CN116063226B - Ether compound containing monoterpene phenol structure - Google Patents
Ether compound containing monoterpene phenol structure Download PDFInfo
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- CN116063226B CN116063226B CN202310245713.3A CN202310245713A CN116063226B CN 116063226 B CN116063226 B CN 116063226B CN 202310245713 A CN202310245713 A CN 202310245713A CN 116063226 B CN116063226 B CN 116063226B
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- monoterpene
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- ether
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 229930003658 monoterpene Natural products 0.000 title claims abstract description 14
- 235000002577 monoterpenes Nutrition 0.000 title claims abstract description 14
- -1 Ether compound Chemical class 0.000 title claims abstract description 12
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 27
- 150000001875 compounds Chemical class 0.000 abstract description 16
- 239000003899 bactericide agent Substances 0.000 abstract description 9
- 235000018597 common camellia Nutrition 0.000 abstract description 7
- 150000002773 monoterpene derivatives Chemical class 0.000 abstract description 7
- 239000005740 Boscalid Substances 0.000 abstract description 6
- 240000001548 Camellia japonica Species 0.000 abstract description 6
- 125000003118 aryl group Chemical group 0.000 abstract description 6
- WYEMLYFITZORAB-UHFFFAOYSA-N boscalid Chemical compound C1=CC(Cl)=CC=C1C1=CC=CC=C1NC(=O)C1=CC=CN=C1Cl WYEMLYFITZORAB-UHFFFAOYSA-N 0.000 abstract description 6
- 229940118790 boscalid Drugs 0.000 abstract description 6
- 241000213004 Alternaria solani Species 0.000 abstract description 5
- 241000813090 Rhizoctonia solani Species 0.000 abstract description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract description 4
- 244000000004 fungal plant pathogen Species 0.000 abstract description 4
- 125000000627 niacin group Chemical group 0.000 abstract description 2
- 229940125904 compound 1 Drugs 0.000 description 17
- 229940125782 compound 2 Drugs 0.000 description 17
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 16
- 241000196324 Embryophyta Species 0.000 description 11
- RECUKUPTGUEGMW-UHFFFAOYSA-N carvacrol Chemical compound CC(C)C1=CC=C(C)C(O)=C1 RECUKUPTGUEGMW-UHFFFAOYSA-N 0.000 description 8
- HHTWOMMSBMNRKP-UHFFFAOYSA-N carvacrol Natural products CC(=C)C1=CC=C(C)C(O)=C1 HHTWOMMSBMNRKP-UHFFFAOYSA-N 0.000 description 8
- 239000005844 Thymol Substances 0.000 description 7
- 235000007746 carvacrol Nutrition 0.000 description 7
- WYXXLXHHWYNKJF-UHFFFAOYSA-N isocarvacrol Natural products CC(C)C1=CC=C(O)C(C)=C1 WYXXLXHHWYNKJF-UHFFFAOYSA-N 0.000 description 7
- 229960000790 thymol Drugs 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 230000001580 bacterial effect Effects 0.000 description 6
- 239000000341 volatile oil Substances 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000000575 pesticide Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 3
- CNQCWYFDIQSALX-UHFFFAOYSA-N 3-(chloromethyl)pyridine Chemical compound ClCC1=CC=CN=C1 CNQCWYFDIQSALX-UHFFFAOYSA-N 0.000 description 2
- 208000031888 Mycoses Diseases 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- 244000000005 bacterial plant pathogen Species 0.000 description 2
- 230000003385 bacteriostatic effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 230000009036 growth inhibition Effects 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 150000002611 lead compounds Chemical class 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
- 241000209507 Camellia Species 0.000 description 1
- 235000005135 Micromeria juliana Nutrition 0.000 description 1
- 240000007673 Origanum vulgare Species 0.000 description 1
- 235000010677 Origanum vulgare Nutrition 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 240000002114 Satureja hortensis Species 0.000 description 1
- 235000007315 Satureja hortensis Nutrition 0.000 description 1
- 235000007303 Thymus vulgaris Nutrition 0.000 description 1
- 240000002657 Thymus vulgaris Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 238000012271 agricultural production Methods 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229940125797 compound 12 Drugs 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000004080 punching Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000001585 thymus vulgaris Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P3/00—Fungicides
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
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- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Environmental Sciences (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
An ether compound containing a monoterpene phenol structure relates to the technical field of agriculture, in particular to a bactericidal compound. The compound is formed by splicing a nicotinic acid structure and monoterpene phenol through ether bonds. The compound disclosed by the invention has excellent antibacterial activity on three plant pathogenic fungi of alternaria solani, camellia anthracis and rhizoctonia solani, and the antibacterial activity on the camellia anthracis far higher than that of a commercial bactericide boscalid. The overall antibacterial activity is superior to that of a picolyl-phenyl ether compound without a monoterpene structure, and the monoterpene phenol pyridylmethyl ether compound with other aromatic rings has potential application prospect in the field of plant pathogenic fungi resistance.
Description
Technical Field
The invention relates to the technical field of agriculture, in particular to a bactericidal compound.
Background
The occurrence and prevalence of plant diseases severely restrict the development of agricultural production and threaten the quality safety of agricultural products. Pesticides are commonly used for plant disease control, and are dominant in plant protection. The plant essential oil has the advantages of simplicity, easiness in obtaining, safety to non-target organisms, good environmental compatibility and the like, and is widely used for preventing and controlling agricultural diseases. However, the components of the plant essential oil are complex and various, the plant essential oil is often different and diversified due to factors such as species, varieties, geographical distribution, growing seasons and the like, and the plant essential oil is easy to volatilize and has poor stability, so that the plant essential oil is difficult to directly use as pesticide.
Natural monoterpene phenols such as carvacrol (2-methyl-5-isopropyl phenol) and thymol (thymol, 2-isopropyl-5-methyl phenol) widely exist in essential oils of various plants such as origanum vulgare, thyme and savory, have good growth inhibition effect on various agricultural diseases, are known from the Chinese pesticide information network, and carvacrol water aqua is registered in China for preventing and treating various plant fungal diseases, and has good growth inhibition effect on Alternaria solani @Alternaria solani) Camellia anthracisColletotrichum camelliae) Rhizoctonia solani (wall.) kuntzeRhizoctonia solani) All have certain inhibition effect and have potential of further development and application as lead compounds. However, compared with commercial bactericides, the antibacterial activity of the monoterpene phenol compound has a gap, and the monoterpene phenol compound contains phenolic hydroxyl groups, is easy to oxidize, is difficult to directly use as pesticide, and needs to further improve the activity and stability through structural modification. The modification of the natural product structure is an effective means from lead compounds to the creation of active ingredients of bactericides, the pyridine structure is a common active functional group in bactericides, and the ether structure is stable under neutral, alkaline and weak acidic conditions and is a common group for protecting phenolic hydroxyl groups. In the prior art, no report of designing a novel bactericide molecule by combining a nicotinic acid structure and monoterpene phenol through ether bonds has been found.
Disclosure of Invention
The invention aims to provide a novel ether compound containing a monoterpene phenol structure, which can be applied to the prevention and treatment of plant fungal diseases.
An ether compound containing a monoterpene phenol structure, which has the structural formula:
wherein R is 1 Is CH (CH) 3 ) 2 , R 2 Is CH 3 Or R 1 Is CH 3 , R 2 Is CH (CH) 3 ) 2 。
The compound disclosed by the invention has excellent antibacterial activity on three plant pathogenic fungi of alternaria solani, camellia anthracis and rhizoctonia solani, and the antibacterial activity on the camellia anthracis far higher than that of a commercial bactericide boscalid. The overall antibacterial activity is superior to that of a picolyl-phenyl ether compound without a monoterpene structure, and the monoterpene phenol pyridylmethyl ether compound with other aromatic rings has potential application prospect in the field of plant pathogenic fungi resistance.
Drawings
FIG. 1 shows the molecular structural formula of the compound of the invention.
FIG. 2 is a synthetic route for compound 1 of the present invention.
FIG. 3 is a synthetic route for compound 2 of the present invention.
The specific embodiment is as follows:
example 1: the structural formula of the ether compound containing the monoterpene phenol structure is a compound 1 or a compound 2.
Compound 1:
compound 2:
the synthetic routes of compound 1 and compound 2 are shown in fig. 2 and 3.
The specific synthesis steps of the compound 1 are as follows:
step 1, 1 mmol carvacrol was dissolved in 5 mL DMF and 3 mmol potassium carbonate was added.
Step 2, 1.5 mmol of 3-chloromethylpyridine was dissolved in 1mL of DMF and slowly added dropwise to carvacrol solution at room temperature.
Step 3, TLC tracks the reaction progress, after the reaction is completed, the organic phases are extracted and combined, and the organic phases are dried and concentrated for column chromatography to obtain the target compound 1, wherein the yield is 74.41%.
Characterization data for compound 1 were: 1 H NMR (500 MHz, Chloroform-d) δ 8.72 (s, 1H), 8.59 (d,J= 4.9 Hz, 1H), 7.80 (d,J= 7.8 Hz, 1H), 7.33 (dd,J= 7.9, 4.8 Hz, 1H), 7.09 (d,J= 7.4 Hz, 1H), 6.81 – 6.76 (m, 2H), 5.10 (s, 2H), 2.92 – 2.83 (m, 1H), 2.24 (d,J= 0.9 Hz, 3H), 1.25 (d,J= 6.9 Hz, 6H). 13 C NMR (126 MHz, Chloroform-d) δ 156.44, 149.25, 148.83, 148.04, 135.05, 133.11, 130.71, 124.39, 123.50, 118.81, 109.85,67.48, 34.13, 24.14, 15.94. MS calcd for C 16 H 19 NO m/z 241.15, found 241.20, data indicate that this compound 1 is structurally correct.
The specific synthesis steps of the compound 2 are as follows:
step 1, 1 mmol thymol was dissolved in 5 mL DMF and 3 mmol potassium carbonate was added.
Step 2, 1.5 mmol of 3-chloromethylpyridine was dissolved in 1mL of DMF and slowly added dropwise to thymol solution at room temperature.
Step 3, TLC tracks the reaction progress, after the reaction is completed, the organic phases are extracted and combined, and the target compound 2 is obtained through dry concentration column chromatography, and the yield is 67.33%.
Characterization data for compound 2 were: 1 H NMR (500 MHz, Chloroform-d) δ 8.72 (s, 1H), 8.59 (d,J= 4.9 Hz, 1H), 7.79 (d,J= 9.9 Hz, 1H), 7.34 (d,J= 4.8 Hz, 1H), 7.14 (d,J= 7.7 Hz, 1H), 6.80 (d,J= 7.7 Hz, 1H), 6.75 (s, 1H), 5.08 (s, 2H), 3.38 – 3.29 (m, 1H), 2.33 (s, 3H), 1.21 (d,J= 6.9 Hz, 6H). 13 C NMR (126 MHz, Chloroform-d) δ 155.42, 149.21, 148.74, 136.46, 134.98, 134.37, 133.13, 126.15, 123.54, 121.89, 112.56, 67.58, 26.61, 22.81, 21.36. MS calcdfor C 16 H 19 NO m/z 241.15, found 241.20, data indicate that this compound 2 is structurally correct。
The antibacterial activity of the compound 1 and the compound 2 on plant pathogenic bacteria Alternaria solani, camellia anthracis and Rhizoctonia solani is measured by adopting a hypha growth rate method.
The hypha growth rate method specifically comprises the following steps: dissolving a compound to be tested with a certain amount of dimethyl sulfoxide (DMSO), preparing mother liquor with the concentration of 5000 mug/mL, adding the mother liquor and the culture medium in the volume ratio of 1:100 when the PDA culture medium is cooled to 45 ℃, fully and uniformly mixing, pouring the mixture into culture dishes with the diameter of 9 cm, and preparing a plate treatment group with the final concentration of 50 mug/mL by 15 mL per dish; the blank control group was added with DMSO in an amount equivalent to that of the treatment group; boscalid at the same concentration was used as a positive control group and a picolyl-phenyl ether homolog and a monoterpenyl-methyl aromatic ring ether homolog were used as comparative examples. After the tested pathogenic bacteria are activated for two generations, a puncher with the inner diameter of 5 mm is used for punching bacterial cakes at the edge of a bacterial colony, the bacterial cakes are respectively inoculated on a PDA flat plate with medicines and a blank control, the bacterial colonies are cultivated in the dark for a certain time at the temperature of 26+/-0.5 ℃, and when the bacterial colony of the blank control group grows to the edge of the flat plate, the diameter of the bacterial colony is measured by a crisscross method.
The method is repeated three times, and the average inhibition rate and standard deviation of different compounds on the growth of hyphae of several plant pathogenic bacteria are calculated according to the three measurement results. The results are shown in table 1 below:
TABLE 1
As can be seen from table 1:
the antibacterial activity of the compound 1 and the compound 2 against Alternaria solani is equivalent to that of the commercial bactericide boscalid, and is higher than that of the parent compounds carvacrol and thymol. Compared with other picolyl-phenyl ether compounds without monoterpene structure, the antibacterial activity of the compounds 1 and 2 is higher than that of picolyl-phenyl ether homologs 1-4. Of the monoterpene-methyl aromatic ring ether homologs, only ether homolog 11 containing thiazole groups has the same antibacterial activity as that of compound 1 and compound 2, and other compounds have lower antibacterial activity than that of compound 1 and compound 2.
For camellia anthracnose, the antibacterial activity of the compound 1 and the compound 2 is higher than that of carvacrol, thymol which are parent compounds and the commercial bactericide boscalid. The bacteriostatic activity of compounds 1 and 2 is higher than that of picolyl-phenyl ether homologues 1-4, compared with other picolyl-phenyl ether homologues without monoterpene structure. The antibacterial activity of the compound 1 and the compound 2 is higher than that of other monoterpene-methyl aromatic ring ether homologues.
The antibacterial activity of the rhizoctonia solani, the compound 1 and the compound 2 is slightly higher than that of carvacrol, thymol which are parent compounds and the commercial bactericide boscalid. The bacteriostatic activity of compounds 1 and 2 is higher than that of picolyl-phenyl ether homologues 1-4, compared with other picolyl-phenyl ether homologues without monoterpene structure. Of the monoterpene-methyl aromatic ring ether homologs, only ether compound 12 containing thiazole groups has the antibacterial activity equivalent to that of compound 1 and compound 2, and other compounds are lower than that of compound 1 and compound 2.
Claims (1)
1. An ether compound containing a monoterpene phenol structure, which has the structural formula:
wherein R is 1 Is CH (CH) 3 ) 2 , R 2 Is CH 3 。
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| DE10122097A1 (en) * | 2000-07-24 | 2002-02-07 | Bayer Ag | Pyrazolylbiphenylcarboxamide |
| AU2010268837A1 (en) * | 2009-07-08 | 2012-02-02 | Bayer Intellectual Property Gmbh | Phenyl(oxy/thio)alkanol derivatives |
| CN109810062A (en) * | 2019-01-24 | 2019-05-28 | 云南农业大学 | A kind of phenylimidazole derivatives and its synthetic method and the application in pesticide |
| CN109942427A (en) * | 2019-04-17 | 2019-06-28 | 云南农业大学 | A kind of monoterpene phenol derivatives and its synthetic method and the application in pesticide |
| CN112321513A (en) * | 2020-11-06 | 2021-02-05 | 中国药科大学 | Heterocyclic compound and preparation method and application thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2013298562A1 (en) * | 2012-08-03 | 2015-02-19 | Bayer Cropscience Ag | Composition comprising a pesticidal terpene mixture and a fungicide |
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| DE10122097A1 (en) * | 2000-07-24 | 2002-02-07 | Bayer Ag | Pyrazolylbiphenylcarboxamide |
| AU2010268837A1 (en) * | 2009-07-08 | 2012-02-02 | Bayer Intellectual Property Gmbh | Phenyl(oxy/thio)alkanol derivatives |
| CN109810062A (en) * | 2019-01-24 | 2019-05-28 | 云南农业大学 | A kind of phenylimidazole derivatives and its synthetic method and the application in pesticide |
| CN109942427A (en) * | 2019-04-17 | 2019-06-28 | 云南农业大学 | A kind of monoterpene phenol derivatives and its synthetic method and the application in pesticide |
| CN112321513A (en) * | 2020-11-06 | 2021-02-05 | 中国药科大学 | Heterocyclic compound and preparation method and application thereof |
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