WO2021036965A1 - 一种间苯二甲酰胺类化合物及其应用 - Google Patents
一种间苯二甲酰胺类化合物及其应用 Download PDFInfo
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- WO2021036965A1 WO2021036965A1 PCT/CN2020/110706 CN2020110706W WO2021036965A1 WO 2021036965 A1 WO2021036965 A1 WO 2021036965A1 CN 2020110706 W CN2020110706 W CN 2020110706W WO 2021036965 A1 WO2021036965 A1 WO 2021036965A1
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- isophthalamide
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- 0 Nc1cccc(C(*c2c(C(F)(F)F)cc(C(C(F)(F)F)(C(F)(F)F)F)cc2Br)=O)c1F Chemical compound Nc1cccc(C(*c2c(C(F)(F)F)cc(C(C(F)(F)F)(C(F)(F)F)F)cc2Br)=O)c1F 0.000 description 3
- PFCOYRFLVCQQHE-UHFFFAOYSA-N N#CCCCNc(cccc1C(Nc2c(C(F)(F)F)cc(C(C(F)(F)F)(C(F)(F)F)F)cc2[Tl])=O)c1F Chemical compound N#CCCCNc(cccc1C(Nc2c(C(F)(F)F)cc(C(C(F)(F)F)(C(F)(F)F)F)cc2[Tl])=O)c1F PFCOYRFLVCQQHE-UHFFFAOYSA-N 0.000 description 1
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- 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
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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
- A01N37/18—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
- A01N37/22—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 the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
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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
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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
- 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
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P7/00—Arthropodicides
- A01P7/04—Insecticides
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
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- 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
- C07C237/40—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 the nitrogen atom of the carboxamide group bound to a carbon atom of a six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/42—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being further bound to other hetero atoms
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- 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
- C07C255/57—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and carboxyl groups, other than cyano groups, bound to the carbon skeleton
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- 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
- C07D213/06—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
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- 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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/26—Radicals substituted by halogen atoms or nitro radicals
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- 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Definitions
- the invention relates to a compound, in particular to a novel isophthalamide compound and its application.
- Patent CN102112437A discloses compound CK1 (Compound No. 5-108), which has insecticidal activity.
- the object of the present invention is to provide an isophthalamide compound with excellent insecticidal activity. It can be used to prepare drugs for controlling pests in agriculture and other fields, and for preparing drugs for controlling animal parasites in the field of veterinary medicine.
- the present invention provides the following technical solutions:
- R 1 is selected from halogen
- R 2 is selected from halogen, C 1 -C 4 haloalkyl or C 1 -C 4 haloalkoxy;
- R 3 is selected from CF 3 or CF 2 CF 3 ;
- R 4 is selected from cyano C 1 -C 4 alkyl
- R 5 is selected from fluorine, difluoromethyl or trifluoromethyl.
- R 1 is selected from halogen
- R 2 is selected from halogen, C 1 -C 2 haloalkyl or C 1 -C 2 haloalkoxy;
- R 3 is selected from CF 3 or CF 2 CF 3 ;
- R 4 is selected from cyano C 1 -C 4 alkyl
- R 5 is selected from fluorine, difluoromethyl or trifluoromethyl.
- R 1 is selected from bromine or iodine
- R 2 is selected from bromine, iodine, trifluoromethyl or difluoromethoxy
- R 3 is selected from CF 3 or CF 2 CF 3 ;
- R 4 is selected from CH 2 CN, CH 2 CH 2 CN, CH 2 CH 2 CH 2 CN, CH 2 CH 2 CH 2 CH 2 CN, CH(CH 3 )CN, CH(CH 2 CH 3 )CN, CH( CH 2 CH 2 CH 3 )CN, C(CH 3 )(CH 3 )CN or C(CH 3 )(CH 2 CH 3 )CN;
- R 5 is selected from fluorine, difluoromethyl or trifluoromethyl.
- R 1 is selected from bromine or iodine
- R 2 is selected from bromine, iodine or trifluoromethyl
- R 3 is selected from CF 3 ;
- R 4 is selected from CH 2 CN, CH 2 CH 2 CN, CH 2 CH 2 CH 2 CN or CH 2 CH 2 CH 2 CH 2 CN;
- R 5 is selected from fluorine or trifluoromethyl.
- the isophthalamide compound is selected from the compound of Table 1, and the compound of Table 1 has the structure of Formula I and R 1 , R 2 , R 3 , R 4 and R 5 are as As shown in Table 1:
- the isophthalamide compound is selected from the compounds in Table 2, and the compounds in Table 2 have the structure of Formula I and R 1 , R 2 , R 3 , R 4 and R 5 are as As shown in Table 2:
- R 1 is selected from halogen
- R 2 is selected from halogen, C 1 -C 4 haloalkyl or C 1 -C 4 haloalkoxy;
- R 3 is selected from CF 3 or CF 2 CF 3 ;
- R 4 is selected from cyano C 1 -C 4 alkyl.
- R 1 is selected from halogen
- R 2 is selected from halogen, C 1 -C 2 haloalkyl or C 1 -C 2 haloalkoxy;
- R 3 is selected from CF 3 or CF 2 CF 3 ;
- R 4 is selected from cyano C 1 -C 4 alkyl.
- R 1 is selected from bromine or iodine
- R 2 is selected from bromine, iodine, trifluoromethyl or difluoromethoxy
- R 3 is selected from CF 3 or CF 2 CF 3 ;
- R 4 is selected from CH 2 CN, CH 2 CH 2 CN, CH 2 CH 2 CH 2 CN, CH 2 CH 2 CH 2 CH 2 CN, CH(CH 3 )CN, CH(CH 2 CH 3 )CN, CH( CH 2 CH 2 CH 3 )CN, C(CH 3 )(CH 3 )CN or C(CH 3 )(CH 2 CH 3 )CN.
- R 1 is selected from bromine or iodine
- R 2 is selected from bromine, iodine or trifluoromethyl
- R 3 is selected from CF 3 ;
- R 4 is selected from CH 2 CN, CH 2 CH 2 CN, CH 2 CH 2 CH 2 CN, or CH 2 CH 2 CH 2 CH 2 CN.
- the intermediate compound is selected from the compound of Table 3, and the compound of Table 3 has the structure of Formula II and R 1 , R 2 , R 3 and R 4 are as shown in Table 3:
- R 4 is selected from cyano C 1 -C 4 alkyl
- R 5 is selected from fluorine, difluoromethyl or trifluoromethyl
- L is selected from halogen or hydroxyl.
- R 4 is selected from CH 2 CN, CH 2 CH 2 CN, CH 2 CH 2 CH 2 CN, CH 2 CH 2 CH 2 CH 2 CN, CH(CH 3 )CN, CH(CH 2 CH 3 )CN, CH( CH 2 CH 2 CH 3 )CN, C(CH 3 )(CH 3 )CN or C(CH 3 )(CH 2 CH 3 )CN;
- R 5 is selected from fluorine, difluoromethyl or trifluoromethyl
- L is selected from halogen or hydroxyl.
- the intermediate compound is selected from the compound of Table 4, and the compound of Table 4 has the structure of Formula III and R 4 , R 5 and L are as shown in Table 4:
- the compound of the general formula IV and the halogenated compound R 4 -LG are reacted in a suitable solvent at a temperature from -10°C to the boiling point of the solvent for 0.5-48 hours to obtain a compound of the general formula II.
- the reaction is carried out in the presence of a base and a catalyst;
- the compound of formula II and the compound of general formula V are reacted in a suitable solvent at a temperature from -10°C to the boiling point of the solvent for 0.5-48 hours to obtain a compound of general formula I.
- the reaction can be carried out in the presence of a base and a catalyst.
- Suitable solvents in the above steps can be the same or different.
- Aromatic hydrocarbons such as benzene, toluene and xylene; ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone; halogenated hydrocarbons such as chloroform and dichloromethane; and methyl acetate.
- the bases that can be the same or different are organic bases such as triethylamine, pyridine, DBU, 4-dimethylaminopyridine, alkali metal hydrides such as sodium hydride, potassium hydride, and alkali metals such as sodium hydroxide and potassium hydroxide.
- the catalysts in each of the above steps may be the same or different: potassium iodide, sodium iodide, potassium fluoride, sodium fluoride, potassium bromide or sodium bromide.
- the compound of general formula IV can be prepared according to known methods, for example, with reference to WO20110201687, WO2011093415, WO2005021488, WO2005073165, WO2006137395, JP2007099761, WO2008000438, WO2008074427, WO2008107091, WO2010013567, WO2010018714, WO2010090282, WO2010127926, WO2010127928, JP20112012549, WO2014842012483, 077, WO201484 WO2013050261, WO2014069665, WO2014067838, WO2014161848, WO2014161850, WO2015097091 or the like prepared by methods reported in WO2015097094; halide R 4 -LG, compounds of formula V and a base are usually commercially available, can also be made in a conventional manner.
- 3-amino-2-fluorobenzoic acid methyl ester and halogenated compound R 4 -LG are reacted in a suitable solvent at a temperature from -10°C to the boiling point of the solvent for 0.5-48 hours to obtain a compound of general formula VI.
- the reaction can be carried out at Carry out in the presence of a base; the compound of formula VI and the compound of formula V are reacted in a suitable solvent at a temperature from -10°C to the boiling point of the solvent for 0.5-48 hours to obtain a compound of formula VII.
- the reaction can be carried out in the presence of a base. .
- suitable solvents can be aromatic hydrocarbons such as benzene, toluene and xylene; ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone; halogenated hydrocarbons such as chloroform and dichloromethane; methyl acetate and ethyl acetate.
- aromatic hydrocarbons such as benzene, toluene and xylene
- ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone
- halogenated hydrocarbons such as chloroform and dichloromethane
- bases can be organic bases such as triethylamine, pyridine, DBU, 4-dimethylaminopyridine, alkali metal hydrides such as sodium hydride, potassium hydride, sodium hydroxide , Alkali metal hydroxides such as potassium hydroxide, alkaline earth metal hydroxides such as calcium hydroxide, alkali metal carbonates such as sodium carbonate and potassium carbonate, alkali metal bicarbonates such as sodium bicarbonate, sodium methoxide, sodium ethoxide, Metal alkoxides such as potassium ethoxide, potassium tert-butoxide, and sodium tert-butoxide
- Compounds of general formula VII can be hydrolyzed to prepare compounds of general formula III-1 in the presence of alkaline substances at a temperature from -10°C to the boiling point of the solvent for 0.5-48 hours;
- suitable bases can be lithium hydroxide, sodium hydroxide or Potassium hydroxide,
- a suitable solvent can be any one or a mixed solvent of at least two of water, methanol, ethanol, tetrahydrofuran or dioxane.
- the compound of general formula III-1 can be prepared by reacting compound of general formula III-1 with thionyl chloride, oxalyl chloride, phosgene, phosphorus oxychloride, phosphorus pentachloride, phosphorus trichloride, triphosgene, etc. by using a known method.
- a compound of general formula III-1 or a compound of general formula III-2 and a compound of general formula VIII can be reacted in a suitable solvent at a temperature from -70°C to the boiling point of the solvent for 0.5-48 hours to obtain a compound of general formula I.
- the reaction can be carried out in Carry out in the presence of alkali;
- suitable solvents can be aromatic hydrocarbons such as benzene, toluene and xylene; ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone; halogenated hydrocarbons such as chloroform and dichloromethane; methyl acetate and acetic acid Esters such as ethyl ester, ethers such as tetrahydrofuran, dioxane, diethyl ether, 1,2-dimethoxyethane, water, acetonitrile, N,N-dimethylformamide, N-methylpyrrolidone, two Polar solvents such as methyl sulfoxide or a mixed solvent of the above solvents,
- the base can be trimethylamine, triethylamine, diisopropylethylamine, tri-n-butylamine, pyridine, DBU, 4-di
- the embodiments of the present invention also provide the use of the above isophthalamide compounds in the preparation of insecticides.
- the insecticide is used to control one or more of the following insects:
- Lepidopteran pests for example, Lymantria dispar, Malacosoma neustria, Pieris rapae crucivola, Spodoptera litura, Maestra brassicae), Chilo suppressalis, European corn borer (Ostrinia nubilalis), Cadra cautella, chyanokokakumonhamaki (Adoxophyes honmai), Cydia pomonella, Agrotis segetum, Galleria mellonella, Plutella xylostella, Heliothis virescens, Phyllocnistis citrella;
- Hemipterous pests such as Nephotettix cincticeps, Nilaparvata lugens, Pseudococcuscomstocki, Unaspis yanonensis, Myzus persicas, Apple aphid (Aphis pomi), cotton aphid (Aphis gossypii), radish aphid (Lipaphis erysimi), pear crown bug (Stephanitis nashi), green stink (Nezara spp.), greenhouse whitefly (Trialeurodes vaporariorum), Pshylla spp. ;
- Thysanoptera pests, such as palm thrips (Thrips palmi), western flower thrips (Franklinella occidentalis);
- Orthopteran pests such as Gryllotalpa Africana and Locusta migratoria
- Blattarian pests such as German cockroach (Blattella germanica), American cockroach (Periplaneta americana), yellow-breasted termites (Reticulitermes spermus), house termites (Coptotermes formosanus)
- Dipterous pests such as Musca domestica, Aedesaegypti, Delia platura, Culex pipiens pallens, Anopheles sinensis, Three Culex tritaeniorhynchus, Liriomyza trifolii, etc.
- Agricultural pest mites such as Tetranychus cinnabarinus, Tetrahychus urticae, Panonychus citri, Aculops pelekassi, Tarsonemus spp., etc. .
- the insecticide is used to control one or more of Armyworm, Plutella xylostella, and Chilo suppressalis.
- the embodiment of the present invention also provides an insecticide formulation, which contains the above isophthalamide compound as an active component, and also contains one or more auxiliary materials.
- the insecticide preparation is selected from the following dosage forms: solution, emulsion, wettable powder, granular wettable powder, suspension, powder, foam, ointment, tablet, granule Agents, aerosols, natural agents impregnated with active compounds, synthetic agents impregnated with active compounds, microcapsules, seed coatings, preparations equipped with a combustion device (the combustion device may be a chimney, a mist tube, a pot And coils, etc.) and ULV (cold mist, hot mist) and so on.
- a combustion device may be a chimney, a mist tube, a pot And coils, etc.
- ULV cold mist, hot mist
- insecticide preparations or animal parasite control agents can be prepared by known methods, for example, by combining the active ingredients with fillers (such as liquid diluents or carriers, liquefied gas diluents or carriers, solid diluents or carriers) It is prepared by mixing, and optionally with surfactants (ie, emulsifiers and/or dispersants and/or foaming agents) and the like.
- fillers such as liquid diluents or carriers, liquefied gas diluents or carriers, solid diluents or carriers
- surfactants ie, emulsifiers and/or dispersants and/or foaming agents
- the auxiliary material includes one or more of the following: filler (such as: liquid diluent or carrier, liquefied gas diluent or carrier, solid diluent or carrier), surfactant (such as: emulsifier and/or dispersant and/or foaming agent), adhesive, colorant;
- filler such as: liquid diluent or carrier, liquefied gas diluent or carrier, solid diluent or carrier
- surfactant such as: emulsifier and/or dispersant and/or foaming agent
- adhesive such as: emulsifier and/or dispersant and/or foaming agent
- the liquid diluent or carrier may include, for example, aromatic hydrocarbons (xylene, toluene, alkyl naphthalene, etc.), chlorinated aromatic hydrocarbons or chlorinated aliphatic hydrocarbons (such as chlorobenzene, vinyl chloride, methylene chloride, etc.), aliphatic hydrocarbons (Such as cyclohexane or paraffin wax (such as mineral oil fraction)), alcohol (such as butanol, ethylene glycol, and ether or ester thereof), ketone (such as acetone, methyl ethyl ketone, methyl isobutyl ketone) , Cyclohexanone, etc.), strong polar solvents (such as dimethyl formamide, dimethyl sulfoxide), water, etc.
- aromatic hydrocarbons xylene, toluene, alkyl naphthalene, etc.
- chlorinated aromatic hydrocarbons or chlorinated aliphatic hydrocarbons such
- Liquefied gas diluents or carriers may include those that exist in gaseous form at atmospheric pressure and temperature, for example, propane, nitrogen, carbon dioxide, and aerosol propellants such as halogenated hydrocarbons;
- the solid diluent may include crushed natural minerals (such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, etc.) and crushed synthetic minerals (such as finely divided silicic acid, alumina And silicate etc.) etc.;
- crushed natural minerals such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, etc.
- crushed synthetic minerals such as finely divided silicic acid, alumina And silicate etc.
- Emulsifiers and/or foaming agents may include nonionic and anionic emulsifiers [e.g., polyoxyethylene fatty acid esters, polyoxyethylene fatty acid alcohol ethers (such as alkyl aryl polyethylene glycol ethers), alkyl sulfonates , Alkyl sulfate and aryl sulfonate] and albumin hydrolysate, etc.;
- nonionic and anionic emulsifiers e.g., polyoxyethylene fatty acid esters, polyoxyethylene fatty acid alcohol ethers (such as alkyl aryl polyethylene glycol ethers), alkyl sulfonates , Alkyl sulfate and aryl sulfonate] and albumin hydrolysate, etc.;
- the dispersant may include lignin sulfite waste liquid and methyl cellulose;
- the binder may include carboxymethyl cellulose, natural or synthetic polymers (for example, gum arabic, polyvinyl alcohol, polyvinyl acetate, etc.).
- the colorant may include inorganic pigments (such as iron oxide, titanium oxide, and Prussian blue, etc.), organic dyes such as alizarin dyes, azo dyes, or metal phthalocyanine dyes; and trace elements such as iron salts, manganese salts, boron salts, copper Salt, cobalt salt, molybdenum salt or zinc salt.
- inorganic pigments such as iron oxide, titanium oxide, and Prussian blue, etc.
- organic dyes such as alizarin dyes, azo dyes, or metal phthalocyanine dyes
- trace elements such as iron salts, manganese salts, boron salts, copper Salt, cobalt salt, molybdenum salt or zinc salt.
- the amount of the isophthalamide compound contained in the pesticide formulation is 0.1 to 99% by weight, optionally 0.5 to 90% by weight.
- the embodiments of the present invention also provide an insecticide composition, which includes the above isophthalamide compound and other active compounds (such as insecticides, baits, disinfectants, acaricides, nematicides, and pesticides). Fungal agents, growth regulators, herbicides, etc.) mixtures.
- the mixture may be provided in the form of a bulk drug, or may be provided in the form of a commercially available useful preparation or a use form prepared from its preparation.
- the embodiment of the present invention also provides a method for controlling agricultural or forestry pests, which includes the following steps: applying an effective dose of materials to the pests to be controlled or their growth medium, and the materials are selected from one of the following groups Or more: the above-mentioned isophthalamide compounds, the above-mentioned insecticide preparation, and the above-mentioned insecticide composition.
- the embodiments of the present invention also provide the use of the above isophthalamide compounds in the preparation of animal parasite control agents.
- the isophthalamide compound of the present invention can be effectively used to combat a variety of harmful animal parasites, especially endoparasites and ectoparasites.
- animal parasites include one or more of the following:
- Anoplurida such as Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp, and Solenopotes spp.; in particular, representative examples Yes, Linognathus setosus, Solenopotes capillatus;
- Trichophagous order (Mallopha, Linognathus vituli), sheep jaw lice (Linognathus ovillus), Linognathus oviformis, foot jaw lice (Linognathus pedalis), goat jaw lice (Linognathus stenopsis), donkey blood lice (Haematopinus asini, macrocephalus) Bovine blood louse (Haematopinus eurysternus), pig blood louse (Haematopinus suis), head louse (Pediculus humanus capitis), body louse (Pediculus humanus corporis), grape phylloxera (Phylloera vastatrix), pubic louse (Phthirus pubis) gida) Amblycerina and Ischnocerin, for example, Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp.), Werneckiella spp., Lepi
- Bovicola bovis bovine lice
- wool louse Bovicola ovis
- Angola goat feather louse Bovicola limbata
- cattle louse Damalina bovis
- dog hair louse Trichodectes canis
- cat feather louse Felicola subrostratus
- goat louse Bovicola caprae
- Diptera and its Nematocerina and Brachycerina for example, Aedes spp., Anopheles spp., Culex spp .), Simulium spp, Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Spotted fly ( Chrysops spp.), Odagmia spp., Wilhelmia spp., Hybomitra spp., Atylotus spp., Tabanus spp., Hemp Haematopota (Haematopota spp.), Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp.
- Lucilia spp. Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Stomach Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp., Rhinoestrus spp., Crane spp. Tipula spp.);
- representative examples include Aedes aegypti, Aedes albopictus, Aedes taeniorhynchus, Anopheles gambiae, and Aedes albopictus.
- Mosquitoes (Anopheles maculipennis), Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefascia tus), Culex pipiens, Culex tarsalis, Fannia canicularis, Sarcophaga carnaria, Stomoxys calcitrans, Tipula paludosa ), Lucilia cuprina, Lucilia sericata, Simulium reptans, Phlebotomus papatasi, Phlebotomus longipalpis, Odagmia ornata, Wilhelmia equina, Boophthora erythrocephala, Tabanus bromius, Tabanus spodopterus, Tabanus atratus, Tabanus sudeticus Hybomitra ciurea, Chrysops caecutiens, Chrysops relictus, Haematopota pluvialis, Haemat
- Siphonaptrida for example, Pulex spp., Ctenocephalides spp., Tunga spp., Xenopsylla spp., Ceratophyllus spp.);
- representative examples include Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, and Ctenocephalides canis (Xenopsylla cheopis);
- Acari or Acarina
- Metastigmata and Mesostigmata for example, Argas spp., Ornithodorus spp., Remnant beak tick Otobius spp., Ixodes spp., Amblyomma spp., Rhipicephalus (Boophilus) spp., Dermacentor spp., Haemophysalis spp., Hyalomma (Hyalomma spp.), Dermanyssus spp., Rhipicephalus spp.
- Acarapis spp. include Argas persicus, Argas reflexus, Ornithodorus moubata, and ear damage Otobius megnini, Rhipicephalus (Boophilus) microplus, Rhipicephalus (Boophilus) decoloratus, Rhipicephalus (Boophilus) decoloratus), Rhipicephalus (Boophilus) decoloratus Rhipicephalus (Boophilus) annulatus), Rhipicephalus (Boophilus) calceratus, Hyalomma anatolicum, Hyalomma aegypticum, Hyalomamarginatum, Hyalomma transiens, Eversion Rhipicephalusevertsi, Ixodes ricinus, Ixodes hexagonus, Ixodes canisuga, Ixodes canisuga, Ixodes pilosus, Ixodes rubicu ndus), Ixodes
- Rhipicephalus capensis Rhipicephalus turanicus
- Rhipicephalus zambeziensis Amblyomma americanum, Amblyomma variegatum, Amblyomma maculatumh, Emblyomma maculatumh , Amblyomma cajennense, Dermanyssus gallinae, Ornithonyssus bursa, Ornithonyssus sylviarum, Varroa jacobsconi;
- Actinedida Prostigmata
- Acaridida Acaridida
- Acarapis spp. Cheyletiella spp.
- Ornitrocheyletia spp. Ornitrocheyletia spp.
- Myobia spp. Psorergates spp.
- Demodex spp. Trombicula spp.
- Nematodes such as Meloidogyne incognita, Bursaphelenchus xylophilus, Aphelenchoides besseyi, Heterodera glycines, Pratylenchus spp., etc.;
- Arthropods, worms and malaria parasites that invade animals. Controlling arthropods, worms and/or malaria parasites can reduce the mortality of domestic animals and improve the productivity (meat, milk, hair, skin, eggs and honey) and health of animals.
- the animal parasite control agent is used to control one or more of cat fleas and American dog ticks.
- the animals include one or more of the following: agricultural animals, such as cows, sheep, goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese , Farmed fish, bees, etc.; also includes pets called companion animals, such as dogs, cats, caged birds, and ornamental fish; also includes animals used for experiments, such as hamsters, guinea pigs, rats, and mice.
- agricultural animals such as cows, sheep, goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese , Farmed fish, bees, etc.
- companion animals such as dogs, cats, caged birds, and ornamental fish
- animals used for experiments such as hamsters, guinea pigs, rats, and mice.
- the embodiment of the present invention also provides an animal parasite control agent, which contains the above isophthalamide compound as an active component, and also contains one or more auxiliary materials.
- the animal parasite control agent is selected from the following dosage forms: tablets, capsules, drinks, drinkable drugs, granules, ointments and pills, suppositories, injections (muscle, subcutaneous, intravenous, Intraperitoneal, etc.), smears, aerosols, non-pressure sprays (such as pump sprays and atomized sprays).
- the amount of the above-mentioned active component contained in the animal parasite control agent is 1 to 80% by weight.
- the embodiment of the present invention also provides an animal parasite control composition, which includes the above isophthalamide compound and other animal parasite control active compounds (such as acaricides, insecticides, parasites, anti- Plasmodium agents, etc.) mixtures.
- the mixture may be provided in the form of a bulk drug, or may be provided in the form of a commercially available useful preparation or a use form prepared from its preparation.
- the embodiment of the present invention also provides a method for controlling animal parasites, which includes the following steps: applying an effective dose of material to the animal parasites or their growth medium to be controlled, and the material is selected from one of the following group: One or more: the above-mentioned isophthalamide compounds; the above-mentioned animal parasite control agent; the above-mentioned animal parasite control composition.
- suppositories for enteral administration; skin-based non-intestinal administration, such as injection (muscle, subcutaneous, intravenous, Intraperitoneal, etc.), implantation, nasal administration, including bathing or soaking, spraying, pouring, dripping, washing and dusting, and through the use of model products containing active compounds, such as collars, ear tags, labels, legs Use leg brace, net, marker, etc.
- the active compound of the present invention has low toxicity and can be safely used in warm-blooded animals.
- the isophthalamide compounds of the present invention have unexpectedly excellent insecticidal effects, they also exhibit suitable control effects against toxic pests, and are not phytotoxic to cultivated crop plants.
- the compounds of the present invention can be used to control various pests, such as harmful sucking insects, chewing insects, and other plant parasitic pests, stored grain pests, sanitary pests, etc., and can be used to disinfect and kill them.
- Halogen refers to fluorine, chlorine, bromine or iodine.
- Halogenated alkyl groups straight or branched chain alkyl groups.
- the hydrogen atoms on these alkyl groups can be partially or completely replaced by halogens, such as difluoromethyl (CHF 2 ), trifluoromethyl (CF 3 ), and the like.
- Halogenated alkoxy group The hydrogen atoms on the alkoxy group can be partially or completely replaced by halogen, such as difluoromethoxy (OCHF 2 ), trifluoromethoxy (OCF 3 ), and the like.
- halogen such as difluoromethoxy (OCHF 2 ), trifluoromethoxy (OCF 3 ), and the like.
- Cyanoalkyl straight or branched chain alkyl groups, the hydrogen atoms on these alkyl groups may be partially or completely replaced by cyano groups, and C 1 -C 4 in the cyano C 1 -C 4 alkyl group represents an alkyl group Chain length, such as CH 2 CN, CH 2 CH 2 CN, CH 2 CH 2 CH 2 CN, CH 2 CH 2 CH 2 CH 2 CN, CH(CH 3 )CN, CH(CH 2 CH 3 )CN, CH( CH 2 CH 2 CH 3 )CN, C(CH 3 )(CH 3 )CN or C(CH 3 )(CH 2 CH 3 )CN.
- Insecticides substances that have insecticidal effects on pests.
- Animal parasite control agent refers to an active compound that can effectively reduce the incidence of various parasites in animals infected by parasites. Control means that the active compound can effectively kill parasites, inhibit their growth or reproduction.
- the compounds represented by the general formula I, the general formula II and the general formula III of the present invention can be respectively prepared, which are further specifically described as follows:
- the intermediate compound II.14 (white solid) was prepared by reacting the intermediate compound IV-4 with bromopropionitrile.
- the NMR and MS data of the intermediate compound II.14 are as follows:
- the intermediate compound II.15 (white solid) was prepared by reacting the intermediate compound IV-4 with bromobutyronitrile.
- the NMR and MS data of the intermediate compound II.15 are as follows:
- the intermediate compound II.16 (white solid) was prepared by reacting the intermediate compound IV-4 with bromovaleronitrile.
- the NMR and MS data of the intermediate compound II.16 are as follows:
- compound 11 (yellow solid) was prepared by reacting intermediate compound II.11 and intermediate V-1.
- the NMR and MS data of compound 11 are as follows:
- compound 12 (yellow solid) was prepared by reacting intermediate compound II.12 with intermediate V-1.
- the NMR and MS data of compound 12 are as follows:
- compound 15 (yellow solid) was prepared by reacting intermediate compound II.15 and intermediate V-1.
- the NMR and MS data of compound 15 are as follows:
- compound 16 (yellow oil) was prepared by reacting intermediate compound II.16 and intermediate V-1.
- the NMR and MS data of compound 16 are as follows:
- compound 17 (white solid) was prepared by reacting intermediate compound II.1 and intermediate V-2.
- the NMR and MS data of compound 17 are as follows:
- compound 25 (yellow solid) was prepared by reacting intermediate compound II.9 and intermediate V-2.
- the NMR and MS data of compound 25 are as follows:
- compound 26 (yellow solid) was prepared by reacting intermediate compound II.10 and intermediate V-2.
- the NMR and MS data of compound 26 are as follows:
- compound 27 (yellow solid) was prepared by reacting intermediate compound II.11 and intermediate V-2.
- the NMR data of compound 27 are as follows:
- compound 28 (yellow solid) was prepared by reacting intermediate compound II.12 with intermediate V-2.
- the NMR and MS data of compound 28 are as follows:
- compound 32 (yellow solid) was prepared by reacting intermediate compound II.16 and intermediate V-2.
- the NMR and MS data of compound 32 are as follows:
- Example 36 Determination of biological activity of Armyworm, Plutella xylostella, Chilo suppressalis
- the insecticidal activity test of several insects was carried out with the compound of the present invention.
- the measurement method is as follows:
- test compound After the test compound is dissolved in a mixed solvent of acetone/methanol (1:1), it is diluted with water containing 0.1% (wt) Tween 80 to the desired concentration.
- Measurement method cut corn leaves into 2cm leaf sections, the pressure of Airbrush spray treatment is 10psi (approximately 0.7kg/cm 2 ), the front and back sides of each leaf section are sprayed, and the spray volume of the compound to be tested is 0.5ml. After drying in the shade, 10 3rd instar larvae were inserted into each treatment, and repeated 3 times for each treatment. After the treatment, it was placed in an observation room at 25°C and a relative humidity of 60-70%, and the number of surviving insects was investigated 3 days after the treatment, and the mortality rate was calculated.
- Measurement method Use a punch to punch cabbage leaves into leaf discs with a diameter of 2 cm.
- the pressure of Airbrush spray treatment is 10 psi (approximately 0.7 kg/cm 2 ), and the front and back sides of each leaf disc are sprayed.
- the spray volume of the compound to be tested is 0.5ml. After drying in the shade, 10 3rd instar larvae were inserted into each treatment, and repeated 3 times for each treatment. After the treatment, it was placed in an observation room at 25°C and a relative humidity of 60-70%, and the number of surviving insects was investigated 3 days after the treatment, and the mortality rate was calculated.
- the lethality of compounds 9, 10, 11, 12, 13, 14, 15, and 16 to Plutella xylostella was more than 90%.
- the compound 2, 10, 26 of the present invention and the control compound were selected for a parallel comparison test of the insecticidal activity of Plutella xylostella (3 days after the drug), and the determination method was the same as the previous one; the results are shown in Table 5:
- Measurement method 1) Preparation of rice seedlings: cultivate rice in a plastic cup with a diameter of 4.5 cm and a height of 4 cm in a constant temperature room (temperature 26-28°C, relative humidity 60-80%, light 16hL:8hD), and wait until the rice grows. At the 4 to 5 leaf stage, select robust and consistent rice seedlings for chemical treatment, and set 3 repetitions for each treatment. 2) Preparation for test insects: Chilo suppressalis, 3rd instar larvae continuously reared indoors. 3) The rice stalk is sprayed with insects. The spray method is adopted to uniformly spray the whole plant of the rice seedlings, and 15 ml of medicine is used for each treatment.
- the rice seedlings are sprayed, they are placed in a cool place to dry the liquid, and about 5 cm of the stalk at the base of the stem is cut to feed the test insects.
- the present invention provides an isophthalamide compound with excellent insecticidal activity. It can be used to prepare drugs for controlling pests in agriculture and other fields, and for preparing drugs for controlling animal parasites in the field of veterinary medicine.
Abstract
Description
编号 | R 1 | R 2 | R 3 | R 4 |
II.1 | Br | Br | CF 3 | CH 2CN |
II.2 | Br | Br | CF 3 | CH 2CH 2CN |
II.3 | Br | Br | CF 3 | CH 2CH 2CH 2CN |
II.4 | Br | Br | CF 3 | CH 2CH 2CH 2CH 2CN |
II.5 | Br | I | CF 3 | CH 2CN |
II.6 | Br | I | CF 3 | CH 2CH 2CN |
II.7 | Br | I | CF 3 | CH 2CH 2CH 2CN |
II.8 | Br | I | CF 3 | CH 2CH 2CH 2CH 2CN |
II.9 | Br | CF 3 | CF 3 | CH 2CN |
II.10 | Br | CF 3 | CF 3 | CH 2CH 2CN |
II.11 | Br | CF 3 | CF 3 | CH 2CH 2CH 2CN |
II.12 | Br | CF 3 | CF 3 | CH 2CH 2CH 2CH 2CN |
II.13 | I | CF 3 | CF 3 | CH 2CN |
II.14 | I | CF 3 | CF 3 | CH 2CH 2CN |
II.15 | I | CF 3 | CF 3 | CH 2CH 2CH 2CN |
II.16 | I | CF 3 | CF 3 | CH 2CH 2CH 2CH 2CN |
II.17 | Br | Br | CF 2CF 3 | CH 2CN |
II.18 | Br | Br | CF 2CF 3 | CH 2CH 2CN |
II.19 | Br | Br | CF 2CF 3 | CH 2CH 2CH 2CN |
II.20 | Br | Br | CF 2CF 3 | CH 2CH 2CH 2CH 2CN |
II.21 | Br | I | CF 2CF 3 | CH 2CN |
II.22 | Br | I | CF 2CF 3 | CH 2CH 2CN |
II.23 | Br | I | CF 2CF 3 | CH 2CH 2CH 2CN |
II.24 | Br | I | CF 2CF 3 | CH 2CH 2CH 2CH 2CN |
II.25 | Br | CF 3 | CF 2CF 3 | CH 2CN |
II.26 | Br | CF 3 | CF 2CF 3 | CH 2CH 2CN |
II.27 | Br | CF 3 | CF 2CF 3 | CH 2CH 2CH 2CN |
II.28 | Br | CF 3 | CF 2CF 3 | CH 2CH 2CH 2CH 2CN |
II.29 | I | CF 3 | CF 2CF 3 | CH 2CN |
II.30 | I | CF 3 | CF 2CF 3 | CH 2CH 2CN |
II.31 | I | CF 3 | CF 2CF 3 | CH 2CH 2CH 2CN |
II.32 | I | CF 3 | CF 2CF 3 | CH 2CH 2CH 2CH 2CN |
编号 | R 4 | R 5 | L |
III.1 | CH 2CN | F | Cl |
III.2 | CH 2CH 2CN | F | Cl |
III.3 | CH 2CH 2CH 2CN | F | Cl |
III.4 | CH 2CH 2CH 2CH 2CN | F | Cl |
III.5 | CH 2CN | F | OH |
III.6 | CH 2CH 2CN | F | OH |
III.7 | CH 2CH 2CH 2CN | F | OH |
III.8 | CH 2CH 2CH 2CH 2CN | F | OH |
III.9 | CH 2CN | CF 3 | Cl |
III.10 | CH 2CH 2CN | CF 3 | Cl |
III.11 | CH 2CH 2CH 2CN | CF 3 | Cl |
III.12 | CH 2CH 2CH 2CH 2CN | CF 3 | Cl |
III.13 | CH 2CN | CF 3 | OH |
III.14 | CH 2CH 2CN | CF 3 | OH |
III.15 | CH 2CH 2CH 2CN | CF 3 | OH |
III.16 | CH 2CH 2CH 2CH 2CN | CF 3 | OH |
Claims (24)
- 根据权利要求1所述的化合物,其特征在于:通式I中R 1选自卤素;R 2选自卤素、C 1-C 2卤代烷基或C 1-C 2卤代烷氧基;R 3选自CF 3或CF 2CF 3;R 4选自氰基C 1-C 4烷基;R 5选自氟、二氟甲基或三氟甲基。
- 根据权利要求2所述的化合物,其特征在于:通式I中R 1选自溴或碘;R 2选自溴、碘、三氟甲基或二氟甲氧基;R 3选自CF 3或CF 2CF 3;R 4选自CH 2CN、CH 2CH 2CN、CH 2CH 2CH 2CN、CH 2CH 2CH 2CH 2CN、CH(CH 3)CN、CH(CH 2CH 3)CN、CH(CH 2CH 2CH 3)CN、C(CH 3)(CH 3)CN或C(CH 3)(CH 2CH 3)CN;R 5选自氟、二氟甲基或三氟甲基。
- 根据权利要求3所述的化合物,其特征在于:通式I中R 1选自溴或碘;R 2选自溴、碘或三氟甲基;R 3选自CF 3;R 4选自CH 2CN、CH 2CH 2CN、CH 2CH 2CH 2CN或CH 2CH 2CH 2CH 2CN;R 5选自氟或三氟甲基。
- 根据权利要求7所述的中间体化合物,其特征在于:通式II中R 1选自卤素;R 2选自卤素、C 1-C 2卤代烷基或C 1-C 2卤代烷氧基;R 3选自CF 3或CF 2CF 3;R 4选自氰基C 1-C 4烷基。
- 根据权利要求8所述的中间体化合物,其特征在于:通式II中R 1选自溴或碘;R 2选自溴、碘、三氟甲基或二氟甲氧基;R 3选自CF 3或CF 2CF 3;R 4选自CH 2CN、CH 2CH 2CN、CH 2CH 2CH 2CN、CH 2CH 2CH 2CH 2CN、CH(CH 3)CN、CH(CH 2CH 3)CN、CH(CH 2CH 2CH 3)CN、C(CH 3)(CH 3)CN或C(CH 3)(CH 2CH 3)CN。
- 根据权利要求9所述的中间体化合物,其特征在于:通式II中R 1选自溴或碘;R 2选自溴、碘或三氟甲基;R 3选自CF 3;R 4选自CH 2CN、CH 2CH 2CN、CH 2CH 2CH 2CN或CH 2CH 2CH 2CH 2CN。
- 根据权利要求10所述的中间体化合物,其特征在于,中间体化合物选自:表3化合物,表3化合物具有如通式II的结构且R 1、R 2、R 3和R 4如表3中所示;表3
编号 R 1 R 2 R 3 R 4 II.1 Br Br CF 3 CH 2CN II.2 Br Br CF 3 CH 2CH 2CN II.3 Br Br CF 3 CH 2CH 2CH 2CN II.4 Br Br CF 3 CH 2CH 2CH 2CH 2CN II.5 Br I CF 3 CH 2CN II.6 Br I CF 3 CH 2CH 2CN II.7 Br I CF 3 CH 2CH 2CH 2CN II.8 Br I CF 3 CH 2CH 2CH 2CH 2CN II.9 Br CF 3 CF 3 CH 2CN II.10 Br CF 3 CF 3 CH 2CH 2CN II.11 Br CF 3 CF 3 CH 2CH 2CH 2CN II.12 Br CF 3 CF 3 CH 2CH 2CH 2CH 2CN II.13 I CF 3 CF 3 CH 2CN II.14 I CF 3 CF 3 CH 2CH 2CN II.15 I CF 3 CF 3 CH 2CH 2CH 2CN II.16 I CF 3 CF 3 CH 2CH 2CH 2CH 2CN II.17 Br Br CF 2CF 3 CH 2CN II.18 Br Br CF 2CF 3 CH 2CH 2CN II.19 Br Br CF 2CF 3 CH 2CH 2CH 2CN II.20 Br Br CF 2CF 3 CH 2CH 2CH 2CH 2CN II.21 Br I CF 2CF 3 CH 2CN II.22 Br I CF 2CF 3 CH 2CH 2CN II.23 Br I CF 2CF 3 CH 2CH 2CH 2CN II.24 Br I CF 2CF 3 CH 2CH 2CH 2CH 2CN II.25 Br CF 3 CF 2CF 3 CH 2CN II.26 Br CF 3 CF 2CF 3 CH 2CH 2CN II.27 Br CF 3 CF 2CF 3 CH 2CH 2CH 2CN II.28 Br CF 3 CF 2CF 3 CH 2CH 2CH 2CH 2CN II.29 I CF 3 CF 2CF 3 CH 2CN II.30 I CF 3 CF 2CF 3 CH 2CH 2CN II.31 I CF 3 CF 2CF 3 CH 2CH 2CH 2CN II.32 I CF 3 CF 2CF 3 CH 2CH 2CH 2CH 2CN - 根据权利要求12所述的中间体化合物,其特征在于:通式III中R 4选自CH 2CN、CH 2CH 2CN、CH 2CH 2CH 2CN、CH 2CH 2CH 2CH 2CN、CH(CH 3)CN、CH(CH 2CH 3)CN、CH(CH 2CH 2CH 3)CN、C(CH 3)(CH 3)CN或C(CH 3)(CH 2CH 3)CN;R 5选自氟、二氟甲基或三氟甲基;L选自卤素或羟基。
- 根据权利要求13所述的中间体化合物,其特征在于,中间体化合物选自:表4化合物,表4化合物具有如通式III的结构且R 4、R 5和L如表4中所示;表4
编号 R 4 R 5 L III.1 CH 2CN F Cl III.2 CH 2CH 2CN F Cl III.3 CH 2CH 2CH 2CN F Cl III.4 CH 2CH 2CH 2CH 2CN F Cl III.5 CH 2CN F OH III.6 CH 2CH 2CN F OH III.7 CH 2CH 2CH 2CN F OH III.8 CH 2CH 2CH 2CH 2CN F OH III.9 CH 2CN CF 3 Cl III.10 CH 2CH 2CN CF 3 Cl III.11 CH 2CH 2CH 2CN CF 3 Cl III.12 CH 2CH 2CH 2CH 2CN CF 3 Cl III.13 CH 2CN CF 3 OH III.14 CH 2CH 2CN CF 3 OH III.15 CH 2CH 2CH 2CN CF 3 OH III.16 CH 2CH 2CH 2CH 2CN CF 3 OH - 一种根据权利要求1-6之一所述的间苯二甲酰胺类化合物在制备杀虫剂中的用途。
- 根据权利要求15所述的用途,其特征在于:所述杀虫剂用于防治粘虫、小菜蛾、二化螟中的一种或几种。
- 一种杀虫剂制剂,其特征在于:所述杀虫剂制剂中含有权利要求1-6之一所述的间苯二甲酰胺类化合物作为活性组分,还含有一种或多种辅料;可选地,杀虫剂制剂中权利要求1-6之一所述的间苯二甲酰胺类化合物的量为0.1至99重量%,进一步可选地为0.5至90重量%。
- 一种杀虫剂组合物,其特征在于:包括权利要求1-6之一所述的间苯二甲酰胺类化合物和其他活性化合物的混合物,所述其他活性化合物选***虫剂、毒饵剂、消毒剂、杀螨剂、杀线虫剂、杀真菌剂、生长调节剂、除草剂中的一种或多种。
- 一种控制农业或林业害虫的方法,其特征在于:将有效剂量的材料施用于需要控制的害虫或其生长介质上,所述材料选自下组中的一种或多种:权利要求1-6之一所述的间苯二甲酰胺类化合物;权利要求17所述的杀虫剂制剂;权利要求18所述的杀虫剂组合物。
- 一种根据权利要求1-6之一所述的间苯二甲酰胺类化合物在制备动物寄生虫防治剂中的用途。
- 根据权利要求20所述的用途,其特征在于:所述动物寄生虫防治剂用于防治猫蚤、美洲犬蜱中的一种或几种。
- 一种动物寄生虫防治剂,其特征在于:所述动物寄生虫防治剂中含有权利要求1-6之一所述的间苯二甲酰胺类化合物作为活性组分,还含有一种或多种辅料;可选地,动物寄生虫防治剂中权利要求1-6之一所述的间苯二甲酰胺类化合物的量为1至80重量%。
- 一种动物寄生虫防治组合物,其特征在于:包括权利要求1-6之一所述的间苯二甲酰胺类化合物和其他动物寄生虫防治活性化合物的混合物,所述其他动物寄生虫防治活性化合物选***螨剂、杀昆虫剂、杀寄生虫剂、抗疟原虫剂中的一种或多种。
- 一种控制动物寄生虫的方法,其特征在于:包括以下步骤:将有效剂量的材料施于需要控制的动物寄生虫或其生长介质上,所述材料选自下组中的一种或多种:权利要求1-6之一所述的间苯二甲酰胺类;权利要求22所述的动物寄生虫防治剂;权利要求23所述的动物寄生虫防治组合物。
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