CN102442967B - Dichloropropylene compound and application thereof - Google Patents

Dichloropropylene compound and application thereof Download PDF

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CN102442967B
CN102442967B CN201010502790.5A CN201010502790A CN102442967B CN 102442967 B CN102442967 B CN 102442967B CN 201010502790 A CN201010502790 A CN 201010502790A CN 102442967 B CN102442967 B CN 102442967B
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compound
general formula
trifluoromethyl
formula
milliliters
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CN102442967A (en
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关爱莹
李斌
常秀辉
梁松军
宋玉泉
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Shenyang Sinochem Agrochemicals R&D Co Ltd
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Shenyang Research Institute of Chemical Industry Co Ltd
Sinochem Corp
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Abstract

The invention discloses a dichloropropylene compound with a novel structure. The compound is shown as a general formula I in the specifications, wherein Q is selected from Q1, Q2 or Q3; R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11 and R12 can be the same or different, and are selected from H, fluorine, chlorine, bromine, iodine, CN, NO2, alkyl with 1-3 carbon atoms, haloalkyl with 1-3 carbon atoms, alkoxy with 1-3 carbon atoms or haloalkoxy with 1-3 carbon atoms respectively; X is selected from O, S or N-R13; R13 is selected from alkyl with 1-3 carbon atoms, allyl or propargyl; and n is equal to 2, 3, 4, 5 or 6. A compound I shown as the general formula has excellent insecticidal activity, and can be used for preventing and controlling insect pest.

Description

A kind of dichloropropylene compound and application thereof
Technical field
The invention belongs to field of pesticides.Relate to a kind of dichloropropylene 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 the composition of improved tool insecticidal activity.
In WO9604228A1, disclose dichloropropylene compound as follows (compound 213 in patent, below code name KC) and insecticidal activity thereof, under the concentration of 500ppm, prodenia litura lethality rate reached more than 80%:
Figure BSA00000297413900011
In prior art, as shown in the present containing (replacement) benzheterocycle or substituted pyridines ring, and contain the dichloropropylene compound of substituted alkyl bridge and insecticidal activity has no open simultaneously.
Summary of the invention
The object of the present invention is to provide a kind of novel structure, the better dichloropropylene compound of insecticidal activity, it can be applicable to the control of insect pest in agricultural, forestry or health.
Technical scheme of the present invention is as follows:
The invention provides one and contain (replacement) benzheterocycle or substituted pyridines ring, and contain the dichloropropylene compound of substituted alkyl bridge simultaneously, as shown in general formula I:
Figure BSA00000297413900012
In formula:
Q is selected from Q as follows 1, Q 2or Q 3:
Figure BSA00000297413900013
Wherein: R 1, R 2, R 3, R 4, R 5, R 6, R 7, R 8, R 9, R 10, R 11, R 12can be identical or different, be selected from respectively H, fluorine, chlorine, bromine, iodine, CN, NO 2, C 1-C 3alkyl, C 1-C 3haloalkyl, C 1-C 3alkoxyl group or C 1-C 3halogenated alkoxy;
X is selected from O, S or N-R 13; R 13be selected from C 1-C 3alkyl, allyl group or propargyl;
N=1,2,3 or 4.
According to the different choice of Q, dichloropropylene ether compound of the present invention can be expressed as following three kinds of structures:
Figure BSA00000297413900021
In the present invention, more preferably compound is, in general formula I:
Q is selected from Q 1, Q 2or Q 3;
When Q is selected from Q 1time, R 1, R 2, R 3, R 4be selected from respectively H, fluorine, chlorine, bromine, methyl or trifluoromethyl, but R 1, R 2in have one at least for H, R 3, R 4in have one at least for H; X is selected from O, S or N-R 13, R 13be selected from methyl;
When Q is selected from Q 2time, R 5, R 6, R 7, R 8be selected from respectively H, fluorine, chlorine, bromine, methyl or trifluoromethyl, but R 5, R 6in have one at least for H, R 7, R 8in have one at least for H;
When Q is selected from Q 3time, R 9, R 10, R 11, R 12be selected from respectively H, fluorine, chlorine, bromine, methyl or trifluoromethyl;
N=1,2 or 3.
In the present invention, further preferred compound is, in general formula I:
Q is selected from Q 1, Q 2or Q 3;
When Q is selected from Q 1time, R 1, R 2, R 3, R 4be selected from respectively H, chlorine or trifluoromethyl, but R 1, R 2in have one at least for H, R 3, R 4in have one at least for H; X is selected from O or S;
When Q is selected from Q 2time, R 5, R 6, R 7, R 8be selected from respectively H, chlorine or trifluoromethyl, but R 5, R 6in have one at least for H, R 7, R 8in have one at least for H;
When Q is selected from Q 3time, R 9, R 10, R 11, R 12be selected from respectively H, chlorine or trifluoromethyl;
N=1 or 2.
In the present invention, further preferred compound is again, in general formula I:
Q is selected from Q 1or Q 2;
R 1, R 5, R 8be selected from H;
R 2, R 3be selected from H, chlorine or trifluoromethyl;
R 4be selected from H or chlorine;
R 6, R 7be selected from H or trifluoromethyl;
N=1 or 2.
In the present invention, further preferred compound is, in general formula I:
Q is selected from Q 1;
R 1, R 3, R 4be selected from H;
R 2be selected from trifluoromethyl;
n＝2。
Or further preferred compound is in the present invention, in general formula I:
Q is selected from Q 2;
R 5, R 6, R 8be selected from H;
R 7be selected from trifluoromethyl;
n＝2。
In the definition of the compound of Formula I providing, collect term General Definition used as follows above:
Alkyl refers to straight or branched form, for example methyl, ethyl, n-propyl, isopropyl group.Haloalkyl refers to the group that alkyl is replaced by one or more halogen atoms, for example trifluoromethyl.Alkoxyl group refers to that alkyl end is connected with the group of Sauerstoffatom, such as methoxyl group, oxyethyl group, positive propoxy, isopropoxy etc.Halogenated alkoxy refers to that alkyl is replaced by one or more halogen atoms, and end is connected with the group of Sauerstoffatom, for example trifluoromethoxy.Halogen atom refers to fluorine, chlorine, bromine, iodine.
Compound of Formula I of the present invention can be prepared by the following method, and outside indicating, in reaction formula, each group definition is the same.
Work as Q=Q 1time:
Figure BSA00000297413900031
General formula I I, IV and V compound respectively with general formula III (in formula: n=1,2,3 or 4) compound in suitable solvent, under suitable alkali exists, temperature makes target compound I-1, I-2 and I-3 for-10 DEG C for 0.5-48 hour to reacting under boiling point.
Suitable solvent is selected from methylene dichloride, chloroform, tetracol phenixin, hexane, benzene, toluene, ethyl acetate, acetonitrile, tetrahydrofuran (THF), dioxane, DMF or dimethyl sulfoxide (DMSO) etc.
Suitable alkali comprises that basic metal is if the hydrogen compound of lithium, sodium or potassium is as sodium hydride, and basic metal is if the oxyhydroxide of lithium, sodium or potassium is as sodium hydroxide, can also be alkali-metal carbonate as sodium carbonate, can be also that organic bases is as triethylamine, sodium tert-butoxide etc.
In the time of X=O, the preparation of general formula I I compound is carried out with reference to the operation of following document: J.Org.Chem.1996,61,3289-3297; Bioorganic & Medicinal Chemistry Letters 17 (2007) 4689-4693.
In the time of X=S, the preparation of general formula I I compound is carried out with reference to the operation of following document: J.Am.Chem.Soc.1927,49,1748-1758; ARKIVOC 2008 (xiv) 109-114.
Work as X=N-R 13time, the method preparation that general formula I I compound provides with reference to CN1425665A (embodiment 5,7).
The preparation of compound of formula III is carried out with reference to the operation of following document: chemistry world, 6,366-370:2006; CN1432555A.
The preparation of general formula I V compound is carried out with reference to the operation of following document: Journal of Medicinal Chemistry, 24 (1), 93-101; 1981; Journal of Medicinal Chemistry, 44 (11), 1785-1776; 2001.
Substituted pyridines shown in general formula V all has commercially available.
Table 1 to table 3 has been listed structure and the physical properties of part compound of Formula I.
Structure and the physical properties of table 1 part general formula I-1 compound
Figure BSA00000297413900041
Compound R 1 R 2 R 3 R 4 X n Outward appearance (fusing point (DEG C))
1 H H H H O 1 Yellow oil
1a H H H H O 2 Yellow oil
2 H Cl H H O 1 Yellow oil
3 H CF 3 H H O 1 Yellow oil
3a H CF 3 H H O 2 Yellow oil
4 H H Cl H O 1 Yellow oil
5 H H CF 3 H O 1 Yellow oil
6 H CF 3 H Cl O 2 Yellow oil
7 H Cl H H S 1 Yellow oil
Structure and the physical properties of table 2 part general formula I-2 compound
Figure BSA00000297413900042
Compound R 5 R 6 R 7 R 8 n Outward appearance (fusing point (DEG C))
8 H H CF 3 H 1 Yellow oil
9 H H CF 3 H 2 Yellow solid (94-96)
10 H CF 3 H H 1 Yellow oil
11 H CF 3 H H 2 Yellow solid (87-89)
Structure and the physical properties of table 3 part general formula I-3 compound
Compound R 9 R 10 R 11 R 12 n Outward appearance (fusing point (DEG C))
12 Cl H Cl Cl 1 Yellow oil
Part of compounds 1h NMR (300MHz, CDCl 3) data are as follows:
Compound 1:1.47 (d, 3H), 4.24 (t, 2H), 4.57 (d, 2H), 5.52-5.56 (m, 1H), 6.12 (t, 1H), 6.81 (s, 2H), 7.17-7.27 (m, 2H), 7.36 (d, 1H), 7.49 (d, 1H).
Compound 1a:1.62 (d, 3H), 2.20-2.40 (m, 2H), 4.16 (t, 2H), 4.12 (t, 1H), 4.58 (d, 2H), 5.52-5.56 (m, 1H), 6.10 (t, 1H), 6.82 (s, 2H), 7.15-7.27 (m, 2H), 7.35 (d, 1H), 7.50 (d, 1H).
Compound 2:1.65 (d, 3H), 4.23 (t, 2H), 4.57 (d, 2H), 5.50-5.60 (m, 1H), 6.10 (t, 1H), 6.83 (s, 2H), 7.16 (d, 1H), 7.28 (s, 1H), 7.46 (s, 1H).
Compound 3:1.67 (d, 3H), 4.24 (t, 2H), 4.57 (d, 2H), 5.50-5.60 (m, 1H), 6.10 (t, 1H), 6.83 (s, 2H), 7.45-7.47 (m, 2H), 7.75 (s, 1H).
Compound 3a:1.64 (d, 3H), 2.28-2.32 (m, 2H), 4.10-4.13 (m, 3H), 4.56 (d, 2H), 6.10 (t, 1H), 6.81 (s, 2H), 7.26 (dd, 1H), 7.40-7.50 (m, 2H), 7.76 (s, 1H).
Compound 4:1.63 (d, 3H), 4.23 (t, 2H), 4.57 (d, 2H), 5.50-5.53 (m, 1H), 6.10 (t, 1H), 6.83 (s, 2H), 7.23 (dd, 1H), 7.37-7.39 (m, 2H).
Compound 5:1.67 (d, 3H), 4.24 (t, 2H), 4.57 (d, 2H), 5.50-5.53 (m, 1H), 6.10 (t, 1H), 6.82 (s, 2H), 7.54-7.63 (m, 3H).
Compound 6:1.64 (d, 3H), 2.28-2.32 (m, 2H), 4.11 (t, 2H), 4.12 (t, 1H), 4.56 (d, 2H), 5.50-5.50 (m, 1H), 6.10 (t, 1H), 6.821 (s, 2H), 7.47 (d, 1H), 7.65 (d, 1H).
Compound 7:1.63 (d, 3H), 4.24 (t, 2H), 4.57 (d, 2H), 5.50-5.60 (m, 1H), 6.10 (t, 1H), 6.83 (s, 2H), 7.20 (dd, 1H), 7.54 (d, 1H), 7.66 (d, 1H).
Compound 8:1.62 (d, 3H), 4.25 (t, 2H), 4.56 (d, 2H), 5.70-5.90 (m, 1H), 6.10 (t, 1H), 6.82 (s, 2H), 7.86-7.90 (m, 2H), 8.31 (s, 1H), 8.55 (s, 1H).
Compound 9:1.55 (d, 3H), 2.29-2.30 (m, 2H), 4.12 (t, 2H), 4.54 (d, 2H), 5.81-5.90 (m, 1H), 6.09 (t, 1H), 6.78 (s, 2H), 7.84-7.94 (m, 2H), 8.31 (s, 1H), 8.52 (s, 1H).
Compound 10:1.62 (d, 3H), 4.25 (t, 2H), 4.56 (d, 2H), 5.80-5.82 (m, 1H), 6.10 (t, 1H), 6.81 (s, 2H), 7.74 (d, 1H), 8.12 (s, 2H), 8.60 (s, 1H).
Compound 11:1.55 (d, 3H), 2.29-2.31 (m, 2H), 4.12 (t, 2H), 4.55 (d, 2H), 5.70-5.90 (m, 1H), 6.09 (t, 1H), 6.79 (s, 2H), 7.75 (dd, 1H), 8.11-8.15 (d, 2H), 8.53 (s, 1H).
Compound 12:1.54 (d, 3H), 4.12 (t, 2H), 4.57 (d, 2H), 5.50-5.70 (m, 1H), 6.10 (t, 1H), 6.82 (s, 2H), 7.70 (s, 1H).
Compare with known dichloropropylene compound, the dichloropropylene compound shown in general formula I of the present invention has beyond thought high insecticidal activity.Therefore, the present invention also comprises that compound of Formula I can be used for controlling the purposes of insect pest.
The present invention also comprises the insect-killing composition using 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 in agricultural, forestry, health.
Composition of the present invention can preparation form use.Compound of Formula I is easier to as solubilization of active ingredient or when being scattered in carrier or being mixed with preparation to using as desinsection disperse.For example: these chemicals can be made into wettable powder or missible oil.In these compositions, at least add a kind of liquid or solid carrier, and can add when needed suitable tensio-active agent.
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.Conventionally the comparatively suitable significant quantity of selecting is 10 grams to 1000 grams of per hectares, and preferably significant quantity is 20 grams to 500 grams of per hectares.
For some application, for example in agricultural, can in insect-killing composition of the present invention, add one or more other sterilant, Insecticides (tech) & Herbicides (tech), plant-growth regulator or fertilizer etc., can produce thus additional advantage and effect.
Should be clear and definite, in claim limited range of the present invention, can carry out various conversion and change.
Embodiment
Following synthetic example, biological activity determination example 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 2
Figure BSA00000297413900061
In reaction flask, add 3-(2, the chloro-4-(3 of 6-bis-, the chloro-allyloxy of 3-bis-) phenoxy group) propan-2-ol (0.50 gram, 1.44 mmoles, synthetic method is with reference to chemistry world, 2006,6,366), tetrahydrofuran (THF) (10 milliliters), under room temperature, be stirred to dissolving, add 70% sodium hydride (0.10 gram, 2.88 mmoles), stir after 2 hours, add 2,5-dichloro benzoxazoles (0.27 gram, 1.44 mmoles, synthetic method is with reference to J.Org.Chem.1996,61,3294).Under room temperature, continue reaction after 5 hours, by in reaction solution impouring water (50 milliliters), extract by ethyl acetate (3 × 100 milliliters), organic layer is used respectively saturated sodium bicarbonate aqueous solution (3 × 50 milliliters), saturated aqueous common salt (3 × 50 milliliters) washing, anhydrous magnesium sulfate drying, solvent is to the greatest extent steamed in decompression.Resistates is by the column chromatography (leacheate: ethyl acetate: sherwood oil=1: 50) obtain 0.32 and digest compound 2, outward appearance: colorless oil of purifying.Yield 35%.
The preparation of example 2 compound 3a
In reaction flask, add 3-(2, the chloro-4-(3 of 6-bis-, the chloro-allyloxy of 3-bis-) phenoxy group) (0.50 gram of fourth-2-alcohol, 1.44 mmole, embodiment 1 in synthetic method referenced patent CN1432555A, 2), tetrahydrofuran (THF) (10 milliliters), under room temperature, be stirred to dissolving, add (0.10 gram of 70% sodium hydride, 2.88 mmole), stir after 2 hours, add (0.31 gram of the chloro-5-trifluoromethyl of 2-benzo oxazole, 1.44 mmole, synthetic method is with reference to J.Org.Chem.1996, 61, 3294), under room temperature, continue reaction after 5 hours, by in reaction solution impouring water (50 milliliters), extract by ethyl acetate (3 × 100 milliliters), organic layer is used respectively saturated sodium bicarbonate aqueous solution (3 × 50 milliliters), saturated aqueous common salt (3 × 50 milliliters) washing, anhydrous magnesium sulfate drying, solvent is to the greatest extent steamed in decompression.Resistates is by the column chromatography (leacheate: ethyl acetate: sherwood oil=1: 100) obtain 0.2 and digest compound 3a, outward appearance: colorless oil of purifying.Yield 22%.
The preparation of example 3 compounds 9
Figure BSA00000297413900072
In reaction flask, add 3-(2, the chloro-4-(3 of 6-bis-, 3-bis-chloroallyloxyaminos) phenoxy group) (0.50 gram of fourth-2-alcohol, 1.44 mmoles), tetrahydrofuran (THF) (10 milliliters), under room temperature, be stirred to dissolving, add 70% sodium hydride (0.10 gram, 2.88 mmoles).Stir after 2 hours, add the chloro-6-trifluoromethyl of 2-quinoxaline (0.32 gram, 1.44 mmoles, synthetic method is with reference to J.Med.Chem.1981,24 (1), 93), under room temperature, continue reaction 6 hours.Afterwards, by in reaction solution impouring water (50 milliliters), extract by ethyl acetate (3 × 150 milliliters), organic layer is used respectively saturated sodium bicarbonate aqueous solution (3 × 50 milliliters), saturated aqueous common salt (3 × 50 milliliters) washing, anhydrous magnesium sulfate drying, solvent is to the greatest extent steamed in decompression.Resistates is by the column chromatography (leacheate: ethyl acetate: sherwood oil=1: 100) obtain 0.30 and digest compound 9, outward appearance: yellow solid of purifying.Yield 31%.
The preparation of example 4 compounds 12
Figure BSA00000297413900073
In reaction flask, add 3-(2, the chloro-4-(3 of 6-bis-, the chloro-allyloxy of 3-bis-) phenoxy group) (0.50 gram of propan-2-ol, 1.44 mmole), tetrahydrofuran (THF) (10 milliliters), under room temperature, be stirred to dissolving, add (0.10 gram of 70% sodium hydride, 2.88 mmole), stir after 2 hours, add 2, 3, 5, (0.30 gram of 6-4 chloro pyridine, 1.44 mmole, commercially available), under room temperature, continue reaction after 10 hours, by in reaction solution impouring water (50 milliliters), extract by ethyl acetate (3 × 100 milliliters), organic layer is used respectively saturated sodium bicarbonate aqueous solution (3 × 50 milliliters), saturated aqueous common salt (3 × 50 milliliters) washing, anhydrous magnesium sulfate drying, solvent is to the greatest extent steamed in decompression.Resistates is by the column chromatography (leacheate: ethyl acetate: sherwood oil=1: 500) obtain 0.05 and digest compound 12, outward appearance: colorless oil of purifying.Yield 7%.
Other compound of Formula I of the present invention can be prepared with reference to aforesaid method.
Biological activity determination example
The mensuration of example 5 insecticidal activities
According to the solvability of testing compound, dissolve former medicine with acetone or methyl-sulphoxide, then become 50 milliliters of the liquid to be measured of desired concn with 1 ‰ tween 80 solution preparation, acetone or the methyl-sulphoxide content in total solution is no more than 10%.
(1), kill the mensuration of small cabbage moth activity
Cabbage leaves is broken into the leaf dish of 3 centimetres of diameters with punch tool, process with Airbrush spraying, certain density test compound liquid is sprayed at every leaf dish pros and cons, spouting liquid is 0.5 milliliter, separately establishes clear water and is treated to blank, and every processing repeats for 3 times.Every processing 8 examination worms of access (3 age) after drying in the shade.After processing, put into 24 DEG C, the indoor cultivation of relative humidity 60%～70%, unglazed photograph, 72 hours " Invest, Then Investigate " survival borer populations, calculate mortality ratio.
In the compound of part for examination, following compounds prevention effect to small cabbage moth in the time that concentration is 100ppm is better, and mortality ratio is more than 90%: 3a, 9.
According to above method, choose compound 3a and 9 and known compound KC (compound 213 in WO9604228A1) carried out killing the mensuration of small cabbage moth activity.Test-results is in table 4.
Table 4 kills small cabbage moth activity (mortality ratio, %)
Figure BSA00000297413900081
(2), the mensuration of killing beet noctuids activity
Adopt artificial diet medicine embrane method.Get 24 orifice plates, every hole adds 1 milliliter of the artificial diet that people prepares, after feed is cooling, with continous sample adding apparatus, according to test design, the order from low dosage to high dosage adds the liquid preparing, shake makes it form uniform medicine film on feed surface gently, naturally after drying in the shade, neat healthy the supplying of access tries insect, 1, every hole, totally 48 of every processing.Separately establish clear water and be treated to blank.After processing, put into 24 DEG C, the indoor cultivation of relative humidity 60%～70%, unglazed photograph, 72 hours " Invest, Then Investigate " survival borer populations, calculate mortality ratio.
In the compound of part for examination, following compounds prevention effect to beet armyworm in the time that concentration is 600ppm is better, and mortality ratio is 100%:2,3,3a, 7,8,9.
According to above method, choose compound 3a and 9 and known compound KC (compound 213 in WO9604228A1) carried out the mensuration of killing beet noctuids activity.Test-results is in table 5.
Table 5 killing beet noctuids activity (mortality ratio, %)
Figure BSA00000297413900091
(3), the mensuration of mythimna separate
Maize leaf is cut into 4-5 cm long segment, processes with Airbrush spraying, certain density test compound liquid is sprayed in every leave dual sides, spouting liquid is 0.5 milliliter, separately establishes clear water and is treated to blank, and every processing repeats for 3 times.Every processing 8 examination worms of access (3 age) after drying in the shade.After processing, put into 24 DEG C, the indoor cultivation of relative humidity 60%～70%, unglazed photograph, 72 hours " Invest, Then Investigate " survival borer populations, calculate mortality ratio.
In the compound of part for examination, following compounds prevention effect to mythimna separata in the time that concentration is 600ppm is better, and mortality ratio is 100%:1,1a, 2,3,4,5,6,7,8,10.
According to above method, choose compound 3a and 9 and known compound KC (compound 213 in WO9604228A1) carried out the mensuration of mythimna separate.Test-results is in table 6.
Table 6 mythimna separate (spraying medicine concentration: 10ppm)
Compound Insecticidal activity (mortality ratio, %)
3a 70
9 70
KC 0

Claims (6)

1. a dichloropropylene compound, as shown in general formula I:
Figure FSB0000123978200000011
In formula:
Q is selected from Q as follows 1or Q 2:
Figure FSB0000123978200000012
Wherein:
Q is selected from Q 1or Q 2; X is selected from O;
R 1, R 5, R 8be selected from H;
R 2, R 3be selected from H, chlorine or trifluoromethyl;
R 4be selected from H or chlorine;
R 6, R 7be selected from H or trifluoromethyl;
N=1 or 2.
2. according to compound claimed in claim 1, it is characterized in that following compound in general formula I:
Q is selected from Q 1;
R 1, R 3, R 4be selected from H;
R 2be selected from trifluoromethyl;
n=2。
3. according to compound claimed in claim 1, it is characterized in that following compound in general formula I: Q is selected from Q 2;
R 5, R 6, R 8be selected from H;
R 7be selected from trifluoromethyl;
n=2。
4. one kind according to the purposes of compound of Formula I control agricultural claimed in claim 1 or forestry insect pest.
5. an insect-killing composition, contains compound of Formula I as claimed in claim 1 as acceptable carrier in active ingredient and agricultural or forestry, and in composition, the weight percentage of active ingredient is 1-99%.
6. a method of controlling agricultural or forestry insect pest, is characterized in that: composition claimed in claim 5 is imposed on the insect of needs control or the medium of its growth with the effective dose of 10 grams to 1000 grams of per hectares.
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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1169147A (en) * 1994-10-14 1997-12-31 住友化学工业株式会社 Dihalopropene compounds, insecticidal/acaricidal agent contg. same, and intermediates
US5872137A (en) * 1994-08-04 1999-02-16 Sumitomo Chemical Company, Limited Dihalopropene compounds, insecticidal/acaricidal agents containing same, and intermediates for their production

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5872137A (en) * 1994-08-04 1999-02-16 Sumitomo Chemical Company, Limited Dihalopropene compounds, insecticidal/acaricidal agents containing same, and intermediates for their production
CN1169147A (en) * 1994-10-14 1997-12-31 住友化学工业株式会社 Dihalopropene compounds, insecticidal/acaricidal agent contg. same, and intermediates

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