+

WO2008134970A1 - Composés anthranilamides et leur utilisation - Google Patents

Composés anthranilamides et leur utilisation Download PDF

Info

Publication number
WO2008134970A1
WO2008134970A1 PCT/CN2008/070832 CN2008070832W WO2008134970A1 WO 2008134970 A1 WO2008134970 A1 WO 2008134970A1 CN 2008070832 W CN2008070832 W CN 2008070832W WO 2008134970 A1 WO2008134970 A1 WO 2008134970A1
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
hydrogen
group
halogenated
alkoxy
Prior art date
Application number
PCT/CN2008/070832
Other languages
English (en)
Chinese (zh)
Inventor
Changling Liu
Baoshan Chai
Aiying Guan
Hong Zhang
Yongwu Peng
Junfeng Wang
Huichao Li
Zhinian Li
Original Assignee
Sinochem Corporation
Shenyang Research Institute Of Chemical Industry
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from CN2007100111786A external-priority patent/CN101298435B/zh
Priority claimed from CN 200710011176 external-priority patent/CN101298451B/zh
Priority claimed from CN2008100571021A external-priority patent/CN101497602B/zh
Application filed by Sinochem Corporation, Shenyang Research Institute Of Chemical Industry filed Critical Sinochem Corporation
Publication of WO2008134970A1 publication Critical patent/WO2008134970A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/16—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

Definitions

  • the invention belongs to the field of agricultural insecticides and fungicides.
  • it relates to an orthoformylbenzamide compound and composition, and the use thereof as an insecticidal or bactericidal agent in agriculture or other fields. Background technique
  • invertebrate pests The control of invertebrate pests is extremely important in achieving high planting efficiency. Damage to growing and stored crops by invertebrate pests can cause a significant reduction in productivity and, consequently, an increase in consumer spending. Many of the products used for these purposes are commercially available, but new compounds that are more efficient, low cost, low toxic, environmentally safe or have different modes of action are still needed. O-formylaminobenzamides (Finedine Receptor Inhibitors) are effective insecticides for the prevention and treatment of invertebrate pests in recent years.
  • the object of the present invention is to provide an anthranilic benzene which can control various pests and diseases at a small dose.
  • Formic acid compounds which can be applied to agriculture to control crop diseases and insect pests.
  • the present invention provides an o-formylaminobenzamide compound, as shown in Formula I:
  • A is selected from N or CH;
  • B is selected from the group consisting of hydrogen, halogen, cyano, nitro, dC 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, halogenated dC 6 alkyl, dC 6 alkoxy, dC 6 alkane Thio group, dC 6 alkylsulfonyl group, dC 6 alkylcarbonyl group, dC 6 alkoxy dC 6 alkyl group, dC 6 alkoxycarbonyl group, dC 6 alkoxycarbonyl dC 6 alkyl group or ⁇ dC 6 alkoxy group dC 6 alkyl;
  • C is selected from hydrogen or halogen
  • R 2 is selected from the group consisting of hydrogen, halogen, CN, NO 2 , methylthio, methylsulfonyl, methoxycarbonyl, methylaminocarbonyl, ⁇ ⁇ unsubstituted or substituted by the following groups: methyl, dimethyl Base, acetyl, methylsulfonyl;
  • R 3 is selected from the group consisting of halogen, CS H 2 , OCH 2 CN, dC 6 alkyl, halogenated dC 6 alkyl, dC 6 alkoxy, halogenated dC 6 alkoxy, dC 6 alkylthio, halogenated dC 6 Alkylthio, dC 6 alkylsulfonyl, halogenated dC 6 alkylsulfonyl, dC 6 alkylcarbonyl, dC 6 alkoxyfluorenyl, dC 6 alkoxy dC 6 alkyl, halogenated dC 6 alkoxy dC 6 alkyl, halogenated dC 6 alkoxy dC 6 alkoxy, dC 6 alkylthio dC 6 alkyl, halogenated dC 6 alkylthio dC 6 alkyl, C 2 -C 6 alkenyloxy, halogenated C
  • R 5 is selected from the group consisting of CN dC 4 alkyl, halogenated dC 6 alkyl, -NHCOCH 2 CN - HCOCF3 H 2 CF 3 - 0 -CH 2 C0 2 CH 3 -CH(C0 2 Et) 2 C3 ⁇ 4C ie CH 3)2 - CHR 6 (CH 2 ) nX
  • R 5 may also be selected from a cyano-substituted dC 6 alkyl group;
  • 3 ⁇ 4R 5 can form a five or six ring
  • n is selected from an integer of 0 1-10;
  • X is selected from OR 7 SR 7 or R 7 R 8 ;
  • R 7 is selected from the group consisting of hydrogen, dC 6 alkyl, dC 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, dC 6 alkylcarbonyl, dC 3 haloalkylcarbonyl, C 2 -C 6 alkane Oxycarbonyl, phenylcarbonyl, dC 3 alkylsulfonyl, dC 3 haloalkylsulfonyl, phenylsulfonyl, dC 6 alkylamido, dC 6 alkylthioamido, phenylamido or benzene a thioamido group; the hydrogen on the ring of the phenyl group may be further substituted by the following groups: halogen,
  • Ql l Q12 Q13 Q14 is selected from hydrogen or CC 3 alkyl.
  • Preferred compounds in the present invention are:
  • A is selected from N or CH;
  • B is selected from the group consisting of hydrogen, halogen, cyano, dC 3 alkyl or halogenated dC 3 alkyl;
  • C is selected from hydrogen or halogen
  • R 2 is selected from halogen, CN, NO 2 , methylthio, methylsulfonyl, methoxycarbonyl, methylaminocarbonyl, ⁇ ⁇ unsubstituted or substituted by the following groups: methyl, dimethyl, Acetyl or mesyl;
  • R 3 is selected from halogen, dC 3 alkyl, halogenated dC 3 alkyl or halogenated dC 3 alkoxy;
  • R 5 is selected from CN, dC 4 alkyl, dC 3 haloalkyl group, _NHCH 2 CF 3, -. U, CH2C o 2 CH 3 -CH (C0 2 Et) 2, -CH 2 CH (OCH 3) 2 Or a CHR 6 (CH 2 ) nX ; when B is not hydrogen, R 5 may also be selected from a cyano-substituted dC 3 alkyl group;
  • Re is selected from hydrogen or methyl
  • n is selected from 0, an integer from 1 to 10;
  • X is selected from OR 7 , SR 7 , R 7 Rs;
  • R 7 is selected from the group consisting of hydrogen, dC 3 alkyl, C 3 -C 6 alkynyl, dC 3 alkylcarbonyl, dC 3 haloalkylcarbonyl, phenylcarbonyl, dC 3 alkylsulfonyl, phenylsulfonyl, dC 4 alkane Alkylamino, dC 4 alkylthioamido, phenylamido or phenylthioamido; the hydrogen on the ring of the phenyl group may be further substituted by the following groups: halogen, N0 2 , CN , C1-C3 alkyl, dC 3 haloalkyl, dC 3 alkoxy, dC 3 haloalkoxy; Q1-Q14 or one of the groups;
  • A is selected from N or CH;
  • B is selected from the group consisting of hydrogen, Cl, Br, cyano, dC 3 alkyl or halogenated dC 3 alkyl;
  • C is selected from the group consisting of hydrogen, Cl, Br or F; Ri is selected from Cl, Br, I or CH 3 ;
  • R 2 is selected from Cl, Br, I or CN
  • R 3 is selected from the group consisting of Cl, Br, CH 3 , CF 3 CH 2 0;
  • R4 is selected from hydrogen or CC 3 alkyl
  • R 5 is selected from the group consisting of CN, C1-C4 alkyl, CH 2 CF 3 -CH 2 CH 2 C1, -HCH 2 CF 3 _N ⁇ °, -CH 2 C0 2 CH 3
  • R 5 is also selected from CH 2 CN;
  • R6 is selected from hydrogen or methyl
  • n is selected from 0, an integer from 1 to 10;
  • X is selected from OR 7 , SR 7 , R 7 Rs;
  • R 7 is selected from the group consisting of hydrogen, dC 3 alkyl, propargyl, dC 3 alkylcarbonyl, dC 3 haloalkylcarbonyl, phenylcarbonyl, dC 3 alkylsulfonyl, phenylsulfonyl, dC 4 alkylamido, DC 4 alkylthioamido, phenylamido or phenylthioamido; the hydrogen on the ring of the phenyl group may be further substituted by the following groups:
  • A is selected from N or CH;
  • B is selected from the group consisting of hydrogen, Cl, cyano, CH 3 or CF 3 ;
  • C is selected from hydrogen or C1;
  • Ri is selected from C1 or CH 3 ;
  • R 2 is selected from Cl, Br or CN
  • R 3 is selected from CI or Br
  • R4 is selected from hydrogen or CC 3 alkyl
  • R 5 is selected from the group consisting of CN, dC 4 alkyl, CH 2 CF 3 , -CH 2 CH 2 C1, -HCH 2 CF 3 _N ⁇ °, -CH 2 C0 2 CH 3 ⁇ -CHR 6 (CH 2 )nX .
  • ⁇ is not hydrogen, R 5 may also be selected from CH 2 CN;
  • Re is selected from hydrogen or methyl
  • n is selected from 0, an integer from 1 to 10;
  • X is selected from OR 7 , SR 7 , R 7 Rs;
  • R 7 is selected from the group consisting of hydrogen, CrC 3 alkyl, propargyl, CH 3 CO, C1CH 2 C0, CH 3 S0 2 , C 2 H 5 S0 2 , phenylcarbonyl, phenylsulfonyl, formylamino, propyl Thioamido, phenylamido or phenylthioamido; the hydrogen on the ring of the phenyl group may be further substituted by a group: Cl, CF 3 , CF 3 O; or a Q 1 -Q 10 group One;
  • the number of substituents in the substituted amine group may be from 1 to 2.
  • Halogen refers to fluorine, chlorine, bromine or iodine.
  • Alkyl a linear or branched alkyl group such as methyl, ethyl, propyl, isopropyl or t-butyl.
  • Haloalkyl a straight or branched alkyl group in which a hydrogen atom may be partially or completely substituted by a halogen atom, for example, a haloalkyl group such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl Base, difluoromethyl or trifluoromethyl.
  • Alkenyl straight or branched and may have a double bond at any position, such as a vinyl or allyl group.
  • Alkynyl straight or branched and may have a triple bond at any position, such as ethynyl or propargyl.
  • a stereoisomer can be formed due to a carbon-carbon double bond and a carbon-nitrogen double bond connecting different substituents (different configurations are represented by Z and E, respectively).
  • the present invention includes Z-isomers and E-isomers and mixtures thereof in any ratio.
  • the invention may be illustrated by the compounds listed in the following tables, but does not limit the invention.
  • the compound of formula I can be prepared by reacting an oxazinone compound of the formula II with a substituted amine:
  • the reaction is carried out in a solvent, and is suitably selected from, for example, acetonitrile, tetrahydrofuran, diethyl ether, dichloromethane, chloroform, ethyl acetate, dioxane, toluene and the like.
  • Suitable bases may be selected from, for example, potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogencarbonate, triethylamine, pyridine, sodium methoxide, sodium ethoxide, sodium hydride, potassium t-butoxide or sodium t-butoxide.
  • the reaction temperature is between room temperature and the boiling point of the solvent, usually from 20 to 100 °C.
  • the reaction time is from 30 minutes to 20 hours, usually from 1 to 10 hours.
  • ⁇ ⁇ Formula II is a oxazinone compound prepared by reacting an anthranilic acid compound of the formula III with a carboxylic acid compound of the formula IV.
  • the anthranilic acid compound of the formula III can be obtained by a two-step reaction of an aromatic amine, and is referred to the following literature: Organic Syntheses, Coll. Vol. 10, p . 23 (2004) ; Vol . 79, p. 2002); Adv. Heterocycl. Chem. 1975, 18, 1-58; Journal of the Brazilian Chemical Society 2001, 12(3), 273-324; Angew.Chem.Int.Ed.Engl.1980, 19, 222- 223.
  • the compound of the formula I of the present invention exhibits high insecticidal activity against adults, larvae and eggs of harmful insects in the fields of agriculture, civil and animal technology. Some of the compounds showed better bactericidal activity. Accordingly, the present invention also encompasses the use of the compound of formula I as an insecticide and/or bactericide in agriculture and other fields.
  • the compounds of formula I are active against important pests of the following families and purposes: lepidopteran pests, stem borer, rice leaf roller, corn borer, tobacco leaf moth, small heartworm, diamondback moth, beet armyworm, twill night Moth and so on.
  • the present invention is more active against Plutella xylostella and Spodoptera exigua, and it can obtain good effects at very low doses; the present invention also has high activity against pests of the same wing, such as aphids; and at the same time, parts of the present invention
  • the compound also has good bactericidal activity and can be used for controlling rice blast, tomato late blight, vegetable gray mold, wheat powdery mildew, cucumber downy mildew, anthracnose, etc., especially for rice blast, cucumber downy mildew, Anthrax has good activity.
  • the compounds of formula I are less toxic to many beneficial insects and aphids, mammals, fish, birds, and are not phytotoxic.
  • the above compounds are advantageously used to protect important crops, livestock and stocks in the agricultural and horticultural industries, as well as the environment frequently experienced by humans from harmful insects and fungi.
  • the amount of the compound varies depending on various factors such as the compound to be used, the crop to be protected, the type of the pest, the degree of infection, the climatic conditions, the method of application, and the dosage form to be employed.
  • a dose of 10 grams to 1000 grams of compound per hectare provides adequate control.
  • a further object of the invention also relates to a method for controlling insects and/or phytopathogenic fungi in agricultural and horticulturally important crops and/or livestock and breeding stocks and/or environments frequented by humans by the application of the compounds of formula I .
  • the amount of the compound varies from 10 grams to 1000 grams per hectare.
  • composition comprising one or more compounds of formula I. Therefore, another object of the invention relates to insecticidal and insecticidal compounds containing one or more compounds of formula I as active ingredients
  • the active ingredient in the composition is present in an amount of from 0.1 to 99% by weight.
  • the composition may be used in the form of a dry powder, a wettable powder, an emulsifiable concentrate, a microemulsion, a paste, a granule, a solution, a suspension, etc.:
  • the choice of the type of composition depends on the particular application.
  • composition is prepared in a known manner, for example by diluting or dissolving the active substance with a solvent medium and/or a solid diluent, optionally in the presence of a surfactant.
  • Useful solid diluents or carriers are, for example: silica, kaolin, bentonite, talc, diatomaceous earth, dolomite, calcium carbonate, magnesium oxide, chalk, clay, synthetic silicate, attapulgite, sepiolite, etc. .
  • useful liquid diluents include, for example, aromatic organic solvents (mixtures of xylene or alkylbenzenes, chlorobenzene, etc.), paraffin (petroleum), alcohols (methanol, propanol, butanol, octane). Alcohol, glycerol), esters (ethyl acetate, isobutyl acetate, etc.), ketones (cyclohexanone, acetone, acetophenone, isophorone, ethyl amyl ketone, etc.), amides ( ⁇ , ⁇ -dimethylformamide, ⁇ -methylpyrrolidone, etc.).
  • aromatic organic solvents mixture of xylene or alkylbenzenes, chlorobenzene, etc.
  • paraffin paraffin
  • alcohols methanol, propanol, butanol, octane
  • Alcohol glycerol
  • esters ethyl acetate, is
  • Usable surfactants are sodium, calcium, triethylamine, such as alkyl sulfonates, alkyl aryl sulfonates, polyoxyethylene alkyl phenols, polyoxyethylene esters of sorbitol, lignosulfonates, and the like. Or triethanolamine salt.
  • composition may also contain special additives for specific purposes, such as containing a binder such as acacia, polyvinyl alcohol, polyvinylpyrrolidone and the like.
  • a binder such as acacia, polyvinyl alcohol, polyvinylpyrrolidone and the like.
  • the concentration of the active ingredient in the above composition may vary widely depending on the active ingredient, the purpose of use, the environmental conditions, and the type of preparation employed.
  • the concentration of the active ingredient is usually in the range of from 0.5 to 90%, preferably from 5 to 60%.
  • compositions may be added to the compositions, such as other acaricides/insecticides, fungicides, plant growth regulators, antibiotics, herbicides, fertilizers.
  • suspending agent The active ingredient content in the commonly used formula is 5% - 35%.
  • the water, the main drug, the dispersing agent, the suspending agent and the antifreezing agent are added to a sand mill and ground to prepare a suspension.
  • Preparation of water emulsion The original drug, solvent and emulsifier are added together to dissolve into a uniform oil phase. Water, antifreeze, and the like are mixed together to form a uniform aqueous phase. The aqueous phase is added to the oil phase or the oil phase is added to the aqueous phase under high-speed agitation to form a water emulsion having good dispersibility.
  • the aqueous emulsion active ingredient of the present invention is generally present in an amount of from 5% to 15%.
  • the compound of the present invention can be dissolved in one or several mixed solvents, and an emulsifier is added to enhance the dispersion of the compound in water.
  • Preparation of wettable powder According to the formulation requirements, the original drug, various surfactants and solid diluents are thoroughly mixed and pulverized by an ultrafine pulverizer to obtain a wettable property of a predetermined content (for example, 10% to 60%). Powder products.
  • the compound of the present invention can be combined with a finely divided solid powder such as clay, A mixture of organic silicates, carbonates, and wetting agents, binders, and/or dispersants.
  • Preparation of water-dispersible granules Mix and pulverize the original drug with powdered solid diluent, wetting spreader and binder, add water and knead, and then add it to a granulator equipped with a certain size sieve. Granulation, then drying and sieving (by screen area).
  • the original drug, dispersing agent, disintegrating agent and wetting agent and solid diluent may also be added to a sand mill, ground with water as a suspending agent, and then spray-dried and granulated, usually in a content of 20%. — 30% granulated product.
  • hydrazine - hydrazine 0.5 g was placed in a 50 ml reaction flask, 25 ml of acetonitrile was added, and 1 ml of aminoethanol was added thereto with stirring, and the mixture was heated under reflux for 15 hours.
  • 50 ml of saturated brine was poured into the reaction flask, and extracted with three times of 60 ml of ethyl acetate, dried, desolvated, and subjected to column chromatography to obtain a product of 0.40 g, that is, a compound. 2-2.
  • Example 3 Preparation of Compound 2-5 Take 0.5 g of 2-2 in a 50 ml reaction flask, add 25 ml of dichloromethane, and add 0.17 g of methanesulfonyl chloride and 0.11 g of triethylamine in dichloromethane under ice bath, and add to room temperature. Reaction for 15 hours. After the TLC monitoring reaction was completed, after decomposing under reduced pressure, the reaction flask was poured into 50 ml of saturated brine, extracted with three times of 60 ml of ethyl acetate, dried, desolvated, and subjected to column chromatography to obtain a product of 0.39 g. 2-5.
  • ⁇ -I 0.5 g of ⁇ -I was placed in a 50 ml reaction flask, 25 ml of acetonitrile was added, and 1 ml of ethylenediamine was added thereto with stirring, and the mixture was heated under reflux for 15 hours. After the TLC monitoring reaction was completed, after decomposing under reduced pressure, the reaction flask was poured into 50 ml of saturated brine, extracted with three times of 60 ml of ethyl acetate, dried, desolvated, and subjected to column chromatography to obtain a product of 0.38 g. 2-18.
  • Compound 2-70 Melting point 211-213 °C. Sppm 2.19(6H, s), 1.28(4H, s), 1.40(4H, s), 3.12(4H, s), 7.30(2H, s), 7.32(2H, s), 7.33(2H, s), 7.55(2H, s), 8.04(2H, d), 8.44(2H, s).
  • Compound 2-75 Melting point 212-214 ° C. ⁇ 2.16(6H, s), 1.24(6H, s), 1.25(6H, s), 1.41(4H, s), 3.30(4H, s), 7.27(2H, s), 7.37(2H, s), 7.50 (2H, m), 8.06 (2H, d), 8.23 (2H, m), 8.43 (2H, d).
  • Compound 2-77 Melting point 191-193 °C. ⁇ 1.60(2H, m), 2.17(6H, s), 3.10(4H, m), 7.30(2H, m), 7.33(2H, s), 7.48(2H, m), 7.58(2H, m), 8.14(2H, m), 8.47(2H, m).
  • Compound 2-80 5ppm 2.19(6H, s), 3.20(4H, m), 7.40(2H, s), 7.54(2H, s), 7.56(2H, m), 8.10(2H, d), 8.25( 2H, s), 8.45 (2H, d).
  • Compound 2-48 and other components are thoroughly mixed and pulverized by an ultrafine pulverizer to obtain a 30% wettable powder product.
  • the compound Table 2-71 and the other components are thoroughly mixed, and the thus obtained suspension concentrate is diluted with water to obtain a diluent of any desired concentration.
  • Example 8 60% water dispersible granules
  • Kaolin is made up to 100%
  • the compound 2-48 and the other components are mixed and pulverized, kneaded by water, and then granulated by a 10-100 mesh sieve granulator, followed by drying and sieving (screen size).
  • Example 9 Determination of insecticidal and acaricidal activity
  • test compound is dissolved in a mixed solvent of acetone/methanol (1:1), it is diluted with water containing 0.1% Tween 80 to a desired concentration.
  • the insecticidal activity was determined by airbrush spray method with P. xylostella, beet armyworm and cotton aphid as targets.
  • the cabbage leaves were punched into a 1 cm diameter leaf disc with a puncher.
  • the airbrush spray treatment pressure was 10 psi (about 0.7 kg/cm 2 ), and the spray was applied to the front and back of each leaf disc.
  • the spray volume was 0.5 ml.
  • 10 test insects (2 years old) were added per treatment, and each treatment was repeated 3 times. After the treatment, the cells were cultured at 24 ° C, relative humidity of 60% to 70%, and without light. After 96 hours, the number of viable animals was investigated, and the mortality was calculated.
  • the concentration of the chemical solution is 1 ppm
  • the mortality rate of 105 et al. was 100%.
  • the compounds 2-48, 2-71, 2-72 and the like have a mortality rate of more than 80% against beet armyworm.
  • the concentration of the chemical solution is 0.1 ppm
  • the mortality of the compounds 2-48, 2-71, 2-72 and the like against Spodoptera exigua is more than 60%.
  • Chlorpyramid, a control drug At a dose of 0.1 ppm, the mortality rate of Spodoptera exigua is 50%.
  • Chloramphenicol home made: melting point 229-230 ° C o 1H NMR (300 MHz, CDC1 3 ) ⁇ 10.10 (s, IH, Ph-H), 8.45 (dd, IH, Pyridin-6-H), 7.85 (dd , IH, Pyridin-4-H), 7.37 (dd, IH, Pyridin-5-H), 7.23 (d, IH, Ph-3-H), 7.21 (d, IH, Ph-5-H), 7.13 (s, IH, Pyrazole), 6.20 (d, IH, H), 2.94 (d, 3H, CH 3 ), 2.17 (s, 3H, Ph-CH 3 ).
  • the chemical structure is as follows:
  • the test method is as follows: Determination of in vitro bactericidal activity: The molten AEA medium is cooled to 60 ° C to 70 ° C, and the quantitative agent is added according to the set concentration to prepare a toxic medium containing different doses. After it was sufficiently cooled, the inoculum of 0.5 cm in diameter was inoculated and placed in an incubator for cultivation. The culture was carried out for 10 days in an incubator, and the growth diameter of each treated colony was measured and the inhibition rate was calculated.
  • Determination of in vivo protective activity A live pot assay was used. The test compound was first dissolved in a small amount of acetone and diluted to the desired concentration with water containing 0.1% Tween 80. The spray was applied to the plant test material, and the disease was inoculated 24 hours later. After inoculation, place the plants in a constant temperature and humidity incubator to continue the infection, after the control is fully ill (usually Conduct an assessment survey for a week).
  • In vitro antibacterial activity assay When the concentration of the drug solution is 25 ppm, the inhibition rate of rice blast by compounds 1-4, 2-10, 2-18, 2-31, etc. is more than 50%. The inhibition rate of rice blast with the control agent chlorantranil at 25 ppm was . .
  • the control agent chlorantranil had a control effect on cucumber downy mildew and anthracnose at a dose of 400 ppm.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

L'invention porte sur des composés anthranilamides représentés par la formule I, possédant une activité insecticide à large spectre. Les substituants dans la formule I sont tels que définis dans la description. A dose faible, les présents composés possèdent une bonne activité contre les lépidoptères nuisibles : pyrale du maïs, pyrale de la canne à sucre, pyrale tordeuse de la pomme, tordeuse des bourgeons de la pomme, lymantride, pyrale des herbes, pyrale du maïs, pyrale du tabac, petite tordeuse des bourgeons, petite mite plutellidae, légionnaire de la betterave, légionnaire asiatique et similaires, notamment la petite mite plutellidae et le légionnaire de la betterave. Les présents composés ont également une activité élevée contre les nuisibles homoptères, comme les pucerons. De plus, certains desdits composés ont une activité puissante comme bactéricides et peuvent être utiles dans la lutte contre la pyriculariose du riz, le mildiou de la tomate, le mildiou du concombre et la pourriture grise des légumes.
PCT/CN2008/070832 2007-04-30 2008-04-28 Composés anthranilamides et leur utilisation WO2008134970A1 (fr)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
CN2007100111786A CN101298435B (zh) 2007-04-30 2007-04-30 邻甲酰氨基苯甲酰胺类化合物及其应用
CN200710011178.6 2007-04-30
CN 200710011176 CN101298451B (zh) 2007-04-30 2007-04-30 苯甲酰胺类化合物及其应用
CN200710011176.7 2007-04-30
CN2008100571021A CN101497602B (zh) 2008-01-30 2008-01-30 邻氨基苯甲酸类化合物及其应用
CN200810057102.1 2008-01-30

Publications (1)

Publication Number Publication Date
WO2008134970A1 true WO2008134970A1 (fr) 2008-11-13

Family

ID=39943130

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CN2008/070832 WO2008134970A1 (fr) 2007-04-30 2008-04-28 Composés anthranilamides et leur utilisation

Country Status (1)

Country Link
WO (1) WO2008134970A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010003350A1 (fr) * 2008-07-07 2010-01-14 中国中化集团公司 Composés pyridyl-pyrazolylamides 1-substitués et leurs utilisations
WO2013136073A1 (fr) * 2012-03-13 2013-09-19 Redx Pharma Limited Produits chimiques agricoles
CN107056747A (zh) * 2017-03-31 2017-08-18 湖北省生物农药工程研究中心 含α‑氨基酮结构的酰胺衍生物及其制备方法和用途
CN108333186A (zh) * 2018-04-03 2018-07-27 南京理工大学 基于烟垛表面的霉变检测系统及其检测方法

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1419537A (zh) * 2000-03-22 2003-05-21 纳幕尔杜邦公司 杀虫的邻氨基苯甲酰胺
CN1541063A (zh) * 2001-08-13 2004-10-27 ��Ļ���Ű˾ 使用邻氨基苯甲酰胺化合物防治特殊害虫的方法
CN1653051A (zh) * 2001-08-16 2005-08-10 纳幕尔杜邦公司 防治无脊椎害虫的取代的邻氨基苯甲酰胺类化合物
CN1703417A (zh) * 2002-10-04 2005-11-30 纳幕尔杜邦公司 邻氨基苯甲酰胺杀虫剂
WO2005118552A2 (fr) * 2004-04-13 2005-12-15 E.I. Dupont De Nemours And Company Insecticides a base d'anthranilamides
CN1713819A (zh) * 2001-09-21 2005-12-28 杜邦公司 邻氨基苯甲酰胺杀节肢动物处理

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1419537A (zh) * 2000-03-22 2003-05-21 纳幕尔杜邦公司 杀虫的邻氨基苯甲酰胺
CN1541063A (zh) * 2001-08-13 2004-10-27 ��Ļ���Ű˾ 使用邻氨基苯甲酰胺化合物防治特殊害虫的方法
CN1653051A (zh) * 2001-08-16 2005-08-10 纳幕尔杜邦公司 防治无脊椎害虫的取代的邻氨基苯甲酰胺类化合物
CN1713819A (zh) * 2001-09-21 2005-12-28 杜邦公司 邻氨基苯甲酰胺杀节肢动物处理
CN1703417A (zh) * 2002-10-04 2005-11-30 纳幕尔杜邦公司 邻氨基苯甲酰胺杀虫剂
WO2005118552A2 (fr) * 2004-04-13 2005-12-15 E.I. Dupont De Nemours And Company Insecticides a base d'anthranilamides

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CHAI BAOSHAN ET AL.: "Recent advance on novel insecticidal anthranilic diamides", AGROCHEMICALS, vol. 46, no. 3, March 2007 (2007-03-01), pages 148 - 153 *

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010003350A1 (fr) * 2008-07-07 2010-01-14 中国中化集团公司 Composés pyridyl-pyrazolylamides 1-substitués et leurs utilisations
US20110046186A1 (en) * 2008-07-07 2011-02-24 Bin Li 1-Substituted Pyridyl-Pyrazolyl Amide Compounds and Uses Thereof
US8492409B2 (en) * 2008-07-07 2013-07-23 Sinochem Corporation 1-substituted pyridyl-pyrazolyl amide compounds and uses thereof
WO2013136073A1 (fr) * 2012-03-13 2013-09-19 Redx Pharma Limited Produits chimiques agricoles
CN107056747A (zh) * 2017-03-31 2017-08-18 湖北省生物农药工程研究中心 含α‑氨基酮结构的酰胺衍生物及其制备方法和用途
CN107056747B (zh) * 2017-03-31 2020-05-15 湖北省生物农药工程研究中心 含α-氨基酮结构的酰胺衍生物及其制备方法和用途
CN108333186A (zh) * 2018-04-03 2018-07-27 南京理工大学 基于烟垛表面的霉变检测系统及其检测方法

Similar Documents

Publication Publication Date Title
WO2010060379A1 (fr) Composés éther avec un hétérocycle à 5 chaînons contenant de l’azote et utilisations de ceux-ci
CN101298435B (zh) 邻甲酰氨基苯甲酰胺类化合物及其应用
JP5183735B2 (ja) 置換ピリミジンエーテル化合物及びそれらの使用
CN101747306B (zh) 取代醚类化合物及其应用
WO2016095768A1 (fr) Composé d'urée de pyrimidine contenant des isoxazolines et son utilisation
CN108314656B (zh) 不饱和烃嘧啶硫醚类化合物及其制备方法与应用
WO2009146648A1 (fr) Composés amides, leurs procédés de fabrication et leurs utilisations
JP5678200B2 (ja) アリールオキシジハロプロペニルエーテル化合物及びその使用
CN101875639A (zh) 取代嘧啶醚类化合物及其应用
WO2008134970A1 (fr) Composés anthranilamides et leur utilisation
CN102690257A (zh) 一种邻氨基苯甲酰胺化合物及其应用
CN119059936A (zh) 间胺基苯甲酸双酰胺类化合物
CN109232534B (zh) 含杂环二芳胺基吡唑甲酰胺类化合物及其制备方法与应用
CN113549053B (zh) 一种吡唑喹（唑）啉醚类化合物及其应用
CN104725276B (zh) 一种含七氟异丙基的羰基肟醚类化合物、其制备方法及应用
CN102911131B (zh) 一种双键桥三氟甲基异噁唑类化合物、其制备方法及应用
CN105777640B (zh) 一种吡唑环己二醇醚类化合物及其应用
CN110194742B (zh) 取代（杂）芳基亚甲基吡唑醚类化合物及其制备方法与应用
JPS61243078A (ja) ピリダジノン誘導体，その製造法および殺虫・殺ダニ・殺線虫・殺菌剤
JP3711581B2 (ja) セミカルバゾン誘導体及び有害生物防除剤
CN110194747B (zh) 取代（杂）芳基亚甲基嘧啶醚类化合物及其制备方法与应用
CN108976167B (zh) 一种取代苯肼类化合物及其应用
CN106810545A (zh) 一种杂环酰基亚胺噻唑类化合物、其制备方法及应用
CN115232083A (zh) 取代异噁唑乙胺类化合物及其制备方法和用途
JPH06157562A (ja) 有機リン化合物、その製造法および該化合物を含有する殺虫、殺ダニ、殺線虫剤

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 08734190

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 08734190

Country of ref document: EP

Kind code of ref document: A1

点击 这是indexloc提供的php浏览器服务，不要输入任何密码和下载