WO2016095768A1 - 一种含异恶唑啉的脲嘧啶类化合物及其用途 - Google Patents
一种含异恶唑啉的脲嘧啶类化合物及其用途 Download PDFInfo
- Publication number
- WO2016095768A1 WO2016095768A1 PCT/CN2015/097223 CN2015097223W WO2016095768A1 WO 2016095768 A1 WO2016095768 A1 WO 2016095768A1 CN 2015097223 W CN2015097223 W CN 2015097223W WO 2016095768 A1 WO2016095768 A1 WO 2016095768A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- alkyl
- group
- hydrogen
- haloalkyl
- phenyl
- Prior art date
Links
- 0 C*c(cc1)cc(Cl)c1Oc1cc(C(C)=O)c(*)cc1 Chemical compound C*c(cc1)cc(Cl)c1Oc1cc(C(C)=O)c(*)cc1 0.000 description 2
- RZVWBASHHLFBJF-UHFFFAOYSA-N COC(C1CCNCC1)=O Chemical compound COC(C1CCNCC1)=O RZVWBASHHLFBJF-UHFFFAOYSA-N 0.000 description 2
Classifications
-
- 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
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—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
- A01N43/80—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 five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
-
- 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 herbicides, and particularly relates to a uracil compound containing isoxazoline and a use thereof.
- Q 1 is a five-membered heterocyclic ring such as thiazole, oxazole, benzothiazole or benzoxazole.
- Q 2 is F or H.
- the present invention provides a uracil-containing uracil compound and use thereof.
- the present invention provides a uracil-containing uracil compound, as shown in the general formula (I):
- R 1 and R 2 are each independently selected from a C 1 -C 6 alkyl group or a C 1 -C 6 haloalkyl group;
- R 3 , R 4 , R 5 and R 6 are each independently selected from the group consisting of hydrogen, halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkane Thio or C 1 -C 6 alkylsulfonyl;
- R 7 and R 8 are each independently selected from the group consisting of hydrogen, cyano, C 1 -C 6 alkyl, CO 2 R 11 , CH 2 OR 12 , phenyl or phenyl substituted by 1 to 4 groups independently selected from the group consisting of: Halogen, CN, NO 2 , C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 1 -C 8 alkoxy, C 1 -C 8 haloalkoxy, C 1 -C 8 alkoxycarbonyl a C 1 -C 8 alkylthio group or a C 1 -C 8 alkylsulfonyl group;
- R 9 and R 10 are each independently selected from the group consisting of hydrogen, cyano, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, CO 2 R 11 , CH 2 OR 12 , CH 2 NR 13 R 14 , CONR 13 R 14 , phenyl or phenyl substituted by 1 to 4 independently selected from the group consisting of halogen, CN, NO 2 , C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy a C 1 -C 4 haloalkoxy group, a C 1 -C 4 alkoxycarbonyl group, a C 1 -C 4 alkylthio group, a C 1 -C 4 alkylsulfonyl group;
- R 11 is selected from the group consisting of hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C 1 -C 6 alkoxy C 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyloxy C 2 -C 4 alkyl, unsubstituted or substituted by 1 to 4 benzyl, furylmethyl, thiazolylmethyl, tetrahydrofuran Or pyridylmethyl: halogen, CN, NO 2 , C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 1 -C 8 alkoxy, C 1 -C 8 haloalkoxy, C 1 - C 8 alkoxycarbonyl, C 1 -C 8 alkylthio, C 1 -C 8 alkylsulfonyl;
- R 12 is selected from the group consisting of hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, C 3 -C 6 cycloalkylcarbonyl, C 3 -C 6 halocycloalkylcarbonyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylsulfonyl, C 1 -C 6 alkylamino Sulfonyl, di(C 1 -C 6 )alkylaminosulfonyl, C 1 -C 6 alkylaminocarbonyl, di(C 1 -C 6 )alkylaminocarbonyl, di(C 1 -C 6 )alkylaminocarbonyl, di(C 1 -C 6 )alkylaminocarbon
- R 3 , R 4 , R 5 , and R 6 are each independently selected from the group consisting of hydrogen, halogen, C 1 -C 6 alkyl or C 1 -C 6 alkoxy;
- R 10 is selected from hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, phenyl or phenyl substituted by 1 to 4 independently selected from the group consisting of halogen, CN, NO 2 , C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 alkylthio Or a C 1 -C 4 alkylsulfonyl group;
- R 12 is selected from the group consisting of hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, C 3 -C 6 cycloalkylcarbonyl, C 3 -C 6 halocycloalkylcarbonyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylsulfonyl, C 1 -C 6 alkylamino Sulfonyl, di(C 1 -C 6 )alkylaminosulfonyl, C 1 -C 6 alkylaminocarbonyl, di(C 1 -C 6 )alkylaminocarbonyl, di(C 1 -C 6 )alkylaminocarbonyl, di(C 1 -C 6 )alkylaminocarbon
- R 3 , R 4 , R 5 , and R 6 are each selected from hydrogen, halogen or C 1 -C 4 alkyl;
- R 9 is selected from the group consisting of hydrogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, CO 2 R 11 , CH 2 OR 12 , CH 2 NR 13 R 14 or CONR 13 R 14 ;
- R 10 is selected from hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, phenyl or phenyl substituted by 1 to 4 groups independently selected from halogen: CN, NO 2 , C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 alkylthio Or a C 1 -C 4 alkylsulfonyl group;
- R 2 is selected from CH 3 ;
- R 3 and R 4 are each selected from the group consisting of hydrogen, fluorine or chlorine;
- R 9 is selected from the group consisting of hydrogen, cyano, methyl, ethyl, CH 2 Cl, CH 2 Br, CO 2 R 11 , CH 2 OR 12 or CONR 13 R 14 ;
- R 10 is selected from the group consisting of hydrogen, methyl or ethyl
- Halogen refers to fluorine, chlorine, bromine or iodine.
- Alkyl a linear or branched alkyl group such as methyl, ethyl, propyl, isopropyl, n-butyl or t-butyl.
- Cycloalkyl a substituted or unsubstituted cyclic alkyl group such as cyclopropyl, cyclopentyl or cyclohexyl. Substituents such as methyl, halogen and the like.
- Alkenyl straight or branched olefins such as ethenyl, 1-propenyl, 2-propenyl and the different butenyl, pentenyl and hexenyl isomers. Alkenyl groups also include polyenes such as 1,2-propadienyl and 2,4-hexadienyl.
- Cycloalkylcarbonyl A cycloalkyl group is bonded to a structure via a carbonyl group such as a cyclopropionyl group or a cyclohexyl group.
- Halocycloalkylcarbonyl a halocycloalkyl group is attached to the structure via a carbonyl group, such as 1-chlorocyclopropanoyl or the like.
- Alkylaminosulfonyl alkyl-NH-SO 2 - such as CH 3 NHSO 2 - or C 2 H 5 NHSO 2 - and the like.
- Dialkylaminosulfonyl dialkyl-N-SO 2 - such as (CH 3 ) 2 NSO 2 - or (C 2 H 5 ) 2 NSO 2 - and the like.
- Alkylaminocarbonyl alkyl-NH-CO-, such as CH 3 NHCO- or C 2 H 5 NHCO-.
- Dialkylaminocarbonyl dialkyl-N-CO-, such as (CH 3 ) 2 NCO- or (C 2 H 5 ) 2 NCO- and the like.
- Dialkylaminothiocarbonyl Dialkyl-N-CS-, such as (CH 3 ) 2 NCS- or (C 2 H 5 ) 2 NCS- and the like.
- R 8 or R 9 is selected from CO 2 C 2 H 5 (I-1, I-1 ')
- the carboxylic acid (I-2, I-2') can be produced as described in the literature and then further formed into an ester compound ( I-3, I-3') and amide compounds (I-4, I-4'), such as US20060223848, WO2012130798, WO2014048827, WO2014048940 and the like.
- R 8 or R 9 is selected from CH 2 OCOCH 3 (I-5, I-5')
- the alcohol compound (I-6, I-6') can be obtained by reacting with acetyl chloride in methanol as described in the literature. Literature such as Synlett, 2005, 10: 1527–1530. It is then reacted with an acid halide represented by the formula R 12 -X, a benzyl halide or an aromatic or heteroaryl ring having an active halogen under basic conditions to give I-7 or I-7'.
- the base may be selected from alkali metal hydrides such as sodium hydride, lithium hydride or sodium amide; alkali metal hydroxides such as sodium hydroxide or potassium hydroxide; alkali metal carbonates such as sodium carbonate or potassium carbonate.
- An organic base such as pyridine, 4-dimethylaminopyridine, triethylamine, N-methylpyrrole or diisopropylethylamine.
- the reaction temperature may be between -10 ° C and a suitable solvent boiling temperature selected for use in the reaction, usually from 0 to 100 ° C.
- the reaction time is from 30 minutes to 20 hours, usually from 1 to 10 hours.
- R 12 -X are commercially available.
- X is a leaving group and X is selected from chlorine, bromine or iodine.
- the amino compound III can be obtained by using a nitro compound IV according to a conventional method using a reducing agent such as iron, zinc, palladium carbon or stannous chloride.
- a reducing agent such as iron, zinc, palladium carbon or stannous chloride.
- the nitro compound IV can be synthesized from the aldehyde VIII in three steps as described in the prior literature, such as J. Agric. Food Chem. 2005, 53, 8639-8643 or WO2006090234.
- the present invention also provides a herbicidal composition having the compound of the formula (I) as an active ingredient, and the active ingredient in the composition is present in an amount of from 0.1 to 99% by weight.
- the invention therefore also encompasses the use of the composition for controlling weeds.
- compositions may be used in the form of dry powders, wettable powders, emulsifiable concentrates, microemulsions, pastes, granules, solutions, suspensions and the like.
- 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.), paraffins (petroleum fractions), alcohols (methanol, propanol, butanol, octanol). , glycerol), esters (ethyl acetate, isobutyl acetate, etc.), ketones (cyclohexanone, acetone, acetophenone, isophorone, ethyl amyl ketone, etc.), amides (N, N) - dimethylformamide, N-methylpyrrolidone, etc.).
- Usable surfactants are sodium, calcium, triethylamines such as alkyl sulfonates, alkyl aryl sulfonates, polyoxyethylene alkyl phenols, polyoxyethylene esters of sorbitol, lignosulfonates, and the like. Or triethanolamine salt.
- 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.
- active ingredients compatible with the compounds of formula (I) 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 formulation 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 effect of the compound in water.
- Preparation of water-dispersible granules mixing and pulverizing the original drug with powdered solid diluent, wetting spreader and binder, adding water and kneading, and then adding it to a granulator equipped with a screen of a certain size. Granulation, then drying and sieving (by screen area).
- the original drug, the dispersing agent, the disintegrating agent and the wetting agent and the solid diluent may also be added to a sand mill, ground with water as a medium, and then spray-dried and granulated, usually in a content of 20- 30% granular product.
- the compounds of the formula (I) according to the invention are also suitable for the drying and/or defoliation of plants.
- the synthesis of the compounds 286 and 290 can be carried out in accordance with the preparation method of the compound 10 in Example 4.
- Example 14 35% emulsifiable concentrate
- the phosphorous acid is dissolved in cyclohexanone, and compound 6 and ethoxylated triglyceride are added to obtain a transparent solution.
- Example 15 60% wettable powder
- Compound 43 sodium dodecylnaphthalene sulfonate, sodium lignosulfonate and kaolin (both solids) were mixed together and pulverized in a pulverizer until the granules reached the standard.
- Compound 6 and other components are mixed and pulverized, and then kneaded with water, and then granulated by adding a 10-100 mesh sieve granulator, followed by drying and sieving (by sieve range).
- the compound 55 and the other components are thoroughly mixed, and the suspension thus obtained is diluted with water to obtain a diluent of any desired concentration.
- the herbicidal activity test method of the compound of the present invention is as follows:
- Quantitative weeds grass, golden foxtail
- broadleaf weeds Zinnia, ramie seeds were sown in a 7 cm diameter paper cup filled with nutrient soil, soiled 1 cm after sowing, repressed, After watering, it is cultured in a greenhouse in a conventional manner. Gramineous weeds grow to 2 to 3 leaf stage, broadleaf weeds 2 to 4 leaf stage stem and leaf spray treatment; pre-emergence soil spray treatment is carried out 24 hours after sowing.
- Spray treatment was carried out on a track-type crop sprayer (designed and manufactured by Engineering Research Ltd., UK) at a test design dose (spray pressure 1.95 kg/cm 2 , spray volume 500 L/hm 2 , crawler speed 1.48 km/h). The test was repeated 3 times. After the sample is processed, it is placed in the operation hall. After the liquid is naturally dried, it is placed in the greenhouse and managed according to the conventional method. The reaction of the weeds to the agent is observed and recorded. After the treatment, the test agent is regularly observed to control the weeds.
- Control effect grading standard 0 is invalid, 100% is to completely kill or severely suppress weeds.
- Saflufenacil The trade name is Barton Gold, which is commercially available. "-" means not tested.
- Quantitative crops (soybean, cotton, corn, wheat, rice) seeds were separately sown in a 9 cm diameter paper cup filled with nutrient soil. After sowing, the soil was covered with 1 cm. After suppression and watering, it was cultured in a greenhouse according to a conventional method. The 3rd leaf stage of the gramineous crops and the 2 ⁇ 4 leaf stage of the broad-leaved crops (1 ⁇ 2 three-leaf compound leaves) were sprayed with stems and leaves, and the pre-emergence soil spray treatment was carried out 24 hours after sowing.
- Spray treatment was carried out on a track-type crop sprayer (designed and manufactured by Engineering Research Ltd., UK) at a test design dose (spray pressure 1.95 kg/cm 2 , spray volume 500 L/ha, crawler speed 1.48 km/h). The test was repeated 3 times. After the test materials are processed, they are placed in the operation hall. After the liquid medicine is naturally dried, it is placed in the greenhouse and managed according to the conventional method. The reaction of the test crops to the chemicals is observed and recorded. After the treatment, the safety of the test drugs on the crops is regularly investigated. . Safety grading standards: 0 means no damage to the crop, 100 is to completely kill or severely inhibit the crop.
- the measurement method was the same as in Example 18.
- the test method is as follows: The test was carried out in the orchard of Fangjiazi Village, Liaoyang City, Liaoning province.
- the fruit trees are mainly apple trees, followed by apricot, plum, and pear trees.
- the weeding is carried out about three times a year, and the main agent is paraquat.
- the test was carried out on July 3, 2015.
- the treatment period is about the second treatment of the orchard.
- the weeds are dominated by broadleaf weeds, mainly including small canopies, chicory, sorghum, and alfalfa.
- grass weeds are mainly crabgrass, weeds are evenly distributed, moderate density, the average height of weeds is about 30-40cm when treated, and the sprayer is Singapore. Knapsack manual sprayer with a spray volume of 45kg/mu. The effects of broadleaf weeds, grass weeds and total weed control were investigated visually 15 days after treatment.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (12)
- 一种含异恶唑啉的脲嘧啶类化合物,其特征在于:化合物结构如通式(I)所示:式中:R1、R2分别选自C1-C6烷基或C1-C6卤代烷基;R3、R4、R5、R6分别选自氢、卤素、C1-C6烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C6烷硫基或C1-C6烷基磺酰基;R7、R8分别选自氢、氰基、C1-C6烷基、CO2R11、CH2OR12、苯基或被1-4个独立选自以下基团取代的苯基:卤素、CN、NO2、C1-C8烷基、C1-C8卤代烷基、C1-C8烷氧基、C1-C8卤代烷氧基、C1-C8烷氧基羰基、C1-C8烷硫基或C1-C8烷基磺酰基;R9、R10分别选自氢、氰基、C1-C6烷基、C1-C6卤代烷基、CO2R11、CH2OR12、CH2NR13R14、CONR13R14、苯基或被1-4个独立选自以下基团取代的苯基:卤素、CN、NO2、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷氧基羰基、C1-C4烷硫基、C1-C4烷基磺酰基;R11选自氢、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6炔基、C1-C6烷氧基C1-C6烷基、C1-C6烷羰基氧基C2-C4烷基,未取代或者被1-4个独立选自以下基团取代的苄基、呋喃甲基、噻唑甲基、四氢呋喃甲基或吡啶甲基:卤素、CN、NO2、C1-C8烷基、C1-C8卤代烷基、C1-C8烷氧基、C1-C8卤代烷氧基、C1-C8烷氧基羰基、C1-C8烷硫基、C1-C8烷基磺酰基;R12选自氢、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基羰基、C1-C6烷基羰基、C1-C6卤代烷基羰基、C3-C6环烷基羰基、C3-C6卤代环烷基羰基、C1-C6烷基磺酰基、C1-C6卤代烷基磺酰基、C1-C6烷基氨基磺酰基、二(C1-C6)烷基氨基磺酰基、C1-C6烷基氨基羰基、二(C1-C6)烷基氨基羰基、二(C1-C6)烷基氨基硫代羰基、C1-C6烷硫基C2-C6烷基羰基,未取代或者被1-4个独立选自以下基团取代的苯基、苯基C1-C2烷基、苯基C2-C4烯基、苯基羰基、苯基C1-C2烷基羰基、苯氧基C1-C2烷基羰基、苯基C2-C4烯基羰基、杂芳基、杂芳基C1-C2烷基、杂芳基羰基:卤素、CN、NO2、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷氧基羰基、C1-C4烷硫基、C1-C4烷基磺酰基或被1-4个卤素、CN、NO2、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基独立取代的苯氧基;R13、R14分别选自氢、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基羰基C1-C6烷基;或者,R13、R14可以通过N相连形成五元或六元环。
- 按照权利要求1所述的化合物,其特征在于:通式(I)中R1选自C1-C4卤代烷基;R2选自C1-C4烷基或C1-C4卤代烷基;R3、R4、R5、R6分别选自氢、卤素、C1-C6烷基或C1-C6烷氧基;R7选自氢或C1-C6烷基;R8选自氢、C1-C6烷基、CO2R11或CH2OR12;R9选自氢、氰基、C1-C6烷基、C1-C6卤代烷基、CO2R11、CH2OR12、CH2NR13R14或 CONR13R14;R10选自氢、C1-C6烷基、C1-C6卤代烷基、苯基或被1-4个独立选自以下基团取代的苯基:卤素、CN、NO2、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷氧基羰基、C1-C4烷硫基或C1-C4烷基磺酰基;R11选自氢、C1-C6烷基、C1-C6卤代烷基、C3-C4烯基、C3-C4炔基、C1-C4烷氧基C1-C4烷基、C1-C4烷羰基氧基C2-C3烷基,未取代或者被1-4个独立选自以下基团取代的苄基、呋喃甲基或四氢呋喃甲基:卤素、CN、NO2、C1-C6烷基或C1-C6卤代烷基;R12选自氢、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基羰基、C1-C6烷基羰基、C1-C6卤代烷基羰基、C3-C6环烷基羰基、C3-C6卤代环烷基羰基、C1-C6烷基磺酰基、C1-C6卤代烷基磺酰基、C1-C6烷基氨基磺酰基、二(C1-C6)烷基氨基磺酰基、C1-C6烷基氨基羰基、二(C1-C6)烷基氨基羰基、二(C1-C6)烷基氨基硫代羰基、C1-C6烷硫基C2-C6烷基羰基,未取代或者被1-4个独立选自以下基团取代的苯基C1-C2烷基、苯基羰基、苯基C1-C2烷基羰基、苯基C2-C4烯基羰基、苯氧基C1-C2烷基羰基、噻吩羰基、吡唑羰基、喹啉羰基:卤素、CN、NO2、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷氧基羰基、C1-C4烷硫基、C1-C4烷基磺酰基或被1-4个卤素、CN、NO2、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基独立取代的苯氧基;R13、R14分别选自氢、C1-C4烷基、C1-C4卤代烷基或C1-C4烷氧基羰基C1-C4烷基;或者,R13、R14可以通过N相连形成五元或六元环。
- 按照权利要求2所述的化合物,其特征在于:通式(I)中R1选自CF3;R2选自CH3;R3、R4、R5、R6分别选自氢、卤素或C1-C4烷基;R7选自氢或C1-C4烷基;R8选自氢、C1-C4烷基、CO2R11或CH2OR12;R9选自氢、氰基、C1-C4烷基、C1-C4卤代烷基、CO2R11、CH2OR12、CH2NR13R14或CONR13R14;R10选自氢、C1-C4烷基、C1-C4卤代烷基、苯基或被1-4个独立选自以下基团取代的苯基:卤素、CN、NO2、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷氧基羰基、C1-C4烷硫基或C1-C4烷基磺酰基;R11选自氢、C1-C4烷基、C1-C4卤代烷基、C3-C4烯基、C3-C4炔基、C1-C4烷氧基C1-C4烷基、C1-C4烷羰基氧基C2-C3烷基,未取代或者被1-4个独立选自以下基团取代的苄基、呋喃甲基或四氢呋喃甲基:卤素、CN、NO2、C1-C4烷基或C1-C4卤代烷基;R12选自氢、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基羰基、C1-C4烷基羰基、C1-C4卤代烷基羰基、C3-C6环烷基羰基、C3-C6卤代环烷基羰基、C1-C4烷基磺酰基、C1-C4卤代烷基磺酰基、C1-C3烷基氨基磺酰基、二(C1-C3)烷基氨基磺酰基、C1-C3烷基氨基羰基、二(C1-C3)烷基氨基羰基、二(C1-C3)烷基氨基硫代羰基、C1-C2烷硫基C2-C4烷基羰基,未取代或者被1-4个独立选自以下基团取代的苯基C1-C2烷基、苯基羰基、苯基C1-C2烷基羰基、苯基C2-C4烯基羰基、苯氧基C1-C2烷基羰基、噻吩羰基、吡唑羰基、喹啉羰基:卤素、CN、NO2、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷氧基羰基、C1-C4烷硫基、C1-C4烷基磺酰基或被1-4个卤素、CN、NO2、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基独立取代的苯氧基;R13、R14分别选自氢、C1-C4烷基、C1-C4卤代烷基或C1-C4烷氧基羰基C1-C4烷基;或者,R13、R14可以通过N相连形成五元或六元环。
- 按照权利要求3所述的化合物,其特征在于:通式(I)中R1选自CF3;R2选自CH3;R3、R4、R5、R6分别选自氢、氟、氯或甲基;R7选自氢或甲基;R8选自氢、甲基、CO2R11基或CH2OR12;R9选自氢、氰基、甲基、乙基、CH2Cl、CH2Br、CO2R11、CH2OR12、CH2NR13R14或CONR13R14;R10选自氢、C1-C4烷基、C1-C4卤代烷基、苯基或被1-4个独立选自以下基团取代的苯基:卤素、CN、NO2、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基;R11选自氢、C1-C4烷基、C1-C4卤代烷基、烯丙基、炔丙基、C1-C3烷氧基C1-C3烷基、C1-C4烷羰基氧基C2-C3烷基,未取代或者被1-4个独立选自以下基团取代的苄基、呋喃甲基或四氢呋喃甲基:卤素、CN、NO2或C1-C4烷基;R12选自氢、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基羰基、C1-C4烷基羰基、C1-C4卤代烷基羰基、C3-C6环烷基羰基、C1-C4烷基磺酰基、C1-C4卤代烷基磺酰基、二(C1-C3)烷基氨基磺酰基、C1-C3烷基氨基羰基、二(C1-C3)烷基氨基羰基、二(C1-C3)烷基氨基硫代羰基、C1-C2烷硫基C2-C4烷基羰基,未取代或者被1-4个独立选自以下基团的苯基羰基、苯基C1-C2烷基羰基、苯氧基C1-C2烷基羰基、噻吩羰基、喹啉羰基或吡唑羰基:卤素、CN、NO2、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷氧基羰基、C1-C4烷硫基、C1-C4烷基磺酰基或2-氯-4-三氟甲基苯氧基;R13、R14分别选自氢、C1-C4烷基、C1-C4卤代烷基或C1-C4烷氧基羰基C1-C4烷基;或者,R13、R14可以通过N相连形成五元或六元环。
- 按照权利要求4所述的化合物,其特征在于:通式(I)中R1选自CF3;R2选自CH3;R3、R4分别选自氢、氟、氯或甲基;R5、R6分别选自氢;R7选自氢或甲基;R8分别选自氢、甲基、CO2R11或CH2OR12;R9选自氢、氰基、甲基、乙基、CH2Cl、CH2Br、CO2R11、CH2OR12或CONR13R14;R8、R9不同时为CO2R11或CH2OR12;R10选自氢、甲基、乙基、三氟甲基、二氟甲基、苯基或被1-4个独立选自以下基团取代的苯基:卤素、CN、NO2、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基;R11选自氢、甲基、乙基、正丙基、正丁基、异丙基、异丁基、叔丁基、三氟乙基、烯丙基、炔丙基、甲氧基乙基、乙氧基乙基、甲基羰基氧基乙基或四氢呋喃甲基;R12选自氢、C1-C4烷氧基羰基、C1-C4烷基羰基、C1-C4卤代烷基羰基、C3-C6环烷基羰基、C1-C4烷基磺酰基、C1-C4卤代烷基磺酰基、二(C1-C2)烷基氨基磺酰基、C1-C2烷基氨基羰基、二(C1-C3)烷基氨基羰基、二(C1-C2)烷基氨基硫代羰基、C1-C2烷硫基C2-C4烷基羰基,未取代或者被1-4个独立选自以下基团的苯基羰基、苯基C1-C2烷基羰基、苯氧基C1-C2烷基羰基、喹啉羰基或噻吩羰基:卤素、CN、NO2、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷氧基羰基、C1-C4烷硫基、C1-C4烷基磺酰基或2-氯-4-三氟甲基苯氧基;R13选自氢、C1-C4烷基或C1-C4卤代烷基;R14选自氢、C1-C4烷基或C1-C4烷氧基羰基C1-C4烷基;或者,R13、R14可以通过N相连形成五元或六元环。
- 按照权利要求5所述的化合物,其特征在于:通式(I)中R1选自CF3;R2选自CH3;R3、R4分别选自氢、氟或氯;R5、R6分别选自氢;R7选自氢或甲基;R8选自氢、甲基、CO2R11或CH2OR12;R9选自氢、氰基、甲基、乙基、CH2Cl、CH2Br、CO2R11、CH2OR12或CONR13R14;R8、R9不同时为CO2R11或CH2OR12;R10选自氢、甲基或乙基;R11选自氢、甲基、乙基、正丙基、正丁基、异丙基、异丁基、叔丁基、三氟乙基、烯丙基、炔丙基、甲氧基乙基、乙氧基乙基、甲基羰基氧基乙基或四氢呋喃甲基;R12选自氢、C1-C4烷基羰基、C1-C4卤代烷基羰基、C3-C6环烷基羰基、C1-C4烷基磺酰基、C1-C4卤代烷基磺酰基、二(C1-C2)烷基氨基磺酰基、二(C1-C3)烷基氨基羰基、二(C1-C2)烷基氨基硫代羰基、C1-C2烷硫基C2-C4烷基羰基、苯基C1-C2烷基羰基、2-甲基-4-氯苯氧乙酰基、2,4-二氯苯氧乙酰基、噻吩羰基或选自如下结构:R13选自氢、C1-C4烷基或C1-C4卤代烷基;R14选自氢、C1-C4烷基或C1-C4烷氧基羰基C1-C4烷基;
- 按照权利要求6所述的化合物,其特征在于:通式(I)中R1选自CF3;R2选自CH3;R3、R4分别选自氢、氟或氯;R5、R6、R7、R8分别选自氢;R9选自氢、氰基、甲基、乙基、CH2Cl、CH2Br、CO2R11、CH2OR12或CONR13R14;R10选自氢、甲基或乙基;R11选自氢、甲基、乙基、正丙基、正丁基、异丙基、异丁基、叔丁基、三氟乙基、烯丙基、炔丙基、甲氧基乙基、乙氧基乙基、甲基羰基氧基乙基或四氢呋喃甲基;R12选自氢、C1-C4烷基羰基、C1-C4卤代烷基羰基、环丙甲酰基、C1-C4烷基磺酰基、C1-C4卤代烷基磺酰基、二(C1-C2)烷基氨基磺酰基、二(C1-C3)烷基氨基羰基、二(C1-C2)烷基氨基硫代羰基、C1-C2烷硫基C2-C4烷基羰基、苯基C1-C2烷基羰基、2-甲基-4-氯苯氧乙酰基、2,4-二氯苯氧乙酰基、噻吩羰基或选自如下结构:R13选自氢、甲基、乙基、异丙基、正丙基、正丁基、叔丁基、三氟乙基、二氟乙基、1- 氯乙基、1-氯丙基或2-氯丙基;R14选自氢、甲基、乙基、异丙基、正丙基、正丁基、叔丁基或C1-C4烷氧基羰基C1-C4烷基;
- 一种根据权利要求1所述的通式(I)化合物用于防治杂草的应用。
- 一种除草组合物,其特征在于:以权利要求1所述的通式(I)化合物作为活性组分,组合物中的活性组分的重量百分含量为0.1-99%。
- 一种根据权利要求11所述的除草组合物用于防治杂草的应用。
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US15/527,864 US10550111B2 (en) | 2014-12-16 | 2015-12-14 | Pyrimidine urea compound containing isoxazolines and use thereof |
AU2015366689A AU2015366689B2 (en) | 2014-12-16 | 2015-12-14 | Uracil compounds containing isoxazoline ring and the uses thereof |
BR112017005410-8A BR112017005410B1 (pt) | 2014-12-16 | 2015-12-14 | Compostos de uracila contendo anel de isoxazolina e os usos dos mesmos |
CN201580034859.7A CN106536517B (zh) | 2014-12-16 | 2015-12-14 | 一种含异恶唑啉的脲嘧啶类化合物及其用途 |
CA2958170A CA2958170C (en) | 2014-12-16 | 2015-12-14 | Pyrimidine urea compound containing isoxazolines and use thereof |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201410781642.X | 2014-12-16 | ||
CN201410781642.XA CN105753853B (zh) | 2014-12-16 | 2014-12-16 | 一种含异恶唑啉的脲嘧啶类化合物及其用途 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2016095768A1 true WO2016095768A1 (zh) | 2016-06-23 |
Family
ID=56125922
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/CN2015/097223 WO2016095768A1 (zh) | 2014-12-16 | 2015-12-14 | 一种含异恶唑啉的脲嘧啶类化合物及其用途 |
Country Status (7)
Country | Link |
---|---|
US (1) | US10550111B2 (zh) |
CN (2) | CN105753853B (zh) |
AR (1) | AR103048A1 (zh) |
AU (1) | AU2015366689B2 (zh) |
BR (1) | BR112017005410B1 (zh) |
CA (1) | CA2958170C (zh) |
WO (1) | WO2016095768A1 (zh) |
Cited By (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108570041A (zh) * | 2017-03-14 | 2018-09-25 | 沈阳中化农药化工研发有限公司 | 一种含异恶唑啉脲嘧啶类化合物的制备方法 |
WO2020063613A1 (zh) | 2018-09-29 | 2020-04-02 | 沈阳中化农药化工研发有限公司 | 一种甲基化制备含异恶唑啉脲嘧啶类化合物的方法 |
WO2020119480A1 (zh) | 2018-12-14 | 2020-06-18 | 沈阳中化农药化工研发有限公司 | 一种除草剂组合物固体制剂及其制备方法 |
WO2020119415A1 (zh) | 2018-12-14 | 2020-06-18 | 沈阳中化农药化工研发有限公司 | 一种除草组合物及其应用 |
WO2020234422A1 (en) | 2019-05-22 | 2020-11-26 | Syngenta Crop Protection Ag | Herbicidal compositions |
WO2021073487A1 (zh) | 2019-10-18 | 2021-04-22 | 沈阳中化农药化工研发有限公司 | 一种具有旋光活性的异恶唑啉类化合物及用途 |
WO2021082901A1 (zh) * | 2019-10-29 | 2021-05-06 | 沈阳中化农药化工研发有限公司 | 一种苯基异恶唑啉类化合物及其用途 |
WO2022002116A1 (zh) | 2020-07-02 | 2022-01-06 | 沈阳中化农药化工研发有限公司 | 一种苯基异恶唑啉类化合物的制备方法 |
WO2022002117A1 (zh) | 2020-07-02 | 2022-01-06 | 沈阳中化农药化工研发有限公司 | 一种制备含异恶唑啉脲嘧啶类化合物中间体的方法 |
WO2022043205A1 (de) | 2020-08-24 | 2022-03-03 | Bayer Aktiengesellschaft | Substituierte n-phenyluracile sowie deren salze und ihre verwendung als herbizide wirkstoffe |
WO2022095908A1 (zh) * | 2020-11-04 | 2022-05-12 | 沈阳中化农药化工研发有限公司 | 一种除草剂组合物及其应用 |
WO2023222831A1 (en) | 2022-05-20 | 2023-11-23 | Syngenta Crop Protection Ag | Herbicidal compositions |
WO2023222768A1 (en) | 2022-05-20 | 2023-11-23 | Syngenta Crop Protection Ag | A method of controlling weeds |
WO2024013016A1 (en) | 2022-07-11 | 2024-01-18 | Bayer Aktiengesellschaft | Herbicidal compositions |
WO2024078906A1 (de) | 2022-10-10 | 2024-04-18 | Bayer Aktiengesellschaft | Substituierte n-phenyluracile sowie deren salze und ihre verwendung als herbizide wirkstoffe |
WO2024110366A1 (en) | 2022-11-24 | 2024-05-30 | Syngenta Crop Protection Ag | A method for controlling weeds |
Families Citing this family (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108207997B (zh) * | 2016-12-21 | 2020-07-21 | 沈阳中化农药化工研发有限公司 | 一种除草剂组合物及其应用 |
CN109864067B (zh) * | 2017-12-02 | 2021-04-13 | 沈阳中化农药化工研发有限公司 | 一种除草组合物及应用 |
CN109864068B (zh) * | 2017-12-02 | 2021-04-13 | 沈阳中化农药化工研发有限公司 | 一种除草组合物及其应用 |
CN110150302B (zh) * | 2018-02-12 | 2021-06-18 | 沈阳中化农药化工研发有限公司 | 一种除草剂组合物及其应用 |
CN110692643B (zh) * | 2018-07-09 | 2021-10-29 | 沈阳中化农药化工研发有限公司 | 一种除草剂及其应用 |
CN110818699B (zh) * | 2018-08-08 | 2022-08-02 | 沈阳中化农药化工研发有限公司 | 一种异恶唑啉类化合物及其用途 |
CN110818644B (zh) * | 2018-08-08 | 2022-08-23 | 沈阳中化农药化工研发有限公司 | 一种异恶唑啉羧酸酯类化合物和应用 |
CN109053693B (zh) | 2018-09-20 | 2021-02-05 | 顺毅股份有限公司 | 哒嗪胺类化合物的制备及其应用 |
CN114557358A (zh) * | 2018-10-20 | 2022-05-31 | 南通江山农药化工股份有限公司 | 含苯嘧草唑的除草剂组合物及其应用 |
CN111961041B (zh) * | 2019-05-20 | 2022-09-16 | 南开大学 | 硫代三嗪酮异恶唑啉类化合物及其制备方法和应用、原卟啉原氧化酶抑制剂和除草剂 |
JP2022534105A (ja) * | 2019-05-29 | 2022-07-27 | シンジェンタ クロップ プロテクション アクチェンゲゼルシャフト | 除草化合物 |
CN115462385A (zh) * | 2019-10-23 | 2022-12-13 | 沈阳中化农药化工研发有限公司 | 一种包含具有旋光活性的苯基异噁唑啉类的除草组合物及应用 |
CN112745305A (zh) * | 2019-10-29 | 2021-05-04 | 沈阳中化农药化工研发有限公司 | 一种三嗪酮类化合物及其用途 |
CN117567451A (zh) * | 2019-11-07 | 2024-02-20 | 青岛清原化合物有限公司 | 一种含取代异恶唑啉的芳香类化合物及其制备方法、除草组合物和应用 |
CN113149975B (zh) * | 2020-01-07 | 2023-09-01 | 青岛清原化合物有限公司 | 一种异噁唑啉甲酸肟酯类化合物及其制备方法、除草组合物和应用 |
CA3135347A1 (en) | 2020-01-16 | 2021-07-22 | Qingdao Kingagroot Chemical Compound Co., Ltd. | A fused-ring substituted aromatic compound, preparation method, herbicidal composition and use thereof |
KR20230112652A (ko) * | 2020-11-24 | 2023-07-27 | 신젠타 크롭 프로텍션 아게 | 제초 화합물 |
CA3215427A1 (en) | 2021-04-02 | 2022-10-06 | Qingdao Kingagroot Chemical Compound Co., Ltd. | Ppo polypeptides tolerant to ppo-inhibiting herbicides and use thereof |
CA3214498A1 (en) * | 2021-04-07 | 2022-10-13 | Syngenta Crop Protection Ag | Herbicidal compounds |
CN113455513A (zh) * | 2021-06-26 | 2021-10-01 | 南通江山农药化工股份有限公司 | 一种除草组合物、制剂及其应用 |
WO2023272463A1 (zh) * | 2021-06-29 | 2023-01-05 | 沈阳中化农药化工研发有限公司 | 一种除草剂组合物可分散油悬浮剂及其制备方法 |
CN116941626A (zh) * | 2022-04-15 | 2023-10-27 | 青岛清原作物科学有限公司 | 一种包含稠环取代的芳香类化合物的除草组合物及其应用 |
WO2024012968A1 (en) * | 2022-07-13 | 2024-01-18 | Syngenta Crop Protection Ag | Herbicidal pyrimidinone derivatives |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1061966A (zh) * | 1990-12-05 | 1992-06-17 | 日产化学工业株式会社 | 含有尿嘧啶衍生物的除草剂组合物及其制备方法 |
WO2004056785A2 (en) * | 2002-12-23 | 2004-07-08 | Isagro Ricerca S.R.L. | Uracils having a herbicidal activity |
WO2006090234A1 (en) * | 2005-02-22 | 2006-08-31 | Ranbaxy Laboratories Limited | Heterocyclic derivatives as cell adhesion inhibitors |
WO2008000438A1 (en) * | 2006-06-27 | 2008-01-03 | Syngenta Participations Ag | Insecticidal compounds |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5336663A (en) | 1991-11-13 | 1994-08-09 | Ciba-Geigy Corporation | 3-aryluracil derivatives and their use for weed control |
DE19852095A1 (de) * | 1998-11-12 | 2000-05-18 | Basf Ag | Verfahren zur Herstellung von 2-Alkyl-3-(4,5-dihydroisoxazol-3-yl)-acylbenzolen |
EA005677B1 (ru) | 2000-05-04 | 2005-04-28 | Басф Акциенгезельшафт | Гетероциклилзамещенные фенилсульфамоилкарбоксамиды |
DE10051981A1 (de) | 2000-10-20 | 2002-05-02 | Bayer Ag | Substituierte Phenyluracile |
KR100594544B1 (ko) | 2003-08-27 | 2006-06-30 | 주식회사 엘지생명과학 | 이소옥사졸린 구조를 갖는 캐스파제 저해제 |
US20070155738A1 (en) | 2005-05-20 | 2007-07-05 | Alantos Pharmaceuticals, Inc. | Heterobicyclic metalloprotease inhibitors |
PL2691379T3 (pl) | 2011-03-31 | 2017-05-31 | Bayer Intellectual Property Gmbh | Skuteczne chwastobójczo i grzybobójczo 3-fenyloizoksazolino-5-karboksamidy i 3-fenyloizoksazolino-5-tioamidy |
JP6472382B2 (ja) | 2012-09-25 | 2019-02-20 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | 除草効果を有する3−フェニルイソオキサゾリン誘導体 |
EP2900661B1 (en) | 2012-09-28 | 2016-10-26 | Bayer CropScience AG | Quinoline isoxazolin derivatives for plant disease control |
-
2014
- 2014-12-16 CN CN201410781642.XA patent/CN105753853B/zh active Active
-
2015
- 2015-12-14 AU AU2015366689A patent/AU2015366689B2/en active Active
- 2015-12-14 CN CN201580034859.7A patent/CN106536517B/zh active Active
- 2015-12-14 CA CA2958170A patent/CA2958170C/en active Active
- 2015-12-14 BR BR112017005410-8A patent/BR112017005410B1/pt active IP Right Grant
- 2015-12-14 WO PCT/CN2015/097223 patent/WO2016095768A1/zh active Application Filing
- 2015-12-14 US US15/527,864 patent/US10550111B2/en active Active
- 2015-12-15 AR ARP150104106A patent/AR103048A1/es unknown
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1061966A (zh) * | 1990-12-05 | 1992-06-17 | 日产化学工业株式会社 | 含有尿嘧啶衍生物的除草剂组合物及其制备方法 |
WO2004056785A2 (en) * | 2002-12-23 | 2004-07-08 | Isagro Ricerca S.R.L. | Uracils having a herbicidal activity |
WO2006090234A1 (en) * | 2005-02-22 | 2006-08-31 | Ranbaxy Laboratories Limited | Heterocyclic derivatives as cell adhesion inhibitors |
WO2008000438A1 (en) * | 2006-06-27 | 2008-01-03 | Syngenta Participations Ag | Insecticidal compounds |
Cited By (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108570041A (zh) * | 2017-03-14 | 2018-09-25 | 沈阳中化农药化工研发有限公司 | 一种含异恶唑啉脲嘧啶类化合物的制备方法 |
CN108570041B (zh) * | 2017-03-14 | 2024-02-09 | 沈阳中化农药化工研发有限公司 | 一种含异恶唑啉脲嘧啶类化合物的制备方法 |
WO2020063613A1 (zh) | 2018-09-29 | 2020-04-02 | 沈阳中化农药化工研发有限公司 | 一种甲基化制备含异恶唑啉脲嘧啶类化合物的方法 |
KR102510391B1 (ko) | 2018-09-29 | 2023-03-15 | 지앙수 양농 케미컬 그룹 컴퍼니 리미티드 | 메틸화를 통한 이속사 졸린 함유 우라실 화합물의 제조 방법 |
KR20210057107A (ko) | 2018-09-29 | 2021-05-20 | 센양 싸이노켐 어그로케미컬스 알앤디 코포레이션 리미티드 | 메틸화를 통한 이속사 졸린 함유 우라실 화합물의 제조 방법 |
WO2020119480A1 (zh) | 2018-12-14 | 2020-06-18 | 沈阳中化农药化工研发有限公司 | 一种除草剂组合物固体制剂及其制备方法 |
WO2020119415A1 (zh) | 2018-12-14 | 2020-06-18 | 沈阳中化农药化工研发有限公司 | 一种除草组合物及其应用 |
EP3900537A4 (en) * | 2018-12-14 | 2022-10-05 | Shenyang Sinochem Agrochemicals R & D Co., Ltd. | HERBICIDE COMPOSITION AND ADMINISTRATION THEREOF |
WO2020234422A1 (en) | 2019-05-22 | 2020-11-26 | Syngenta Crop Protection Ag | Herbicidal compositions |
WO2021073487A1 (zh) | 2019-10-18 | 2021-04-22 | 沈阳中化农药化工研发有限公司 | 一种具有旋光活性的异恶唑啉类化合物及用途 |
WO2021082901A1 (zh) * | 2019-10-29 | 2021-05-06 | 沈阳中化农药化工研发有限公司 | 一种苯基异恶唑啉类化合物及其用途 |
WO2022002117A1 (zh) | 2020-07-02 | 2022-01-06 | 沈阳中化农药化工研发有限公司 | 一种制备含异恶唑啉脲嘧啶类化合物中间体的方法 |
WO2022002116A1 (zh) | 2020-07-02 | 2022-01-06 | 沈阳中化农药化工研发有限公司 | 一种苯基异恶唑啉类化合物的制备方法 |
WO2022043205A1 (de) | 2020-08-24 | 2022-03-03 | Bayer Aktiengesellschaft | Substituierte n-phenyluracile sowie deren salze und ihre verwendung als herbizide wirkstoffe |
WO2022095908A1 (zh) * | 2020-11-04 | 2022-05-12 | 沈阳中化农药化工研发有限公司 | 一种除草剂组合物及其应用 |
WO2023222831A1 (en) | 2022-05-20 | 2023-11-23 | Syngenta Crop Protection Ag | Herbicidal compositions |
WO2023222768A1 (en) | 2022-05-20 | 2023-11-23 | Syngenta Crop Protection Ag | A method of controlling weeds |
WO2024013016A1 (en) | 2022-07-11 | 2024-01-18 | Bayer Aktiengesellschaft | Herbicidal compositions |
WO2024078906A1 (de) | 2022-10-10 | 2024-04-18 | Bayer Aktiengesellschaft | Substituierte n-phenyluracile sowie deren salze und ihre verwendung als herbizide wirkstoffe |
WO2024110366A1 (en) | 2022-11-24 | 2024-05-30 | Syngenta Crop Protection Ag | A method for controlling weeds |
Also Published As
Publication number | Publication date |
---|---|
AR103048A1 (es) | 2017-04-12 |
BR112017005410A2 (pt) | 2017-12-12 |
CA2958170A1 (en) | 2016-06-23 |
CN105753853A (zh) | 2016-07-13 |
AU2015366689A1 (en) | 2017-03-09 |
BR112017005410B1 (pt) | 2022-03-22 |
CN106536517A (zh) | 2017-03-22 |
AU2015366689A2 (en) | 2018-03-22 |
CN105753853B (zh) | 2020-08-04 |
CA2958170C (en) | 2020-07-14 |
US10550111B2 (en) | 2020-02-04 |
AU2015366689B2 (en) | 2018-11-08 |
US20180230139A1 (en) | 2018-08-16 |
CN106536517B (zh) | 2020-03-17 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
WO2016095768A1 (zh) | 一种含异恶唑啉的脲嘧啶类化合物及其用途 | |
JP5183735B2 (ja) | 置換ピリミジンエーテル化合物及びそれらの使用 | |
WO2010060379A1 (zh) | 具有含氮五元杂环的醚类化合物及其应用 | |
CN106316931B (zh) | 具有杀虫杀螨活性的2-苯基烟酸衍生物 | |
US8969332B2 (en) | Aryloxy dihalopropenyl ether compounds and uses thereof | |
WO2019165798A1 (zh) | 不饱和烃嘧啶硫醚类化合物及其制备方法与应用 | |
WO2009146648A1 (zh) | 酰胺类化合物及其制备与应用 | |
CN111362931A (zh) | 一种异噁唑啉连吡唑酰胺类化合物、其制备方法及应用 | |
CN110054596B (zh) | 一种取代噁二唑类化合物及其应用 | |
CN115701430A (zh) | 一种含异恶唑啉的苯基吡啶类化合物及其用途 | |
WO2021082901A1 (zh) | 一种苯基异恶唑啉类化合物及其用途 | |
CN105777733A (zh) | 一种含异恶唑啉的四氢邻苯二甲酰亚胺类化合物及其用途 | |
WO2021073487A1 (zh) | 一种具有旋光活性的异恶唑啉类化合物及用途 | |
CN113045561B (zh) | 用作杀真菌剂的二芳胺衍生物 | |
WO1998054154A1 (fr) | Composes de pyrimidine, leur procede de production et pesticides | |
JP6934817B2 (ja) | 除草化合物 | |
WO2008134970A1 (fr) | Composés anthranilamides et leur utilisation | |
CN110964037B (zh) | 含嘧啶并环类化合物及其制备方法和用途 | |
CN108976167B (zh) | 一种取代苯肼类化合物及其应用 | |
WO2012059048A1 (zh) | 吡唑酰胺类化合物及其用途 | |
CN115433177A (zh) | 一种芳基异恶唑啉类化合物及其用途 |
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: 15869275 Country of ref document: EP Kind code of ref document: A1 |
|
ENP | Entry into the national phase |
Ref document number: 2958170 Country of ref document: CA |
|
ENP | Entry into the national phase |
Ref document number: 2015366689 Country of ref document: AU Date of ref document: 20151214 Kind code of ref document: A |
|
REG | Reference to national code |
Ref country code: BR Ref legal event code: B01A Ref document number: 112017005410 Country of ref document: BR |
|
WWE | Wipo information: entry into national phase |
Ref document number: 15527864 Country of ref document: US |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
ENP | Entry into the national phase |
Ref document number: 112017005410 Country of ref document: BR Kind code of ref document: A2 Effective date: 20170316 |
|
122 | Ep: pct application non-entry in european phase |
Ref document number: 15869275 Country of ref document: EP Kind code of ref document: A1 |