CN103951619A - Methoxyl imino acetamide compounds containing aryl pyrazole and use - Google Patents
Methoxyl imino acetamide compounds containing aryl pyrazole and use Download PDFInfo
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- CN103951619A CN103951619A CN201410208190.6A CN201410208190A CN103951619A CN 103951619 A CN103951619 A CN 103951619A CN 201410208190 A CN201410208190 A CN 201410208190A CN 103951619 A CN103951619 A CN 103951619A
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- Prior art keywords
- alkyl
- methoxyl
- compounds containing
- containing aryl
- carbonyl
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
- C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
Abstract
The invention discloses methoxyl imino acetamide compounds containing aryl pyrazole, the structure of which is shown as a formula (I) in the specification, wherein in the formula, R(n) is selected from cyan, nitro, alkyl, alkenyl, alkynyl, halogenated alkyl, alkoxyl, halogenated alkoxyl, alkyl sulphanyl, alkyl carbonyl, alkoxyl carbonyl, alkyl amino, fluorine, bromine and iodine. The invention further discloses an application of the compounds in preparing bactericides.
Description
Technical field
The invention belongs to disinfectant use in agriculture field.Be specifically related to a kind of methoxyimino acetamides containing arylpyrazole and in the application of preparing aspect sterilant.
Technical background
Alkene oxime amine, chemical name: (E, E, E)-N-methyl-2-[((((1-methyl-3-(2,6-dichlorophenyl)-2-propenyl) imino-) oxygen base) methyl) phenyl]-2-methoxyimino acetic amide, be commonly called as: SYP-1620, be the strobilurin fungicide taking natural antibiotics as lead compound that Shenyang Chemical Engineering Inst finds for 1999, within 2003, obtain Chinese invention patent (patent No.: ZL00110143.9).Alkene oxime amine fungicidal spectrum is wide, active high, there is preventive and therapeutic action, plurality of plant diseases is all had to good prevention effect, and environmentally friendly, to crop safety, its pharmacophore methoxyimino acetamide structure is subject to extensive concern (molecules2010 in the research and development of novel pesticide, 13,9024-9034).
From the angle of sterilant initiative, so that roughly the same synthesis method and active group splice principle as guiding theory, the N-arylpyrazole structure of the methoxyimino ethanamide poisoning group of alkene oxime amine being introduced to Strobilurin, has designed and synthesized a kind of methoxyimino acetamides containing arylpyrazole.Test by fungicidal activity, find that this compounds has good fungicidal activity, being expected to exploitation becomes sterilant new variety.
Summary of the invention
The object of the present invention is to provide a kind of novel methoxyimino acetamides containing arylpyrazole just with fungicidal activity under very little dosage.
Technical scheme of the present invention is as follows:
The invention provides a kind of methoxyimino acetamides containing arylpyrazole, as shown in general formula I:
Wherein, R
(n)middle n=1-5 replaces, R
(n)be selected from respectively halogen, cyano group, nitro, C
1-C
6alkyl, C
2-C
6thiazolinyl, C
2-C
6alkynyl, C
1-C
6haloalkyl, C
1-C
6alkoxyl group, C
1-C
6halogenated alkoxy, C
1-C
6alkylthio, C
1-C
6alkyl-carbonyl, C
1-C
6alkoxy carbonyl, C
1-C
6alkylamino, the halogen in wherein said halogeno-group is selected from one or more in fluorine, bromine or iodine.
Can the present invention be described with the compound of listing in following table 1, but not limit the present invention.
Table 1
| Numbering | R (n) |
| 1 | 2-CH 3 |
| 2 | 4-F |
| 3 | 3-CF 3-4-F |
| 4 | 4-CF 3 |
| 5 | 3-CF 3 |
| 6 | 4-OCF 3 |
| 7 | 4-OCH 3 |
| 8 | 4-CH(CH 3) 2 |
| 9 | 4-CF(CF 3) 2 |
| 10 | 4-Br |
| 11 | 3-F |
| 12 | 3-I |
| 13 | 2，4-NO 2 |
| 14 | 3，4-OCH 3 |
| 15 | 3，4，5-OCH 3 |
The methoxyimino acetamides containing arylpyrazole shown in general formula I is made by substitution reaction by N-aryl-3-hydroxypyrazoles and (E)-N-methyl-2-(2-2-bromomethylphenyl)-2-methoxyimino acetic amide, can reference literature J.Heterocyclic Chem.2010,49,1370 etc.
Compound of the present invention can be prepared sterilant, can be applicable to the microbial multiple diseases such as sclerotinia rot of colza sensitive strain Sclerotinia sclerotiorum, eliminating vegetable botrytis sensitive strain Botryris cinerea Pers., wheat scab sensitive strain Gibbrella zeae (Schw.) Petch, rice sheath blight disease sensitive strain Rhizoctorua solani or Pyricularia oryzae Pyricularia oryzae Cav.
Novel pyrazole oxime ether-ether compounds of the present invention can, as the disease control of various crop, comprise the medicinal plant of ginseng, Radix Panacis Quinquefolii, pseudo-ginseng, the bighead atractylodes rhizome, the bulb of fritillary, fructus amomi, chrysanthemum, matrimony vine or lily; The land for growing field crops plant of wheat, corn, paddy rice, potato, beet, peanut or cotton; The vegetable crop of Chinese cabbage, tomato, cucumber, capsicum or French beans; The garden crop of peach, pears, grape or strawberry; The flowers of kafir lily or aloe.
The embodiment that fungicidal activity is measured
Carry out sterilization effect evaluation with the compound in table 1.
Contrast medicament: alkene oxime amine and Strobilurin.
Target: sclerotinia rot of colza sensitive strain Sclerotinia sclerotiorum, eliminating vegetable botrytis sensitive strain Botryris cinerea Pers., wheat scab sensitive strain Gibbrella zeae (Schw.) Petch, rice sheath blight disease sensitive strain Rhizoctorua solani, Pyricularia oryzae Pyricularia oryzae Cav.
Trial crops: potted plant cotyledon period cucumber seedling.
Treatment agent amount: in vitro: 10ppm, 1ppm, 0.1ppm; Live body: 1000ppm.
Isolated test method and live test method are with reference to patent CN103275009A and CN103613542A etc., and concrete outcome sees the following form 1, table 2.
Partial test result is as follows:
The in vitro fungicidal activity result table of table 1
Table 2 live body fungicidal activity result table
Grade scale: A level: inhibiting rate >=90%; B level: 90% > inhibiting rate >=70%; C level: 70% > inhibiting rate >=50%; D level: 50% > inhibiting rate.
Although with preferred embodiment in detail the present invention has been described in detail, but it is not intended to limit the present invention.Any those skilled in the art, without departing from the spirit and scope of the present invention, should make various amendments and change.Therefore protection scope of the present invention should be considered as appended claims limited range.
Claims (2)
1. contain a methoxyimino acetamides for arylpyrazole, as shown in general formula I:
Wherein:
R
(n)middle n=1-5 replaces, R
(n)be selected from respectively halogen, cyano group, nitro, C
1-C
6alkyl, C
2-C
6thiazolinyl, C
2-C
6alkynyl, C
1-C
6haloalkyl, C
1-C
6alkoxyl group, C
1-C
6halogenated alkoxy, C
1-C
6alkylthio, C
1-C
6alkyl-carbonyl, C
1-C
6alkoxy carbonyl, C
1-C
6alkylamino, the halogen in wherein said halogeno-group is selected from one or more in fluorine, bromine or iodine.
2. one kind if the compound as described in arbitrary in claim 1 is in the application of preparing aspect sterilant.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410208190.6A CN103951619A (en) | 2014-05-16 | 2014-05-16 | Methoxyl imino acetamide compounds containing aryl pyrazole and use |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410208190.6A CN103951619A (en) | 2014-05-16 | 2014-05-16 | Methoxyl imino acetamide compounds containing aryl pyrazole and use |
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| Publication Number | Publication Date |
|---|---|
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Family
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| Application Number | Title | Priority Date | Filing Date |
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| CN201410208190.6A Pending CN103951619A (en) | 2014-05-16 | 2014-05-16 | Methoxyl imino acetamide compounds containing aryl pyrazole and use |
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| Country | Link |
|---|---|
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3031325A1 (en) | 2014-12-10 | 2016-06-15 | Basf Se | Method for combating soybean rust comprising treating soybean with (2E)-2-[2-[[1-(2,4-substi-tuted-phenyl)pyrazol-3-yl]oxymeth¬yl]-3-sub¬stituted-phenyl]-2-methoxyimino-n-methyl-acet-amides |
| CN105924435A (en) * | 2016-06-23 | 2016-09-07 | 浙江工业大学 | Substituted pyrazole acetamide compound and preparation method and application thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1309897A (en) * | 2000-02-24 | 2001-08-29 | 沈阳化工研究院 | Unsaturated oximino ether bactericide |
-
2014
- 2014-05-16 CN CN201410208190.6A patent/CN103951619A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1309897A (en) * | 2000-02-24 | 2001-08-29 | 沈阳化工研究院 | Unsaturated oximino ether bactericide |
Non-Patent Citations (5)
| Title |
|---|
| 孙旭峰,等: "具有生物活性的1-芳基吡唑类化合物的研究进展", 《农药》, vol. 50, no. 11, 30 November 2011 (2011-11-30), pages 781 - 789 * |
| 思彬彬,等.: "甲氧基丙烯酸酯类杀菌剂作用机理研究进展", 《世界农药》, vol. 29, no. 6, 31 December 2007 (2007-12-31), pages 5 - 9 * |
| 柏亚罗: "Strobilurins类杀菌剂研究开发进展", 《农药》, vol. 46, no. 5, 31 May 2007 (2007-05-31) * |
| 王丽,等.: "甲氧基丙烯酸酯类杀菌剂研究进展", 《农药科学与管理》, vol. 29, no. 9, 30 September 2008 (2008-09-30), pages 24 - 27 * |
| 马海军,等.: "吡唑醚菌酯的合成和初步生物活性", 《农药》, vol. 52, no. 6, 30 June 2013 (2013-06-30), pages 408 - 410 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3031325A1 (en) | 2014-12-10 | 2016-06-15 | Basf Se | Method for combating soybean rust comprising treating soybean with (2E)-2-[2-[[1-(2,4-substi-tuted-phenyl)pyrazol-3-yl]oxymeth¬yl]-3-sub¬stituted-phenyl]-2-methoxyimino-n-methyl-acet-amides |
| CN105924435A (en) * | 2016-06-23 | 2016-09-07 | 浙江工业大学 | Substituted pyrazole acetamide compound and preparation method and application thereof |
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Application publication date: 20140730 |