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WO2012034472A1 - Composés cyanobenzènedicarboxamides, leurs procédés de préparation et leurs utilisations comme insecticides agricoles - Google Patents

Composés cyanobenzènedicarboxamides, leurs procédés de préparation et leurs utilisations comme insecticides agricoles Download PDF

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Publication number
WO2012034472A1
WO2012034472A1 PCT/CN2011/078711 CN2011078711W WO2012034472A1 WO 2012034472 A1 WO2012034472 A1 WO 2012034472A1 CN 2011078711 W CN2011078711 W CN 2011078711W WO 2012034472 A1 WO2012034472 A1 WO 2012034472A1
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group
substituted
hydrogen
cyano
formula
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PCT/CN2011/078711
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English (en)
Chinese (zh)
Inventor
朱冰春
邢家华
许天明
郑志文
陈杰
彭伟立
许勇华
孔小林
魏优昌
董德臻
袁静
韦伟
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中化蓝天集团有限公司
浙江省化工研究院有限公司
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Priority to PH1/2013/500384A priority Critical patent/PH12013500384B1/en
Publication of WO2012034472A1 publication Critical patent/WO2012034472A1/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
    • 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
    • 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
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
    • 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
    • C07C255/24—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same saturated acyclic carbon skeleton
    • C07C255/29—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same saturated acyclic carbon skeleton containing cyano groups and acylated amino groups bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
    • C07C317/48—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/60—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
    • 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
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
    • C07D307/90—Benzo [c] furans; Hydrogenated benzo [c] furans with an oxygen atom in position 1 and a nitrogen atom in position 3, or vice versa

Definitions

  • the present invention relates to a phthalic acid amide compound, a preparation method and use as an agrochemical insecticide.
  • phthalamide compounds are known to have insecticidal activity (see EP0919542A2, W02004/018410AK W02010/012442A2), in which phthalate is jointly developed by the Japanese pesticide company and Bayer.
  • the formamide compound flubendiamide has good insecticidal activity against a variety of agricultural and horticultural lepidopteran pests (J. Pesticide Sci., 2005, 30(4): 354-360).
  • the replacement of phthalamides as pesticides has caused widespread concern among researchers of pesticide creation and has become a hot spot in the research of new insecticides.
  • An object of the present invention is to provide a cyano group-containing phthalic acid amide compound which can control various pests and diseases at a small dose, and which can be applied to agriculture to control crop diseases and insect pests.
  • the present invention provides the following technical solutions:
  • RR 2 is independently selected from hydrogen, dC 6 ortho, cycloalkyl, C 2 -C 6 alkenyl or ⁇ -alkynyl, and the hydrogen on the group may also be halogen, cyano, nitro, dC a 6- methoxy group, a phenyl group, a substituted phenyl group, a phenoxy group, a substituted phenoxy group, an alkylthio group, an alkylsulfinyl group or a decylsulfonyl group;
  • R 1 and R 2 together with the attached carbon form a cycloalkyl group
  • R 3 is selected from the group consisting of hydrogen, halogen, cyano, nitro, aryl, ester, dC 6 fluorenyl, halogenated dC 6 fluorenyl, dC 6 decyloxy or halodecyloxy;
  • R 4 is selected from hydrogen or ( ⁇ -(: 6 fluorenyl);
  • X is selected from a methylene group, a dC 6 alkyl group, a cyano substituted methylene group or a direct bond;
  • X and R 4 are bonded to the N to form a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, a five-membered heterocyclic ring or a six-membered heterocyclic ring;
  • Y is selected from the group consisting of hydrogen, halogen, cyano, nitro, a hydroxy group, a dC 6 alkyl group, a halogenated dC 6 fluorenyl group, a dC 3 decyloxy group, a halogenated dC 3 decyloxy group, a phenyl group, a substituted phenyl group, a heterocyclic aryl group or a substituted heterocyclic aryl group;
  • A is CH or N
  • n is an integer from 0 to 4.
  • RR 2 is independently selected from hydrogen, alkyl, C 3 -C 6 cyclodecyl or ( 2 -(: 3 alkenyl), phenyl, substituted phenoxy which may also be substituted by hydrogen on the group Further substituted with thiol, decylsulfinyl or decylsulfonyl;
  • R 1 and R 2 together with the attached carbon form a cyclohexyl group
  • R 3 is selected from hydrogen or halogen
  • R 4 is selected from hydrogen or ⁇ - ⁇ fluorenyl
  • X and R 4 are bonded to the N to form a five-membered heterocyclic ring or a six-membered heterocyclic ring;
  • Y is selected from hydrogen, a halogen atom, nitro, hydroxy, burning dC 3-yl, fluorinated alkyl with dC 3, dC 3 alkoxy or fluoro - embankment group;
  • n is an integer of 1 to 3.
  • RR 2 is independently selected from hydrogen, methyl, ethyl, isopropyl, cyclopropyl or allylic.
  • the hydrogen on the group can also be a group such as a substituted phenyl group, a substituted phenoxy group, a methylthio group, a methylsulfinyl group, a methylsulfonyl group or the like;
  • R 3 is selected from fluorine, chlorine, bromine or iodine, and R 3 is at the 3 or 4 position of the benzene ring;
  • R 4 is hydrogen or methyl
  • X is a methylene group, a methyl group, a cyano substituted methylene group or a direct bond
  • X and R 4 are bonded to the N to form an oxygen-containing six-membered heterocyclic ring;
  • Y is selected from the group consisting of hydrogen, fluorine, chlorine, nitro, hydroxy, methyl, methoxy, trifluoromethyl, trifluoromethoxy or heptafluoroisopropyl.
  • the structural formula of the cyano group-containing phthalamide compound represented by the above (I) is:
  • RR 2 , R 3 , R ⁇ A, X, Y and m are defined as a fluorenyl group, which is a linear or branched form, for example, a Bases such as ethyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, n-hexyl and the like.
  • Cyclodecyl is meant to include cyclic chain forms such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like.
  • Alkenyl means straight-chain or branched form, such as ethenyl, 1-propenyl, allyl, isopropenyl, 1-butenyl, 1, 3-butadienyl, 1-hexenyl, etc. Group.
  • An alkynyl group means a straight or branched chain form such as an ethynyl group, a 2-butynyl group, a 2-pentynyl group, a 3-hexynyl group or the like.
  • Halogenated fluorenyl refers to a group wherein the fluorenyl group is substituted by one or more halogen atoms.
  • the methoxy group means a group having an oxygen atom bonded to the terminal of the oxime group, for example, a methoxy group, an ethoxy group, a n-propoxy group, an isopropoxy group, a tetrabutoxy group or the like.
  • the haloalkoxy group means a group in which a mercapto group is substituted by one or more halogen atoms and an oxygen atom is bonded to the terminal.
  • the thiol group is a group having a sulfur atom attached to the end of the thiol group, such as a methylthio group, an ethylthio group or the like.
  • the mercaptosulfinyl group means a group having a terminal group of (S0-), such as a methylsulfinyl group.
  • the mercaptosulfonyl group means a group having a terminal (S0 2 - ) at the alkyl group, such as a methylsulfonyl group.
  • Halogen means fluorine, chlorine, bromine or iodine.
  • the cyano group-containing phthalamide compound represented by the formula (I) of the present invention may have, in some cases, one or more asymmetric centers in its structural formula, and in some cases, two or more optical isomerisms. Bulk and diastereomers. The invention also includes all individual optical isomers and mixtures of these isomers in any ratio.
  • the present invention also provides an intermediate for preparing a cyano group-containing phthalamide compound represented by the formula (I), which has the following formula (II) or (III):
  • RR 2 is independently selected from hydrogen, d-alkyl, C 3 -C 6 cyclodecyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl, and the hydrogen on the group may also be halogen , cyano, nitro, ( ⁇ -[: 6 methoxy, phenyl, substituted phenyl, phenoxy, substituted phenoxy, alkylthio, alkylsulfinyl or decylsulfonyl further Replace
  • R 3 is selected from the group consisting of hydrogen, halogen, cyano, nitro, aryl, ester, dC 6 alkyl, halogenated d-Ce fluorenyl, alkoxy or halo-c decyloxy.
  • RR 2 is independently selected from hydrogen, dC 3 fluorenyl, C 3 -C 6 cyclodecyl or C 2 -C 3 alkenyl, and the hydrogen on the group may also be substituted phenyl, substituted phenoxy Further substituted with a thiol group, a fluorenylsulfinyl group or an alkylsulfonyl group;
  • R 1 and R 2 together with the attached carbon form a cyclohexyl group
  • R 3 is selected from hydrogen or halogen.
  • RR 2 are independently selected from hydrogen, methyl, ethyl, isopropyl, cyclopropyl or allyl, hydrogens on the group may also be substituted phenyl, substituted phenoxy, methylthio a group such as a methylsulfinyl group or a methylsulfonyl group;
  • R 3 is selected from fluorine, chlorine, bromine or iodine, and R 3 is located at the 3 or 4 position of the benzene ring.
  • the cyano group-containing phthalamide compound represented by (I) of the present invention can be produced by the following method:
  • RR 2 , R 3 , R 4 , Y and m define a cyano group-containing phthalamide compound represented by the above structural formula (I).
  • the inert solvent in the above step (1) is selected from the group consisting of tetrahydrofuran, acetonitrile, 1, 4-dioxane, hydrazine, hydrazine-dimethylformamide, hydrazine, hydrazine-dimethylacetamide.
  • the base comprising an organic base and an inorganic base, the organic base being selected from the group consisting of triethylamine, pyridine or 3-methylpyridine, the inorganic base being selected From potassium carbonate, sodium hydrogencarbonate, sodium hydroxide or anhydrous sodium acetate;
  • the inert solvent in the above step (2) is selected from the group consisting of toluene, 1,2-dichloroethane, ethyl acetate, tetrahydrofuran, acetonitrile, 1, One or a combination of two or more of 4-dioxane or dichloromethane, the acylating reagent being methyl chloroformate, acetic anhydride or trifluoroacetic anhydride, for each mole of the amide of the formula ( ⁇ )
  • the benzoic acid, the acylating agent may be used in an amount of from 1 mole to the excess mole; the iner
  • the acid includes an organic acid selected from the group consisting of acetic acid, trifluoroacetic acid or p-toluenesulfonic acid, and the inorganic acid is hydrochloric acid or sulfuric acid; the reaction temperature is 0° C. Between the boiling points of the inert solvent used.
  • the reaction time varies depending on the reaction scale and the reaction temperature, and is preferably 2 to 12 hours.
  • the product of the formula (I) can be separated from the reaction mixture by a conventional filtration or the like, and if necessary, separation means such as recrystallization or column chromatography can be used.
  • the product in the above step (1) is acidified, extracted, and concentrated to precipitate a solid, which is washed with a solvent, filtered, and then separated.
  • the substituted phthalic anhydride represented by the formula (VI) used in the above production method is a known compound which can be produced by a number of known methods.
  • Typical compounds represented by the formula (I) of the present invention are listed in the index table 1 and the index table 2, but they are in no way intended to limit the scope of the invention.
  • a typical compound represented by the formula (I) when R 4 is hydrogen and X is a direct bond, a typical compound such as Da) shows:
  • Table 3 shows the nuclear magnetic data of some of the compounds described in Index Table 1 and Index Table 2.
  • the cyano group-containing phthalamide compound represented by the formula (I) of the present invention or an agriculturally applicable salt thereof can be used for an agrochemical insecticide.
  • the agricultural and horticultural pest control agent containing the compound of the present invention is particularly effective for agricultural pests and the like.
  • the agricultural and horticultural pest control agent containing the cyano group-containing phthalamide compound represented by the formula (I) of the present invention is used for controlling organophosphorus, carbamate, pyrethroid, and benzoic acid. Resistant pests such as ureide are effective. Further, the cyano group-containing phthalamide compound represented by the formula (I) of the present invention has excellent osmotic transfer property, and therefore contains a cyano group represented by the formula (I) according to the present invention.
  • the phthalate-based agricultural and horticultural pest control agent is used to treat the soil, and the pests of the stems and leaves can also be controlled while controlling the soil harmful insects, mites and the like.
  • pest control agent containing the cyano group-containing phthalamide compound represented by the formula (I) of the present invention include comprehensive control of the plant parasitic mites and agricultural pests. , pest control agents for agricultural and horticultural use such as soil pests.
  • the cyano group-containing phthalic acid amide compound represented by the formula (I) of the present invention can be used as an active component of a chemical pesticide for pesticides, and is formulated into various liquid preparations, emulsifiable concentrates, suspension concentrates, aqueous suspensions, Microemulsions, (water) emulsions, powders, wettable powders, soluble powders, (water-dispersible) granules or capsules, for pest control of crops such as rice, soybeans, wheat, cotton, corn, vegetables and canola.
  • the weight percentage of the active component that is, the weight percentage of the cyano group-containing phthalamide compound represented by the formula (I) of the present invention is preferably 0. 001%-99. 99% by weight, the balance being an agriculturally acceptable carrier.
  • the carrier can be a solid or a liquid.
  • Suitable solid carriers include natural or synthetic clays and silicates such as natural silica and diatomaceous earth; magnesium silicates such as talc; magnesium aluminosilicates such as kaolinite, kaolin, montmorillonite and mica; , calcium carbonate, light calcium carbonate; calcium sulfate; limestone; sodium sulfate; amine salts such as ammonium sulfate, hexamethylenediamine.
  • the liquid carrier includes water and an organic solvent, and when water is used as a solvent or a diluent, the organic solvent can also be used as an adjuvant or an antifreezing additive.
  • Suitable organic solvents include aromatic hydrocarbons such as benzene, xylene, toluene, etc.; chlorinated hydrocarbons such as chlorobenzene, vinyl chloride, trichloromethane, Methylene chloride or the like; aliphatic hydrocarbons such as petroleum distillate, cyclohexane, light mineral oil; alcohols such as isopropanol, butanol, ethylene glycol, glycerol and cyclohexanol; and ethers and esters thereof There are also ketones such as acetone, cyclohexanone, and dimethylformamide and N-methyl-pyrrolidone.
  • aromatic hydrocarbons such as benzene, xylene, toluene, etc.
  • chlorinated hydrocarbons such as chlorobenzene, vinyl chloride, trichloromethane, Methylene chloride or the like
  • aliphatic hydrocarbons such as petroleum distillate, cyclohexane, light
  • the carrier can also be a surfactant.
  • Suitable surfactants can be emulsifiers, dispersants or wetting agents; they can be ionic or nonionic.
  • Nonionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, polyoxyethylene fatty ammonia, and commercially available emulsifiers: agricultural milk 2201B, agricultural milk 0203B, agricultural milk 10 (f, agricultural milk 50 ( f, agricultural milk 600 agricultural milk 600- 2 # , agricultural milk 1601, agricultural milk 2201, agricultural milk NP-10, agricultural milk NP- 15, agricultural milk 507*, agricultural milk 0X- 635, agricultural milk 0X-622, agriculture Milk 0X-653, agricultural milk 0X-667, Ning milk 36 s .
  • Dispersing agent includes sodium lignosulfonate, pull-up powder, calcium lignosulfonate, methylnaphthalenesulfonic acid formaldehyde condensate, etc.
  • Wetting agent laurel Sodium sulphate, sodium dodecyl benzene sulfonate, sodium decyl naphthalene sulfonate, and the like.
  • the above pesticide chemical pesticides can be prepared by a general method.
  • the active substance may be mixed with a liquid solvent and/or a solid carrier, and a surfactant such as an emulsifier, a dispersant, a stabilizer, a wetting agent may be added, and other auxiliary agents such as a binder, an antifoaming agent, an oxidizing agent may also be added. Wait.
  • the cyano group-containing phthalamide compound of the present invention can also be used in combination with herbicides, fungicides, nematicides, plant growth regulators, fertilizers, and other pesticides or other agricultural chemicals. .
  • the pesticide preparation of the present invention when applied to a pest to be controlled or a medium for growth thereof, wherein the active component is a cyano group-containing phthalamide represented by formula (I)
  • the effective amount of the compound is from 10 grams to 1000 grams per hectare.
  • the cyano group-containing phthalamide compound represented by the formula (I) of the present invention or an agriculturally applicable salt thereof and a preparation thereof have the following advantages over the prior art:
  • the present invention introduces an ⁇ -amino nitrile functional group in the structure of phthalic acid for the first time, and the structure of the compound is novel;
  • the compound of the present invention and its preparation have an extremely high insecticidal activity: a good effect on lepidopteran pests at a dose of 0.16 mg/L;
  • the compound of the present invention and its preparation have excellent safety, and are safe to some crops such as wheat, soybean, cotton, corn, rice, etc., and are environmentally friendly.
  • the compound of the present invention and its preparation have reasonable toxicity, ecotoxicity and environmental compatibility, and are low-toxic environmentally friendly pesticides. detailed description
  • Step 1 Synthesis of 3-iodo-N-(1methyl-l-cyanoethyl)-amidobenzoic acid
  • Step 2 Synthesis 3-Iodo-N-(1methyl-monocyanoethyl) phthalimide
  • Trifluoroacetic anhydride (0.76 g, 3. 6 mmol) was added to 3-iodo-N-(1methyl-l-cyanoethyl)-amidobenzoic acid (1.07 g, 3 mmol) in 10 mL of toluene In the suspension, the reaction mixture was stirred at room temperature for 30 min. The solvent was removed under reduced pressure to give the title compound.
  • Step 3 Synthesis of 3-iodo-N 1 -(2methyl-tetrafluoropentylphenyl) N 2 —(1methyl-l-cyanoethyl)phthalamide
  • Step 2 Synthesis of 4-chloro-N (1 methyl-mono-cyanoethyl) phthalimide
  • Trifluoroacetic anhydride (1.0 g, 4. 8 mmol) was added to a suspension of 4-chloro-N (1methyl-l-cyanoethyl)-amidobenzoic acid (1. 06 g, 4 mmol) in 12 ml of toluene. The mixture was stirred at room temperature for 30 min. The solvent was removed under reduced pressure to give aq.
  • Step 3 Synthesis of 4-chloro-N 1 - ( 2, 4 - dichlorophenyl) N 2 (1 methyl- 1 - cyanoethyl) phthalic acid amide
  • Example 5 granule formula
  • the insecticidal activity evaluation test was carried out according to the following methods:
  • the screening concentration was from 500, 100, 20, 4.0. 8, 0. 16, 0. 032 mg / L, and the amount of the drug treatment solution was lOmL.
  • the test target was oriental worm (i 'mg separa ta), cotton bollworm (Helico this armigera), Aphis medicagini, PI u tell a xylostella, oofe ⁇ 's litura Spodopterem frugiperda).
  • the corn leaves are fully infiltrated in the liquid, and then dried naturally. They are placed in a petri dish, and the 3rd instar larvae are picked up and placed in the observation room. The test was repeated 4 times. The results were checked after 72 hours. The brush is lightly touched by the worm, and no reaction is considered to be dead.
  • Potted cotton (2-3 leaf age) was sprayed with the drug and allowed to dry. Put in the culture room and continue normal culture. After 5, 12, 19d, the leaves were cut with scissors, placed in a ⁇ 9cm plastic petri dish, and the larvae of the genus Spodoptera or Helicoverpa armigera were placed, and a filter paper was placed and capped. Place in the observation room and check the results after 6 days.
  • Potted cotton (2-3 leaf age) was sprayed with the drug and allowed to dry. Put in the culture room and continue normal culture. After 5, 12, 19d, the leaves were cut with scissors, placed in a ⁇ 9cm plastic petri dish, and the larvae of the genus Spodoptera or Helicoverpa armigera were placed, and a filter paper was placed and capped. Place in the observation room and check the results after 6 days.
  • the numbers described in the biological activity assay examples correspond to the compound numbers described in Index Table 1, Index Table 2, and Table 3.
  • Test Statistics The number of dead insects and live insects in each treatment was counted, and the mortality was calculated.
  • Dead IT rate (%) , x lOO
  • the CK control mortality was ⁇ 20%, the test results were credible, the test results were corrected, and the CK control mortality was ⁇ 5%.
  • the results of the bioassay test indicate that the compound of the present invention has good insecticidal activity, especially for lepidopteran pests such as oriental armyworm, cotton bollworm, diamondback moth, Spodoptera litura, and Spodoptera litura. Active, also has a certain insecticidal activity against Homoptera pests. "mg/L" refers to each mg of active substance per liter.
  • compounds 23, 24, 32, 33, 34, 40, 46, 47, 48, 137 have a mortality rate of more than 80% against Plutella xylostella, and at a concentration of 100 mg/L, compounds 23, 24, 33, 34 46, 47, 48, 137 have a mortality rate of more than 80% against Plutella xylostella.
  • the mortality of compounds 23, 24, 34, 46, 47, 48 against Plutella xylostella is greater than 80%, and the concentration of 4 mg/L is higher.
  • the mortality rate of compound 23, 24, 34, 47, 48 against Plutella xylostella is more than 80%, and the mortality rate of compound 23, 24, 47 against Plutella xylostella is greater than 80%, 0. 16mg/ At the L concentration, the mortality of compounds 24, 47 against Plutella xylostella was 100%.
  • the mortality rate of compounds 23 and 24 against Spodoptera frugiperda was greater than 80%.
  • the mortality rate of compound 24 against Spodoptera frugiperda was 100%.
  • Compound 24 had a mortality rate of 100% against Spodoptera litura.
  • Table 4 shows that compared with the existing compound flubendiamide, when the concentration is greater than 0.16 mg / L, the compound of the present invention has substantially the same insecticidal activity against Plutella xylostella, and exerts a high insecticidal action against Spodoptera litura. Especially at low application rates (0.032 Mg/L), the compounds of the invention are superior to the existing compounds and much higher than the activity of chlorpyrifos and cypermethrin. Based on the structural similarity of these compounds, the result of this increase is unexpected.
  • Compound 24 was subjected to a greenhouse residual activity test, and the results are shown in Table 5. The test results showed that: at 0. 8mg/L, the compound 24 was treated with the test insects 19 days after the drug, and the mortality rate of Plutella xylostella, Spodoptera frugiperda and Helicoverpa armigera was still 100%; at 0. 16mg/L, With the prolongation of treatment time, the efficacy was reduced. After 12 days, the drug could still reach 100%. After 19 days, the mortality of Plutella xylostella, Spodoptera frugiperda and Helicoverpa armigera decreased to 60%, 55 % and 80 %, respectively. At 0. 032 mg/L, the efficacy against all three test insects was low. It has a high residual activity on compound 24. Table 5 Compound 24 residual activity test results

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Abstract

L'invention porte sur des composés cyanobenzènedicarboxamides de formule (I), leurs procédés de préparation et leurs utilisations comme insecticides agricoles. Les composés ont des activités insecticides sur un large spectre.
PCT/CN2011/078711 2010-09-13 2011-08-22 Composés cyanobenzènedicarboxamides, leurs procédés de préparation et leurs utilisations comme insecticides agricoles WO2012034472A1 (fr)

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Cited By (105)

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Publication number Priority date Publication date Assignee Title
CN103039501A (zh) * 2013-01-06 2013-04-17 中化蓝天集团有限公司 一种含高效氯氰菊酯和zj4042的农业杀虫组合物
CN103053545A (zh) * 2012-12-25 2013-04-24 中化蓝天集团有限公司 一种含吡蚜酮的农业杀虫组合物
WO2013087709A1 (fr) 2011-12-15 2013-06-20 Bayer Intellectual Property Gmbh Associations de principes actifs ayant des propriétés insecticides et acaricides
WO2014005982A1 (fr) 2012-07-05 2014-01-09 Bayer Cropscience Ag Associations de principes actifs insecticides et fongicides
WO2014026984A1 (fr) 2012-08-17 2014-02-20 Bayer Cropscience Ag Amides d'acide azaindole-carboxylique et thiocarboxylique comme insecticides et acaricides
WO2014053450A1 (fr) 2012-10-02 2014-04-10 Bayer Cropscience Ag Composés hétérocycliques utilisés comme pesticides
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WO2014083033A1 (fr) 2012-11-30 2014-06-05 Bayer Cropsience Ag Mélange fongicide ou pesticide binaire
WO2014090765A1 (fr) 2012-12-12 2014-06-19 Bayer Cropscience Ag Utilisation de 1-[2-fluoro-4-méthyle-5-(2,2,2- trifluoroéthylsulfinyl)phényl]-5-amino-3-trifluorométhyl)-1 h-1,2,4 tfia zole à des fins de régulation des nématodes dans les cultures résistantes aux nématodes
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WO2014170328A1 (fr) 2013-04-19 2014-10-23 Bayer Cropscience Ag Associations de composés actifs ayant des propriétés insecticides
WO2014170254A1 (fr) 2013-04-19 2014-10-23 Bayer Cropscience Ag Associations synergiques insecticides de dérivés de phtaldiamide et d'abamectine, d'émamectine, de lepimectine ou de milbémectine
WO2014170354A1 (fr) * 2013-04-19 2014-10-23 Bayer Cropscience Ag Combinaisons synergiques insecticides et/ou fongicides de dérivés d'acide diamide phtalique et d'un autre ingrédient actif
WO2014170313A1 (fr) 2013-04-19 2014-10-23 Bayer Cropscience Ag Associations de composés actifs ayant des propriétés insecticides
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WO2024028243A1 (fr) 2022-08-02 2024-02-08 Basf Se Composés pesticides pyrazolo

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CN109897031B (zh) * 2017-12-11 2022-03-15 南京农业大学 一种含香豆素基团的苯并噻唑类衍生物及其制备方法与应用
CN109265381B (zh) * 2018-08-28 2020-10-27 中国农业大学 一种含氰基的邻苯二甲酰胺衍生物及其制备与应用
CN111362931B (zh) * 2018-12-26 2021-09-17 浙江省化工研究院有限公司 一种异噁唑啉连吡唑酰胺类化合物、其制备方法及应用
WO2022135447A1 (fr) * 2020-12-22 2022-06-30 南通泰禾化工股份有限公司 Composé benzamide à substitution cyano et son utilisation

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4041045A (en) * 1975-11-12 1977-08-09 American Cyanamid Company Dihydroimidaz oisoindolediones and the use thereof as herbicidal agents
IL51139A (en) * 1976-12-21 1979-10-31 American Cyanamid Co 3-substituted 3h-imidazo(2,1-a)isoindole-2,5-dione derivatives,their preparation and herbicidal methods employing them
US4719303A (en) * 1983-11-21 1988-01-12 American Cyanamid Company Preparation of substituted and unsubstituted 2-[(1-carbamoyl-1,2-dimethylpropyl)-carbamoyl]-3-quinolinecarboxylic, nicotinic and benzoic acids
CN1423632A (zh) * 1999-09-24 2003-06-11 日本农药株式会社 芳族二酰胺衍生物或其盐、农艺组合物及其使用方法
JP2005272452A (ja) * 2004-02-23 2005-10-06 Nissan Chem Ind Ltd 置換ベンズアニリド化合物及び有害生物防除剤
WO2010012442A2 (fr) * 2008-07-31 2010-02-04 Bayer Cropscience Ag Dérivé de benzènedicarboxamide insecticide
CN101935291A (zh) * 2010-09-13 2011-01-05 中化蓝天集团有限公司 一种含氰基的邻苯二甲酰胺类化合物、制备方法和作为农用化学品杀虫剂的用途

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6362369B2 (en) * 1997-11-25 2002-03-26 Nihon Nohyaku Co., Ltd. Phthalic acid diamide derivatives fluorine-containing aniline compounds as starting material, agricultural and horticultural insecticides, and a method for application of the insecticides
TW515786B (en) * 1997-11-25 2003-01-01 Nihon Nohyaku Co Ltd Phthalic acid diamide derivatives, agricultural and horticultural insecticides, and a method for application of the insecticides
WO2001046124A1 (fr) * 1999-12-22 2001-06-28 Nihon Nohyaku Co., Ltd. Derives de diamide aromatique, produits chimiques utilises en agriculture ou en horticulture et utilisations de ces derniers

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4041045A (en) * 1975-11-12 1977-08-09 American Cyanamid Company Dihydroimidaz oisoindolediones and the use thereof as herbicidal agents
IL51139A (en) * 1976-12-21 1979-10-31 American Cyanamid Co 3-substituted 3h-imidazo(2,1-a)isoindole-2,5-dione derivatives,their preparation and herbicidal methods employing them
US4719303A (en) * 1983-11-21 1988-01-12 American Cyanamid Company Preparation of substituted and unsubstituted 2-[(1-carbamoyl-1,2-dimethylpropyl)-carbamoyl]-3-quinolinecarboxylic, nicotinic and benzoic acids
CN1423632A (zh) * 1999-09-24 2003-06-11 日本农药株式会社 芳族二酰胺衍生物或其盐、农艺组合物及其使用方法
JP2005272452A (ja) * 2004-02-23 2005-10-06 Nissan Chem Ind Ltd 置換ベンズアニリド化合物及び有害生物防除剤
WO2010012442A2 (fr) * 2008-07-31 2010-02-04 Bayer Cropscience Ag Dérivé de benzènedicarboxamide insecticide
CN101935291A (zh) * 2010-09-13 2011-01-05 中化蓝天集团有限公司 一种含氰基的邻苯二甲酰胺类化合物、制备方法和作为农用化学品杀虫剂的用途

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
PETERSON, P. E. ET AL.: "SOME REACTIONS OF A-PHTHALIMIDONITRILES INCLUDING THOSE LEADING TO THE SYNTHESIS OF A-AMINOAMIDOXIMES AND A-AMINOTHIOAMIDES", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 79, no. 5, 1957, pages 1389 - 1395 *

Cited By (128)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013087709A1 (fr) 2011-12-15 2013-06-20 Bayer Intellectual Property Gmbh Associations de principes actifs ayant des propriétés insecticides et acaricides
WO2014005982A1 (fr) 2012-07-05 2014-01-09 Bayer Cropscience Ag Associations de principes actifs insecticides et fongicides
WO2014026984A1 (fr) 2012-08-17 2014-02-20 Bayer Cropscience Ag Amides d'acide azaindole-carboxylique et thiocarboxylique comme insecticides et acaricides
WO2014053450A1 (fr) 2012-10-02 2014-04-10 Bayer Cropscience Ag Composés hétérocycliques utilisés comme pesticides
WO2014060381A1 (fr) 2012-10-18 2014-04-24 Bayer Cropscience Ag Composés hétérocycliques pour la lutte contre les nuisibles
WO2014067962A1 (fr) 2012-10-31 2014-05-08 Bayer Cropscience Ag Nouveaux composés hétérocycliques utilisés comme agents de lutte contre les nuisibles
WO2014083033A1 (fr) 2012-11-30 2014-06-05 Bayer Cropsience Ag Mélange fongicide ou pesticide binaire
WO2014090765A1 (fr) 2012-12-12 2014-06-19 Bayer Cropscience Ag Utilisation de 1-[2-fluoro-4-méthyle-5-(2,2,2- trifluoroéthylsulfinyl)phényl]-5-amino-3-trifluorométhyl)-1 h-1,2,4 tfia zole à des fins de régulation des nématodes dans les cultures résistantes aux nématodes
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WO2014122083A1 (fr) 2013-02-06 2014-08-14 Bayer Cropscience Ag Dérivés de pyrazole halosubstitués en tant qu'agents phytosanitaires
EP2986121A1 (fr) * 2013-04-19 2016-02-24 Bayer CropScience Aktiengesellschaft Associations de composés actifs ayant des propriétés insecticides
US9554573B2 (en) 2013-04-19 2017-01-31 Bayer Cropscience Aktiengesellschaft Binary insecticidal or pesticidal mixture
WO2014170254A1 (fr) 2013-04-19 2014-10-23 Bayer Cropscience Ag Associations synergiques insecticides de dérivés de phtaldiamide et d'abamectine, d'émamectine, de lepimectine ou de milbémectine
WO2014170354A1 (fr) * 2013-04-19 2014-10-23 Bayer Cropscience Ag Combinaisons synergiques insecticides et/ou fongicides de dérivés d'acide diamide phtalique et d'un autre ingrédient actif
WO2014170313A1 (fr) 2013-04-19 2014-10-23 Bayer Cropscience Ag Associations de composés actifs ayant des propriétés insecticides
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WO2014170345A2 (fr) 2013-04-19 2014-10-23 Bayer Cropscience Ag Procédé pour l'utilisation améliorée du potentiel de production de plantes transgéniques
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US10149477B2 (en) 2014-10-06 2018-12-11 Basf Se Substituted pyrimidinium compounds for combating animal pests
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WO2018013380A1 (fr) 2016-07-11 2018-01-18 Covestro Llc, Et Al. Procédés de traitement de semences avec une composition aqueuse et semences traitées avec celle-ci
WO2018013382A1 (fr) 2016-07-11 2018-01-18 Covestro Llc, Et Al Compositions aqueuses de traitement de semences, semences traitées au moyen de ces compositions et procédés de traitement de semences
WO2018013381A1 (fr) 2016-07-11 2018-01-18 Covestro Llc, Et Al. Compositions aqueuses pour le traitement de semences, semences traitées avec de telles compositions, et procédés pour le traitement de semences
US10750750B2 (en) 2016-07-11 2020-08-25 Covestro Llc Aqueous compositions for treating seeds, seeds treated therewith, and methods for treating seeds
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US10653136B2 (en) 2016-07-11 2020-05-19 Covestro Llc Aqueous compositions for treating seeds, seeds treated therewith, and methods for treating seeds
WO2018019676A1 (fr) 2016-07-29 2018-02-01 Bayer Cropscience Aktiengesellschaft Combinaisons de composés actifs et procédés pour protéger le matériau de propagation des plantes
WO2018108671A1 (fr) 2016-12-16 2018-06-21 Basf Se Composés pesticides
WO2018162312A1 (fr) 2017-03-10 2018-09-13 Basf Se Dérivés spirocycliques
WO2018166855A1 (fr) 2017-03-16 2018-09-20 Basf Se Dihydroisoxazoles à substitution hétérobicyclique
WO2018177781A1 (fr) 2017-03-28 2018-10-04 Basf Se Composés pesticides
WO2018177970A1 (fr) 2017-03-31 2018-10-04 Basf Se Procédé de préparation de composés chiraux 2,3-dihydrothiazolo[3,2-a]pyrimidin-4-ium
EP3978504A1 (fr) 2017-03-31 2022-04-06 Basf Se Dérivés chiraux de 2,3-dihydrothiazolo[3,2-a]pyrimidine pour lutter contre des animaux nuisibles
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WO2018234202A1 (fr) 2017-06-19 2018-12-27 Basf Se Composés pyrimidinium substitués et dérivés destinés à lutter contre les animaux nuisibles
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US10743535B2 (en) 2017-08-18 2020-08-18 H&K Solutions Llc Insecticide for flight-capable pests
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WO2022243521A1 (fr) 2021-05-21 2022-11-24 Basf Se Utilisation de composés d'éthynylpyridine en tant qu'inhibiteurs de nitrification
WO2022243523A1 (fr) 2021-05-21 2022-11-24 Basf Se Utilisation d'un composé alcoxy pyrazole n-fonctionnalisé en tant qu'inhibiteur de nitrification
WO2022268810A1 (fr) 2021-06-21 2022-12-29 Basf Se Réseaux organométalliques à blocs de construction à base de pyrazole
WO2022268813A1 (fr) 2021-06-24 2022-12-29 Syngenta Crop Protection Ag Lutte contre les insectes, les acariens et les nématodes nuisibles
WO2022268815A1 (fr) 2021-06-24 2022-12-29 Syngenta Crop Protection Ag Lutte contre les insectes, les acariens et les nématodes nuisibles
WO2023203066A1 (fr) 2022-04-21 2023-10-26 Basf Se Action synergique en tant qu'inhibiteurs de nitrification d'oligomères de dicyandiamide (dcd) avec l'alcoxypyrazole et ses oligomères
WO2024028243A1 (fr) 2022-08-02 2024-02-08 Basf Se Composés pesticides pyrazolo

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PH12013500384B1 (en) 2018-09-26
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