CN102875540A - Weeding activity of 2-benzoxazinone-5-cyclohexylaminocarbonyltetrazolylone - Google Patents
Weeding activity of 2-benzoxazinone-5-cyclohexylaminocarbonyltetrazolylone Download PDFInfo
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- CN102875540A CN102875540A CN2012104222191A CN201210422219A CN102875540A CN 102875540 A CN102875540 A CN 102875540A CN 2012104222191 A CN2012104222191 A CN 2012104222191A CN 201210422219 A CN201210422219 A CN 201210422219A CN 102875540 A CN102875540 A CN 102875540A
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- weeding activity
- benzoxazinone
- ketone
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- methyl
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Abstract
The invention relates to weeding activity of 2-benzoxazinone-5-cyclohexylaminocarbonyltetrazolylone,Wherein R1 is CH3 and C2H5; R2 is CH3, C2H5, CH2CH=CH2 and propargyl group; and R3 is F and Cl.When 1500g of weedicide per hectare is applied, the weedicide has broad spectrum for cockspur grass, crab grass, amaranth and rape before and after seedling.
Description
(1) technical field
The present invention relates to the weeding activity of 2-benzoxazine ketone group-5-carbonyl amino-cyclohexanone tetrazole ketone.
(2) background technology
Weedicide is the pesticide species that current social is the most widely used and usage quantity is maximum, wherein heterocycle herbicide because have that selectivity is good, activity is high, consumption is few, the characteristics at the bottom of the toxicity, more and more be subject to people's attention.Weedicide exploitation take tetrazole ketone as parent nucleus is another key areas of weedicide exploitation.This type of weedicide has efficiently, low toxicity, succession crop is waited safely advantage, can make its weeds spectrum and crops selectivity generation great variety by the substituting group that changes it, is the very promising agricultural chemicals of a class.
Nineteen ninety, the people such as Theodoridis (Pestic Sci, 1990,30:259-274.) to have reported 2-aryl-5-substituted alkyl tetrazole ketone derivative be the new highy potent herbicide of a class, can use before bud or behind the bud, part of compounds just can be controlled all broadleaf weedss admirably at per hectare 30 grams, and to wheat, soybean, corn and paddy rice demonstrate the crop tolerance, to wheat and fully not injury of soybean.And when the latter used behind bud, per hectare 15 grams just can be controlled broadleaf weeds, and wheat and maize is demonstrated tolerance.
People (the Nippon Noyaku Gakkaishi 2002 such as the people such as Cyrill (WO 9907702) and Yanagi, 27 (2), 199-209.) reported the weeding activity of 2-Chloro-O-Phenyl-5-substituted aminocarbonyl tetrazole ketone compound, part of compounds shows good weeding activity, in the situation that per hectare 150 gram formulation rates can well suppress the growth of weeds.Other document such as EP 732326, EP571855, EP 571854, EP 572855, and EP 672663, and EP 202929, EP 146279, and WO 9825912, EP 764642, EP 612735 have also reported the weeding activity of the 2-aryl of similar structures-5-substituted aminocarbonyl tetrazole ketone compound.
Document JP 11100371, EP 820994, and EP 733625, and EP 728750 and EP 711761 have reported the weeding activity of 2-replacement fatty group-5-substituted aminocarbonyl tetrazole ketone compound.Part of compounds is in the situation that per hectare 250 gram formulation rates can well suppress the growth of paddy field weed.
Document JP 09110863, EP 771797, and JP 0987281, and JP 09100277 and JP 11180965 have reported respectively the weeding activity of 2-substituted pyrazolecarboxylic or substituted pyrimidyl-5--substituted aminocarbonyl tetrazole ketone compound.Part of compounds is in the situation that per hectare 600 gram formulation rates can well suppress the growth of paddy field weed.
Document US 4909829 and WO 9801431 have also reported respectively 2-quinolizidine morpholine ketone or benzyloxy-5--replaces the tetrazole ketone compound, and part of compounds shows good weeding activity, in the situation that per hectare 2.5 gram formulation rates can suppress fully.
The weeding activity of document WO 20030162902, WO 2002028843, EP 902028, EP 7080972-substituted-phenyl-5-substituted aminocarbonyl tetrazole ketone compound.Part of compounds is in the situation that per hectare 250 gram formulation rates can well suppress the growth of paddy field weed.
Although above-mentioned reported in literature multiple 2, the two weeding activity that replace the tetrazole ketone compound of 5-, but without any 2-benzoxazine ketone group mentioned in the notebook patent particularly-5-carbonyl amino-cyclohexanone tetrazole ketone compound, more without any the weeding activity of putting down in writing particularly these compounds.
(3) summary of the invention
The purpose of this invention is to provide a kind of 2-benzoxazine ketone group-5-carbonyl amino-cyclohexanone tetrazole ketone compounds and its preparation method and application.
The present invention is following general formula (I) compound:
Wherein, R wherein
1=CH
3, C
2H
5R
2=CH
3, C
2H
5, CH
2CH=CH
2And propargyl; R
3=F, Cl.
Most of 2-benzoxazine ketone group among the present invention-5-carbonyl amino-cyclohexanone tetrazole ketone compounds has shown weeding activity.
(4) embodiment
Substantive distinguishing features of the present invention can be embodied from following embodiment, but it should not to be considered as be any limitation of the invention.The compounds of this invention (I) synthetic route is:
Embodiment 1:2-(7-chloro-4-methyl-oxo benzoxazinone-6-yl)-5-cyclohexyl (methyl) aminocarboxyl tetrazole ketone (I-1)
Get in 3mmol 2-(7-chloro-4-methyl-oxo benzoxazinone-6-yl) tetrazole ketone, 3.3mmol cyclohexyl (methyl) the urea chloride input 50mL two-mouth bottle, add 15mLTHF, add again the 10mmol triethylamine after the stirring and dissolving, backflow 5h.In reaction solution impouring saturated ammonium chloride solution, add 50 milliliters of ethyl acetate, tell organic phase, anhydrous Na 2SO4 is dry.Obtain sterling through column chromatography.
Embodiment 2:2-(7-chloro-4-ethyl-oxo benzoxazinone-6-yl)-5-cyclohexyl (methyl) aminocarboxyl tetrazole ketone (I-2)
Get in 3mmol2-(7-chloro-4-methyl-oxo benzoxazinone-6-yl) tetrazole ketone, 3.3mmol cyclohexyl (methyl) the urea chloride input 50mL two-mouth bottle, add 15mLTHF, add again the 10mmol triethylamine after the stirring and dissolving, backflow 5h.In reaction solution impouring saturated ammonium chloride solution, add 50 milliliters of ethyl acetate, tell organic phase, anhydrous Na
2SO
4Dry.Obtain sterling through column chromatography.
Embodiment 2:2-(7-chloro-4-propenyl-oxo benzoxazinone-6-yl)-5-cyclohexyl (methyl) aminocarboxyl tetrazole ketone (I-3)
Get in 3mmol2-(7-chloro-4-methyl-oxo benzoxazinone-6-yl) tetrazole ketone, 3.3mmol cyclohexyl (methyl) the urea chloride input 50mL two-mouth bottle, add 15mL THF, add again the 10mmol triethylamine after the stirring and dissolving, backflow 5h.In reaction solution impouring saturated ammonium chloride solution, add 50 milliliters of ethyl acetate, tell organic phase, anhydrous Na
2SO
4Dry.Obtain sterling through column chromatography.
Embodiment 4:2-(7-fluoro-4-methyl-oxo benzoxazinone-6-yl)-5-cyclohexyl (methyl) aminocarboxyl tetrazole ketone (I-9)
Get in 3mmol 2-(7-fluoro-4-methyl-oxo benzoxazinone-6-yl) tetrazole ketone, 3.3mmol cyclohexyl (methyl) the urea chloride input 50mL two-mouth bottle, add 15mLTHF, add again the 10mmol triethylamine after the stirring and dissolving, backflow 5h.In reaction solution impouring saturated ammonium chloride solution, add 50 milliliters of ethyl acetate, tell organic phase, anhydrous Na
2SO
4Dry.Obtain sterling through column chromatography.
Synthesized compound (I) according to similar method, the physical parameter of compound the results are shown in Table 1.
The physical properties of table 1 compound (I) characterizes
The primary dcreening operation of embodiment 5 weeding activity is measured
Pot-culture method (cauline leaf processing): in the plastics cuvette of diameter 8cm, put into a certain amount of soil, add a certain amount of water, after planting cover certain thickness soil, in greenhouse, cultivate, come up front with plastic covered.After emerging, every day in addition quantitative clear water to keep normal growth.Carrying out the cauline leaf spraying when seedling length to the certain period processes.Treatment dosage is the 1500g/ hectare.Process 21 days " Invest, Then Investigate " results, measure the overground part fresh weight, suppress percentage ratio with fresh weight and represent drug effect.
Pot-culture method (soil treatment): in the plastics cuvette of diameter 8cm, put into a certain amount of soil, add a certain amount of water, after planting cover certain thickness soil, and in dispenser on the same day, then in greenhouse, cultivate, come up front with plastic covered.After emerging, every day in addition quantitative clear water to keep normal growth.Carrying out the cauline leaf spraying when seedling length to the certain period processes.Treatment dosage is the 1500g/ hectare.Process 21 days " Invest, Then Investigate " results, measure the overground part fresh weight, suppress percentage ratio with fresh weight and represent drug effect.
Active graded index: ++ +++: 〉=80%; ++ ++: 60～79%; +++: 40～59%; ++: 20～39%; + :≤19%
Table 2: the weeding activity inhibiting rate (%) of part of compounds (I) (dosage 1500g/ hectare)
Claims (2)
1. 2-benzoxazine ketone group-5-carbonyl amino-cyclohexanone tetrazole ketone compounds is characterized in that it is the compound of general formula (I):
R wherein
1=CH
3, C
2H
5R
2=CH
3, C
2H
5, CH
2CH=CH
2And propargyl; R
3=F, Cl.
2. the application of the described 2-benzoxazine ketone group of claim 1-5-carbonyl amino-cyclohexanone tetrazole ketone compounds is characterized in that weeding activity.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015056811A1 (en) * | 2013-10-17 | 2015-04-23 | 住友化学株式会社 | Tetrazolinone compound and application for same |
| US9822095B2 (en) | 2014-03-28 | 2017-11-21 | Sumitomo Chemical Company, Limited | Tetrazolinone compound and application thereof |
| US9826741B2 (en) | 2014-03-28 | 2017-11-28 | Sumitomo Chemical Company, Limited | Tetrazolinone compound and application thereof |
| US10070646B2 (en) | 2014-03-28 | 2018-09-11 | Sumitomo Chemical Company, Limited | Tetrazolinone compound and application thereof |
Citations (5)
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|---|---|---|---|---|
| US3491092A (en) * | 1963-11-06 | 1970-01-20 | Bayer Ag | Substituted benzoxazinones and a process for their preparation |
| EP0032242A1 (en) * | 1980-01-05 | 1981-07-22 | BASF Aktiengesellschaft | 4H-3,1-benzoxazine derivatives, process for their preparation and their use in inhibiting the growth of unwanted plants |
| CN88100210A (en) * | 1987-01-15 | 1988-07-27 | Fmc有限公司 | Tetrazolinone herbicides |
| EP0334055A2 (en) * | 1988-03-10 | 1989-09-27 | Bayer Ag | Substituted benzoxazinones, several processes and intermediates for their preparation and their use as herbicides |
| CN1195475A (en) * | 1997-01-21 | 1998-10-14 | 拜尔公司 | Selective herbicides based on 1-(2-chloro-phenyl)-4-(N-cyclohexyl-N-ethyl-aminocarbonyl)-1,4-dihydro-5H-tetrazol-5-one and propanil |
-
2012
- 2012-10-30 CN CN2012104222191A patent/CN102875540A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3491092A (en) * | 1963-11-06 | 1970-01-20 | Bayer Ag | Substituted benzoxazinones and a process for their preparation |
| EP0032242A1 (en) * | 1980-01-05 | 1981-07-22 | BASF Aktiengesellschaft | 4H-3,1-benzoxazine derivatives, process for their preparation and their use in inhibiting the growth of unwanted plants |
| CN88100210A (en) * | 1987-01-15 | 1988-07-27 | Fmc有限公司 | Tetrazolinone herbicides |
| EP0334055A2 (en) * | 1988-03-10 | 1989-09-27 | Bayer Ag | Substituted benzoxazinones, several processes and intermediates for their preparation and their use as herbicides |
| CN1195475A (en) * | 1997-01-21 | 1998-10-14 | 拜尔公司 | Selective herbicides based on 1-(2-chloro-phenyl)-4-(N-cyclohexyl-N-ethyl-aminocarbonyl)-1,4-dihydro-5H-tetrazol-5-one and propanil |
Non-Patent Citations (2)
| Title |
|---|
| 李宏伟，等: "N-(7-氟-3-氧-3,4-二氢-2H-苯并[b][1,4]噁嗪-6-基-)-N",N"-二取代脲类化合物的合成及除草活性", 《精细化工中间体》 * |
| 黄明智，等: "N-(7-氟-3-氧-3,4-二氢-苯并[b][1,4]噁嗪-6-基-)乙酰胺类化合物的合成及除草活性", 《农药学学报》 * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015056811A1 (en) * | 2013-10-17 | 2015-04-23 | 住友化学株式会社 | Tetrazolinone compound and application for same |
| JPWO2015056811A1 (en) * | 2013-10-17 | 2017-03-09 | 住友化学株式会社 | Tetrazolinone compounds and uses thereof |
| US10077254B2 (en) | 2013-10-17 | 2018-09-18 | Sumitomo Chemical Company, Limited | Tetrazolinone compound and use thereof |
| US9822095B2 (en) | 2014-03-28 | 2017-11-21 | Sumitomo Chemical Company, Limited | Tetrazolinone compound and application thereof |
| US9826741B2 (en) | 2014-03-28 | 2017-11-28 | Sumitomo Chemical Company, Limited | Tetrazolinone compound and application thereof |
| US10070646B2 (en) | 2014-03-28 | 2018-09-11 | Sumitomo Chemical Company, Limited | Tetrazolinone compound and application thereof |
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