CN105130969A - N-furfuryl amide insecticide - Google Patents
N-furfuryl amide insecticide Download PDFInfo
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- CN105130969A CN105130969A CN201510559332.8A CN201510559332A CN105130969A CN 105130969 A CN105130969 A CN 105130969A CN 201510559332 A CN201510559332 A CN 201510559332A CN 105130969 A CN105130969 A CN 105130969A
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- Prior art keywords
- furfuryl
- formula
- compound
- ethyl acetate
- insecticide
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- DDRPCXLAQZKBJP-UHFFFAOYSA-N furfurylamine Chemical compound NCC1=CC=CO1 DDRPCXLAQZKBJP-UHFFFAOYSA-N 0.000 title claims abstract description 11
- 239000002917 insecticide Substances 0.000 title abstract description 5
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 2
- 230000000749 insecticidal effect Effects 0.000 abstract description 6
- 230000002045 lasting effect Effects 0.000 abstract description 4
- 230000005540 biological transmission Effects 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- 238000006243 chemical reaction Methods 0.000 description 15
- 230000000694 effects Effects 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 241000426497 Chilo suppressalis Species 0.000 description 6
- 241000500437 Plutella xylostella Species 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 239000012065 filter cake Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 238000000967 suction filtration Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000000575 pesticide Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 230000002265 prevention Effects 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 3
- 238000007598 dipping method Methods 0.000 description 3
- OGTLYUDOIVBATN-UHFFFAOYSA-N 1-bromopyrazole Chemical class BrN1C=CC=N1 OGTLYUDOIVBATN-UHFFFAOYSA-N 0.000 description 2
- 241000255777 Lepidoptera Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- UTVVREMVDJTZAC-UHFFFAOYSA-N furan-2-amine Chemical compound NC1=CC=CO1 UTVVREMVDJTZAC-UHFFFAOYSA-N 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000008399 tap water Substances 0.000 description 2
- 235000020679 tap water Nutrition 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 0 *c(cc(cc1C(NCc2ccc[o]2)=O)Cl)c1NC(c1cc(Br)n[n]1-c1ncccc1Cl)=O Chemical compound *c(cc(cc1C(NCc2ccc[o]2)=O)Cl)c1NC(c1cc(Br)n[n]1-c1ncccc1Cl)=O 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- 102000002322 Egg Proteins Human genes 0.000 description 1
- 108010000912 Egg Proteins Proteins 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- FNELVJVBIYMIMC-UHFFFAOYSA-N Ethiprole Chemical compound N1=C(C#N)C(S(=O)CC)=C(N)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl FNELVJVBIYMIMC-UHFFFAOYSA-N 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 1
- 240000005373 Panax quinquefolius Species 0.000 description 1
- 235000003140 Panax quinquefolius Nutrition 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 235000019994 cava Nutrition 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- PSOVNZZNOMJUBI-UHFFFAOYSA-N chlorantraniliprole Chemical class CNC(=O)C1=CC(Cl)=CC(C)=C1NC(=O)C1=CC(Br)=NN1C1=NC=CC=C1Cl PSOVNZZNOMJUBI-UHFFFAOYSA-N 0.000 description 1
- -1 chloro-3-tolyl Chemical group 0.000 description 1
- 239000002872 contrast media Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- VYFOAVADNIHPTR-UHFFFAOYSA-N isatoic anhydride Chemical compound NC1=CC=CC=C1CO VYFOAVADNIHPTR-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 210000004681 ovum Anatomy 0.000 description 1
- QQVIHTHCMHWDBS-UHFFFAOYSA-N perisophthalic acid Natural products OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 102000042094 ryanodine receptor (TC 1.A.3.1) family Human genes 0.000 description 1
- 108091052345 ryanodine receptor (TC 1.A.3.1) family Proteins 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000011272 standard treatment Methods 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000005945 translocation Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- 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
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (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)
Abstract
The invention discloses an N-furfuryl amide insecticide. The structure of the N-furfuryl amide insecticide is shown in the general formula I specified in the specification, wherein R1 is Cl or CH3. The N-furfuryl amide insecticide of the general formula I has the excellent insecticidal activity, has the higher uptake and transmission function, improves the control efficiency, prolongs the lasting period and can be used for preventing and controlling agricultural or forest pests.
Description
Technical field the invention belongs to agricultural insecticide field, is specifically related to a kind of N-furfuryl amides sterilant.
The resistance problem of background technology harmful organism is the main contributor that it is difficult to administer, and development of new pesticide control is the important channel administering resistance.Rynaxypyr compounds (ryanodine receptor inhibitor class) is the efficient pesticides of the control lepidoptera pest developed in recent years.Patent CN101550130B discloses the amides of the N-cycloalkyl substituted as follows with insecticidal activity:
Though compound has similarity with the compounds of this invention on precursor structure disclosed in above-mentioned patent, in the prior art, N-furfuryl amides (formula I) of the present invention has no open.
Summary of the invention
The N-furfuryl amides sterilant that the object of the present invention is to provide a kind of novel structure, good combination property, cost accounting low, may be used for the control of agricultural or forestry primary pest.
Technical scheme of the present invention is as follows:
A kind of N-furfuryl amides, structure is such as formula shown in I:
In formula: R
1be selected from Cl or CH
3.
Formula I can be prepared by the following method, and in reaction formula, each group definition is the same.
Namely formula II and formula III compound back flow reaction in ethyl acetate obtain formula I, and the embodiment of the present invention is shown in formula II compound and the preparation of formula III compound.Table 1 lists structure and the physical properties of formula I.
The structure of table 1 formula I and physical properties
Advantage of the present invention and positively effect:
Borer pest (as striped rice borer etc.) is difficult to contact medicament after piercing plant materials, and conventional contact killing type medicament is invalid to it.Especially " ethiprole " because of toxicity problem disabled after, lack control borer pest efficient medicament.According to the requirement of modern agriculture to low public hazards, ultra-high efficiency, long holding effect medicament, the medicament preventing and treating this class pest must have stronger Uptake and translocation function, and this is the basis of improving prevention effect and extending the lasting period.The present inventor is studied by lot of experiments, the furyl with hydrophilic and oleophilic parents effect is introduced in pesticide molecules structure, unexpectedly significantly extend the lasting period (see table 3) of control striped rice borer, this is of great significance minimizing spraying times, reduction expenses for prevention and control, tool such as minimizing environmental pollution, time and labour saving etc.Meanwhile, the compounds of this invention is also significantly better than contrast known compound (KC) to the insecticidal activity of lepidoptera pest small cabbage moth.The compounds of this invention toxicity is low, dosage is little, meets the requirement of modern agriculture to low public hazards, ultra-high efficiency, long holding effect, has the potentiality of initiative commercialization sterilant.
When the compounds of this invention is for controlling insect pest purposes, can be used alone, also can use with other active substance combination, to improve the comprehensive function of product.
The present invention also comprises the insect-killing composition using compound of Formula I as active ingredient, also comprises acceptable carrier in agricultural or forestry in this insect-killing composition.
It is clearly understood that, in the scope of the claims in the present invention, can various conversion and change be carried out.
Embodiment
Following synthesis example, formulation examples and raw test-results of surveying can be used to further illustrate the present invention, but do not mean that restriction the present invention.
Synthesis example
The preparation of example 1, compound 1
(1) synthesis of 2-amino-N-furfuryl benzamide
16.3g (0.1mol) isatoic anhydride and 180mL water is added in 250mL reaction flask, instillation 14.55g (0.15mol) chaff amine (2-furylamine), normal-temperature reaction 12h, suction filtration, filter cake washs with tap water (10mL × 2), dry to obtain white solid 18.4g, yield 85%.
(2) synthesis of amino-3, the 5-bis-chloro-N-furfuryl benzamide of 2-
21.6g (0.1mol) 2-amino-N-furfuryl benzamide and 150g ethyl acetate is added in 250mL reaction flask, temperature control less than 15 DEG C drips SULPHURYL CHLORIDE 33.75g (0.25mol), drip complete temperature control 15 DEG C reaction 4 ~ 5h, thin-layer chromatography (TLC) detection disappears to raw material point, suction filtration, filter cake, with ethyl acetate (20mL × 2) washing, dries to obtain white solid 22.37g, yield 78.5%.
(3) synthesis of compound 1
2.85g (0.01mol) 2-amino-3 is added in 100mL reaction flask, 5-bis-chloro-N-furfuryl benzamide and 10mL ethyl acetate, the 6mL diluted ethyl acetate liquid of instillation 3.55g (0.011mol) 1-(3-chloropyridine-2-base) the bromo-1H-pyrazoles of-3--5-formyl chloride (preparation is with reference to WO2003/015519), be warming up to backflow, back flow reaction 3h, be down to room temperature suction filtration, filter cake washs with 2mL ethyl acetate, dry, weigh to obtain white solid 4.467g, yield 82.4%.
1hNMR (500MHz, DMSO-d
6), δ (ppm) data are as follows:
Compound 1:4.308-4.319 (d, 2H), 6.226-6.232 (d, 1H), 6.364-6.368 (d, 1H), 7.384 (s, 1H), 7.498-7.503 (d, 1H), 7.535 (s, 1H), 7.600-7.625 (q, 1H), 7.867-7.871 (d, 1H), 8.158-8.174 (d, 1H), 8.501-8.509 (t, 1H), 8.906-8.928 (t, 1H), 10.499 (s, 1H).
The preparation of example 2, compound 2
(1) the chloro-8-methyl isophthalic acid of 6--H-benzo [the d] [synthesis of 1,3] oxazine-2,4-diketone
The chloro-3-tolyl acid of 18.5g (0.1mol) 2-amino-5-and 100mL ethyl acetate is added in 100mL reaction flask, instillation 2g pyridine, temperature control less than 40 DEG C drips the ethyl acetate solution 50mL of 14.85g (0.05mol) solid phosgene, 40 DEG C of reaction 4h, suction filtration, filter cake washs with ethyl acetate 10mL × 2, dries to obtain white solid 19.92g, yield 94.2%.
(2) synthesis of the chloro-3-methyl of 2-amino-5--N-furfuryl benzamide
21.15g (0.1mol) 6-chloro-8-methyl isophthalic acid-H-benzo [d] [1 is added in 250mL reaction flask, 3] oxazines-2,4-diketone and 180mL water, instillation 14.55g (0.15mol) chaff amine (2-furylamine), normal-temperature reaction 12h, suction filtration, filter cake is with 10mL × 2 tap water, dry to obtain white solid 22.48g, yield 85%.
(3) synthesis of compound 2
2.64g (0.01mol) 2-amino-5-chloro-3-methyl-N-furfuryl benzamide and 10mL ethyl acetate is added in 100mL reaction flask, the 6mL diluted ethyl acetate liquid of instillation 3.55g (0.011mol) 1-(3-chloropyridine-2-base) the bromo-1H-pyrazoles of-3--5-formyl chloride, be warming up to backflow, back flow reaction 3h, be down to room temperature suction filtration, filter cake, with the washing of 2mL ethyl acetate, is dried, weigh to obtain white solid 4.47g, yield 81.5%.
1hNMR (500MHz, DMSO-d
6), δ (ppm) data are as follows:
Compound 2:2.162 (s, 3H), 4.319-4.330 (d, 2H), 6.221-6.227 (d, 1H), (6.358-6.362 d, 1H), 7.314 (s, 1H), 7.344-7.348 (d, 1H), (7.496-7.499 d, 1H), 7.530 (s, 1H), 7.592-7.623 (q, 1H), (8.161-8.178 d, 1H), 8.498-8.507 (d, 1H),, 8.818-8.840 (t, 1H), 10.253 (s, 1H).
Biological activity determination
Example 3 insecticidal activity assay
1. kill small cabbage moth determination of activity:
Adopt leaf dipping method.Adopt the leaf dipping method that international resistance Action Committee (IRAC) proposes.With the liquid to be measured prepared, with straight peen ophthalmology tweezers dipping cabbage leaves, time 3-5 second, get rid of remaining liquid, each 1, totally 3, each sample, is successively placed in treatment paper by sample flag sequence.After liquid is dry, put into the straight type pipe that the markd 10cm of tool is long, access 2 age diamondback moth larvae 30, build the mouth of pipe with gauze.Test process be placed in standard treatment chamber, 48h check result touches polypide to pull out pin, and motionless person is dead.Calculate mortality ratio.3 repetitions are done in test, average.Compound I and known compound KC kill the active parallel comparison of small cabbage moth, and test-results is in table 2.
Table 2 kills small cabbage moth determination of activity
Illustrated by table 2 result, the compounds of this invention is significantly higher than known compound KC to small cabbage moth insecticidal activity.
2. the water prevention chilo suppressalis test of pesticide effectiveness:
Select the field that paddy growth, soil moisture content, water and fertilizer condition are consistent, be divided into test site and blank district, each plot area 150m
2, do not establish repetition.Sample sand mill to be tested is ground to form the water suspending agent of 5% effective content, dilute 500 times of liquid, with workers and peasants-16 type knapsack hand sprayer in 1 generation striped rice borer ovum incubate the dispenser of Sheng phase, investigated killed strain number respectively at after medicine 10 days, 20 days, 30 days----withered sheath, withered heart strain number.Method adopts parallel method often to process investigation 20 point, looks into 100 caves altogether, and the record total strain number of investigation and killed strain number, calculate prevention effect.
Test-results is in table 3.
Striped rice borer test-results prevented and treated by table 3
As can be known from Table 3, no matter the compounds of this invention is insecticidal effect or lasting period are all significantly better than contrast agents KC to striped rice borer.
Claims (3)
1. a N-furfuryl amides, structure is such as formula shown in I:
In formula: R
1be selected from Cl or CH
3.
2. according to the purposes of a kind of N-furfuryl amides according to claim 1, it is characterized in that formula I is used as sterilant, control crop pests.
3. an insect-killing composition is active ingredient and acceptable carrier in agricultural or forestry containing compound of Formula I according to claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510559332.8A CN105130969A (en) | 2015-09-06 | 2015-09-06 | N-furfuryl amide insecticide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510559332.8A CN105130969A (en) | 2015-09-06 | 2015-09-06 | N-furfuryl amide insecticide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN105130969A true CN105130969A (en) | 2015-12-09 |
Family
ID=54716597
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510559332.8A Pending CN105130969A (en) | 2015-09-06 | 2015-09-06 | N-furfuryl amide insecticide |
Country Status (1)
| Country | Link |
|---|---|
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1541063A (en) * | 2001-08-13 | 2004-10-27 | ��Ļ���Ű˾ | Method for controlling particular insects by applying anthranilamide compounds |
| CN101298435A (en) * | 2007-04-30 | 2008-11-05 | 中国中化集团公司 | O-formammidotiazol-benzamide compounds and use thereof |
| CN101333213A (en) * | 2008-07-07 | 2008-12-31 | 中国中化集团公司 | 1-substituted pyridyl-pyrazol acid amide compounds and use thereof |
| CN101967139A (en) * | 2010-09-14 | 2011-02-09 | 中化蓝天集团有限公司 | Fluoro methoxylpyrazole-containing o-formylaminobenzamide compound, synthesis method and application thereof |
-
2015
- 2015-09-06 CN CN201510559332.8A patent/CN105130969A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1541063A (en) * | 2001-08-13 | 2004-10-27 | ��Ļ���Ű˾ | Method for controlling particular insects by applying anthranilamide compounds |
| CN101298435A (en) * | 2007-04-30 | 2008-11-05 | 中国中化集团公司 | O-formammidotiazol-benzamide compounds and use thereof |
| CN101333213A (en) * | 2008-07-07 | 2008-12-31 | 中国中化集团公司 | 1-substituted pyridyl-pyrazol acid amide compounds and use thereof |
| WO2010003350A1 (en) * | 2008-07-07 | 2010-01-14 | 中国中化集团公司 | 1-substituted pyridyl-pyrazolyl amide compounds and uses thereof |
| CN101967139A (en) * | 2010-09-14 | 2011-02-09 | 中化蓝天集团有限公司 | Fluoro methoxylpyrazole-containing o-formylaminobenzamide compound, synthesis method and application thereof |
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Application publication date: 20151209 |