WO2010034153A1 - Nouveaux composés esters d'acide 2-pyrimidinyloxy(sulfo)benzoxyoléfinique et leurs utilisations - Google Patents

Nouveaux composés esters d'acide 2-pyrimidinyloxy(sulfo)benzoxyoléfinique et leurs utilisations Download PDF

Info

Publication number
WO2010034153A1
WO2010034153A1 PCT/CN2008/072516 CN2008072516W WO2010034153A1 WO 2010034153 A1 WO2010034153 A1 WO 2010034153A1 CN 2008072516 W CN2008072516 W CN 2008072516W WO 2010034153 A1 WO2010034153 A1 WO 2010034153A1
Authority
WO
WIPO (PCT)
Prior art keywords
compound
formula
pyrimidinyloxy
hydrazine
alkyl
Prior art date
Application number
PCT/CN2008/072516
Other languages
English (en)
Chinese (zh)
Inventor
李斌
白丽萍
崔东亮
冀海英
张弘
刘广昕
于海波
Original Assignee
沈阳化工研究院
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 沈阳化工研究院 filed Critical 沈阳化工研究院
Priority to PCT/CN2008/072516 priority Critical patent/WO2010034153A1/fr
Publication of WO2010034153A1 publication Critical patent/WO2010034153A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/60—Three or more oxygen or sulfur atoms
    • 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
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines

Definitions

  • the present invention belongs to the field of herbicides, and specifically relates to 2-pyrimidinyloxy(thio)benzoyl enoate compounds and uses thereof.
  • R is a hydroxyl group, a lower alkoxy group or -0-(CH 2 ) nR 3 (wherein R 3 is a lower alkoxycarbonyl group or the like, n is an integer of 1 or 2) and the like.
  • 1 ⁇ is COOR4 (hydrogen, dC 6 alkyl group, a benzyl group, alkali metal atom, an alkaline earth metal atom or an organic ammonium) and the like.
  • R is an OR 3 group ⁇ R 3 is a hydrogen atom, d 4 alkyl (wherein the alkyl group may be substituted by the following group: R'COO- (R' is a d- 8 alkyl) or d- 8 alkoxycarbonyloxy Base, etc.), C 2 -8 alkenyl or halogenated C 2 -8 alkenyl, etc.
  • An object of the present invention is to provide a novel 2-pyrimidinyloxy(thio)benzoyl enoate compound and its use as a herbicide.
  • the present invention provides a novel 2-pyrimidinyloxy(thio)benzoyl enoate compound as shown in the general formula (I) or (II):
  • X is selected from oxygen or sulfur
  • R 2 is selected from CC 3 alkyl, C 3 -C 5 alkenyl or C 3 -C 5 alkynyl;
  • R 3 is selected from CC 3 alkyl, C 3 -C 6 alkenyl or C 3 -C 6 alkynyl.
  • a more preferred compound of the present invention is in the formula (I) or ( ⁇ )
  • X is selected from oxygen or sulfur
  • R 2 is selected from dC 3 alkyl
  • R 3 is selected from the group consisting of CC 3 alkyl.
  • More preferred compounds of the invention are those of formula (I) or (II)
  • X is selected from oxygen or sulfur; Selected from H, chloro, acetyl, 4,6-dimethoxypyrimidin-2-yl or the following groups:
  • the nitrogen bond and the methyl group on the double bond are cis or trans;
  • R 2 is selected from ethyl
  • R 3 is selected from a methyl group.
  • the alkyl group represented by the formula (I) or (II) includes a linear or branched alkyl group.
  • the alkenyl group means a group having 1 to 2 carbon-carbon double bonds in a straight-chain or branched form, such as a propenyl group, an allyl group and the like.
  • An alkynyl group means a group having 1 to 2 carbon-carbon triple bonds in a straight or branched form, such as propynyl, propargyl and the like.
  • Halogen includes fluorine, chlorine, bromine, and iodine.
  • the compound of the formula (I) of the present invention can be produced by a method wherein the X, Ri R 2 and R 3 groups are as defined above. method one:
  • Compound (V) and a suitable base are added to a mixed solvent of a suitable organic solvent and water at a temperature of
  • the reaction is carried out at -10 ° C to the boiling point for 0.5 to 48 hours, and the reaction solution is acidified with hydrochloric acid or sulfuric acid to obtain an intermediate acid, Compound (VI).
  • the organic solvent is selected from the group consisting of chloroform, dichloromethane, carbon tetrachloride, n-hexane, benzene, toluene, ethyl acetate, methanol, ethanol, tetrahydrofuran or dioxane;
  • the base is selected from the group consisting of sodium hydroxide, potassium hydroxide, and carbonic acid. Sodium or potassium carbonate, etc.
  • Compound (VI) and compound (VII) (for the preparation of VII, see Synthetic Chemistry, 13(3), 315-316, (2005)) are dissolved in a suitable solvent such as toluene, acetone, hydrazine, hydrazine-dimethyl methacrylate. Amide, tetrahydrofuran or dioxane; etc.
  • the alkali substance such as triethylamine, pyridine, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, etc., is favorable for the reaction, and the reaction is carried out at a temperature of -10 ° C to the boiling point for 0.5 to 48 hours to prepare a compound (1).
  • Y may be chlorine, bromine or iodine.
  • the compound (IV-1) and the compound (VII) are dissolved in a suitable solvent such as toluene, acetone, hydrazine, hydrazine-dimethylformamide, tetrahydrofuran or dioxane, etc.; and a base such as triethylamine is added.
  • a suitable solvent such as toluene, acetone, hydrazine, hydrazine-dimethylformamide, tetrahydrofuran or dioxane, etc.
  • a base such as triethylamine is added.
  • Pyridine, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate or the like is advantageous for the reaction, and the reaction is carried out at a temperature of from -10 ° C to the boiling point for 0.5 to 48 hours to obtain a compound (VIII).
  • Y may be chlorine, bromine or iodine.
  • the compound (VIII) and the compound (III) are dissolved in a suitable solvent such as toluene, acetone, hydrazine, hydrazine-dimethylformamide, tetrahydrofuran or dioxane; and a base such as triethylamine is added.
  • a suitable solvent such as toluene, acetone, hydrazine, hydrazine-dimethylformamide, tetrahydrofuran or dioxane
  • a base such as triethylamine
  • the compound of the formula (II) of the present invention can be produced by a method wherein the X, Ri R 2 and R 3 groups are as defined above. method one:
  • Compound (VI) and compound (IX) (for the preparation of IX, see CN1927811) are dissolved in a suitable solvent such as toluene, acetone, hydrazine, hydrazine-dimethylformamide, tetrahydrofuran or dioxane; Such as triethylamine, pyridine, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, etc., the reaction is favorable, the temperature is between -10 ° C and the boiling point Compound (11) is obtained in an amount of from 0.5 to 48 hours.
  • Z may be chlorine, bromine or iodine t method two:
  • the compound (IV-1) and the compound (IX) are dissolved in a suitable solvent such as toluene, acetone, hydrazine, hydrazine-dimethylformamide, tetrahydrofuran or dioxane; and a base such as triethylamine is added.
  • a suitable solvent such as toluene, acetone, hydrazine, hydrazine-dimethylformamide, tetrahydrofuran or dioxane
  • a base such as triethylamine is added.
  • Pyridine, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, etc. have a reaction for the reaction, and the reaction is carried out at a temperature of -10 ° C to the boiling point for 0.5 to 48 hours to obtain a compound ( ⁇ ).
  • hydrazine may be chlorine, bromine or iodine.
  • the compound (X) and the compound (III) are dissolved in a suitable solvent such as toluene, acetone, hydrazine, hydrazine-dimethylformamide, tetrahydrofuran or dioxane; and a base such as triethylamine is added.
  • a suitable solvent such as toluene, acetone, hydrazine, hydrazine-dimethylformamide, tetrahydrofuran or dioxane
  • a base such as triethylamine
  • a mixture of a nitrogen-oxygen bond and a double bond may be a J ⁇ or trans compound, or a mixture of cis and trans compounds in different proportions.
  • the compound of the formula (I) or (II) of the present invention has unexpectedly high herbicidal activity compared to known alkyl ester compounds, and is effective for use in pre- and post-emergence at lower doses. Control single and double cotyled weeds. Therefore, the technical solution of the present invention includes the use of the compound of the formula (I) or (II) for controlling weeds.
  • the present invention also encompasses a herbicidal composition having the compound of the formula (I) or (II) as an active ingredient.
  • the herbicidal composition has a concentration of the active ingredient of from 5 to 90% by weight.
  • an agriculturally acceptable carrier is also included in the herbicidal composition.
  • the herbicidal compositions of the invention can be administered in a variety of formulations.
  • the compound of the present invention is usually dissolved or dispersed in a carrier to prepare a formulation to be more easily dispersed as a herbicide.
  • a carrier for example: These chemicals can be formulated as wettable powders or creams. Therefore, in these compositions, at least one liquid or solid carrier is added, and it is usually necessary to add a suitable surfactant.
  • a further embodiment of the present invention is a method of controlling weeds which comprises applying a herbicidally effective amount of the herbicidal composition of the present invention to the surface of the weed or the weed growing or the surface of the growth medium thereof.
  • a more suitable effective amount is usually selected from 10 g to 1000 g per hectare, and an effective amount is preferably 20 g to 500 g per hectare.
  • one or more additional herbicides may be added to the herbicidal compositions of the present invention, thereby providing additional advantages and benefits.
  • the compound of the present invention may be used alone or in combination with other known insecticides, fungicides, plant growth regulators or fertilizers.
  • the temperature was 40-6 (rC, after stirring for 8 hours, ethyl acetate 200 mL and water 180 mL were added to the reaction solution, and the organic phase was washed with 180 mL of a saturated aqueous solution of sodium chloride, and then anhydrous magnesium sulfate was used.
  • the original pharmaceutically acceptable acetone or dimethyl sulfoxide is dissolved, and then 1% is used.
  • the Tween 80 solution is formulated into a desired concentration of 50 mL of the test solution, and the content of acetone or dimethyl sulfoxide in the total solution is not more than 10%.
  • Spray treatment was carried out using a crawler crop sprayer (designed and manufactured by Engineering Research Ltd., UK) (spray pressure 1.95 kg/cm 2 , spray volume 50 ml/m 2 , crawler speed 30 cm/s, nozzle nozzle fan).
  • Pre-emergence test The seeds of quantitative weeds (ramie, valerian, and crabgrass) were separately planted in culture rafts with a cross-sectional area of 100 cm 2 , and the soil was covered with soil for 1 cm after sowing. The test compound was sprayed on the soil surface and placed after treatment. The greenhouse is then watered to 1%. Tween 80 was placed in tap water treatment as a control.
  • the seeds of the quantitative weeds were separately planted in a culture raft having a cross-sectional area of 100 cm 2 , and the soil was covered with lcm after sowing, and cultured in a greenhouse according to a conventional method.
  • the test materials are selected to be sprayed after the seedlings are sprayed to 1%.
  • Tween 80 was placed in tap water treatment as a control. After the test materials are treated, they are placed in a dry and ventilated place. After the liquid is naturally dried, it is placed in a greenhouse and managed according to conventional methods. 48 hours after treatment. The method of watering from the bottom is adopted to prevent the liquid from being washed away.
  • Compound 12 was selected in parallel with the known compound Kd (Compound 17 in EP0223406) for herbicidal activity. The results are shown in Table 5.

Abstract

L'invention porte sur des composés esters d'acide 2-pyrimidinyloxy(sulfo)benzoxyoléfinique représentés par la formule générale (I) ou (II), les groupes substituants dans lesdites formules générales étant définis comme dans la présente description. Les présents composés représentés par la formule générale (I) ou (II) sont des agents actifs herbicides. Par comparaison avec les composés connus de l'état de la technique, les présents composés peuvent être utilisés pour une lutte efficace contre des mauvaises herbes à feuilles simples/doubles avec un dosage beaucoup plus faible dans la phase de pré-germination et/ou de post-germination.
PCT/CN2008/072516 2008-09-25 2008-09-25 Nouveaux composés esters d'acide 2-pyrimidinyloxy(sulfo)benzoxyoléfinique et leurs utilisations WO2010034153A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PCT/CN2008/072516 WO2010034153A1 (fr) 2008-09-25 2008-09-25 Nouveaux composés esters d'acide 2-pyrimidinyloxy(sulfo)benzoxyoléfinique et leurs utilisations

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/CN2008/072516 WO2010034153A1 (fr) 2008-09-25 2008-09-25 Nouveaux composés esters d'acide 2-pyrimidinyloxy(sulfo)benzoxyoléfinique et leurs utilisations

Publications (1)

Publication Number Publication Date
WO2010034153A1 true WO2010034153A1 (fr) 2010-04-01

Family

ID=42059268

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CN2008/072516 WO2010034153A1 (fr) 2008-09-25 2008-09-25 Nouveaux composés esters d'acide 2-pyrimidinyloxy(sulfo)benzoxyoléfinique et leurs utilisations

Country Status (1)

Country Link
WO (1) WO2010034153A1 (fr)

Cited By (34)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013040117A1 (fr) 2011-09-13 2013-03-21 Monsanto Technology Llc Procédés et compositions de lutte contre les mauvaises herbes
WO2013039990A1 (fr) 2011-09-13 2013-03-21 Monsanto Technology Llc Procédés et compositions de lutte contre les mauvaises herbes
WO2013040057A1 (fr) 2011-09-13 2013-03-21 Monsanto Technology Llc Procédés et compositions de lutte contre les mauvaises herbes
WO2013040021A1 (fr) 2011-09-13 2013-03-21 Monsanto Technology Llc Procédés et compositions de lutte contre les mauvaises herbes
WO2013040005A1 (fr) 2011-09-13 2013-03-21 Monsanto Technology Llc Procédés et compositions de lutte contre les mauvaises herbes
WO2013040049A1 (fr) 2011-09-13 2013-03-21 Monsanto Technology Llc Procédés et compositions pour lutter contre les mauvaises herbes
WO2014151255A1 (fr) 2013-03-15 2014-09-25 Monsanto Technology Llc Méthodes et compositions pour lutter contre les mauvaises herbes
WO2015108982A2 (fr) 2014-01-15 2015-07-23 Monsanto Technology Llc Procédés et compositions pour la lutte contre les mauvaises herbes utilisant des polynucléotides epsps
US9121022B2 (en) 2010-03-08 2015-09-01 Monsanto Technology Llc Method for controlling herbicide-resistant plants
CN105272925A (zh) * 2015-11-25 2016-01-27 常州大学 一种水稻田除草剂嘧草醚的制备方法
US9416363B2 (en) 2011-09-13 2016-08-16 Monsanto Technology Llc Methods and compositions for weed control
US9422557B2 (en) 2011-09-13 2016-08-23 Monsanto Technology Llc Methods and compositions for weed control
US9540642B2 (en) 2013-11-04 2017-01-10 The United States Of America, As Represented By The Secretary Of Agriculture Compositions and methods for controlling arthropod parasite and pest infestations
US9777288B2 (en) 2013-07-19 2017-10-03 Monsanto Technology Llc Compositions and methods for controlling leptinotarsa
US9850496B2 (en) 2013-07-19 2017-12-26 Monsanto Technology Llc Compositions and methods for controlling Leptinotarsa
US10041068B2 (en) 2013-01-01 2018-08-07 A. B. Seeds Ltd. Isolated dsRNA molecules and methods of using same for silencing target molecules of interest
CN108558777A (zh) * 2018-07-31 2018-09-21 河北大学 嘧啶水杨酸类衍生物及其制备方法与应用
US10240161B2 (en) 2012-05-24 2019-03-26 A.B. Seeds Ltd. Compositions and methods for silencing gene expression
US10378012B2 (en) 2014-07-29 2019-08-13 Monsanto Technology Llc Compositions and methods for controlling insect pests
US10557138B2 (en) 2013-12-10 2020-02-11 Beeologics, Inc. Compositions and methods for virus control in Varroa mite and bees
US10609930B2 (en) 2013-03-13 2020-04-07 Monsanto Technology Llc Methods and compositions for weed control
US10612019B2 (en) 2013-03-13 2020-04-07 Monsanto Technology Llc Methods and compositions for weed control
US10655136B2 (en) 2015-06-03 2020-05-19 Monsanto Technology Llc Methods and compositions for introducing nucleic acids into plants
US10683505B2 (en) 2013-01-01 2020-06-16 Monsanto Technology Llc Methods of introducing dsRNA to plant seeds for modulating gene expression
US10760086B2 (en) 2011-09-13 2020-09-01 Monsanto Technology Llc Methods and compositions for weed control
US10801028B2 (en) 2009-10-14 2020-10-13 Beeologics Inc. Compositions for controlling Varroa mites in bees
US10806146B2 (en) 2011-09-13 2020-10-20 Monsanto Technology Llc Methods and compositions for weed control
US10829828B2 (en) 2011-09-13 2020-11-10 Monsanto Technology Llc Methods and compositions for weed control
US10883103B2 (en) 2015-06-02 2021-01-05 Monsanto Technology Llc Compositions and methods for delivery of a polynucleotide into a plant
US10888579B2 (en) 2007-11-07 2021-01-12 Beeologics Inc. Compositions for conferring tolerance to viral disease in social insects, and the use thereof
US10968449B2 (en) 2015-01-22 2021-04-06 Monsanto Technology Llc Compositions and methods for controlling Leptinotarsa
US10988764B2 (en) 2014-06-23 2021-04-27 Monsanto Technology Llc Compositions and methods for regulating gene expression via RNA interference
US11091770B2 (en) 2014-04-01 2021-08-17 Monsanto Technology Llc Compositions and methods for controlling insect pests
US11807857B2 (en) 2014-06-25 2023-11-07 Monsanto Technology Llc Methods and compositions for delivering nucleic acids to plant cells and regulating gene expression

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1054590A (zh) * 1990-02-20 1991-09-18 Fmc有限公司 6-芳基-2-取代的苯甲酸除草剂
US5201937A (en) * 1990-10-26 1993-04-13 Basf Aktiengesellschaft Salicyclic acid derivatives
US5403816A (en) * 1990-10-25 1995-04-04 Kumiai Chemical Industry Co., Ltd. Picolinic acid derivative and herbicidal composition
CN101279951A (zh) * 2007-04-06 2008-10-08 沈阳化工研究院 2-嘧啶氧(硫)基苯甲酸基烯酸酯类化合物及其应用

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1054590A (zh) * 1990-02-20 1991-09-18 Fmc有限公司 6-芳基-2-取代的苯甲酸除草剂
US5403816A (en) * 1990-10-25 1995-04-04 Kumiai Chemical Industry Co., Ltd. Picolinic acid derivative and herbicidal composition
US5201937A (en) * 1990-10-26 1993-04-13 Basf Aktiengesellschaft Salicyclic acid derivatives
CN101279951A (zh) * 2007-04-06 2008-10-08 沈阳化工研究院 2-嘧啶氧(硫)基苯甲酸基烯酸酯类化合物及其应用

Cited By (53)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10888579B2 (en) 2007-11-07 2021-01-12 Beeologics Inc. Compositions for conferring tolerance to viral disease in social insects, and the use thereof
US10801028B2 (en) 2009-10-14 2020-10-13 Beeologics Inc. Compositions for controlling Varroa mites in bees
US11812738B2 (en) 2010-03-08 2023-11-14 Monsanto Technology Llc Polynucleotide molecules for gene regulation in plants
US9988634B2 (en) 2010-03-08 2018-06-05 Monsanto Technology Llc Polynucleotide molecules for gene regulation in plants
US9121022B2 (en) 2010-03-08 2015-09-01 Monsanto Technology Llc Method for controlling herbicide-resistant plants
WO2013040049A1 (fr) 2011-09-13 2013-03-21 Monsanto Technology Llc Procédés et compositions pour lutter contre les mauvaises herbes
US10806146B2 (en) 2011-09-13 2020-10-20 Monsanto Technology Llc Methods and compositions for weed control
WO2013040005A1 (fr) 2011-09-13 2013-03-21 Monsanto Technology Llc Procédés et compositions de lutte contre les mauvaises herbes
WO2013040021A1 (fr) 2011-09-13 2013-03-21 Monsanto Technology Llc Procédés et compositions de lutte contre les mauvaises herbes
US10829828B2 (en) 2011-09-13 2020-11-10 Monsanto Technology Llc Methods and compositions for weed control
US9416363B2 (en) 2011-09-13 2016-08-16 Monsanto Technology Llc Methods and compositions for weed control
US9422558B2 (en) 2011-09-13 2016-08-23 Monsanto Technology Llc Methods and compositions for weed control
US9422557B2 (en) 2011-09-13 2016-08-23 Monsanto Technology Llc Methods and compositions for weed control
US10808249B2 (en) 2011-09-13 2020-10-20 Monsanto Technology Llc Methods and compositions for weed control
EP3434780A1 (fr) 2011-09-13 2019-01-30 Monsanto Technology LLC Procédés et compositions de lutte contre les mauvaises herbes
WO2013040057A1 (fr) 2011-09-13 2013-03-21 Monsanto Technology Llc Procédés et compositions de lutte contre les mauvaises herbes
US10760086B2 (en) 2011-09-13 2020-09-01 Monsanto Technology Llc Methods and compositions for weed control
EP3296402A2 (fr) 2011-09-13 2018-03-21 Monsanto Technology LLC Procédés et compositions pour lutter contre les mauvaises herbes
WO2013039990A1 (fr) 2011-09-13 2013-03-21 Monsanto Technology Llc Procédés et compositions de lutte contre les mauvaises herbes
WO2013040117A1 (fr) 2011-09-13 2013-03-21 Monsanto Technology Llc Procédés et compositions de lutte contre les mauvaises herbes
EP3434779A1 (fr) 2011-09-13 2019-01-30 Monsanto Technology LLC Procédés et compositions de lutte contre les mauvaises herbes
EP3382027A2 (fr) 2011-09-13 2018-10-03 Monsanto Technology LLC Procédés et compositions de lutte contre les mauvaises herbes
US10240162B2 (en) 2012-05-24 2019-03-26 A.B. Seeds Ltd. Compositions and methods for silencing gene expression
US10240161B2 (en) 2012-05-24 2019-03-26 A.B. Seeds Ltd. Compositions and methods for silencing gene expression
US10934555B2 (en) 2012-05-24 2021-03-02 Monsanto Technology Llc Compositions and methods for silencing gene expression
US10041068B2 (en) 2013-01-01 2018-08-07 A. B. Seeds Ltd. Isolated dsRNA molecules and methods of using same for silencing target molecules of interest
US10683505B2 (en) 2013-01-01 2020-06-16 Monsanto Technology Llc Methods of introducing dsRNA to plant seeds for modulating gene expression
US10609930B2 (en) 2013-03-13 2020-04-07 Monsanto Technology Llc Methods and compositions for weed control
US10612019B2 (en) 2013-03-13 2020-04-07 Monsanto Technology Llc Methods and compositions for weed control
WO2014151255A1 (fr) 2013-03-15 2014-09-25 Monsanto Technology Llc Méthodes et compositions pour lutter contre les mauvaises herbes
US10568328B2 (en) 2013-03-15 2020-02-25 Monsanto Technology Llc Methods and compositions for weed control
US9850496B2 (en) 2013-07-19 2017-12-26 Monsanto Technology Llc Compositions and methods for controlling Leptinotarsa
US10597676B2 (en) 2013-07-19 2020-03-24 Monsanto Technology Llc Compositions and methods for controlling Leptinotarsa
US11377667B2 (en) 2013-07-19 2022-07-05 Monsanto Technology Llc Compositions and methods for controlling Leptinotarsa
US9856495B2 (en) 2013-07-19 2018-01-02 Monsanto Technology Llc Compositions and methods for controlling Leptinotarsa
US9777288B2 (en) 2013-07-19 2017-10-03 Monsanto Technology Llc Compositions and methods for controlling leptinotarsa
US10927374B2 (en) 2013-11-04 2021-02-23 Monsanto Technology Llc Compositions and methods for controlling arthropod parasite and pest infestations
US10100306B2 (en) 2013-11-04 2018-10-16 Monsanto Technology Llc Compositions and methods for controlling arthropod parasite and pest infestations
US9540642B2 (en) 2013-11-04 2017-01-10 The United States Of America, As Represented By The Secretary Of Agriculture Compositions and methods for controlling arthropod parasite and pest infestations
US10557138B2 (en) 2013-12-10 2020-02-11 Beeologics, Inc. Compositions and methods for virus control in Varroa mite and bees
WO2015108982A2 (fr) 2014-01-15 2015-07-23 Monsanto Technology Llc Procédés et compositions pour la lutte contre les mauvaises herbes utilisant des polynucléotides epsps
US10334848B2 (en) 2014-01-15 2019-07-02 Monsanto Technology Llc Methods and compositions for weed control using EPSPS polynucleotides
US11091770B2 (en) 2014-04-01 2021-08-17 Monsanto Technology Llc Compositions and methods for controlling insect pests
US10988764B2 (en) 2014-06-23 2021-04-27 Monsanto Technology Llc Compositions and methods for regulating gene expression via RNA interference
US11807857B2 (en) 2014-06-25 2023-11-07 Monsanto Technology Llc Methods and compositions for delivering nucleic acids to plant cells and regulating gene expression
US10378012B2 (en) 2014-07-29 2019-08-13 Monsanto Technology Llc Compositions and methods for controlling insect pests
US11124792B2 (en) 2014-07-29 2021-09-21 Monsanto Technology Llc Compositions and methods for controlling insect pests
US10968449B2 (en) 2015-01-22 2021-04-06 Monsanto Technology Llc Compositions and methods for controlling Leptinotarsa
US10883103B2 (en) 2015-06-02 2021-01-05 Monsanto Technology Llc Compositions and methods for delivery of a polynucleotide into a plant
US10655136B2 (en) 2015-06-03 2020-05-19 Monsanto Technology Llc Methods and compositions for introducing nucleic acids into plants
CN105272925A (zh) * 2015-11-25 2016-01-27 常州大学 一种水稻田除草剂嘧草醚的制备方法
CN108558777B (zh) * 2018-07-31 2021-01-26 河北大学 嘧啶水杨酸类衍生物及其制备方法与应用
CN108558777A (zh) * 2018-07-31 2018-09-21 河北大学 嘧啶水杨酸类衍生物及其制备方法与应用

Similar Documents

Publication Publication Date Title
WO2010034153A1 (fr) Nouveaux composés esters d'acide 2-pyrimidinyloxy(sulfo)benzoxyoléfinique et leurs utilisations
JP5416838B2 (ja) 置換アニリノピリミジン基を含有するｅ体フェニルアクリル酸エステル化合物及びそれらの使用
TW391957B (en) Fungicidal methods, compounds and compositions containing benzophenones
JP2828186B2 (ja) アクリレート系化合物、その製法及び殺菌剤
KR101402876B1 (ko) 제초성 우라실계 화합물 및 이를 포함하는 제초제
JPS63216848A (ja) プロペン酸誘導体、その製造法及びそれを含有する殺菌組成物
WO2009116151A1 (fr) Dérivés de 1-phényl-5-difluorométhylpyrazole-4-carboxamide et herbicides contenant les dérivés en tant qu’ingrédient actif
DK164595B (da) 3-methoxy-2-pyridyl-methylacrylater, fremgangsmaade til fremstilling deraf, middel indeholdende forbindelserne og disses eller midlets anvendelse til bekaempelse af svampe
DE19711953A1 (de) Neue Herbicide
FR2583266A1 (fr) Amines tertiaires fongicides nouvelles, compositions les contenant et leurs applications a la lutte contre des champignons
EP0076030A2 (fr) Dérivés d'amides substituées, leur procédé de préparation, compositions pesticides les contenant et les procédés pour combattre les mauvaises herbes et les champignons
JPH0331266A (ja) ピリミジン誘導体及び除草剤
JP2019529337A (ja) イソキサゾリン環を含むピリジン系化合物及び除草剤としての該用途
WO2009046665A1 (fr) Composés d'isoindole et leurs utilisations
EA000179B1 (ru) Производные пиразола
JPH0341442B2 (fr)
CN109867624B (zh) 一种3-氟-5-氯吡啶氧基苯氧丙酰胺类化合物及其应用
WO2021068815A1 (fr) Composé ester d'acide carboxylique et son application
JPH06192252A (ja) ピラジン誘導体および除草剤
FR2583265A1 (fr) Nouveaux composes heterocycliques et compositions fongicides les contenant
JPH0363266A (ja) アラルキルアミン誘導体、その製法及び殺菌、殺虫剤
JP2504072B2 (ja) 置換ベンゾイル誘導体および除草剤
JP3054977B2 (ja) 殺菌性フラノン誘導体
JPH0517453A (ja) ウラシル誘導体および除草剤
KR101866271B1 (ko) 벤조일사이클로헥산다이온 화합물 및 이 화합물을 포함하는 제초제

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: 08800988

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: 08800988

Country of ref document: EP

Kind code of ref document: A1