CN1073678A - 胍的衍生物 - Google Patents
胍的衍生物 Download PDFInfo
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- CN1073678A CN1073678A CN92114469A CN92114469A CN1073678A CN 1073678 A CN1073678 A CN 1073678A CN 92114469 A CN92114469 A CN 92114469A CN 92114469 A CN92114469 A CN 92114469A CN 1073678 A CN1073678 A CN 1073678A
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- 229940079593 drug Drugs 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
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- 150000002170 ethers Chemical class 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 201000003872 goiter Diseases 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- 150000005826 halohydrocarbons Chemical class 0.000 description 1
- 239000000413 hydrolysate Substances 0.000 description 1
- KQSBZNJFKWOQQK-UHFFFAOYSA-N hystazarin Natural products O=C1C2=CC=CC=C2C(=O)C2=C1C=C(O)C(O)=C2 KQSBZNJFKWOQQK-UHFFFAOYSA-N 0.000 description 1
- 230000000266 injurious effect Effects 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 239000006166 lysate Substances 0.000 description 1
- 239000004579 marble Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 229940031815 mycocide Drugs 0.000 description 1
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000012875 nonionic emulsifier Substances 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011044 quartzite Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- OARRHUQTFTUEOS-UHFFFAOYSA-N safranin Chemical compound [Cl-].C=12C=C(N)C(C)=CC2=NC2=CC(C)=C(N)C=C2[N+]=1C1=CC=CC=C1 OARRHUQTFTUEOS-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 210000004894 snout Anatomy 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
- A01N47/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
- A01N47/44—Guanidine; Derivatives thereof
-
- 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
- A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/61—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
Abstract
式(I)表示的新的胍衍生物,式中Z代表2-氯
-5-吡啶基,2-氯-5-噻唑基或3-氯-5-异唑基;
R1代表氢原子或C1-4烷基;R2代表氢原子,C1-4烷
基,C3-4炔基,C3-4链烯基或2-氯-5-吡啶甲基;R3
和R4各代表氢原子,卤原子,C1-4烷基,C3-4炔基,C3-4
链烯基,可被取代的苄基或由Z-C(R1)H-代表的基
团,式中Z和R1代表的基团与上述相同;n代表整
数的2或3;Y代表硝基或氰基及包括式(I)表示的
化合物作为活性成分的杀虫剂组合物。
Description
本发明涉及新的胍衍生物、其制备方法及其作为杀虫剂的使用。
某类胍的衍生物可用作杀虫剂业已公开(见日本公开专利申请No.10762/1988)。
现发现了以下式(Ⅰ)表示的一类新的胍衍生物
其中
Z代表2-氯-5-吡啶基,2-氯-5-噻唑基或3-氯-5-异噁唑基;R1代表氢原子或C1-4烷基;R2代表氢原子,C1-4烷基,C3-4炔基,C3-4链烯基或2-氯-5-吡啶甲基;R3和R4各代表氢原子,卤原子,C1-4烷基,C3-4炔基,C3-4链烯基,可被取代的苄基或由Z-C(R1)H-代表的一个基团(此处的Z和R所代表的基团与上述相同);n代表整数的2或3;Y代表硝基或氰基。
式(Ⅰ)表示的胍衍生物可以下述反应得到:
a)以式(Ⅱ)表示的化合物(此处Z,R1,R2和n的意义同上)与式(Ⅲ)表示的化合物(此处R3,R4和Y的意义同上)在惰性溶剂存在下进行反应。
分子式(Ⅰ)表示的新的胍衍生物表现有强力杀虫性。
令人惊奇的是,本发明中的胍衍生物要比前述从目标公开专利申请人中得知的胍衍生物具有实质上更强的杀虫活性。
本发明的胍衍生物中,用式(Ⅰ)表示,优选的化合物为:式中,Z代表2-氯-5-吡啶基或2-氯-5-噻唑基;R1代表氢原子或甲基;R2代表氢原子,甲基,烯丙基,炔丙基,或2-氯-5-吡啶甲基;R3和R4各代表氢原子或甲基;n代表整数的2或3;Y代表硝基或氰基。
特别优选的胍衍生物,用式(Ⅰ)表示,其中:Z代表2-氯-5-吡啶基或2-氯-5-噻唑基;R1代表氢原子;R2代表氢原子或甲基;R3和R4各代表氢原子;n代表整数2或3;Y代表硝基或氰基。
作为本发明中以式(Ⅰ)表示的化合物中的具体实例,我们提出下列化合物:1-{2-(6-氯-3-吡啶甲氨基)乙基}-2-硝基胍;1-{2-(6-氯-3-吡啶甲氨基)丙基}-2-硝基胍和1-{2-(2-氯-5-噻唑甲氨基)乙基}-2-硝基胍。
如果用N-(6-氯-3-吡啶甲基)-乙二胺和3-硝基-2-甲基异硫脲作原材料,则反应过程可表示为下列反应式:
方法a)中,式(Ⅱ)原料为下述式(Ⅱ)化合物,其中Z,R,R和n如前述定义,优选的化合物基于前述优选定义。
式(Ⅱ)的原料为由日本公开专利申请No.267561/1986和48680/1987所公开的那些已知的化合物,其具体实例可以是:
N-(6-氯-3-吡啶甲基)-乙二胺,
N-(6-氯-3-吡啶甲基)-丙二胺,和
N-(2-氯-5-噻唑)-乙二胺,
方法a)中,原料为下述式(Ⅲ)化合物,其中R,R和Y如前述定义,优选的化合物基于前述优选定义。
式(Ⅲ)表示的是有机化学界众所周知的那类化合物,其具体实例是:
3-硝基-2-甲基异硫脲,和
3-氰基-2-甲基异硫脲。
在进行上述方法a)的反应时,可用任何惰性溶剂作为合适的稀释剂。
这类稀释剂的例子包括:水;脂肪族、环脂族和芳香族的及任意氯化的烃,如戊烷,己烷,环己烷,石油醚,轻石油,苯,甲苯,二甲苯,二氯甲烷,氯仿,四氯化碳,氯乙烯,氯苯,二氯苯等等;醚类,如乙醚,甲乙醚,二异丙醚,二丁醚,氧化丙烯,二甲氧基乙烷(DME),二噁烷,四氢呋喃(THF),等等;腈类,如乙腈,丙腈,丙烯腈等等;醇类,如甲醇,乙醇,异丙醇,丁醇,乙二醇等等;酯类,如乙酸乙酯,乙酸戊酯等等;酰胺类,如二甲基甲酰胺(DMF),二乙基乙酰胺(DMA),N-甲基吡咯烷酮,1,3-二甲基-2-咪唑啉酮,六甲基磷酰胺(HMPA)等等;砜和亚砜类,如二甲基亚砜(DMSO),环丁砜等等,以及碱,举例说,如吡啶。
上述方法a)中,反应温度可在很大范围内变动。一般说来,反应可在-20℃~100℃的温度下进行,优选的温度为10℃~80℃。
而且,反应是在正常的压力下进行的,虽然在较高或减压下也能进行反应。
当按本发明进行上述方法a)的反应时,按每1摩尔上述化合物(Ⅱ)加1.0~1.5摩尔的上述化合物(Ⅲ)(推荐用量1.0~1.1摩尔),任意地在有惰性溶剂,例如水存在时进行反应,即可得到如式(Ⅰ)表示的所希望的化合物。
植物对式(Ⅰ)表示的化合物有很好的耐受性,其对温血动物的毒性很低,可用于防治节肢动物害虫,特别是农林害虫、仓储物害虫和卫生害虫。这类化合物对防治敏感的和具有抗性的害虫都有交,并对所有各虫期或某几个虫期都是有效的。上述害虫包括:
等足目(甲壳纲)的无鞍潮虫,平甲虫和粗皮鼠妇;
倍足亚纲的马陆;
唇足亚纲的食果地蜈蚣和蚰蜒;
综合纲的无斑么蚰;
缨尾目的衣鱼;
革翅目的欧洲球螋;
等翅目的白蚁;
虱目的葡萄根瘤蚜,瘿绵蚜,人体虱,血虱和毛虱;
食毛目的嚼虱和畜虱;
缨翅目的温室纹蓟马和烟蓟马;
半翅目异翅亚目的扁盾蝽,间型棉红蝽,方背皮蝽,温带臭虫,长红猎蝽和锥猎蝽;
同翅目的甘蓝粉虱,木薯粉虱,温室粉虱,棉蚜,莱蚜,茶藨隐瘤蚜,甜菜蚜,波氏袋蚜,苹果绵蚜,梅大尾蚜,麦长管蚜,瘤蚜,忽布疣蚜,禾谷缢管蚜,小缘叶蝉,双叶叶蝉,黑尾叶蝉,水木坚蚧,乌盔蚧,灰飞虱,褐飞虱,红肾园盾蚧,常春藤园盾蚧,粉蚧和木虱;
鳞翅目的棉红蛉虫,松尺蠖,苹细蛾,苹果巢蛾,菜蛾,黄褐天幕毛虫,黄毒蛾,毒蛾,棉潜蛾,桔潜蛾,地老虎,切根虫,夜蛾,埃及金刚钻,实夜蛾,甜菜夜蛾,甘蓝夜蛾,松夜蛾,斜纹夜蛾,夜蛾,粉纹夜蛾,苹果小卷蛾,菜粉蛾,禾草螟,玉米螟,地中海粉斑螟,大蜡螟,果黄卷蛾,网状烟卷蛾,枞色卷蛾,茶长卷蛾和栎绿卷蛾;
鞘翅目的家具窃蠹,谷蠹,菜豆象,北美家天牛,杨树萤叶甲,马铃薯叶甲,辣根猿叶甲,叶甲,油菜金头跳甲,墨西哥大豆瓢虫,隐食甲,锯谷盗,花象,谷象,黑葡萄耳象,香蕉根颈象,白菜籽龟象,柴苜蓿叶象,皮蠹,斑皮蠹,园皮蠹,粉蠹,油菜花露尾甲,蛛甲,黄蛛甲,裸蛛甲,拟谷盗,黄粉虫,叩头虫,宽胸叩头虫,鳃角金龟子,六月金龟子和褐新西兰肋翅鳃角金龟子;
膜翅目的锯角叶蜂,叶蜂,蚁类,法老蚁和胡蜂;
双翅目的伊蚊,按蚊,库蚊,黑尾果蝇,家蝇,厕蝇,红头丽蝇,绿蝇,金蝇,疽蝇,胃蝇,厩螫蝇,狂蝇,皮蝇,虻,花毛蚊,瑞曲麦扦蝇,草种蝇,甜菜泉蝇,地中海蜡实蝇,橄榄大实蝇和欧洲大蚊。
这类有活性的化合物可以转换成通常的制剂,如溶液,乳剂,可湿性粉剂,悬浮剂,粉剂,发泡剂,膏剂,颗粒剂,气溶胶,用该活性化合浸泡天然的和合成的材料,用多聚物制成微胶囊,用作种子的表面涂层组合物,用于燃烧设备(如熏蒸筒,熏蒸罐和熏蒸管)可使用的制剂,以及超低容量(ULV)冷雾和热雾制剂。
这些制剂可用已知的方法产生,例如将有活性的化合物与增量剂,即液体的或液化的气态或固态稀释剂或载体混合,并任意地混以表面活性剂,即乳化剂和/或分散剂和/或发泡剂。在用水作增量剂时,也可用有机溶剂作为辅助溶剂。
作为液态溶剂的稀释剂或载体,主要有相应的芳香烃,如二甲苯,甲苯或烷基萘,氯化芳香烃或氯代脂肪烃,如氯代苯,氯乙烯,二氯甲烷,脂肪烃,如环己烷或链式烷烃,后者如矿物油的裂解物;醇类,如丁醇或乙二醇及醚和酯;酮类,如丙酮,甲·乙酮,甲基异丁酮或环己酮;或具有强极性的溶剂,如二甲替甲酰胺和二甲基亚砜,以及水。
说到液化的气体稀释剂或载体,即指在正常的温度和压力下为气态的液体,例如气溶胶推进剂,如卤代烃以及丁烷,丙烷,氮气和二氧化碳。
作为固态载体,可用磨碎的天然矿物,如高岭山,粘土,滑石,白垩,石英石,硅胶铝铁矿石,蒙脱石或硅藻土;研碎的合成矿物,如具有高度分散性的硅酸,氧化铝和硅酸盐。作为颗粒性固态载体,可用碾碎和裂解的天然岩石,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状颗粒,和有机物如锯末,椰子壳,玉米穗和烟草杆的颗粒。
作为乳化剂和/或发泡剂,可用非离子和阴离子乳化剂剂,如聚氧乙烯脂肪酸酯,聚氧乙烯脂肪醇醚,如烷芳基聚乙醇醚,烷基磺酸盐,烷基硫酸盐,芳基磺酸盐以及白蛋白的水解产物。
分散剂包括木质素亚硫酸盐废液和甲基纤维素。
配方中可用如下粘合剂:羧甲基纤维素和天然的及合成的多聚物(粉、颗粒、晶粒)如阿拉伯树脂胶,聚乙烯醇和聚乙酸乙烯酯。
可用着色剂,如无机色素,举例说像氧化铁,氧化钛和普鲁士兰,有机染料如茜素染料,偶氮染料或金属酞花青染料;以及微量营养物如铁盐,锰硼盐,铜盐,钻盐,铜盐和锌盐。
配方有效成分含量一般可为0.1-95%(重量),以0.5-90%(重量比)较为合适。
本发明的活性化合物可制成商业上常用的剂型,用这类剂型与其它有效化合物(如杀虫剂,毒铒,消毒剂,杀螨剂,杀线虫剂,杀真菌剂,生长调节剂或除草剂)混配可制成应用制剂。杀虫剂包括磷酸酯,氨基甲酸酯类,羧酸酯,氯代烃,苯脲及微生物的产物。
本发明的活性化合物还可进一步与增效剂混配制成商业剂型。增效剂是这样一类化合物,它们增加有效成分的活性,但就活性化合物的活性本身而言,并非必需添加增效剂。
按商业上常用剂型制得的应用制剂中,活性化合物含量可在很大的范围内变动。实用制剂中的活性化合物的浓度可为0.0000001-100%(重量比),以0.0001-1%(重量比)较为合适。
本化合物以适合于实用剂型的常规方法来使用。
当防治卫生害虫和仓储害虫时,本发明的活性化合物在木质和泥土的表面上具有非常好的持效性,施用在石灰涂刷过的表面上时,对碱有良好的稳定性。
本发明的有效化合物的制备和使用可见下述实施例。
实施例1:
将3.7克N-(6-氯-3-吡啶甲基)乙二胺,2.7克3-硝基-2-甲基异硫脲与20ml乙醇混合物在30℃下搅拌,直到不再产生甲基硫醇。冷却后过滤取出分离的结晶,即得到所希望的1-{2-(6-氯-3-吡啶甲氨基)乙基}-2-硝基胍。(mp119-122℃)
同上述同样方法可得到表1中所列的许多化合物,该表中也列出了用前面提到的方法制取的化合物。
生物测定实例:
实施例2
生测用试虫为对有机磷类和氨基甲酸酯类杀虫剂表现有抗性的黑尾叶蝉(Nephotettix cincticeps)。
测试用制剂的制备:
溶剂:以重量计3份二甲苯
乳化剂:以重量计1份聚氧乙烯-烷代苯基醚
为制备适当的有效化合物的制剂,将1份(按重量计)各活性化合物与含有上述量乳化剂的上述量的溶剂混合,将混合物用水稀释到予定浓度。
试验方法:
取数个直径为12cm的罐子,每个罐内载有高约10cm的稻秧。
每罐稻秧上喷洒10ml按上述方法制备的、并稀释到予定浓度的该活性化合物的水溶液。待喷洒的水溶液干后,每个罐上罩一个直径为7cm高14cm的金属网,内放30头对有机磷类和氨基甲酸酯类杀虫剂有抗性的雌性黑尾叶蝉成虫,然后将各罐放入恒温室内。两天后计数死虫数并算出试虫的死亡率。
实施例3
同对有机磷类和氨基甲酸酯类表现有抗性的褐飞虱做的测试
试验方法
取数个直径为12cm的罐子,每个罐内栽有侏高约10cm的稻秧。
每罐稻秧上有喷洒10ml按上述实施例2的类似方法配制的、并稀释到予定浓度的该活性化合物的水溶液。待喷洒的水溶液干后,每个罐上罩一个直径7cm,高14cm的金属网,内放30头对有机磷类和氨基甲酸酯类杀虫剂有抗性的雌性褐飞虱(Nilaparvata lugens)成虫,然后将各罐放入恒温室内。两天后计数死虫数并算出试虫的死亡率。
用上述相同的方法,测定了对有机磷类杀虫剂有抗性的白背飞虱(Sogatella furcifera)和灰飞虱(Laodelphax striatellus)对该活性化合物的死亡率。
上述生测实施例2和实施例3中,作为式(Ⅰ)表示化合物的代表性实例,表1的1、2、3号化合物,对所试害虫匀表现了有效的防治作用,例如,剂量为200ppm时,试虫的死亡率为100%。
Claims (8)
1、式(I)表示的胍衍生物
式中
Z代表2-氯-5-吡啶基,2-氯-5-噻唑基
或3-氯-5-异噁唑基;
R1代表氢原子或C1-4烷基;
R2代表氢原子,C1-4烷基,C3-4炔基,C3-4链烯基或2-氯-5-吡啶甲基;
R3代表氢原子,卤原子,C1-4烷基,C3-4炔基,C3-4链烯基,可被取代的苄基或由Z-C(R1)H-代表的基团,式中Z和R1代表的基团与上述相同;
R4代表氢原子,卤原子,C1-4烷基,C3-4炔基,C3-4链烯基,可被取代的苄基或由Z-C(R1)H-代表的基团,式中Z和R1代表的基团与上述相同;
n代表整数的2或3;
Y代表硝基或氰基。
2、权利要求1的化合物,其中
Z代表2-氯-5-吡啶基或2-氯-5-噻唑基;
R1代表氢原子或甲基;
R2代表氢原子,甲基,烯丙基,炔丙基或2-氯-5-吡啶甲基;
R3代表氢原子或甲基;
R4代表氢原子或甲基;
n代表整数的2或3;
Y代表硝基或氰基。
3、权利要求1的化合物,其中
Z代表2-氯-5-吡啶基或2-氯-5-噻唑基;
R1代表氢原子;
R2代表氢原子或甲基;
R3代表氢原子;
R4代表氢原子;
n代表整数的2或3;
Y代表硝基或氰基。
5、杀虫剂组合物,其特征在于它们含有至少一种式(Ⅰ)表示的胍衍生物。
6、防治害虫的方法,其特征在于,式(Ⅰ)表示的胍衍生物作用于昆虫和/或其栖息场所。
7、式(Ⅰ)所表示的胍衍生物用于防治害虫。
8、制备杀虫剂组合物的方法,其特征在于,将式(Ⅰ)表示的胍衍生物与增量剂和/或表面活性剂相混合。
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JP3352861A JP3059559B2 (ja) | 1991-12-17 | 1991-12-17 | 殺虫性グアニジン誘導体 |
JP352861/91 | 1991-12-17 |
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CN1073678A true CN1073678A (zh) | 1993-06-30 |
CN1037737C CN1037737C (zh) | 1998-03-18 |
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EP (1) | EP0547451B1 (zh) |
JP (1) | JP3059559B2 (zh) |
KR (1) | KR100229178B1 (zh) |
CN (1) | CN1037737C (zh) |
BR (1) | BR9205027A (zh) |
DE (1) | DE69217864T2 (zh) |
ES (1) | ES2097856T3 (zh) |
HU (2) | HU217236B (zh) |
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US6465016B2 (en) | 1996-08-22 | 2002-10-15 | Research Triangle Pharmaceuticals | Cyclosporiine particles |
US7255877B2 (en) * | 1996-08-22 | 2007-08-14 | Jagotec Ag | Fenofibrate microparticles |
EP1079808B1 (en) | 1998-05-29 | 2004-02-11 | Skyepharma Canada Inc. | Thermoprotected microparticle compositions and process for terminal steam sterilization thereof |
CN1287769C (zh) | 1998-11-20 | 2006-12-06 | 斯凯伊药品加拿大公司 | 可分散的磷脂稳定的微粒 |
ES2241663T3 (es) * | 1999-09-21 | 2005-11-01 | Skyepharma Canada Inc. | Composiciones particuladas modificadas superficialmente de substancias biologicamente activas. |
EP1689231A4 (en) | 2003-12-04 | 2007-11-14 | Bayer Cropscience Ag | INSECTICIDES N- (HETEROARYL ALKYL) ALKANDIAMINE DERIVATIVES |
MX2007004864A (es) * | 2004-10-28 | 2007-05-09 | Bayer Cropscience Ag | Derivados de n,n-di(heteroarilalquil)amina insecticidas. |
CN102792963A (zh) * | 2012-09-06 | 2012-11-28 | 中国农业大学 | 一种含戊吡虫胍和噻嗪酮的杀虫组合物 |
CN102939984B (zh) * | 2012-11-29 | 2014-02-26 | 合肥星宇化学有限责任公司 | 一种戊吡虫胍和茚虫威复配杀虫组合物及其制剂和应用 |
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JPH03200768A (ja) * | 1989-10-24 | 1991-09-02 | Agro Kanesho Co Ltd | ニトログアニジン化合物及び殺虫剤 |
KR100304157B1 (ko) * | 1993-08-05 | 2001-11-22 | 시바타 미노루 | 자기기록매체 |
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1991
- 1991-12-17 JP JP3352861A patent/JP3059559B2/ja not_active Expired - Lifetime
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- 1992-11-18 TW TW081109208A patent/TW230743B/zh active
- 1992-12-02 MX MX9206935A patent/MX9206935A/es not_active IP Right Cessation
- 1992-12-04 DE DE69217864T patent/DE69217864T2/de not_active Expired - Fee Related
- 1992-12-04 EP EP92120735A patent/EP0547451B1/en not_active Expired - Lifetime
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US5304564A (en) | 1994-04-19 |
KR100229178B1 (ko) | 1999-11-01 |
TW230743B (zh) | 1994-09-21 |
ES2097856T3 (es) | 1997-04-16 |
JP3059559B2 (ja) | 2000-07-04 |
EP0547451A1 (en) | 1993-06-23 |
US5472971A (en) | 1995-12-05 |
ZA929716B (en) | 1993-06-14 |
EP0547451B1 (en) | 1997-03-05 |
BR9205027A (pt) | 1993-06-22 |
DE69217864D1 (de) | 1997-04-10 |
HU9203996D0 (en) | 1993-03-29 |
JPH05163242A (ja) | 1993-06-29 |
MX9206935A (es) | 1993-06-30 |
CN1037737C (zh) | 1998-03-18 |
HU217236B (hu) | 1999-12-28 |
DE69217864T2 (de) | 1997-06-12 |
HUT63306A (en) | 1993-08-30 |
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