CN1233618C - Benzoylcyclohexanone amine compounds with herbicidal activity - Google Patents
Benzoylcyclohexanone amine compounds with herbicidal activity Download PDFInfo
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- CN1233618C CN1233618C CN 03133377 CN03133377A CN1233618C CN 1233618 C CN1233618 C CN 1233618C CN 03133377 CN03133377 CN 03133377 CN 03133377 A CN03133377 A CN 03133377A CN 1233618 C CN1233618 C CN 1233618C
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Abstract
The present invention relates to an amine-group compound of benzoyl cyclohexanone pimelic ketone with herbicidal activity, which is shown in a general formula (I), wherein R is halogen, CH3SO2 and NO2; Y is halogen, NO2, CH3SO2 and CF3SO2, and Q is substituted or unsubstituted (C1 to C20) alkyl, or substituted or unsubstituted (C6 to C20) phenyl. After the compound and the composition of the present invention are used before seedling emergence or after seedling emergence, various monocotyledonous weeds and dicotyledonous weeds can be effectively prevented and treated.
Description
Technical field
The invention belongs to the weedicide field.
Background technology
Because weedicide or its composition are in use for some time, weeds can produce resistance to it, therefore, need constantly invention novel with improved herbicidal compound and composition.In addition, consider the factor of aspects such as energy economy ﹠ environment, the invention weedicide different with existing herbicide action mechanism also is very important.
Some benzoyl pimelinketone aminated compounds is as the existing report of weedicide (EPA 249813).But as acyl-oxygen alkylamino cyclohexanone analog compound shown in the present is not seen open.
Summary of the invention
The invention provides a kind of benzoyl pimelinketone aminated compounds of novel structure.
Shown in general formula (I):
Wherein:
R is a halogen, CH
3SO
2, NO
2
Y is a halogen, NO
2, CH
3SO
2, CF
3SO
2
Q is (C
1-C
4) alkyl, or substituted radical Q1 or Q2 as follows:
Wherein: R
1Be selected from H, halogen, CN or NO
2
R
2The phenoxy group that is selected from H, halogen or replaces by halogen or haloalkyl;
R
3Be selected from H, halogen or (C
1-C
4) alkyl;
R
4Be selected from H or (C
1-C
4) alkyl;
One of A is selected from H or halogen, or group as follows:
Wherein: R
5, R
6Be selected from H, halogen, (C
1-C
4) alkyl or halo (C
1-C
4) alkyl;
R
7, R
8, R
9, R
10Be selected from H, halogen, CN, NO
2, (C
1-C
4) alkyl or halo (C
1-C
4) alkyl;
And steric isomer.
Comparatively preferred compound is in the general formula (I) among the present invention:
R is a halogen, NO
2
Y is a halogen, NO
2, CH
3SO
2, CF
3SO
2
Q is selected from (C
1-C
4) alkyl or substituted radical Q1 or Q2 as follows:
Wherein: R
1Be selected from H or NO
2
R
2Be selected from H or (2-chloro-4-trifluoromethyl) phenoxy group;
R
3Be selected from H, chlorine or methyl;
R
4Be selected from H or methyl;
One of A is selected from H or chlorine, or group as follows:
Wherein: R
5, R
6Be selected from H or chlorine;
R
10Be selected from H, halogen, CN or NO
2And steric isomer.
Further preferred compound is in the general formula (I) among the present invention:
R is a chlorine, NO
2
Y is a chlorine, NO
2, CH
3SO
2
Q is selected from (C
1-C
4) alkyl or substituted radical Q1 or Q2 as follows:
R
1Be selected from H or NO
2
R
2Be selected from H or (2-chloro-4-trifluoromethyl) phenoxy group;
R
3Be selected from H, chlorine or methyl;
R
4Be selected from H or methyl;
One of A is selected from H or chlorine, or group as follows:
Wherein: R
5Be selected from 2-chlorine;
R
6Be selected from 4-chlorine;
R
10Be selected from 6-chlorine;
And steric isomer.
The alkyl of indication comprises the straight or branched alkyl in the general formula.Alkylhalide group refers to the group that alkyl is replaced by one or more halogen atoms.Halogen refers to fluorine, chlorine, bromine, iodine.
General formula compound of the present invention (I) can be prepared by following method:
Intermediate (II) (can by buying on the market) is dissolved in The suitable solvent with oxalyl chloride, chloroform for example, methylene dichloride, tetracol phenixin, normal hexane, benzene, toluene, ethyl acetate, THF or dioxane, and at organic bases such as triethylamine, under pyridine or the DMF condition as catalyzer, temperature made compound (II-1) for-10 ℃ in 0.5-48 hour to the following reaction of boiling point.
Intermediate (II-1) and thanomin are in The suitable solvent, and temperature made compound (II-2) for-10 ℃ in 0.5-48 hour to the following reaction of boiling point.Solvent can be chloroform, methylene dichloride, tetracol phenixin, hexane, benzene, toluene, ethyl acetate, acetone, DMF, THF or dioxane etc.Add alkaloids, as triethylamine, pyridine, sodium hydroxide, potassium hydroxide, yellow soda ash, salt of wormwood, sodium bicarbonates etc. are to reacting favourable.
Compound (II-2) and acyl chlorides (III) are in The suitable solvent, and temperature made compound (I) for-10 ℃ in 0.5-48 hour to the following reaction of boiling point.Solvent can be chloroform, methylene dichloride, tetracol phenixin, hexane, benzene, toluene, ethyl acetate, acetone, DMF, THF or dioxane etc.Add alkaloids, as triethylamine, pyridine, sodium hydroxide, potassium hydroxide, yellow soda ash, salt of wormwood, sodium bicarbonates etc. are to reacting favourable.
Wherein acyl chlorides (III) can be made by following formula:
Intermediate acid (III-1) (can be by buying on the market, or by " meticulous Organic Chemicals and intermediate handbook, Xu Kexun chief editor, Chemical Industry Press, the method preparation in 1998 in the 3-143 page or leaf) and SOCl
2, oxalyl chloride or PCl
3Be dissolved in The suitable solvent, chloroform for example, methylene dichloride, tetracol phenixin, normal hexane, benzene, toluene, ethyl acetate, THF, or dioxane, and at organic bases such as triethylamine, under pyridine or the DMF condition as catalyzer, temperature made acyl chlorides (III) for-10 ℃ in 0.5-48 hour to the following reaction of boiling point.
Table 1: the The compounds of this invention of part shown in general formula I
| Compound | R | Y | Q | mp(℃) |
| 1 2 3 4 5 6 7 8 9 | Cl Cl Cl Cl Cl Cl Cl NO 2 NO 2 | CH 3SO 2 CH 3SO 2 CH 3SO 2 CH 3SO 2 CH 3SO 2 CH 3SO 2 CH 3SO 2 CH 3SO 2 Cl | CH 3CH 2 Q1(R 1＝R 2＝H) Q2(R 3＝H，R 4＝CH 3，A＝A1(R 5＝2-Cl，R 6＝4-Cl)) Q2(R 3＝Cl，R 4＝H，A＝Cl) Q2(R 3＝CH 3，R 4＝H，A＝Cl) Q1(R 1＝NO 2，R 2＝(2-Cl-4-CF 3) phenoxy group) Q2 (RX=H, R 4＝CH 3，A＝A4(R 10＝6-Cl)) Q2(R 3＝H，R 4＝CH 3，A＝A4(R 10＝6-Cl)) Q2(R 3＝Cl，R 4＝H，A＝Cl) | Grease 166-170 grease grease grease grease grease grease grease |
Part of compounds in the table 1
1H NMR (Mercury 300 nuclear magnetic resonance analyser, CDCl
3) data are as follows:
Compound 1:12.400 (s, 1H), 7.913-7.907 (d, 1H), 7.842-7.810 (q, 1H), 7.280-7.272 (d, 1H), 4.379-4.342 (t, 2H), 3.766-3.721 (q, 2H), 3.071 (S, 3H), 2.765-2.503 (t, 2H), 2.437-2.297 (m, 4H), 2.061-1.972 (t, 2H), and 1.185-1.159 (t, 3H)
Compound 3:12.410 (s, 1H), 7.907-7.901 (d, 1H), 7.832-7.801 (q, 1H), and 7.450-7.441 (d, 1H), 7.279-6.782 (m, 7H), 4.827-4.804 (q, 1H), 4.464-4.431 (t, 2H), 3.745-3.727 (t, 2H), 3.070 (s, 3H), 2.741-2.700 (t, 2H), 2.385-2.341 (t, 2H), 2.043-2.000 (t, 2H), 1.657-1.635 (d, 3H)
Compound 4:12.410 (s, 1H), 7.920-7.915 (d, 1H), 7.849-7.817 (q, 1H), and 7.390-7.382 (d, 1H), 7.272-7.255 (d, 1H), 7.152-7.114 (q, 1H), 6.842-6.813 (d, 1H), 4.782 (s, 2H), and 4.519-4.483 (t, 2H), 3.808-3.771 (q, 2H), 3.075 (s, 3H), 2.761-2.720 (t, 2H), 2.386-2.343 (t, 2H), 2.083-2.009 (t, 2H)
Compound 5:12.410 (s, 1H), 7.918-7.913 (d, 1H), 7.842-7.815 (q, 1H), and 7.295-7.264 (d, 1H), 7.134-7.125 (d, 1H), 7.032-7.002 (q, 1H), 6.652-6.623 (d, 1H), 4.721 (s, 2H), and 4.507-4.471 (t, 2H), 3.768-3.749 (q, 2H), 3.071 (s, 3H), 2.718-2.699 (t, 2H), 2.362-2.340 (t, 2H), 2.247 (s, 3H), 2.045-2.002 (t, 2H)
Compound 6:12.410 (s, 1H), 8.092-7.053 (m, 9H), 4.656-4.621 (t, 2H), 3.887-3.833 (q, 2H), 3.064 (s, 3H), 2.796-2.755 (t, 2H), 2.403-2.361 (t, 2H), 2.049-2.011 (t, 2H)
Compound 7:12.410 (s, 1H), 8.672 (s, 1H), 8.058-7.612 (m, 5H), 7.285-6.951 (m, 5H), 4.866-4.843 (q, 1H), 4.485-4.458 (t, 2H), 3.790-3.771 (q, 2H), 3.057 (s, 3H), 2.758-2.725 (t, 2H), 2.370-2.337 (t, 2H), 2.046-2.010 (t, 2H), 1.710-1.681 (d, 3H)
Compound 8:12.410 (s, 1H), 8.668 (s, 1H), 8.045-7.608 (m, 5H), 7.334-6.952 (m, 5H), 4.899-4.876 (q, 1H), 4.497-4.463 (t, 2H), 3.786-3.767 (q, 2H), 3.120 (s, 3H), 2.761-2.720 (t, 2H), 2.305-2.261 (t, 2H), 2.010-1.967 (t, 2H), 1.643-1.621 (d, 3H)
Compound 9:12.35 (s, 1H), 8.15 (1H), 7.60 (1H), 7.38 (1H), 7.2-6.8 (m, 3H), 4.78 (2H), 4.50 (2H), 3.78 (2H), 2.74 (t, 2H), 2.30 (t, 2H), 1.98 (t, 2H)
General formula of the present invention (I) compound has weeding activity, uses behind Miao Qianmiao and can effectively control single broadleaf weed.Compare with compound of the prior art, have the weeding activity of wide spectrum more, especially monocotyledon weed is had beyond thought high reactivity.
The present invention comprises that also containing with general formula (I) compound is the herbicidal composition of active ingredient.The weight percentage of active ingredient is between 0.1-99% in this herbicidal composition.Comprise also in this herbicidal composition that agricultural goes up acceptable carrier.
Other embodiments of the present invention are method of controlling weeds, and this method comprises herbicidal composition of the present invention is imposed on the surface of growth medium of the places of described weeds or described weeds or described weeds.Usually the comparatively suitable significant quantity of selecting is that per hectare 100 restrains 5000 grams, and preferred significant quantity is that per hectare 200 restrains 3000 grams.
Compound of the present invention can preparation form be administered on soil or the blade face.This compound is dissolved in the carrier usually or is mixed with preparation so that be easier to disperse when using as weedicide.For example: but these chemicals can be made into wet-milling or missible oil.In these compositions, add a kind of liquid or solid carrier at least, and when needing, can mix suitable tensio-active agent.
Use for some, can in herbicidal composition of the present invention, add one or more other weedicide, can produce additional advantage and effect thus.
Compound of the present invention both can use separately also can be mixed together use with other known sterilant, sterilant, weedicide, plant-growth regulator or fertilizer etc.
Should be clear and definite be in claim of the present invention institute restricted portion, can carry out various conversion and change.
Embodiment
The following example, give birth to that the result is tested in test and form can be used to further specify the present invention, but do not mean that restriction the present invention.
Synthetic example
Compound 2 is synthetic in the table 1:
(7 grams 0.021mol) with the 100ml methylene dichloride, stir to add a in the reaction flask of 250ml, the adding oxalyl chloride (5.4 grams, 0.042mol), 3 DMF, stirring at room 4 hours, organic solvent is removed in decompression, adds the 200ml ethyl acetate in the resistates, and ethyl acetate layer is used the 200ml saturated sodium bicarbonate aqueous solution successively, the 200ml saturated sodium-chloride water solution is washed, anhydrous magnesium sulfate drying concentrates, and obtains 5.0 gram yellow solid compound b 1.
(2.3 grams 0.036mol), in the 25ml dichloromethane solution, stir and to drip b1 down (3.2 grams 0.009mol) and the mixed solution of 25ml methylene dichloride, add room temperature reaction 5 hours approximately half an hour to add thanomin in the reaction flask of 250ml.Filter, get 3.1 gram yellow solid c1, MP:164-170 ℃.
The reaction flask of 250ml add d1 (1.22 grams 0.010mol) and the 50ml methylene dichloride, stir, add oxalyl chloride (2.6 grams, 0.020mol), 2 DMF, stirring at room 4 hours, concentrate 1.5 gram yellow liquid e1.
(0.75 restrains, and 0.002mol), (0.2 restrains triethylamine to drop into c1 in the reaction flask of 50ml, 0.002mol), methylene dichloride 10ml stirred 5 minutes, (0.34 gram, 0.0024mol) and the mixed solution of 10ml methylene dichloride, stirring at room is to reacting completely slowly to splash into e1.Pour the 250ml separating funnel in the mixed solution into, add the 50ml ethyl acetate, 50ml water, separatory, ethyl acetate layer are used the 50ml saturated sodium bicarbonate aqueous solution successively, the 50ml saturated sodium-chloride water solution is washed, anhydrous magnesium sulfate drying concentrates, and is ethyl acetate with developping agent: the silica gel column chromatography separation of methyl alcohol=5: 1, get 0.4 gram Off-white solid compound 2, fusing point is 166-170 ℃.
Other compounds in the table 1 can make by above similar method.
Give birth to and survey example
Test before the seedling: after planting carry out, test compound sparges soil surface, handles and is placed on the greenhouse, waters then; Test behind the seedling, seed germination also grew 10-21 days, made the examination material that has a series of growing stages before the processing, selected size, the consistent examination material of growing stage then, handled, and handled to be placed on the greenhouse and to water.The examination material with compound treatment does not compare.The examination material is broadleaf weed youth-and-old-age, piemarker and Cassia tora; Monocotyledon weed barnyard grass grass, dog tail and lady's-grass.
With the former medicine of acetone solution, by design dosage, join in the certain water gaging that contains tensio-active agent, make certain density preparation.Spray with mobile belt atomizer.The examination material is put in spraying rolling in the cupboard and is with, and mobile shower nozzle is sprayed onto medicament on the examination material with the covering of the fan Sprayable through examination material top, identical on nozzle and the common field spray device.Roll band and will try material and shift out outside the cupboard, place loft drier dry.
Examination material after the spraying drying places the greenhouse.Test is from the top water spray before the seedling, and test is poured water from the bottom and kept 48 hours so that water does not touch the blade face behind the seedling.
Handling the back investigated in 4 weeks.Inhibiting rate is total effect of various infringements such as chlorosis, withered spot, retarded growth or the calcination of leaf angle, obtains the result with blank after relatively.Partial test the results are shown in Table 2.
Table 2: the weeding activity of compound in the part general formula I
[before the seedling behind (600 gram/hectare)/seedling (600 gram/hectare)]
| Compound | Youth-and-old-age | Piemarker | Cassia tora | The barnyard grass grass | Gold dog tail | Lady's-grass | ||||||
| Before | After | Before | After | Before | After | Before | After | Before | After | Before | After | |
| 3 | 10 | 0 | 10 | 95 | 100 | 100 | 100 | 100 | 100 | 100 | 100 | 100 |
| 6 | - | 100 | 100 | 100 | 100 | 100 | 98 | 90 | 100 | 100 | 95 | 100 |
| 7 | 100 | 98 | 10 | 100 | 10 | 100 | 100 | 100 | 100 | 100 | 100 | 100 |
| 8 | 100 | 95 | 80 | 100 | 80 | 90 | 100 | 100 | 100 | 100 | 100 | 100 |
"-" expression is not surveyed.
Claims (6)
1, a kind of benzoyl pimelinketone aminated compounds, shown in general formula (I):
Wherein:
R is selected from halogen, CH
3SO
2Or NO
2
Y is selected from halogen, NO
2, CH
3SO
2Or CF
3SO
2
Q is selected from (C
1-C
4) alkyl, or substituted radical Q1 or Q2 as follows:
Wherein: R
1Be selected from H, halogen, CN or NO
2
R
2The phenoxy group that is selected from H, halogen or replaces by halogen or haloalkyl;
R
3Be selected from H, halogen or (C
1-C
4) alkyl;
R
4Be selected from H or (C
1-C
4) alkyl;
One of A is selected from H or halogen, or group as follows:
Wherein: R
5, R
6Be selected from H, halogen, (C
1-C
4) alkyl or halo (C
1-C
4) alkyl;
R
10Be selected from H, halogen, CN, NO
2, (C
1-C
4) alkyl or halo (C
1-C
4) alkyl.
2, according to the described compound of claim 1, in the general formula I:
R is selected from halogen or NO
2
Y is selected from halogen, NO
2, CH
3SO
2Or CF
3SO
2
Q is selected from (C
1-C
4) alkyl or substituted radical Q1 or Q2 as follows:
Wherein: R
1Be selected from H or NO
2
R
2Be selected from H or (2-chloro-4-trifluoromethyl) phenoxy group;
R
3Be selected from H, chlorine or methyl;
R
4Be selected from H or methyl;
One of A is selected from H or chlorine, or group as follows:
Wherein: R
5, R
6Be selected from H or chlorine;
R
10Be selected from H, halogen, CN or NO
2
3, according to the described compound of claim 2, in the general formula I:
R is selected from chlorine or NO
2
Y is selected from chlorine, NO
2Or CH
3SO
2
Q is selected from (C
1-C
4) alkyl or substituted radical Q1 or Q2 as follows:
R
1Be selected from H or NO
2
R
2Be selected from H or (2-chloro-4-trifluoromethyl) phenoxy group;
R
3Be selected from H, chlorine or methyl;
R
4Be selected from H or methyl;
One of A is selected from H or chlorine, or group as follows:
Wherein: R
5Be selected from 2-chlorine;
R
6Be selected from 4-chlorine;
R
10Be selected from 6-chlorine.
4, a kind of herbicidal composition is characterized in that: active ingredient and agricultural that said composition contains general formula (I) compound go up acceptable carrier, and wherein the weight content of active ingredient is 0.1-99%.
5, the described compound of claim 1 purposes that is used to prevent and treat single broadleaf weed.
6, a kind of method of controlling weeds is characterized in that: this method comprises the herbicidal composition as claimed in claim 4 of using herbicidally effective amount on growth medium of these weeds or these weeds or place.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 03133377 CN1233618C (en) | 2003-05-27 | 2003-05-27 | Benzoylcyclohexanone amine compounds with herbicidal activity |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 03133377 CN1233618C (en) | 2003-05-27 | 2003-05-27 | Benzoylcyclohexanone amine compounds with herbicidal activity |
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| Publication Number | Publication Date |
|---|---|
| CN1552693A CN1552693A (en) | 2004-12-08 |
| CN1233618C true CN1233618C (en) | 2005-12-28 |
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ID=34323039
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
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|---|---|
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| CN102718722B (en) * | 2012-07-10 | 2016-02-17 | 南开大学 | The novel fragrant phenoxy ramification of carboxylic esters preparations and applicatio research that a kind of water oil is double molten |
| CN107400058B (en) * | 2016-05-19 | 2019-08-09 | 北京理工大学 | Synthetic method of 2,4,6-trimethylbenzene-1,3,5-triamine and N,N,N-triacylated products |
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