CN109574956B - Thiadiazole amide compound and application thereof - Google Patents

Thiadiazole amide compound and application thereof Download PDF

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CN109574956B
CN109574956B CN201710908193.4A CN201710908193A CN109574956B CN 109574956 B CN109574956 B CN 109574956B CN 201710908193 A CN201710908193 A CN 201710908193A CN 109574956 B CN109574956 B CN 109574956B
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trifluoromethyl
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CN109574956A (en
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王刚
吕亮
张俊龙
张稳
宋玉泉
梁爽
陈霖
李斌
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Shenyang Sinochem Agrochemicals R&D Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/06—1,2,3-Thiadiazoles; Hydrogenated 1,2,3-thiadiazoles
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
    • 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
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

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Abstract

The invention belongs to the field of insecticides and acaricides, and relates to a thiadiazole carboxamide compound and application thereof. The thiadiazole carboxamide compound is shown as a general formula I:

Description

Thiadiazole amide compound and application thereof
Technical Field
The invention belongs to the field of insecticides and acaricides, and relates to a thiadiazole amide compound and application thereof.
Background
Since insecticidal and acaricidal agents are resistant to pests after a period of use, there is a continuing need for new and improved compounds and compositions having insecticidal and acaricidal activity.
It is known that certain thiadiazole amide compounds have bactericidal, insecticidal activity, e.g. CN1180297A discloses compound KC 1 (compound 214 in the patent) and its fungicidal activity; CN1810808A discloses a compound KC 2 (compound Cpd SZG-2 in the patent) and bactericidal activity thereof; CN106831646A discloses a compound KC 3 (patent)Compound 5) and pesticidal activity thereof; CN106831647A discloses a compound KC 4 (Compound 86 in the patent) and pesticidal activity thereof.
Figure BDA0001424335320000011
In the prior art, thiadiazole amide compounds with the structures shown as general formula I are not reported.
Disclosure of Invention
The invention aims to provide a thiadiazole amide compound and application thereof.
In order to achieve the purpose, the technical scheme of the invention is as follows:
a thiadiazole carboxamide compound, which is shown as a general formula I,
Figure BDA0001424335320000012
in the formula:
R 1 is selected from C 1 -C 6 A haloalkyl group;
R 2 、R 3 and R 4 Each independently selected from halogen, cyano, nitro, C 1 -C 6 Haloalkyl, C 1 -C 6 Haloalkoxy, aminosulfonyl, C 1 -C 6 Alkylsulfinyl radical, C 1 -C 6 Alkylsulfonyl radical, C 1 -C 6 Alkylsulfonamide group, phenyl group, or a group represented by 1 to 5R which may be the same or different 6 Substituted phenyl, 5-or 6-membered heterocycle comprising 1 to 3 identical or different radicals from the group consisting of oxygen, nitrogen or sulfur, substituted by 1 to 4 identical or different radicals R 6 A substituted 5-or 6-membered heterocyclic ring containing 1 to 3 identical or different atoms selected from the group consisting of an oxygen atom, a nitrogen atom or a sulfur atom;
R 5 is selected from C 1 -C 6 An alkyl group;
R 6 selected from halogen, nitro, cyano, C 1 -C 6 Alkyl radical, C 1 -C 6 Alkoxy radical, C 1 -C 6 Haloalkyl or C 1 -C 6 A haloalkoxy group.
Preferably, in formula I:
R 1 is selected from C 1 -C 3 A haloalkyl group;
R 2 、R 3 and R 4 Each independently selected from fluorine, chlorine, bromine, iodine, cyano, nitro, C 1 -C 3 Haloalkyl, C 1 -C 3 Haloalkoxy, aminosulfonyl, C 1 -C 3 Alkylsulfinyl radical, C 1 -C 3 Alkylsulfonyl radical, C 1 -C 3 Alkylsulfonamide group, phenyl group, or a group represented by 1 to 5R which may be the same or different 6 Substituted phenyl, 5-or 6-membered heterocycle comprising 1 to 3 identical or different radicals from the group consisting of oxygen, nitrogen or sulfur, substituted by 1 to 4 identical or different radicals R 6 A substituted 5-or 6-membered heterocyclic ring containing 1 to 3 identical or different atoms selected from the group consisting of an oxygen atom, a nitrogen atom or a sulfur atom;
R 5 is selected from C 1 -C 6 An alkyl group;
R 6 selected from fluorine, chlorine, bromine, iodine, nitro, cyano, C 1 -C 3 Alkyl radical, C 1 -C 3 Alkoxy radical, C 1 -C 3 Haloalkyl or C 1 -C 3 A haloalkoxy group.
Further preferred, in formula I:
R 1 selected from fluoromethyl, chloromethyl, difluoromethyl, trifluoromethyl, trichloromethyl, 1-fluoroethyl, 2-trifluoroethyl, pentafluoroethyl, heptafluoro-n-propyl or heptafluoro-isopropyl;
R 2 、R 3 and R 4 Each independently selected from fluorine, chlorine, bromine, iodine, cyano, nitro and C 1 -C 3 Haloalkyl or C 1 -C 3 A haloalkoxy group;
R 5 is selected from C 1 -C 4 An alkyl group.
Still further preferably, in formula I:
R 1 selected from the group consisting of fluoromethyl, chloromethyl, difluoromethyl,Trifluoromethyl, trichloromethyl, 1-fluoroethyl, 2-trifluoroethyl, pentafluoroethyl, heptafluoro-n-propyl or heptafluoro-isopropyl;
R 2 、R 3 and R 4 Each independently selected from fluorine, chlorine, bromine, iodine, cyano, nitro or C 1 -C 3 A haloalkyl group;
R 5 selected from methyl, ethyl or propyl.
More preferably, in formula I:
R 1 selected from fluoromethyl, difluoromethyl, trifluoromethyl or 1-fluoroethyl;
R 2 、R 3 and R 4 Each independently selected from chloro, bromo, iodo, trifluoromethyl, 2-trifluoroethyl, pentafluoroethyl, heptafluoro-n-propyl or heptafluoro-isopropyl;
R 5 selected from methyl, ethyl or n-propyl.
A process for the preparation of a compound of formula I, the reaction formula being:
Figure BDA0001424335320000021
in the formula:
an L leaving group; r 1 、R 2 、R 3 、R 4 And R 5 As defined above.
The application of the compound of the general formula I in preparing insecticides and acaricides in the agricultural field.
An insecticidal and acaricidal composition comprises an active component and an agriculturally acceptable carrier, wherein the active component is a compound shown as a general formula I, and the weight content of the active component is 1-99%.
A method of controlling pests and mites by applying to a pest or to a medium in need of control thereof an effective amount of said composition of from 10 grams per hectare to 1000 grams per hectare.
In the definitions of the compounds of the general formula I given above, the terms used are generally defined as follows:
alkyl means straight or branched chain forms such as methyl, ethyl, n-propyl, isopropyl, and the like. Haloalkyl refers to a group in which the alkyl group is substituted with one or more halogen atoms, such as chloroethyl, trifluoromethyl, difluoromethyl, heptafluoroisopropyl, and the like. Alkoxy means a group having an oxygen atom attached to the terminal of an alkyl group, such as methoxy, ethoxy, n-propoxy, isopropoxy, and the like. Halogen means fluorine, chlorine, bromine, iodine.
The invention is characterized in that the invention also comprises a preparation method of the compound in the general formula I, and all groups in the reaction formula are defined as before except for other indications.
Figure BDA0001424335320000031
The compound of the general formula II and the compound of the general formula III react in a proper solvent at the temperature of-10 ℃ to the boiling point of the proper solvent for 0.5 to 48 hours to prepare the target compound IV.
Suitable solvents are selected from dichloromethane, chloroform, carbon tetrachloride, hexane, benzene, toluene, ethyl acetate, acetonitrile, tetrahydrofuran, dioxane, N-dimethylformamide or dimethylsulfoxide, and the like.
The reaction is advantageously carried out by adding a suitable base, which includes hydrogen compounds of alkali metals such as lithium, sodium or potassium, such as sodium hydride, hydroxides of alkali metals such as lithium, sodium or potassium, such as sodium hydroxide, carbonates of alkali metals such as sodium carbonate, and organic bases such as triethylamine, sodium tert-butoxide, etc.
The compounds of formula II can be prepared with reference to the following references: bioorganic & Medicinal chemistry letters,2007,17 (24): 6836-6840; journal of Agricultural and Food Chemistry,2009,57 (10): 4279-4286.
The compounds of formula III are commercially available or may be prepared by reference to the following references: WO2006134468A, journal of Organic Chemistry,2013,78 (10): 5103-5109; synthesis,2009, 8.
Figure BDA0001424335320000032
The compound of the general formula IV and the compound of the general formula V react in a proper solvent at the temperature of-10 ℃ to the boiling point of the proper solvent for 0.5-48 hours to prepare the target compound I.
Suitable solvents are selected from dichloromethane, chloroform, carbon tetrachloride, hexane, benzene, toluene, ethyl acetate, acetonitrile, tetrahydrofuran, dioxane, N-dimethylformamide or dimethyl sulfoxide, and the like.
The reaction is advantageously carried out by adding a suitable base, which includes hydrogen compounds of alkali metals such as lithium, sodium or potassium, such as sodium hydride, hydroxides of alkali metals such as lithium, sodium or potassium, such as sodium hydroxide, carbonates of alkali metals such as sodium carbonate, and organic bases such as triethylamine, sodium tert-butoxide, etc.
The structures and physical properties of the compounds of formula I are shown in Table 1.
Figure BDA0001424335320000033
Table 1 structural and physical properties of some compounds of formula I
Figure BDA0001424335320000034
/>
Figure BDA0001424335320000041
/>
Figure BDA0001424335320000051
/>
Figure BDA0001424335320000061
/>
Figure BDA0001424335320000071
Of partial compounds 1 H NMR(300MHz,CDCl 3 ) The data are as follows:
compound 2:9.05 (br s, 1H), 9.00 (s, 1H), 7.83 (s, 1H), 7.54 (t, 1H).
Compound 4:8.72 (s, 1H), 8.67 (s, 1H), 7.80 (s, 1H), 7.54 (t, 1H).
Compound 6:8.93 (s, 1H), 8.86 (s, 1H), 7.94 (s, 1H), 7.51 (t, 1H).
Compound 23:7.90 (s, 1H), 7.50 (s, 1H), 7.30 (t, 1H), 4.27-4.31 (m, 1H), 3.39-3.46 (m, 1H), 1.66-1.77 (m, 2H), 1.02 (s, 1H).
Compound 51:8.99 (s, 1H), 8.58 (br s, 1H), 7.86 (s, 1H), 7.51 (t, 1H).
The invention also comprises insecticidal and acaricidal compositions which comprise the compounds of formula I as active ingredients. The weight percentage of the compound of the general formula I as an active component in the insecticidal and acaricidal composition is between 1 and 99 percent. The insecticidal and acaricidal composition also comprises an agriculturally acceptable carrier.
The compositions of the present invention may be administered in the form of a formulation. The compounds of formula I are dissolved or dispersed as active ingredients in carriers or formulated so as to be more easily dispersed for use as insecticides, acaricides. For example: these chemicals can be formulated as wettable powders or emulsifiable concentrates. In these compositions, at least one liquid or solid carrier is added, and when necessary, a suitable surfactant may be added.
The technical scheme of the invention also comprises a method for preventing and controlling pests and mites, which comprises the following steps: the insecticidal and acaricidal composition of the invention is applied to the pests or to the growth medium thereof. An effective amount of from 10 grams per hectare to 1000 grams per hectare is generally preferred.
Compared with the known thiadiazole carboxamide compounds, the thiadiazole carboxamide compounds provided by the invention have unexpectedly high insecticidal and acaricidal activities. Therefore, the invention also comprises the application of the compound in the general formula I in controlling pests and mites.
For certain applications, for example in agriculture, one or more further fungicides, insecticides, herbicides, plant growth regulators or fertilizers and the like can be added to the insecticidal, acaricidal compositions according to the invention, whereby additional advantages and effects can be achieved.
It should be understood that various changes and modifications may be made within the scope of the present invention as defined by the claims.
Detailed Description
The following synthetic examples, biological activity assay examples, are intended to further illustrate the invention, but are not intended to limit the invention.
Synthetic examples
Example 1 preparation of compound 2:
Figure BDA0001424335320000072
2-chloro-3, 5-bis (trifluoromethyl) aniline (260 mg, 0.99 mmol), triethylamine (120 mg, 1.18 mmol) and 10ml of acetonitrile were charged in a reaction flask, and 10ml of an acetonitrile solution of 4-difluoromethyl-1, 2, 3-thiadiazole-5-carbonyl chloride (270 mg, 1.38 mmol) was added dropwise with stirring at room temperature. After the dripping is finished, the reaction is carried out at room temperature, and the reaction is finished after 3 hours. The reaction mixture was poured into 30 ml of water, and the organic layer was washed with a saturated aqueous sodium bicarbonate solution and a saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (eluent: ethyl acetate: petroleum ether =1 = 10) to obtain 170 mg of compound 2 in 40.1% yield.
Example 2 preparation of compound 23:
Figure BDA0001424335320000081
2-chloro-3, 5-bis (trifluoromethyl) aniline (450 mg, 1.707 mmol), potassium tert-butoxide (192 mg, 1.707 mmol) were added to a 100mL reaction flask, the solution turned from colorless to yellow, 1-iodopropane (290 mg, 1.707 mmol) was added dropwise after 5 minutes, and the progress of the reaction was checked by TLC. After 2hr, the reaction mixture was poured into 30 ml of water, and the organic layer was washed with a saturated aqueous sodium bicarbonate solution and a saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography to give 440 mg of 2-chloro-N-propyl-3, 5-bis (trifluoromethyl) aniline.
Figure BDA0001424335320000082
2-chloro-N-propyl-3, 5-bis (trifluoromethyl) aniline (290 mg, 0.949 mmol), triethylamine (115 mg, 1.139 mmol) and 10mL1, 2-dichloroethane were charged into a reaction flask, stirred at room temperature for 15min, followed by dropwise addition of a solution of 4-difluoromethyl-1, 2, 3-triazole-5-carbonyl chloride (330 mg, 1.665 mmol) in 1, 2-dichloroethane, heating under reflux after completion of the dropwise addition, and the progress of the reaction was monitored by TLC. After the reaction was completed, the solvent was evaporated under reduced pressure, and the mixture was extracted with ethyl acetate and water, and the organic layer was taken out, washed with saturated sodium bicarbonate and saturated sodium chloride, and subjected to column chromatography (PE: EA =100, 1,25: 49.1 percent.
Example 3 preparation of compound 149:
Figure BDA0001424335320000083
to a reaction flask were added 2-chloro-3, 5-bis (trifluoromethyl) aniline (374 mg, 1.42 mmol), triethylamine (172 mg, 3.25 mmol) and 10ml of acetonitrile, and 10ml of an acetonitrile solution of 4- (1-fluoroethyl) -1,2, 3-thiadiazole-5-carbonyl chloride (276 mg, 1.42 mmol) was added dropwise with stirring at room temperature. After the dripping is finished, the reaction is carried out at room temperature, and the reaction is finished after 2 hours. The reaction mixture was poured into 30 ml of water, extracted with 50 ml of ethyl acetate, and the organic layer was washed successively with a saturated aqueous sodium hydrogencarbonate solution and a saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (eluent: ethyl acetate: petroleum ether =1, 25) to give 150 mg of compound 149 in 23.3% yield.
Examples of measurement of biological Activity
The activity assays were further carried out with typical compounds of the invention of formula I:
according to the solubility of the compound to be detected, the compound in the general formula I is dissolved in acetone or dimethyl sulfoxide, then 50 ml of solution to be detected with the required concentration is prepared by 1 per thousand of Tween 80 solution, and the content of the acetone or the dimethyl sulfoxide in the solution is not more than 10%.
EXAMPLE 4 determination of insecticidal Activity
4.1 assay of Plutella xylostella-killing Activity
The cabbage leaves were punched out into a leaf dish having a diameter of 2 cm by a punch, and sprayed with Airbrush under a pressure of 10psi (approximately 0.7 kg/cm) 2 ) Spraying on the front and back surfaces of each leaf disk, wherein the liquid spraying amount is 0.5mL. After drying in the shade, 10 test insects of 2 years old are inoculated into each treatment, and each treatment is repeated for 3 times. After treatment, the mixture is placed into an observation room with the temperature of 25 ℃ and the relative humidity of 60-70% for culture, the number of the survival insects is investigated after 72 hours, and the death rate is calculated.
Compounds 2,3, 23 and 149 of the present invention were selected according to the above test methods. 149 and known Compound KC 1 And KC 2 Parallel determination of insecticidal activity of diamondback moth is carried out (the control compounds are all self-made, and the structure is confirmed by nuclear magnetic resonance hydrogen spectrum), and the test results are shown in table 2.
Table 2: comparison of insecticidal Activity of some of the Compounds of the present invention against Plutella xylostella with known Compounds
Figure BDA0001424335320000091
Note: "-" indicates no testing was performed
4.2 measurement of armyworm-killing Activity
The corn leaves were cut into 2 cm long sections and sprayed with Airbrush at a pressure of 10psi (approximately 0.7 kg/cm) 2 ) Spraying on the front and back sides of each leaf section, wherein the liquid spraying amount is 0.5mL. After drying in the shade, 10 test insects of 2 years old are inoculated in each treatment, and the treatment is repeated for 3 times. After treatment, the mixture is placed into an observation room with the temperature of 25 ℃ and the relative humidity of 60-70% for culture, the number of the survival insects is investigated after 72 hours, and the death rate is calculated.
According to the above test methods, the compounds 22, 3, 51 and 149 of the present invention and the known compound KC were selected 1 And KC 2 Parallel determination of the insecticidal activity of armyworm (the control compounds are all self-made, and the structures are confirmed by nuclear magnetic resonance hydrogen spectrum) is carried out, and the test results are shown in Table 3。
Table 3: comparison of insecticidal Activity of some of the Compounds of the invention with known Compounds against armyworm
Figure BDA0001424335320000092
4.3 determination of Myzus persicae-killing Activity
A culture dish with the diameter of 6 cm is taken, a layer of filter paper is covered on the bottom of the culture dish, and a proper amount of tap water is dripped for moisturizing. Cutting cabbage leaf with proper size (diameter about 3 cm) and 15-30 heads of aphids from cabbage plant for culturing Myzus persicae, removing winged aphids and aphids on the front of leaf, investigating radix, placing leaf back upwards in culture dish, and spraying with hand-held Airbrush sprayer under pressure of 10psi (about 0.7 kg/cm) 2 ) The amount of sprayed liquid was 0.5mL, and the treatment was repeated 3 times, and the treated product was placed in a standard observation room, and after 48 hours, the number of surviving insects was investigated and the mortality was calculated.
According to the above test method, the compound 2 of the present invention and the known compound KC are selected 1 And KC 2 Parallel determination of insecticidal activity of myzus persicae was performed, and the test results are shown in table 4.
Table 4: comparison of insecticidal Activity of some of the Compounds of the present invention against Myzus persicae with known Compounds
Figure BDA0001424335320000101
4.4 measurement of Tetranychus cinnabarinus adult mite Activity
The measuring method comprises the following steps: collecting two bean seedlings of true leaf vegetable, inoculating tetranychus cinnabarinus, examining basic number, and spraying with Airbrush sprayer under 10psi (about 0.7 kg/cm) 2 ) The amount of sprayed liquid was 0.5mL. After 3 times of treatment, the treated mites were placed in a standard observation room, and the number of live mites was checked after 72 hours to calculate the mortality rate.
According to the above test method, the compounds 2 and 51 of the present invention and the known compound KC are selected 1 And KC 2 Carrying out parallel determination on insecticidal activity of tetranychus cinnabarinus and obtaining test resultsSee table 5.
Table 5: comparison of insecticidal Activity of some of the Compounds of the present invention against Tetranychus cinnabarinus with known Compounds
Figure BDA0001424335320000102
/>

Claims (8)

1. A thiadiazole amide compound is characterized in that: the compound is shown as the general formula I
Figure QLYQS_1
In the formula:
R 1 selected from difluoromethyl;
R 2 selecting chlorine;
R 3 is selected from trifluoromethyl;
R 4 is selected from trifluoromethyl;
R 5 is selected from C 1 -C 6 An alkyl group.
2. A compound according to claim 1, wherein in formula I:
R 1 selected from difluoromethyl;
R 2 selecting chlorine;
R 3 is selected from trifluoromethyl;
R 4 is selected from trifluoromethyl;
R 5 selected from methyl, ethyl or propyl.
3. A compound according to claim 2, wherein in formula I:
R 1 selected from difluoromethyl;
R 2 selecting chlorine;
R 3 is selected from trifluoromethyl;
R 4 is selected from trifluoromethyl;
R 5 selected from methyl, ethyl or n-propyl.
4. A thiadiazole amide compound is characterized in that: the compound is represented by the following formula:
Figure QLYQS_2
、/>
Figure QLYQS_3
、/>
Figure QLYQS_4
。
5. a process for the preparation of a compound of formula I according to claim 1, characterized in that: the reaction formula is as follows:
Figure QLYQS_5
in the formula: l is a leaving group; r is 1 、R 2 、R 3 、R 4 And R 5 As defined above.
6. The use of a compound of the general formula I according to claim 1 for the preparation of a pesticide in the agricultural field.
7. An insecticidal composition characterized by: an active ingredient of the insecticidal composition and an agriculturally acceptable carrier, wherein the active ingredient is a compound shown as a general formula I in claim 1, and the weight content of the active ingredient is 1-99%.
8. A method of controlling pests, comprising: a composition as claimed in claim 7 applied to a medium in which control of pests or their growth is desired at an effective dose of from 10 to 1000 grams per hectare.
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WO1999052882A1 (en) * 1998-04-13 1999-10-21 Nihon Nohyaku Co., Ltd. 1,2,3-thiadiazole derivative or salt thereof and pest control agent, and method of use thereof
CN106831647A (en) * 2015-12-04 2017-06-13 沈阳中化农药化工研发有限公司 A kind of thiadiazoles amides compound and application thereof

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Publication number Priority date Publication date Assignee Title
WO1999052882A1 (en) * 1998-04-13 1999-10-21 Nihon Nohyaku Co., Ltd. 1,2,3-thiadiazole derivative or salt thereof and pest control agent, and method of use thereof
CN106831647A (en) * 2015-12-04 2017-06-13 沈阳中化农药化工研发有限公司 A kind of thiadiazoles amides compound and application thereof

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