CN108484538A - A kind of synthetic method of the nematicide containing lactonic ring - Google Patents
A kind of synthetic method of the nematicide containing lactonic ring Download PDFInfo
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- CN108484538A CN108484538A CN201810585415.8A CN201810585415A CN108484538A CN 108484538 A CN108484538 A CN 108484538A CN 201810585415 A CN201810585415 A CN 201810585415A CN 108484538 A CN108484538 A CN 108484538A
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- butylene
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
Abstract
The invention discloses a kind of synthetic methods of the nematicide containing lactonic ring, include the following steps：2 (2 methoxyphenyl) 5 oxo-tetrahydrofuran, 3 carboxylic acid is dissolved in solvent, it stirs evenly, organic alkali is added thereto and carries out salt-forming reaction, then 4 bromines 1 are added thereto, 1,2 trifluoro, 1 butylene carries out substitution reaction and obtains reaction solution, then through overpickling, alkali cleaning, liquid separation, organic phase is evaporated under reduced pressure and removes solvent, obtain [2 (2 methoxyphenyl) 5 oxo-tetrahydrofuran, 3 base] formic acid [4 (1,1,2 trifluoro, 1 butylene) base] ester；What the present invention solved 41,1,2 trifluoro of bromine, 1 butylene and carboxylic acid reacts halfway defect, the decomposition of 41,1,2 trifluoro of bromine, 1 butylene is reduced simultaneously, the yield of product can reach 85% or more, and when in particular by DBU or tetramethylguanidine, product yield can reach 90% or more；And this method postprocessing working procedures are simple, are suitble to large-scale industrial production, greatly reduce production cost, accelerate the promotion and application of new product.
Description
Technical field
The present invention relates to technical field of organic synthesis, the synthetic method of specifically a kind of nematicide containing lactonic ring.
Background technology
[2- (2- methoxyphenyls) -5- oxo-tetrahydrofuran -3- bases]-formic acid [4- (tri- fluoro- 1- butylene of 1,1,2-) base]
Ester is a kind of novel nematicide, and existing preparation method is the synthetic method of routine, with 2- (2- methoxyphenyls) -5- oxygen
For tetrahydrofuran -3- carboxylic acids and 4- bromo- 1,1,2- tri- fluoro- 1- butylene is raw material, in Conventional solvents such as methanol, acetonitrile, acetone etc.
In, the acid binding agent such as potassium carbonate, sodium carbonate the effects that under carry out that target compound is obtained by the reaction.But it have been found that in routine
With 4- bromo- 1 in synthetic method, 1,2- tri- fluoro- 1- butylene calculated yield only reaches 58.9%, but 4- bromo- 1,1,2- tri- fluoro- 1- fourths
Alkene price is very expensive, causes the nematicide cost higher, limits its popularization and application.
《The research of carboxylic acid and carboxylate and the direct synthetic ester of halogenated hydrocarbons》In, carboxylic acid and carboxylate are in triethylamine or three second
Amine directly acetify reacting, the present invention is tested with reference to this article, fails to obtain such as in the presence of sodium iodide with halogenated hydrocarbons
Test result described in data.It is compared by theory analysis and repetition test, it has been found that the main reason for product yield is low be
4- bromo- 1,1,2- tri- fluoro- 1- butylene with there is decomposition in carboxylic acid reaction process under alkaline condition, how not influence
The bromo- tri- fluoro- 1- butylene of 1,1,2- of 4- is controlled in reaction decomposition under the premise of carrying out is the greatest problem of the project.
Invention content
To solve the above problems, the object of the present invention is to provide a kind of synthetic methods of the nematicide containing lactonic ring.
The present invention to achieve the above object, is achieved through the following technical solutions：
A kind of synthetic method of the nematicide containing lactonic ring, the nematicide containing lactonic ring are [2- (2- methoxyl groups
Phenyl) -5- oxo-tetrahydrofuran -3- bases]-formic acid [4- (1,1,2- tri- fluoro- 1- butylene) base] ester, synthetic method includes following
Step：
2- (2- methoxyphenyls) -5- oxo-tetrahydrofuran -3- carboxylic acids are dissolved in solvent, are stirred evenly, are added thereto
Enter organic alkali, then 4- bromo- 1,1,2- tri- fluoro- 1- fourths is added in salt-forming reaction 0.5~2 hour at 0~80 DEG C thereto
Alkene, substitution reaction 1~72 hour, obtains reaction solution at 40~110 DEG C, and hydrochloric acid is added into reaction solution, adjusts pH to 3~6,
Then the aqueous sodium carbonate that addition mass concentration is 10~15% thereto is 8~11 to pH, and organic phase is depressurized and steamed by liquid separation
Solvent is removed in distillation, obtains [2- (2- methoxyphenyls) -5- oxo-tetrahydrofuran -3- bases]-formic acid [4- (1,1,2- tri- fluoro- 1- fourths
Alkene) base] ester；
The organic alkali is alkali metal salt, metal alkyl lithiumation object, pyridine, tetramethylguanidine, triethylamine or the DBU of alcohol；
The solvent is toluene, benzene, dichloromethane or chloroform；
Wherein 2- (2- methoxyphenyls) -5- oxo-tetrahydrofuran -3- carboxylic acids, organic alkali, solvent and the bromo- 1,1,2- of 4-
The molal volume ratio of three fluoro- 1- butylene is 1.5~3mol：1~2mol：0.5~1L：1mol.
Preferred synthetic method, it is characterised in that：The organic alkali is DBU or tetramethylguanidine.
Preferred synthetic method, it is characterised in that：The temperature of salt-forming reaction is 30~50 DEG C, and the time is 1~2 hour.
Preferred synthetic method, it is characterised in that：The temperature of substitution reaction is 70~90 DEG C, and the time is 48~60 hours.
Preferred synthetic method, it is characterised in that：The solvent is chloroform.
Preferred synthetic method, it is characterised in that：The organic alkali is tetramethylguanidine.
Preferred synthetic method, it is characterised in that：Include the following steps：
2- (2- methoxyphenyls) -5- oxo-tetrahydrofuran -3- carboxylic acids are dissolved in chloroform, stirs evenly, is cooled to 10
~30 DEG C, organic alkali is added dropwise thereto, rate of addition is 1~5 drop/5 seconds, is added dropwise, and is warming up to 30~60 DEG C, reaction
0.5~2 hour, 4- bromo- 1 is added thereto, 1,2- tri- fluoro- 1- butylene is reacted 48~60 hours, reacted under reflux
Hydrochloric acid is added into reaction solution for liquid, adjusts pH to 3~4, and the aqueous sodium carbonate that mass concentration is 10% is then added thereto
It is 8~10 to pH, organic phase is evaporated under reduced pressure and removes solvent, obtains [2- (2- methoxyphenyls) -5- oxo tetrahydrochysene furans by liquid separation
Mutter -3- bases]-formic acid [4- (tri- fluoro- 1- butylene of 1,1,2-) base] ester；
Wherein 2- (2- methoxyphenyls) -5- oxo-tetrahydrofuran -3- carboxylic acids, organic alkali, solvent and the bromo- 1,1,2- of 4-
The molal volume ratio of three fluoro- 1- butylene is 1.5~2mol：1~1.5mol：0.5~1L：1mol；
The organic alkali is DBU or tetramethylguanidine.
Preferably, the organic alkali is tetramethylguanidine.
The reaction mechanism of the compound of the present invention is (by taking tetramethylguanidine as an example)：
The present invention total chemical equation be：
The present invention has the following advantages compared with prior art：
4- bromo- 1,1,2- tri- fluoro- 1- butylene must carry out under alkaline condition with reacting for carboxylic acid, in view of 4- bromo- 1,1,
There is decomposing phenomenon in tri- fluoro- 1- butylene of 2-, in order to control bromo- 1 4- under alkaline condition, the decomposition of 1,2- tri- fluoro- 1- butylene, conventional
Method be to be reacted using weak base, but reacted using this method, 4- bromo- 1,1,2- tri- fluoro- 1- butylene and carboxylic acid
Reaction be not thorough, and easy to produce impurity, cause product yield there was only 30~40%, and due to 4- bromo- 1,1,2- tri-
The cost of fluoro- 1- butylene costliness seriously limits [2- (2- methoxyphenyls) -5- oxo-tetrahydrofuran -3- bases]-formic acid [4-
(tri- fluoro- 1- butylene of 1,1,2-) base] ester production；The present invention first generates carboxylate using carboxylic acid and organic alkali, then carboxylic acid
Again with 4- bromo- 1,1,2- tri- fluoro- 1- butene reactions obtain target product, solve 4- bromo- 1,1,2- tri- fluoro- 1- butylene and carboxylic salt
The halfway defect of reaction of acid, while 4- bromo- 1 is reduced, the decomposition of 1,2- tri- fluoro- 1- butylene, the yield of product can reach
85% or more, when in particular by DBU or tetramethylguanidine, product yield can reach 90% or more；And this method post-processes work
Sequence is simple, is suitble to large-scale industrial production, greatly reduces production cost, accelerate the promotion and application of new product.
Specific implementation mode
The alkali metal salt of alcohol includes sodium methoxide, potassium ethoxide, potassium tert-butoxide or sodium tert-butoxide etc. in the present invention；Metal alkyl lithium
Compound includes n-BuLi, ethyl-lithium etc..
Below in conjunction with specific embodiment, the invention will be further described.
Embodiment 1
35.4kg2- (2- methoxyphenyls) -5- oxo-tetrahydrofuran -3- carboxylic acids are dissolved in 50L toluene, are stirred evenly,
5.4kg sodium methoxides are added thereto, then 18.9kg4- bromo- 1,1,2- is added in salt-forming reaction 0.5 hour at 0 DEG C thereto
Three fluoro- 1- butylene, substitution reaction 1 hour, obtains reaction solution at 40 DEG C, and hydrochloric acid is added into reaction solution, adjusts pH to 3, so
The aqueous sodium carbonate that addition mass concentration is 10% thereto afterwards is 8 to pH, and liquid separation removes organic phase vacuum distillation molten
Agent obtains 29.3kg [2- (2- methoxyphenyls) -5- oxo-tetrahydrofuran -3- bases]-formic acid [4- (1,1,2- tri- fluoro- 1- fourths
Alkene) base] ester, yield 85.2%.
Embodiment 2
70.86kg2- (2- methoxyphenyls) -5- oxo-tetrahydrofuran -3- carboxylic acids are dissolved in 100L benzene, are stirred evenly,
12.8kg n-BuLis are added thereto, then 18.9kg4- bromo- 1,1 is added in salt-forming reaction 2 hours at 80 DEG C thereto,
Tri- fluoro- 1- butylene of 2-, substitution reaction 72 hours, obtain reaction solution under reflux, and hydrochloric acid is added into reaction solution, adjust pH to 6,
Then the aqueous sodium carbonate that addition mass concentration is 15% thereto is 11 to pH, and organic phase is evaporated under reduced pressure and removes by liquid separation
Solvent obtains 30kg [2- (2- methoxyphenyls) -5- oxo-tetrahydrofuran -3- bases]-formic acid [4- (1,1,2- tri- fluoro- 1- fourths
Alkene) base] ester, yield 87.4%.
Embodiment 3
47.2kg 2- (2- methoxyphenyls) -5- oxo-tetrahydrofuran -3- carboxylic acids are dissolved in 60L dichloromethane, are stirred
Uniformly, 9.5kg pyridines are added thereto, then 18.9kg4- bromo- 1,1 is added in salt-forming reaction 1 hour at 20 DEG C thereto,
Tri- fluoro- 1- butylene of 2-, substitution reaction 10 hours, obtain reaction solution under reflux, and hydrochloric acid is added into reaction solution, adjust pH to 4,
Then the aqueous sodium carbonate that addition mass concentration is 12% thereto is 10 to pH, and organic phase is evaporated under reduced pressure and removes by liquid separation
Solvent obtains 29.8kg [2- (2- methoxyphenyls) -5- oxo-tetrahydrofuran -3- bases]-formic acid [4- (1,1,2- tri- fluoro- 1- fourths
Alkene) base] ester, yield 86.6%.
Embodiment 4
59kg 2- (2- methoxyphenyls) -5- oxo-tetrahydrofuran -3- carboxylic acids are dissolved in 80L chloroforms, are stirred evenly,
15.2kg triethylamines are added thereto, then 18.9kg4- bromo- 1,1 is added in salt-forming reaction 1.5 hours at 70 DEG C thereto,
Tri- fluoro- 1- butylene of 2-, substitution reaction 60 hours, obtain reaction solution under reflux, and hydrochloric acid is added into reaction solution, adjust pH to 5,
Then the aqueous sodium carbonate that addition mass concentration is 14% thereto is 9 to pH, and liquid separation removes organic phase vacuum distillation molten
Agent obtains 30.1kg [2- (2- methoxyphenyls) -5- oxo-tetrahydrofuran -3- bases]-formic acid [4- (1,1,2- tri- fluoro- 1- fourths
Alkene) base] ester, yield 87.5%.
Embodiment 5
42.5kg2- (2- methoxyphenyls) -5- oxo-tetrahydrofuran -3- carboxylic acids are dissolved in 70L dichloromethane, are stirred
Uniformly, 27.4kgDBU is added thereto, then 18.9kg4- bromo- 1 is added in salt-forming reaction 1.2 hours at 50 DEG C thereto,
1,2- tri- fluoro- 1- butylene, substitution reaction 50 hours, obtain reaction solution under reflux, are added hydrochloric acid into reaction solution, adjust pH to
4, the aqueous sodium carbonate that then addition mass concentration is 13% thereto to pH is 10, and liquid separation removes organic phase vacuum distillation
Solvent is removed, 31.1kg [2- (2- methoxyphenyls) -5- oxo-tetrahydrofuran -3- bases]-formic acid [4- (1,1,2- tri- fluoro- 1- are obtained
Butylene) base] ester, yield 90.5%.
Embodiment 6
52kg 2- (2- methoxyphenyls) -5- oxo-tetrahydrofuran -3- carboxylic acids are dissolved in 80L toluene, are stirred evenly,
18.4kg tetramethylguanidine is added thereto, then 18.9kg 4- bromo- 1 are added in salt-forming reaction 1.8 hours at 60 DEG C thereto,
1,2- tri- fluoro- 1- butylene, substitution reaction 30 hours, obtain reaction solution under reflux, are added hydrochloric acid into reaction solution, adjust pH to
5, the aqueous sodium carbonate that then addition mass concentration is 12% thereto is 9 to pH, and organic phase is evaporated under reduced pressure and removes by liquid separation
Solvent obtains 31.5kg [2- (2- methoxyphenyls) -5- oxo-tetrahydrofuran -3- bases]-formic acid [4- (1,1,2- tri- fluoro- 1- fourths
Alkene) base] ester, yield 91.8%.
Embodiment 7
54.3kg2- (2- methoxyphenyls) -5- oxo-tetrahydrofuran -3- carboxylic acids are dissolved in 70L chloroforms, are stirred evenly,
16.1kg tetramethylguanidine is added thereto, then 18.9kg4- bromo- 1,1 is added in salt-forming reaction 1 hour at 30 DEG C thereto,
Tri- fluoro- 1- butylene of 2-, substitution reaction 48 hours, obtain reaction solution under reflux, and hydrochloric acid is added into reaction solution, adjust pH to 4,
Then the aqueous sodium carbonate that addition mass concentration is 10% thereto is 11 to pH, and organic phase is evaporated under reduced pressure and removes by liquid separation
Solvent obtains 31.8kg [2- (2- methoxyphenyls) -5- oxo-tetrahydrofuran -3- bases]-formic acid [4- (1,1,2- tri- fluoro- 1- fourths
Alkene) base] ester, yield 92.4%.
Embodiment 8
35.4kg 2- (2- methoxyphenyls) -5- oxo-tetrahydrofuran -3- carboxylic acids are dissolved in 50L benzene, are stirred evenly,
15.2kgDBU is added thereto, then 18.9kg4- bromo- 1,1,2- tri- is added in salt-forming reaction 2 hours at 80 DEG C thereto
Fluoro- 1- butylene, substitution reaction 8 hours, obtain reaction solution under reflux, and hydrochloric acid is added into reaction solution, adjust pH to 3, then
The aqueous sodium carbonate that addition mass concentration is 15% thereto is 8 to pH, and organic phase is evaporated under reduced pressure and removes solvent by liquid separation,
Obtain 32kg [2- (2- methoxyphenyls) -5- oxo-tetrahydrofuran -3- bases]-formic acid [4- (tri- fluoro- 1- butylene of 1,1,2-) base]
Ester, yield 93.0%.
Embodiment 9
47.2kg2- (2- methoxyphenyls) -5- oxo-tetrahydrofuran -3- carboxylic acids are dissolved in solvent 100L chloroforms, are stirred
Uniformly, 30 DEG C are cooled to, 11.5kg tetramethylguanidine is added dropwise thereto, rate of addition is 1 drop/5 seconds, is added dropwise, back flow reaction
0.5 hour, 18.9kg4- bromo- 1 is added thereto, 1,2- tri- fluoro- 1- butylene reacts 60 hours, obtains reaction solution under reflux,
Hydrochloric acid is added into reaction solution, adjusts pH to 3, the aqueous sodium carbonate that then addition mass concentration is 10% thereto to pH is
8, organic phase is evaporated under reduced pressure and removes solvent, obtains 32.8kg [2- (2- methoxyphenyls) -5- oxo-tetrahydrofurans -3- by liquid separation
Base]-formic acid [4- (1,1,2- tri- fluoro- 1- butylene) base] ester, yield 95.6%.
Embodiment 10
35.4kg 2- (2- methoxyphenyls) -5- oxo-tetrahydrofuran -3- carboxylic acids are dissolved in 50L chloroforms, stirring is equal
It is even, 10 DEG C are cooled to, 17.2kg tetramethylguanidine is added dropwise thereto, rate of addition is 1~5 drop/5 seconds, is added dropwise, is warming up to 60
DEG C, it reacts 2 hours, bromo- 1,1,2- tri- fluoro- 1- butylene of 18.9kg 4- is added thereto, reacts 48 hours, obtains under reflux
Hydrochloric acid is added into reaction solution for reaction solution, adjusts pH to 4, and it is water-soluble that the sodium carbonate that mass concentration is 10% is then added thereto
Liquid is 10 to pH, and organic phase is evaporated under reduced pressure and removes solvent, obtains 33.3kg [2- (2- methoxyphenyls) -5- oxos four by liquid separation
Hydrogen furans -3- bases]-formic acid [4- (1,1,2- tri- fluoro- 1- butylene) base] ester, yield 96.8%.
Claims (8)
1. a kind of synthetic method of the nematicide containing lactonic ring, it is characterised in that：
The nematicide containing lactonic ring be [2- (2- methoxyphenyls) -5- oxo-tetrahydrofuran -3- bases]-formic acid [4- (1,
1,2- tri- fluoro- 1- butylene) base] ester, synthetic method includes the following steps：
2- (2- methoxyphenyls) -5- oxo-tetrahydrofuran -3- carboxylic acids are dissolved in solvent, are stirred evenly, be added has thereto
Machine highly basic, salt-forming reaction 0.5~2 hour at 0~80 DEG C, then thereto be added 4- bromo- 1,1,2- tri- fluoro- 1- butylene,
Substitution reaction 1~72 hour, obtains reaction solution at 40~110 DEG C, and hydrochloric acid is added into reaction solution, adjusts pH to 3~6, then
The aqueous sodium carbonate that addition mass concentration is 10~15% thereto is 8~11 to pH, and liquid separation removes organic phase vacuum distillation
Solvent is removed, [2- (2- methoxyphenyls) -5- oxo-tetrahydrofuran -3- bases]-formic acid [4- (1,1,2- tri- fluoro- 1- butylene) is obtained
Base] ester；
The organic alkali is alkali metal salt, metal alkyl lithiumation object, pyridine, tetramethylguanidine, triethylamine or the DBU of alcohol；It is described
Solvent is toluene, benzene, dichloromethane or chloroform；
Wherein 2- (2- methoxyphenyls) -5- oxo-tetrahydrofuran -3- carboxylic acids, organic alkali, solvent and the bromo- 1,1,2- of 4- tri-
The molal volume ratio of fluoro- 1- butylene is 1.5~3mol：1~2mol：0.5~1L：1mol.
2. a kind of synthetic method of nematicide containing lactonic ring according to claim 1, it is characterised in that：It is described organic
Highly basic is DBU or tetramethylguanidine.
3. a kind of synthetic method of nematicide containing lactonic ring according to claim 1, it is characterised in that：Salt-forming reaction
Temperature be 30~50 DEG C, the time be 1~2 hour.
4. a kind of synthetic method of nematicide containing lactonic ring according to claim 1, it is characterised in that：Substitution reaction
Temperature be 70~90 DEG C, the time be 48~60 hours.
5. a kind of synthetic method of nematicide containing lactonic ring according to claim 1, it is characterised in that：The solvent
For chloroform.
6. a kind of synthetic method of nematicide containing lactonic ring according to claim 1, it is characterised in that：It is described organic
Highly basic is tetramethylguanidine.
7. a kind of synthetic method of nematicide containing lactonic ring according to claim 1, it is characterised in that：Including following
Step：
2- (2- methoxyphenyls) -5- oxo-tetrahydrofuran -3- carboxylic acids are dissolved in chloroform, stirs evenly, is cooled to 10~30
DEG C, organic alkali is added dropwise thereto, rate of addition is 1~5 drop/5 seconds, is added dropwise, and is warming up to 30~60 DEG C, reaction 0.5~2
Hour, 4- bromo- 1 is added thereto, 1,2- tri- fluoro- 1- butylene reacts 48~60 hours, obtains reaction solution, under reflux to anti-
It answers and hydrochloric acid is added in liquid, adjust pH to 3~4, the aqueous sodium carbonate that then addition mass concentration is 10% thereto to pH is 8
~10, organic phase is evaporated under reduced pressure and removes solvent, obtains [2- (2- methoxyphenyls) -5- oxo-tetrahydrofurans -3- by liquid separation
Base]-formic acid [4- (tri- fluoro- 1- butylene of 1,1,2-) base] ester；
Wherein 2- (2- methoxyphenyls) -5- oxo-tetrahydrofuran -3- carboxylic acids, organic alkali, solvent and the bromo- 1,1,2- of 4- tri-
The molal volume ratio of fluoro- 1- butylene is 1.5~2mol：1~1.5mol：0.5~1L：1mol；
The organic alkali is DBU or tetramethylguanidine.
8. a kind of synthetic method of nematicide containing lactonic ring according to claim 7, it is characterised in that：It is described organic
Highly basic is tetramethylguanidine.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1200109A (en) * | 1995-08-25 | 1998-11-25 | 拜尔公司 | Fluorobutene acid amides |
| CN104693162A (en) * | 2015-03-26 | 2015-06-10 | 大连大学 | Method for synthesizing beta-ester group-gamma-butyrolactone |
| CN106554334A (en) * | 2015-09-30 | 2017-04-05 | 山东省联合农药工业有限公司 | A kind of nematicide containing lactonic ring and its production and use |
| CN106554335A (en) * | 2015-09-30 | 2017-04-05 | 山东省联合农药工业有限公司 | A kind of nematicide containing lactonic ring of transconfiguration and its production and use |
-
2018
- 2018-06-08 CN CN201810585415.8A patent/CN108484538B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1200109A (en) * | 1995-08-25 | 1998-11-25 | 拜尔公司 | Fluorobutene acid amides |
| CN104693162A (en) * | 2015-03-26 | 2015-06-10 | 大连大学 | Method for synthesizing beta-ester group-gamma-butyrolactone |
| CN106554334A (en) * | 2015-09-30 | 2017-04-05 | 山东省联合农药工业有限公司 | A kind of nematicide containing lactonic ring and its production and use |
| CN106554335A (en) * | 2015-09-30 | 2017-04-05 | 山东省联合农药工业有限公司 | A kind of nematicide containing lactonic ring of transconfiguration and its production and use |
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