CN1465563A - Novel benzoylurea compound and use thereof - Google Patents
Novel benzoylurea compound and use thereof Download PDFInfo
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Abstract
The present invention relates to a new type benzolyurea compound and its application. It is characterized by that it uses compound isocyanate and compound chlorothalonil derivative, and makes them produce reaction to prepare the invented product with higher insecticidal and ovicidal action. Said invention also provides its structural formula.
Description
Technical field
The present invention relates to prepare new benzoyl urea compound, and this novel cpd is used to control small cabbage moth with compound isocyanic ester and compound m-tetrachlorophthalodinitrile derivative.
Background technology
In existing benzoyl urea compound; people by a large amount of experiments verified basic structure be that a compounds of N-substituted benzene methyl-N-substituted benzoyl urea has higher insecticidal activity to insect, and useful aquatic Crustachia is had higher security.But, thereby increased overall synthetic difficulty because the substituted-phenyl part-structure complexity of most of benzoyl carbamide compounds is difficult synthetic.And do not synthesize compound (I) by compound (II) and compound (IV) reaction particularly as yet.That is:
Summary of the invention
The purpose of this invention is to provide a kind of raw material and be easy to get, new benzoyl urea compound that synthetic route is succinct and application thereof.
The derivative of the benzoyl urea that reaches of the present invention is represented by following general structure (I):
Wherein: R
1, R
2, R
6Be fluorine atom or chlorine atom; R
3Be fluorine atom or amino; R
4Be hydrogen, chlorine atom or fluorine atom.
This is that a class has unique effect mechanism, high environmental safety and the active compound of efficient insecticide.The present invention will address the synthesis technique of this compounds and they the indoor preventive effect test result to small cabbage moth.
The inventor has successfully synthesized the derivative suc as formula the benzoyl urea of the class novelty shown in (I) after having studied a compound with efficient insecticide effect extensively and profoundly.That is: with compound (isocyanic ester)
With compound (m-tetrachlorophthalodinitrile derivative)
Prepared in reaction gets following benzoylureas analog derivative:
Radicals R wherein
1, R
2, R
5Be fluorine atom or chlorine atom; R
3Be fluorine atom or amino; R
4Be hydrogen, chlorine atom or fluorine atom.
Also developed the represented compound of formula (I) in addition further, the agricultural pests diamondback moth larvae has been had tangible desinsection and antifeedant activity.
Below describe further:
(1) benzoylureas analog derivative (I)
(2) prepare one of the method for benzoylureas analog derivative (I).This method has comprised the reaction between compound (II) and the compound (IV).
(3) gratifying example or perhaps product of the present invention are some following compounds in the benzoylureas analog derivative.
Work as R
1Be F, R
2Be Cl, R
3During for F, R
4Be F, R
5Be F (I-1).
Work as R
1Be F, R
2Be Cl, R
3During for F, R
4Be Cl, R
5Be Cl (I-2).
Work as R
1Be F, R
2Be F, R
3During for F, R
4Be Cl, R
5Be H (I-3).
Work as R
1Be F, R
2Be F, R
3During for F, R
4Be F, R
5Be F (I-4).
Work as R
1Be F, R
2Be F, R
3Be NH
2The time, R
4Be Cl, R
5Be H (I-5).
Work as R
1Be F, R
2Be F, R
3Be NH
2The time, R
4Be F, R
5Be F (I-6).
Work as R
1Be F, R
2Be F, R
3Be NH
2The time, R
4Be Cl, R
5Be Cl (I-7).Wherein gratifying especially example is:
Work as R
1Be F, R
2Be F, R
3During for F, R
4Be Cl, R
5Be H.
Work as R
1Be F, R
2Be F, R
3During for F, R
4Be F, R
5Be F.
Work as R
1Be F, R
2Be F, R
3Be NH
2The time, R
4Be Cl, R
5Be Cl.
The method that the present invention prepares benzoylureas analog derivative (I) relates to following steps:
Intermediate (II-1): the preparation of 2-chloro-benzoyl isocyanic ester
15.5 gram (0.1mol) 2-chlorobenzamides are dissolved in are furnished with agitator, calcium chloride tube, reflux condensing tube with the hydrogen chloride gas absorption unit, dry new steaming 1, in the three-necked bottle of 2-ethylene dichloride, slowly add the new oxalyl chloride that steams of 14.5ml then, after the question response heat release finishes, till ebuillition of heated made suspended solids all clarify in 1 hour and do not have hydrogenchloride and emit, at last the reaction solution underpressure distillation is removed excessive 1,2-ethylene dichloride and oxalyl chloride, obtain light yellow oily liquid 17.4 grams, productive rate 96.0% need not further be purified, seal standbyly, or be used for next step reaction immediately.
Intermediate (II-2) 2, the preparation of 6-two fluoro-benzoyl isocyanic ester
With 11.8 gram (0.1mol) 2, the 6-difluorobenzamide is dissolved in is furnished with agitator, drying tube, dry new steaming 1 in the three-necked bottle of 2-ethylene dichloride, slowly adds the new oxalyl chloride that steams of 9.5ml then, after the question response heat release finished, ebuillition of heated spent the night suspended solids is all clarified, and at last the reaction solution underpressure distillation was removed excessive 1,2-ethylene dichloride and oxalyl chloride, obtain light yellow oily liquid 11.6 grams, productive rate 87.0% need not further be purified, seal standbyly, or be used for next step reaction immediately.
bp[29]：54℃(0.05mmHg)。
1HNMR(CDCl3)：7.01(t，J＝8.3hz，2H)，7.48-7.58(m，1H)。
Intermediate (II-3) 2, the preparation of 6-two chloro-benzoyl isocyanic ester 
The preparation method is with (II-2), and return time is 18～20h, and the reaction end mark is that suspended solids is all clarified, productive rate 65.0%.
Intermediate (III-1) 5-chloro-2,4,6-three cyanogen-1, the preparation of 3-benzene dinitrile 
In 250 milliliters of three-necked bottles, add 150 milliliters of dry N that cross, dinethylformamide adds m-tetrachlorophthalodinitrile 26.6 grams (0.1mol) that drying is handled, again under mechanical stirring, being warming up to 70 ℃ dissolves it fully, add fast 20.0 gram anhydrous potassium fluorides (0.345mol), and on the mouth of pipe of a side drying tube is installed aside, be warming up to 110 ℃ then, react after 3 hours, be cooled to room temperature, remove by filter precipitation (KF+KCl), and with 30 milliliters of N, 2-3 above-mentioned precipitation of dinethylformamide washing (precipitating heavily about 24.9 grams), merging filtrate is poured filtrate in 500 ml waters into, magnetic agitation 2 hours, suction filtration must precipitate 11.5 grams-18.7 grams, after the drying, use the hexanaphthene recrystallization, get white needle-like crystals, nearly weigh 10.4 grams-17.5 grams (yield 48%-81%), fusing point 107-108 ℃.
Intermediate (III-2) 2,4,5,6-tetrafluoro-1, the preparation of 3-benzene dinitrile 
In 250 milliliters of three-necked bottles, add 150 milliliters of exsiccant tetramethylene sulfone, add m-tetrachlorophthalodinitrile 26.6 grams that drying is handled again, under mechanical stirring, being warming up to 70 ℃ dissolves it fully, add 25.0 gram anhydrous potassium fluorides fast, 0.5 gram hexaoxacyclooctadecane-6-6 is made phase-transfer catalyst, and on the mouth of pipe of a side drying tube is installed aside, temperature control is in reaction between 160-180 ℃ after 8 hours then, be cooled to room temperature, remove by filter precipitation (KF+KCl), and, filtrate is poured in 500 ml waters with 2-3 above-mentioned precipitation of 20 milliliters of tetramethylene sulfone washings (precipitating heavily about 24.9 grams) merging filtrate, magnetic agitation 2 hours, suction filtration must precipitate 17.6 grams, after the drying, selects hexanaphthene to carry out recrystallization, get white, needle-shaped crystals, nearly weigh 16.4 grams (yield 70.7%).mp：102-104℃。
Intermediate (III-3) 2,5-two chloro-4,6-two fluoro-1, the preparation of 3-benzene dinitrile 
Operation is synthesizing of (III-1) substantially together, and the amount that is used KF is reduced to 12.0 grams (0.207mol), and the reaction times was condensed to 1 hour, and post separates to such an extent that white, needle-shaped crystals 10.2 restrains (yield 50.1%).mp：144-147℃。
Intermediate (IV-1) 6-amino-5-chloro-2,4-two fluoro-1, the preparation of 3-benzene dinitrile
With 40 gram (0.185mol) 5-chloro-2,4,6-three fluoro-1,3-benzene dinitrile (III-1) is dissolved in 150 grams 1, the 2-methyl ethyl ether, and slowly adding 30 gram d under stirring in 1 hour is 0.880g/cm2 25-28% ammoniacal liquor, afterwards reaction solution is heated to 60 ℃ of reactions 30 minutes, pour above-mentioned reaction solution in the 300 gram water fully stirring after the cooling, suction filtration obtains white solid, dry 28.6 grams (productive rate 72.4%) that get of washing final vacuum.
Intermediate (IV-2) 4,6-diamino-5-chloro-2-fluoro-1, the preparation of 3-benzene dinitrile
With 21.6 (0.1mol) gram 5-chloro-2,4,6-three fluoro-1,3-benzene dinitrile are dissolved in 150 grams 1, and the 2-methyl ethyl ether blasts ammonia to solution under stirring in 10 minutes.After extremely reaction finishes with the TLC detection, be cooled to 20 ℃, pour reaction solution in the 150 gram water fully stirring after the cooling, suction filtration obtains white solid, washes the dry 14.6. of the getting gram of final vacuum (productive rate 68.0%).
IR：3386，3327，3218，2247，1635，1520，1489，1376，1134，965
MS:210 (100), 191 (8), 175 (36), 148 (50), 121 (37)
Intermediate (IV-3) 6-amino-2,4,5-three fluoro-1, the preparation of 3-benzene dinitrile
With 20 gram (0.1mol) 2,4,5,6-tetrafluoro-1,3-benzene dinitrile are dissolved in 120 grams 1, the 2-methyl ethyl ether, and slowly adding 20 gram d under stirring in 1 hour is 0.880g/cm
225-28% ammoniacal liquor is heated to reaction solution 45 ℃ of reactions 2 hours afterwards, pours above-mentioned reaction solution in the 150 gram water fully stirring after the cooling, and suction filtration obtains white solid, dry 10.6 grams (productive rate 54.2%) that get of washing final vacuum.
IR：3346，3226，2255，1615，1523，1348，1267，959。
MS：197(100)，178(14)，170(65)，155(43)，139(57)。
Intermediate (IV-4) 4,6-diamino-2,5-two fluoro-1, the preparation of 3-benzene dinitrile
With 20 gram (0.1mol) 2,4,5,6-tetrafluoro-1,3-benzene dinitrile are dissolved in 150 grams 1, and the 2-methyl ethyl ether blasts ammonia to solution under stirring in 10 minutes.After extremely reaction finishes with the TLC detection, be cooled to 20 ℃, pour reaction solution in the 150 gram water fully stirring after the cooling, suction filtration obtains white solid, washes dry 17.2 grams (productive rate 89.0%) that get of final vacuum.
IR：3392，3320，3224，2239，1638，1518，1488，1382，1291，1007，799
MS:194 (47), 140 (16), 64 (100)
Intermediate (IV-5) 6-amino-4-fluoro-2,5-two chloro-1, the preparation of 3-benzene dinitrile
The same IV-1 of preparation method, productive rate 84.0%.
IR：3328，3235，2240，1665，1520，1489，1339，1298，942，896
MS：229(100)，213(50)，194(23)，178(8)，167(25)，158(13)，147(17)。
Intermediate (IV-6) 4,6-diamino-2,5-two chloro-1, the preparation of 3-benzene dinitrile
The same IV-2 of preparation method, productive rate 52.0%.
IR：3340，3328，32?16，2246，1628，1517，1493，1380，968
MS：226(47)，210(100)，175(35)，148(50)，121(37)。
The preparation of compound of the present invention
The general preparation method of compound (I): take by weighing an amount of benzoyl isocyanic ester (II) of preparation just, with drying 1, the 2-ethylene dichloride makes its dissolved dilution in being furnished with the flask of agitator; Other takes by weighing excessive slightly anils (IV), also use exsiccant 1, the 2-ethylene dichloride fully dissolves it and makes solution, stirs then slowly to drip to the above-mentioned ice cube refrigerative reaction flask of using down, separates out white solid immediately, after treating that heat release finishes, continue reaction 24 hours, suction filtration gained solid is monitored with TLC, if excessive aniline is less, available ethyl acetate-sherwood oil=recrystallization got white, needle-shaped crystals (I) in 1: 1; If excessive aniline is also many, with ethyl acetate-sherwood oil=column chromatography got target compound in 7: 3.Productive rate is almost quantitative.
The present invention selects for use the raw material m-tetrachlorophthalodinitrile (2,4,5,6-tetrachloro-1,3-benzene dinitrile) that is easy to get with a kind of Yunnan as the starting raw material of phenyl moiety, its structure is modified synthetic, obtains the benzoylureas analog derivative of a series of brand-new skeletons.Because the benzoylureas analog derivative has been introduced fungicide chlorothalonil as parent, therefore, compares with known similar compound, has higher desinsection ovicidal action; Again owing to fish and Mammals there being low toxicity extremely reduced harm to environment, therefore it can eradicate or stop house pest, the parasitic insect of animals and plants and injurious forest-insect effectively, experimental results show that it has insecticidal action efficiently, particularly more effective to cast off a skin restraining effect and the food refusal effect of larva, its method is insect directly to be contacted or absorb compound of the present invention to get final product.In whole process, have that raw material is easy to get, a novel structure, synthetic route is succinct, easy and simple to handle, productive rate is high advantage, reduce the people's livelihood greatly and produce cost, be particularly suitable for industrialized developing.
Specific embodiments
Embodiment 1:
N-(2-chlorobenzene formacyl)-N '-(2,4-dintrile-3,5,6-trifluorophenyl) urea takes by weighing 0.1 mole of benzoyl isocyanic ester II-1 of preparation just, and with drying 1, the 2-ethylene dichloride makes its dissolved dilution in being furnished with the flask of agitator; Other takes by weighing 0.11 mole anils IV-3, also uses exsiccant 1, and the 2-ethylene dichloride fully dissolves it and makes solution, stir then slowly to drip to down and above-mentionedly separate out white solid immediately with ice cube refrigerative reaction flask, treat that heat release finishes after, continue reaction 24 hours, suction filtration gained solid.Recrystallization gets white, needle-shaped crystals N-(2-chlorobenzene formacyl)-N '-(2,4-dintrile-3,5,6-trifluorophenyl) urea (I-3) 37 grams, productive rate 92%.
Embodiment 2:
N-(2, the 6-difluoro benzoyl)-N '-(2,4-dintrile-3,5,6-trifluorophenyl) urea takes by weighing 0.1 mole of benzoyl isocyanic ester II-2 of preparation just, and with drying 1, the 2-ethylene dichloride makes its dissolved dilution in being furnished with the flask of agitator; Other takes by weighing 0.12 mole anils IV-3, also uses exsiccant 1, and the 2-ethylene dichloride fully dissolves it and makes solution, stir then slowly to drip to down and above-mentionedly separate out white solid immediately with ice cube refrigerative reaction flask, treat that heat release finishes after, continue reaction 24 hours, suction filtration gained solid.Recrystallization gets white, needle-shaped crystals N-(2, the 6-difluoro benzoyl)-N '-(2,4-dintrile-3,5,6-trifluorophenyl) urea (I-4) 36 grams, productive rate 94%.
Embodiment 3:
N-(2, the 6-difluoro benzoyl)-N '-(2,4-dintrile-3,6-two fluoro-5-aminophenyls) urea takes by weighing 0.1 mole of benzoyl isocyanic ester II-2 of preparation just, and with drying 1, the 2-ethylene dichloride makes its dissolved dilution in being furnished with the flask of agitator; Other takes by weighing 0.13 mole anils IV-4, also uses exsiccant 1, and the 2-ethylene dichloride fully dissolves it and makes solution, stir then slowly to drip to down and above-mentionedly separate out white solid immediately with ice cube refrigerative reaction flask, treat that heat release finishes after, continue reaction 24 hours, suction filtration gained solid.Recrystallization gets white, needle-shaped crystals N-(2, the 6-difluoro benzoyl)-N '-(2,4-dintrile-3,6-two fluoro-5-aminophenyls) urea (I-7) 35 grams, productive rate 90%.
Below with the insecticidal effect of the indoor desinsection drug effect example explanation benzoyl urea derivative formulations of the preparation that contains the benzoylureas analog derivative.
The benzoylureas analog derivative is to the poisoning and the food refusal effect of diamondback moth larvae
Embodiment 1:
To contain 44% benzoylureas analog derivative (I-1) preparation is diluted to 500 times, 1000 times, 2000 times respectively and makes concentration and handle, the object crop is the wild cabbage of group's phase, for examination worm source is small cabbage moth 1～2 instar larvae, adopt leaf dish method, 24h, 48h, 72h investigate diamondback moth larvae survival number respectively behind medicine; And get the food area in 72h investigation.Drug effect result shows: contain 24h～72h after 500 times of dispensers of benzoylureas analog derivative (I-1) of 44%, corrected mortality is between 35.0%～75.0%, and the food refusal rate is 72.3% behind the 72h; 24h～72h after 1000 times of dispensers, corrected mortality are between 37.5%～70.0%, and the food refusal rate is 54.3% behind the 72h; 24h～72h after 2000 times of dispensers, corrected mortality are between 20.0%～55.0%, and the food refusal rate is 43.9% behind the 72h.
Embodiment 2:
To contain 54% benzoylureas analog derivative (I-2) preparation is diluted to 500 times, 1000 times, 2000 times respectively and makes concentration and handle, the object crop is the wild cabbage of group's phase, for examination worm source is small cabbage moth 1～2 instar larvae, adopt leaf dish method, 24h, 48h, 72h investigate diamondback moth larvae survival number respectively behind medicine; And get the food area in 72h investigation.Drug effect result shows: contain 24h～72h after 500 times of dispensers of benzoylureas analog derivative (I-2) of 54%, corrected mortality is between 50.0%～77.5%, and the food refusal rate is 85.2% behind the 72h; 24h～72h after 1000 times of dispensers, corrected mortality are between 52.5%～67.5%, and the food refusal rate is 76.4% behind the 72h; 24h～72h after 2000 times of dispensers, corrected mortality are between 40.0%～60.0%, and the food refusal rate is 67.3% behind the 72h.
Embodiment 3:
To contain 65% benzoylureas analog derivative (I-3) preparation is diluted to 500 times, 1000 times, 2000 times respectively and makes concentration and handle, the object crop is the wild cabbage of group's phase, for examination worm source is small cabbage moth 1～2 instar larvae, adopt leaf dish method, 24h, 48h, 72h investigate diamondback moth larvae survival number respectively behind medicine; And get the food area in 72h investigation.Drug effect result shows: contain 24h～72h after 500 times of dispensers of benzoylureas analog derivative (I-3) of 65%, corrected mortality is between 60.0%～72.5%, and the food refusal rate is 87.3% behind the 72h; 24h～72h after 1000 times of dispensers, corrected mortality are between 35.0%～65.0%, and the food refusal rate is 71.2% behind the 72h; 24h～72h after 2000 times of dispensers, corrected mortality are between 17.5%～57.5%, and the food refusal rate is 51.7% behind the 72h.
Embodiment 4:
To contain 79% benzoyl gland analog derivative (I-4) preparation is diluted to 500 times, 1000 times, 2000 times respectively and makes concentration and handle, the object crop is the wild cabbage of group's phase, for examination worm source is small cabbage moth 1～2 instar larvae, adopt leaf dish method, 24h, 48h, 72h investigate diamondback moth larvae survival number respectively behind medicine; And get the food area in 72h investigation.Drug effect result shows: contain 24h～72h after 500 times of dispensers of benzoylureas analog derivative (I-4) of 65%, corrected mortality is between 57.5%～85.0%, and the food refusal rate is 92.2% behind the 72h; 24h～72h after 1000 times of dispensers, corrected mortality are between 47.5%～72.5%, and the food refusal rate is 81.2% behind the 72h; 24h～72h after 2000 times of dispensers, corrected mortality are between 35.0%～62.5%, and the food refusal rate is 63.0% behind the 72h.
Embodiment 5:
To contain 55% benzoylureas analog derivative (I-5) preparation is diluted to 500 times, 1000 times, 2000 times respectively and makes concentration and handle, the object crop is the wild cabbage of group's phase, for examination worm source is small cabbage moth 1～2 instar larvae, adopt leaf dish method, 24h, 48h, 72h investigate diamondback moth larvae survival number respectively behind medicine; And get the food area in 72h investigation.Drug effect result shows: contain 24h～72h after 500 times of dispensers of benzoylureas analog derivative (I-5) of 65%, corrected mortality is between 45.0%～72.5%, and the food refusal rate is 78.7% behind the 72h; 24h～72h after 1000 times of dispensers, corrected mortality are between 35.0%～62.5%, and the food refusal rate is 62.9% behind the 72h; 24h～72h after 2000 times of dispensers, corrected mortality are between 17.5%～47.5%, and the food refusal rate is 45.3% behind the 72h.
Embodiment 6:
To contain 76% benzoylureas analog derivative (I-6) preparation is diluted to 500 times, 1000 times, 2000 times respectively and makes concentration and handle, the object crop is the wild cabbage of group's phase, for examination worm source is small cabbage moth 1～2 instar larvae, adopt leaf dish method, 24h, 48h, 72h investigate diamondback moth larvae survival number respectively behind medicine; And get the food area in 72h investigation.Drug effect result shows: contain 24h～72h after 500 times of dispensers of benzoylureas analog derivative (I-6) of 76%, corrected mortality is between 52.5%～70.0%, and the food refusal rate is 74.8% behind the 72h; 24h～72h after 1000 times of dispensers, corrected mortality are between 60.0%～57.5%, and the food refusal rate is 48.5% behind the 72h; 24h～72h after 2000 times of dispensers, corrected mortality are between 25.0%～47.5%, and the food refusal rate is 41.2% behind the 72h.
Embodiment 7:
To contain 88.9% benzoylureas analog derivative (I-7) preparation is diluted to 500 times, 1000 times, 2000 times respectively and makes concentration and handle, the object crop is the wild cabbage of group's phase, for examination worm source is small cabbage moth 1～2 instar larvae, adopt leaf dish method, 24h, 48h, 72h investigate diamondback moth larvae survival number respectively behind medicine; And get the food area in 72h investigation.Drug effect result shows: contain 24h～72h after 500 times of dispensers of benzoylureas analog derivative (I-7) of 76%, corrected mortality is between 55.0%～80.0%, and the food refusal rate is 84.9% behind the 72h; 24h～72h after 1000 times of dispensers, corrected mortality are between 40.0%～67.5%, and the food refusal rate is 73.4% behind the 72h; 24h～72h after 2000 times of dispensers, corrected mortality are between 25.0%～55.0%, and the food refusal rate is 63.8% behind the 72h.
Claims (4)
1, new benzoyl urea compound is characterized in that using compound
With compound
Prepared in reaction gets following benzoylureas analog derivative:
The consumption of above-mentioned two compounds is 1: 1.1～1: 1.3, wherein radicals R
1, R
2, R
5Be fluorine atom or chlorine atom; R
3Be fluorine atom or amino; R
4Be hydrogen, chlorine atom or fluorine atom.
2, compound according to claim 1 is characterized in that general structure is
Compound as follows: (a) work as R
1Be F, R
2Be Cl, R
3During for F, R
4Be Cl, R
5Be H; (b) work as R
1Be F, R
2Be Cl, R
3During for F, R
4Be F, R
5Be F.(c) work as R
1Be F, R
2Be Cl, R
3During for F, R
4Be Cl, R
5Be Cl.(c) work as R
1Be F, R
2Be Cl, R
3Be NH
2The time, R
4Be Cl, R
5Be H.(d) work as R
1Be F, R
2Be Cl, R
3Be NH
2The time, R
4Be F, R
5Be F.(e) work as R
1Be Cl, R
2Be Cl, R
3During for F, R
4Be Cl, R
5Be H.(f) work as R
1Be Cl, R
2Be Cl, R
3Be NH
2The time, R
4Be Cl, R
5Be H.(g) work as R
1Be Cl, R
2Be Cl, R
3Be NH
2The time, R
4Be F, R
5Be F.(h) work as R
1Be F, R
2Be F, R
3During for F, R
4Be Cl, R
5Be H.(i) work as R
1Be F, R
2Be F, R
3During for F, R
4Be F, R
5Be F.(j) work as R
1Be F, R
2Be F, R
3During for F, R
4Be Cl, R
5Be Cl.(k) work as R
1Be F, R
2Be F, R
3Be NH
2The time, R
4Be Cl, R
5Be H.(1) works as R
1Be F, R
2Be F, R
3Be NH
2The time, R
4Be F, R
5Be F.(m) work as R
1Be F, R
2Be F, R
3Be NH
2The time, R
4Be Cl, R
5Be Cl.
3, compound according to claim 2 is characterized in that the compound of said structure general formula is:
Work as R
1Be F, R
2Be F, R
3During for F, R
4Be Cl, R
5Be H.
Work as R
1Be F, R
2Be F, R
3During for F, R
4Be F, R
5Be F.
Work as R
1Be F, R
2Be F, R
3Be NH
2The time, R
4Be Cl, R
5Be Cl.
4, the insecticidal ovicide of compound benzoylureas analog derivative according to claim 1 is characterized in that: R wherein
1, R
2, R
5Be fluorine atom or chlorine atom; R
3Be fluorine atom or amino; R
4Be hydrogen, chlorine atom or fluorine atom.
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| CN 02113831 CN1203054C (en) | 2002-06-04 | 2002-06-04 | Novel benzoylurea compound and use thereof |
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| CN1203054C CN1203054C (en) | 2005-05-25 |
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| CN106336395A (en) * | 2016-07-28 | 2017-01-18 | 浙江工业大学 | Benzamide derivatives containing urea bridge and preparation method and application thereof |
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| CN106336395A (en) * | 2016-07-28 | 2017-01-18 | 浙江工业大学 | Benzamide derivatives containing urea bridge and preparation method and application thereof |
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| CN1203054C (en) | 2005-05-25 |
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