WO2005056518A1 - Composes d'ether d'oxime contenant du soufre ou de l'oxygene et possedant une activite biocide - Google Patents

Composes d'ether d'oxime contenant du soufre ou de l'oxygene et possedant une activite biocide Download PDF

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Publication number
WO2005056518A1
WO2005056518A1 PCT/CN2004/001282 CN2004001282W WO2005056518A1 WO 2005056518 A1 WO2005056518 A1 WO 2005056518A1 CN 2004001282 W CN2004001282 W CN 2004001282W WO 2005056518 A1 WO2005056518 A1 WO 2005056518A1
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Prior art keywords
methyl
oxime
formula
methylthio
sulfur
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PCT/CN2004/001282
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English (en)
Chinese (zh)
Inventor
Aiping Liu
Xiaoguang Wang
Xiaoming Ou
Xingping Liu
Mingzhi Huang
Yongjiang Wang
Hui Pei
Can Chen
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Hunan Research Institute Of Chemical Industry
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Publication of WO2005056518A1 publication Critical patent/WO2005056518A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/53—Nitrogen 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
    • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen
    • A01N35/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen containing a carbon-to-nitrogen double bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C317/28—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/46—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms, not being part of nitro or nitroso groups, further bound to other hetero atoms
    • C07C323/47—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms, not being part of nitro or nitroso groups, further bound to other hetero atoms to oxygen atoms

Definitions

  • the invention relates to sulfur-containing, oxime ether compounds having insecticidal and bactericidal activities and a preparation method thereof.
  • Chinese patent CN 1288002 discloses a part of biocidal sulfur-containing, oxime ether compounds and intermediate ketoxime compounds.
  • the present invention conducts a more extensive and in-depth study of sulfur-containing, oxime ether compounds, and synthesizes compounds containing the general formula (I). Sulfur, oxime ether compounds. A series of compounds have been found to have broad-spectrum activity. These compounds can be used to control pests and pathogens on a variety of crops, and some compounds can still achieve good results at very low doses.
  • the present invention uses the general formula (I) to represent sulfur-containing, oxime ether compounds:
  • R represents fluorenyl or halofluorenyl
  • V. t represents an integer from 0 to 5;
  • X represents 0, S, SO or S0 2 ;
  • N represents 0 or 1.
  • Fluorenyl A straight or branched fluorenyl group having 1 to 6 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, or different butyl, pentyl, and hexyl isomers.
  • Halogen refers to fluorine, chlorine, bromine and iodine.
  • Halofluorenyl refers to a straight or branched chain alkyl group having 1-6 carbon atoms.
  • the hydrogen atoms on these alkyl groups may be partially or completely replaced by halogen atoms.
  • dhaloalkyl groups such as chloromethyl, bromine Methyl, fluoromethyl, dichloromethyl, dibromomethyl, difluoromethyl, trichloromethyl, tribromomethyl, trifluoromethyl, chlorofluoromethyl, chlorobromomethyl, fluorochlorobromo methyl.
  • Phenoxy refers to a straight or branched chain alkoxy group having 1 to 6 carbon atoms, which is connected to the structure via an oxygen atom bond.
  • Fluorothio refers to a straight or branched chain alkylthio group with 1-6 carbon atoms, which is connected to the structure via a sulfur atom bond.
  • Haloalkoxy refers to a straight or branched chain alkoxy group having 1 to 6 carbon atoms. The hydrogen atoms on these alkoxy groups may be partially or completely replaced by halogen atoms.
  • haloalkoxy groups such as chloromethoxy Methyl, bromomethoxy, fluoromethoxy, dichloromethoxy, dibromomethoxy, difluoromethoxy, trichloromethoxy, tribromomethoxy, trifluoromethoxy, chlorofluoro Methoxy, chlorobromomethoxy, chlorofluorobromomethoxy.
  • Aryl refers to a phenyl group with 6 carbon atoms and a naphthyl group with 12 carbon atoms, biphenyl.
  • Heteroaryl A 5-membered ring, a 6-membered ring, a benzo 5-membered ring or a benzo 6-membered ring with one or more heteroatoms.
  • Ar is preferably a group as follows::
  • Rp 1 is the same or different and represents hydrogen, halogen, fluorenyl, fluorenyl, alkylthio, alkoxycarbonyl, haloalkyl, haloalkoxy, halofluorenylthio, haloalkoxycarbonyl;
  • P is an integer from 0 to 5;
  • Z is 0, S or NR 2 , R 2 is hydrogen, (-C 4 ) -alkyl, (C 6 -C 12 ) -aryl, heteroaryl having up to 10 carbon atoms.
  • Ar is particularly preferably a group shown below-
  • Ri 1 and R 2 1 are the same or different and represent hydrogen, halogen, alkyl, haloalkyl, fluorenyloxy, and 13 ⁇ 4 alkoxy.
  • Preferred compounds are compounds of the following general formula (I), wherein:
  • Ar is selected from a group shown below:
  • R is selected from methyl, trifluoromethyl
  • F t is selected from hydrogen, methyl, trifluoromethyl, phenoxy, pyridyloxy, phenyl, 4-fluorophenyloxy, and 4-fluoro-3-phenoxy t represents an integer of 1-5;
  • n is selected from 0, 1;
  • X is selected from sulfur or oxygen.
  • Particularly preferred compounds are compounds of the following general formula (I), wherein:
  • Ar is selected from a group shown below:
  • Ri and R2 1 are the same or different and represent hydrogen, halogen, amidino, halofluorenyl, alkoxy, haloalkane
  • R represents methyl
  • F t represents 3-phenoxy, 2-methyl-3-phenyl or 3-phenoxy-4-fluoro
  • N 0 or 1
  • X stands for sulfur or oxygen.
  • the compound represented by formula (I) can appear in two geometric isomers of formula Z and E.
  • the compound represented by the general formula (I) may be a racemate, a diastereomer or a pure optical isomer;
  • the compound represented by the general formula (I) relates not only to pure isomers but also to a mixture of various isomers.
  • the present invention also provides a method for preparing a sulfur-containing, oxygen, and oxime ether compound represented by the general formula (I), wherein the substituents are as defined above unless otherwise specified.
  • a suitable solvent is added in the presence of a suitable base such as alkali metal hydroxide, alkali metal carbonate, alkali metal alkoxide, alkali metal, alkali metal hydride, pyridine or tertiary amine.
  • a suitable base such as alkali metal hydroxide, alkali metal carbonate, alkali metal alkoxide, alkali metal, alkali metal hydride, pyridine or tertiary amine.
  • phase transfer catalyst such as tetrabutylammonium iodide, tetrabutylammonium bromide, tetraethyl Ammonium bromide or 18-crown ether-6, which is obtained by reacting at normal pressure and 0-120 ° C for 1-10 hours.
  • a phase transfer catalyst such as tetrabutylammonium iodide, tetrabutylammonium bromide, tetraethyl Ammonium bromide or 18-crown ether-6, which is obtained by reacting at normal pressure and 0-120 ° C for 1-10 hours.
  • Ar, R,, n, X and F t is as described above, L represents a leaving group such as chlorine, or
  • hydroxylamine hydrochloride or hydroxylamine sulfate in a suitable base such as alkali metal hydroxide, alkali metal carbonate, alkali metal bicarbonate, pyridine or triethylamine in a suitable solvent such as water and I or alcohol It is obtained by reacting at 0-100 ° C for 1-10 hours at normal pressure.
  • a suitable base such as alkali metal hydroxide, alkali metal carbonate, alkali metal bicarbonate, pyridine or triethylamine in a suitable solvent such as water and I or alcohol
  • the invention provides a method for preparing a compound of formula (IV):
  • ArMgBr + CH 3 OCH 2 CN ⁇ CH 3 OCH 2 C ( NMgBr) Ar ⁇ ArCOCH 2 OCH 3 where Ar is as described above.
  • the present invention provides a method for preparing a compound of formula (VII).
  • the general formula (i) of the present invention has sulfur-containing, oxime ether compounds which can effectively control pests and pathogenic bacteria on growing or harvested crops.
  • Sulfur-containing, oxime ether compounds of general formula (I) with a concentration of 100 ppm to 1000 ppm are generally used, dispersed in water or other liquid carriers, and applied to plants, crops, or soil where crops grow, which can effectively prevent crops from suffering Attack of pests and pathogens.
  • the sulfur-containing, oxime ether compounds of the general formula (I) of the present invention can effectively control pests when they are applied to plants, crops or soil where crops are grown in an amount of 0.060 kg / ha to about 4.000 kg / ha. .
  • the sulfur-containing, oxime ether compounds of the general formula (I) of the present invention are used alone, they are effective for controlling pests, and they can also be used together with other biochemical substances, and these biochemical substances include other pesticides.
  • the sulfur-containing, oxime ether compounds of the general formula (I) of the present invention can be effectively used together with pyrethroids, pyrethroids, carbamates, benzoyl urea pesticides, hydrazide pesticides, etc. Mixed use.
  • the above formula (I) containing sulfur and oxime ether compounds can be made into powders, wettable powders, granules, granules, emulsifiable concentrates, suspensions, dry suspensions, soluble powders, microemulsions, concentrated emulsions.
  • Water-dispersible granules, slow-release agents, tablets, etc., all of the above are suitable for application to soil, water, and / or plants to provide the plants with the required protection.
  • These preparations contain a compound of the present invention in admixture with an inert, pharmacologically acceptable solid or liquid diluent.
  • the wettable powders and powders of the present invention can be obtained by mixing about 5% -20% of the general formula (I) sulfur-containing, oxime ether compounds with about 5% -20% of solid anionic surfactants. Grinded together. In these systems 60-90% inert solid diluents such as talc, kaolin, diatomaceous earth, limestone, silicate, chalk, etc. are also used in the agent.
  • Granules are prepared by grinding approximately equal amounts, usually about 5-20 parts, of sulfur-containing, oxime ether compounds of the general formula (I), solid surfactants and about 60-90 parts of gypsum, then The mixture is compressed into particles of about 24/48 mesh or larger.
  • the emulsifiable concentrate is prepared by uniformly mixing 5-20 parts of the general formula (I) sulfur-containing, oxime ether compounds, 86-73 parts of a diluent such as xylene and 9-7 parts of a suitable auxiliary.
  • wettable powders and other liquid preparations can also be used. These liquid preparations are applied in situ with the aqueous solution ingredients and sprayed on the plants to be protected.
  • the solid preparations of general formula (I) containing sulfur and oxime ether compounds can be mixed with other pesticides, used as a multi-component mixture, or used in rotation.
  • liquid formula ⁇ ) sulfur-containing, oxime ether compound preparations when used in combination with other pesticides, they can be mixed in a container or applied sequentially as liquid sprays.
  • Example 1 1- (3-Fluoro-4-methylphenyl) -2-methylthio-0-[(2-methylbiphenyl-3-yl) methyl] oxime-1-ethyl ketone Synthesis [Compound No. 001 of general formula (I) in Table 1] (systhesis of lp-fluoro-metliylphenyD-S-inethylthio- OI S-methylbiphenyl-S-yDniethyl] oxime 1-ethanone)
  • Example 2 Synthesis of 1- (4-chloro-3-fluorophenyl) -2-methylthio-0-[(2-methyl-3-biphenyl) methyl] oxime 1-ethanone [ Compound of general formula (I) in Table 1] (systhesis of 1-(4-chloro-3-fluorophenyl) -2-methylthio -O- [(2-methyl-3 -biphenyl) methyl] oxime 1-ethanone)
  • Example 3 Synthesis of l- (3-chloro-4-fluorophenyl) -2-methylthio-0-[(2-methyl-3-biphenyl) methyl] oxime 1-ethyl ketone [ Compound of Formula (I) No. 003 in Table 1] (systhesis of 1-(3-chloro-4-fluorophenyl)-2-methylthio-O- [(2-methyl- 3 -biphenyl) methyl] oxime 1-ethanone)
  • Example 5 Synthesis of l- (4-methoxyphenyl) -2-methoxy-0-[(2-methylbiphenyl-3-yl) methyl] oxime 1-ethanone [Table 1 compound of general formula (I) in 029] (systhesis of l- (4-methoxylphenyl) -2-methoxy-0-[(2-me thyl-biphenyl-3 -yl) methyl] oxime 1-etliai one)
  • the emulsifiable concentrate or wettable powder containing sulfur and oxime ether compounds provided by the present invention prepared according to the method of the above-mentioned example of agricultural preparations is diluted with water to prepare a pesticide solution of a predetermined concentration.
  • the slimeworm and 5-8 one-inch-long corn leaves were placed in a petri dish for quantitative spraying. After drying, they were moved into the observation room for normal word culture. After 24 hours, the deaths were counted. The experiment was repeated 3 times, and the results were averaged.
  • the sulfur-containing, oxime ether compound-containing emulsifiable concentrate or wettable powder provided by the present invention prepared according to the method of the above-mentioned example of agricultural preparations is diluted with water to prepare a predetermined concentration of pesticide solution, and the bean aphid is connected to the newly unearthed bean sprouts. Each plant receives 25 or more heads, and then the bean sprouts and the test insects are immersed in the medicinal solution. After 5 seconds, they are taken out, the excess medicinal solution is aspirated, inserted into the absorbent sponge, and covered with a glass tube. 24 hours later Check the number of live and dead insects. Repeat 3 times and average the results.
  • the emulsified emulsifiable concentrate or wettable powder containing sulfur and oxime ether compounds provided by the present invention prepared according to the method of the example of the above-mentioned agricultural preparations is diluted with water to prepare a pesticide solution of a predetermined concentration, and the two-core rice seedlings are immersed in the chemical solution. 5 After a few seconds, take them out to dry, put them in large test tubes, 20 plants per tube, and then introduce 20 black-tailed leafhoppers 5 nymphs. The mouth of the tube was wrapped with white gauze and placed under observation room conditions. After 24 hours, check the survival and Number of dead insects. The experiment was repeated 3 times, and the results were averaged.
  • the synthesized compound also has extremely significant activity against other pests such as Spodoptera exigua, Spodoptera litura, Spodoptera exigua, and Myzus persicae.
  • Table 2 shows the biological activities of some of the compounds of general formula (I) synthesized against armyworm, leafhopper and bean sprouts.
  • Method A (toxic medium method): The sulfur-containing, oxime ether compounds provided by the present invention are formulated into a mother liquor of a predetermined concentration with a suitable diluent (such as acetone), and 1 ml of the medicinal solution is taken at 50 with a pipette.
  • a suitable diluent such as acetone
  • Method B Plant samples are potted.
  • the sulfur-containing, oxime ether compounds provided by the present invention are suitable for
  • a suitable diluent such as acetone
  • Spray application on the plant samples and inoculation of the disease 24 hours later. After inoculation, the plants were placed in a constant temperature incubator to allow the infection to continue, and the results were investigated after the control had fully developed the disease.
  • the activity classification is as follows: A (90-100% protection effect), B (70-90% protection effect), C (50-70% protection effect), D (50% or less protection effect).
  • Botrytis cinerea 500ppm, method B
  • rape sclerotium 500ppm, method B
  • rice blast pathogen 25ppm, method A

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne des composés d'éther d'oxime contenant du soufre ou de l'oxygène représentés par la formule générale (I), dans laquelle R, R1, X, n, Ar et Ft sont tels que définis dans la spécification, ainsi que leurs procédés de préparation. Lesdits composés représentés par la formule générale (I) présentent une excellente activité biologique, notamment, dans la lutte contre les insectes nuisibles dans les domaines de l'agriculture, de l'horticulture, de la culture des fleurs et de l'hygiène. Lesdits composés représentés par la formule générale (I) possèdent une activité insecticide rapide et persistante et n'endommagent pas les cultures.
PCT/CN2004/001282 2003-12-12 2004-11-11 Composes d'ether d'oxime contenant du soufre ou de l'oxygene et possedant une activite biocide WO2005056518A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN 200310110647 CN100579956C (zh) 2003-12-12 2003-12-12 杀虫、杀菌的含硫、氧肟醚类化合物
CN200310110647.1 2003-12-12

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Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102030680B (zh) * 2010-10-20 2014-03-26 湖北省生物农药工程研究中心 具有杀虫活性的肟醚或酯衍生物及其用途
CN102228044B (zh) * 2011-05-11 2013-04-24 海利尔药业集团股份有限公司 一种含有硫氟肟醚的杀虫组合物
CN102239875A (zh) * 2011-05-17 2011-11-16 海利尔药业集团股份有限公司 一种含有硫氟肟醚与部分烟碱类化合物的杀虫组合物
CN102326538A (zh) * 2011-10-31 2012-01-25 湖南化工研究院 硫氟肟醚微囊悬浮剂及制备方法与用途
EP2649879A1 (fr) 2012-04-10 2013-10-16 Basf Se Mélanges de pesticides contenant de fluxapyroxad
CN102911093B (zh) * 2012-10-25 2014-08-13 湖南化工研究院 一种硫氟肟醚的制备方法
CN103053558A (zh) * 2013-01-16 2013-04-24 海利尔药业集团股份有限公司 一种含有硫氟肟醚与螺虫乙酯的杀虫组合物
CN103734180B (zh) * 2013-12-30 2015-12-30 刘一平 一种含有硫氟肟醚的杀菌杀虫组合物
CN103980179A (zh) * 2014-05-29 2014-08-13 厦门大学 一种吲哚取代肟醚类化合物及其制备方法与应用

Citations (5)

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Publication number Priority date Publication date Assignee Title
EP0004754A2 (fr) * 1978-03-31 1979-10-17 Rhone-Poulenc Agrochimie Ethers de cétoximes à activité insecticide
CN1250046A (zh) * 1998-10-07 2000-04-12 湖南化工研究院 杀生物的肟醚类化合物
CN1288002A (zh) * 1999-09-10 2001-03-21 湖南化工研究院 杀生物的烷基－取代(杂)－芳基－酮肟－o－醚及中间体酮、肟类化合物及其制备方法
EP1125931A1 (fr) * 2000-02-17 2001-08-22 Hunan Research Institute of Chemical Industry (Hétéro)aryl-kétoxime-O-éthers alkyle substitués et méthode pour les fabriquer
CN1387515A (zh) * 1999-11-05 2002-12-25 日本曹达株式会社 肟o－醚化合物与农业和园艺用的杀菌剂

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0004754A2 (fr) * 1978-03-31 1979-10-17 Rhone-Poulenc Agrochimie Ethers de cétoximes à activité insecticide
CN1250046A (zh) * 1998-10-07 2000-04-12 湖南化工研究院 杀生物的肟醚类化合物
CN1288002A (zh) * 1999-09-10 2001-03-21 湖南化工研究院 杀生物的烷基－取代(杂)－芳基－酮肟－o－醚及中间体酮、肟类化合物及其制备方法
CN1387515A (zh) * 1999-11-05 2002-12-25 日本曹达株式会社 肟o－醚化合物与农业和园艺用的杀菌剂
EP1125931A1 (fr) * 2000-02-17 2001-08-22 Hunan Research Institute of Chemical Industry (Hétéro)aryl-kétoxime-O-éthers alkyle substitués et méthode pour les fabriquer

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CN100579956C (zh) 2010-01-13

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