CN1310926C - 邻苯二甲酰胺类化合物、它们的制备方法和它们作为杀虫剂的应用 - Google Patents
邻苯二甲酰胺类化合物、它们的制备方法和它们作为杀虫剂的应用 Download PDFInfo
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- CN1310926C CN1310926C CNB028078209A CN02807820A CN1310926C CN 1310926 C CN1310926 C CN 1310926C CN B028078209 A CNB028078209 A CN B028078209A CN 02807820 A CN02807820 A CN 02807820A CN 1310926 C CN1310926 C CN 1310926C
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- phthalyl
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- 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
- 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
-
- 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
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
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- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明涉及新的式(I)的邻苯二甲酰胺类化合物,其中X、Y、n、m、R1、R2、R3、R4、R5、R6、R7、A、a、b和c如说明书中所定义。本发明还涉及所述物质的制备方法和它们用于防治害虫的用途。
Description
本发明涉及新的邻苯二甲酰胺类化合物、它们的制备方法和它们作为杀虫剂的应用。
已知许多邻苯二甲酰胺类化合物具有杀虫作用(参见EP0919542A和EP1006107A)。然而,就它们与植物的相容性和效率而言,所述的已知化合物并不总是让人满意。已经发现,在侧链中含有硅原子的邻苯二甲酰胺类化合物具有非常好的杀虫和杀螨性能并被植物很好地耐受。
因此,本发明提供式(I)的邻苯二甲酰胺类化合物:
其中
X和Y彼此独立地表示氢、卤素、氰基、硝基、烷基、卤代烷基、烷氧基、卤代烷氧基、环烷基、卤代环烷基、环烷基氧基、卤代环烷基氧基、-S(O)d-烷基、-S(O)d-卤代烷基,或表示各任选被取代的苯基、苯氧基、杂芳基或杂芳基氧基,
n 表示1、2、3或4,
m 表示1、2、3、4或5,
R1、R2、R3和R4彼此独立地表示氢、烷基、卤代烷基或环烷基,
R5、R6和R7彼此独立地表示烷基或烷氧基,
A 表示-S(O)d-或氧,
a 表示1、2、3或4,条件是,如果a表示2、3或4,则重复单元-CR1R2-可以具有相同或不同的意义,
b 表示0或1,
c 表示0、1、2、3或4,条件是,如果c表示2、3或4,则重复单元-CR3R4-可以具有相同或不同的意义,
d 表示0、1或2。
根据取代基的性质和数目,式(I)化合物可以任选地以几何和/或光学异构体、区域异构体和/或构型异构体或各种组成的异构体的混合物存在。本发明要求保护的是纯的异构体和异构体混合物两者。
此外,现已发现,式(I)的新化合物可以通过下述方法获得:使式(II)的酰亚胺与式(III)的甲硅烷基胺任选地在稀释剂存在下反应,
式中
X、Y、n和m具有上面给出的含义,
H2N-(CR1R2)a-Ab-(CR3R4)c-Si(R5R6R7) (III)
式中
R1、R2、R3、R4、R5、R6、R7、A、a、b和c具有上面给出的含义。
最后,已经发现,本发明的式(I)化合物具有非常好的杀虫性能并且可以用于作物保护和材料保护中以防治不希望的害虫如昆虫和螨。令人惊奇的是,本发明的在侧链中含有硅原子的邻苯二甲酰胺类化合物具有非常好的杀虫和杀螨活性并被植物很好地耐受。
式(I)提供了本发明的邻苯二甲酰胺类化合物的一般定义。
X和Y彼此独立地
优选表示氢、卤素、氰基、硝基、C1-C6-烷基、C1-C6-卤代烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C3-C6-环烷基、C3-C6-卤代环烷基、C3-C6-环烷基氧基、C3-C6-卤代环烷基氧基、-S(O)d-C1-C6-烷基、-S(O)d-C1-C6-卤代烷基,或表示苯基、苯氧基、杂芳基或杂芳基氧基,它们各任选被相同或不同的选自卤素、C1-C6-烷基和C1-C6-卤代烷基的取代基单至四取代。
X和Y还彼此独立地
优选表示苯基、苯氧基、杂芳基或杂芳基氧基,它们各任选被相同或不同的选自C1-C6-烷氧基、C1-C6-卤代烷氧基、C1-C6-烷硫基和C1-C6-卤代烷硫基的取代基单至四取代。
n
优选表示1、2或3。
m
优选表示1、2、3或4。
R1、R2、R3和R4彼此独立地
优选表示氢、C1-C6-烷基、C1-C6-卤代烷基或C3-C6-环烷基。
R5、R6和R7彼此独立地
优选表示C1-C6-烷基或C1-C6-烷氧基。
A
优选表示-S(O)d-或氧。
a
优选表示1、2、3或4,条件是,如果a表示2、3或4,则重复单元-CR1R2-可以具有相同或不同的意义。
b
优选表示0或1。
c
优选表示0、1、2、3或4,条件是,如果c表示2、3或4,则重复单元-CR3R4-可以具有相同或不同的意义。
d
优选表示0、1或2。
X和Y彼此独立地
特别优选表示氢、氟、氯、溴、碘、氰基、硝基、C1-C4-烷基、具有1-9个氟、氯和/或溴原子的C1-C4-卤代烷基、C1-C4-烷氧基、具有1-9个氟、氯和/或溴原子的C1-C4-卤代烷氧基、C3-C6-环烷基、-S(O)d-C1-C4-烷基、具有1-9个氟、氯和/或溴原子的-S(O)d-C1-C4-卤代烷基。
Y 还
特别优选表示苯基、苯氧基、具有1-4个包括0-4个氮原子、0-2个不相邻的氧原子和/或0-2个不相邻的硫原子在内的杂原子的5-或6-元杂芳基或杂芳基氧基(特别是呋喃基、呋喃基氧基、噻吩基、噻吩基氧基、吡咯基、吡咯基氧基、四唑基、吡啶基、吡啶基氧基、嘧啶基、嘧啶基氧基、哒嗪基、哒嗪基氧基、吡嗪基、吡嗪基氧基),它们各任选被相同或不同的选自氟、氯、溴、碘、C1-C4-烷基、具有1-9个氟、氯和/或溴原子的C1-C4-卤代烷基、C1-C4-烷氧基、具有1-9个氟、氯和/或溴原子的C1-C4-卤代烷氧基、C1-C4-烷硫基、具有1-9个氟、氯和/或溴原子的C1-C4-卤代烷硫基的取代基单至四取代。
n
特别优选表示1或2。
m
特别优选表示1、2或3。
R1、R2、R3和R4彼此独立地
特别优选表示氢、C1-C4-烷基、具有1-9个氟、氯和/或溴原子的C1-C4-卤代烷基或C3-C6-环烷基。
R5、R6和R7彼此独立地
特别优选表示C1-C3-烷基或C1-C3-烷氧基。
A
特别优选表示-S(O)d-或氧。
a
特别优选表示1、2或3,条件是,如果a表示2或3,则重复单元-CR1R2-可以具有相同或不同的意义。
b
特别优选表示0或1。
c
特别优选表示0、1、2或3,条件是,如果c表示2或3,则重复单元-CR3R4-可以具有相同或不同的意义。
d
特别优选表示0、1或2。
X
非常特别优选表示氯、溴、碘。
Y
非常特别优选表示甲基、乙基、正丙基、异丙基、三氟甲基、五氟乙基、正七氟丙基、异七氟丙基、三氟甲氧基或-OCF2CF2H。
Y 还
非常特别优选表示苯氧基、吡啶基氧基或四唑基,它们各任选被相同或不同的的选自氟、氯、溴、碘、甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、-CF3、-CHF2、-CClF2、-CF2CHFCl、-CF2CH2F、-CF2CCl3、-CH2CF3、-CF2CHFCF3、-CH2CF2H、-CH2CF2CF3、-CF2CF2H、-CF2CHFCF3、-OCF3、-OCHF2、-OCF2CF2H、-SCF3、-SCHF2的取代基单至三取代。
n
非常特别优选表示1。
m
非常特别优选表示2。
R1、R2、R3和R4彼此独立地
非常特别优选表示氢、甲基或乙基。
R5、R6和R7彼此独立地
非常特别优选表示甲基、乙基、甲氧基或乙氧基。
A
非常特别优选表示-S(O)d-或氧。
a
非常特别优选表示1、2或3,条件是,如果a表示2或3,则重复单元-CR1R2-可以具有相同或不同的意义。
b
非常特别优选表示0或1。
c
非常特别优选表示0、1或2,条件是,如果c表示2,则重复单元-CR3R4-可以具有相同或不同的意义。
d
非常特别优选表示0、1或2。
非常特别优选的还有式(I-a)的化合物
式中
Y1和Y2彼此独立地具有上面给出的基团Y的含义,
A 表示硫或氧,
b 表示0或1,和
X、R1、R2、R3、R4、R5、R6、R7、a和c具有上面给出的含义。
非常特别优选的还有式(I-b)的化合物
式中
Y1和Y2彼此独立地具有上面给出的基团Y的含义,
A 表示硫或氧,
b 表示0或1,和
X、R1、R2、R3、R4、R5、R6、R7、a和c具有上面给出的含义。
非常特别优选的还有式(I-a)和式(I-b)的化合物,其中A表示SO或SO2。
非常特别优选的还有式(I-a)和式(I-b)的化合物,其中Y1和Y2彼此独立地具有上面给出的基团Y的优选、特别优选或非常特别优选的含义,
A 表示S(O)d或氧,
b 表示0或1,
d 表示0、1或2,和
X、R1、R2、R3、R4、R5、R6、R7、a和c具有上面给出的优选、特别优选或非常特别优选的含义。
优选的还有其中R5、R6和R7各表示甲基的式(I)的化合物。
优选的还有其中A表示S、SO或SO2的式(I)的化合物。
优选的还有式(I-a)和(I-b)的化合物,其中Y1表示C1-C4-烷基,优选三氟甲基、五氟乙基、正七氟丙基、异七氟丙基,特别优选异七氟丙基。
优选的还有式(I-a)和(I-b)的化合物,其中Y2表示甲基。
饱和烃基,例如烷基,只要有可能它们就各可以是直链或支链的,包括与杂原子结合时,诸如在烷氧基中。
然而,也可以将上述一般或优选的基团定义或说明按需要,即在各自范围和优选范围之间,相互组合。所述定义不仅适用于终产物,而且相应地适用于前体和中间体。
使用4-氯-2-{2-甲基-4-[1,2,2,2-四氟-1-(三氟甲基)乙基]苯基}-1H-异吲哚-1,3(2H)-二酮和1-{[(三甲基甲硅烷基)甲基]硫基}-2-丙胺作为原料,本发明方法的过程可以用下列式子说明:
式(II)提供了进行本发明方法用作原料需要的酰亚胺的一般定义。在该式中,X、Y、n和m优选、特别优选和非常特别优选具有在对式(I)化合物描述时已经对这些基团作为优选、特别优选等述及的那些含义。
式(II)的酰亚胺是已知的(参见EP0919542A和EP1006107A)。
式(III)提供了进行本发明方法用作原料需要的甲硅烷基胺的一般定义。在该式中,R1、R2、R3、R4、R5、R6、R7、A、a、b和c优选、特别优选和非常特别优选具有在对式(I)化合物描述时已经对这些基团作为优选、特别优选等述及的那些含义。
一些式(III)的甲硅烷基胺是已知的(参见Tetrahedron Lett.1999,40,4467)。
式(III-a)的甲硅烷基胺,
H2N-(CR1R2)a-S-(CR3R4)c-Si(R5R6R7) (III-a)
其中
R1、R2、R3、R4、R5、R6、R7、a和c具有上面给出的含义,
可以通过例如使式(IV)的氮杂环丙烷
其中
R1和R2具有上面给出的含义,
与式(V)的硫醇
HS-(CR3R4)c-Si(R5R6R7) (V)
其中
R3、R4、R5、R6、R7和c具有上面给出的含义,
任选地在稀释剂(例如甲醇)存在下反应来制备(参见J.Org.Chem.,1963,
28,1496)。
用于进行本发明方法的合适的稀释剂各是所有的常规的惰性有机溶剂。优选使用任选被卤代的脂族的、环脂族的或芳族的烃类例如石油醚、己烷、庚烷、环己烷、甲基环己烷、苯、甲苯、二甲苯或十氢萘;氯苯、二氯苯、二氯甲烷、氯仿、四氯化碳、二氯乙烷或三氯乙烷;醚类例如乙醚、异丙醚、甲基叔丁基醚、甲基叔戊基醚、二氧六环、四氢呋喃、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷或苯甲醚;腈类例如乙腈、丙腈、正或异丁腈或苄腈;酰胺类例如N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基甲酰苯胺、N-甲基吡咯烷酮或六甲基磷酸三酰胺;酯类例如乙酸甲酯或乙酸乙酯;砜类例如二甲基亚砜;或砜类例如环丁砜;羧酸类例如甲酸或乙酸。特别优选本发明方法在乙酸中或不存在稀释剂的情况下进行。
当进行本发明的方法时,反应温度各可以在较宽的范围内变化。通常,该方法在20℃至150℃、优选50℃至120℃之间的温度下进行。
当进行本发明的方法时,通常,就每摩尔式(II)化合物而言使用1-3mol的式(III)化合物。然而,也可以使用其他比例的反应组分。后处理通过常规方法进行。通常,将反应混合物浓缩,将残留物加入适当的溶剂中通过色谱法除去产物中可能仍然存在的任何杂质。
所有本发明的方法通常都是在大气压下进行的。然而,每种情况下也都可以在加压或减压下进行。
本发明活性化合物适合防治在农业中、林业中、储藏产品和材料的保护中以及卫生领域中遇到的动物害虫,特别是昆虫、蛛形纲和线虫,并被植物很好地耐受和对温血动物具有有利的毒性。它们可以优选被用作植物保护剂。它们对普通敏感和抗性种类以及对所有或某些发育阶段具有活性。上述害虫包括:
来自等足目(Isopoda),例如Oniscus aselluse,鼠妇(Armadillidium vulgare)和Porcellio scaber。
来自多足纲目(Diplopoda),例如Blaniulus gutttulatus。
来自唇足亚纲目(Chilopoda),例如Geophilus carpophagus和蛐蜒目种(Scutigera spec.)。
来自综合纲目(Symphyla),例如Scutigerella immaculata。
来自缨尾目(Thysanura),例如西洋衣鱼(Lepisma saccharina)。
来自弹尾目(Collembola),例如Onychiurus armatus。
来自直翅目(Orthoptera),例如灶马(Acheta domesticus),蝼蛄属(Gryllotalpa spp.),热带飞蝗(Locusta migratoria migratorioides),长额负蝗(Melanoplus spp.)和Schistocerca gregaria。
来自非蠊目(Blattaria),例如东方非蠊(Blatta orientalis),美洲大蠊(Periplaneta americana),马德拉非蠊(Leucophaea maderae),德国小蠊(Blattella germanica),
来自革翅目(Dermaptera),例如欧洲球螋(Forficulaauricularia)。
来自等翅目(Isoptera),例如白蚁属(Reticulitermes spp.)。
来自虱目(Phthiraptera),例如头虱(Pediculus humanuscorporis),盲虱属(Haematopinus spp.)和长额虱(Linognathus spp.),例如羽虱属(Trichodectes spp.)和Damalinea spp.。
来自缨翅目(Thysanoptera),例如温室条蓟马(Hercinothripsfemoralis)和棉蓟马(Thrips tabaci),Thrips palmi和Frankliniellaaccidentalis。
来自异翅亚目(Heteroptera),例如褐盾蝽属(Eurygasterspp.),Dysdercus intermedius,甜菜拟网蝽(Piesma quadrata),臭虫(Cimex lectularius),Rhodnius prolixus和吸血猎蝽属(Triatomaspp.)。
来自同翅亚目(Homoptera),例如Aleurodes brassicae,棉粉虱(Bemisia tabaci),温室白粉虱(Trialeurodes vaporariorum),棉蚜(Aphis gossypii),甘蓝蚜(Brevicoryne brassicae),茶鹿隐瘤额蚜(Cryptomyzus ribis),蚕豆蚜(Aphis fabae),苹果蚜(Aphis pomi),苹果绵蚜(Eriosoma lanigerum),桃大尾蚜(Hyalopterus arundinis),葡萄根瘤蚜(Phylloxera vastatrix),瘿绵蚜属(Pemphigusspp.),Macrosiphum avenae,瘤额蚜(Myzus spp.),忽布瘤额蚜(Phorodon humuli),粟缢管蚜(Rhopasiphum padi),叶蝉属(Empoascaspp.),Euscelis bilobatus,黑尾叶蝉(Nephotettix cincticeps),李蜡蚧(Lecanium corni),油橄榄盔(Saissetia oleae),稻灰飞虱(Laodelphax striatellus),褐稻虱(Nilaparvata lugens),红圆蚧(Aonidiella aurantii),Aspidiotus hederae,粉蚧属(Pseudococcusspp.)和木虱属(Psylla spp.)。
来自鳞翅目(Lepidoptera),例如,红铃虫(Pectinophoragossypiella),松尺蠖(Bupalus piniarius),Cheimatobia brumata,Lithocolletis blancardella,樱桃巢蛾(Hyponomeuta padella),小菜蛾(Plutella xylostella),天幕毛虫(Malacosoma neustria),Euproctis chrysorrhoea,毒蛾属(Lymantria spp.),棉叶穿孔潜蛾(Bucculatrix thurberiella),Phyllocnisti citrella,地老虎(Agrotis spp.),切根虫(Euxoa spp.),褐夜蛾(Feltia spp.),埃及金刚钻(Earias insulana),夜蛾属(Heliothis spp.),甘蓝夜蛾(Mamestra brassicae),Panolis flammea,夜蛾属(Spodoptera spp.),粉纹夜蛾(Trichoplusia ni),苹果蠹蛾(Carpocapsa pomonella),粉蝶属(Pieris spp.),螟(Chilo spp.),Pyrausta nubilalis,Ephestiakuehniella,大黄螟(Galleria mellonella),袋衣蛾(Tineolabisselliella),网衣蛾(Tinea pellionella),褐织叶蛾(Hofmannophila pseudospretella),Cacoecia podana,Capuareticulana,云杉卷叶蛾(Choristoneura fumiferana),葡萄果蠹蛾(Clysia ambiguella),茶黄卷叶蛾(Homona magnanima),栎绿卷叶蛾(Tortrix viridana),卷螟属(Cnaphalocerus spp.),Oulema oryzae。
来自鞘翅目(Coleoptera),例如,家具窃蠹(Anobium punctatum),Rhizopertha dominica,Bruchidius obtectus,大豆象(Acanthoscelides obtectus),家天牛(Hylotrupes bajulus),Agelastica alni,甲铃薯甲虫(Leptinotarsa decemlineata),Phaedoncochleariae,叶甲属(Diabrotica spp.),油菜兰跳甲(Psylliodeschrysocephala),墨西哥豆瓢虫(Epilachna varivestis),Atomariaspp.,锯胸谷盗(Oryzaephilus surinamens),象甲属(Anthonomusspp.),米象属(Sitophilus spp.),Otiorrhynchus sulcatus,香蕉蛛基象甲(Cosmopolites sordidus),Ceuthorrhynchus assimilis,苜宿叶象甲(Hypera posttica),皮蠹属(Dermestes spp.),皮蠹属(Trogoderma spp.),皮蠹属(Anthrenus spp.),黑皮蠹(Attagenuespp.),粉蠹(Lyctus spp.),Meligethes aeneus,蛛甲属(Ptinus spp.),金黄蛛甲(Niptus bdoleucus),麦蛛甲(Gibbium psylliodes),拟谷稻属(Tribolium spp.),黄粉甲(Tenebrio molitor),扣甲属(Agriotesspp.),金针虫属(Conoderus spp.),Melolontha meiolontha,六月金龟子(Amphimallon solstitialis),Costelytra zealandica和Lissorhoptrus oryzophilus。
来自膜翅属(Hymenoptera),例如锯角叶蜂属(Diprion spp.),叶蜂属(Hoplocampa app.),蚁(Lasius spp.),厨蚁(Monomoriumpharaonis),和胡蜂(Vespa spp.)。
来自双翅属(Diptera),例如,咿蚊(Aedes spp.),斑按蚊属(Anopheles spp.),库蚊(Culex spp.),黄猩猩果蝇(Drosophilamelanogaster),家蝇(Musca spp.),厩蝇(Fannia spp.),红头丽蝇(Calliphora erythrocephala),丝光绿蝇(Lucilia spp.),Chrysomyiaspp.,疽蝇属(Cuterebra spp.),Gastrophilus spp.,Hyppobosca spp.,螫蝇属(Stomoxys spp.),鼻蝇属(Oestrus spp.),皮蝇属(Hydodermaspp.),牛虻属(Tabanus spp.),Tannia spp.,Bibio hortulanus,瑞典麦杆蝇(Oscinella frit),麦蝇(Phorbia spp.),甜菜潜叶花蝇(Pegomyia hyoscyami),地中海实蝇(Ceratitis capitata),油橄榄实蝇(Dacus oleae)和欧洲大蚊(Tipula paludosa),种蝇属(Hylemyiaspp.)和潜蝇属(Liriomyza spp.)。
来自蚤目(Siphonaptera),例如,东方鼠蚤(Xenopsylla cheopis),和角叶蚤属(Ceratophyllus spp.)。
来自蛛形纲(Arachnida),例如Sciopio maurus,黑寡妇球腹蛛(Latrodectus mactans)。粗脚粉螨(Acarus siro),隐喙蚍(Argas spp.),喙蜱属(Ornithodoros spp.),鸡皮刺螨(Dermanyssus gallinae),Eriophyes ribis,橘锈螨(Phyllocoptruta oleivora),牛蜱属(Boophilus spp.),头蜱属(Rhipicephalus spp.),花蜱属(Amblyommaspp.),Hyalomma spp.,硬蚍(Ixodes spp.),蛘螨属(Psoroptes spp.),恙螨属(Chorioptes spp.),疥螨(Sarcoptes spp.),线螨属(Tarsonemus spp.),苜宿苔螨(Bryobia praetiosa),红蜘蛛(Panonychus spp.),和红叶螨属(Tetranychus spp.),Hemitarsonemusspp.,短须螨属(Brevipalpus spp.)。
寄生植物线虫包括例如短体线虫属(Pratylenchus spp.),相似穿孔线虫(Radopholus similis),起绒草茎线虫(Ditylenchus dipsaci),半穿刺线虫(Tylenchulus semipenetrans),异皮线虫属(Heteroderaspp.),球异皮线虫属(Globodera spp.),根结线虫属(Meloidogynespp.),滑刃线虫属(Aphelenchoides spp.),长针线虫属(Longidorusspp.),剑线虫属(Xiphinema spp.)和毛刺线虫属(Trichodorusspp.),Bursaphelenchus spp.。
特别是,本发明的式(I)化合物具有优良的抗毛虫、甲虫幼虫、蜘蛛螨类、蚜虫和细蛾。
任选地,本发明的式(I)化合物在某些浓度或施用率时也可以用作除草剂或杀微生物剂,例如杀霉菌剂、杀真菌剂和杀细菌剂。任选地,它们也可以用作合成其他活性化合物的中间体或前体。
根据本发明,可以处理所有植物和植物各部分。此处植物可以理解为所有植物以及植物群落如需要和不需要的野生植物或农作物(包括自然长出的农作物)。农作物可以是通过常规植物育种和优化方法或通过生物技术和重组方法或上述方法的结合获得的植物,包括转基因植物以及包括可获得或不能获得植物品种保护的植物品种,植物的各部分应理解为植物的所有地上和地下部分以及器官,如茎、叶、花和根,可提及的实例为叶片、针叶、叶柄、树干、花、子实体、果实、种子、根、块茎和根状茎。植物各部分还包括收获材料以及无性和有性繁殖材料,例如插条、块茎、根状茎、压枝和种子。
采用活性化合物进行植物和植物各部分的本发明处理方法是通过常规处理方法直接施用或将化合物作用于它们的环境、栖息地或贮藏区进行处理,例如浸渍、喷雾、熏蒸、弥雾、撒播、刷涂以及在繁殖材料特别是种子的情况下还可以进行一层或多层包衣。
本发明活性化合物可被转化成为常规制剂如溶液剂、乳剂、可湿性粉剂、悬浮剂、粉剂、细粉剂、糊剂、可溶性粉剂、颗粒剂、浓悬浮乳剂、用活性化合物浸渍的天然和合成材料以及聚合物包封的微胶囊剂。
这些制剂是以已知方法制备的,例如通过将活性化合物与填充剂,即液体溶剂和/或固体载体混合而生产,制剂中任选使用表面活性剂,即乳化剂和/或分散剂和/或发泡剂。
在使用水作为填充剂的情况下,例如,也可使用有机溶剂作为助溶剂。适合的液体溶剂主要有:芳香烃类,如二甲苯、甲苯或烷基萘;氯代芳烃类或氯代脂肪烃类,如氯苯、氯乙烯或二氯甲烷;脂肪烃类,如环己烷或链烷烃,例如矿物油馏份、矿物油和植物油;醇类,如丁醇或乙二醇及其醚和酯类,酮类,如丙酮、甲基乙基酮、甲基异丁基酮或环己酮;强极性溶剂,如二甲基甲酰胺和二甲基亚砜,以及水。
适合的固体载体有:
例如,铵盐和天然矿物粉末,如高岭土、粘土、滑石、白垩、石英、硅镁土、蒙脱土或硅藻土,和合成矿物粉末,如高分散二氧化硅、氧化铝和硅酸盐;适合颗粒剂的固体载体有:例如,粉碎和分级的天然岩石,如方解石、大理石、浮石、海泡石和白云石,以及合成的无机和有机粉末颗粒,以及有机材料的颗粒如锯末、坚果壳、玉米穗茎和烟草茎;
适合的乳化剂和/或发泡剂有:例如非离子和阴离子乳化剂,如聚氧乙烯脂肪酸酯、聚氧乙烯脂肪醇醚,例如烷基芳基聚乙二醇醚、烷基磺酸盐、烷基硫酸盐、芳基磺酸盐以及蛋白水解产物;
适合的分散剂有:例如木素亚硫酸废液和甲基纤维素。
在制剂中还可使用粘着剂如羧甲基纤维素和粉末、颗粒或胶乳状的天然或合成聚合物,如阿拉伯树胶、聚乙烯醇和聚乙酸乙烯酯,以及天然磷脂如脑磷脂和卵磷脂和合成磷脂。其它添加剂可以是矿物油和植物油。
可以使用着色剂如无机颜料,例如氧化铁、氧化钛和普鲁士兰,和有机染料,如茜素染料、偶氮染料和金属酞菁染料,和痕量营养物如铁、锰、硼、铜、钴、钼和锌的盐。
制剂中通常含有按重量计0.1-95%,优选0.5-90%的活性化合物。
本发明活性化合物可以其市售通用制剂和从上述制剂制备的应用形式,与其它活性化合物的混合物的形式存在,其它活性化合物如杀虫剂、引诱剂、消毒剂、杀细菌剂、杀螨剂、杀线虫剂、杀真菌剂、植物生长调节剂或除草剂。杀虫剂包括,例如磷酸酯类、氨基甲酸酯类、羧酸酯类、氯代烃类、苯基脲类和从微生物中生产的物质等。
混合物中共同成分的特别有利的例子是下面的化合物:
杀真菌剂:
aldimorph,氨丙磷酸,氨丙磷酸钾盐,andoprim,敌菌灵,戊环唑,azoxystrobin,
苯霜灵,邻碘酰苯胺,苯菌灵,benzamacril,benzamacril-isobutyl,双丙氨酰磷,乐杀螨,联苯,双苯三唑醇,灭瘟素,糠菌唑,乙嘧酚磺酸酯,丁赛特,
石硫合剂,capsimycin,敌菌丹,克菌丹,多菌灵,萎锈灵,carvon,灭螨猛,灭瘟唑,chlorfenazole,地茂散,氯化苦,百菌消,乙菌利,clozylacon,代森盐,霜尿氰,环唑醇,cyprodinil,酯菌胺,
debacarb,双氯酚,苄氯三唑醇,diclofluanid,哒菌清,氯硝胺,乙霉威,醚唑,二甲嘧吩,烯酸吗啉,烯唑醇(diniconazole),烯唑醇(diniconazole-M),二硝巴豆酸酯,二苯胺,吡菌硫,灭菌磷,二噻农,十二环吗啉,多果定,联氨唑酮,
克瘟散,epoxyconazole,乙环唑,乙嘧酚,土菌灵,
famoxadon,咪菌腈,氯苯嘧啶醇,fenbuconazole,甲呋酰苯胺,种衣酯,拌种咯,苯锈啶,丁苯吗啉,三苯基醋酸锡,三苯基氢氧化锡,福美铁,嘧菌腙,氟啶胺,flumetover,氟氯菌核利,fluquinconazole,调嘧醇,氟硅唑,磺菌胺,氟酰胺,粉唑醇,灭菌丹,乙磷铝,乙磷钠,四氯苯酞,麦穗宁,呋霜灵,furametpyr,二甲呋酰苯胺,呋菌唑,呋醚唑,拌种胺,
谷种定,
六氯苯,己唑醇,霉灵,
抑霉唑,酰胺唑,双胍辛醋酸盐(iminoctadine,iminoctadinealbesilate,iminoctadine triacetate),iodocarb,ipconazole,异稻瘟净(IBP),异菌脲,irumamycin,稻瘟灵,isovaledione,
春雷霉素,kresoxim-methyl,铜制剂,例如:氢氧化铜,环烷酸铜,氯氧化铜,硫酸铜,氧化铜,8-羟基喹啉铜和波尔多液,
代森锰铜,代森锰,代森锰锌,meferimzone,嘧菌胺,灭锈胺,甲霜灵,metconazole,磺菌威,呋菌胺,代森联,氯苯咯菌胺,噻菌胺,米多霉素,腈菌唑,甲菌利,
二甲基二硫氨基甲酸镍,nitrothal-isopropyl,氟苯嘧啶醇,
甲呋酰胺,霜灵,oxamocarb,喹菌酮,氧化萎锈灵,oxyfenthiin,
稻瘟酯,戊菌唑,戊菌隆,稻瘟磷,四氯苯酞,多马霉素,病花灵,聚氨基甲酸酯,多氧霉素,烯病异噻唑,味鲜安,腐霉利,丙酰胺,propanosine-sodium,环丙唑,丙森锌,吡嘧磷,啶斑肟,pyrimethanil,咯喹酮,氯吡呋醚,
quinconazole,五氯硝基苯(PCNB),
硫和硫制剂,
戊唑醇,叶枯酞,四氯硝基苯,调环烯,氟嘧唑,噻菌灵,噻菌腈,thifluzamide,甲基硫菌灵,福美双,tioxymid,甲基立枯磷,甲基氟磺胺,三唑酮,三唑醇,triazbutil,唑菌嗪,杨菌胺,三环唑,十三吗啉,氟菌唑,嗪氨灵,triticonazole,
烯效唑,
稻纹散,乙烯菌核利,烯霜苄唑,
zarilamide,代森锌,福美锌,还有
Dagger G,
OK-8705,
OK-8801,
α-(1,1-二甲基乙基)-β-(2-苯氧基乙基)-1H-1,2,4-三唑-1-乙醇,
α-(2,4-二氯苯基)-β-氟-b-丙基-1H-1,2,4-三唑-1-乙醇,
α-(2,4-二氯苯基)-β-甲氧基-a-甲基-1H-1,2,4-三唑-1-乙醇,
α-(5-甲基-1,3-二烷-5-基)-β-[[4-(三氟甲基)-苯基]-亚甲基]-1H-1,2,4-三唑-1-乙醇,
(5RS,6RS)-6-羟基-2,2,7,7-四甲基-5-(1H-1,2,4-三唑-1-基)-3-辛酮,
(E)-a-(甲氧基亚氨基)-N-甲基-2-苯氧基-苯基乙酰胺,
{2-甲基-1-[[[1-(4-甲基苯基)-乙基]-氨基]-羰基]-丙基}-氨基甲酸异丙酯,
1-(2,4-二氯苯基)-2-(1H-1,2,4-三唑-1-基)-乙酮-O-(苯基甲基)-肟,
1-(2-甲基-1-萘基)-1H-吡咯-2,5-二酮,
1-(3,5-二氯苯基)-3-(2-丙烯基)-2,5-吡咯烷二酮,
1-[(二碘代甲基)-磺酰基]-4-甲基-苯,
1-[[2-(2,4-二氯苯基)-1,3-二氧戊环-2-基]-甲基]-1H-咪唑,
1-[[2-(4-氯苯基)-3-苯基环氧乙烷基]-甲基]-1H-1,2,4-三唑,
1-[1-[2-[(2,4-二氯苯基)-甲氧基]-苯基]-乙烯基]-1H-咪唑,
1-甲基-5-壬基-2-(苯基甲基)-3-吡咯烷醇,
2′,6′-二溴-2-甲基-4′-三氟甲氧基-4′-三氟甲基-1,3-噻唑-5-N-碳酰苯胺,
2,6-二氯-N-[1-(4-氯苯基)-乙基]-1-乙基-3-甲基-环丙烷甲酰胺,
2,6-二氯-5-(甲硫基)-4-嘧啶基-硫代氰酸酯,
2,6-二氯-N-(4-三氟甲基苄基)-苯甲酰胺,
2,6-二氯-N-[[4-(三氟甲基)-苯基]-甲基]-苯甲酰胺,
2-(2,3,3-三碘代-2-丙烯基)-2H-四唑,
2-[(1-甲基乙基)磺酰基]-5-(三氯甲基)-1,3,4-噻二唑,
2-[[6-脱氧-4-O-(4-O-甲基-β-D-吡喃葡糖基)-α-D-吡喃葡糖基]-氨基]-4-甲氧基-1H-吡咯并[2,3-d]嘧啶-5-腈,
2-氨基丁烷,
2-溴-2-(溴代甲基)戊烷二腈,
2-氯-N-(2,3-二氢-1,1,3-三甲基-1H-茚-4-基)-3-吡啶甲酰胺,
2-氯-N-(2,6-二甲基苯基)-N-(异硫氰酸根合甲基)-乙酰胺,
2-苯基苯酚(OPP),
3,4-二氯-1-[4-(二氟甲氧基)-苯基]-1H-吡咯-2,5-二酮,
3,5-二氯-N-[氰基-[(1-甲基-2-丙炔基)-氧基]-甲基]-苯甲酰胺,
3-(1,1-二甲基丙基-1-氧代-1H-茚-2-腈,
3-[2-(4-氯苯基)-5-乙氧基-3-异唑烷基]-吡啶,
4-氯-2-氰基-N,N-二甲基-5-(4-甲基苯基)-1H-咪唑-1-磺酰胺,
4-甲基-四唑并[1,5-a]喹唑啉-5(4H)-酮,
8-(1,1-二甲基乙基)-N-乙基-N-丙基-1,4-二氧杂螺[4.5]癸烷-2-甲烷胺,
8-羟基喹啉硫酸盐,
9H-呫吨-2-[(苯基氨基)-羰基]-9-羧酸酰肼,
双-(1-甲基乙基)-3-甲基-4-[(3-甲基苯甲酰基)-氧基]-2,5-噻吩二羧酸酯,
顺-1-(4-氯代苯基)-2-(1H-1,2,4-三唑-1-基)-环庚醇,
顺-4-[3-[4-(1,1-二甲基丙基)-苯基-2-甲基丙基]-2,6-二甲基-吗啉]盐酸盐,
[(4-氯苯基)-偶氮]-氰基乙酸乙酯,
碳酸氢钾,
甲烷四硫醇钠盐,
1-(2,3-二氢-2,2-二甲基-1H-茚-1-基)-1H-咪唑-5-羧酸甲酯,
N-(2,6-二甲基苯基)-N-(5-异唑基羰基)-DL-丙氨酸甲酯,
N-(氯代乙酰基)-N-(2,6-二甲基苯基)-DL-丙氨酸甲酯,
N-(2,3-二氯-4-羟基苯基)-1-甲基-环己烷甲酰胺,
N-(2,6-二甲基苯基)-2-甲氧基-N-(四氢-2-氧代-3-呋喃基)-乙酰胺,
N-(2,6-二甲基苯基)-2-甲氧基-N-(四氢-2-氧代-3-噻吩基)-乙酰胺,
N-(2-氯-4-硝基苯基)-4-甲基-3-硝基-苯磺酰胺,
N-(4-环己基苯基)-1,4,5,6-四氢-2-嘧啶胺,
N-(4-己基苯基)-1,4,5,6-四氢-2-嘧啶胺,
N-(5-氯-2-甲基苯基)-2-甲氧基-N-(2-氧代-3-唑烷基)-乙酰胺,
N-(6-甲氧基)-3-吡啶基)-环丙烷甲酰胺,
N-[2,2,2-三氯-1-[(氯代乙酰基)-氨基]-乙基]-苯甲酰胺,
N-[3-氯代-4,5-双(2-丙炔基氧基)-苯基]-N′-甲氧基-甲亚氨酰胺,
N-甲酰基-N-羟基-DL-丙氨酸钠盐,
O,O-二乙基[2-(二丙基氨基)-2-氧代乙基]-乙基硫代氨基磷酸酯,
O-甲基S-苯基苯基丙基硫代氨基磷酸酯,
S-甲基1,2,3-苯并噻二唑-7-硫代甲酸酯,
螺[2H]-1-苯并吡喃-2,1′(3′H)-异苯并呋喃-3′-酮,
杀细菌剂:
bromopol,双氯酚,氯甲基吡啶,二甲基二硫氨基甲酸镍,春雷霉素,异噻唑酮,呋喃羧酸,oxytetracycline,烯异丙噻唑,链霉素,叶枯酞,硫酸铜和其它铜制剂。
杀昆虫剂/杀螨剂/杀线虫剂:
齐墩螨素,乙酰甲胺磷,Acetamiprid,氟酯菊酯,棉铃威,涕灭威,氧涕灭威,甲体氯氰菊酯(Alpha-cypermethrin,Alphamethrin),双虫脒,avermectin,AZ60541,azadirachtin,甲基吡磷,azinphos-A,保棉磷,三唑锡,
日本甲虫芽孢杆菌(Bacillus popilliae),球形芽孢杆菌(Bacillus sphaericus),枯草芽孢杆菌(Bacillus subtilis),苏云金芽孢杆菌(Bacillus thuringiensis),Baculoviren,蚕白僵菌(Beauveria bassiana),纤细白僵菌(Beauveria tenella),虫威,丙硫克百威,杀虫磺,苯螨特,氟氯氰菊酯,Bifenazate,氟氯菊酯,Bioethanomethrin,生物氯菊酯,BPMC,brofenpros A,溴硫磷,合杀威,噻嗪酮,丁酮威,butylpyridaben,
硫线磷,甲萘威,克百威,三硫磷,丁硫百克威,杀螟丹,Chloethocarb Chlorethoxyfos,Chlorfenapyr,毒虫畏,定虫隆,氯甲硫磷,毒死蜱,甲基毒死蜱,Chlovaporthrin,顺式-苄呋菊酯,顺式氯菊酯,clocythrin,除线威,四螨嗪,杀螟腈,Cycloprene,乙氰菊酯,氟氯氰菊酯-β,cyhalothrin,三环锡,氯氰菊酯,灭蝇胺,
溴氰菊酯,内吸磷-M,内吸磷-S,甲基内吸磷,杀螨隆,二嗪磷,敌敌畏,除虫脲,乐果,甲基毒虫畏,diofenolan,乙拌磷,docusat-sodium,dofenapyn,
克瘟散,emamectin,烯炔菊酯,硫丹,Entomopfthofa spp.,高氰戊菊酯,乙硫苯威,乙硫磷,灭线磷,Etofenprox,醚菊酯,乙嘧硫磷,
虫胺磷,喹螨醚,苯丁锡,杀螟硫磷,苯硫威,Fenoxacrim,双氧威,氯氰菊酯,fenpyrad,Fenpyrithrin,唑螨酯,氰戊菊酯,fipronil,氟定胺,Fluazuron,Flubrocythrinate,氟螨脲,氟氰戊菊酯,氟虫脲,Flutenzine,氟胺氰菊酯,地虫硫磷,丁苯硫磷,噻唑磷,fubfenprox,呋线威,
Granulosis viruses,
Halofenozide,HCH,庚烯磷,氟铃脲,噻螨酮,烯虫乙酯,
吡虫啉,氯唑磷,异丙胺磷,唑磷,ivermectin,
Nuclear polyhedrosis viruses,
氯氟氰菊酯,lufenuron,
马拉硫磷,灭蚜蜱,速灭磷,mesulfenphos,Metharhiziumanisopliae,Metharhizium flavoviride,蜗牛敌,虫螨畏,甲胺磷,杀扑磷,灭梭威,灭多威,速灭威,milbemectin,久效磷,
二溴磷,nitenpyram,Nithiazine,Novaluron,
氧乐果,杀线威,亚砜吸磷,
玫烟色拟青霉(Paecilomyces fumosofoseus),对硫磷-A,对硫磷-M,氯菊酯,稻丰散,甲拌磷,伏杀硫磷,亚胺硫磷,磷胺,辛硫磷,抗芽威,嘧啶磷-A,嘧啶磷-M,丙溴磷,猛杀威,残杀威,丙硫磷,发果,pymetrozine,吡唑硫磷,pyresmethrin,除虫菊酯,哒螨酮,Pyridathion,pyrimidifen,蚊蝇醚,
喹硫磷,
Ribavirin,
蔬果磷,sebufos,silafluofen,Spinosad,治螟硫磷,甲丙硫磷,
氟胺氰菊酯,tebufenozid,tebufenpyrad,tebupirimiphos,伏草隆,七氟菊酯,双硫磷,特灭威,特丁磷,杀虫畏,thetacypermethrin,蛾蝇腈,Thiatriphos,Thiocyclam hydrogenoxalate硫双威,久效磷,thuringiensin,二甲硫吸磷,虫线磷,四溴菊酯,苯噻螨,三唑磷,triazuron,Trichlophenidine,敌百虫,杀虫隆,混灭威,
芽灭多,Vaniliprole,Verticillium lecanii,
YI5302,
zeta-cypermethrin,Zolaprofos,
环丙烷羧酸(1R-顺式)-[5-(苯基甲基)-3-呋喃基]-甲基-3-[(二氢-2-氧代-3(2H)-亚呋喃基)-甲基]-2,2-二甲酯,
环丙烷羧酸(3-苯氧基苯基)-甲基-2,2,3,3-四甲酯,
1-[(2-氯-5-噻唑基)甲基]四氢-3,5-二甲基-N-硝基-1,3,5-三嗪-2(1H)-亚胺,
2-(2-氯-6-氟代苯基)-4-[4-(1,1-二甲基乙基)苯基]-4,5-二氢-唑,
2-(乙酰氧基)-3-十二烷基-1,4-萘二酮,
2-氯-N-[[[4-(1-苯基乙氧基)苯基]-氨基]-羰基]-苯甲酰基,
2-氯-N-[[[4-(2,2-二氯-1,1-二氟乙氧基)苯基]-氨基]-羰基]-苯甲酰基,
氨基甲酸3-甲基苯基丙酯,
4-[4-(4-乙氧基苯基)-4-甲基戊基]-1-氟-2-苯氧基-苯,
4-氯-2-(1,1-二甲基乙基)-5-[[2-(2,6-二甲基-4-苯氧基苯氧基)乙基]硫基]-3(2H)-哒嗪酮,
4-氯-2-(2-氯-2-甲基丙基)-5-[(6-碘-3-吡啶基)甲氧基]-3(2H)-哒嗪酮,
4-氯-5-[(6-氯-3-吡啶基)甲氧基]-2-(3,4-二氯苯基)-3(2H)-哒嗪酮,
苏云金芽孢杆菌菌株EG-2348,
[2-苯甲酰基-1-(1,1-二甲基乙基)-苯甲酰肼,
丁酸2,2-二甲基-3-(2,4-二氯苯基)-2-氧代-1-氧杂螺[4.5]十二烷-3-烯-4-酯,
[3-[(6-氯-3-吡啶基)甲基]-2-亚噻唑烷基]-氨腈,
二氢-2-(硝基亚甲基)-2H-1,3-噻嗪-3(4H)-甲醛,
[2-[[1,6-二氢-6-氧代-1-(苯基甲基)-4-哒嗪基]氧基]乙基]-氨基甲酸乙酯,
N-(3,4,4-三氟-1-氧代-3-丁烯基)-甘氨酸,
N-(4-氯苯基)-3-[4-(二氟甲氧基)苯基]-4,5-二氢-4-苯基-1H-吡唑-1-甲酰胺,
N-[(2-氯-5-噻唑基)甲基]-N′-甲基-N″-硝基-胍,
N-甲基-N′-(1-甲基-2-丙烯基)-1,2-肼二硫代二甲酰胺,
N-甲基-N′-2-丙烯基-1,2-肼二硫代二甲酰胺,
O,O-二乙基[2-(二丙基氨基)-2-氧代乙基]-乙基氨基硫代磷酸酯。
还可与其它已知活性化合物如除草剂或与肥料和植物生长调节剂混合。
当用作杀虫剂时,本发明活性化合物还可以其市售通用制剂和从上述制剂制备的应用形式,与增效剂混合使用。增效剂是能够增加活性化合物活性,但加入的增效剂本身不必须有活性的化合物。
从市售通用制剂制备的应用形式中活性化合物的含量可在很宽的范围内变化。使用形式中活性化合物的浓度为0.0000001至95重量%的活性化合物,优选0.0001至1重量%。
本发明化合物以适合于应用形式的常规方式施用。
当用于防治卫生害虫和储藏物品中的害虫时,活性化合物具有优异的木材和粘土残留活性以及对刷过石灰浆的基底具有很好的碱稳定性。
如上所提及,可按照本发明处理所有植物及其各部分。在一个优选的实施方案中,处理已有的或通过常规的生物育种方法,如杂交或原生质体融合得到的植物种类和植物品种和其各部分。在另一个优选的实施方案中,处理通过基因工程方法,任选与常规方法联合(基因修饰生物体)得到的转基因植物和植物品种及其各部分。术语“各部分”或“植物的各部分”或“植物部分”在上面已作过解释。
特别优选地,按照本发明处理在各种情况下市售可得的或在使用的植物品种(culticars)的植物。植物品种是指已通过常规育种、突变或重组DNA技术获得的具有特殊性能(“特性”)的植物。这可以是品种、生物型或基因型的。
根据植物种类或植物品种、它们的栖息地和生长条件(土壤、气候、植物生长期、营养),按照本发明的处理方法还可导致超加和的(“协同”)作用。因此,例如,可减少用量和/或拓宽活性谱和/或提高本发明所用的物质和组合物的活性、改善植物生长、增强对高或低温的耐受性、增强对旱灾或水灾或土壤盐量的耐受性、增加花卉的性能、易于收获、加速成熟、提高收获量、提高收获产品的质量和/或提高产品的营养价值、提高产品的储存稳定性和/或可加工性,这些超出了本身所期望的效果。
属于按照本发明优选进行处理的转基因植物或植物品种(即通过基因工程得到的那些)包括通过基因材料的基因工程修饰得到的所有植物,所述基因修饰赋予这些植物特别有利的有用的性能(“特性”)。这种性能的例子是较好的植物生长、增强对高或低温的耐受性、增强对旱灾或水灾或土壤盐量的耐受性、增加花卉的性能、易于收获、加速成熟、较高的收获产量、收获产品较好的质量和/或较高的营养价值、收获产品较好的储存稳定性和/或可加工性。进一步和特别强调的所述性能的例子是提高植物对动物和微生物的害虫,如昆虫、螨、植物病菌真菌、细菌和/或病毒的抵御性,以及提高植物对某些除草活性化合物的耐受性。可提及的转基因植物的例子是重要的农作物,如谷类农作物(小麦、稻)、玉米、大豆、土豆、棉花、油菜籽油菜和水果植物(水果为苹果、梨、柑橘属水果和葡萄),特别强调的是玉米、大豆、土豆、棉花和油菜籽油菜。特别强调的特性是通过在植物中产生的毒素,特别是通过来自Thuringiensis杆菌的基因物质(例如通过基因CryIA(a)、CryIA(b)、CryIA(c)、CryIIA、CryIIIA、CryIIIB2、Cry9c、Cry2Ab、Cry3Bb和CryIF及它们的联合)(下文称作“Bt植物”)在植物中产生的那些增强植物对昆虫的抵御。此外,特别强调的特性是植物对某些除草活性化合物,如咪唑啉酮类、磺酰脲类、草甘膦类或膦基麦黄酮(例如“PAT”基因)的增强的耐受性。给予所述的需要的特性的基因也可以在转基因植物中相互联合存在。可提及的“Bt植物”的例子是以商标名YIELD GARD(例如玉米、棉花、大豆)、KnockOut(例如玉米)、StarLink(例如玉米)、Bollgard(棉花)、Nucotn(棉花)和Newleaf(土豆)出售的玉米品种、棉花品种、大豆品种和土豆品种。可提及的耐受除草剂的植物是以商标名RoundupReady(耐受草甘膦,例如玉米、棉花、大豆)、Liberty Link(耐受膦基麦黄酮,例如油菜籽油菜)、IMI(耐受咪唑啉酮类)和STS(耐受磺酰脲类,例如玉米)出售的玉米品种、棉花品种、大豆品种。可提及的耐除草剂的植物(以常规方式除草剂耐受育种)包括以商标名Clearfield(例如玉米)出售的品种。当然,这些叙述也适用于具有所述特性或将来还要改良的基因特性的将来开发的植物或将来投放市场的植物品种。
所列的植物可按照本发明以特别有利的方式用本发明式(I)的化合物或活性物质混合物进行处理。上述优选的活性物质或混合物范围也适用于这些植物的处理。特别强调的是用本文中特别提及的化合物或混合物处理植物。
本发明活性物质不仅对植物害虫、卫生害虫和储藏物品中的害虫具有活性,而且在兽医领域,对防治动物寄生虫(外寄生虫)也有活性,例如硬蜱、软蜱、兽疥癣螨、虱状蒲螨、蝇(叮咬和吸食)、寄生性蝇幼虫、虱、毛虱、羽虱和跳蚤。这些寄生虫包括:
虱目,例如,血虱属、颚虱属、虱属、Phtirus spp.、管虱属;
食毛目以及钝角亚目和细角亚目,例如,毛羽虱属、Menopon spp.、巨毛虱属、羽虱属、Werneckiella spp.、Lepikentron spp.、畜虱属、嚼虱属、猫羽虱属;
双翅目以及长角亚目和短角亚目,例如,伊蚊属、按蚊属、库蚊属、蚋属、真蚋属、白蛉属、Lutzomyia spp.、库蠓属、斑虻属、瘤虻属、黄虻属、虻属、麻翅虻属、Philipomyia spp.、蜂虱蝇属.、家蝇属、齿股蝇属、螫蝇属、角蝇属、莫蝇属、厕蝇属、舌蝇属、丽蝇属、绿蝇属、金蝇属、Wohlfahrtia spp.、麻蝇属、狂蝇属、皮蝇属、胃蝇属、虱蝇属、Lipoptena spp.、蜱蝇属;
蚤目,例如,蚤属、栉首蚤属、印鼠客蚤属、角叶蚤属;
异翅亚目,例如,臭虫属、椎猎蝽属、红腹猎蝽属、全圆蝽属;
蜚蠊目,例如,东方蜚蠊、美洲大蠊、德国小蠊、蜚蠊属;
蜱螨目以及后气门亚目和中气门亚目,例如,锐缘蜱属、纯缘蜱属、残喙蜱属、硬蜱属、花蜱属、牛蜱属、革蜱属、Haemophysalis spp.、璃眼蜱属、扇头蜱属、皮刺螨属、刺利螨属、肺刺螨属、胸孔螨属、瓦螨属;
辐螨亚目(前气门亚目)和粉螨目(无气门亚目),例如,蜂跗线螨属、姬螫螨属、禽螫厘螨属、肉螨属、疮螨属、蠕形螨属、恙螨属、牦螨属、粉螨属、食酪螨属、嗜木螨属、颈下螨属、翅螨属、瘙螨属、痒螨属、耳螨属、疥螨属、痂螨属、疙螨属、胞螨属、皮膜螨属。
它们也具有例如优良的抗壁虱类例如Amblyomma hebraeum、寄生蝇类例如Lucilia cuprina和蚤类例如Ctenocephalides felis的各发育阶段的活性。
本发明的式(I)活性化合物也适用于防治侵扰农业家畜的节肢动物,所述农业家畜如牛、绵羊、山羊、马、猪、驴、骆驼、水牛、兔、鸡、火鸡、鸭、鹅、蜜蜂,其它家养动物,例如狗、猫、笼养鸟、水族馆的鱼,还有所谓的试验动物,例如田鼠、豚鼠、大鼠和小鼠。通过防治上述节肢动物,旨在减少动物死亡和减产(肉、奶、毛、皮、蛋、蜜等)的情况,因此,通过使用本发明的活性化合物可以使畜牧业管理更经济而简便。
应用于兽医领域时,本发明活性化合物可通过已知方法即经肠给药,例如以片剂、胶囊剂、饮剂、灌药剂、颗粒剂、膏剂、大丸剂、喂食方法、栓剂等形式给药;非经肠给药,例如通过注射(肌肉注射、皮下注射、静脉注射、腹膜内注射等),植入法给药;经鼻给药;经皮肤给药,例如以浸泡或药浴、喷雾、泼浇、擦、洗刷、撒粉方式给药,也可借助于含有活性化合物的成型制品,例如项圈、耳饰物、尾饰物、肢环(带)、笼头、装饰器具等给药。
当用于家畜、家禽、宠物等时,可将本发明的活性化合物作为含有1-80重量%的活性化合物的制剂形式(例如粉剂、乳剂、流动剂)直接或100-10,000倍稀释后使用,或用作药浴。
另外,发现本发明活性化合物还对损坏工业材料的昆虫具有很强的杀虫活性。
作为实例并优选列出下述昆虫,但并不限于此:
鞘翅目昆虫,如
北美家天牛、绿虎天牛(Chlorophorus pilosis)、家具窃蠹、报死材窃蠹、类翼窃蠹、Dendrobium pertinex、松芽枝窃蠹、松产品窃蠹(Priobium carpini)、褐粉蠹、粉蠹(Lyctus africanus)、南方粉蠹、栎粉蠹、粉蠹(Lyctus pubescens)、胸粉蠹(Trogoxylon aequale)、鳞毛粉蠹、材小蠹属、条木小蠹属、咖啡黑长蠹、Bostrychus capucins、褐异翅长蠹、棘长蠹属、竹竿粉长蠹。
革翅目,例如
蓝黑树蜂、云杉大树蜂、泰加大树蜂、大树蜂(Urocerus augur)
白蚁,例如
木白蚁(Kalotermes flavicollis)、麻头堆砂白蚁、印巴结构木异白蚁、欧美散白蚁、散白蚁(Reticulitermes santonensis)、散白蚁(Reticulitermes lucifugus)、达尔文澳白蚁、内华达古白蚁、台湾乳白蚁。
缨尾目,例如台湾衣鱼。
本发明意义上的工业材料可以理解为表示无生命材料,例如优选合成材料、粘合剂、胶、纸和板、皮革、木材、木制品和涂料。
木材以及木制品是特别需要优选保护使其免受昆虫侵袭的材料。
可用本发明组合物或含有本发明组合物的混合物保护的木材和木制品可以理解为表示,例如:
建筑用木材、木梁、铁路轨枕、桥梁组件、桥型码头、木制交通工具、箱子、货架、集装箱、电话线杆、木外罩、木窗和木门、胶合板、粗纸板、在房屋建筑或建筑细木工行业中常用的细木工或木制品。
本发明活性化合物可直接,或以浓缩形式或常规制剂,如粉剂、颗粒剂、溶液、悬浮剂、乳剂或糊剂方式使用。上述制剂可以已知方法制备,例如通过将活性化合物与至少一种溶剂或稀释剂、乳化剂、分散剂和/或粘合剂或固定剂、抗水剂混合,以及如需要加入催干剂和UV稳定剂以及如需要加入染料和颜料,和其它加工助剂。
用于保护木材和木制品的杀虫组合物或浓缩物中包括0.0001至95重量%,特别是0.001至60重量%浓度的本发明活性化合物。
组合物或浓缩物的使用量是根据昆虫的种类和个体密度以及介质而确定的。最佳施用量各自可在应用时通过系列试验确定。然而基于需保护的材料,通常使用0.0001至20重量%,优选0.001至10重量%的活性化合物是足够的。
适合的溶剂和/或稀释剂是有机化学溶剂或溶剂混合物和/或低挥发性的油性或油类有机化学溶剂或溶剂混合物和/或极性有机化学溶剂或溶剂混合物和/或水,任选地可加入乳化剂和/或湿润剂。
优选使用的有机化学溶剂是油性或油类溶剂,其蒸发值大于35以及闪点大于30℃,并优选大于45℃。用作上述低挥发度以及不溶于水的油性和油类溶剂物质是相应的矿物油或它们的芳族馏分,或含有矿物油的溶剂混合物,优选石油溶剂、石油和/或烷基苯。
优选使用沸程为170-220℃的矿物油、沸程为170-220℃的石油溶剂、沸程为250-350℃的锭子油、沸程为160-280℃的石油或芳烃,以及松节油等。
在一个优选实施方案中,使用沸程为180-210℃的液体脂族烃或沸程为180-220℃的芳族和脂族烃的高沸程混合物和/或锭子油和/或一氯代萘,优选α-一氯代萘。
蒸发值大于35以及闪点大于30℃并优选大于45℃的低挥发度的有机油性或油类溶剂可用易或中挥发度的有机溶剂部分替换,条件是溶剂混合物的蒸发值同样大于35以及闪点大于30℃并优选大于45℃,以及杀虫杀菌混合物可溶或可乳化于上述溶剂混合物中。
在优选实施方案中,部分有机化学溶剂或溶剂混合物被脂族极性有机化学溶剂或溶剂混合物替代。优选使用含有羟基和/或酯基和/或醚基的脂族有机溶剂,例如乙二醇醚、酯等。
本发明使用的有机化学粘合剂是合成树脂和/或粘合干性油,它们本身已知可用水稀释和/或可溶解或分散或乳化于上述使用的机化学溶剂中,特别是由下列物质组成的或包含下列物质的粘合剂丙烯酸树脂、乙烯基树脂,例如聚乙酸乙烯酯、聚酯类树脂、缩聚或加聚树脂、聚氨酯树脂、醇酸树脂或改性的醇酸树脂、酚醛树脂、烃类树脂,如茚/香豆酮树脂、有机硅树脂、干性植物油和/或干性油和/或基于天然和/或合成树脂的物理干性粘合剂。
用作粘合剂的合成树脂可以乳剂、分散剂或溶液形式使用。沥青或沥青状物质也可用作粘合剂,用量至多为10重量%。还可以使用已知的染料、颜料、防水剂、气味调节剂和抑制剂或防腐剂等。
在本发明组合物或浓缩物中优选包括作为有机化学粘合剂的至少一种醇酸树脂或改性醇酸树脂和/或干性植物油。本发明优选使用含油量大于45重量%,优选50-68重量%的醇酸树脂。
上述粘合剂可全部或部分被固定剂(混合物)或增塑剂(混合物)替代。加入这些添加剂的目的是防止活性化合物的蒸发以及结晶或沉淀。它们优选替代0.01至30%的粘合剂(以使用的粘合剂为100%计)。
增塑剂选自邻苯二甲酸酯类的化学物质,如邻苯二甲酸二丁酯、邻苯二甲酸二辛酯或邻苯二甲酸苄基丁基酯;磷酸酯类如磷酸三丁酯;己二酸酯,如二-(2-乙基己基)己二酸酯;硬脂酸酯,如硬脂酸丁酯或硬脂酸戊酯;油酸酯,如油酸丁酯;甘油醚或高分子量的乙二醇醚;甘油酯和对甲苯磺酸酯。
固定剂在化学上基于聚乙烯烷基醚,如聚乙烯基甲基醚或酮,如二苯甲酮和亚乙基二苯甲酮。
其它适用的溶剂或稀释剂特别是水,任选与一种或多种上述有机化学溶剂或稀释剂、乳化剂和分散剂混合使用。
特别有效的木材保护方法是通过大批量的浸渍方法,例如通过真空、双真空或加压方法。
任选地,直接可用的组合物可以包含其它杀虫剂和任选地也可以有一或多种杀真菌剂。
可能混合于其中的另外的组分优选是WO 94/29 268中提到的杀虫剂和杀菌剂。在上述文献中提到的化合物明确地说是本发明申请的一部分。
可以非常特别优选地混合于其中的组分是杀虫剂如毒死蜱、辛硫磷、氟硅菊酯、甲体氯氰菊酯、氟氯氰菊酯、氯氰菊酯、溴氰菊酯、氯菊酯、吡虫啉、吡虫清、氟虫脲、氟铃脲、四氟菊酯、thiacloprid、methoxyphenoxid和杀虫隆,以及杀真菌剂如氟环唑、己唑醇、戊环醇、丙环唑、戊唑醇、环唑醇、叶菌唑、抑霉唑、苯氟磺胺、甲苯氟磺胺、3-碘代-2-丙炔基-丁基氨基甲酸酯、N-辛基-异噻唑啉-3-酮和4,5-二氯-N-辛基异噻唑啉-3-酮。
同样,本发明的活性化合物可用于保护经常与海水或盐水接触的各种物品,如船体、滤器、网、船体结构、锚和信号装置免受生物附着。
由于定居性寡毛纲目,如龙介虫科以及甲壳类和Ledamorpha(茗荷儿)类,如各种茗荷属和铠茗荷属,或藤壶亚目(藤壶虫),如藤壶属或指茗荷属的附着增加了船体的摩擦阻力并由于增加了能源消耗以及此外经常滞留干船坞,这样明显增加了运营成本。
此外附着生物还有海藻,例如水云属和仙菜属,特别重要的是定居性软甲亚纲(昆甲类)的附着,该昆甲类包括在蔓足纲(蔓足类甲壳动物)中。
令人惊奇地,现已发现本发明活性化合物具有突出的防污(抗植被)作用。
单独或与其它活性物质组合使用本发明化合物时,可以不使用重金属,如,例如硫化二(三烷基锡)、月桂酸三正丁基锡、氯化三正丁基锡、氧化亚铜、氯化三乙基锡、三正丁基(2-苯基-4-氯苯氧基)-锡、氧化三丁基锡、二硫化钼、氧化锑、聚合钛酸丁酯、苯基-(联吡啶)-三氯化铋、氟化三正丁基锡、亚乙基二硫代氨基甲酸锰、二甲基二硫代氨基甲酸锌、亚乙基双硫代氨基甲酸锌、2-吡啶硫醇-1-氧化物的锌和铜盐、双二甲基二硫代氨基甲酰基亚乙基双硫代氨基甲酸锌、氧化锌、亚乙基双二硫代氨基甲酸亚铜、硫氰酸铜、环烷酸铜和卤化三丁基锡,或显著降低上述化合物浓度。
即用防污漆还可任选包含其它活性化合物,优选杀藻剂、杀菌剂、除草剂、杀软体动物剂或其它防污活性化合物。
下列组分优选用于本发明防污组合物的混合组分:
杀藻剂,如
2-叔丁基氨基-4-环丙基氨基-6-甲硫基-1,3,5-三嗪、双氯酚、敌草隆、草藻灭、醋酸三苯基锡、异丙隆、噻唑隆、乙氧氟草醚、灭藻醌和特丁净,
杀菌剂,如
苯并[b]噻吩甲酸环己基酰胺-S,S-二氧化物、抑菌灵、Fluorfolpet、3-碘-2-丙炔基丁基氨基甲酸酯、对甲抑菌灵和唑类,如戊环唑、环唑醇、氧唑菌、己唑醇、环戊唑菌、丙环唑和戊唑醇;
杀软体动物剂,如
醋酸三苯基锡、四聚乙醛、灭虫威、贝螺杀、硫双威和混杀威;
或常用防污活性化合物,如
4,5-二氯-2-辛基-4-异噻唑啉-3-酮、二碘甲基paratryl砜、2-(N,N-二甲基硫代氨基甲酰基硫基)-5-硝基噻唑基、2-吡啶硫醇-1-氧化物的钾、铜、钠和锌盐、吡啶三苯基硼烷、四丁基二锡氧烷、2,3,5,6-四氯-4-(甲磺酰基)-吡啶、2,4,5,6-四氯间苯二腈、二硫化四甲基秋兰姆和2,4,6-三氯苯基马来酰亚胺。
使用的防污组合物中包含浓度为0.001至50重量%,特别是0.01至20重量%的本发明活性物质或本发明化合物。
本发明防污组合物还包括在下述文献例如Ungerer,Chem.Ind.1985,37,730-732和Williams,Antifouling MarineCoatings,Noyes,Park Ridge,1973中公开的常用组分。
除了杀藻、杀菌、杀软体动物活性化合物和本发明的杀虫活性化合物外,防污涂料组合物中还特别包括粘合剂。
公知的粘合剂的实例包括溶剂体系中的聚氯乙烯、溶剂体系中的氯化橡胶、溶剂体系中特别是含水体系中的丙烯酸树脂、水分散体形式或有机溶剂体系形式的氯乙烯/醋酸乙烯酯共聚物体系、丁二烯/苯乙烯/丙烯腈橡胶、干性油,如亚麻子油,树脂酯或与焦油或沥青、柏油以及环氧化合物、少量的氯化橡胶、氯化聚丙烯和乙烯基树脂混合形成的改性硬树脂。
涂料中还任选可包含优选不溶于海水的无机颜料、有机颜料或染料。涂料中还可包括如松香类物质,以使活性化合物可控制地释放。此外,涂料中可以包含增塑剂,影响流变性质的改良剂,以及其它常规组分。还可以将本发明化合物或上述混合物加入自抛光防污体系中。
活性化合物还适于防治封闭空间,如公寓、厂房、办公室、车厢等空间中发生的害虫,特别是昆虫、蜘蛛和螨。它们可通过单独或与其它活性或辅助物质一起在防治上述害虫的家用杀虫剂产品中使用来防治害虫。它们对敏感和抗性种群以及所有发育阶段都有杀虫活性。这些害虫包括:
蝎目,例如钳蝎(Buthus occitanus)。
蜱螨目,例如波斯锐缘蜱、翘缘锐缘蜱、苔螨属、鸡皮刺螨、家食甜螨、非洲钝缘蜱、血红扇头蜱、恙螨(Trombicula alfreddugesi)、Neutrombicula autumnalis、屋尘螨、粉尘螨。
蛛形目,例如鸟蛤蛛科、园蛛科。
盲蛛目,例如拟蝎类(Pseudoscorpiones chelifer)、Pseudoscorpiones cheiridium、Opiliones phalangium。
等足目,例如潮虫、鼠妇。
倍足目,例如具斑马陆、山蛩虫属。
唇足目,例如地蜈蚣属。
Zygentoma目,例如栉衣鱼属、台湾衣鱼、Lepismodes inquilinus。
蜚蠊目,例如东方蜚蠊、德国小蠊、小蠊属(Blattella asahinai)、马得拉蜚蠊、角腹蠊属、木蠊属、澳洲大蠊、美洲大蠊、褐斑大蠊、黑胸大蠊、长须蜚蠊。
跳跃亚目,例如家蟀。
革翅目,例如欧洲球螋。
等翅目,例如木白蚁属、散白蚁属。
啮虫目,例如Lepinatus属、粉啮虫属。
鞘翅目,例如圆皮蠹属、毛皮蠹属、皮蠹属、长头谷蠹、隐跗郭公虫属、蛛甲属、谷蠹、谷象、米象、玉米象、药材甲。
双翅目,例如埃及伊蚊、白纹伊蚊、Aedes taeniorhynchus、按蚊属、红头丽蝇、高额麻虻、致倦库蚊、尖音库蚊、Culex tarsalis、果蝇属、夏厕蝇、家蝇、白蛉属、麻蝇(Sarcophaga carnaria)、蚋属、厩螫蝇、大蚊(Tipula paludosa)。
鳞翅目,例如小蜡螟、蜡螟、印度古斑螟、谷蛾、袋谷蛾、幕谷蛾。
蚤目,例如犬栉首蚤、猫栉首蚤指名亚种、人蚤、穿皮潜蚤、印鼠客蚤。
膜翅目,例如广布弓背蚁、亮毛蚁、黑毛蚁、Lasius umbratus、小家蚁、Paravespula属、铺道蚁。
虱目,例如头虱、体虱、阴虱。
异翅亚目,例如热带臭虫、温带臭虫、长红猎蝽、侵扰锥猎蝽。
在家用杀虫剂领域,它们可以单独使用或与其他合适的活性化合物例如磷酸酯类、氨基甲酸酯类、拟除虫菊酯类、生长调节剂或来自其他已知种类的杀虫剂的活性化合物。
它们可以如下述使用:气溶胶,非增压喷雾剂,例如泵喷雾、喷洒喷雾、烟雾发生器、浓雾、泡沫、凝胶、带有纤维素或聚合物制成的蒸发片的蒸发产品、液体蒸发器、凝胶和薄膜蒸发器、推进式蒸发器、不需能量或被动式蒸发系统、捕蛀虫纸、捕蛾袋和捕虫胶、作为颗粒剂或粉剂、在撒布饵料中或饵料位置。
本发明物质的制备和应用通过下述实施例来说明。
制备实施例
实施例1
在100℃将0.50g(1.137mmol)的4-氯-2-{2-甲基-4-[1,2,2,2-四氟-1-(三氟甲基)乙基]苯基}-1H-异吲哚-1,3(2H)-二酮和0.222g(1.251mmol)的1-{[(三甲基甲硅烷基)甲基]硫基}-2-丙胺在不存在溶剂的情况下搅拌1小时。然后通过硅胶柱色谱(流动相:二氯甲烷)纯化粗产物。
异构体1:
3-氯-N2-{2-甲基-4-[1,2,2,2-四氟-1-(三氟甲基)乙基]苯基}-N1-(1-甲基-2-{[(三甲基甲硅烷基)甲基]硫基}乙基)邻苯二甲酰胺
收率:0.12g(理论量的15%)
m.p.:159-160℃
HPLC:log P(pH2.3)=5.38
1H-NMR(CD3CN):δ=0(9H),1.15(d,3H),1.74(m,2H),2.32(s,3H),2.55(m,1H),2.65(m,1H),4.14(m,1H),6.85(m,1H),7.55(m,5H),8.05(m,1H),8.30(m,1H)ppm.
异构体2:
3-氯-N1-{2-甲基-4-[1,2,2,2-四氟-1-(三氟甲基)乙基]苯基}-N2-(1-甲基-2-{[(三甲基甲硅烷基)甲基]硫基}乙基)邻苯二甲酰胺
收率:0.20g(理论量的27%)
m.p.:161-162℃
HPLC:log P(pH2.3)=5.56
1H-NMR(CD3CN):δ=0(9H),1.15(d,3H),1.75(m,2H),2.35(s,3H),2.5(m,1H),2.65(m,1H),4.15(m,1H),6.95(m,1H),7.55(m,3H),7.65(m,1H),7.75(m,1H),8.15(m,1H),8.55(m,1H)ppm.
实施例2
将0.50g(1.29mmol)的4-氯-2-{2-甲基-4-[1,1,2,2-四氟乙氧基苯基]-1H-异吲哚-1,3(2H)-二酮和0.38g(3.65mmol)的三甲基甲硅烷基甲基胺加热回流16小时。然后减压下浓缩反应混合物,粗产物用异丙醚研制。
异构体混合物:
3-氯-N1-[2-甲基-4-(1,1,2,2-四氟乙氧基)苯基]-N2-[(三甲基甲硅烷基)甲基]邻苯二甲酰胺(异构体1)和3-氯-N2-[2-甲基-4-(1,1,2,2-四氟乙氧基)苯基]-N1-[(三甲基甲硅烷基)甲基]邻苯二甲酰胺(异构体2)
收率:0.55g(理论量的56%)
HPLC:log P(pH2.3)=3.59和3.69
1H-NMR(CD3CN):δ=0.1(9H),2.25(s,3H),2.75(s,2H),6.12(m,1H),6.7-8.5(m,8H)ppm。
实施例3
在100℃将0.80g(1.819mmol)的4-氯-2-{2-甲基-4-[1,2,2,2-四氟-1-(三氟甲基)乙基]苯基}-1H-异吲哚-1,3(2H)-二酮和0.587g(3.639mmol)的2-甲基-2-[(三甲基甲硅烷基)氧基]-1-丙胺在不存在溶剂的情况下搅拌1小时。然后通过硅胶柱色谱(流动相:二氯甲烷)纯化粗产物。
异构体1:
3-氯-N1-{2-甲基-4-[1,2,2,2-四氟-1-(三氟甲基)乙基]苯基}-N2-{2-甲基-2-[(三甲基甲硅烷基)氧基]丙基}邻苯二甲酰胺
收率:0.42g(理论量的23%)
m.p.:144-145℃
HPLC:log P(pH2.3)=3.11
1H-NMR(CD3CN):δ=0(9H),1.15(s,6H),2.3(s,3H),3.2(m,2H),6.70-8.50(m,8H).
异构体2:
3-氯-N2-{2-甲基-4-[1,2,2,2-四氟-1-(三氟甲基)乙基]苯基}-N1-{2-甲基-2-[(三甲基甲硅烷基)氧基]丙基}邻苯二甲酰胺
收率:0.27g(理论量的22%)
m.p.:163-164℃
HPLC:log P(pH2.3)=3.19
1H-NMR(CD3CN):δ=0(9H),1.1(s,3H),1.15(s,3H),2.3(s,3H),3.25(m,2H),6.95(m,1H),7.45(m,3H),7.60(m,2H),7.95(m,1H),8.35(m,1H)ppm.
下列化合物可以按照实施例1-3之一的方法获得:
No. | X | Y | -(CR1R2)a-Ab-(CR3R4)c-Si(R5R6R7) | log P(pH2.3) |
4 | 3-Cl | 2‘-Me,4‘-i-C3F7 | -CH2SiMe3 | 4.72 |
5 | 6-Cl | 2‘-Me,4‘-i-C3F7 | -CH2SiMe3 | 4.58 |
6 | 3-Cl | 2‘-Me,4‘-OCF3 | -CH2SiMe3 | |
7 | 6-Cl | 2‘-Me,4‘-OCF3 | -CH2SiMe3 | |
8 | 3-Cl | 2‘-Me,4‘-i-C3F7 | -(CH2)3-Si(OMe)3 | |
9 | 6-Cl | 2‘-Me,4‘-i-C3F7 | -(CH2)3-Si(OMe)3 | |
10 | 3-Cl | 2‘-Me,4‘-OCF3 | -(CH2)3-Si(OMe)3 | |
11 | 6-Cl | 2‘-Me,4‘-OCF3 | -(CH2)3-Si(OMe)3 | |
12 | 3-Cl | 2‘-Me,4‘-i-C3F7 | -CH(Me)-CH2-S-CH2-SiMe(OEt)2 | |
13 | 6-Cl | 2‘-Me,4‘-i-C3F7 | -CH(Me)-CH2-S-CH2-SiMe(OEt)2 | |
14 | 3-Cl | 2‘-Me,4‘-OCF3 | -CH(Me)-CH2-S-CH2-SiMe(OEt)2 | |
15 | 6-Cl | 2‘-Me,4‘-OCF3 | -CH(Me)-CH2-S-CH2-SiMe(OEt)2 |
原料的制备
将1.66g(13.8mmol)的三甲基甲硅烷基甲硫醇在0℃先加入到20ml甲醇中。滴加0.788g(13.8mmol)的2-甲基氮杂环丙烷,将混合物在0℃再搅拌4小时,然后加热回流8小时,随后减压下浓缩反应混合物。
收率:1.84g(理论量的48%)的1-{[(三甲基甲硅烷基)甲基]硫基}-2-丙胺油状物
HPLC:log P(pH2.3)=1.28
1H-NMR(CD3CN):δ=0.05(9H),1.15(d,3H),1.75(q,2H),2.50(m,2H),2.85(br,2H),3.10(m,1H)ppm.
所述的logP值通过HPLC(高效液相色谱)使用反相柱(C18)根据EECDirective 79/831 Annex V.A8测定。温度:43℃。
在酸性范围内,测定在pH2.3下进行,使用流动相0.1%磷酸水溶液和乙腈,线性梯度自10%乙腈至90%乙腈。
使用具有已知logP值(使用两个相继的链烷酮之间的线性内推法通过滞留时间测定logP值)的没有支链的链烷-2-酮(具有3-16个碳原子)进行校正。
使用200nm-400nm的UV谱在最大的色谱信号中测定λ最大值。
应用实施例
实施例A
烟芽夜蛾(Heliothis virescens)试验
溶剂:7重量份二甲基甲酰胺
乳化剂:2重量份的烷基芳基聚乙二醇醚
为制备适合的活性化合物制剂,将1重量份活性化合物与上述量的溶剂和乳化剂混合,并用含乳化剂的水稀释浓缩物至所需浓度。
将大豆嫩枝(Glycine max)通过浸入所需浓度的活性化合物制剂中进行处理,并在大豆叶仍然潮湿时放上烟芽夜蛾(Heliothisvirescens)毛虫。
一定时间后,测定杀死百分率。100%表示所有的毛虫都已经被杀死;0%表示没有毛虫被杀死。
在该试验中,例如,下列实施例化合物显示出好的活性:
表A
损害植物的昆虫
烟芽夜蛾(Heliothis virescens)试验
实施例B
猿叶甲(Phaedon)幼虫试验
溶剂:7重量份二甲基甲酰胺
乳化剂:2重量份的烷基芳基聚乙二醇醚
为了制备活性化合物合适的制剂,将1份重量的活性化合物与所述量溶剂和乳化剂混合,用含乳化剂的水将浓缩物稀释到需要的浓度。
通过浸入到期望浓度的活性化合物的制剂中来处理甘蓝叶(Brassicaoleracea),并且在叶子还湿润的时候用辣根猿叶甲(Phaedon cochleariae)幼虫侵染。
一定时间后,测定杀死百分率。100%表示所有的甲虫幼虫都已经被杀死;0%表示没有甲虫幼虫被杀死。
在该试验中,例如,下列实施例化合物显示出好的活性:
表B
损害植物的昆虫
猿叶甲(Phaedon幼虫)试验
表B
损害植物的昆虫
猿叶甲(Phaedon幼虫)试验
实施例C
菜蛾(Plutella)试验,敏感株
溶剂:7重量份二甲基甲酰胺
乳化剂:2重量份的烷基芳基聚乙二醇醚
为制备适合的活性化合物制剂,将1重量份活性化合物与上述量的溶剂和乳化剂混合,并用含乳化剂的水稀释浓缩物至所需浓度。
通过浸入到期望浓度的活性化合物的制剂中来处理甘蓝叶(Brassicaoleracea),并且在叶子还湿润的时候用小菜蛾(Plutella xylostella,敏感株)毛虫侵染。
一定时间后,测定杀死百分率。100%表示所有的毛虫都已经被杀死;0%表示没有毛虫被杀死。
在该试验中,例如,下列实施例化合物显示出好的活性:
表C
损害植物的昆虫
菜蛾(Plutella)试验,敏感株
实施例D
菜蛾(Plutella)试验,抗性株
溶剂:7重量份二甲基甲酰胺
乳化剂:2重量份的烷基芳基聚乙二醇醚
为制备适合的活性化合物制剂,将1重量份活性化合物与上述量的溶剂和乳化剂混合,并用含乳化剂的水稀释浓缩物至所需浓度。
通过浸入到期望浓度的活性化合物的制剂中来处理甘蓝叶(Brassicaoleracea),并且在叶子还湿润的时候用小菜蛾(Plutella xylostella,抗性株)毛虫侵染。
一定时间后,测定杀死百分率。100%表示所有的毛虫都已经被杀死;0%表示没有毛虫被杀死。
在该试验中,例如,下列实施例化合物显示出好的活性:
表D
损害植物的昆虫
菜蛾(Plutella)试验,抗性株
实施例E
甜菜夜蛾(Spodoptera exigua)试验
溶剂:7重量份二甲基甲酰胺
乳化剂:2重量份烷基芳基聚乙二醇醚
为了制备活性化合物合适的制剂,将1份重量的活性化合物与所述量溶剂和乳化剂混合,用含乳化剂的水将浓缩物稀释到需要的浓度。
通过浸入到期望浓度的活性化合物的制剂中来处理甘蓝叶(Brassicaoleracea),并且在叶子还湿润的时候用甜菜夜蛾(Spodoptera exigua)毛虫侵染。
一定时间后,测定杀死百分率。100%表示所有的毛虫都已经被杀死;0%表示没有毛虫被杀死。
在该试验中,例如,下列实施例化合物显示出好的活性:
表E
损害植物的昆虫
甜菜夜蛾(Spodoptera exigua)试验
实施例F
草地贪夜蛾(Spodoptera frugiperda)试验
溶剂:7重量份二甲基甲酰胺
乳化剂:2重量份烷基芳基聚乙二醇醚
为了制备活性化合物合适的制剂,将1份重量的活性化合物与所述量溶剂和乳化剂混合,用含乳化剂的水将浓缩物稀释到需要的浓度。
通过浸入到期望浓度的活性化合物的制剂中来处理甘蓝叶(Brassicaoleracea),并且在叶子还湿润的时候用草地贪夜蛾(Spodopterafrugiperda)毛虫侵染。
一定时间后,测定杀死百分率。100%表示所有的毛虫都已经被杀死;0%表示没有毛虫被杀死。
在该试验中,例如,下列实施例化合物显示出好的活性:
表F
损害植物的昆虫
草地贪夜蛾(Spodoptera frugiperda)试验
表F
损害植物的昆虫
草地贪夜蛾(Spodoptera frugiperda)试验
表F
损害植物的昆虫
草地贪夜蛾(Spodoptera frugiperda)试验
实施例G
黄瓜条叶甲(Diabrotica balteata)试验(土壤中的幼虫)
临界浓度试验/土壤昆虫-处理转基因植物
溶剂:7重量份二甲基甲酰胺
乳化剂:1重量份的烷基芳基聚乙二醇醚
为制备适合的活性化合物制剂,将1重量份活性化合物与所述量的溶剂混合,加入所述量的乳化剂,并用水稀释该浓缩物至所需浓度。
将所述活性化合物制剂浇到土壤上。对此该制剂中活性化合物的浓度不是关键的,起决定作用的只是每单位体积的土壤中活性化合物的重量,该重量用ppm(mg/l)表示。将所述土壤装到0.25 1的盆中并在20℃保存。
在配制完成后直接向各盆中放入5粒预发芽的植物品种YIELDGUARD(Monsanto Comp.,USA的商标)的玉米粒。两天后向处理过的土壤中放入相应的测试昆虫。再过7天后通过计数露出土表的玉米苗确定活性化合物的效力(1棵植物=20%活性)。
实施例H
烟芽夜蛾(Heliothis virescens)试验(转基因植物的处理)
溶剂:7重量份二甲基甲酰胺
乳化剂:1重量份的烷基芳基聚乙二醇醚
为制备适合的活性化合物制剂,将1重量份活性化合物与所述量的溶剂和所述量的乳化剂混合,并用水稀释浓缩物至所需浓度。
将植物品种Roundup Ready(Monsanto Comp.,USA的商标)的大豆嫩枝(Glycine max)通过浸入所需浓度的活性化合物制剂中进行处理,并在大豆叶仍然潮湿时放上烟芽夜蛾(Heliothis virescens)毛虫。
一定时间后,测定杀死百分率。100%表示所有的毛虫都已经被杀死;0%表示没有毛虫被杀死。
Claims (23)
1.式(I)的邻苯二甲酰胺类化合物:
其中
X表示氢、卤素、氰基、硝基、烷氧基或卤代烷氧基,
Y表示氢、卤素、氰基、硝基、烷基、卤代烷基、烷氧基、卤代烷氧基、环烷基、卤代环烷基、环烷基氧基、卤代环烷基氧基,或表示各自任选被相同或不同的选自卤素、C1-C6-烷基、C1-C6-卤代烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C1-C6-烷硫基和C1-C6-卤代烷硫基的取代基单至四取代的苯基、苯氧基、杂芳基或杂芳基氧基,
n表示1、2或3,
m表示1、2或3,
R1、R2、R3和R4彼此独立地表示氢、烷基或环烷基,
R5、R6和R7彼此独立地表示烷基或烷氧基,
A表示-S(O)d-或氧,
a表示1、2、3或4,条件是,如果a表示2、3或4,则重复单元-CR1R2-可以具有相同或不同的意义,
b表示0或1,
c表示0、1、2、3或4,条件是,如果c表示2、3或4,则重复单元-CR3R4-可以具有相同或不同的意义,
d表示0、1或2。
2.根据权利要求1的式(I)的邻苯二甲酰胺类化合物,其中
X表示氢、卤素、氰基、硝基、C1-C6-烷氧基、C1-C6-卤代烷氧基,
Y表示氢、卤素、氰基、硝基、C1-C6-烷基、C1-C6-卤代烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C3-C6-环烷基、C3-C6-卤代环烷基、C3-C6-环烷基氧基、C3-C6-卤代环烷基氧基,或表示苯基、苯氧基、杂芳基或杂芳基氧基,它们各任选被相同或不同的选自卤素、C1-C6-烷基和C1-C6-卤代烷基的取代基单至四取代,
Y还表示苯基、苯氧基、杂芳基或杂芳基氧基,它们各任选被相同或不同的选自C1-C6-烷氧基、C1-C6-卤代烷氧基、C1-C6-烷硫基和C1-C6-卤代烷硫基的取代基单至四取代,
n表示1、2或3,
m表示1、2或3,
R1、R2、R3和R4彼此独立地表示氢、C1-C6-烷基或C3-C6-环烷基,
R5、R6和R7彼此独立地表示C1-C6-烷基或C1-C6-烷氧基,
A表示-S(O)d-或氧,
a表示1、2、3或4,条件是,如果a表示2、3或4,则重复单元-CR1R2-可以具有相同或不同的意义,
b表示0或1,
c表示0、1、2、3或4,条件是,如果c表示2、3或4,则重复单元-CR3R4-可以具有相同或不同的意义,
d表示0、1或2。
3.根据权利要求2的式(I)的邻苯二甲酰胺类化合物,其中
X表示氢、卤素、氰基、硝基、C1-C6-烷氧基或C1-C6-卤代烷氧基,
Y表示氢、卤素、氰基、硝基、C1-C6-烷基、C1-C6-卤代烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C3-C6-环烷基、C3-C6-卤代环烷基、C3-C6-环烷基氧基、C3-C6-卤代环烷基氧基,或表示苯基、苯氧基、杂芳基或杂芳基氧基,它们各任选被相同或不同的选自卤素、C1-C6-烷基和C1-C6-卤代烷基的取代基单至四取代,
n、m、R1、R2、R3、R4、R5、R6、R7、A、a、b、c和d具有权利要求2中给出的含义。
4.根据权利要求1的式(I)的邻苯二甲酰胺类化合物,其中
X表示氢、氟、氯、溴、碘、氰基、硝基、C1-C4-烷氧基、具有1-9个氟、氯和/或溴原子的C1-C4-卤代烷氧基,
Y表示氢、氟、氯、溴、碘、氰基、硝基、C1-C4-烷基、具有1-9个氟、氯和/或溴原子的C1-C4-卤代烷基、C1-C4-烷氧基、具有1-9个氟、氯和/或溴原子的C1-C4-卤代烷氧基、C3-C6-环烷基,
Y还表示苯基、苯氧基、具有1-4个包括0-4个氮原子、0-2个不相邻的氧原子和/或0-2个不相邻的硫原子在内的杂原子的5-或6-元杂芳基或杂芳基氧基,它们各任选被相同或不同的选自氟、氯、溴、碘、C1-C4-烷基、具有1-9个氟、氯和/或溴原子的C1-C4-卤代烷基、C1-C4-烷氧基、具有1-9个氟、氯和/或溴原子的C1-C4-卤代烷氧基、C1-C4-烷硫基、具有1-9个氟、氯和/或溴原子的C1-C4-卤代烷硫基的取代基单至四取代,
n表示1或2,
m表示1、2或3,
R1、R2、R3和R4彼此独立地表示氢、C1-C4-烷基或C3-C6-环烷基,
R5、R6和R7彼此独立地表示C1-C3-烷基或C1-C3-烷氧基,
A表示-S(O)d-或氧,
a表示1、2或3,条件是,如果a表示2或3,则重复单元-CR1R2-可以具有相同或不同的意义,
b表示0或1,
c表示0、1、2或3,条件是,如果c表示2或3,则重复单元-CR3R4-可以具有相同或不同的意义,
d表示0、1或2。
5.根据权利要求4的式(I)的邻苯二甲酰胺类化合物,其中
X表示氢、氟、氯、溴、碘、氰基、硝基、C1-C4-烷氧基、具有1-9个氟、氯和/或溴原子的C1-C4-卤代烷氧基,
Y表示氢、氟、氯、溴、碘、氰基、硝基、C1-C4-烷基、具有1-9个氟、氯和/或溴原子的C1-C4-卤代烷基、C1-C4-烷氧基、具有1-9个氟、氯和/或溴原子的C1-C4-卤代烷氧基、C3-C6-环烷基,
n、m、R1、R2、R3、R4、R5、R6、R7、A、a、b、c和d具有权利要求4中给出的含义。
6.根据权利要求1的式(I)的邻苯二甲酰胺类化合物,其中
X表示氯、溴、碘,
Y表示甲基、乙基、正丙基、异丙基、三氟甲基、五氟乙基、正七氟丙基、异七氟丙基、三氟甲氧基或-OCF2CF2H,
Y还表示苯氧基、吡啶基氧基或四唑基,它们各被相同或不同的选自氟、氯、溴、碘、甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、-CF3、-CHF2、-CClF2、-CF2CHFCl、-CF2CH2F、-CF2CCF2、-CH2CF3-CF2CHFCF3、-CH2CF2H、-CH2CF2CF3、-CF2CF2H-CF2CHFCF3、-OCF3、-OCHF2、-OCF2CF2H的取代基单至三取代,
n表示1,
m表示2,
R1、R2、R3和R4彼此独立地表示氢、甲基或乙基,
R5、R6和R7彼此独立地表示甲基、乙基、甲氧基或乙氧基,
A表示-S(O)d-或氧,
a表示1、2或3,条件是,如果a表示2或3,则重复单元-CR1R2-可以具有相同或不同的意义,
b表示0或1,
c表示0、1或2,条件是,如果c表示2,则重复单元-CR3R4-可以具有相同或不同的意义,
d表示0、1或2。
7.根据权利要求6的式(I)的邻苯二甲酰胺类化合物,其中
Y表示甲基、乙基、正丙基、异丙基、三氟甲基、五氟乙基、正七氟丙基、异七氟丙基、三氟甲氧基或-OCF2CF2H,
X、n、m、R1、R2、R3、R4、R5、R6、R7、A、a、b、c和d具有权利要求6中给出的含义。
8.根据权利要求1的式(I)的邻苯二甲酰胺类化合物,其为式(I-a)的邻苯二甲酰胺类化合物,
式中
Y1和Y2彼此独立地表示氢、卤素、氰基、硝基、烷基、卤代烷基、烷氧基、卤代烷氧基、环烷基、卤代环烷基、环烷基氧基、卤代环烷基氧基,或表示各任选被取代的苯基、苯氧基、杂芳基或杂芳基氧基,
A表示硫、氧、SO或SO2,
b表示0或1,和
X、R1、R2、R3、R4、R5、R6、R7、a和c具有权利要求1-7任一项中给出的含义。
9.根据权利要求1的式(I)的邻苯二甲酰胺类化合物,其为式(I-b)的邻苯二甲酰胺类化合物,
式中
Y1和Y2彼此独立地表示氢、卤素、氰基、硝基、烷基、卤代烷基、烷氧基、卤代烷氧基、环烷基、卤代环烷基、环烷基氧基、卤代环烷基氧基,或表示各任选被取代的苯基、苯氧基、杂芳基或杂芳基氧基,
A表示硫、氧、SO或SO2,
b表示0或1,和
X、R1、R2、R3、R4、R5、R6、R7、a和c具有权利要求1-7任一项中给出的含义。
10.根据权利要求8的式(I-a)的邻苯二甲酰胺类化合物,其中A表示SO或SO2。
11.根据权利要求9的式(I-b)的邻苯二甲酰胺类化合物,其中A表示SO或SO2。
12.根据权利要求8的式(I-a)的邻苯二甲酰胺类化合物,其中Y1表示C1-C4-烷基,三氟甲基、五氟乙基、正七氟丙基、异七氟丙基。
13.根据权利要求9的式(I-b)的邻苯二甲酰胺类化合物,其中Y1表示C1-C4-烷基,三氟甲基、五氟乙基、正七氟丙基、异七氟丙基。
14.根据权利要求8的式(I-a)的邻苯二甲酰胺类化合物,其中Y2表示甲基。
15.根据权利要求9的式(I-b)的邻苯二甲酰胺类化合物,其中Y2表示甲基。
16.根据权利要求1-7任一项的式(I)的邻苯二甲酰胺类化合物,其中R5、R6和R7各表示甲基。
17.根据权利要求1-7任一项的式(I)的邻苯二甲酰胺类化合物,其中A表示S、SO或SO2。
18.根据权利要求1的式(I)的邻苯二甲酰胺类化合物,其选自:
3-氯-N2-{2-甲基-4-[1,2,2,2-四氟-1-(三氟甲基)乙基]苯基}-N1-(1-甲基-2-{[(三甲基甲硅烷基)甲基]硫基}乙基)邻苯二甲酰胺,
3-氯-N1-{2-甲基-4-[1,2,2,2-四氟-1-(三氟甲基)乙基]苯基}-N2-(1-甲基-2-{[(三甲基甲硅烷基)甲基]硫基}乙基)邻苯二甲酰胺,
3-氯-N1-[2-甲基-4-(1,1,2,2-四氟乙氧基)苯基]-N2-[(三甲基甲硅烷基)甲基]邻苯二甲酰胺,
3-氯-N2-[2-甲基-4-(1,1,2,2-四氟乙氧基)苯基]-N1-[(三甲基甲硅烷基)甲基]邻苯二甲酰胺,
3-氯-N1-{2-甲基-4-[1,2,2,2-四氟-1-(三氟甲基)乙基]苯基}-N2-{2-甲基-2-[(三甲基甲硅烷基)氧基]丙基}邻苯二甲酰胺,
3-氯-N2-{2-甲基-4-[1,2,2,2-四氟-1-(三氟甲基)乙基]苯基}-N1-{2-甲基-2-[(三甲基甲硅烷基)氧基]丙基}邻苯二甲酰胺。
19.制备权利要求1或2的式(I)的化合物的方法,其特征在于,使式(II)的酰亚胺与式(III)的甲硅烷基胺任选地在稀释剂存在下反应,
式中
X、Y、n和m具有权利要求1或2中给出的含义,
H2N-(CR1R2)a-Ab-(CR3R4)c-Si(R5R6R7) (III)
式中
R1、R2、R3、R4、R5、R6、R7、A、a、b和c具有权利要求1或2中的含义。
20.杀虫剂,其特征在于它们包含至少一种权利要求1或2的式(I)化合物和填充剂和/或表面活性剂。
21.权利要求1或2的式(I)化合物用于防治害虫的用途。
22.防治害虫的方法,其特征在于将权利要求1或2的式(I)化合物作用于害虫和/或它们的栖息地。
23.制备杀虫剂的方法,其特征在于将权利要求1或2的式(I)化合物与填充剂和/或表面活性剂混合。
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DE10115406A DE10115406A1 (de) | 2001-02-06 | 2001-03-29 | Phthalsäurediamide |
DE10115406.2 | 2001-03-29 | ||
PCT/EP2002/000809 WO2002062807A1 (de) | 2001-02-06 | 2002-01-25 | Phthalsäurediamide, ein verfahren zu ihrer herstellung und ihre verwendung als schädlingsbekämpfungsmittel |
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US7211270B2 (en) | 2002-10-04 | 2007-05-01 | E. I. Du Pont De Nemours And Company | Anthranilamide insecticides |
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CN1255491A (zh) * | 1998-11-30 | 2000-06-07 | 日本农药株式会社 | 邻苯二酰胺衍生物或其盐,农业园艺用杀虫剂及其使用方法 |
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