CN87106674A - 苯甲酰脲化合物和其制备方法以及含有该化合物的农药 - Google Patents
苯甲酰脲化合物和其制备方法以及含有该化合物的农药 Download PDFInfo
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- CN87106674A CN87106674A CN87106674.2A CN87106674A CN87106674A CN 87106674 A CN87106674 A CN 87106674A CN 87106674 A CN87106674 A CN 87106674A CN 87106674 A CN87106674 A CN 87106674A
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- China
- Prior art keywords
- chloro
- methylurea
- compound
- benzoyl
- trifluoromethyl
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- 238000000034 method Methods 0.000 title claims description 19
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- 125000000217 alkyl group Chemical group 0.000 claims abstract description 29
- 125000005843 halogen group Chemical group 0.000 claims abstract description 21
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
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- 230000031902 chemoattractant activity Effects 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- UOAMTSKGCBMZTC-UHFFFAOYSA-N dicofol Chemical compound C=1C=C(Cl)C=CC=1C(C(Cl)(Cl)Cl)(O)C1=CC=C(Cl)C=C1 UOAMTSKGCBMZTC-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 235000011167 hydrochloric acid Nutrition 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- 229930014550 juvenile hormone Natural products 0.000 description 1
- 239000002949 juvenile hormone Substances 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000000974 larvacidal effect Effects 0.000 description 1
- 239000002267 larvicidal agent Substances 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 239000003986 organophosphate insecticide Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical compound O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 description 1
- CTYRPMDGLDAWRQ-UHFFFAOYSA-N phenyl hydrogen sulfate Polymers OS(=O)(=O)OC1=CC=CC=C1 CTYRPMDGLDAWRQ-UHFFFAOYSA-N 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 235000015136 pumpkin Nutrition 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000020183 skimmed milk Nutrition 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Substances 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
- 239000002562 thickening agent Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 235000015099 wheat brans Nutrition 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
- C07D213/643—2-Phenoxypyridines; 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
- 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
- A01N47/08—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 one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
-
- 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
- A01N47/08—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 one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
-
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/46—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylureas
- C07C275/48—Y being a hydrogen or a carbon atom
- C07C275/54—Y being a carbon atom of a six-membered aromatic ring, e.g. benzoylureas
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- 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
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- 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
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
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- 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
- C07D213/72—Nitrogen atoms
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- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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Abstract
一种分子式如摘要附图所示的苯甲酰脲化合物 或其盐,式中X1和X2各自是氢原子、卤素原子或甲 基(但X1和X2不能同时是氢原子);Y可以是氢原 子、卤素原子、烷基,-CO2R1或-OR1等(其中R1是 氢原子、阳离子或烷基);A1是=N-或 W是氧 原子、硫原子或 K是1至3的整数,1是0或 1;而Ar是 (Z)m,其中Z可以是氢原子、卤素 原子、烷基、烷氧基、硝基或氰基等;A2是-S-, 或 而m是1至3的整数。
Description
本发明涉及新颖的苯甲酰脲化合物及其制备方法,以及含有该化合物的农药。
从美国专利3,748,356、4,173,637、4,310,530和4,005,223等文献中业已获知苯甲酰脲化合物是有效的杀虫剂。而且从美国专利,3,748,356、4,607,044和4,659,736、日本未审查专利公布号184151/1984和106069/1987,PCT(JP)公布号501418/1987和“J.Agr.Food Chem.,Vol.21.NO.3.348-354(1973)”等文献中可以看出,脲部分中与芳环相连结的氮原子上的氢原子被烷基所取代的这类苯甲酰脲化合物的衍生物也已为人们所知。此外,上述氮原子上的氢原子被烷基取代,而上述芳环上氢原子被其他芳环取代的特定苯甲酰脲化合物亦概括在上述出版物所揭示的通式中。然而,这些出版物并未对这类特定的苯甲酰脲化合物进行具体的揭示。
本发明系基于下述发现:亦即在这类特定的苯甲酰脲化合物中,其中脲部分中与芳环结合的氮原子上氢被甲基取代,与苯甲酰基相结合的另一氮原子带有一个氢原子,而所说的芳环包含一个作为取代基的芳环的这类化合物对有益的水生甲壳纲非常安全,易于在土壤中分解,其杀虫活性与这些在脲部分中与芳环相结合的氮原子上的氢未被甲基取代(带有一个氢原子)的相应化合物相同或较之更优。
因此,本发明提供了一种分子式为
的苯甲酰脲化合物或其盐,式中X1和X2各自为氢原子、卤素原子或甲基,但X1和X2不能同时为氢原子;Y可以是氢原子、卤素原子、烷基(其中所说烷基上的氢可以被卤素取代)、-CO2R1基或-OR1基,R1可以是氢原子、阳离子或烷基;A1是=N-或
(其中Y的定义如上所述);W是氧原子、硫原子或
(其中R1的定义如上所述);K是1至3的整数;1是0或1;而Ar是
,其中Z可以是氢原子、卤素原子、烷基或(氢原子)被卤素取代的烷基、烷氧基或(氢原子)被卤素取代的烷氧基、硝基、氰基或-S(O)nR2,其中R2是烷基,或被卤素取代的烷基;n是0、1或2;A2是-S-、
或
(其中Z的定义与上述相同);而m是1至3的整数。
而且,本发明提供了一种制备分子式Ⅰ之化合物的方法;一种含有分子式Ⅰ之化合物的农药;以及用于制备分子式Ⅰ之化合物的中间体。
以下将参照较佳实施例对本发明进行详细描述。
在分子式Ⅰ中,所说的烷基或被卤素取代的烷基、烷氧基或被卤素取代的烷氧基中的烷基部分可以是具有1至6个碳原子的烷基,如甲基、乙基、正丙基、异丙基、正丁基、异丁基或仲丁基,其中以甲基或乙基为佳,尤以甲基为更佳。卤素原子或包含在烷基或烷氧基(可以是被卤素取代的烷基或烷氧基)中的卤素包括氟原子、氯原子、溴原子和碘原子,但最好是氟原子、氯原子或溴原子。被卤素取代的烷基或烷氧基可以包含一个或一个以上的卤素原子。若它包含二个或二个以上卤素原子时,则这些卤素原子可以是相同或不同的。
分子式Ⅰ之苯甲酰脲化合物的盐是一种在脲部分的氮原子处形成的盐,也可以是具有碱金属原子的盐。
在分子式Ⅰ之化合物中,以(W)1位于相对于脲部分连接位置的间位或对位,特别是对位,而且(W)1在A的邻位与Ar相连接的化合物为佳。最佳化合物可以是以下式表示的化合物或其盐:
式中X1、X2、Y、A1、W、k、l、Z、A2和m的定义均与上述相同
X1和X2各自最好是氢原子或卤素原子,但至少其中一个是卤素原子;Y宜为氢原子、卤素原子、烷基或被卤素取代的烷基、或者-CO2R1基(其中R1的定义与上述相同);A1最好是
(其中Y的定义与上述相同);Z宜为氢原子、卤素原子、三氟甲基、三氟甲氧基或-S(O)nCF3基(其中n的定义与上述相同);而A2最好是
。
以下列出具体的较佳化合物:
N-[3,5-二氯-4-(3-氯-5-三氟甲基-2-吡啶氧基)苯基]-N′-(2,6-二氟苯甲酰基)-N-甲脲;
N-[4-(3-氯-5-三氟甲基-2-吡啶氧基)-2,3-二氟苯基]-N′-(2,6-二氟苯甲酰基)-N-甲脲;
N-[3-氯-4-(3-氯-5-三氟甲基-2-吡啶氧基)-苯基]-N′-(2,6-二氟苯甲酰基)-N-甲脲;
N-[4-(3-氯-5-三氟甲基-2-吡啶氧基)-2,5-二甲基苯基]-N′-(2,6-二氟苯甲酰基)-N-甲脲;
N-[3-氯-4-(3-氯-5-三氟甲基-2-吡啶氧基)-2-氟苯基]-N′-(2,6-二氟苯甲酰基)-N-甲脲;
N-[4-(3-氯-5-三氟甲基-2-吡啶氧基)苯基]-N′-(2-氯苯甲酰基)-N-甲脲;
N-[4-(2-氯-4-三氟甲基苯氧基)-2,3-二氟苯基]-N′-(2,6-二氟苯甲酰基)-N-甲脲;
N-[3-氯-4-(2-氯-4-三氟甲基苯氧基)苯基]-N′-(2,6-二氟苯甲酰基)-N-甲脲;
N-[3-氯-4-(2-氯-4-三氟甲基苯氧基)-2-氟苯基]-N′-(2,6-二氟苯甲酰基)-N-甲脲;
N-[4-(2-氯-4-三氟甲基苯氧基)苯基]-N′-(2,6-二氟苯甲酰基)-N-甲脲;
N-[3-氯-4-(2-氯-4-三氟甲基苯氧基)苯基]-N′-(2-氯苯甲酰基)-N-甲脲;
N-[4-(3-氯-5-三氟甲基-2-吡啶氧基)-2-甲基苯基]-N′-(2,6-二氟苯甲酰基)-N-甲脲;
N-{4-(3-氯-5-三氟甲基-2-吡啶氧基)-3-氟苯基}-N′-(2,6-二氟苯甲酰基)-N-甲脲;
N-{4-[2-氯-4-三氟甲基苯氧基]-3-氟苯基}-N′-(2,6-二氟苯甲酰基)-N-甲脲;
N-{4-(2-氯-4-三氟甲苯基氧基)-3,5-二氟苯基}-N′-(2,6-二氟苯甲酰基)-N-甲脲;
N-{4-(2-氯-4-三氟甲基苯氧基)-3-甲基苯基}-N′-(2,6-二氟苯甲酰基)-N-甲脲;
N-{4-(3-氯-5-三氟甲基-2-吡啶氧基)-3-甲基苯基}-N′-(2-氯代苯甲酰基)-N-甲脲;
N-[4′-氯-2-氟-4-联苯基)-N′-(2,6-二氟苯甲酰基)-N-甲脲;
N-(4′-溴-4-联苯基)-N′-(2,6-二氟苯甲酰基)-N-甲脲;
N-(2,5-二氟-4′-氯-4-联苯基)-N′-(2,6-二氟苯甲酰基)-N-甲脲;
N-(2-三氟甲基-4′-氯-4-联苯基)-N′-(2,6-二氟苯甲酰基)-N-甲脲;
N-(2,5-二氟-3′-三氟甲硫基-4-联苯基)-N′-(2,6-二氟苯甲酰基)-N-甲脲;
本发明的分子式Ⅰ之苯甲酰脲化合物可由下述所列举的方法制备
式中,X1、X2、Y、k、A1、W、l和Ar的定义与上述相同。
必要时,上述反应可在溶剂中进行。这类溶剂可列举如下:诸如苯、甲苯、二甲苯或氯苯之类的芳烃;诸如己烷或环己烷之类的环状或非环状的脂族烃;诸如二乙醚、二噁烷或四氢呋喃之类的醚;诸如乙腈或丙腈之类的腈;或者诸如二甲基甲酰胺、二甲基亚砜、四氢噻吩砜或六甲基磷酸三酰胺。
分子式Ⅲ之起始化合物可由以下所列举的方法制备:
式中,Y、k、A1、W、l和Ar的定义均与上述相同。
在分子式Ⅲ的化合物中,l为1的化合物可由以下列举的方法制备:
上式中,Hal是卤原子,而Y、K、A1、W和Ar的定义均与上述相同。
用于制备分子式Ⅲ和Ⅲ′之起始化合物的各种反应的反应条件,如反应温度、反应时间、溶剂(若需使用)和碱可适当地选自这类反应通常所用的反应条件。
方法[A]的分子式
以下将描述本发明化合物之中间体制备方法的具体例子。
中间体制备例1
4′-溴代-4-甲基氨基联苯的制备
[Ⅰ]将0.75克4-氨基-4′-溴代联苯溶于10毫升吡啶中,所得的溶液用冰冷却,并滴加1.0克乙酰氯。对上述混合液搅拌30分钟。反应完毕后,用乙酸乙酯和水萃取反应液。有机层先后用稀盐酸和饱和氯化钠水溶液洗涤后,用无水硫酸钠干燥。接着在减压下蒸出溶剂,由此得到0.8克N-(4′-溴代-4-联苯基)乙酰胺无色晶体。
[Ⅱ]将步骤[Ⅰ]所得的0.80克N-(4′-溴代-4-联苯基)乙酰胺溶于10毫升二甲基甲酰胺中,在15-20℃温度,将所制备的溶液滴加到由0.17克氢化钠(60%液体石腊混合物)和10毫升二甲基亚砜所组成的悬浮液中。滴加完毕后,将此混合液在室温下搅拌30分钟,然后在15-20℃温度下,滴加0.78克甲基碘。接着在室温下继续搅拌3小时。
反应完毕后,用乙酸乙酯和水萃取反应液。有机层用饱和氯化钠水溶液洗涤后,用无水硫酸钠干燥。然后在减压下蒸出溶剂,由此得到0.76克N-(4′-溴代-4-联苯基)-N-甲基乙酰胺无色晶体。
[Ⅲ]将步骤[Ⅱ]所得到的0.74克N-(4′-溴代-4-联苯基)-N-甲基乙酰胺溶于20毫升甲醇中,然后加入10毫升浓盐酸,并使此混合液回流加热18小时。
反应完毕后,使反应液冷却,然后倾入至100毫升10%氢氧化钾水溶液中。接着用二氯甲烷萃取。有机层先后用水和饱和氯化钠水溶液洗涤后,用无水硫酸钠干燥。此后在减压下蒸出溶剂,残留物用硅胶色谱法(展开溶剂∶正己烷/乙酸乙酯=4/1)提纯,最终得到0.3克4′-溴基-4-甲基氨基联苯,产物的熔点为127-129℃。
中间体制备例2
4-(3-氯-5-三氟甲基-2-吡啶氧基)-3-氟(N-甲基)苯胺的制备
按中间体制备例1中步骤[Ⅰ]、[Ⅱ]和[Ⅲ]中所述的相同方法,由4-氨基-2-氟苯甲醚制备0.8克4-(N-甲基)氨基-2-氟苯酚,然后将其与1.2克2,3-二氯-5-三氟甲基吡啶和0.9克无水碳酸钾一起溶于20毫升二甲基亚砜中,并在100℃和氯气流中反应1.5小时。
反应完毕后,将反应液倾入冰水中,然后用乙醚萃取。有机层先后用水和饱和氯化钠水溶液洗涤,然后用无水硫酸钠干燥。接着在减压下蒸出乙醚,残留物用硅胶色谱法提纯(展开溶剂∶正己烷/乙酸乙酯=3/2),由此得到0.5克4-(3-氯-5-三氟甲基-2-吡啶氧基)-3-氟(N-甲基)苯胺。
中间制备例3
4-(2氯-4-三氟甲基-苯氧基-氟代(N-甲基)苯胺的制备
[Ⅰ]将10克4-硝基-2-氟苯甲醚溶于150毫升1,4-二恶烷中,然后加入2克5%钯碳,并使此混合液在室温和4公斤/厘米的氢气压力下进行30分钟的催化还原反应。反应完毕后,通过过滤除去钯碳,接着在减压下蒸出溶剂,由此得到8.6克4-氨基-2-氟苯甲醚。
[Ⅱ]将步骤[Ⅰ]中得到的8.5克4-氨基-2-氟苯甲醚与100毫升氢溴酸(47%)混合,然后在90℃下加热搅拌8小时。
反应完毕后,在减压下蒸出过量氢溴酸,接着在残留物中加入碳酸氢钠水溶液予以中和,然后用乙酸乙酯萃取。有机层用饱和氯化钠水溶液洗涤后,用无水硫酸钠干燥。此后再在减压下蒸出乙酸乙酯,从而得到7.3克4-氨基-2-氟苯酚。
[Ⅲ]将步骤[Ⅱ]中得到的7.3克4-氨基-2-氟苯酚溶于100毫升六甲基磷酰三胺中,然后在冰冷却下渐渐加入2.8克氢化钠(60%液体石腊混合物)。添加完毕后使液体温度回复到常温,并继续搅拌20分钟。接着向溶液添加13.6克3,4-二氯三氟甲苯,再将溶液加热至70℃,并使其反应40分钟。
反应完毕后,将反应混合物倾入冰水中,并用乙酸乙酯萃取。有机层先后用水和饱和氯化钠水溶液洗涤,然后用无水硫酸钠干燥。接着在减压下蒸出乙酸乙酯,残留物用硅胶色谱法(展开溶剂∶正己烷/乙酸乙酯=3/1)提纯,由此得到10.4克4-(2-氯-4-三氟甲基苯氧基)-3-氟苯胺,熔点为50-51℃。
[Ⅳ]按照中间体制备例Ⅰ中的步骤[Ⅰ]、[Ⅱ]和[Ⅲ]所述的方法,用步骤Ⅲ所得的4-(2-氯-4-三氟甲基苯氧基)-3-氟苯胺制得4-(2-氯-4-三氟甲基苯氧基)-3-氟(N-甲基)-苯胺,产物的折光指数n27.6 D为1.5424。
按上述中间体制备例所述的相同方法而制备的分子式Ⅲ之化合物的典型例子示于表1。
以下将描述本发明化合物制备方法的具体例子。但是,应当明白本发明决非限于这些具体的例子。
制备例1
N-(4′-溴基-4-联苯基)-N′-(2,6-二氟苯甲酰基)-N-甲脲(29号化合物)的制备
将0.20克4′-溴基-4-甲基氨基联苯溶于5毫升二噁烷中,然后在室温下加入由0.27克2,6-二氟苯甲酰异氰酸酯溶于5毫升二噁烷中所配制而成的溶液,所得混合液在室温下搅拌15小时。
反应完毕后,将反应液倾入100毫升水中,通过过滤收集沉淀析出的晶体,并在减压下进行干燥。使由此所得的固体悬浮在50毫升乙醚中,再用过滤法收集不溶物,由此得到0.26克N-(4′-溴基-4-联苯基)-N′-(2,6-二氟苯甲酰基)-N-甲脲晶体,熔点为183-185℃
制备例2至9
按制备例1所述的方法,采用表2中规定的试剂和反应条件而制备表2所列的化合物。
本发明的化合物在作为农药的活性成分,特别是作为杀虫剂、杀螨剂和对付蛞蝓和蜗牛的农药的活性成分方面显示出极好的活性。例如它们对付下述虫害是有效的:诸如棉红蜘蛛(Tetranychus urticae)、红叶螨(Tetranychus Cinnabarinus)、柑桔红蜘蛛(Panonychus citri)和鳞茎螨(刺足根螨)(Rhizoglyphus echinopus)之类的植物寄生螨;诸如菜蛾(Plutella xylostella)、甘蓝粘虫(夜蛾)(Mamestra brassicae)、普通切根虫(Spodoptera litura)、马铃薯甲虫(Leptinotarsa decemlineata)、苹果蠹蛾(Laspeyresia pomonella)、谷实夜蛾(ballworm)(Heliothis zea)、烟草芽虫(烟草夜蛾)(Helinthis virescens)、球象甲(墨西哥棉铃象)(Anthonomus grandis)、舞毒娥(Lymantris dispar)、南瓜金花虫(Aulacophora femoralis)、吃稻的木虫、蚱蜢、花蝇、金龟子、小地老虎(Agrotis ipsilon)、和地老虎(Agrotis segetum)之类的农业虫害;诸如蟑螂、家蝇(Musca domestica)、家蚊(Culex pipiens pallens)之类的卫生害虫;诸如麦蛾(Sitotroga cerealella)、杂拟谷盗(Tribolium confusum)和粉虫之类的贮藏谷物虫害;诸如织网衣蛾(Tinea pellionella)、黑毛皮蠹(Anthrenus scrophularidae)和地下白蚁之类的家用物品虫害;以及诸如蝇之类的家畜寄生虫。而且它们也能有效地对付下列虫害:对三氯杀螨醇和有机磷杀虫剂有抗药性的螨,以及诸如菜蛾和家蝇之类对有机磷和/或拟除虫菊酯杀虫剂有抗药性的虫害。此外,它们还能有效地对付蛞蝓和蜗牛。
本发明的化合物对昆虫和螨的幼虫显示出特别好的杀幼虫活性。然而,它们对害虫的成虫也是有效的。亦即它们可以如下方式控制虫害的繁殖;当本发明的化合物被成虫摄入后,即可破坏成虫下卵的能力,或阻止卵被孵化。因而它们可在长时间内显示出优良的药效。
本发明之化合物主要用作胃毒剂。因而它们不伤害有益生物,包括那些不以作物为食物的益虫。而且,它们将在土壤中令人满意地分解,因此不会伤害有益的水生生物。为此,作为农药,它们具有较佳的特性。
当本发明的化合物用作农药的活性成分时,可将其与农用辅助剂一起配制成各种形式,如液剂、粉剂、粒剂、可湿性粉剂、可乳化的浓缩物、悬浮剂、烟雾剂、糊剂或就像普通农药那样的超低容量制剂。这类制剂在实际使用时,可以直接施用,也可用水之类合适稀释剂稀释至预定浓度后再予以施用。
这类制剂通常由0.5-90份(以重量计)活性组分和10-99.5份(以重量计)农用辅助剂组成。
农用辅助剂可列举如下:载体、乳化剂、悬浮剂、分散剂、稀释剂、渗透剂、润湿剂、增稠剂和稳定剂。这些辅助剂在需要时可以添加在配方中。载体可分为固态载体和液态载体。固态载体可列举如下:诸如淀粉、活性炭、大豆粉、小麦粉、木粉、鱼粉和奶粉之类的由来源于动、植物体所制成的粉末;诸如滑石、高岭土、膨润土、碳酸钙、沸石、硅藻土、细硅石、粘土、矾土或硫磺粉之类的矿物粉。液体载体可列举如下:诸如甲醇、1,2-亚乙基二醇之类的醇;诸如丙酮、甲基·乙基酮之类的酮;诸如二噁烷、四氢呋喃之类的醚;诸如煤油之类的脂族烃;诸如二甲苯、三甲苯、四甲苯、环己烷和溶剂石脑油之类的芳族烃;诸如氯仿、氯苯之类的卤化烃;诸如二甲基甲酰胺之类的酰胺;诸如乙酸乙酯、脂肪酸的甘油酯之类的酯;诸如乙腈之类的腈;以及诸如二甲基亚矾之类的含硫化合物。
而且,若需要时,本发明之化合物可与其他农药,如杀虫剂、杀螨药、杀线虫剂、杀真菌剂、抗病毒剂、诱虫剂、除草剂或植物生长调节剂一起施用。在某些情况下,这种配合使用将使效率得以提高。
例如,下述物质可作为杀虫剂、杀螨药或杀线虫剂:有机磷化合物、氨基甲酸酯化合物、有机氯化合物、有机金属化合物、拟除虫菊酯化合物、苯甲酰脲化合物和保幼激素类化合物等。此外,诸如苏云金杆菌剂和核多角体病毒等微生物杀虫剂也可与本发明的化合物一起使用。
杀真菌剂可列举如下:有机磷化合物、有机氯化合物、N-卤代硫烷基化合物、二羧基酰亚胺化合物、苯并咪唑化合物、吡咯化合物、甲醇化合物、N-苯甲酰苯胺化合物、酰基丙氨酸化合物、以及吡啶胺化合物等。
本发明之农药能有效地控制各种有害昆虫、有害螨类、以及其他有害虫类。施用的活性组分浓度为1-20,000ppm,最好为20-2,000ppm。活性组份的浓度可以随机改变,取决于配方,施加的方式、目的、时间和地点,以及虫害的情况。例如,水生有害虫类可通过将具有上述浓度的制剂施加到虫害突然蔓延的地点而得以控制,这样,水中活性组分的浓度小于上述范围。
以单位表面积计的活性组分施加量一般约为0.1~5000克,最好每10英亩施加量为5-1000克。但是,在某些特殊情况下,施加量可在上述范围之外。
含有本发明化合物的各种制剂或其稀释合剂可采用通常所用的常规施加方法施用,以产生有毒的(虫害)食物,这些方法包括喷洒(例如喷洒、喷射、烟雾、喷雾、将粉末或颗粒散布或分散在水中);土壤施加(例如混合或浸润);表面施加(例如涂敷、撒粉或撒布);以及浸润等。而且,有可能用含有上述活性组分的饲料喂食家畜,用其排泄物控制害虫的突然蔓延或生长。此外,活性组分也可用所谓超低容量施加法施用,因而制剂可包含100%活性组分。
以下将对本发明的试验例进行描述。
试验例1
对付棉红蜘蛛的杀螨药试验
将含有活性组分的各制剂分散在水中,以配制成每一活性组分浓度为800或200ppm的分散体(相)。仅有一片初生叶的每一株菜豆籽苗被移植在直径为7厘米,高度4厘米的杯中。使约30条棉红蜘蛛(Tetranychus urticae)幼虫和蛹(nimphs)侵染菜豆叶子。然后将菜豆在浓度为800ppm或200ppm的分散体中浸泡10秒种,接着在空气中干燥,此后放置在具有照明的26℃恒温室中。经5天处理后,清点死亡的螨数,并用下式计算致死率:
致死率(%)= (死螨数)/(总螨数) ×100
结果示于表4。
表4
化合物编号 致死率 (%)
800ppm 200ppm
4 90 -
12 100 100
13 - 99
18 - 100
试验例2
对付菜蛾的杀虫剂试验
将含有活性组分的各种制剂分散在水中,以配制成活性组分浓度为10ppm的分散体。再将甘蓝叶子在相应的分散体中浸泡10秒钟,然后在空气中干燥。将一张湿滤纸放在直径为9厘米的(皮氏)培养皿中,并将干燥后的甘蓝叶子放在滤纸上。将第二或第三龄期的菜蛾(Plutella xylostella)幼虫放到叶子上后,盖上培养皿,并放置在具有照明的26℃恒温室中。7天后,清点死虫数,并用下式计算致死率:
致死率(%)= (死虫数)/(总虫数) ×100
结果表明,化合物编号为1-10,12-36,39,41,43-47,49-57,62-74,76-77,80-86,108-109,111-115,125和126的致死率均为100%,而化合物编号为40和75的致死率为90%。
试验例3
对付切根虫的杀虫剂试验
按试验例2所述的同样方法进行试验,但用第2或3龄期的普通切根虫(Spodoptera litura)的幼虫代替第二或第三龄期的菜蛾幼虫,而且活性组分的浓度由10ppm改变成800ppm或1ppm。
在活性组分浓度为800ppm时,编号为1-86,108-109,111-115,125和126的化合物的致死率均为100%。
在活性组分浓度为1ppm时,编号为1-8,11-27,29,31-36,39-41,43-47,49-60,62-63,65-66,68-72,74,76-78,80,82-86,108-109,111-113,115,125和126的化合物,其致死率均为100%,而编号为64和75的化合物,致死率为90%。
试验例4
对付家蝇幼虫的杀幼剂试验
供试验动物的粉末饲料(由Oriental Kobo Kogyo K.K制造)与糠以1∶1的重量比混合后磨细,然后将10克混合物装填在冰淇淋杯中。将含有活性组分的各制剂分散在水中,然后将10毫升分散体加到冰淇淋杯的混合物中,以使活性组分的浓度调节至10ppm。在上述冰淇淋杯中放入20条第二龄期的家蝇(Musca domestica)幼虫,并放置在具有照明的26℃恒温室中。放入幼虫后10天,清点所出现的成虫数,然后按下式计算致死率:
致死率(%)= (放入的幼虫数-出现的成虫数)/(放入的幼虫数) ×100
结果表明,编号为1-5,12-13,和24的化合物,致死率均为100%,而编号为6的化合物,致死率为90%。
试验例5
对付家蚊幼虫的杀幼虫剂试验
将活性组分含量为2.5ppb的200毫升稀溶液倾入一只缸中,并放着20只家蚊(Cullex pipiens pallens)幼虫。然后将缸放置在具有照明的26℃恒温室中。每隔一天用1-2毫克粉末饲料喂食幼虫。放入幼虫后第9天,清点死虫数,并按试验例2同样的方式计算致死率。结果示于表5。
表5
化合物编号 致死率(%)
2.5ppb
1 100
2 90
3 100
4 100
试验例6
通过处理家蝇成虫而进行卵孵化抑制试验
将糖和脱脂牛奶以1∶1重量比混合,然后将2克混合物加到直径为5.5厘米的(皮氏)培养皿中。接着加入含有活性组分的0.5毫升丙酮溶液。使丙酮蒸发后,将处理过的混合物充分混合,并将活性组分浓度调节至10微克/克。用有毒的食物(处理过的混合物)喂食笼内20只末交配的雌家蝇(Musca domestica)。3天后,将食物换成未处理过的混合物,然后在笼内放入20只未交配的雄家蝇,以进行交配。放入雄家蝇后第3天,一杯供培育蝇幼虫用的培养基放入笼内7小时,以供产卵。收集产在培养基中的卵,并置于(皮氏)培养皿的湿滤纸上。一天后,查明未孵化的卵,并用下式计算卵孵化抑制率(REHI):
REHI(%)= (未孵化卵的数目)/(收集到的卵数目) ×100
结果表明,编号为1,5,12-13,15,20,24,29和31的化合物,卵孵化抑制率为100%,而3号化合物的相应数值为88%。
试验例7
Ⅰ.杀虫试验
按试验例2和3所述的同样方法,用每一种化合物进行对付菜蛾和普通切根虫的杀虫试验,由此得到杀虫率不低于90%的最低浓度(以下称为C-值)。
将各化合物的丙酮溶液分散在水中,以得到不同活性组分浓度的试验溶液。然后对各试验溶液分别取25.0毫升,并放入各只430毫升玻璃烧杯中。在每一烧杯中再放入10条在24小时内孵出的第一龄期幼虫,并保持在23±1℃的溶液温度下。按照OECD试验准则探查放入幼虫后直至48小时的活动性降低率。对于每一浓度进行二组试验,并重复2-3次。由Probit法得到50%活动性降低率的浓度(EC50,ppb)。
Ⅲ.土壤中残留物试验
用筛孔尺寸为5毫米的筛子过筛高地土(火山灰土),将20克土(以干重计)放入锥形烧瓶中,然后在横拟灌溉条件下引入蒸馏水,水深为1厘米。在烧瓶顶部盖上铝铂,并在30℃恒温箱(暗处)中静置1周。
用移液管取出化合物浓度为200ppm的丙酮分散体0.5毫升(含有100微克化合物),并加到烧瓶中(使之浓度为5ppm)。将烧瓶封盖,并充分摇动,用少量水将附着在壁上的土洗入烧瓶中。然后用铝铂盖在烧瓶顶部,并放入培育箱(30℃,60%湿度,连续用9,000勒克司荧火灯照明)进行培养。20天后,对全部20克土壤进行分析,并测定化合物的残留量。
试验Ⅰ、Ⅱ和Ⅲ的结果示于表6。
以下将描述本发明的配方例。然而,本发明之化合物,活性组分的量或制剂形式并非限于这些具体例子。
配方例1
(a)18号化合物 20份(以重量计,下同)
(b)高岭土 72份
(c)木素磺酸钠 8份
将上述组分均匀地混合,以得到可湿性粉末。
配方例2
(a)24号化合物 5份(以重量计,下同)
(b)滑石粉 95份
将上述组分均匀地混合,以得到粉剂。
配方例3
(a)3号化合物 20份(以重量计,下同)
(b)N,N′-二甲基甲酰胺 20份
(c)聚氧乙烯烷基苯基醚 10份
(d)二甲苯 50份
将上述组分均匀地混合和溶解,以得到可乳化的浓缩物。
配方例4
(a)高岭土 78份(以重量计,下同)
(b)木素磺酸钠 2份
(c)聚氧乙烯烷基芳基硫酸盐 5份
(d)细硅石粉 15份
将上述组分的混合物与31号化合物以4∶1的重量比混合,以得到可湿性粉末。
配方例5
(a)46号化合物 40份(以重量计,下同)
(b)氧化(oxylated)聚
烷基苯酚磷酸三乙醇胺 2份
(c)硅 0.2份
(d)苍耳烷胶(Xanthan gun) 0.1份
(e)1,2-亚乙基二醇 5份
(f)水 52.7份
将上述组分均匀混合和磨碎,以得到悬浮剂。
配方例6
(a)3号化合物 50份(以重量计,下同)
(b)氧化聚烷基苯酚磷酸 2份
三乙醇胺
(c)硅 0.2份
(d)水 47.8份
将上述组分均匀混合和磨碎,以得到基液,再加入
(e)聚羧酸钠 5份
(Sosium polgcarboxylate)
(f)无水硫酸钠 42.8份
并将上述组分均匀混合,干燥后得到干悬浮剂。
配方例7
(a)49号化合物 5份(以重量计,下同)
(b)丙三醇 20份
(c)奶粉 3份
(d)鱼粉 72份
将上述组分均匀地捏和,以得到糊剂。
配方例8
(a)57号化合物 5份(以重量计,下同)
(b)麦麸 10份
(c)米糠 80份
(d)糖蜜 5份
将上述组分均匀地混合,并与少量水一起捏和,然后通过挤压成形使之成为颗粒形式,干燥后即得粒剂。
配方剂9
(a)76号化合物 2.5份(以重量计,下同)
(b)N-甲基-2-吡咯烷酮 2.5份
(c)豆油 95.0份
将上述组分均匀地混合和溶解,以得到超低容量的制剂。
配方例10
(a)29号化合物 5份(以重量计,下同)
(b)N,N′-二甲基甲酰胺 5份
(c)聚氧乙烯烷基芳基醚 10份
(d)二甲苯 80份
将上述组分均匀地混合,以得到可乳化的浓缩物。
Claims (12)
1、一种分子式为
的苯甲酰脲化合物或其盐的制备方法,式中X1和X2各自为氢原子、卤素原子或甲基,但X1和X2不能同时为氢原子;Y可以是氢原子、卤素原子、烷基或(氢原子)被卤素取代的烷基、-CO2R1基(其中R1是氢原子、阳离子或烷基)、或-OR1基(其中R的定义与上述相同);A是=N-或
(其中Y的定义与上述相同);W是氧原子、硫原子或
(其中R1的定义与上述相同);k是1至3的整数;1是0或1;而Ar是
,其中Z可以是氢原子、卤素原子、烷基或被卤素取代的烷基、烷氧基或被卤素取代的烷氧基、硝基、氰基或-S(O)nR2基,其中R2是烷基或被卤素取代的烷基,n是0、1或2,A2是-S-、
(其中Z的定义与上述相同),而m是1至3的整数,所说方法包括使分子式为
3、根据权利要求1所述的化合物或其盐的制备方法,其特征在于X1和X2各自是氢原子或卤素原子,但至少其中一个是氢原子。
6、根据权利要求1所述的化合物或其盐的制备方法,其特征在于所说化合物是N-[3,5-二氯-4-(3-氯-5-三氟甲基-2-吡啶氧基)苯基]-N′-(2,6-二氟甲酰基)-N-甲脲。
7、根据权利要求1所述的化合物或其盐的制备方法,其特征在于所说化合物是:
(1)N-[4-(3-氯-5-三氟甲基-2-吡啶氧基)-2,3-二氟苯基]-N′-(2,6-二氟苯甲酰基)-N-甲脲;
(2)N-[3-氯-4-(3-氯-5-三氟甲基-2-吡啶氧基)-苯基]-N′-(2,6-二氟苯甲酰基)-N-甲脲;
(3)N-[4-(3-氯-5-三氟甲基-2-吡啶氧基)-2,5-二甲基苯基]-N′-(2,6-二氟苯甲酰基)-N-甲脲;
(4)N-[3-氯-4-(3-氯-5-三氟甲基-2-吡啶氧基)-2-氟苯基]-N′-(2,6-二氟苯甲酰基)-N-甲脲;
(5)N-[4-(3-氯-5-三氟甲基-2-吡啶氧基)苯基]-N′-(2-氯代苯甲酰基)-N-甲脲;
(6)N-[4-(2-氯-4-三氟甲基苯甲氧基)-2,3-二氟苯基]-N′-(2,6-二氟苯甲酰基)-N-甲脲;
(7)N-[3-氯-4-(2-氯-4-三氟甲基苯氧基)苯基]-N′-(2,6-二氟苯甲酰基)-N-甲脲;
(8)N-[3-氯-4-(2-氯-4-三氟甲基苯氧基)-2-氟苯基]-N′-(2,6-二氟苯甲酰基)-N-甲脲;
(9)N-[4-(2-氯-4-三氟甲基苯氧基)苯基]-N′-(2,6-二氟苯甲酰基)-N-甲脲;
(10)N-[3-氯-4-(2-氯-4-三氟甲基苯氧基)苯基]-N′-(2-氯苯甲酰基)-N-甲脲;
(11)N-[4-(3-氯-5-三氟甲基-2-吡啶氧基)-2-甲基苯基]-N′-(2,6-二氟苯甲酰基)-N-甲脲;
(12)N-{4-[3-氯-5-三氟甲基-2-吡啶氧基]-3-氟苯基}-N′-(2,6-氟苯甲酰基)-N-脲;
(13)N-{4-[2-氯-4-三氟甲基苯氧基]-3-氟苯基}-N′-(2,6-二氟苯甲酰基)-N甲脲;
(14)N-{4-(2-氯-4-三氟甲基苯氧基)-3,5-二氟苯基}-N′-(2,6-二氟苯甲酰基)-N-甲脲;
(15)N-{4-[2-氯-4-三氟甲基苯氧基]-3-甲基苯基}-N′-2,6-二氟苯甲酰基-N-甲脲;或
(16)N-{4-[3-氯-5-三氟甲基-2-吡啶氧基]-3-甲基苯基}-N′-(2-氯苯甲酰基)-N-甲脲;
8、根据权利要求1所述的化合物,其特征在于所说的化合物是:
(1)N-(4′-氯-2-氟-4-联苯基)-N′-(2,6-二氟苯甲酰基)-N-甲脲;
(2)N-(4′-(溴-4-联苯基)-N′-(2,6-二氟苯甲酰基)-N-甲脲;
(3)N-[2,5-二氟-4′-氯-4-联苯基)-N′-(2,6-二氟苯甲酰基)-N-甲脲;
(4)N-(2-三氟甲基-4′-氯-4-联苯基)-N′-(2,6-二氟苯甲酰基)-N-甲脲;或
(5)N-(2,5-二氟-3′-三氟甲基硫-4-联苯基)-N′-(2,6-二氟苯甲酰基)-N-甲脲。
9、根据权利要求1所述的方法,其特征在于所说反应在-10℃至+100℃温度的溶剂中进行。
10、一种农药药剂,它包括对杀虫作用有效量的权利要求1所定义的苯甲酰脲化合物和农业上可接受的辅助剂。
11、根据权利要求10所述的农药药剂,其特征在于它包括0.5-90份苯甲酰脲化合物和10-99.5份辅助剂(以上含量均以重量计)。
12、一种控制虫害的方法,它包括向欲被保护的区域施加对杀虫作用有效量的权利要求1所定义的苯甲酰脲化合物。
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Families Citing this family (32)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0360748A1 (de) * | 1988-09-21 | 1990-03-28 | Ciba-Geigy Ag | Benzoylphenylharnstoffe |
IT1272943B (it) * | 1994-02-01 | 1997-07-01 | Bend Res Inc | Composizioni insetticide labili |
WO1998019995A1 (en) * | 1996-11-08 | 1998-05-14 | Dow Agrosciences Llc | New benzoylphenylurea insecticides ans methods of using them to control cockroaches |
US5945453A (en) * | 1996-11-08 | 1999-08-31 | Dow Agrosciences Llc | Benzoylphenylurea insecticides to control cockroaches |
US5886221A (en) | 1997-11-03 | 1999-03-23 | Dow Agrosciences Llc | Benzoylphenylurea insecticides and methods of using certain benzoylphenylureas to control cockroaches, ants, fleas, and termites |
US6187799B1 (en) * | 1997-05-23 | 2001-02-13 | Onyx Pharmaceuticals | Inhibition of raf kinase activity using aryl ureas |
US6344476B1 (en) | 1997-05-23 | 2002-02-05 | Bayer Corporation | Inhibition of p38 kinase activity by aryl ureas |
US5811461A (en) * | 1997-10-31 | 1998-09-22 | Dow Agrosciences Llc | Benzoylphenylurea insecticides and methods of using them to control cockroaches, ants, fleas, and termites |
US20080300281A1 (en) * | 1997-12-22 | 2008-12-04 | Jacques Dumas | Inhibition of p38 Kinase Activity Using Aryl and Heteroaryl Substituted Heterocyclic Ureas |
US7329670B1 (en) * | 1997-12-22 | 2008-02-12 | Bayer Pharmaceuticals Corporation | Inhibition of RAF kinase using aryl and heteroaryl substituted heterocyclic ureas |
US7517880B2 (en) | 1997-12-22 | 2009-04-14 | Bayer Pharmaceuticals Corporation | Inhibition of p38 kinase using symmetrical and unsymmetrical diphenyl ureas |
US20080269265A1 (en) * | 1998-12-22 | 2008-10-30 | Scott Miller | Inhibition Of Raf Kinase Using Symmetrical And Unsymmetrical Substituted Diphenyl Ureas |
ATE556713T1 (de) * | 1999-01-13 | 2012-05-15 | Bayer Healthcare Llc | Omega-carboxyarylsubstituierte-diphenyl- harnstoffe als p38-kinasehemmer |
US7928239B2 (en) | 1999-01-13 | 2011-04-19 | Bayer Healthcare Llc | Inhibition of RAF kinase using quinolyl, isoquinolyl or pyridyl ureas |
US8124630B2 (en) | 1999-01-13 | 2012-02-28 | Bayer Healthcare Llc | ω-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors |
EP1140840B1 (en) | 1999-01-13 | 2006-03-22 | Bayer Pharmaceuticals Corp. | -g(v)-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors |
ME00275B (me) * | 1999-01-13 | 2011-02-10 | Bayer Corp | ω-KARBOKSIARIL SUPSTITUISANI DIFENIL KARBAMIDI KAO INHIBITORI RAF KINAZE |
US6472528B1 (en) | 1999-08-10 | 2002-10-29 | Neurocrine Biosciences, Inc. | Synthesis of substituted pyrazolopyrimidines |
EP1344768B1 (en) * | 1999-08-10 | 2005-04-06 | Neurocrine Biosciences, Inc. | Synthesis of substituted pyrazolopyrimidines |
US7235576B1 (en) | 2001-01-12 | 2007-06-26 | Bayer Pharmaceuticals Corporation | Omega-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors |
US7371763B2 (en) * | 2001-04-20 | 2008-05-13 | Bayer Pharmaceuticals Corporation | Inhibition of raf kinase using quinolyl, isoquinolyl or pyridyl ureas |
WO2003047579A1 (en) * | 2001-12-03 | 2003-06-12 | Bayer Pharmaceuticals Corporation | Aryl urea compounds in combination with other cytostatic or cytotoxic agents for treating human cancers |
US20080108672A1 (en) * | 2002-01-11 | 2008-05-08 | Bernd Riedl | Omega-Carboxyaryl Substituted Diphenyl Ureas As Raf Kinase Inhibitors |
AU2003210969A1 (en) * | 2002-02-11 | 2003-09-04 | Bayer Corporation | Aryl ureas with raf kinase and angiogenesis inhibiting activity |
WO2003068229A1 (en) * | 2002-02-11 | 2003-08-21 | Bayer Pharmaceuticals Corporation | Pyridine, quinoline, and isoquinoline n-oxides as kinase inhibitors |
AU2003209116A1 (en) * | 2002-02-11 | 2003-09-04 | Bayer Pharmaceuticals Corporation | Aryl ureas with angiogenesis inhibiting activity |
WO2003068746A1 (en) | 2002-02-11 | 2003-08-21 | Bayer Pharmaceuticals Corporation | Aryl ureas as kinase inhibitors |
US7557129B2 (en) * | 2003-02-28 | 2009-07-07 | Bayer Healthcare Llc | Cyanopyridine derivatives useful in the treatment of cancer and other disorders |
PT1636585E (pt) * | 2003-05-20 | 2008-03-27 | Bayer Pharmaceuticals Corp | Diarilureias com actividade inibidora de cinase |
JP4777887B2 (ja) * | 2003-07-23 | 2011-09-21 | バイエル、ファーマシューテイカルズ、コーポレイション | 病気および状態の処置および防止のためのフロロ置換オメガカルボキシアリールジフェニル尿素 |
EP1937629A2 (en) * | 2005-10-20 | 2008-07-02 | Sumitomo Chemical Company, Limited | Benzoylurea compounds and use thereof |
PL2734510T4 (pl) | 2011-07-22 | 2019-05-31 | Massachusetts Inst Technology | Aktywatory deacetylaz histonowych klasy I (HDAC) i ich zastosowania |
Family Cites Families (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL160809C (nl) * | 1970-05-15 | 1979-12-17 | Duphar Int Res | Werkwijze ter bereiding van benzoylureumverbindingen, alsmede werkwijze ter bereiding van insekticide prepara- ten op basis van benzoylureumverbindingen. |
DE2438747C2 (de) * | 1974-08-13 | 1982-10-14 | Bayer Ag, 5090 Leverkusen | Benzoylureido-diphenyläther, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide |
GB1460419A (en) * | 1975-02-06 | 1977-01-06 | Bayer Ag | Benzoylureido-diphenyl ethers and their use as insecticides |
DE2531202C2 (de) * | 1975-07-12 | 1982-12-09 | Bayer Ag, 5090 Leverkusen | 2',4-Dichlor-4'-benzoylureido- diphenyläther, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide |
US4173637A (en) * | 1976-10-29 | 1979-11-06 | Ishihara Sangyo Kaisha Ltd. | N-Benzoyl-N'-pyridyloxy phenyl urea and insecticidal compositions thereof |
JPS5840946B2 (ja) * | 1976-10-29 | 1983-09-08 | 石原産業株式会社 | N−ベンゾイル−n′−ピリジルオキシフエニルウレア系化合物、それらの製造方法及びそれらを含有する殺虫剤 |
DE2861549D1 (en) * | 1978-02-10 | 1982-03-04 | Ciba Geigy Ag | Substituted diaminophthalides, process for their preparation and their use as colour formers in pressure or heat sensitive recording materials |
US4243680A (en) * | 1979-02-07 | 1981-01-06 | Thompson-Hayward Chemical Company | Method of reducing infestation of citrus rust mites on citrus trees |
AU532156B2 (en) * | 1979-09-07 | 1983-09-22 | Ishihara Sangyo Kaisha Ltd. | N-benzoyl-n'-pyridyloxy phenyl urea |
DE3217619A1 (de) * | 1982-05-11 | 1983-11-17 | Bayer Ag, 5090 Leverkusen | 2,4-dihalogenbenzoyl-(thio)harnstoffe, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel |
DE3217620A1 (de) * | 1982-05-11 | 1983-11-17 | Bayer Ag, 5090 Leverkusen | 2,5-dihalogenbenzoyl-(thio)harnstoffe, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel |
CA1205483A (en) * | 1982-06-30 | 1986-06-03 | David T. Chou | Pesticidal 1-(alkyl phenoxyaryl)-3-benzoyl ureas and process for preparation |
DE3378207D1 (en) * | 1983-01-24 | 1988-11-17 | Duphar Int Res | Benzoylurea compounds and pesticidal compositions comprisingsame |
CA1265150A (en) * | 1983-03-31 | 1990-01-30 | John K. Chan | Process for the preparation of benzoyl ureas |
US4659736A (en) * | 1984-01-21 | 1987-04-21 | Bayer Aktiengesellschaft | Benzoyl urea compounds as agents for repelling snails and slugs |
GB8420930D0 (en) * | 1984-08-17 | 1984-09-19 | Shell Int Research | Pesticidal benzoylurea compounds |
CA1339745C (en) * | 1984-04-10 | 1998-03-17 | Martin Anderson | Pesticidal benzoylurea compounds |
ZA868191B (en) * | 1985-10-29 | 1987-07-29 | Ciba Geigy Ag | Salts of benzoylureas |
-
1987
- 1987-09-28 NZ NZ221964A patent/NZ221964A/xx unknown
- 1987-09-29 EG EG55187A patent/EG18573A/xx active
- 1987-09-29 CN CN87106674A patent/CN1023006C/zh not_active Expired - Fee Related
- 1987-09-30 AU AU79234/87A patent/AU594199B2/en not_active Expired
- 1987-09-30 US US07/102,855 patent/US4861799A/en not_active Expired - Fee Related
- 1987-10-01 EP EP87114341A patent/EP0263438B1/en not_active Expired - Lifetime
- 1987-10-01 ES ES87114341T patent/ES2051719T3/es not_active Expired - Lifetime
- 1987-10-01 DE DE8787114341T patent/DE3780396T2/de not_active Expired - Lifetime
- 1987-10-02 CA CA000548485A patent/CA1340938C/en not_active Expired - Fee Related
- 1987-10-02 DK DK518987A patent/DK169151B1/da not_active IP Right Cessation
- 1987-10-02 PL PL1987268033A patent/PL153343B1/pl unknown
- 1987-10-02 BR BR8705244A patent/BR8705244A/pt not_active IP Right Cessation
- 1987-10-02 PH PH35883A patent/PH25153A/en unknown
- 1987-10-02 AR AR87308914A patent/AR245706A1/es active
- 1987-10-02 RU SU874203447A patent/RU2032343C1/ru active
- 1987-10-02 KR KR1019870011046A patent/KR940011908B1/ko not_active IP Right Cessation
-
1989
- 1989-06-13 US US07/365,607 patent/US4985449A/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
EP0263438A2 (en) | 1988-04-13 |
KR880005071A (ko) | 1988-06-27 |
US4861799A (en) | 1989-08-29 |
ES2051719T3 (es) | 1994-07-01 |
EP0263438B1 (en) | 1992-07-15 |
PL268033A1 (en) | 1989-05-16 |
DK518987A (da) | 1988-04-04 |
AU7923487A (en) | 1988-04-14 |
CN1023006C (zh) | 1993-12-08 |
DK518987D0 (da) | 1987-10-02 |
AR245706A1 (es) | 1994-02-28 |
BR8705244A (pt) | 1988-05-24 |
KR940011908B1 (ko) | 1994-12-27 |
CA1340938C (en) | 2000-03-28 |
PL153343B1 (en) | 1991-04-30 |
AU594199B2 (en) | 1990-03-01 |
EG18573A (en) | 1994-06-30 |
DE3780396D1 (de) | 1992-08-20 |
EP0263438A3 (en) | 1989-03-15 |
US4985449A (en) | 1991-01-15 |
DE3780396T2 (de) | 1993-02-11 |
PH25153A (en) | 1991-03-27 |
RU2032343C1 (ru) | 1995-04-10 |
NZ221964A (en) | 1990-03-27 |
DK169151B1 (da) | 1994-08-29 |
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