CN102285965B - N-(cyanoalkyl) benzamide compound and application thereof - Google Patents
N-(cyanoalkyl) benzamide compound and application thereof Download PDFInfo
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- CN102285965B CN102285965B CN201010212402XA CN201010212402A CN102285965B CN 102285965 B CN102285965 B CN 102285965B CN 201010212402X A CN201010212402X A CN 201010212402XA CN 201010212402 A CN201010212402 A CN 201010212402A CN 102285965 B CN102285965 B CN 102285965B
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- YKVDRDBULIJMSY-UHFFFAOYSA-N CC(C)(C#N)NC(c(cc(cc1Cl)C#N)c1N)=O Chemical compound CC(C)(C#N)NC(c(cc(cc1Cl)C#N)c1N)=O YKVDRDBULIJMSY-UHFFFAOYSA-N 0.000 description 1
- KCMMKWRPPVXDTH-UHFFFAOYSA-N Nc(c(C(O)=O)cc(C#N)c1)c1Cl Chemical compound Nc(c(C(O)=O)cc(C#N)c1)c1Cl KCMMKWRPPVXDTH-UHFFFAOYSA-N 0.000 description 1
Abstract
The invention discloses an N-(cyanoalkyl) benzamide compound with a novel structure, and as shown in a general formula I: each substituent group in the formula is defined in a specification. The compound shown in the general formula I has excellent insecticidal activity and can be used for preventing and curing insect pests.
Description
Technical field
The invention belongs to the agricultural insecticide field, relate to a kind of N-(cyano group alkyl) benzamide compound and application thereof.
Background technology
Due to sterilant in use for some time, insect can produce resistance to it, therefore, need constantly invention novel with compound and composition improved tool insecticidal activity.Simultaneously, along with people, to the growing needs such as agricultural and animal products with to the pay attention to day by day of environment protection, also need lower, the environment amenable new sterilant of use cost always.
WO2008134969A has reported a kind of N-(cyano group alkyl) benzamide compound, and wherein compound 1.23 (structural formula is as follows) has the biting mouth parts of killing insect activity, and beet armyworm is had to high prevention effect.
The compound that has contained the chlorine atom on the phenyl ring although disclose simultaneously in the list of above-mentioned patent application specification (compound 1.12 and 1.22 in table 1), not actual making.In the prior art, preparation and the insecticidal activity thereof as N-shown in the present (cyano group alkyl) benzamide compound has no open.
Summary of the invention
The object of the present invention is to provide a kind of N-(cyano group alkyl) benzamide compound of novel structure, it can be applicable to the control of insect pest on agricultural, forestry or health.
Technical scheme of the present invention is as follows:
A kind of N-(cyano group alkyl) benzamide compound, as shown in general formula I:
In formula:
R
1Be selected from H or C
1-C
6Alkyl;
R
2Be selected from H or C
1-C
6Alkyl;
R
3Be selected from C
1-C
6Alkyl or C
3-C
6Cycloalkyl, the hydrogen on described group can also further be replaced by following group: halogen, C
1-C
3Alkoxyl group or phenoxy group;
Perhaps R
2And R
3With the carbon connected, form together C
3-C
6Cycloalkyl;
R
4Be selected from halogen;
R
5Be selected from halogen, C
1-C
6Alkyl, C
1-C
6Haloalkyl, C
1-C
6Halogenated alkoxy, C
2-C
6Cyanogen is for alkoxyl group, C
3-C
6Alkene oxygen base or C
3-C
6Alkynyloxy group;
R
6Be selected from H, CN, halogen, C
1-C
6Alkyl or C
1-C
6Haloalkyl;
The further preferred compound of the present invention is, in general formula I:
R
1Be selected from H;
R
2Be selected from H or C
1-C
6Alkyl;
R
3Be selected from C
1-C
6Alkyl;
Perhaps R
2And R
3With the carbon connected, form together C
3-C
6Cycloalkyl;
R
4Be selected from F, Cl, Br or I;
R
5Be selected from halogen, C
1-C
6Alkyl, C
1-C
6Haloalkyl, C
1-C
6Halogenated alkoxy, C
2-C
6Cyanogen is for alkoxyl group, C
3-C
6Alkene oxygen base or C
3-C
6Alkynyloxy group;
R
6Be selected from H, halogen or C
1-C
6Haloalkyl;
The present invention further preferred compound is, in general formula I:
R
1Be selected from H;
R
2Be selected from H or C
1-C
3Alkyl;
R
3Be selected from C
1-C
3Alkyl;
R
4Be selected from Cl or Br;
R
5Be selected from Cl, Br or CF
3
R
6Be selected from H or Cl.
In the definition of the compound of Formula I that the above provides, collect term General Definition used as follows:
Alkyl refers to the straight or branched form, such as methyl, ethyl, n-propyl, sec.-propyl etc.Cycloalkyl comprises cyclopropyl, cyclobutyl, cyclopropyl methyl, methyl cyclopropyl etc.Haloalkyl refers to the group that alkyl is replaced by one or more halogen atoms, as chloroethyl, trifluoromethyl etc.Alkoxyl group refers to that the alkyl end is connected with the group of Sauerstoffatom, such as methoxyl group, oxyethyl group, positive propoxy, isopropoxy etc.Phenoxy group refers on phenyl ring be connected with the group of Sauerstoffatom.Halogenated alkoxy refers to that alkyl is replaced by one or more halogen atoms, and end is connected with the group of Sauerstoffatom.Cyanogen refers to that for alkoxyl group alkyl is replaced by one or more cyano group, and end is connected with the group of Sauerstoffatom.Alkene oxygen base refers to that the thiazolinyl end is connected with the group of Sauerstoffatom.Alkynyloxy group refers to that the alkynyl end is connected with the group of Sauerstoffatom.Halogen refers to fluorine, chlorine, bromine, iodine.
Research is found, is worked as R
4While being selected from halogen, be difficult to obtain target compound according to the preparation method who provides in WO 2008134969A.Through a large amount of exploration, the unexpected discovery adds strong inorganic base for example during sodium hydride in condensation reaction one step, can successfully obtain the compounds of this invention, thereby complete the present invention.
Compound of Formula I of the present invention can be by following method preparation, and in reaction formula, each group definition is the same.
General formula I I compound in suitable solvent, temperature is-10 ℃ and at first with sodium hydride, reacts 0.5-2 hour under reflux temperature, then with compound of formula III, for-10 ℃, 0.5-48 hour makes compound of Formula I to reacting under reflux temperature in temperature.Suitable solvent is selected from hexane, benzene, toluene, ethyl acetate, acetonitrile, THF, dioxane, DMF or dimethyl sulfoxide (DMSO) etc.
The preparation method of general formula I I compound is as follows:
General formula I I compound can (have commercially available with general formula V compound by general formula I V compound in suitable solvent, also can make by oneself, the preparation method is referring to J.Peptide Res.56,2000,283-297) in temperature, made in 0.5-48 hour to reaction under reflux temperature for-10 ℃.Suitable solvent is selected from chloroform, methylene dichloride, tetracol phenixin, hexane, benzene, toluene, ethyl acetate, DMF, THF or dioxane etc.Add alkaloids, as triethylamine, pyridine, sodium hydroxide, potassium hydroxide, sodium carbonate, salt of wormwood or sodium bicarbonate etc. to reacting favourable.
General formula I I compound (R
4For halogen) also can be by general formula I I compound (R
4For H) in suitable solvent, for-10 ℃, made in 0.5-48 hour to reacting under reflux temperature in temperature with halide reagent.Solvent can be selected from chloroform, methylene dichloride, tetracol phenixin, hexane, benzene, toluene, ethyl acetate, DMF, THF or dioxane etc., and halide reagent can be selected from chlorine, bromine, N-chlorosuccinimide, N-bromo-succinimide or N-iodine chlorosuccinimide etc.
The preparation of general formula I V compound can be referring to Bioorganic & Medicinal Chemistry, (2003), 11,1769-1780, Bioorganic & Medicinal Chemistry Letters, 2005,15,4898-4906, Tetrahedron Letters, 1991,32,3263-3264.
The preparation of compound of formula III (pyrazol formyl chloride and corresponding raw material carboxylic acid thereof) can be with reference to Bioorganic & Medicinal Chemistry Letters, the operation in 2005,15,4898-4906, WO2008/134969A1, WO03/015519A1, WO2008/072745A1 and WO 2009/010260A2 is carried out.
Table 1 has been listed structure and the physical properties of part compound of Formula I.
Table 1
Have now found that, compare with known alkyl-benzamide compound, the halogen-benzamide compound shown in general formula I of the present invention has beyond thought height and kills the sucking insect activity.Therefore, the present invention also comprise compound of Formula I as agricultural insecticide be used to controlling the purposes of insect pest.
The present invention also comprises usings the insect-killing composition of compound of Formula I as active ingredient.In this insect-killing composition, the weight percentage of active ingredient is between 1-99%.In this insect-killing composition, also comprise acceptable carrier on agricultural, forestry, health.
Composition of the present invention can preparation form use.Compound of Formula I is as solubilization of active ingredient or be scattered in carrier or be mixed with preparation and disperse in order to be easier to while as sterilant, using.For example: these chemicals can be made into wettable powder or missible oil.In these compositions, add at least a kind of liquid or solid carrier, and can add suitable tensio-active agent when needed.
Technical scheme of the present invention also comprises the method for pest control: insect-killing composition of the present invention is imposed on described insect or its growth medium.Usually the comparatively suitable significant quantity of selecting be per hectare 10 grams to 1000 grams, preferably significant quantity is that per hectare 20 grams are to 500 grams.
For some application, such as on agricultural, can in insect-killing composition of the present invention, adding one or more other sterilant, Insecticides (tech) & Herbicides (tech), plant-growth regulator or fertilizer etc., can produce additional advantage and effect thus.
Should be clear and definite be, in claim limited range of the present invention, can carry out various conversion and change.
Embodiment
Following synthetic example, living test are tested result and be can be used to further illustrate the present invention, but do not mean that restriction the present invention.
Synthetic example
The preparation of example 1, compound 4
(1), 2-amino-2-methyl propionitrile is synthetic
In the reaction flask of 250 milliliters, add sodium cyanide (4.95 grams, 100 mmoles) and ammoniacal liquor (60 milliliters), stirring at normal temperature to sodium cyanide dissolves fully, adds acetone (5.84 grams, 100 mmoles) and ammonium chloride (5.38 grams, 100 mmoles), normal-temperature reaction 48 hours, reaction solution dichloromethane extraction (3X50 milliliter), merge organic phase, with anhydrous magnesium sulfate drying, decompression precipitation, obtain 5.25 gram water white oils, yield: 57%.
1H?NMR(300MHz，CDCl
3)：1.84(br?s，2H)，1.50(s，6H)。
(2), 2-amino-5-iodo-benzoic acid is synthetic
In 500 milliliters of there-necked flasks, add successively 2-benzaminic acid (30.2 grams, 220 mmoles), DMF (300 milliliters), after stirring at room to raw material dissolves fully, add the N-N-iodosuccinimide (to be called for short: NIS) (49.5 grams in batches, 220 mmoles), room temperature reaction approximately 10 hours afterreactions is complete, slowly pour reaction solution in appropriate trash ice vigorous stirring, there is solid to separate out, filter, filter cake washs 2 times with tap water, and natural air drying obtains 55.0 gram gray solid, yield: 95%, fusing point: 232-234 ℃.
(3), the 2-amino-5-cyano is benzoic synthetic
In 1000 milliliters of there-necked flasks, add successively 2-amino-5-iodo-benzoic acid (41.5 grams, 158 mmoles), DMF (400 milliliters), after being stirred to raw material and dissolving fully, add cuprous cyanide (18.4 grams, 205 mmoles), slowly be warming up to 140-145 ℃, TLC monitoring reaction process, rear cooling reacted completely in 20 hours, question response liquid is down to 30-40 ℃, under vigorous stirring, add sodium hydroxide (6.32 grams, 158 mmoles) aqueous solution (300 milliliters), the reaction solution pH value is adjusted to 8-9, there is green solid to separate out filtration, filtrate is acidified to PH=5-6 with 36% concentrated hydrochloric acid again, separate out a large amount of solids, filter, filter cake washs 2 times with tap water, natural air drying obtains 19.2 gram gray solid, yield: 75%, fusing point: 255-257 ℃.
IR(KBr，cm-1)：3450(s，NH)，3350(s，NH)，2220(s，CN)，1670(s，-CO-)。
(4) the chloro-5-cyanobenzoic acid of 2-amino-3-is synthetic
In the reaction flask of 250 milliliters, add successively 2-amino-5-cyano phenylformic acid (10.0 grams, 61.7 mmole), 100 milliliters of dimethyl formamides, add the N-chlorosuccinimide (to be called for short: NCS) (8.2 grams in batches, 61.7 mmole), be warming up under 100-110 ℃ and stirred 30 minutes.Be cooled to room temperature, by reaction solution impouring 200 ml waters, filtration, dry 11.5 gram brown solids, the yield 95% of obtaining.
(5), the chloro-5-cyano group-N-of 2-amino-3-(2-cyano group-2-propyl group) benzamide is synthetic
In 100 milliliters of reaction flasks, add the chloro-5-cyanobenzoic acid of 2-amino-3-(5.0 grams, 25.4 mmoles), sulfur oxychloride (10.6 grams, 89.0 mmoles), mixture reflux 3 hours, solvent is to the greatest extent steamed in decompression, obtains sorrel oily matter.Upwards walk in product and add 50 milliliters of tetrahydrofuran (THF)s, drip the tetrahydrofuran solution (10 milliliters) of 2-amino-2-methyl propionitrile (4.3 grams, 50.8 moles).Under room temperature, stirred 12 hours, in reaction solution, add ethyl acetate (150 milliliters), the extraction of water (50 milliliters) separatory, organic phase is used the saturated common salt water washing successively, anhydrous magnesium sulfate drying, solvent is to the greatest extent steamed in decompression, and (ethyl acetate: sherwood oil=1: 3) recrystallization obtains 6.01 gram yellow solids, yield 90% with ethyl acetate, sherwood oil.
(6), compound 4 is synthetic
In the reaction flask of 100 milliliters, add the chloro-5-cyano group-N-of 2-amino-3-(2-cyano group-2-propyl group) benzamide (2.0 grams, 7.6 mmole), 20 milliliters of tetrahydrofuran (THF)s and sodium hydride (0.3 gram, 7.6 mmole), under room temperature, reaction is 30 minutes, drip 1-(3-chloropyridine-2-yl)-bromo-1H-pyrazoles of 3--5-formyl chloride (2.4 grams, 7.6 mmole, its the preparation referring to WO2008134969A1, example 2 steps (8)) tetrahydrofuran solution (10 milliliters).React and reacted completely in 3 hours, by in reaction solution impouring 100 ml waters, with 2 * 100 milliliters of ethyl acetate extractions, organic layer saturated sodium carbonate solution, saturated common salt water washing, concentrated after anhydrous magnesium sulfate drying, resistates column chromatography purification (leacheate: ethyl acetate: sherwood oil=1: 1), obtain 2.41 gram white solids, yield: 58%.
1H?NMR(300MHz，DMSO-d
6)：10.76(s，1H)，8.98(s，1H)，8.45(dd，1H)，8.24(d，1H)，8.09(dd，1H)，7.94(d，1H)，7.57(dd，1H)，7.48(s，1H)，1.51(s，6H)。
The preparation of example 2, compound 11
In the reaction flask of 50 milliliters, add the chloro-5-cyano group-N-of 2-amino-3-(2-cyano group-2-propyl group) benzamide (0.3 gram, 1.2 mmole), 10 milliliters of tetrahydrofuran (THF)s and sodium hydride (0.05 gram, 1.2 mmole), under room temperature, reaction is 30 minutes, drip 1-(3-chloropyridine-2-yl)-chloro-1H-pyrazoles of 3--5-formyl chloride (0.3 gram, 1.2 mmole, it prepares referring to 1 step 11 of example in WO2008134969A1) tetrahydrofuran solution (5 milliliters).React and reacted completely in 3 hours, by in reaction solution impouring 100 ml waters, with 2 * 100 milliliters of ethyl acetate extractions, organic layer saturated sodium carbonate solution, saturated common salt water washing, concentrated after anhydrous magnesium sulfate drying, resistates column chromatography purification (leacheate: ethyl acetate: sherwood oil=1: 1), obtain 0.42 gram white solid, yield: 62%.
1H?NMR(300MHz，DMSO-d
6)：9.69(br?s，1H)，8.46(dd，1H)，7.87(dd，1H)，7.77(d，1H)，7.72(d，1H)，7.42(dd，1H)，7.07(s，1H)，6.81(br?s，1H)，1.72(s，6H)。
The preparation of example 3, compound 28
In 100 milliliters of reaction flasks, add the chloro-5-cyano group-N-of 2-amino-3-(2-cyano group-2-propyl group) benzamide (0.5 gram, 1.9 mmole), 10 milliliters of tetrahydrofuran (THF)s, sodium hydride (0.08 gram, 1.9 mmole) stirring at room is after half an hour, drip 1-(3,5-dichloropyridine-2-yl)-3-Trifluoromethyl-1 H-pyrazoles-5-formyl chloride (0.7 gram, 1.9 mmole, its the preparation referring to 2 steps 4 of example in WO2010003350A1) tetrahydrofuran solution (5 milliliters), stirring at room 3 hours.By in reaction solution impouring 100 ml waters, with 2 * 100 milliliters of ethyl acetate extractions, organic layer saturated sodium carbonate solution, saturated common salt water washing, concentrated after anhydrous magnesium sulfate drying, resistates column chromatography purification (leacheate: ethyl acetate: sherwood oil=1: 1), obtain 0.36 gram white solid, yield: 35%.
1H?NMR(300MHz，DMSO-d
6)：11.01(s，1H)，9.05(s，1H)，8.65(d，1H)，8.59(d，1H)，8.35(s，1H)，8.04(s，1H)，7.86(s，1H)，1.51(s，6H)。
According to above method, can prepare other compound of Formula I of the present invention.
1H NMR (300MHz, the DMSO-d6) data of part of compounds are as follows:
Compound 5:10.78 (s, 1H), 9.00 (s, 1H), 8.49 (dd, 1H), 8.46 (d, 1H), 8.16 (dd, 1H), 8.04 (d, 1H), 7.61 (dd, 1H), 7.51 (s, 1H), 1.51 (s, 6H).
Compound 6:10.75 (s, 1H), 8.96 (s, 1H), 8.43 (s, 1H), 8.06 (s, 1H), 8.00 (d, 1H), 7.81 (s, 1H), 7.56 (s, 1H), 7.45 (s, 1H), 1.52 (s, 6H).
Compound 12:9.87 (br s, 1H), 8.42 (dd, 1H), 8.08 (br s, 1H), (7.84 dd, 1H), 7.78 (d, 1H), 7.75 (d, 1H), (7.38 dd, 1H), 7.18 (s, 1H), 1.66 (s, 6H).
Compound 16:10.55 (s, 1H), 8.87 (s, 1H), (8.40 dd, 1H), 8.15 (d, 1H), (8.00 dd, 1H), 7.88 (d, 1H), (7.49 d, 1H), 6.87 (s, 1H), (4.85 s, 2H), 3.36 (s, 1H), 1.51 (s, 6H).
Compound 17:10.54 (s, 1H), 8.86 (s, 1H), 8.40-8.31 (m, 2H), (7.99-7.92 m, 2H), 7.45 (d, 1H), 6.88 (s, 1H), (4.85 s, 2H), 3.42 (s, 1H), 1.50 (s, 6H).
Compound 24:10.88 (s, 1H), 9.05 (s, 1H), 8.61 (d, 1H), 8.52 (d, 1H), 8.33 (d, 1H), 8.02 (d, 1H), 7.54 (s, 1H), 1.56 (s, 6H).
Compound 25:10.82 (s, 1H), 8.99 (s, 1H), 8.54 (s, 1H), 8.44 (s, 1H), 8.06 (d, 1H), 7.86 (s, 1H), 7.48 (s, 1H), 1.53 (s, 6H).
Compound 26:10.99 (s, 1H), 9.07 (s, 1H), 8.67 (d, 1H), 8.59 (d, 1H), 8.39 (s, 1H), 8.09 (s, 1H), 7.51 (s, 1H), 1.59 (s, 6H).
Compound 27:10.83 (s, 1H), 8.99 (s, 1H), 8.52 (d, 1H), 8.41 (d, 1H), 8.05 (d, 1H), 7.85 (s, 1H), 7.42 (s, 1H), 1.53 (s, 6H).
Compound 29:10.99 (s, 1H), 9.02 (s, 1H), 8.65 (d, 1H), 8.59 (d, 1H), 8.47 (s, 1H), 8.06 (s, 1H), 7.86 (s, 1H), 1.51 (s, 6H).
Compound 30:10.91 (s, 1H), 8.95 (s, 1H), 8.49 (d, 1H), 8.30 (d, 1H), 7.91-7.81 (m, 2H), 7.79 (s, 1H), 1.56 (s, 6).
Compound 31:10.74 (s, 1H), 8.96 (s, 1H), 8.50 (d, 1H),, 8.35 (s, 1H), 8.22 (s, 1H), 7.93 (d, 1H), 6.97 (s, 1H), 5.15 (s, 2H), 1.52 (s, 6H).
Compound 32:10.73 (s, 1H), 8.95 (s, 1H), 8.54-8.41 (m, 3H), 8.00 (s, 1H), 6.98 (s, 1H), 5.18 (s, 2H), 1.64 (s, 6H).
Compound 33:10.74 (s, 1H), 8.96 (s, 1H), (8.50 d, 1H), 8.35 (s, 1H), (8.22 s, 1H), 7.93 (d, 1H), (6.97 s, 1H), 6.11-6.08 (m, 1H), (5.42 dd, 1H), 5.28 (dd, 1H), (4.65 d, 2H), 1.52 (s, 6H).
34：10.72(s，1H)，8.94(s，1H)，8.44(d，1H)，8.24(d，1H)，8.13(d，1H)，7.89(d，1H)，7.08(s，1H)，4.77(q，2H)，1.53(s，6H)。
Compound 35:10.56 (s, 1H), 8.87 (s, 1H), 8.40-8.31 (m, 1H), (8.25 d, 2H), 7.82 (d, 1H), 6.87 (s, 1H), (4.85 s, 2H), 3.43 (s, 1H), 1.51 (s, 6H).
Compound 36:10.55 (s, 1H), 8.86 (s, 1H), 8.41 (d, 1H), (8.23-8.07 m, 2H), 7.81 (m, 1H), 6.85 (s, 1H), (4.81 s, 2H), 3.42 (s, 1H), 1.52 (s, 6H).
The biological activity determination result
The mensuration of example 4, insecticidal activity
Kill the mensuration of black peach aphid activity
According to the solvability of testing compound, former medicinal acetone or methyl-sulphoxide dissolve, and then with 1 ‰ tween 80 solution preparation, become 50 milliliters of the liquid to be measured of desired concn, and acetone or the methyl-sulphoxide content in solution is no more than 10%.
6 centimetres, cut-off footpath culture dish, cover one deck filter paper at the bottom of ware, and drip appropriate tap water moisturizing.From clip suitable size (3 centimetres of diameters) on the cabbage plant of cultivating black peach aphid and the long cabbage leaves that 15～30 aphids are arranged, remove the aphid of alatae and face of blade, after the investigation radix, blade back upwards is placed in culture dish, with the processing of spraying of hand-held airbrush atomizer, every processing repeats for 3 times, processes and is placed in standard observation ward, 48 hours " Invest, Then Investigate " survival borer populations, calculate mortality ratio.
In the compound of part for examination, following compounds prevention effect to black peach aphid when concentration is 100ppm is better, and mortality ratio is more than 80%: 4,11.
In the compound of part for examination, following compounds prevention effect to black peach aphid when concentration is 25ppm is better, and mortality ratio is more than 80%: 4,11,24.
According to above method, choose the replicate(determination) that compound 4,11 and known compound KC (No. 1.23, the compound in WO 2008134969A1) have carried out killing the black peach aphid activity.Test-results is in Table 2.
Table 2: compound 4,11 and known compound KC kill the active parallel comparison of black peach aphid (mortality ratio, %)
Claims (4)
1. a N-(cyano group alkyl) benzamide compound, as shown in general formula I:
R
1Be selected from H;
R
2Be selected from methyl;
R
3Be selected from methyl;
R
4Be selected from Cl;
R
5Be selected from Cl or Br;
R
6Be selected from H.
2. one kind is used for controlling the purposes of aphid insect damage as agricultural insecticide according to compound of Formula I claimed in claim 1.
3. insect-killing composition, containing compound shown in general formula I as claimed in claim 1 is the upper acceptable carrier of active ingredient and agricultural, in composition, the weight percentage of active ingredient is 1-99%.
4. method of controlling aphid insect damage is characterized in that: composition claimed in claim 3 is imposed on the medium of insect that needs control or its growth to the effective dose of 1000 grams with per hectare 10 grams.
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| CN105367548A (en) * | 2015-10-21 | 2016-03-02 | 邓方坤 | Cyan dihalogenation pyrazol amide series compound and preparation method and application thereof |
| CN109988150B (en) | 2017-12-29 | 2022-04-12 | 江苏中旗科技股份有限公司 | N-alkyl-N-cyanoalkyl benzamide compounds and application thereof |
| WO2019128871A1 (en) * | 2017-12-29 | 2019-07-04 | 江苏中旗科技股份有限公司 | N-alkyl-n-cyanoalkylbenzamide compound and use thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
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| 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 |
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