化铝、氯化铝、氯化铁、三氟化硼、四氯化钖以及类似物。
一般,具有通式〔VII〕的化合物的用量是相对于每1摩尔具有通式〔VI〕的化合物用1.0-2.0摩尔;Lewis酸的用量是相对于每1摩尔具有通式〔VI〕的化合物用1.0-2.0摩尔。
反应温度可任意地在0℃至溶剂沸点之间的范围内,但最好是在50-180℃的范围内;反应时间依赖于所用化合物的种类,但通常是在15分钟至8小时的范围内。
这一反应的一个具体实例已公开发表于,例如,Bulletinof the Chemical society of Japan,Vol,56,第545-548页(1983年)。
生产方法D
按照本发明,具有通式〔I〕的化合物可按照下面的反应式(4),在不存在溶剂或在一种惰性溶剂中,把具有通式〔VIII〕的N-(苯磺酰基)苯甲脒腙衍生物与一种具有通式〔V〕的苯甲酰卤衍生物进行反应而制得:(其中R1,R3,X,n,Y和Z的意义与上面叙述的相同)。
作为溶剂,可使用任何一种不妨碍反应进行的溶剂,它包括,例如,一种醚类诸如二乙醚、四氢呋喃、二噁烷、乙二醇二甲醚或类似物;一种芳香烃诸如苯、甲苯、氯苯或类似物;一种脂肪烃诸如戊烷、己烷、石油醚或类似物;一种卤代烃诸如二氯甲烷、二氯乙烷、氯仿、四氯化碳或类似物;一种非质子极性溶剂诸如N,N-二甲基甲酰胺,N,N-二甲基乙酰胺,二甲基亚砜,1-甲基-2-吡咯烷酮或类似物;以及上述溶剂的混合物。
一般,具有通式〔V〕的化合物的用量是相对于每1摩尔具有通式〔VIII〕的化合物用1.0-2.0摩尔。
反应温度可任意地在0℃至溶剂沸点之间的范围内,但最好是在50~250℃的范围内。反应时间依赖于所用化合物的种类,但通常是在30分钟至5小时之间的范围内。
这个反应的一个具体实例已公开发表在,例如,Bulletinof the Chemieal Society of Japan,Vol.56,第548页(1983年)。
作为原料的具有通式〔VIII〕的化合物可用下面的方法来生产。
生产方法E
作为溶剂,可使用任何一种不妨碍反应进行的溶剂,它包括,例如,一种醚类诸如二乙醚,四氢呋喃,二噁烷,乙二醇二甲醚或类似物;一种芳香烃诸如苯、甲苯、氯苯或类似物;一种脂肪烃诸如戊烷、己烷、石油醚或类似物;一种卤代烃诸如二氯甲烷,二氯乙烷,氯仿,四氯化碳,二氯苯或类似物;一种非质子极性溶剂诸如N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、二甲基亚砜或类似物;以及上述这些溶剂的混合物。
一般,氨气的用量是相对于每1摩尔具有通式〔VI〕的化合物用5.0-10.0摩尔。
反应温度可任意地在0℃至溶剂沸点之间的范围内,但最好是在20℃-150℃之间的范围内。反应时间依赖于所用化合物的种类,但一般是在1-24小时的范围内。
这个反应的一个具体实例已公开发表在,例如,Bulletinof the Chemieal Society of Japan,Vol.56,第545-548页(1983年)。
本发明将通过参照下面的生产实例、配方实例以及应用来具体地描述。
生产实例1:3-(2-氯-6-氟苯基)-1-甲基-5-(4-辛基苯基)-1H-1,2,4-三唑(化合物№.15)
在100毫升甲苯中溶解2.20克2-氯-6-氟-苯甲亚胺羧酸乙酯和1.10克三乙胺,在搅拌和5~10℃的温度范围内往其中滴加2.53克4-辛基苯甲酰氯,然后在室温搅拌1小时并进一步回流加热2小时。冷却至室温后,往得到的反应溶液中加入100毫升甲苯,用稀盐酸洗涤,再用食盐溶液洗涤,然后把得到的甲苯层用无水硫酸镁干燥。
往甲苯层中加入3.00克-甲基肼並在室温搅拌8小时,反应完全后把反应混合物用稀盐酸溶液洗涤並进一步用食盐水溶液洗涤,用无水硫酸镁干燥並减压浓缩,得到的浓缩物通过硅胶柱层析提纯,用己烷和乙酸乙酯的混合溶液作为展开溶剂,即得到1.34克给出的化合物(nD 20=1.5652)。
NMR数据(60MHz,CDCl3溶剂,δ值)
0.77 (3H,t)
1.00-1.79 (12H,m)
2.57 (2H,t)
3.95 (3H,s)
6.83-7.67 (7H,m)
生产实例2:3-(2-氯苯基)-1-甲基-5-〔4-(6-甲基己基)苯基〕-1H-1,2,4-三唑(化合物№.67)
把2.06克N-甲基-N-苯磺酰基-2-氯-苯甲腙酰氯,1.30克4-(6-甲基己基)苯腈,0.93克无水氯化铝和5毫升邻-二氯苯所形成的混合物在温度为140℃的油浴中搅拌加热30分钟,冷却后把得到的溶液溶解在200毫升氯仿中,按顺序用稀盐酸溶液,稀氢氧化钠溶液和食盐水溶液相继洗涤,用无水硫酸镁干燥並减压浓缩。得到的浓缩物通过硅胶柱层析提纯,用己烷和乙酸乙酯的混合溶液作为展开溶剂,即得到1.52克给出的化合物(熔点:64.0-67.0℃)。
NMR数据(60MHz,CDCl3溶剂,δ值)
0.86 (6H,d)
1.15-1.80 (7H,m)
2.67 (2H,t)
4.00 (3H,s)
7.17-8.00 (8H,m)
生产实例3. 3-(2-氯苯基)-1-甲基-5-(4-十三碳烷基苯基)1H-1,2,4-三唑(化合物№.42)
把0.82克N-甲基-N-苯磺酰基-2-氯苯甲腙酰氯、0.70克4-十三碳烷基苯腈,0.4克无水氯化铝和3毫升邻二氯苯所形成的混合物在温度为140℃的油浴中搅拌加热30分钟。冷却后,把得到的溶液溶解于100毫升氯仿中,按顺序用稀盐酸溶液、稀氢氧化钠溶液和食盐水溶液相继洗涤,用无水硫酸镁干燥並减压浓缩,得到的浓缩物通过硅胶柱层析提纯,用己烷和乙酸乙酯的混合溶液作为展开溶剂,即得到0.70克给出的化合物(熔点·55.0~57.0℃)。
NMR数据(60MHz,CDCl3溶剂,δ值)
0.67-1.80 (25H,m)
2.67 (2H,t)
4.00 (3H,s)
7.16-8.03 (8H,m)
生产实例4:3-(2-氯苯基)-1-甲基-5-(4-十五碳烷基苯基)-1H-1,2,4-三唑(化合物№.50)
把3.4克N-甲基-N-苯磺酰基-2-氯苯甲脒腙和3.50克4-十五碳烷基苯甲酰氯所组成的混合物在温度为170-180℃的油浴中搅拌加热4小时。冷却后,把得到的溶液加水並用乙酸乙酯提取(200毫升×2),提取的有机层用食盐水溶液洗涤,用无水硫酸镁干燥并减压浓缩,得到的浓缩物通过硅胶柱层析提纯,用己烷和乙酸乙酯的混合溶液作为展开溶剂,即得到0.34克给出的化合物(熔点:62.0-65.0℃)。
NMR数据(60MHz,CDCl3溶剂,δ值):
0.77-1.73 (29H,m)
1.67 (2H,m)
4.00 (3H,s)
7.17-7.97 (8H,m)
生产实例5:5-(4-癸氧基苯基)-3-(2,6-二氯苯基)-1-甲基-1H-1,2,4-三唑(化合物№.85)
把1.10克N-甲基-N-苯磺酰基-2,6-二氯苯甲腙酰氯,0.70克4-癸氧基苯腈,0.4克无水氯化铝和3毫升邻-二氯苯在温度为140℃的油浴中搅拌加热30分钟。冷却后,把得到的溶液溶解于100毫升氯仿中,按顺序用稀盐酸溶液、稀氢氧化钠溶液和食盐水溶液相继洗涤,用无水硫酸镁干燥並减压浓缩,得到的浓缩物通过硅胶柱层析提纯,用己烷和乙酸乙酯的混合溶液作为展开溶剂,即得到0.40克给出的化合物(熔点:60.0-64.0℃)。
NMR数据(60MHz,CDCl3溶剂,δ值)
0.77-1.90 (19H,m)
3.98 (2H,t)
4.04 (3H,s)
6.88-7.73 (7H,m)
生产实例6:3-(2-氯-6-氟苯基)-5-〔4-(3-氯-5-三氟甲基吡啶-2-基氧基)苯基〕-1-甲基-1H-1,2 4-三唑(化合物№.429)
把1.30克N-甲基-N-苯磺酰基-2-氯-6-氟苯甲腙酰氯、1.00克4-(3-氯-5-三氟甲基吡啶-2-基氧基)苯腈,0.50克无水氯化铝和3毫升邻二氯苯所组成的混合物在温度为140℃的油浴中搅拌加热30分钟。冷却后,把得到的溶液溶解于100毫升氯仿,按顺序用稀盐酸溶液、稀氢氧化钠溶液和食盐水溶液相继洗涤,用无水硫酸镁干燥並减压浓缩。得到的浓缩物通过硅胶柱层析提纯,用己烷和乙酸乙酯的混合溶液作为展开溶剂,即得到0.70克给出的化合物(nD 20值的测量是不可能的)。
NMR数据(60MHz,CDCl3溶剂,δ值)
4.07 (3H,s)
6.75-8.58 (9H,m)
生产实例7:N-甲基-N-苯磺酰基-2-氯-苯甲脒腙
在100毫升N,N-二甲基甲酰胺中溶解17.2克N-甲基-N-苯磺酰基-2-氯-苯甲腙酰氯,把它在60-70℃搅拌加热3小时,同时往其中引入氨气,冷却后,把反应溶液溶解于500毫升乙酸乙酯中,用水洗,用无水硫酸镁干燥並减压浓缩,得到的结晶用正己烷洗涤后即得15.4克给出的化合物(熔点:94.0-96.0℃)。
NMR数据(60MHz,CDCl3溶剂,δ值)
2.75 (3H,s)
5.80 (2H,s)
7.10-8.00 (9H,m)
按照本发明的杀虫剂和杀螨剂含有通式〔I〕代表的三唑衍生物作为活性组分。
当把按照本发明的三唑化合物用作杀虫剂和杀螨剂的活性组分时,这些化合物本身可被单独使用,也可以和载体、表面活性剂、分散剂、辅剂等通常用于配方中的物质一起使用,来形成粉尘剂、可湿性粉剂,乳液,细粉,颗粒剂等。
作为用于配方中的载体,可以提到固体的载体诸如沸石、滑石、膨润土、粘土、高岭土、硅藻土、白碳、蛭石、氢氧化钙、石英砂、硫酸铵、尿素或类似物;以及液体载体诸如异丙醇、二甲苯、环己烷、甲基萘或类似物。
作为表面活性剂和分散剂,可以提到的有烷基苯磺酸的金属盐,二萘甲烷二磺酸的金属盐,醇的硫酸酯,烷基芳基磺酸酯,木质素磺酸盐,聚氧乙烯乙二醇醚,聚氧乙烯烷基芳基醚,聚氧乙烯山梨糖醇酐-烷基化物以及类似物。
作为辅剂的可以提到羧甲基纤维素、聚乙二醇、阿拉伯胶以及类似物。
在应用时,本发明的化合物可以直接施药,也可稀释至适当的浓度后通过喷雾施药。
按照本发明的杀虫剂和杀螨剂可通过喷撒到茎和叶片上,施用到土壤中,施用到苗圃中,喷撒到水面上等这类方式来使用。
在配方中,活性组分的用量可按照使用的目的来选择,但对于粉剂和粒剂一般可适当地选择在0.05-20%,最好是在0.10-10%重量百分数的范围内。在乳液或可湿性粉末的情况下,活性组分的量可适当地选在0.5-80%重量百分数的范围内,最好是1-60%重量百分数的范围内。
杀虫剂和杀螨剂的施药量依赖于所用的作为活性组份的化合物的种类、被控制的有害昆虫种类、有害昆虫为害的趋势和程度、环境条件、所用配方的种类等条件。当本发明的杀虫剂和杀螨剂直接以粉剂或粒剂使用时,活性组份的用量适当地选在每10英亩0.05克-5公斤、最好是0.1-1公斤的范围内。进一步,当它们以液体形式作为乳液或可湿性粉末使用时,活性组份的用量应适当地选在0.1-5,000ppm,最好是1-1000ppm的范围内。
还有,本发明的杀虫剂和杀螨剂可以和其它杀虫剂、杀真菌剂、肥料、植物生长调节剂等混合使用。
配方将通过典型实例来具体地描述,在这种情况下,化合物和添加剂的种类和化合比将不限制于这些实例,而是可以在很宽的范围内变化。还有,除非特别指明,%是指重量百分数。
配方实例1,乳液
乳液可通过均匀地溶解30%№.55号化合物,20%环己酮,11%聚氧乙烯烷基芳基醚,4%烷基苯磺酸钙和35%甲基萘而制得。
配方实例2:可湿性粉末
可湿性粉末可通过均匀地混合並研碎40%的№.38号化合物,15%的硅藻土,15%的粘土,25%白碳,2%二萘甲烷二磺酸钠和3%木质素磺酸钠而制得。
配方实例3:粉尘剂
粉尘剂可通过均匀地混合並研碎2%的№.120号化合物、5%硅藻土和93%的粘土而制得。
配方实例4:粒剂
把5%的№.71号化合物,2%的月桂醇硫酸酯的钠盐,5%木质素磺酸钠,2%羧甲基纤维素和86%的粘土所形成的混合物均匀地研碎,通过捏合与20份一道加入一台挤压型造粒机中成形为14-32筛目的颗粒,並经干燥而形成粒剂。
按照本发明的三唑衍生物对于控制下列害虫是有效的:光蝉科诸如稻褐飞虱、白背飞虱、稻灰飞虱及类似物;叶蝉科诸如稻大白叶蝉、茶微叶蝉及类似物;蚜科诸如棉蚜、桃赤蚜、菜蚜及类似物;粉虱科诸如温室粉虱及类似物;半翅目有害昆虫诸如桑虱、稻蛛缘蝽及类似物;鳞翅目有害昆虫诸如小菜蛾、菜豆夜蛾、斜纹夜蛾及类似物;双翅目有害昆虫诸如家蝇的蛆、蚊子及类似物;鞘翅目有害昆虫诸如稻象甲,大豆象甲,黄守瓜及类似物;直翅目有害昆虫诸如美洲大蠊,Steamfly及类似物;螨诸如普通红叶螨,神泽叶螨,桔全爪螨及类似物;以及对于有机锡、合成的拟除虫菊类和有机磷化合物具有日益增加的耐药性的螨类。
特别是,它们对于控制螨类,诸如普通红叶螨、神泽叶螨、桔全爪螨及类似物具有很优良的效果。
本发明化合物的药效将通过下面的试验实例来描述。还有,下列化合物被用来作为比较用的化合物,其中一种供比较用的化合物a是日本专利公开号56-154464中所叙述的化合物,另一种供比较用的化合物b是通常用来控制螨类的商品。
比较用的化合物A:3,5-双(邻氯苯基)-1-甲基-1H-1,2,4-三唑
比较用的化合物B:Hexythiazox(通用商品名)
试验实例1:对小菜蛾的杀虫试验
把按照配方实例2制得的可湿性粉末用水稀释,使得活性组份的浓度为500ppm,把白菜叶片浸在得到的经稀释后的溶液中,在空气中干燥后放在容积为60毫升的氯乙烯杯子里,把十只第三龄期小菜蛾的幼虫释放在杯中,然后放上一只盖子,把杯子在恒温于25℃的小室中放置6天,计数死亡的幼虫数並计算死亡百分数,试验通过两套平行实验来进行。还有,比较化合物A被用作参照物,结果列于表26中。
表26
化合物编号 | 死亡率(%) |
1730374371120135140185207217240244427471 | 901009095959590951009010010010010095 |
化合物编号 | 死亡率(%) |
479483494500504510514520524526528530532 | 1001001001009510010010090100100100100 |
供比较用的化合物A | 20 |
试验实例2:对棉蚜幼虫的杀虫试验
把按照配方实例2制得的可湿性粉末用水稀释,使得活性组份的浓度为100ppm,往得到的稀溶液中浸渍事先移种了棉蚜幼虫的黄瓜秧苗,然后把它在空气中进行干燥处理。处理后,把黄瓜秧苗放在25℃的恒温室中3天,然后计数死去的幼虫数目並用来计算死亡百分数。试验通过两套平行实验来进行,结果列于表27中。
表27
化合物编 号 | 死亡率(%) |
371314151719303539475168697173818487899697100101103104105106107108 | 100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100 |
化合物编 号 | 死亡率(%) |
109111112113114117118119127131135140144146148149150151152153163190194195220223224225228 | 100100100100100100100100100100100100100100100100100100100100100100100100100100100100100 |
化合物编 号 | 死亡率(%) |
229234235239240247425427434435447450451452468469475490494503504510516518520522528530532 | 100100100100100100100100100100100100100100100100100100100100100100100100100100100100100 |
试验实例3:对普通红叶螨卵的杀卵试验
把普通红叶螨的雌性成虫放在菜豆的三叶片上(直径:15毫米),使之产卵24小时,然后拿走这些成虫,把按照配方实例2制得的可湿性粉末用水稀释,使其中活性组份的浓度为0.16ppm。把上述叶盘在得到的稀溶液中浸渍10秒钟,处理后,叶片被放置在25℃的恒温室中7天,然后计数未孵化的卵的数目,並用来计算杀卵活性的百分数。试验通过两套平行实验来进行。还有,比较化合物A和B被用来作为参照物,结果被列于表28中。
表28
化合物编号 | 杀卵活性(%) |
21303435383942434750515455 | 1001001001001009510095100100100100100 |
供比较用的化合物A供比较用的化合物B | 2495 |
试验实例4:对具有化学品耐药性的神泽叶螨卵的杀卵试验
把对市售化学品具有耐药性的神泽叶螨的雌性成虫放在菜豆的三叶片上(直径:15毫米)並使其产卵2天,然后除去这些成虫,把按照配方实例2制得的可湿性粉末用水稀释,使其中活性组份的浓度为4ppm。把上述叶片在得到的稀溶液中浸渍10秒钟。处理后,把叶片放在25℃的恒温室中7天,然后计数未孵化的虫卵数目並用来计算杀卵活性的百分数。试验通过两套平行实验来进行。还有,比较化合物A和B被用作参照物。结果列于表29和表30中。
表29
化合物编 号 | 杀卵活性(%) |
3613141530333435363738394041424344464748515253555657 | 10010010010010010010010010010010010010010010010010010090100100100959010010090 |
化合物编号 | 杀卵活性(%) |
8183848889106110111112117118140148151153166167168183191192193204205206217223 | 1001009010010010010095100100100100100100100100100100100100100100100100100100100 |
表30
化合物编 号 | 杀卵活性(%) |
225232235239240247425426427428429433434437444445447450451452454461465466468469471 | 100100100100100100100100100100100100100100100100100100100100100100100100100100100 |
化合物编号 | 杀卵活性(%) |
473475477479481483487489494498500501503504510514516518520522524526530532 | 100100100100100100100100100100100100100100100100100100100100100100100100 |
供比较用的化合物A供比较用的化合物B | 310 |
试验实例5:对化学品有耐药性的神泽叶螨幼虫的杀虫试验
把对市售化学品具有耐药性的神泽叶螨的雌性成虫放在菜豆的三叶片上(直径:15毫米)並使其产卵两天,然后除去这些成虫。把叶片放置在25℃的恒温室中5天並计数孵化出来的幼虫。另一方面,把按照配方实例2制得的可湿性粉末用水稀释,使其中活性组份的浓度为20ppm 。把叶片用得到的稀溶液喷雾之后,放置在25℃的恒温室中7天,然后计数还活着的成虫並用来计算孵化出来的幼虫的死亡百分数。试验通过两套平行实验来进行。还有,比较化合物A和B被用作参照物。结果被列于表31中。
表31
化合物编 号 | 死亡率(%) |
31314151617182130313234353637383940 | 100100100100100100100100100100100100100100100100100100 |
化合物编号 | 死亡率(%) |
414243444546474849505152535556 | 100100100100100100100100100100100100100100100 |
供比较用的化合物A供比较用的化合物B | 5525 |
试验实例6:对桔全爪螨卵的杀卵试验
把桔全爪螨的雌性成虫放在两薄片柑桔果上(直径10毫米)並使其产卵2天。然后除去这些成虫。按照配方实施2制得的可湿性粉末用水稀释,使其中活性组份的浓度为4ppm。把上述薄片在得到的稀溶液中浸渍10秒钟。处理后,薄片被放置在25℃的恒温室中7天,然后计数未孵化的虫卵数目並用来计算杀卵活性的百分数。试验通过两套平行实验来进行。还有,比较化合物A和B被用作参照物。实验结果被列在表32中。
表32
化合物编号 | 杀卵活性(%) |
31617182130313234353637383940434447485297106 | 95901001009510010010010010095100100100901001009510010095100 |
供比较用的化合物A供比较用的化合物B | 3390 |
Claims (8)
1.一种具有下列通式〔I〕的三唑衍生物:其中R1是一个C1-6烷基,X是一个卤原子或C1-6烷基,n值是1-5的整数,若当n值是2或更大时,X可以是相同或不同的原子或基团的任意组合;Y是一个C3-16烯基、C3-16炔基、C3-16烷硫基烷基、C6-12环烷基烷氧基、C6-12环烷基烷基、C5-12环烷基炔基,三C1-6烷基甲硅烷基C1-6烷氧基,C7-20烷基,C7-16烷氧基,C7-16烷硫基,或一个可被下列通式(1)表示的基团:其中A是一个氧原子,硫原子,C1-4亚烷基,C1-4亚烷基氧基或氧-C1-4亚烷基,k值为0或1,Q是CH或一个氮原子,R2是一个氢原子,卤原子,C1-6烷基,C1-6烷氧基,三氟甲基或三氟甲氧基,m是1-5的整数,假如当m值是2或更大时,R2可以是相同或不同原子或基团的任意组合。
2.一种权利要求1的三唑衍生物,其中所说的R1是一个直链或支链的C1-6烷基,X是一个卤原子或为直链或支链的C1-4烷基,n是1-3的整数,假如n值是2或3,X可以是相同或不同的原子或基团的任意组合;Y是直链或支链的C7-20烷基,C6-12环烷基烷基,直链或支链的C7-16烷氧基,C7-12环烷基烷氧基,直链或支链的C7-16烷硫基,直链或支链的C3-16烯基,直链或支链C3-16炔基,C5-12环烷基炔基,三(C1-4烷基)甲硅烷基C1-4烷氧基或一个可被所说的式(1)代表的基团,其中A是一个氧原子,硫原子,C1-4亚烷基,亚甲基氧基或氧亚甲基,K值是0或1,Q是CH或一个氮原子,R2是一个氢原子,卤原子,C1-4烷基,C1-4烷氧基,三氟甲基或三氟甲氧基,m是1-3的整数,如果当m值是2或3时,则R2可以是相同或不同的原子或基团的任意组合。
3.一种权利要求2的三唑衍生物,其中所说的R1是甲基。
4.一种含有权利要求1的三唑衍生物作为活性组份的杀虫剂。
5.一种含有权利要求1的三唑衍生物作为活性组份的杀螨剂。
6.一种生产具有下列通式〔I〕的三唑衍生物的方法:其中R1是一个C1-6烷基,X是一个卤原子或C1-6烷基,n值是1-5的整数,若当n值是2或更大时,X可以是相同或不同的原子或基团的任意组合;Y是一个C3-16烯基、C3-16炔基、C3-16烷硫基烷基、C6-12环烷基烷氧基、C6-12环烷基烷基、C5-12环烷基炔基,三C1-6烷基甲硅烷基C1-6烷氧基,C7-20烷基,C7-16烷氧基,C7-16烷硫基,或一个可被下列通式(1)表示的基团:其中A是一个氧原子,硫原子,C1-4亚烷基,C1-4亚烷基氧基或氧-C1-4亚烷基,k值为0或1,Q是CH或一个氮原子,R2是一个氢原子,卤原子,C1-6烷基,C1-6烷氧基,三氟甲基或三氟甲氧基,m是1-5的整数,假如当m值是2或更大时,R2可以是相同或不同原子或基团的任意组合,它包括把一种由下列通式〔II〕代表的化合物:其中W是一个硫原子或氧原子,L是一个C1-4烷基,X,n和Y的意义与上面叙述的相同,与一种由通式III为R1NHNH2的肼衍生物进行反应,其中R1的意义与上面叙述的相同。
7.一种生产具有下列通式〔I〕的三唑衍生物的方法:其中R1是一个C1-6烷基,X是一个卤原子或C1-6烷基,n值是1-5的整数,若当n值是2或更大时,X可以是相同或不同的原子或基团的任意组合;Y是一个C3-16烯基、C3-16炔基、C3-16烷硫基烷基、C6-12环烷基烷氧基、C6-12环烷基烷基、C5-12环烷基炔基,三C1-6烷基甲硅烷基C1-6烷氧基,C7-20烷基、C7-16烷氧基,C7-16烷硫基,或一个可被下列通式(1)表示的基团:其中A是一个氧原子,硫原子,C1-4亚烷基,C1-4亚烷基氧基或氧-C1-4亚烷基,k值为0或1,Q是CH或一个氮原子,R2是一个氢原子,卤原子,C1-6烷基,C1-6烷氧基,三氟甲基或三氟甲氧基,m是1-5的整数,假如当m是2或更大时,R2可以是相同或不同原子或基团的任意组合,它包括把一种由下列通式〔VI〕所代表的化合物:其中R1,X和n的意义与上面的叙述相同,R3是苯或被一个含有1-4个碳原子数的烷基取代的苯,与一种由下列通式〔VII〕代表的苯腈衍生物:其中Y的意义与上面叙述的相同,在Lewis酸存在的条件下进行反应。
8.一种生产具有下列通式〔I〕的三唑衍生物的方法:其中R1是一个C1-6烷基,X是一个卤原子或C1-6烷基,n值是1-5的整数,若当n值是2或更大时,X可以是相同或不同的原子或基团的任意组合;Y是一个C3-16烯基、C3-16炔基、C3-16烷硫基烷基、C6-12环烷基烷氧基、C6-12环烷基烷基、C5-12环烷基炔基,三C1-6烷基甲硅烷基C1-6烷氧基,C7-20烷基,C7-16烷氧基,C7-16烷硫基,或一个可被下列通式(1)表示的基团:其中A是一个氧原子,硫原子,C1-4亚烷基,C1-4亚烷基氧基或氧-C1-4亚烷基,k值为0或1,Q是CH或一个氮原子,R2是一个氢原子,卤原子,C1-6烷基,C1-6烷氧基,三氟甲基或三氟甲氧基,m是1-5的整数,假如当m值是2或更大时,R2可以是相同或不同原子或基团的任意组合,它包括把由下列通式〔VIII〕表示的化合物:其中R1,X和n的意义与上面叙述的相同,R3是苯或被一个含有1-4个碳原子数的烷基所取代的苯,与一个由下列通式〔V〕表示的化合物进行反应其中Z是卤原子,Y的意义与上面叙述的相同。
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CN103491782B (zh) * | 2011-02-09 | 2016-02-24 | 陶氏益农公司 | 杀虫组合物及其相关方法 |
BR112016022451B1 (pt) * | 2014-04-24 | 2021-03-30 | Sumitomo Chemical Company, Limited | Composto de diaril-azol e agente de controle de peste artrópoda |
Family Cites Families (4)
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NL7112373A (zh) * | 1970-09-25 | 1972-03-28 | ||
EP0036711B1 (en) * | 1980-03-22 | 1985-12-04 | Fbc Limited | Pesticidal heterocyclic compounds, processes for preparing them, compositions containing them, and their use |
AR241530A1 (es) * | 1984-12-21 | 1992-08-31 | Ciba Geigy A G Cesionaria De F | 1,2,4-triazoles, composicion para el control de pestes y procedimiento para la preparacion de 1,2,4-triazoles. |
DE3631511A1 (de) * | 1986-09-12 | 1988-03-24 | Schering Ag | 5-halogen-1,2,4-triazole, verfahren zu ihrer herstellung und ihre verwendung als akarizide und insektizide mittel |
-
1992
- 1992-10-01 TW TW081107807A patent/TW226993B/zh active
- 1992-10-06 US US07/956,984 patent/US5318959A/en not_active Expired - Lifetime
-
1993
- 1993-05-13 ES ES93303700T patent/ES2090871T3/es not_active Expired - Lifetime
- 1993-05-13 DE DE69303864T patent/DE69303864T2/de not_active Expired - Fee Related
- 1993-05-13 EP EP93303700A patent/EP0572142B1/en not_active Expired - Lifetime
- 1993-05-28 BR BR9302097A patent/BR9302097A/pt not_active IP Right Cessation
- 1993-05-28 RU RU93005069A patent/RU2114107C1/ru not_active IP Right Cessation
- 1993-05-28 CN CN93106496A patent/CN1037965C/zh not_active Expired - Fee Related
- 1993-05-29 KR KR1019930009434A patent/KR100255420B1/ko not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
DE69303864T2 (de) | 1997-03-20 |
EP0572142A3 (en) | 1994-03-23 |
US5318959A (en) | 1994-06-07 |
EP0572142B1 (en) | 1996-07-31 |
KR930023352A (ko) | 1993-12-18 |
KR100255420B1 (ko) | 2000-05-01 |
ES2090871T3 (es) | 1996-10-16 |
TW226993B (zh) | 1994-07-21 |
BR9302097A (pt) | 1993-12-07 |
DE69303864D1 (de) | 1996-09-05 |
EP0572142A2 (en) | 1993-12-01 |
RU2114107C1 (ru) | 1998-06-27 |
CN1079221A (zh) | 1993-12-08 |
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