WO2021023292A1 - Composé de pyrazolyl pyrazole substitué ou sel ou composition pesticide acceptable de celui-ci et utilisation associée - Google Patents

Composé de pyrazolyl pyrazole substitué ou sel ou composition pesticide acceptable de celui-ci et utilisation associée Download PDF

Info

Publication number
WO2021023292A1
WO2021023292A1 PCT/CN2020/107700 CN2020107700W WO2021023292A1 WO 2021023292 A1 WO2021023292 A1 WO 2021023292A1 CN 2020107700 W CN2020107700 W CN 2020107700W WO 2021023292 A1 WO2021023292 A1 WO 2021023292A1
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
alkoxy
substituted
halogen
group
Prior art date
Application number
PCT/CN2020/107700
Other languages
English (en)
Chinese (zh)
Inventor
葛家成
杨春河
邢阳阳
马娥
刘明东
李丽
胡堂路
Original Assignee
海利尔药业集团股份有限公司
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
Application filed by 海利尔药业集团股份有限公司 filed Critical 海利尔药业集团股份有限公司
Publication of WO2021023292A1 publication Critical patent/WO2021023292A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • 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
    • 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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system

Definitions

  • the present invention belongs to the technical field of pesticides, and specifically relates to a substituted pyrazolylpyrazole bisamide compound or its acceptable salt and composition as a pesticide, and relates to these compounds or their acceptable salt and composition as pesticides. Use of herbicides.
  • the present invention provides a substituted pyrazolylpyrazole bisamide compound or its acceptable salt as a pesticide, a composition and its use.
  • the above-mentioned pyrazolylpyrazole bisamide-based compounds or their acceptable salts as pesticides have higher herbicidal activity than known compounds, especially for common weeds in paddy fields, they have excellent herbicidal activity, and It has relatively better selectivity and crop safety.
  • R 1 represents H or halogen
  • R 2 represents H, halogen, CN, NO 2 or COOR 1 ;
  • R 3 represents H, halogen, CN, C 1 -C 6 alkyl, halo C 1 -C 6 alkyl, C 1 -C 6 alkoxy or halo C 1 -C 6 alkoxy;
  • R 4 represents H, halogen, CN, C 1 -C 6 alkyl, halogenated C 1 -C 6 alkyl, C 1 -C 6 alkoxy, halogenated C 1 -C 6 alkoxy, C 1- C 6 alkyl substituted sulfonyl, halo C 1 -C 6 alkyl substituted sulfonyl;
  • R 5 represents H, halogen, CN, C 1 -C 6 alkyl, halogenated C 1 -C 6 alkyl, C 1 -C 6 alkoxy, halogenated C 1 -C 6 alkoxy, C 3- C 6 cycloalkyl, C 3 -C 6 cycloalkyloxy, C 3 -C 6 heterocyclyl, C 3 -C 6 heterocyclyloxy, C 3 -C 6 cycloalkyl substituted C 1- C 6 alkyl, C 3 -C 6 cycloalkenyl substituted C 1 -C 6 alkyl and, unsubstituted or by 1-5 independently selected from C 1 -C 6 alkyl, halogenated C 1 -C 6 alkyl group, C 1 -C 6 alkoxy group, halogenated C 1 -C 6 alkoxy group, C 1 -C 6 alkyl carbonyl group, halogenated C 1 -C 6 alkyl carbonyl group, C 1
  • R 4 and R 5 together form a five-membered or six-membered saturated or unsaturated ring that is unsubstituted or substituted by any substituent;
  • R 6 represents H, halogen, CN, C 1 -C 6 alkyl, halo C 1 -C 6 alkyl, C 1 -C 6 alkoxy, or halo C 1 -C 6 alkoxy.
  • R 1 represents H or halogen
  • R 2 represents H, halogen, CN, NO 2 ;
  • R 3 represents H, halogen, CN, C 1 -C 6 alkyl, halo C 1 -C 6 alkyl;
  • R 4 represents H, halogen, CN, C 1 -C 6 alkyl, halo C 1 -C 6 alkyl, C 1 -C 6 alkoxy, halo C 1 -C 6 alkoxy;
  • R 5 represents H, halogen, CN, C 1 -C 6 alkyl, halogenated C 1 -C 6 alkyl, C 1 -C 6 alkoxy, halogenated C 1 -C 6 alkoxy, C 3- C 6 cycloalkyl, C 3 -C 6 heterocyclyl, C 3 -C 6 cycloalkyl substituted C 1 -C 6 alkyl, C 3 -C 6 cycloalkenyl substituted C 1 -C 6 alkyl And, unsubstituted or 1-5 independently selected from C 1 -C 6 alkyl, halo C 1 -C 6 alkyl, C 1 -C 6 alkoxy, halo C 1 -C 6 alkoxy Group, C 3 -C 6 cycloalkyl, halo C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyloxy, halogen, nitro, cyano, carboxy, aldehyde or
  • R 4 and R 5 together constitute unsubstituted or are selected from H, halogen, CN, C 1 -C 6 alkyl, halo C 1 -C 6 alkyl, C 1 -C 6 alkoxy, halogen Substituted C 1 -C 6 alkoxy, C 3 -C 6 cycloalkyl, C 3 -C 6 heterocyclic group substituted by a five-membered or six-membered saturated or unsaturated ring, said five-membered Or the six-membered saturated or unsaturated ring contains or does not contain one or more of O, N and S;
  • R 6 represents H, halogen, CN, C 1 -C 6 alkyl, halo C 1 -C 6 alkyl, C 1 -C 6 alkoxy, or halo C 1 -C 6 alkoxy.
  • R 1 represents H or halogen
  • R 2 represents H, halogen, CN, NO 2 ;
  • R 3 represents H, halogen, CN, C 1 -C 4 alkyl, halo C 1 -C 4 alkyl;
  • R 4 represents H, halogen, CN, C 1 -C 4 alkyl, halo C 1 -C 4 alkyl;
  • R 5 represents H, halogen, CN, C 1 -C 4 alkyl, halogenated C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halogenated C 1 -C 4 alkoxy, C 3- C 6 cycloalkyl, C 3 -C 6 heterocyclyl, C 3 -C 6 cycloalkyl substituted C 1 -C 4 alkyl, C 3 -C 6 cycloalkenyl substituted C 1 -C 4 alkyl And, unsubstituted or 1-5 independently selected from C 1 -C 4 alkyl, halo C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halo C 1 -C 4 alkoxy The aryl or heteroaryl substituted by the group in the group;
  • R 4 and R 5 together form an unsubstituted five-membered or six-membered saturated or unsaturated ring, and the five-membered or six-membered saturated or unsaturated ring contains one or more of O, N, and S.
  • R 6 represents H, halogen, CN, C 1 -C 4 alkyl, or halogenated C 1 -C 4 alkyl.
  • the aryl group is phenyl or naphthyl
  • the heteroaryl group is pyridyl, pyrazolyl, pyrimidinyl, thiazolyl, isoxazolyl, thienyl, furyl, Pyrrolyl, imidazolyl, pyranyl, pyrazinyl, pyridazinyl, triazinyl.
  • R 1 represents H or halogen
  • R 2 represents H, halogen or CN
  • R 3 represents H, C 1 -C 4 alkyl or halo C 1 -C 4 alkyl
  • R 4 represents H, C 1 -C 4 alkyl or halo C 1 -C 4 alkyl
  • R 5 represents H, C 1 -C 4 alkyl, halogenated C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 3 -C 6 cycloalkyl, C 3 -C 6 heterocyclic group, C 3 -C 6 cycloalkyl substituted C 1 -C 4 alkyl, C 3 -C 6 cycloalkenyl substituted C 1 -C 4 alkyl and, unsubstituted or 1-3 independently selected from C An aryl or heteroaryl group substituted by a group in a 1- C 4 alkyl group or a halogenated C 1 -C 4 alkyl group, wherein the aryl group is a phenyl group, and the heteroaryl group is a pyridyl group or a pyrazolyl group , Pyrimidinyl, thiazolyl, isoxazolyl or thienyl;
  • R 4 and R 5 together form an unsubstituted five-membered or six-membered saturated or unsaturated ring, and the unsubstituted five-membered or six-membered saturated or unsaturated ring contains O and/or N;
  • R 4 and R 5 are connected to form an unsubstituted 5-membered or 6-membered saturated or unsaturated ring
  • R 6 represents H, C 1 -C 4 alkyl, or halogenated C 1 -C 4 alkyl.
  • R 1 represents H, F, Cl or Br
  • R 2 represents H, CN
  • R 3 represents H, Me, Et, CHF 2 , CH 2 F, CF 3 , CH 2 CF 3 ;
  • R 4 represents H, Me, Et
  • R 5 represents H, Me, Et, n-Pr, i-Pr, n-Bu, i-Bu, s-Bu, t-Bu, CH 2 Cl, CHF 2 , CH 2 F, CF 3 , CH 2 CF 3.
  • R 4 and R 5 together form a morpholino group
  • R 6 represents H, H, Me, Et, n-Pr, i-Pr.
  • the pesticide acceptable salt may be a salt prepared by reacting the substituted pyrazolylpyrazole bisamide compound of the present invention with a chemically acceptable acid, wherein the chemically acceptable acid may be an inorganic acid (such as hydrochloric acid, sulfuric acid, phosphoric acid, or hydrobromic acid, etc.) or organic acids (such as oxalic acid, maleic acid, fumaric acid, malic acid, tartaric acid, citric acid or benzoic acid, etc.); the pesticide acceptable salt can also It is a salt prepared by reacting a substituted pyrazolylpyrazole bisamide compound of the present invention with a chemically acceptable base, wherein the chemically acceptable base may be an inorganic base (such as sodium hydroxide, potassium hydroxide, Calcium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate or potassium bicarbonate) or organic bases (such as trimethylamine, triethylamine, etc.).
  • a chemically acceptable acid may be an inorganic acid (such
  • the pesticide acceptable salt can be potassium salt, sodium salt, ammonium salt, calcium salt, pyridine salt or choline salt.
  • the present invention also discloses a herbicidal composition, which comprises a herbicidal effective amount of the substituted pyrazolylpyrazole bisamide compound as described above or at least one of its acceptable salts as pesticides.
  • it also includes a preparation carrier or a preparation auxiliary.
  • the present invention also discloses a method for controlling undesired plants, which comprises adding a herbicidal effective amount of the above substituted pyrazolylpyrazole bisamide compound or at least one of the above-mentioned substituted pyrazolyl pyrazole bisamide compounds or their acceptable salts as pesticides.
  • the herbicidal composition as described above is used on unwanted plants.
  • the present invention also discloses the use of the above-mentioned substituted pyrazolylpyrazole bisamide compound or at least one of its acceptable salts as pesticides or the above-mentioned herbicidal composition for controlling harmful plants.
  • C 1 -C 6 alkyl group a straight or branched chain alkyl group having 1 to 6 carbon atoms, such as methyl, ethyl, propyl, isopropyl or n-butyl, isobutyl, sec-butyl, Tert-butyl etc.
  • Halogen or halogen refers to fluorine, chlorine, bromine, and iodine.
  • Halogenated C 1 -C 6 alkyl groups linear or branched alkyl groups with 1-6 carbon atoms.
  • the hydrogen atoms on these alkyl groups may be partially or completely replaced by halogens, for example, chloromethyl, dichloromethane Chloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, etc.
  • C 1 -C 6 alkoxy group a straight or branched chain alkyl group having 1 to 6 carbon atoms, connected to the structure via an oxygen atom bond.
  • Halogenated C 1 -C 6 alkoxy groups straight or branched chain alkoxy groups having 1 to 6 carbon atoms.
  • the hydrogen atoms on these alkoxy groups may be partially or completely replaced by halogens, for example, chloroform Oxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, trifluoroethoxy, etc.
  • C 1 -C 6 Alkylcarbonyl A group formed by connecting an alkyl group with 1 to 6 carbon atoms and a carbonyl group, such as
  • C 1 -C 6 alkylsulfonyl group a group formed by connecting an alkyl group with 1-6 carbon atoms and a sulfonyl group, such as
  • C 1 -C 6 alkoxy substituted C 1 -C 6 alkoxy group A group substituted with an alkoxy group having 1 to 6 carbon atoms as a substituent of an alkoxy group having 1 to 6 carbon atoms Group, such as
  • Aryl any functional group or substituent derived from a simple aromatic ring.
  • Heteroaryl a polycyclic ring containing one or more N, O, S heteroatoms, such as pyridine, furan, thiophene, pyrazole, pyrimidine, pyrazine, pyridazine, triazine, thiazole, etc.
  • Bucyclic group a group consisting of bicyclic or tricyclic rings, such as
  • the method for synthesizing the compound of formula I is specifically combining the compound of formula II and the compound of formula III (in the following chemical formulas, unless otherwise defined, the substituents and symbols are the same as those defined in formula I Significance)
  • the intermediate is obtained after the reaction is carried out with or without solvent, and then reacted with the compound of formula IV to obtain the target compound of formula I.
  • the compound represented by formula II can be synthesized with reference to the method described in patent CN1036397C, and the compound represented by formula III and IV can be obtained commercially:
  • the solvent is selected from acetonitrile, N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, tetrahydrofuran, dichloromethane, benzene, toluene, xylene, dichloroethane , One or more solvents in ethyl acetate.
  • the compound of formula I of the present invention has outstanding herbicidal activity.
  • the active substance of the present invention is also effective against perennial weeds which grow from rhizomes, rhizomes, or other perennial organs.
  • the timing of use of the active substance of the present invention it may be before sowing, before germination or after germination.
  • weed species for which the active substance of the present invention can play an effective role include monocots: annual oats, ryegrass, Look at the genus Aegilops, Barnyard, Crabgrass, Setaria and Cyperus, and the perennial Wheatgrass, Bermudagrass, Imperata and Sorghum, and the perennial Cyperus.
  • the active substance of the present invention can still effectively control harmful plants, such as barnyardgrass, Aquilaria, Alisma, water chestnut, saccharum and Cyperus under the specific conditions of rice sowing.
  • the seedling of the weed can be prevented completely before the weed grows, or the growth of the weed can be stopped when the cotyledon grows, and finally died completely after three to four weeks.
  • the compound of the present invention has excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, it has no damage to important economic crop plants such as wheat, barley, rye, rice, corn, sugar beet, cotton and soybean, or The damage is very small. Therefore, the compound of the present invention is very suitable for selectively controlling useless plants in agricultural crops or ornamental plants. In addition, the compounds of the present invention can significantly regulate the growth of crop plants.
  • these compounds By regulating the involvement of plant metabolism, these compounds are used to control plant components and promote harvest, such as drying and stunting plant growth. And they are also suitable for regulating and inhibiting the growth of undesirable plants without destroying the growth of crops. Inhibiting plant growth plays a very important role in many monocot and dicot crops, because it can reduce or completely prevent lodging.
  • the present invention also provides herbicidal compositions comprising the compound of formula I.
  • the compound of formula I can be formulated in a variety of ways.
  • Suitable formulation choices are: wettable powder (WP), wettable liquid (SL), soluble powder (SP), dispersible liquid (DC), water (AS), microemulsion (ME), emulsifiable concentrate (EC), water emulsion (EW), sprayable solution, suspension (SC), dispersible oil suspension (OD), powder (DP), microcapsule suspension (CS), water dispersible granules (WG), water soluble Granules (SG), large granules (GG), granules (GR) for broadcast and soil application, aerosols (AE), ultra-low volume agents (ULV) and wax products.
  • Necessary formulation aids such as inert substances, surfactants, solvents and other additives.
  • the suitable active material that can be mixed with the active material of the present invention is, for example, the known material in the "Encyclopedia of World Pesticide New Variety Technology” (China Agricultural Science and Technology Press, 2010.9).
  • the herbicide active substances mentioned below can be mixed with the mixture of formula I, (Note: the name of the compound, or the common name according to the International Organization for Standardization (ISO), or the chemical name, with the code when appropriate): Amine, Butachlor, Alachlor, Propolachlor, Metolachlor, Fine Metolachlor, Pretilachlor, Tetrachlor, Mesochlor, Naprolam, R-Naproxen Mefenacet, propanyl, mefenacet, difenacet, diflufenican, chlorfenazone, flufenacet, bromobutyramide, dimethenamid, high-efficiency dimethyl Thienachlor, ethoxyfen, flufenacet, metolachlor, metazachlor, clomazone, high-efficiency wheat straw fluoromethyl, high-efficiency wheat straw fluorine propyl ester, propenyl chlor, clethamine , Butachlor, cyprofen
  • the active compound has good activity and selectivity especially against common weeds in paddy fields, and has excellent crop safety for paddy field crops, especially rice.
  • the method for preparing the compound of the present invention is illustrated in the following technical scheme and examples.
  • the raw materials can be purchased on the market or can be prepared by methods known in the literature or as shown in the detailed description.
  • Those skilled in the art should understand that other synthetic routes can also be used to synthesize the compounds of the present invention.
  • the specific raw materials and conditions in the synthetic route have been described in the following, they can be easily replaced with other similar raw materials and conditions.
  • These modifications or variations of the preparation method of the present invention produce such compounds as Various isomers and the like are included in the scope of the present invention.
  • the preparation method described below can be further modified according to the disclosure of the present invention using conventional chemical methods well known to those skilled in the art. For example, protecting appropriate groups during the reaction and so on.
  • Powder 20% of the compound of formula (I) is weighed, 80% of kaolin is mixed uniformly, and the product is obtained by pulverization.
  • Wettable powder weigh 20% of the compound of formula (I), 8% calcium lignosulfonate, 2% sodium lauryl sulfate, 3% white carbon black, and kaolin and add to 100%. The mixture is evenly mixed and the product is obtained after air jet pulverization.
  • Water dispersible granules weigh 60% of the compound of formula (I), 6% sodium lignosulfonate, 4% NNO (alkyl naphthalene sulfonate formaldehyde condensate), 2% open powder BX (dibutyl Sodium naphthalene sulfonate), 3% K-12 (sodium lauryl sulfate), 5% carboxymethyl (ethyl) cellulose, 5% diatomaceous earth, 5% glucose, and kaolin are added to 100%. The mixture is evenly mixed, after being pulverized by air flow, the powder is weighed and mixed with water, granulated in a granulator, then dried and sieved to obtain a granular product.
  • NNO alkyl naphthalene sulfonate formaldehyde condensate
  • BX dibutyl Sodium naphthalene sulfonate
  • K-12 sodium lauryl sulf
  • Emulsifiable concentrate weigh 15% of the compound of formula (I), 5% Nongru 700#, 5% Nongru 500#, 6% Nongru 1601#, 10% cyclohexanone, 3% N-methylpyrrolidone, Solvent oil 150 is added to 100%, and the product is obtained by dissolving completely and mixing uniformly.
  • Suspending agent weigh 15% of the compound of formula (I), 4% FS3000 (phosphate ester type anionic surfactant), 2% NS-500LQ (non-ionic hydroxyl polyethylene oxide block copolymer), 0.2% xanthan gum, 1% magnesium aluminum silicate, 5% ethylene glycol, 0.1% BIT (1,2-benzisothiazolin-3-one), 0.3% organically modified siloxane defoamer, The deionized water is added to 100% to form a slurry, and the product is obtained after sanding.
  • the original drug of the test compound is dissolved in DMF to prepare a 2.5% mother liquor, and then diluted with 0.1% Tween-80 water for use.
  • Sprinkle the target seeds (barnyard grass, amaranthus retroflexus) into it, cover with soil 0.5-1 cm after sowing, and place the bottom in a greenhouse after absorbing water for cultivation.
  • Amaranth 3-4 leaf stage and barnyard grass grow to 2-3 leaf stage, the stems and leaves were sprayed with a spray tower according to the designed dose of the experiment, and the experiment was set up to repeat 3 times.
  • Grade 9 equivalent to 67.6-100% of the weeds in the blank control area
  • Grade 8 equivalent to 35.1-67.5% of the weeds in the blank control area
  • Grade 5 equivalent to 10.1-15% of weeds in the blank control area
  • Level 4 equivalent to 5.1-10% of weeds in the blank control area
  • Level 3 equivalent to 2.6-5% of the weeds in the blank control area
  • Level 2 equivalent to 0-2.5% of weeds in the blank control area
  • Pafenpyril (specific structure is ),
  • Control compound 4.179 (documented in CN1036397C, the specific structure is ),
  • Control compound 4.238 (documented in CN1036397C, the specific structure is ),
  • Control compound 4.254 (documented in CN1036397C, the specific structure is ),
  • the protected compound of the present invention has excellent biological activity and has good commercial application prospects.
  • the original drug of the test compound is dissolved in DMF, and then diluted with water containing 0.1% Tween 80 to the desired concentration. Prepare the special soil for paddy field and install it to 3/4 of the flowerpots with 11cm diameter, 7cm bottom diameter and 11cm high plastic opaque flowerpots. Add 120mL of water to each flowerpot, mix the soil and water evenly and keep the surface flat .
  • Grade 8 equivalent to 35.1-67.5% of the weeds in the blank control area
  • Grade 5 equivalent to 10.1-15% of weeds in the blank control area
  • Level 4 equivalent to 5.1-10% of weeds in the blank control area
  • Level 3 equivalent to 2.6-5% of the weeds in the blank control area
  • Level 2 equivalent to 0-2.5% of weeds in the blank control area
  • the main symptoms of phytotoxicity are:
  • the compound protected by the present invention has excellent biological activity of paddy field weeds, has a good effect on common weeds in paddy fields, and has good commercial application prospects; in addition, the current dosage is
  • the compound protected by the present invention is basically non-phytotoxic (the degree of phytotoxicity is 0) or no obvious phytotoxicity (the degree of phytotoxicity is 1-10%) for rice visual observation, so it is especially effective for crops at a suitable dosage Rice has good safety.
  • the original drug of the test compound is dissolved in DMF to prepare a 2.5% mother liquor, and then diluted with 0.1% Tween-80 water for use.
  • Sprinkle the target seeds (barnyard grass, amaranthus retroflexus) into it, cover with soil 0.5-1 cm after sowing, and place the bottom in a greenhouse after absorbing water for cultivation.
  • Amaranth 3-4 leaf stage, barnyardgrass grow to 2-3 leaf stage, the stem and leaves were sprayed with a spray tower according to the designed dose of the experiment, and the experiment was set up to 3 times.
  • the liquid After the liquid is naturally air-dried, it is placed in a greenhouse for management according to conventional methods, and the growth and development of the test materials are regularly observed. According to Part 8 of the Guidelines for Pesticide Indoor Bioassay Tests, and according to the actual situation, the supply is regularly inspected by visual inspection after treatment. The effect of the test agent on crops, and the symptoms of phytotoxicity are described. The main symptoms are:
  • Grade b the degree of phytotoxicity is 1-10%, no obvious phytotoxicity
  • Grade c the degree of phytotoxicity is 11-30%, slight phytotoxicity
  • Grade d the degree of phytotoxicity is 31-50%, moderate phytotoxicity
  • the compound protected by the present invention has basically no phytotoxicity or no obvious phytotoxicity to wheat or corn by visual observation under the current dosage. Therefore, it is very good for crops, especially wheat or corn, at a suitable dosage. safety.
  • the compounds of the present invention can be used as selective herbicides in gramineous crop fields or rice fields.

Landscapes

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

Abstract

La présente invention se rapporte au domaine des pesticides, et concerne en particulier un composé de pyrazolyl pyrazole bisamide substitué ou un sel ou composition pesticide acceptable de celui-ci et une utilisation associée. Le composé a la structure de formule (I) : Chaque groupe dans la formule est tel que défini dans la description. Le composé ayant une structure de pyrazolyl pyrazole bisamide substitué selon la présente invention possède des activités herbicides supérieures à celles des composés connus, et présente en particulier d'excellentes activités herbicides vis-à-vis des mauvaises herbes communes dans les rizières.
PCT/CN2020/107700 2019-08-07 2020-08-07 Composé de pyrazolyl pyrazole substitué ou sel ou composition pesticide acceptable de celui-ci et utilisation associée WO2021023292A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN201910725301.3 2019-08-07
CN201910725301.3A CN112341456B (zh) 2019-08-07 2019-08-07 一种取代的吡唑基吡唑双酰胺类化合物或其作为农药可接受的盐、组合物及其用途

Publications (1)

Publication Number Publication Date
WO2021023292A1 true WO2021023292A1 (fr) 2021-02-11

Family

ID=74366596

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CN2020/107700 WO2021023292A1 (fr) 2019-08-07 2020-08-07 Composé de pyrazolyl pyrazole substitué ou sel ou composition pesticide acceptable de celui-ci et utilisation associée

Country Status (2)

Country Link
CN (1) CN112341456B (fr)
WO (1) WO2021023292A1 (fr)

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4711658A (en) * 1985-12-05 1987-12-08 Bayer Aktiengesellschaft 5-perfluoroacylamino-4-nitro-1-arylpyrazole salts, plant growth regulating and herbicidal composition containing them, and plant growth regulating and herbicidal method of using them
CN1036397C (zh) * 1992-10-12 1997-11-12 先灵公司 新的取代的吡唑衍生物
WO2016121900A1 (fr) * 2015-01-30 2016-08-04 協友アグリ株式会社 Composition herbicide
WO2016121898A1 (fr) * 2015-01-30 2016-08-04 協友アグリ株式会社 Composition herbicide
CN107108621A (zh) * 2015-01-23 2017-08-29 协友株式会社 经取代的吡唑基吡唑衍生物及其作为除草剂的应用
JP2018016573A (ja) * 2016-07-27 2018-02-01 協友アグリ株式会社 除草剤組成物

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6128556B2 (ja) * 2013-08-13 2017-05-17 協友アグリ株式会社 置換ピラゾリルピラゾール誘導体とその除草剤としての使用

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4711658A (en) * 1985-12-05 1987-12-08 Bayer Aktiengesellschaft 5-perfluoroacylamino-4-nitro-1-arylpyrazole salts, plant growth regulating and herbicidal composition containing them, and plant growth regulating and herbicidal method of using them
CN1036397C (zh) * 1992-10-12 1997-11-12 先灵公司 新的取代的吡唑衍生物
CN107108621A (zh) * 2015-01-23 2017-08-29 协友株式会社 经取代的吡唑基吡唑衍生物及其作为除草剂的应用
WO2016121900A1 (fr) * 2015-01-30 2016-08-04 協友アグリ株式会社 Composition herbicide
WO2016121898A1 (fr) * 2015-01-30 2016-08-04 協友アグリ株式会社 Composition herbicide
JP2018016573A (ja) * 2016-07-27 2018-02-01 協友アグリ株式会社 除草剤組成物

Also Published As

Publication number Publication date
CN112341456B (zh) 2024-01-05
CN112341456A (zh) 2021-02-09

Similar Documents

Publication Publication Date Title
CN107629035B (zh) 一种吡唑酮类化合物或其盐、除草剂组合物及用途
WO2017075910A1 (fr) Composé de pyrazolone ou son sel, son procédé de préparation, composition herbicide et son utilisation
WO2017113509A1 (fr) Composé de pyrazole ou son sel, son procédé de préparation, composition herbicide et son utilisation
CN113105405B (zh) 一种羧酸衍生物取代的亚氨基芳基化合物及其制备方法、除草组合物和应用
TW201332968A (zh) 鄰苯二甲醯胺衍生物及含有該衍生物之農園藝用殺蟲劑以及其使用方法
WO2021143677A1 (fr) Composé aromatique substitué à cycle condensé, son procédé de préparation, composition herbicide et utilisation associée
WO2020108518A1 (fr) Formamides de n-(1,3,4-oxadiazole-2-yl)aryle ou leur sel, procédé de préparation correspondant, composition herbicide et utilisation associée
CN108586357B (zh) 取代的嘧啶甲酰基肟衍生物及其制备方法、除草组合物和应用
WO2019080226A1 (fr) Composé de benzonitrile dicétone substitué ou son tautomère, son sel, son procédé de préparation, herbicide ainsi obtenu et son application
WO2021088856A1 (fr) Composé aromatique contenant de l'isoxazoline substitué, procédé de préparation correspondant, composition herbicide et utilisation associée
KR102276572B1 (ko) 피라졸 화합물 또는 그의 염, 및 제조 방법, 제초제 조성물 및 그의 용도
WO2021078174A1 (fr) Composé de formamide aryl contenant de l'oxyde de soufre chiral et sel de celui-ci, son procédé de préparation, composition herbicide et utilisation
WO2019196731A1 (fr) Composé de pyrazolyl pyrazole de sulfonylurée substitué ou sel ou composition pesticide acceptable de celui-ci et utilisation associée
WO2021139498A1 (fr) Composé carboxylate d'isoxazoline oxime, son procédé de préparation et composition herbicide et utilisation associées
WO2019080227A1 (fr) Composé d'isoxazole benzoyle substitué ou tautomère et sel de celui-ci, procédé de préparation, composition herbicide et application
WO2019090818A1 (fr) Composé de 4-benzoylpyrazole, procédé de préparation s'y rapportant et utilisation de ce dernier
WO2021023292A1 (fr) Composé de pyrazolyl pyrazole substitué ou sel ou composition pesticide acceptable de celui-ci et utilisation associée
CN109400526B (zh) 吡啶氧基硫酯衍生物及其制备方法、除草组合物和应用
WO2020253696A1 (fr) Dérivé de pyridinecarboxylate de pyridineméthylène substitué, procédé de préparation correspondant, composition herbicide et utilisation associée
WO2020135236A1 (fr) Dérivé d'oxime d'acide pyridyl-oxycarboxylique et procédé de préparation correspondant, composition de désherbage et utilisation associée
WO2020156106A1 (fr) Formamides d'aryle hétérocycliques ou sel de ceux-ci, procédé de préparation, composition de désherbage et utilisation
WO2019033590A1 (fr) Composé benzoyle cyclohexanedione substitué ou tautomère et sel de celui-ci, son procédé de préparation, composition herbicide et utilisation
CN110551122B (zh) 一种取代的吡唑基吡唑磺酰胺类化合物或其作为农药可接受的盐、组合物及其用途
CN112625035B (zh) 一种5-氯苯并噁唑衍生物或其作为农药可接受的盐、组合物及其用途
CN112441993B (zh) 一种取代的噻二嗪酮二氧化物及其制备方法、除草组合物和应用

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: 20850195

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: 20850195

Country of ref document: EP

Kind code of ref document: A1