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CN1552704A - Dibenzocyclooctane carboxylic ether compounds with herbicidal activity - Google Patents

Dibenzocyclooctane carboxylic ether compounds with herbicidal activity Download PDF

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CN1552704A
CN1552704A CNA031333788A CN03133378A CN1552704A CN 1552704 A CN1552704 A CN 1552704A CN A031333788 A CNA031333788 A CN A031333788A CN 03133378 A CN03133378 A CN 03133378A CN 1552704 A CN1552704 A CN 1552704A
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alkyl
compound
halogen
chlorine
follows
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CN1296366C (en
Inventor
斌 李
李斌
相东
马宏娟
张宗俭
刘振龙
王世辉
徐龙鹤
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Shenyang Research Institute of Chemical Industry Co Ltd
Sinochem Corp
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Shenyang Research Institute of Chemical Industry Co Ltd
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Abstract

A dibenzocyclooctalkyl carboxylate compound with herbiciding activity and its composition can be used to effectively control the mono-and di-cotyledonous weeds.

Description

Dibenzocyclooctane yl carboxylic acid ester compound with weeding activity
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 dibenzo-1,3-two oxa-s-cyclooctane-2-carboxylic acid ester compound is as medicine (J.Medicinal Chemistry, 15,1273-1278 (1972)), the existing report of weedicide (USP 4938790).But as two carboxyl ester compounds shown in the present are not seen open.
Summary of the invention
The invention provides a kind of dibenzo-1 of novel structure, 3-two oxa-s-cyclooctane-2-carboxylic acid ester compound.
Shown in general formula (I):
Figure A0313337800051
Wherein:
n＝1-8；
R is selected from (C 1-C 4) alkyl or substituted radical Q1, Q2 or Q3 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 6, 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:
n＝1-8；
R is selected from (C 1-C 4) alkyl or substituted radical Q1, Q2 or Q3 as follows:
Figure A0313337800062
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:
Figure A0313337800063
Wherein: R 5, R 6Be selected from H or chlorine;
R 10Be selected from H, halogen, CN or NO 2
And steric isomer.
Further preferred compound is in the general formula (I) among the present invention:
n＝1-6；
R is selected from (C 1-C 4) alkyl, or substituted radical Q2 or Q3 as follows:
Figure A0313337800071
Wherein: 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:
The preparation of compound (II) is referring to (J.Medicinal Chemistry, 15,1273-1278 (1972)).
Compound (II) 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 (II-1) for-10 ℃ in 0.5-48 hour to the following reaction of boiling point.
Acyl chlorides (II-1) and alkane glycol (can by buying on the market) be in The suitable solvent, and temperature is reacted down to boiling point and to be made compound (II-2) in 0.5-48 hour for-10 ℃.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 (RCOCl) 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.
Acyl chlorides (RCOCl) can have been bought by market, or is obtained by the preparation method of acyl chlorides (II-1) by the commercially available RCOOH in market.
Table 1: the The compounds of this invention of part shown in general formula I
Figure A0313337800081
Compound n R mp (℃)
11 CH 3Oily matter
22 CH 3Oily matter
33 CH 3Oily matter
44 CH 3Oily matter
51 C 2H 5Oily matter
62 C 2H 5Oily matter
73 C 2H 5Oily matter
84 C 2H 5Oily matter
91 Q1 (R 1=R 2=H) oily matter
10 2 Q1 (R 1=R 2=H) oily matter
11 3 Q1 (R 1=R 2=H) oily matter
12 4 Q1 (R 1=R 2=H) oily matter
13 1 Q1 (R 1=NO 2, R 2=(2-Cl-4-CF 3) phenoxy group) oily matter
14 1 Q2 (R 3=Cl, R 4=H, A=Cl) oily matter
15 1 Q2 (R 3=H, R 4=CH 3, A=A1 (R 5=2-Cl, R 6=4-Cl)) oily matter
16 2 Q2 (R 3=H, R 4=CH 3, A=A1 (R 5=2-Cl, R 6=4-Cl)) oily matter
17 1 Q2 (R 3=H, R 4=CH 3, A=A 4(R 10=6-Cl)) oily matter
18 1 Q3 oily matter
19 2 Q3 oily matter
20 3 Q3 oily matter
21 4 Q3 oily matter
Part of compounds in the table 1 1H NMR (Mercury 300 nuclear magnetic resonance analyser, CDCl 3) data are as follows:
Compound 1:
7.351-7.321(q，2H)，7.198-7.048(m，6H)，5.109(s，1H)，4.638-4.596(d，1H)，4.587-4.556(q，2H)，4.450-4.419(q，2H)，3.508-3.466(d，1H)，2.119(s，3H)
Compound 2:
7.351-7.320(m，2H)，7.193-7.047(m，6H)，5.120(s，1H)，4.636-4.595(d，1H)，4.544-4.512(m，2H)，4.275-4.244(m，2H)，3.879-3.847(m，2H)，3.793-3.762(m，2H)，3.509-3.466(d，1H)，2.072(S，3H)
Compound 3:
7.345-7.315(m，2H)，7.183-7.044(m，6H)，5.110(s，1H)，4.633-4.590(d，1H)，4.538-4.506(m，2H)，4.230-4.198(m，2H)，3.880-3.847(m，2H)，3.759-3.669(m，6H)，3.503-3.461(d，1H)，2.051(s，3H)
Compound 4:
7.348-7.318(q，2H)，7.192-7.047(m，6H)，5.109(s，1H)，4.634-4.592(d，1H)，4.535-4.503(m，2H)，4.217-4.186(m，2H)，3.877-3.845(m，2H)，3.756-3.624(m，10H)，3.504-3.462(d，1H)，2.066(S，3H)
Compound 5:
7.352-7.323(q，2H)，7.256-7.047(m，6H)，5.105(s，1H)，4.638-4.592(d，1H)，4.580-4.561(m，2H)，4.453-4.430(m，2H)，3.508-3.466(d，1H)，2.437-2.362(q，2H)，1.190-1.139(t，3H)
Compound 6:
7.350-7.319(m，2H)，7.192-7.044(m，6H)，5.118(s，1H)，4.636-4.594(d，1H)，4.540-4.508(q，2H)，4.283-4.252(t，2H)，3.878-3.846(q，2H)，3.793-3.762(t，2H)，3.508-3.466(d，1H)，2.366-2.315(q，2H)，1.146-1.096(t，3H)
Compound 7:
7.343-7.314(m，2H)，7.188-7.043(m，6H)，5.109(s，1H)，4.632-4.590(d，1H)，4.535-4.503(t，2H)，4.239-4.207(t，2H)，3.877-3.845(t，2H)，3.748-3.672(m，6H)，3.502-3.460(d，1H)，2.365-2.289(q，2H)，1.254-1.019(t，3H)
Compound 8:
7.347-7.317(q，2H)，7.191-7.047(m，6H)，5.109(s，1H)，4.634-4.592(d，1H)，4.534-4.502(m，2H)，4.227-4.194(m，2H)，3.875-3.843(m，2H)，3.748-3.631(m，10H)，3.503-3.462(d，1H)，2.384-2.309(q，2H)，1.154-1.104(t，3H)
Compound 9:
8.103-8.075(m，1H)，7.551-7.538(m，2H)，7.471-7.420(m，2H)，7.335-7.314(m，2H)，7.117-6.990(6H)，5.114(s，1H)，4.734-4.683(4H)，4.627-4.584(d，1H)，3.494-3.452(d，1H)
Compound 10:
8.047-8.016(m，2H)，7.566-7.471(m，3H)，7.379-7.311(m，2H)，7.135-7.021(m，6H)，5.082(s，1H)，4.618-4.576(d，1H)，4.558-4.498(m，4H)，3.931-3.896(m，4H)，3.490-3.448(d，1H)
Compound 11:
8.053-8.024(m，1H)，7.563-7.512(m，2H)，7.440-7.390(m，2H)，7.335-7.305(q，2H)，7.177-7.038(m，6H)，5.097(s，1H)，4.625-4.583(d，1H)，4.514-4.458(m，4H)，3.875-3.837(m，4H)，3.755-3.743(m，4H)，3.492-3.450(d，1H)
Compound 12:
8.072-8.033(m，1H)，7.575-7.501(m，2H)，7.471-7.401(m，2H)，7.385-7.334(q，2H)，7.184-7.043(m，6H)，5.101(s，1H)，4.630-4.587(d，1H)，4.517-4.441(m，4H)，3.854-3.792(m，4H)，3.723-3.664(m，8H)，3.496-3.453(d，1H)
Compound 15:
7.420-6.708(m，15H)，5.083(s，1H)，4.757-4.732(q，1H)，4.595-4.552(d，1H)，4.599-4.543(m，4H)，3.489-3.446(d，1H)，1.673-1.639(3H)
Compound 16:
7.415-6.700(m，15H)，5.081(s，1H)，4.781-4.751(q，1H)，4.594-4.551(d，1H)，4.602-4.556(m，8H)，3.484-3.441(d，1H)，1.666-1.643(d，3H)
Compound 17:
8.612(s，1H)，8.043(s，1H)，7.668-7.591(m，3H)，7.317-6.940(m，12H)，5.079(s，1H)，4.849-4.826(q，1H)，4.644-4.601(d，1H)，4.590-4.559(m，4H)，3.471-3.428(d，1H)，1.696-1.674(d，3H)
Compound 18:
7.328-7.297(q，4H)，7.094-7.065(m，12H)，5.144(s，2H)，4.73(s，4H)，4.626-4.584(d，2H)，3.487-3.445(d，2H)
Compound 19:
7.317-7.286(q，4H)，7.105-7.063(m，12H)，5.108(s，2H)，4.586-4.545(d，2H)，4.562-4.529(t，4H)，3.946-3.914(t，4H)，3.466-3.423(d，2H)
Compound 20:
7.340-7.309(q，4H)，7.127-7.044(m，12H)，5.123(s，2H)，4.625-4.582(d，2H)，4.554-4.521(t，4H)，3.878-3.846(t，4H)，3.738-3.706(t，4H)，3.501-3.458(d，2H)
Compound 21:
7.335-7.305(q，4H)，7.188-7.037(m，12H)，5.095(s，2H)，4.623-4.581(d，2H)，4.505-4.473(q，4H)，3.841-3.808(q，4H)，3.720-3.708(m，8H)，3.492-3.450(d，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 with general formula (I) compound be 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 the method for management of 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 9 is synthetic in the table 1:
In the reaction flask of 150ml, drop into II (7.5 grams, 0.0335mol), methylene dichloride (70ml), and oxalyl chloride (6.4 grams, 0.0503mol), absorb tail gas with alkali lye, room temperature reaction 30 minutes adds 2 DMF, has a large amount of gases to emit again, stopped reaction after 2 hours, reaction solution concentrating under reduced pressure get 5.6 gram oily matter II-1.
In the reaction flask of 50ml, add II-1 (1.0 grams, 0.00365mol) and the 10ml methylene dichloride, stir well the back add ethylene glycol (2.2 grams, 0.0365mol), triethylamine (0.44 gram, 0.00365mol), room temperature reaction 2 hours.Reaction solution is poured in the 250ml separating funnel, add the 100ml ethyl acetate, 50ml water, the 50ml saturated sodium bicarbonate aqueous solution is used in layering, ethyl acetate layer successively, and the 50ml saturated sodium-chloride water solution is washed, anhydrous magnesium sulfate drying, concentrating, is ethyl acetate with developping agent: the silica gel column chromatography of sherwood oil=1: 2 separates, 0.35 restrain oily matter II-2.
In the reaction flask of 50ml, add II-2 (0.5 gram, 0.00167mol) and the 10ml methylene dichloride, stir well the back add Benzoyl chloride (0.28 gram, 0.00192mol), triethylamine (0.20 gram, 0.00192mol), room temperature reaction 2 hours.Reaction solution is poured in the 250ml separating funnel, add the 100ml ethyl acetate, 50ml water, the 50ml saturated sodium bicarbonate aqueous solution is used in layering, ethyl acetate layer successively, and the 50ml saturated sodium-chloride water solution is washed, anhydrous magnesium sulfate drying, concentrating, is ethyl acetate with developping agent: the silica gel column chromatography of sherwood oil=1: 2 separates, 0.30 to restrain oily matter be compound 9.
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 (2250 gram/hectare)/seedling (2250 gram/hectare)]
Compound Youth-and-old-age Piemarker Cassia tora The barnyard grass grass The dog tail Lady's-grass
Before the seedling Behind the seedling Before the seedling Behind the seedling Before the seedling Behind the seedling Before the seedling Behind the seedling Before the seedling Behind the seedling Before the seedling Behind the seedling
13* -** - - 80 - - - ?80 ????- ?- ????- ????-
14* - - - 80 - - - ?40 ????- ?- ????- ????-
15 95 100 90 70 80 65 80 ?30 ????80 ?30 ????100 ????25
16 60 100 80 20 75 50 80 ?20 ????95 ?30 ????90 ????40
17 - - 0 30 0 30 100 ?40 ????- ?- ????100 ????65
18 90 100 70 10 80 60 70 ?40 ????75 ?20 ????70 ????40
20 - - 0 100 10 40 40 ?45 ????- ?- ????75 ????15
22 - - 0 100 0 50 10 ?20 ????- ?- ????0 ????0
*: consumption is 1200 gram/hectares
*: "-" expression is not surveyed.
Compound 22 is the compound in the United States Patent (USP) (USP 4938790), and its structural formula is as follows:

Claims (6)

1, a kind of dibenzo-1,3-two oxa-s-cyclooctane-2-carboxylic acid ester compound, shown in general formula (I):
Figure A031333780002C1
Wherein:
n＝1-8；
R is selected from (C 1-C 4) alkyl or substituted radical Q1, Q2 or Q3 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 1) 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:
Figure A031333780002C3
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.
2, according to the described compound of claim 1, in the general formula (I):
n＝1-8；
R is selected from (C 1-C 4) alkyl or substituted radical Q1, Q2 or Q3 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:
Figure A031333780003C2
Wherein: R 5, R 6Be selected from H or chlorine;
R 10Be selected from H, halogen, CN or NO 2
And steric isomer.
3, according to the described compound of claim 2, in the general formula (I):
n＝1-6；
R is selected from (C 1-C 4) alkyl, or substituted radical Q2 or Q3 as follows:
Wherein: 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.
4, a kind of herbicidal composition is characterized in that: it is that active ingredient and agricultural go up acceptable carrier that said composition contains the described general formula of claim 1 (I) compound, and wherein the weight content of active ingredient is 0.1-99%.
5, the described compound of claim 1 or its composition purposes that is used to prevent and kill off single broadleaf weed.
6, the method for a kind of management of 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.
CNB031333788A 2003-05-27 2003-05-27 Dibenzocyclooctane carboxylic ether compounds with herbicidal activity Expired - Fee Related CN1296366C (en)

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Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4938790A (en) * 1989-06-15 1990-07-03 The Dow Chemical Company Herbicidal 12-substituted 12H-dibenzo(D,G)(1,3)dioxocin-6-carboxylic acids
US4976770A (en) * 1989-06-29 1990-12-11 Fermenta Asc Corporation Herbicidal and plant growth regulant activity of glyoxylates
CN1128146C (en) * 2000-07-27 2003-11-19 沈阳化工研究院 Dibenzo-1,3-dioxo-cyclooctane-2-oximino carboxylate compound with herbicidal activity

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