WO2020030096A1 - Composition médicamenteuse contenant le composé m-diamide et application de la composition médicamenteuse - Google Patents

Composition médicamenteuse contenant le composé m-diamide et application de la composition médicamenteuse Download PDF

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WO2020030096A1
WO2020030096A1 PCT/CN2019/099952 CN2019099952W WO2020030096A1 WO 2020030096 A1 WO2020030096 A1 WO 2020030096A1 CN 2019099952 W CN2019099952 W CN 2019099952W WO 2020030096 A1 WO2020030096 A1 WO 2020030096A1
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Prior art keywords
compound
active ingredient
pharmaceutical composition
composition containing
insecticidal
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PCT/CN2019/099952
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English (en)
Chinese (zh)
Inventor
倪珏萍
相君成
吕亮
洪湖
刘吉永
邵佳礼
周丽琪
刘叙杆
Original Assignee
上海泰禾国际贸易有限公司
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Priority claimed from CN201910704042.6A external-priority patent/CN110810409B/zh
Application filed by 上海泰禾国际贸易有限公司 filed Critical 上海泰禾国际贸易有限公司
Publication of WO2020030096A1 publication Critical patent/WO2020030096A1/fr

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    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/46—N-acyl derivatives
    • 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
    • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
    • A01N31/14—Ethers
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/28—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the group; Thio analogues 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/34—Nitriles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/10—Sulfones; Sulfoxides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
    • A01N43/32—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
    • A01N43/68—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms with two or three nitrogen atoms 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
    • A01N47/08—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
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
    • 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
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
    • 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
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/22—O-Aryl or S-Aryl esters 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
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues 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
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or 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
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
    • A01N57/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing acyclic or cycloaliphatic radicals
    • 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
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
    • A01N57/14—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing aromatic radicals
    • 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
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
    • A01N57/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing heterocyclic radicals
    • 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
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/26—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds
    • A01N57/28—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds containing acyclic or cycloaliphatic radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
    • C07C237/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/50—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles

Definitions

  • the present application belongs to the technical field of prevention and control of harmful organisms by pharmaceutical compositions, and relates to a pharmaceutical composition containing a metadiamide compound and its application.
  • CN101208009A discloses that a composition containing a metadiamide compound has an insecticidal effect, and various types of pesticides and fungicides of various structure types in the prior art are widely used in various crops. With the continuous use of pesticides, pests and diseases will become resistant to some existing pesticide products, and the insecticidal activity of existing pesticide varieties may not always meet the needs of many agricultural practices.
  • Insecticide compositions have an important role in improving the effectiveness of insecticides, expanding the spectrum of control, and delaying the development of resistance. Therefore, in the art, it is still desired to develop more efficient insecticide compositions or insecticidal bactericidal compositions to meet the needs of agriculture and the forestry industry.
  • the purpose of the present application is to provide a pharmaceutical composition containing an m-diamide compound and its application.
  • the pharmaceutical composition has a synergistic effect, and can prevent and control diseases caused by pests and diseases.
  • the present application provides a pharmaceutical composition containing an m-diamide compound.
  • the pharmaceutical composition includes an active ingredient A and an active ingredient B.
  • the active ingredient A is an amide compound having a structure represented by Formula I.
  • the active ingredient B includes any one or a combination of two other pesticides or fungicides;
  • Z is selected from hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, substituted or unsubstituted 3-10 membered heterocyclic group, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylsulfinyl, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 alkylsulfonyl or C 1 -C 6 haloalkylsulfonyl;
  • Q is selected from C 3 -C 8 cycloalkyl or C 3 -C 8 halocycloalkyl;
  • X is selected from hydrogen, fluorine or trifluoromethyl
  • Y 1 is selected from fluorine, chlorine, bromine, iodine, cyano, nitro, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 haloalkoxy, C 2 -C 4 alkenyl , C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 2 -C 4 haloalkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, C 1- C 6 alkylcarbonyl, C 1 -C 6 alkylsulfinyl, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 alkylsulfonyl or C 1 -C 6 haloalkylsulfonyl;
  • Y 2 is selected from bromine, iodine, cyano, nitro, C 1 -C 6 haloalkyl, C 1 -C 6 haloalkoxy, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 2 -C 4 haloalkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkylsulfinyl, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 alkylsulfonyl or C 1 -C 6 haloalkylsulfonyl;
  • R 1 is selected from hydrogen, fluorine or methoxy
  • R 2 is selected from fluorine or trifluoromethyl
  • R 3 and R 4 are each independently selected from hydrogen, halogen, cyano, nitro, C 1 -C 6 alkyl , C 1 -C 6 haloalkyl, C 3 -C 8 cycloalkyl or C 3 -C 8 halocycloalkyl;
  • n represents an integer of 0 to 3 (for example, 0, 1, 2 or 3); W 1 and W 2 are independently an oxygen atom Or sulfur atom.
  • the pharmaceutical composition using the m-bisamide compound having the structure shown by the formula I as described in the present application as the active ingredient A and blended with the active ingredient B has a synergistic effect between the active ingredient A and the active ingredient B.
  • the control effect is significantly improved, and because the active ingredient A can achieve a good insecticidal activity at a low dose, the effect is fast, and the fast-acting property is good, so the
  • the pharmaceutical composition also has good fast-acting properties, and because of its good effect at low doses, it reduces damage to plants and human beings caused by excessive drug concentrations, and reduces the generation of drug residues during application, which is more conducive to environmental protection.
  • the present application provides a pesticide composition pharmaceutical composition containing a compound substituted at the 3-position of m-diamide with an N-cyclopropylmethyl derivative.
  • the pharmaceutical composition includes active ingredient A and active ingredient B.
  • Active ingredient A is a metadiamide compound having a structure represented by Formula II, and the active ingredient B includes any one or a combination of other fungicides, insecticides, or acaricides;
  • Z is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, cyano, C 1 -C 6 haloalkyl, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylsulfonyl, or C 1 -C 6 haloalkyl Sulfonyl
  • Y is selected from C 1 -C 6 haloalkyl or C 1 -C 6 haloalkoxy;
  • R is selected from hydrogen or methyl.
  • an m-bisamide compound having a structure represented by Formula II is further preferred, and it is compounded with active ingredient B as an active ingredient of a pharmaceutical composition. Good results can be achieved at low doses, resulting in less drug residues and more environmental protection.
  • Z is selected from hydrogen, fluorine, chlorine, bromine, iodine, cyano, trifluoromethoxy, trifluoromethyl, methanesulfonyl, or trifluoromethanesulfonyl.
  • Y is selected from trifluoromethyl or trifluoromethoxy
  • R is selected from hydrogen or methyl.
  • the m-bisamide compound is any one of the compounds shown in Table 1 below having the general formula II.
  • H is a hydrogen atom
  • F is a fluorine atom
  • Cl is a chlorine atom
  • Br is a bromine atom
  • I is an iodine atom
  • CN is a cyano group
  • CF 3 is a trifluoromethyl group
  • OCF 3 is a trifluoromethoxy group
  • MeS (O) 2 represents a methylsulphonyl group
  • CF 3 S (O) 2 Representative trifluoromethanesulfonyl.
  • the m-diamide compound is any one or a combination of at least two selected from the following compounds 1-14:
  • C 1 -C 6 alkyl refers to a straight or branched chain alkyl group having 1 to 6 carbon atoms, and includes, without limitation, methyl, ethyl, n-propyl, isopropyl, N-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, iso-pentyl, n-hexyl and the like.
  • C 1 -C 6 alkoxy refers to a straight or branched chain alkoxy group having 1 to 6 carbon atoms, including without limitation methoxy, ethoxy, n-propoxy, isopropyl Oxy, t-butoxy and the like.
  • C 1 -C 6 haloalkyl refers to an alkyl group having 1 to 6 carbon atoms substituted with a halogen, and includes, without limitation, chloromethyl, 1-chloroethyl, 2-bromo-n-propyl, and the like.
  • C 1 -C 6 haloalkoxy refers to an alkoxy group having 1 to 6 carbon atoms substituted with halogen; similarly the term “C 3 -C 8 cycloalkyl” refers to having 3 to 8 on the ring A cyclic alkyl group of one carbon atom, including but not limited to cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, etc .; the term “C3-C8 halocycloalkane” used in this application "Group” refers to a cyclic alkyl group having 3 to 8 carbon atoms substituted with a halogen on the ring, and includes, without limitation, 1-chlorocyclopropyl, 1-fluorocyclopropyl, perfluorocyclopropyl , 1-chlorocyclobutyl, 1-chlorocyclopentyl and the like.
  • C 1 -C 6 , C 3 -C 8, etc. before the specific group indicate the number of carbon atoms contained in the group, for example, C 1 -C 6 indicates that the number of carbon atoms can be 1, 2 , 3, 4, 5, or 6 groups, C 3 -C 8 represent groups having 3 , 4, 5, 6, 7, or 8 carbon atoms, and so on.
  • the active ingredient B is selected from the group consisting of organophosphorus, pyrethroids, carbamates, wormworms, or insect growth regulators.
  • the organophosphorus insecticide is selected from the group consisting of chlorpyrifos, acephate, phoxim, dichlorvos, triazophos, profenfos, thiazophos, malathion, fenthion, dimethoate, Omethoate, diazinon, hydraxine, or a combination of at least two of them;
  • the synthetic pyrethroid insecticide is selected from the group consisting of lambda-cyhalothrin, deltamethrin, bifenthrin, cypermethrin, permethrin, fenvalerate, fenvalerate, and ethonitrile Permethrin, cypermethrin, tefluthrin, tetramethrin, deltamethrin, permethrin, flumethrin, fenethrin, cyhalothrin and their various isomers or compounds A combination of at least two of the pyrethroid insecticides is described.
  • the urethane-based insecticide is selected from the group consisting of metronidyl, isopropylcarb, secbutacarb, sulfandicarb, antiacarb, phenoxycarb, or a combination of at least two of them;
  • the wormworm toxin-type insecticide is selected from the group consisting of insecticidal single, insecticidal double, insecticidal ring, carbendazim, or a combination of at least two of them;
  • the insect growth regulator is selected from the group consisting of fluoxuron, diflubenzuron, flubenzuron, flubenzuron, chlorfenuron, imazapyr, pyriproxyfen, dioxocarb, carbazide, and hydrazine Or a combination of at least two of them.
  • Insect growth regulators hinder insect-specific molting, metamorphosis and other developmental processes to achieve the purpose of controlling pests and are safe for humans and animals, so they have been developed and applied in large quantities; however, their problems of poor effectiveness need to be compounded with other agents.
  • the pharmaceutical composition containing the metadiamide compound is a pharmaceutical composition containing the metadiamide compound (active ingredient A) and the active ingredient B described in Table 2 below, but not Limited to the combinations listed in the table.
  • Harmful effects of the pharmaceutical composition were tested using pests such as pupae, diamondback moth, armyworm, alfalfa aphid, brown planthopper, leaffly, whitefly and other harmful organisms, and a composition having a synergistic effect was found.
  • the weight ratio of the active ingredient A and the active ingredient B described herein is 200: 1 to 1: 200, for example, 200: 1, 180: 1, 150: 1, 130: 1, 100: 1, 80: 1, and 60: 1, 40: 1, 20: 1, 10: 1, 1: 1, 1:10, 1:30, 1:50, 1:80, 1: 100, 1: 120, 1: 140, 1: 160, 1: 180 or 1: 200.
  • the pharmaceutical composition containing the metadiamide compound has different preferred weight ratios according to the difference between the active ingredient A and the active ingredient B.
  • the active ingredient is When A and active ingredient B are selected from the components described in Table 3, their preferred weight ratios and particularly preferred weight ratios are shown in Table 3.
  • the m-diamide compound may also be replaced with a tautomer, an enantiomer, a diastereomer or a salt thereof.
  • a pharmaceutical composition containing the tautomer, enantiomer, diastereomer, or a salt of the m-diamide compound can also exert the same properties as the m-diamide-containing compound described in the present application.
  • the pharmaceutical composition has the same action effect, good insecticidal effect and fast-acting effect at a low dose.
  • the present application provides a pharmaceutical formulation comprising a pharmaceutical composition containing an m-diamide compound as described above and an agrochemically acceptable adjuvant and / or carrier.
  • the weight percentage content of the mesodiamide compound-containing pharmaceutical composition is 0.01-99%, such as 0.01%, 0.1%, 1%, 3%, 5%, 8 %, 10%, 15%, 18%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95% or 99%.
  • the agrochemically acceptable adjuvant includes any one or at least one of a dispersant, a wetting agent, an emulsifier, an antifreeze, a thickener, a defoamer, a preservative, a stabilizer, or a colorant. A combination of the two.
  • the dispersant includes lignin sulfonate, alkylphenol polyoxyethylene ether, naphthalenesulfonic acid formaldehyde condensate sodium salt, fatty amine polyoxyethylene ether, fatty acid polyoxyethylene ester, glycerin fatty acid ester polyoxylate Vinyl ether, polycarboxylate, formaldehyde condensate, calcium alkylbenzenesulfonate, alkylphenol polyoxyethylene ether.
  • the wetting agent is selected from the group consisting of sodium lauryl sulfate, alkyl naphthalene sulfonate, pulverized powder BX, polyoxyethylene ether, EO / PO block polyether, fatty alcohol polyoxyethylene ether, and fatty alcohol polyoxylate.
  • the emulsifier is selected from dodecylbenzenesulfonate, alkylnaphthalenesulfonate, alkylsulfonate, alkylphenol polyoxyethylene ether, benzylphenol polyoxyethylene, phenethylphenol polyoxyethylene Ether, fatty amine polyoxyethylene ether.
  • the antifreeze is selected from ethylene glycol, propylene glycol, and glycerol.
  • the thickener is selected from the group consisting of xanthan gum, hydroxymethyl cellulose, hydroxyethyl cellulose, hydroxypropyl starch, methyl cellulose, sodium starch phosphate, magnesium aluminum silicate, and polyvinyl alcohol.
  • the defoaming agent is selected from the group consisting of silicone oil, silicone compounds, tributyl phosphate, C10-C20 saturated fatty acid compounds, and polyether defoamers.
  • the preservative is selected from the group consisting of formaldehyde, phenyl salicylate, butyl parahydroxybenzoate, and potassium sorbate
  • the stabilizer is selected from triphenyl phosphite, epichlorohydrin, epoxy soybean oil, and silicic acid.
  • Magnesium aluminum, the colorant is selected from the group consisting of azo pigments, titanium oxide, and iron oxide.
  • the carrier includes a filler and / or a solvent
  • the agrochemically acceptable carrier includes a solid carrier and / or a liquid carrier.
  • the solid support includes natural or synthetic clays and silicates, such as natural silica and diatomaceous earth; magnesium silicates such as talc; magnesium aluminum silicates such as kaolinite, kaolin, montmorillonite, and mica; White carbon black, calcium carbonate, light calcium carbonate; calcium sulfate; limestone; sodium sulfate; amine salts such as ammonium sulfate and hexamethylene diamine.
  • Liquid carriers include water and organic solvents.
  • Organic solvents include aromatic hydrocarbons such as xylene, benzene, xylene, toluene, and the like; chlorinated hydrocarbons such as chlorobenzene, vinyl chloride, trichloromethane, and methylene chloride; Cyclohexane, light mineral oil; alcohols such as isopropanol, butanol, ethylene glycol, propylene glycol, glycerol, and cyclohexanol and their ethers and esters; ketones such as acetone, cyclohexanone, and dimethyl Formamide and N-methyl-pyrrolidone.
  • aromatic hydrocarbons such as xylene, benzene, xylene, toluene, and the like
  • chlorinated hydrocarbons such as chlorobenzene, vinyl chloride, trichloromethane, and methylene chloride
  • Cyclohexane light mineral oil
  • alcohols such as isopropanol, butan
  • the active ingredient may be mixed with a liquid carrier and / or a solid carrier, and auxiliary agents such as emulsifiers, dispersants, stabilizers, wetting agents, adhesives Mixtures, defoamers, antioxidants, etc.
  • auxiliary agents such as emulsifiers, dispersants, stabilizers, wetting agents, adhesives Mixtures, defoamers, antioxidants, etc.
  • the dosage form of the pharmaceutical preparation is a solution, a soluble powder, a soluble granule, an emulsifiable concentrate, a wettable powder, an aqueous emulsion, a suspending agent, a dispersible oil suspending agent, a water-dispersible granule, and a microcapsule suspending agent.
  • Granules, microemulsions, suspension emulsions, microcapsule suspension-suspensions ultra-low-volume liquids, hot aerosols, film-spreading oils, suspended seed coatings, dry powders for seeds, suspensions for seeds, and seeds for Powder dissolving agent, seed treatment dispersible powder, seed treatment emulsion or seed treatment liquid.
  • the dosage form of the pharmaceutical preparation is a solution, a soluble granule, a suspension, an emulsifiable concentrate, a wettable powder, an aqueous emulsion, a water-dispersible granule, a dispersible oil suspension, a microcapsule suspension, and an ultra-low capacity.
  • Liquid, hot aerosol, suspension seed coating or seed treatment dispersible powder is a solution, a soluble granule, a suspension, an emulsifiable concentrate, a wettable powder, an aqueous emulsion, a water-dispersible granule, a dispersible oil suspension, a microcapsule suspension, and an ultra-low capacity.
  • the present application provides the application of the pharmaceutical composition or pharmaceutical preparation containing the metadiamide compound as described above in the prevention, control of plant diseases or insect pests in agriculture, forestry, and horticulture.
  • the medicinal composition or medicinal preparation containing the metadiamide compound described in the present application is suitable for controlling various agricultural, forestry, horticultural pests and sanitary pests that harm rice, corn, wheat, potato, fruit trees, vegetables, other crops and flowers, and Disease.
  • the composition of the present application has a wide range of applications, and the scope of plants or crops to be applied mainly includes the following categories: vegetables, cucumbers, loofahs, watermelons, melon, pumpkins, hanging melon, spinach, celery, cabbage, cabbage, gourd, pepper, eggplant , Tomato, shallot, ginger, garlic, leek, strawberry, lettuce, kidney bean, cowpea, broad bean, radish, carrot, potato, yam; cereal, wheat, barley, corn, rice, sorghum; fruit tree, apple, pear, banana , Citrus, grape, lychee, mango; flowers, peony, rose, flamingo; oil crops, peanuts, soybeans, rape, sunflower, sesame; sugar crops, sugar beets, sugar cane; other crops, such as potatoes, sweet potatoes, tobacco and Tea; horticulture, forestry, home health, public health areas, etc .; the above-listed plants or crops have no limiting effect on the scope of use of the pharmaceutical
  • the pests include lepidoptera, coleoptera, hemiptera, tarptera, diptera, orthoptera, homoptera, isoptera, hymenoptera, and spider mite
  • said Diseases include diseases caused by semi-known bacteria, ascomycetes, basidiomycetes, and the like.
  • the pests include but are not limited to: cotton bollworm, diamondback moth, Spodoptera exigua, Spodoptera litura, Pieris rapae, diploid pupae, pupae trichoderma, big pupae, Spodoptera frugipera, rice leaf roller, rice Thrips, western flower thrips, melon thrips, onion thrips, ginger thrips, mango thrips, peach aphid, cotton aphid, alfalfa aphid, apple yellow aphid, wheat aphid, jumping beetle, stink bug, gray planthopper, Brown planthopper, white-backed planthopper, termite, mosquito fly, spider mite, citrus red spider.
  • the diseases include, but are not limited to, wheat scab, rice sheath blight, rice blast and the like.
  • the method of using the pharmaceutical composition or pharmaceutical preparation is spraying, soil treatment, seed treatment, flight prevention, and the like.
  • the present application provides the use of a pharmaceutical composition containing an m-bisamide compound as described above in seed treatment of plants, crops, or flowers.
  • the present application provides a method for controlling plant diseases and insect pests, which method is: applying an effective dose of the above-mentioned pharmaceutical composition containing metadiamide compounds to a plant disease to be controlled or a growth medium thereof Or pharmaceutical preparations.
  • the effective dose is 10-1000g per hectare, such as 10g, 20g, 50g, 80g, 100g, 120g, 150g, 180g, 200g, 250g, 300g, 350g, 400g, 450g, 500g, 600g, 700g, 800g 900g or 1000g, preferably 20-500g per hectare.
  • composition of the present application may be applied to the disease or its growth medium in the form of a formulation.
  • the compound of the general formula I (especially the compound of the general formula II) is dissolved or dispersed in a carrier as an active ingredient or formulated into a formulation for easier dispersion when used as a fungicide.
  • these chemical preparations can be formulated as solution, emulsifiable concentrate, wettable powder, water emulsion, suspension, dispersible oil suspension, water-dispersible granule, seed treatment, microcapsule suspension, granule, microemulsion , Suspension emulsion, suspension-microcapsule suspension and so on.
  • the pharmaceutical composition of the present application has the following advantages in use:
  • composition of active ingredient A and active ingredient B in this application has a synergistic effect.
  • the amount of the composition used is greatly reduced compared with the single active ingredient alone, and the control effect is significantly improved; due to the significant resistance of active ingredient A to resistant pests
  • the activity also solves the diseases and insect pests of important crops such as pupae, diamondback moth and other important crops.
  • the drug resistance can be delayed after compounding, which is an effective resistance risk management tool and extends the life cycle of the drug.
  • the active ingredient A and the active ingredient B described in the present application are compounded and combined to expand the control spectrum and save the labor cost of medicine. It can be applied to crops such as vegetables, fruit trees, flowers, cereals, oil, sugar, and horticulture, A variety of pests and diseases in forestry and health. In addition, it has extremely high activity against newly emerged Spodoptera frugiperda and can be used for emergency prevention and control, which is beneficial to maintaining environmental ecological safety and social stability.
  • Methyl 2-fluoro-3- (N- (cyclopropylmethyl) benzamide) benzoate (13.00 g, 40.88 mmol) was dissolved in methanol (100 mL), and a 10% aqueous sodium hydroxide solution (6.54 g) was added. , 163.52 mmol, 65.4 mL), after stirring at room temperature for 2 h, the reaction was monitored by TLC for completion. The methanol was concentrated and removed under reduced pressure. The concentrated residue was dissolved in water (100 mL) and extracted with ethyl acetate (50 mL). The organic phase was discarded, and the pH of the aqueous phase was adjusted to 7 with a 2M aqueous hydrochloric acid solution.
  • 2-Bromo-6-trifluoromethyl-4-heptafluoroisopropylaniline (0.52 g, 1.28 mmol) was dissolved in tetrahydrofuran (4 mL), and lithium diisopropylaminoamide (0.77 mL) was added dropwise at -70 ° C. , 1.54 mmol), 5 minutes later, a tetrafluorofuran solution of 2-fluoro-3- [N- (cyclopropylmethyl) benzamido] benzoyl chloride synthesized in one step was added dropwise, stirred at -70 ° C for 30 minutes, and raised to Stirring was continued for 30 min at room temperature.
  • a saturated ammonium chloride aqueous solution (20 mL) was added to the reaction solution, and the mixture was extracted with ethyl acetate (20 mL). The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure.
  • Methyl 2-fluoro-3-aminobenzoate (2.00 g, 11.82 mmol) was dissolved in 1,2-dichloroethane (65 mL), and cyclopropylmethyl ketone (2.98 g, 35.47 mmol) was sequentially added at room temperature. ), Trifluoroacetic acid (8.08 g, 70.92 mmol) and sodium triacetoxyborohydride (7.51 g, 35.47 mmol). The reaction was heated to 45 ° C. for 1 h. When TLC monitored that the reaction was no longer in progress, the reaction was terminated. A saturated NaHCO 3 solution (50 mL) was added to the reaction solution, and extracted with dichloromethane (80 mL).
  • composition of 10% compound 8 ⁇ flufluuron emulsion is shown in Table 5 below:
  • Preparation method Calculate the amount of each material according to the formula, add 200 # solvent oil to the batching kettle, and then add compound 8 and fluoremide to complete dissolution, then add calcium dodecylbenzenesulfonate and castor oil polyoxyethylene Ether was added, and the mixture was stirred at 40-50 ° C for 1.5 hours, and then filtered to obtain 10% compound 8 ⁇ fluronil emulsion.
  • Formulation Example 2 25% Compound 4
  • composition of the 25% compound 4 bupropion suspension seed coating agent is shown in Table 6 below:
  • Preparation method In the batching kettle, according to the proportion of the material, put in deionized water, compound 4, bupropion, FS3000, TER4894, Casson, SAG1522, propylene glycol and sand after shearing to control the particle size of D90 and about 5 microns Then, transfer it to the mixing kettle, add 2% xanthan gum solution, pigment F2R, and mix and stir for 1 hour to obtain 25% compound 4 ⁇ butylthiocarb Budweiser seed coating agent.
  • composition of the 35% compound 6 ⁇ tebufenozide water-dispersible granules is shown in Table 7 below:
  • Preparation method Calculate the amount of each material according to the formula, and mix compound 6, tebufenozide, sodium lauryl sulfate, sodium ligninsulfonate, sodium naphthalene formaldehyde polymer sulfonate, ammonium sulfate, corn starch, and kaolin. It is pulverized by an air jet mill to an average particle size of 10 to 15 microns, and 17% of the powder is added to knead. Then, it is granulated by rotary extrusion, dried at 50 ° C for 3 hours, and sieved to obtain 35% compound 6 ⁇ Insect dispersible granules.
  • Active ingredient A Permethrin 5 Active ingredient B Fatty alcohol polyoxyethylene ether 1.5 moisturizer Tristyryl phenol polyoxyethylene ether phosphate 2 Dispersant Sodium lignosulfonate 3 Dispersant Propylene glycol 4 antifreeze 1% xanthan gum solution 10 Thickener Casson 0.1 preservative Polydimethylsiloxane 0.2 Silicone defoamer Deionized water Make up 100 Carrier
  • Preparation method Calculate the amount of each material according to the formula, stir and dissolve the deionized water, propylene glycol, tristyryl phenol polyoxyethylene ether phosphate, sodium lignin sulfonate, carson, and defoamer, and add the ether permethrin Shear with compound 8 evenly, and then grind it to an average particle size of 2 microns with a sand mill. Add 10 parts of a 1% xanthan gum solution and stir for 30 minutes to obtain a 15% compound 8 ⁇ ethirthrin suspension.
  • composition of 5% compound 10 ⁇ cyhalothrin microcapsule suspension is shown in Table 9 below:
  • Preparation method Calculate the amount of each material according to the formula. Dissolve compound 10, lambda cyhalothrin, polyaryl polymethylene polyisocyanate, and xylene uniformly at 40-50 degrees as Phase A; Ionized water, D-800, propylene glycol, uniformly dissolve as Phase B; under high shear, slowly add Phase A to Phase B, cut to an average particle size of 2 to 3 microns, and then add the material to a three-necked flask.
  • composition of 25% Compound 6 ⁇ Avicin Wettable Powder is shown in Table 10 below:
  • Preparation method Calculate the amount of each material according to the formula, put compound 6, antipyramine, sodium dodecyl sulfate, sodium lignin sulfonate, kaolin in the batching kettle, mix them evenly, and then pulverize them to an average particle size with a jet mill. With a diameter of 10 microns, 25% of compound 6 ⁇ aphicarb-wettable powder was obtained.
  • Preparation method In a batching kettle, according to the process ratio, add No. 100 solvent oil and cyclohexanone, add compound 7, fluorooxazole amide with stirring, and heat to 50 ° C. After the solvent is completely added, add EL40 and fatty alcohol polyoxyethylene. Ether and SAG1522 were continued to stir for 10 minutes, and deionized water was added after the temperature was reduced to obtain 15% Compound 7 ⁇ Insecticidal monodisperse liquid solution.
  • Formulation agent 8 18% Compound 1 ⁇ Chlorpyrifos emulsion
  • composition of 18% Compound 1 ⁇ chlorpyrifos emulsion is shown in Table 12 below:
  • Preparation method In a batching kettle, first add solvent oil No. 150, then start stirring, add compound 1 and stir to dissolve. After the dissolution is complete, add chlorpyrifos and emulsifier TERMUL5030, continue stirring for 20 minutes, and mix until it is an oil phase. Put the deionized water, defoaming agent and antifreeze in the shear kettle, turn on the shearing device, and slowly add the oil phase material after 5 minutes, and then shear for 10 minutes after adding, to obtain 18% compound 1 ⁇ chlorpyrifos Water emulsion.
  • Bioassay Example 1 Active ingredient A is a compound of formula II, which has significant insecticidal activity against a variety of pests
  • Targets Plutella xylostella 3rd instar larvae, armyworm 3rd instar larvae, diploid pupae 3rd instar larvae, all reared indoors.
  • Plutella xylostella + leaf soaking feeding method With reference to NY / 1154.14-2008, the main operation description is as follows: immerse the clean bract leaf dish in the medicinal solution for 10s, dry it and place it in petri dishes, 4 dishes per dish, put filter paper in the petri dish to moisturize. Ten dishes of Plutella xylostella were received in each dish and repeated three times. It was placed in a light incubator at a temperature of 25 ° C under 14hL: 10hD and cultured. The number of dead and live insects of Plutella xylostella was investigated 3 days after the administration, and the mortality was calculated.
  • Feeding on slime + dipping leaf With reference to NY / 1154.14-2008, the main operation description is as follows: immerse the clean corn leaf section in the medicinal solution for 10s, dry it and place it in petri dishes, 4 pieces per dish, put filter paper in the petri dish to moisturize. Ten dishes of slimeworms were received in each dish, and 3 replicates were performed. It was placed in a light incubator at a temperature of 25 ° C under 14hL: 10hD and cultured. The number of dead and live insects of the armyworm was investigated 3 days after the administration, and the mortality was calculated.
  • Erhuan + rice stalk dipping method With reference to NY / T1154.11-2008, the main operation is as follows: immerse the cleaned rice stalks in the medicinal solution for 10s, remove them, place them in a cool place to dry, put them into finger tubes, and insert 10 third-instar larvae. Each treatment was repeated 3 times. The mouth of the tube was sealed with a black cotton cloth. The rubber band was tied tightly and placed in a light incubator at 28 ° C in the dark. The number of dead worms in P. chinensis was investigated 3 days after the treatment, and the mortality of each treatment was calculated.
  • Bioassay Example 2 The composition of active ingredient A is a compound of formula II and active ingredient B is chlorpyrifos, acephate, phoxim, dichlorvos, fenitrothion, promethan, triazophos, etc. Worm activity test
  • Target Myxosoma, 3rd instar larva
  • Soaking method Soaking method.
  • the operation description is as follows: With reference to NY / 1154.6-2006, the main operation description is as follows: immerse 10 test insects in the medicinal solution for 10s, dry them and place them in petri dishes, put 4 clean corn leaf sections in each dish, and petri dishes Put filter paper inside to moisturize. 3 repetitions. It was placed in a light incubator at a temperature of 25 ° C under 14hL: 10hD and cultured. The number of dead and live insects of the armyworm was investigated 3 days after the administration, and the mortality was calculated.
  • Theoretical mortality 1-(1-mortality of active ingredient A at this dose) (1-mortality of active ingredient B at this dose)
  • the synergistic effect is greater than 10, which indicates synergy, and greater than 20, which indicates significant synergy, is between -10 and 10, which indicates addition, and below -10, which indicates antagonism.
  • Test agent or combination name Dose mg / L 3d mortality% Theoretical mortality% Synergy effect Joint mode of action Compound 3 0.04 60 / / / Compound 5 0.04 53.33 / / / Compound 8 0.04 66.67 / / / Compound 10 0.04 80 / / / Profenfos 0.8 56.67 / / / Fenthion 2.5 43.33 / / / Phoxim 1.5 53.33 / / / Dichlorvos 1.5 50.00 / / / Chlorpyrifos 0.8 50 / / / Acephate 1.0 66.67 / / / Triazophos 0.8 46.67 / / / Compound 8+ chlorpyrifos 0.04 + 0.8 100 83.33 16.67 Synergy Compound 10+ chlorpyrifos 0.04 + 0.8 100 90.00 10.00 Synergy Compound 8+ acephate 0.04 + 1.0 100 88.89 11.
  • Bioassay Example 3 Active ingredient A is a compound of formula II and active ingredient B is an insecticide such as lambda-cyhalothrin, deltamethrin, cypermethrin, bifenthrin, permethrin, fenvalerate, etc. Composition, activity test on alfalfa aphid
  • Dipping method Dipping method. The operation is described as follows: Broad bean seedlings are cultivated indoors for aphids to feed. If aphids are prepared: 5 aphids are attached to the leaves of each broad bean, and after 24 hours, the aphids are removed. Before the test, the leaves with more than 15 aphids are selected for the test.
  • the treatment method is an immersion method: immerse the leaves (with aphids) in the medicinal solution for 10s, and repeat 3 times. Post-treatment culture and investigation: placed in a light incubator at 25 ° C, 14hL: 10hD, and cultured. The number of dead and live aphids was investigated 3 days after the administration, and the mortality was calculated.
  • the evaluation method was the same as that in Example 2.
  • Test agent or combination name Dose mg / L 3d mortality% Theoretical mortality% Synergy effect Joint mode of action Compound 6 10 57.77 / / / Compound 8 10 60.87 / / / Compound 11 10 53.33 / / / Lambda-cyhalothrin 0.4 51.11 / / / Deltamethrin 0.1 46.67 / / / Cypermethrin 2.0 55.56 / / / Bifenthrin 2.0 60.00 / / / / Fenpropathrin 4.0 57.77 / / / Permethrin 5.0 62.22 / / / Compound 8 + lambda-cyhalothrin 10 + 0.4 100 80.87 19.13 Synergy Compound 6 + deltamethrin 10 + 0.1 100 77.48 22.52 Significant synergy Compound 6 + cypermethrin 10 + 2.0 100 81.23 18.77
  • Bioassay Example 4 Composition of active ingredient A being a compound of formula II and active ingredient B being isoprocarb, metronidazole, bufacarb, aphicarb-resistant, etc., for testing activity against brown planthoppers
  • Target Brown planthopper, 3rd instar nymph.
  • the evaluation method is the same as the standard test example 2.
  • Test agent or combination name Dose mg / L 3d mortality% Theoretical mortality% Synergy effect Joint mode of action Compound 1 10 60.00 / / / Compound 2 10 51.11 / / / Compound 4 6 55.55 / / / Compound 8 10 71.11 / / /
  • Bioassay Example 5 Active ingredient A is a compound of formula II and active ingredient B is a combination of insecticidal single, insecticidal double, insecticidal ring, and phoxim
  • Target 3rd instar larvae of pupae, indoor breeding.
  • Test agent or combination name Dose mg / L 3d mortality% Theoretical mortality% Synergy effect Joint mode of action Compound 4 0.4 53.33 / / / Compound 5 1.0 63.33 / / / Compound 6 1.00 56.67 / / / Compound 7 0.5 50.00 / / / Compound 8 0.5 56.67 / / / Compound 9 1.0 66.67 / / / Compound 10 0.5 33.33 / / / Compound 11 1.25 76.67 / / / Compound 12 1.0 56.67 / / / Compound 13 0.5 33.33 Zh Zh Zh Insecticide 80 56.67 / / / Insecticide double 80 60 / / / Insecticidal ring 80 56.67 / / / Carbendam 100 63.33 / / Compound 4+ Insecticidal 0.4 + 80 100 79.78 20.22 Significant
  • Bioassay Example 6 Activity test on armyworm when the active ingredient A is a compound of formula II and the active ingredient B is diflubenzuron, halofuron, and tebufenozide
  • Target Myxosoma, 3rd instar larva
  • Test agent or combination name Dose mg / L 3d mortality% Theoretical mortality% Synergy effect Joint mode of action Compound 3 0.04 60.00 / / / Compound 5 0.04 73.33 / / / Diflubenzuron 2.0 46.67 / / / Fluoremide 0.8 50.00 / / / Tebufenozide 1.2 60.00 / / / Compound 3+ Diflubenzuron 0.04 + 2.0 100 78.67 21.33 Significant synergy Compound 3 + flumuron 0.04 + 0.8 100 80.00 20.00 Significant synergy Compound 5+ tebufenozide 0.04 + 1.0 100 89.33 10.67 Synergy
  • Bioassay Example 7 Test of the activity of the compound 4 and insecticidal compound on pupae
  • Insect source 3rd instar larvae of pupae, indoor breeding.
  • Example 1 Rice stalk immersion method, the operation description is described in Example 1.
  • the evaluation method refers to NY / T1154.7-2006, and the co-toxicity coefficient is used for evaluation.
  • the co-toxicity coefficient (CTC value) of the mixture is calculated according to formula (1), formula (2), and formula (3):
  • TTI A ⁇ P A + B ⁇ P B ⁇ ⁇ (2)
  • CTC co-toxicity coefficient
  • ATI mixed actual virulence index
  • TTI mixed theoretical virulence index
  • Co-toxicity coefficient (CTC) ⁇ 120 is synergistic; CTC ⁇ 80 is antagonistic; 80 ⁇ CTC ⁇ 120 is additive.
  • Bioassay Example 8 Activity test of a combination of compound 8 and chlorpyrifos against pupae
  • Insect source 3rd instar larvae of pupae, indoor breeding.
  • Bioassay Example 9 Activity test of a composition of compound 7 and isoprocarb against brown planthopper
  • Target Brown planthopper, 3rd instar nymph.
  • Bioassay Example 10 Activity Test of a Composition of Compound 1 and Diflubenzuron against Diamondback Moth
  • Insect source Plutella xylostella 3rd instar larvae, reared indoors.
  • Both Compound 1 and Diflubenzuron have good activity against Plutella xylostella; Compound 1 and Diflubenzuron have a co-toxicity coefficient of 102.51 ⁇ 251.14 in a ratio of 160: 1 to 1: 160, showing an additive or synergistic effect. ; The co-toxicity coefficients were all greater than 120 when the ratio was 80: 1 to 1:80, showing a synergistic effect.
  • Bioassay Example 11 Activity test of a combination of compound 7 and lambda-cyhalothrin against aphid
  • Insect source Alfalfa aphids 3 days old if aphids, indoor breeding.
  • Bioassay Example 12 Test of the activity of a combination of compound 6 and chlorpyrifos against Liriomyza sativae
  • Insect source Liriomyza sativae, reared indoors.
  • Leaf impregnation method with reference to NY / 1154.14-2008, the main operation description is as follows: immerse clean rainbow bean leaves in the medicinal solution for 10s, dry them and place them in petri dishes, 1 piece per dish, put filter paper in the dish to moisturize . Ten larvae of Liriomyza spp. Were received in each dish and repeated three times. It was placed in a light incubator at a temperature of 25 ° C under 14hL: 10hD and cultured. The number of dead live insects was investigated 3 days after the treatment, and the mortality was calculated.
  • the evaluation method was the same as that in Example 7.
  • Bioassay Example 13 Activity test of a composition of compound 14 and picropropyl ether against Bemisia tabaci
  • Insect source Bemisia tabaci
  • greenhouse breeding crop: eggplant.
  • the glass tube medicine film method referring to NY / 1154.14-2008, the main operation description is as follows: the drug is combined with the glass tube to form a drug film, each tube receives 10 adults of Bemisia tabaci and repeats 4 times. It was placed in a light incubator at a temperature of 25 ° C under 14hL: 10hD and cultured. The number of dead and alive insects was checked at 8h after the treatment, and the mortality was calculated.
  • the evaluation method was the same as that in Example 7.

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Abstract

La présente invention concerne une composition médicamenteuse contenant un composé M-diamide et l'application de la composition médicamenteuse. La composition médicamenteuse comprend un constituant efficace A et un constituant efficace B ; le constituant efficace A est le composé M-diamide ayant une structure présentée selon la formule I, et le constituant efficace B comprend n'importe lequel ou des combinaisons de deux autres insecticides. La composition contenant le constituant efficace A et le constituant efficace B présente des fonctions uniques telles que l'effet de synergie, la régulation des ravageurs résistants, l'expansion d'un spectre d'activités, et la régulation des insectes de dissémination de virus, et peut efficacement réguler de multiples maladies et ravageurs sur les cultures telles que le riz, le maïs, le blé, les légumes, les arbres fruitiers, les fleurs, les plantes oléagineuses, et les plantes sucrières, et horticoles et de foresterie.
PCT/CN2019/099952 2018-08-10 2019-08-09 Composition médicamenteuse contenant le composé m-diamide et application de la composition médicamenteuse WO2020030096A1 (fr)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101208009A (zh) * 2005-07-27 2008-06-25 三井化学株式会社 有害生物防除组合物
CN102119143A (zh) * 2008-08-13 2011-07-06 三井化学Agro株式会社 酰胺衍生物、含有该酰胺衍生物的有害生物防除剂及其使用方法
JP2011157294A (ja) * 2010-01-29 2011-08-18 Mitsui Chemicals Agro Inc 有害生物防除組成物
CN108586279A (zh) * 2018-06-26 2018-09-28 上海泰禾国际贸易有限公司 一种间二酰胺类化合物及其制备方法和应用

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108294000A (zh) * 2018-02-07 2018-07-20 湖南泽丰农化有限公司 一种含溴虫氟苯双酰胺和甲氧虫酰肼的杀虫组合物

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101208009A (zh) * 2005-07-27 2008-06-25 三井化学株式会社 有害生物防除组合物
CN102119143A (zh) * 2008-08-13 2011-07-06 三井化学Agro株式会社 酰胺衍生物、含有该酰胺衍生物的有害生物防除剂及其使用方法
JP2011157294A (ja) * 2010-01-29 2011-08-18 Mitsui Chemicals Agro Inc 有害生物防除組成物
CN108586279A (zh) * 2018-06-26 2018-09-28 上海泰禾国际贸易有限公司 一种间二酰胺类化合物及其制备方法和应用

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