CN102696593A - Benzene-ring-containing trifluorobutene insecticides - Google Patents

Benzene-ring-containing trifluorobutene insecticides Download PDF

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Publication number
CN102696593A
CN102696593A CN2012101980402A CN201210198040A CN102696593A CN 102696593 A CN102696593 A CN 102696593A CN 2012101980402 A CN2012101980402 A CN 2012101980402A CN 201210198040 A CN201210198040 A CN 201210198040A CN 102696593 A CN102696593 A CN 102696593A
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Prior art keywords
compound
insecticides
ethanol
butylene
phenyl ring
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CN102696593B (en
Inventor
许辉
唐剑峰
李凝
刘杰
王丹丹
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WEIFANG ZHONGNONG UNITED CHEMICAL CO Ltd
SHANDONG UNITED PESTICIDE INDUSTRY Co Ltd
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WEIFANG ZHONGNONG UNITED CHEMICAL CO Ltd
SHANDONG UNITED PESTICIDE INDUSTRY Co Ltd
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    • 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
    • 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
    • C07D213/60—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 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
    • C07D213/61—Halogen atoms or nitro radicals

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pyridine Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention provides benzene-ring-containing trifluorobutene insecticides. A structure of the compounds is shown in the specification. The insecticides are prepared by the following steps of: (1) dissolving 3-methyl-4-methylthiophenol into ethanol, adding pre-dried potassium carbonate, and dripping 4-bromo-1,1,2-trifluoro-1-butene at normal temperature; (2) reacting at the temperature of 50 to 60 DEG C after the dripping of the 4-bromo-1,1,2-trifluoro-1-butene is finished; (3) filtering a solution obtained after reaction in step (2) to obtain an ethanol solution; and (4) leaching a solid by using ethanol, mixing obtained ethanol solutions, distilling under reduced pressure to remove the ethanol to obtain a compound, and purifying the compound by using chromatography, wherein a chromatographic solution is that the ratio of n-hexane to ethyl acetate is 7.5:2.5, 235.8g of yellowish liquid is obtained, and the structure of the compounds is shown in the specification. The insecticides are particularly used for killing nematodes, and have the advantages of remarkable nematode-killing effect and low preparation cost and using cost.

Description

A kind of trifluoro butylene insecticides that contains phenyl ring
Technical field
The present invention relates to agricultural chemicals, is a kind of trifluoro butylene insecticides that contains phenyl ring.
Background technology
It is the openest as far back as the U.S. that the trifluoro butene compounds has nematicide activity, and afterwards, states such as Japan, China also disclose the multiple nematicidal compound that is different from the United States Patent (USP) structure.These different compounds each have different features when nematicide.For example: disclosed compound in 00809783.6 patent, though have nematicide performance,, its preparation cost is high, and usage amount is higher.
Summary of the invention
The purpose of this invention is to provide a kind of trifluoro butylene insecticides that contains phenyl ring, it is exclusively used in nematicide, and makes it have significant nematicide effect, the advantage that preparation cost and use cost are low.
The present invention realizes through following technical scheme for realizing above-mentioned purpose: a kind of trifluoro butylene insecticides that contains phenyl ring, and the structure of compound is:
Figure 2012101980402100002DEST_PATH_IMAGE002
（1），
Wherein, n=0,1,2.
Described a kind of preparation method who contains the trifluoro butylene insecticides of phenyl ring, the structure of producing compound is:
Figure 839893DEST_PATH_IMAGE002
（1），
Wherein, n=0,3-methyl-4-methylthiophenol and halogenating agent react under atent solvent and make.
Described a kind of preparation method who contains the trifluoro butylene insecticides of phenyl ring makes with compound (2) and oxidant reaction:
Figure 452271DEST_PATH_IMAGE002
(1); Wherein, N=1,2.
Described a kind of purposes that contains the trifluoro butylene insecticides of phenyl ring; Compound (1)
Wherein, n=0,1,2, be used for nematicide.
Described a kind of preparation method who contains the trifluoro butylene insecticides of phenyl ring; The structure of producing compound is: compound
Figure 2012101980402100002DEST_PATH_IMAGE006
(2); N=0
Preparation process is following:
1. get in 95% ethanol that 1 mole of 3-methyl-4-methylthiophenol is dissolved in 1000 milliliters, add 1.15 moles in the dry in advance potash of crossing again, drip 4-bromo-1,1 at normal temperatures, 1.05 moles of 2-three fluoro-1-butylene;
2. with 4-bromo-1,1, after 2-three fluoro-1-butylene dropwise, reacted 8 hours down at 50-60 ℃;
3. the 2. middle reacted solution of step is filtered, contained the ethanolic solution of
Figure 218550DEST_PATH_IMAGE004
(2);
4. use 95% ethanol drip washing solid 3-6 time; Merge the ethanolic solution that obtains; Ethanol is removed in decompression distillation; Obtain compound
Figure 412507DEST_PATH_IMAGE004
(2); With chromatography purification compound
Figure 562997DEST_PATH_IMAGE004
(2); Wherein chromatographic solution is n-hexane: ethyl acetate=7.5:2.5; Obtain yellowish liquid 235.8 grams, compound structure is:
Figure 144151DEST_PATH_IMAGE004
(2).
Insecticide of the present invention has high activity, is exclusively used in nematicide, and its nematicide effect is remarkable.It and various crops have favorable compatibility.It can be used for preventing that Pratylenchidae from belonging to; The ball Heterodera: potato is worm completely; Heterodera: soybean cyst nematode; Meloidogyne: aphelenchoides besseyi, similes thorne, fuller's teasel stem eelworm, the nematode of partly puncturing; The minute hand Turbatrix; Xiphinema; The burr Turbatrix; Umbrella Aphelenchoides: pine wood nematode etc.
Insecticide according to the invention can be processed regular dosage form: emulsion, an aqueous dispersion material agent, wettable powder, microcapsules etc.
Insecticide of the present invention is specially adapted to prevent and treat Pratylenchidae and belongs to, like potato all fronts worm; Soybean cyst nematode; Meloidogyne; Aphelenchoides besseyi; Pine wood nematode.
The reactive compound of insecticide of the present invention can use separately; Process the insecticide of various formulations; Also can be used with other insecticidal activity thing, can with known bactericide, nematocide carry out composite, to enlarge insecticidal spectrum or to be used to prevent to develop immunity to drugs.
Insecticide preparation method of the present invention does not have special installation and requirement, and preparation cost is low, owing to have high insecticidal activity, can reduce use cost.
The present invention draws through measuring the desinsection drug effect, and control efficiency is remarkable.Test formulation: 1 part of reactive compound
Figure 417000DEST_PATH_IMAGE002
(1)
(wherein; N=0) add 9 parts of kaolin; Prepare and contain reactive compound
Figure 83605DEST_PATH_IMAGE002
(1)
(wherein, n=0) 10% fine granular.
This reagent is used for banana root-knot nematode 2 instars extremely.Before the medication, record average 72 every mu of banana root-knot nematode 2 instars, every mu is used 10% fine granular is 4 kilograms; After the medication 30 days, the survival of banana root-knot nematode is 2 for every mu, and control efficiency is 97.3%; After the medication 60 days, 3.6 every mu of banana root-knot nematode survivals, control efficiency is 95%; Above-mentioned test repetition 6 times, effect are mean.
Embodiment
A kind of trifluoro butylene insecticides that contains phenyl ring of the present invention, the structure of compound is:
Figure 100103DEST_PATH_IMAGE002
（1），
Wherein, n=0,1,2.
A kind of preparation method who contains the trifluoro butylene insecticides of phenyl ring of the present invention, the structure of producing compound is:
Figure 535763DEST_PATH_IMAGE002
（1），
Wherein, n=0,3-methyl-4-methylthiophenol and halogenating agent react under atent solvent and make.
Described a kind of preparation method who contains the trifluoro butylene insecticides of phenyl ring; Make
Figure 130485DEST_PATH_IMAGE002
(1) with compound
Figure 242164DEST_PATH_IMAGE004
(2) and oxidant reaction
Wherein, n=1,2.
Described a kind of purposes that contains the trifluoro butylene insecticides of phenyl ring; Compound
Figure 950674DEST_PATH_IMAGE002
(1)
Wherein, n=0,1,2, be used for nematicide.
Embodiment 1: described a kind of preparation method who contains the trifluoro butylene insecticides of phenyl ring; The structure of producing compound is: compound
Figure 240841DEST_PATH_IMAGE006
(2); Wherein, N=0
Preparation process is following:
1. get in 95% ethanol that 1 mole of 3-methyl-4-methylthiophenol is dissolved in 1000 milliliters, add 1.15 moles in the dry in advance potash of crossing again, drip 4-bromo-1,1 at normal temperatures, 1.05 moles of 2-three fluoro-1-butylene;
2. with 4-bromo-1,1, after 2-three fluoro-1-butylene dropwise, reacted 8 hours down at 50-60 ℃;
3. the 2. middle reacted solution of step is filtered, contained the ethanolic solution of
Figure 121072DEST_PATH_IMAGE004
(2);
4. use 95% ethanol drip washing solid 3-6 time; Merge the ethanolic solution that obtains; Ethanol is removed in decompression distillation; Obtain compound
Figure 496690DEST_PATH_IMAGE004
(2); With chromatography purification compound
Figure 854990DEST_PATH_IMAGE004
(2); Wherein chromatographic solution is n-hexane: ethyl acetate=7.5:2.5; Obtain yellowish liquid 235.8 grams; Compound structure is:
Figure 265243DEST_PATH_IMAGE004
(2)
HPLC analyzes, and content is 99%, and yield is 93%, and elementary analysis is: C:54.95%, H:5.0%, F:21.73%, O:6.10%, S:12.22 %.
Example 2: described a kind of preparation method who contains the trifluoro butylene insecticides of phenyl ring; The structure of producing compound is: compound
Figure 2012101980402100002DEST_PATH_IMAGE008
(1); N=1 wherein
Preparation process is following:
Get compound
Figure 194671DEST_PATH_IMAGE006
(2), n=0,1 mole is dissolved in 3000 milliliters 95% methyl alcohol; The hydrogen peroxide solution that adds 1.1 moles again, reaction is 48 hours under the 20-30 degree, adds sodium sulphite and destroys remaining oxidant; Add 3000 ml waters, with 1000 milliliters of extractions of carrene 4 times, combined dichloromethane layer; Decompression distillation is desolvated; Purify with chromatography, wherein chromatographic solution is n-hexane: ethyl acetate=8:2, obtains solid 208.5 grams of off-white color; Compound structure is:
Figure 57585DEST_PATH_IMAGE008
(1); Wherein, n=1
HPLC analyzes, and content is 99%, and yield is that 75%. elementary analyses are: C:51.79%, H:4.71%, F:20.48%, O:11.50%, S:11.52 %.
Example 3: described a kind of preparation method who contains the trifluoro butylene insecticides of phenyl ring; The structure of producing compound is: compound
Figure 2012101980402100002DEST_PATH_IMAGE010
(1); Wherein, N=2
Preparation process is following:
Get in 95% ethanol that (1) 1 mole of compound
Figure 157259DEST_PATH_IMAGE008
is dissolved in 1000 milliliters; The hydrogen peroxide solution that adds 0.3 mole again refluxed 8 hours, added sodium sulphite and destroyed remaining oxidant; Add 5000 milliliters in water; With 2000 milliliters of extractions of ethyl acetate four times, the combined ethyl acetate layer, decompression distillation is desolvated; Purify with chromatography; Wherein chromatographic solution is n-hexane: ethyl acetate=4:6, obtains faint yellow solid 191.2 grams, and compound structure is:
Figure 94122DEST_PATH_IMAGE010
（1），
HPLC analyzes, and content is 99%, and yield is 65%, elementary analysis: C:48.97% H:4.45%, F:19.37%, O:16.31%, S:10.90 %.

Claims (5)

1. trifluoro butylene insecticides that contains phenyl ring, it is characterized in that: the structure of compound is:
Figure 2012101980402100001DEST_PATH_IMAGE002
（1），
Wherein, n=0,1,2.
2. a kind of preparation method who contains the trifluoro butylene insecticides of phenyl ring according to claim 1, it is characterized in that: the structure of producing compound is:
Figure 307110DEST_PATH_IMAGE002
（1），
Wherein, n=0,3-methyl-4-methylthiophenol and halogenating agent react under atent solvent and make.
3. a kind of preparation method who contains the trifluoro butylene insecticides of phenyl ring according to claim 1 is characterized in that: make with compound
Figure 2012101980402100001DEST_PATH_IMAGE004
(2) and oxidant reaction:
Figure 996849DEST_PATH_IMAGE002
(1); Wherein, N=1,2.
4. the described a kind of purposes that contains the trifluoro butylene insecticides of phenyl ring of claim 1; It is characterized in that: compound
Figure 756994DEST_PATH_IMAGE002
(1); Wherein, n=0,1; 2, be used for nematicide.
5. a kind of preparation method who contains the trifluoro butylene insecticides of phenyl ring according to claim 1; It is characterized in that: the structure of producing compound is: compound
Figure 2012101980402100001DEST_PATH_IMAGE006
(2); N=0 wherein
Preparation process is following:
1. get in 95% ethanol that 1 mole of 3-methyl-4-methylthiophenol is dissolved in 1000 milliliters, add 1.15 moles in the dry in advance potash of crossing again, drip 4-bromo-1,1 at normal temperatures, 1.05 moles of 2-three fluoro-1-butylene;
2. with 4-bromo-1,1, after 2-three fluoro-1-butylene dropwise, reacted 8 hours down at 50-60 ℃;
3. the 2. middle reacted solution of step is filtered, contained the ethanolic solution of
Figure 890605DEST_PATH_IMAGE004
(2);
4. use 95% ethanol drip washing solid 3-6 time; Merge the ethanolic solution that obtains; Ethanol is removed in decompression distillation; Obtain compound
Figure 27188DEST_PATH_IMAGE004
(2); With chromatography purification compound
Figure 633750DEST_PATH_IMAGE004
(2); Wherein chromatographic solution is n-hexane: ethyl acetate=7.5:2.5; Obtain yellowish liquid 235.8 grams, compound structure is: (2).
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Cited By (2)

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WO2017054524A1 (en) * 2015-09-30 2017-04-06 山东省联合农药工业有限公司 Nematicide of trans structure containing lactone ring and preparation method and use thereof
CN114075300A (en) * 2020-08-21 2022-02-22 佛山市海力盈生物科技有限公司 Novel chitosan oligosaccharide derivative nematocide and preparation method and application thereof

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Publication number Priority date Publication date Assignee Title
CN109845741A (en) * 2018-11-26 2019-06-07 刘西芳 Nematicidal composition containing furfural

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CN1064479A (en) * 1991-03-01 1992-09-16 孟山都公司 Fluorinated alkenyl chain compound and as wormer
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Publication number Priority date Publication date Assignee Title
WO2017054524A1 (en) * 2015-09-30 2017-04-06 山东省联合农药工业有限公司 Nematicide of trans structure containing lactone ring and preparation method and use thereof
CN114075300A (en) * 2020-08-21 2022-02-22 佛山市海力盈生物科技有限公司 Novel chitosan oligosaccharide derivative nematocide and preparation method and application thereof
CN114075300B (en) * 2020-08-21 2023-02-28 佛山市海力盈生物科技有限公司 Chitosan oligosaccharide derivative nematicide and preparation method and application thereof

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