WO2007112618A1 - Dérivés de carbamate de méthyle contenant du iminoéther de vinyle et leur utilisation comme fongicides - Google Patents

Dérivés de carbamate de méthyle contenant du iminoéther de vinyle et leur utilisation comme fongicides Download PDF

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Publication number
WO2007112618A1
WO2007112618A1 PCT/CN2006/000917 CN2006000917W WO2007112618A1 WO 2007112618 A1 WO2007112618 A1 WO 2007112618A1 CN 2006000917 W CN2006000917 W CN 2006000917W WO 2007112618 A1 WO2007112618 A1 WO 2007112618A1
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WO
WIPO (PCT)
Prior art keywords
oily
compound
oil
formula
reaction
Prior art date
Application number
PCT/CN2006/000917
Other languages
English (en)
Chinese (zh)
Inventor
Weidong Liu
Shenghua Du
Chenglai Zhang
Shilin Lan
Chunhui Mao
Lu Huang
Xiaoguang Wang
Original Assignee
Hunan Research Institute Of Chemical Industry
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Hunan Research Institute Of Chemical Industry filed Critical Hunan Research Institute Of Chemical Industry
Publication of WO2007112618A1 publication Critical patent/WO2007112618A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C291/00—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00
    • C07C291/02—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00 containing nitrogen-oxide bonds
    • C07C291/04—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00 containing nitrogen-oxide bonds containing amino-oxide bonds
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof

Definitions

  • the present invention relates to a bactericidal activity-containing vinyl oxirane group-containing urethane compound and a process for the preparation thereof.
  • German Patent DE 4423612 discloses N-substituted phenyl carbamate compounds which have fungicidal properties.
  • the vinyl ether group-containing urethane-containing bactericidal active compound according to the present invention has not been reported in the literature.
  • An object of the present invention is to provide a bactericidal activity-containing vinyl ether ether group-containing carbamate compound represented by the formula (I) and a process for producing the same, and the formula (I) is as follows -
  • R 2 and R 3 are alkyl groups; R 4 and R 5 are each hydrogen or an alkyl group; and R B is a substituted aryl group or a substituted heteroaryl group.
  • a five-membered ring, six-membered ring or fused heterocyclic ring containing one or more N, 0, S heteroatoms For example, furan, pyridinium, pyrimidine, pyridazine, triazine, pyrazine, benzofuran, thiazole, benzothiazole or pyrazole.
  • the general formula (I) includes Z-type and E-type geometric isomers formed by different substituents of a carbon-nitrogen double bond and a carbon-carbon double bond, and a mixture thereof in any ratio.
  • R, R 2 , R 3 , R 4 , R 5 , R 6 have the same meanings as defined above; and Z is a leaving group such as halogen (chloro, bromo or iodo).
  • the compound of the formula (II) and the compound of the formula (III) are added to the solvent under basic conditions, and the base is added at 0 ° C.
  • the reaction of the compound of formula (I) is obtained by the reaction at 80 ° C for 0.2 to 5 hours, and the crude product is purified to give the compound of formula (I).
  • the solvent used is a benzene solvent such as benzene, toluene, xylene, chlorobenzene, etc.; a hydrocarbon solvent such as cyclohexane, petroleum ether, hexanyl, hydrazine, etc.; halogenated hydrocarbon such as dichloromethane, trichloro Methane, dichloroethane, trichloroethane, etc.; and tetrahydrofuran, dimethylformamide or dimethyl sulfoxide; ketone solvents such as acetone, methyl ethyl ketone; preferred solvents are toluene, dichloroethane, two Chloroformamide, tetrahydrofuran, dimethylformamide, dimethyl sulfoxide, methyl e
  • the compound of the formula (I) can control diseases caused by various fungi such as Algae, Oomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes, which have systemic activity and can be used as leaf and soil to kill Fungal agent. It is especially suitable for controlling rice blast; rice powdery mildew on barley, wheat, cucumber, melon, loofah, pumpkin and other cucurbit crops, apple powdery mildew, grape powdery mildew and other powdery mildew on plants; tomato, Gray mold on vegetables and fruits such as cucumbers, grapes; Fusarium oxysporum; Phytophthora capsici and Sclerotinia sclerotiorum.
  • fungi such as Algae, Oomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes, which have systemic activity and can be used as leaf and soil to kill Fungal agent. It is especially suitable for controlling rice blast; rice powdery mildew on barley,
  • the germicidal spectrum can be expanded and synergistically bactericidal.
  • the test for various fungal diseases of plants using the compound of the formula (I) of the present invention is as follows - potted plant samples are grown in a greenhouse and allowed to stand for a certain period of time. The compound of the formula (I) is dissolved in a small amount of N,N-dimethylformamide, diluted with water to the desired concentration, and the preparation is diluted with water to the desired concentration. The plant samples were sprayed and applied, and the water samples were taken as a control.
  • the plant samples were placed in a ventilated place to allow the surface liquid of the plants to air dry, and the pathogens were inoculated 24 hours later. After the inoculation, the plants are placed in a constant temperature and humidity incubator to continue the infection of the pathogen. A few days after the inoculation, the incidence index of each agent treatment was investigated when the control was sufficiently ill.
  • Class A Control effect 90% ⁇ 100%
  • Class B Control effect 70% ⁇ 90. /.
  • Class C Control effect 50 ⁇ 90%
  • Class D Control effect below 50%.
  • the compound of the present invention can have a synergistic bactericidal action in combination with the following fungicides: diniconazole, myclobutanil, pulverizine, benomyl, thiabendazole, carbendazim, thiophanate-methyl, chlorothalonil, Bordeaux mixture, bismuth octyl salt, Jinggangmycin, soil fungus, scleroside, Fuji No.1, chunleimycin, mancozeb, mancozeb, sensitized zinc, polyoxomycin, methyl dexame zinc , thiram, tridemorpholine, enoylmorpholine, metalaxyl and the like.

Landscapes

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

Abstract

La présente invention concerne des dérivés de carbamate de méthyle contenant du iminoéther de vinyle de formule générale (I), dans laquelle: R1, R2 et R3 sont indépendamment alkyle; R4 et R5 sont indépendamment hydrogène ou alkyle; R6 est aryle substitué ou hétéroaryle substitué; ainsi que leur procédé de préparation. Les composés selon la présente invention sont utilisés pour prévenir les maladies sur divers corps provoquées par les champignons phytopathogènes des classes suivantes: Phycomycetes, Oomycetes, Ascomycetes, Basidiomycetes, Deuteromycetae et analogues. Ces composés possédant une activité systématique peuvent être utilisés comme fongicides foliaires et ou du sol, notamment pour prévenir le flétrissement de la gaine de la chaume du riz; le blanc de l'orge ou du blé, Erysiphe Cichoracearum de corps de cucurbitacées, par exemple, le concombre, le melon, le louffa, le potiron et analogues; la moisissure grise de légume ou de fruit, par exemple, la tomate, le concombre, le raisin; Erysiphe Graminis; Phytophthora Capsici ou Sclerotinia Sclerotiorum et analogues. Les composés peuvent être mélangés avec d'autres fongicides, entraînant un spectre fongicide élargi et des activités fongicides synergiques.
PCT/CN2006/000917 2006-04-05 2006-05-08 Dérivés de carbamate de méthyle contenant du iminoéther de vinyle et leur utilisation comme fongicides WO2007112618A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CNB2006100314697A CN100388886C (zh) 2006-04-05 2006-04-05 含乙烯基肟醚基的氨基甲酸酯类杀菌化合物
CN200610031469.7 2006-04-05

Publications (1)

Publication Number Publication Date
WO2007112618A1 true WO2007112618A1 (fr) 2007-10-11

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CN2006/000917 WO2007112618A1 (fr) 2006-04-05 2006-05-08 Dérivés de carbamate de méthyle contenant du iminoéther de vinyle et leur utilisation comme fongicides

Country Status (2)

Country Link
CN (1) CN100388886C (fr)
WO (1) WO2007112618A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017024971A1 (fr) * 2015-08-12 2017-02-16 沈阳中化农药化工研发有限公司 Composé d'oximino-éther insaturé et son utilisation
KR20230046122A (ko) * 2021-09-29 2023-04-05 주식회사 팜한농 고순도 n-아실 유도체의 제조방법

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5869517A (en) * 1994-07-06 1999-02-09 Basf Aktiengesellschaft 2- (dihydro)pyrazol-3'-yloxymethylene!anilides, their preparation and their use
US5977399A (en) * 1994-11-23 1999-11-02 Basf Aktiengesellschaft Iminooxymethyleneanilides, preparation thereof and intermediates therefor, and compositions containing them
US6075049A (en) * 1995-11-02 2000-06-13 Basf Aktiengesellschaft Phenylcarbamates, processes and intermediate products for their preparation and their use as pesticides and fungicides
US6232339B1 (en) * 1998-07-21 2001-05-15 Basf Aktiengesellschaft Phenylcarbamates, their preparation, and compositions comprising them
CN1523013A (zh) * 2003-09-05 2004-08-25 湖南化工研究院 具有杀菌活性的n－取代苯基氨基甲酸酯类化合物及其制备方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1179942C (zh) * 2002-09-13 2004-12-15 湖南化工研究院 具有杀菌活性的含硫不饱和肟醚类化合物及其制备方法

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5869517A (en) * 1994-07-06 1999-02-09 Basf Aktiengesellschaft 2- (dihydro)pyrazol-3'-yloxymethylene!anilides, their preparation and their use
US5977399A (en) * 1994-11-23 1999-11-02 Basf Aktiengesellschaft Iminooxymethyleneanilides, preparation thereof and intermediates therefor, and compositions containing them
US6075049A (en) * 1995-11-02 2000-06-13 Basf Aktiengesellschaft Phenylcarbamates, processes and intermediate products for their preparation and their use as pesticides and fungicides
US6232339B1 (en) * 1998-07-21 2001-05-15 Basf Aktiengesellschaft Phenylcarbamates, their preparation, and compositions comprising them
CN1523013A (zh) * 2003-09-05 2004-08-25 湖南化工研究院 具有杀菌活性的n－取代苯基氨基甲酸酯类化合物及其制备方法

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CN1843121A (zh) 2006-10-11
CN100388886C (zh) 2008-05-21

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