CN1676518B - 4-substituted phenyl pyridazine compound and herbicidal activity - Google Patents

4-substituted phenyl pyridazine compound and herbicidal activity Download PDF

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CN1676518B
CN1676518B CN 200510013207 CN200510013207A CN1676518B CN 1676518 B CN1676518 B CN 1676518B CN 200510013207 CN200510013207 CN 200510013207 CN 200510013207 A CN200510013207 A CN 200510013207A CN 1676518 B CN1676518 B CN 1676518B
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alkyl
phenyl
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alkoxyl
alkylogen
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CN1676518A (en
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杨华铮
许寒
邹小毛
胡方中
刘斌
杨秀凤
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Nankai University
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Abstract

This invention relates to 4-substitued phenyl pyridazine chemical compound and its weed killing reactivity. The chemical compounds (I)(II) have high weed killing reactivity. It can effectively kill the one-year ruderal and broad-leave weed. There after, R1: H, alkyl, alkoxyl, alkylogen, alkylogen oxide, halogen and etc; R2, H, alkyl, alkoxyl, phenyl alkoxyl, hydroxyl phenyl, alkoxyl alkyl, alkylogen, alkylogen alkoxyl, nitryl, cyan, alkyl amine, dialkyl, acetylamino and etc; R3:H, phenyl, hydroxyl phenyl, alkoxyl, alkylogen, halide, alkyl halide and etc; R4: H, benzoxazole, substituted benzoxazole base, benzothiazole and etc; R5: H, alkyl, alkylogen: R6R7: H, alkyl, R6, R7 can be the same or different, n=1 or 2.

Description

4-substituted benzene radical pyridazine compound and weeding activity
Technical field
The present invention relates to 4-substituted benzene radical pyridazine compound and weeding activity.
Background technology
Weedicide and plant hormone function influence or the common metabolism of blocking-up plant comprise photosynthesis, the biosynthesizing of carbohydrate, lipid or amino acid whose formation and special cells integral part.Bleaching herbicide can suppress the synthetic of carotenoid, and they are relevant with the function of carotenoid to the toxic action of plant.
Carotenoid in the chloroplast(id) has dual function, on the one hand in photosynthesis as absorber of light; On the other hand as the protective substance in the photosynthesis.They have obtained some active conditions in the chlorophyllous process by optical excitation.Triplet state chlorophyll and oxygen molecule effect are singlet oxygen with Conversion of energy.Singlet oxygen has very high activity, can near its any molecule of oxidation.Carotenoid can be protected chloroplast(id), but when coloured carotenoid concentration reduced, in the time of for example in the presence of bleaching herbicide, they just can not bring into play provide protection.Directly the result is exactly a photofading, that is to say, degraded chlorophyll also destroys photosynthetic film.Most of coml bleaching herbicides all are the phytoene dehydrogenases that suppress to contain in the oxygen photosynthesis.
First enzyme in the phytoene transformation is a phytoene dehydrogenase, studies show that it is the target of bleaching herbicide.Phytoene dehydrogenase is a complete membranin, it with two identical semi-symmetric phytoene molecules as substrate.Have in the organism that carotenoid forms multiple, the phytoene dehydrogenase of two kinds of different aminoacids sequences is arranged.One type exists in the higher plant body and (also exists in blue bacterium and alginite), another kind of type in bacterium and fungi, the function difference of two kinds of enzymes.Because it is different in the bacterium with the phytoene dehydrogenase in the higher plant, bleaching herbicide has natural resistance, therefore can utilize the biotechnology preferred plant to make it produce resistance to the phytoene dehydrogenase inhibitor, this will be the work of an initiative from now on, (the Sandmann G and Boger P that makes the application of phytoene dehydrogenase inhibitor more extensive, Phytoene desaturase as a target for bleaching herbicides, inHerbicide Activity:Toxicology, Biochemistry and Molecular Biology, ed by Roe RM, Burton JDand Kuhr RJ, IOS Press, Amsterdam, Netherlands.pp 1-10 1997).
Norflurazon is a class phytoene dehydrogenase inhibitor early of exploitation.It is a soil processing herbicide before the bud, is mainly used in and prevents and kill off many annual broadleaf weeds in citrus, cotton, Cranberries, nut, nuts and kernels, soybean, the drupe class garden, also can suppress perennial Gramineae and sedge weed.
Monsanto Company had developed a series of 3-phenyl pyridazine class weedicides in 1999, mechanism of action is the effect that suppresses phytoene dehydrogenase, thereby the structure and the active relation of the synthetic .3-phenyl pyridazine of minimizing carotenoid are as follows: on (1) pyridazine ring alkyl or drawing electron group are arranged; (2) on phenyl ring, a position has trifluoromethyl to replace, as the inhibitor of phytoene dehydrogenase. and the replacement of other position or other group all can reduce activity on the phenyl ring; (3) 6 or 4 s' replacement reduces active on the pyridazine ring; (4) variation of 5 bit substituents is influential to activity on the pyridazine ring, and activity was best when wherein substituting group was methoxyl group. and compare with methoxyl group, contain the N of nucleophilic group, S, other substituting groups that O forms have reduced the bleaching weeding activity 5 replacement. when substituting group is OCF 2During H, the isonomic OCH of specific activity 3The compound that replaces is low, but selective to corn.(MichaelS.South J.Heterocyclic Chem.，1999，36，301)
The pyridazine class weedicide reported in the document is most of for phenyl is substituted in 2 and 3 s' compound, and 4-phenyl replacement pyridazine class structure is not appeared in the newspapers in the literature as weedicide.
Summary of the invention
The purpose of this invention is to provide 4-substituted benzene radical pyridazine compound and their preparation method and application.Compound of the present invention has higher weeding activity to annual gramineous weed and broadleaf weeds.
The present invention is (II) compound of following general formula (I):
Wherein,
R 1: H, alkyl, alkoxyl group, haloalkyl, halogenated alkoxy, halogen, alkylthio, halogenated alkylthio, cyano group, nitro;
R 2: H, alkyl, alkoxyl group, phenyl alkoxyl group, hydroxyalkyl, alkoxyalkyl, haloalkyl, halogenated alkoxy, alkylthio, thiazolinyl, haloalkenyl group, carboxyl, alkoxy carbonyl, alkyl amine group carbonyl, dialkyl amino carbonyl, aminocarboxyl, halogen, nitro, cyano group, alkyl amine group, dialkyl amino, kharophen, COR 5, NR 6R 7, 3～6 yuan of heterocycles;
R 3: H, alkyl, hydroxyalkyl, alkoxyalkyl, haloalkyl, thiazolinyl, haloalkenyl group, ester group, alkoxy carbonyl, alkyl amine group carbonyl, dialkyl amino carbonyl, aminocarboxyl, COR 5, SO 2R 5, 3～6 yuan of carbocyclic ring or heterocycles, optional benzyl, the phenyl that replaces;
R 4: benzoxazolyl, benzothiazolyl, phenyl, pyrimidyl, pyrazolyl, pyridazine, pyridyl, substituted pyridinyl, H, alkyl, hydroxyalkyl, alkoxyalkyl, haloalkyl, thiazolinyl, haloalkenyl group, ester group, benzyl, COR 5, SO 2R 5, 3～6 yuan of carbocyclic ring or heterocycles, optional benzoxazolyl, benzothiazolyl, phenyl, pyrimidyl, pyrazolyl, pyridazine, pyridyl, the benzyl that replaces;
R 5: H, alkyl, haloalkyl;
R 6R 7: H, alkyl, R 6, R 7Can be identical, also can be different;
N=1 or 2;
Substituting group on above-mentioned said phenyl ring and the heterocycle is alkyl, alkoxyl group, haloalkyl, halogenated alkoxy, halogen, alkylthio, halogenated alkylthio, cyano group or nitro, and substituting group quantity is 1～5.Above-mentioned alkyl is C 1～C 6Alkyl.
Above-mentioned said R 1Be H ,-m-CF 3,-m-OCH 3,-m-Br ,-m-CH 3,-o-CF 3,-o-OCH 3,-o-Br ,-o-CH 3,-p-CF 3,-p-OCH 3,-p-Br ,-p-CH 3, R 2Be 6-CH 3-, 6-CF 3-, 6-Cl-, 6-Br, 6-CH 3O-, 6-CH 3CH 2O-, 6-CH 3NH-, 6-(CH 3) 2N-, 5-CH 3-, 5-CF 3-, 5-Cl-, 5-Br, 5-CH 3O-, 5-CH 3CH 2O-, 5-CH 3NH-, 5-(CH 3) 2N-, 5,6-di-CH 3, 5,6-di-CF 3, R 3Be-CH 3,-C 2H 5,-CH 2CH 2CH 3, CH (CH 3) 2,-CH 2CH (CH 3) CH 3, CH (CH 3) CH 2CH 3,-CH 2CH=CH 2,-CH 2CH=CHCl ,-CHClCH=CHCl ,-CHClCH=CH 2,-CH 2C ≡ CH ,-CO 2C 2H 5,-CO 2CH 3,-CH 2COOC 2H 5,-CH 2C 6H 5,-CH 2OCH 3,-CH 2CH 2OCH 2CH 3,-SO 2CH 3,-C 6H 5,, R 4Be-CH 3,-C 2H 5,-CH 2CH 2CH 3, CH (CH 3) 2,-CH 2CH 2(CH 3) CH 3,-CH (CH 3) CH 2CH 3,-CH 2CH=CH 2,-CH 2CH=CHCl ,-CHClCH=CHCl ,-CHClCH=CH 2,-CH 2C ≡ CH ,-CO 2C 2H 5,-CO 2CH 3,-CH 2COOC 2H 5,-CH 2C 6H 5,-CH 2OCH 3,-CH 2CH 2OCH 2CH 3,-SO 2CH 3,-C 6H 5, substituted benzene ring, substituted pyrimidines, substituted pyridines, substituted pyrazolecarboxylic, Substituting group on above-mentioned said phenyl ring and the heterocycle is alkyl, alkoxyl group, haloalkyl, halogenated alkoxy, halogen, alkylthio, halogenated alkylthio, cyano group or nitro, and substituting group quantity is 1～5.
The compounds of this invention (I) is synthetic route such as Fig. 2 (II), and concrete synthetic route of the present invention is described in detail as follows:
(1) substituted acyl ethyl propionate and hydrazine hydrate mix, and wherein mol ratio is 1: 1～2, adds a small amount of alcoholic solvent.Mixture was 0～90 ℃ of reaction 0.5～2 hour, and placement is spent the night, and obtains colourless tabular crystal, is 4,5-dihydro-6-replacement-3-pyridazinone.
(2) 4,5-dihydro-6-replacement-3-pyridazinone is dissolved in the solvent Glacial acetic acid, and dropping liquid bromine mol ratio is 1: 1～3, drip off post-heating to 40～100 ℃, reflux to place after 5～60 minutes and spend the night, be the mixture of 6-replacement-3-pyridazinone and hydrogen bromide with the reaction solution suction filtration next day.6-replacement-3-the pyridazinone that makes and the mixture of hydrogen bromide are dissolved in the solvent Glacial acetic acid, and adding the anhydrous sodium acetate mol ratio is 1: 1～3.Reacted 0.5～2 hour mixture heating up to 40～110 ℃.Remove solvent under reduced pressure, resistates joins in the frozen water, suction filtration, and drying obtains white solid.
(3) 6-replacement-3-pyridazinone is dissolved in the solvent anhydrous tetrahydro furan, 0～70 ℃ was reacted 2～7 hours with (replacement) phenyl-magnesium-bromide down.Reactant is through hydrolysis, washing, and drying is spin-dried for solvent after column chromatography for separation, and eluent is an ethyl acetate: sherwood oil obtains 4-(substituted-phenyl)-6-replacement-3-pyridazinone and 4,5-dihydro-4-(substituted-phenyl)-6-replacement-3-pyridazinone.
(4) 4-(substituted-phenyl)-6-replacement-3-pyridazinone and potassium carbonate powder and 2-chlorine are replaced benzoxazoles or 2-chlorine replace benzothiazole or 2-chlorine substituted pyrimidines with mol ratio 1: 1～3: 1～2 at solvent N, react in the N-dimethyl sulfoxide (DMSO).Temperature of reaction is 0～70 ℃, and the reaction times is 1～48 hour.Reaction afterreaction liquid uses column chromatography after organic phase is spin-dried for through neutralization, extraction, drying, obtains solid, for 3-substituted oxy-4-(substituted-phenyl)-6-replaces pyridazine.
(5) add etoh solvent in the reactor, sodium ethylate and 4-(substituted-phenyl)-6-alkyl-3-pyridazinone, mol ratio is 1: 1～2, is stirred to whole dissolvings.Add the halides that 1-2 doubly measures, 0～50 ℃ was reacted 1～48 hour down.Reaction solution is spin-dried for, and resistates uses column chromatography, and obtaining solid or liquid is that N-replacement-4-substituted-phenyl-6-replaces pyridazinone.
Described application of compound as bleaching herbicide, can be prevented and kill off annual gramineous weed and broadleaf weeds.
The synthetic 4-substituted benzene radical pyridazine compound that obtains of the present invention was not reported in the literature, was brand-new compound; As bleaching herbicide, this class formation also is brand-new simultaneously.Relatively finding the back with commercial bleaching herbicide diflufenican, some compound of the present invention in barnyard grass grass and the little agar diffusion method of rape under the 10ppm albefaction effect to be higher than commercialization kind diflufenican.The present invention can be used as the weedicide of annual gramineous weed and broadleaf weeds.
Description of drawings
Fig. 1 is (II) general formula of The compounds of this invention (I)
Fig. 2 is (II) synthetic route of The compounds of this invention (I)
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.
Embodiment 1:4,5-dihydro-6-methyl-3-pyridazinone
Ethyl levulinate 42.3g and hydrazine hydrate 27.9g mix, and add small amount of ethanol and obtain uniform solution.Mixture heating up is to boiling, and the 1 hour postcooling that refluxes is to room temperature, and placement is spent the night, and obtaining colourless tabular crystal is 4,5-dihydro-6-methyl-3-pyridazinone, productive rate 96%.
Embodiment 2:6-methyl-3-pyridazinone
With 4,5-dihydro-6-methyl-3-pyridazinone 55g is dissolved among the Glacial acetic acid 120ml of new steaming, slowly splashes into liquid bromine 33ml, drip off post-heating to refluxing, place behind the backflow 15min and spend the night, obtain the mixture of 6-methyl-3-pyridazinone and hydrogen bromide with the reaction solution suction filtration next day.6-methyl-3-the pyridazinone that makes and the mixture 22.4g of hydrogen bromide are dissolved in the 85ml Glacial acetic acid, add anhydrous sodium acetate 13.5g, mixture heating up is to boiling, backflow 1h.The solvent underpressure distillation is removed, and resistates joins in the frozen water, obtains white solid, suction filtration, and drying obtains white solid 12.9g, productive rate 80%.
Embodiment 3:4-(3-trifluoromethyl)-6-methyl-3-pyridazinone
10mmol 6-methyl-3-pyridazinone is dissolved in the 50ml anhydrous tetrahydro furan, adds the tetrahydrofuran solution of the 3-trifluoromethyl magnesium bromide of 40mmol under the room temperature.Mixture heating up is to boiling, reflux after 5 hours with saturated ammonium chloride solution hydrolysis, organic phase is washed with saturated nacl aqueous solution, dry, use column chromatography after being spin-dried for solvent, eluent is an ethyl acetate: sherwood oil obtains 4-(3-trifluoromethyl)-6-methyl-3-pyridazinone and 4,5-dihydro-4-(3-trifluoromethyl)-6-methyl-3-pyridazinone, productive rate is respectively 38.58% and 16.89%.
The preparation of embodiment 4:3-benzoxazoles oxygen base-4-(3-trifluoromethyl)-6-methyl pyridazine
With 0.5mmol 4-(3-trifluoromethyl)-6-methyl-3-pyridazinone, the potassium carbonate powder of 0.6mmol porphyrize and DMSO5ml room temperature (25 ℃) stirred 0.5 hour.The DMSO solution 10ml that adds 0.5mmol 2-chlorobenzene and oxazole then, 25 ℃ were reacted 7 hours down.Reaction solution is neutralized with 5% dilute hydrochloric acid, use extracted with diethyl ether, saturated sodium bicarbonate solution washing organic phase, anhydrous magnesium sulfate drying.Organic phase uses column chromatography after being spin-dried for, and eluent is an ethyl acetate: sherwood oil obtains white solid, productive rate 54%
Embodiment 5:2,6-methyl 4-(3-trifluoromethyl)-3-pyridazinone
Add ethanol 5ml in the exsiccant reactor, contain the ethanolic soln solution of 1mmol sodium ethylate, add 4-(3-trifluoromethyl)-6-methyl-3-pyridazinone 1mmol behind the stirring 5min, be stirred to whole dissolvings.Add methyl iodide 1mmol, 15 ℃ were reacted 12 hours down.Reaction solution is spin-dried for, and resistates uses column chromatography, and eluent is an ethyl acetate: sherwood oil obtains white solid, productive rate 74%
Synthesized compound (I) (II) according to similar method, all compounds are through nuclear-magnetism, and ultimate analysis is proved conclusively.Part of compounds has been done infrared.Concrete outcome sees Table 1,2
Table 1 compound (I) Physical properties characterize
No. R 1 R 2 R 3 State (mp ℃)
1 m-CF 3 CH 3 CH 2COOC 2H White powder (80-81)
2 m-CF 3 CH 3 CH 3 White powder
3 m-CF 3 CH 3 CH 2CH＝CH 2 Light yellow thick liquid
4 m-CF 3 CH 3 CH 2C 6H 5 Light yellow thick liquid
5 m-CF 3 CH 3 C 2H 5 Light yellow thick liquid
6 m-CF 3 CH 3 CH 2CH 2CH 3 Light yellow thick liquid
7 m-CF 3 CH 3 CH 2CH 2(CH 3)CH 3 Light yellow thick liquid
8 m-CF 3 CH 3 CO 2C 2H 5 Light yellow thick liquid
9 m-CF 3 CH 3 H White powder (175-176)
10 m-OMe CH 3 H White powder (150-152)
Table 2 compound (II)
Figure G2005100132073D00061
Physical properties characterize
Table 3 compound (I)
Figure G2005100132073D00063
1HNMR composes data
No. 1HNMR(δ，CDCl 3)
1 1.28-1.33(3H，t，J H＝7.2Hz)，2.41(3H，s)，4.25-4.28(2H，d，J H＝7.2Hz)， 4.91(2H，s)，7.29(1H，s)，7.53-7.59(1H，t，J H＝7.8Hz)，7.67-7.69(1H，d，J H＝7.8Hz)， 8.00-8.03(1H，d，J H＝8.4Hz)，8.041(1H，s)
2 2.39(3H，s)，3.83(3H，s)，7.25(1H，s)，7.54-7.58(1H，t，J H＝7.8Hz)， 7.66-7.68(1H，d，J H＝8.0Hz)，8.00-8.02(1H，d，J H＝8.0Hz)，8.03(1H，s)
3 2.39(3H，s)，4.79-4.81(2H，d，J H＝6.0Hz)，5.24-5.31(2H，t，J H＝14.4Hz)， 5.99-6.05(1H，m)，7.24(1H，s)，7.52-7.56(1H，t，J H＝7.8Hz)， 7.64-7.66(1H，d，J H＝7.6Hz)，7.98-8.00(1H，d，J H＝7.6Hz)，8.03(1H，s)
4 240(3H，s)，5.36(2H，s)，7.21(1H，s)，7.28-7.35(3H，m)，7.48-7.49(2H，m)， 7.52-7.56(1H，t，J H＝6.0Hz)，7.64-7.66(1H，d，J H＝8.0Hz)，7.99-7.80(2H，m)
No. 1HNMR(δ，CDCl 3)
5 1.39-1.42(3H，t，J H＝7.2Hz)，2.40(3H，s)，4.23-4.28(2H，m)，7.22(1H，s)， 7.53-7.57(1H，t，J H＝7.8Hz)，7.65-7.67(1H，d，J H＝7.6Hz)， 7.99-8.01(1H，d，J H＝7.6Hz)，8.03(1H，s)
6 0.96-1.00(3H，t，J H＝7.4Hz)，1.83-1.89(2H，m)，2.39(3H，s)， 4.14-4.17(2H，t，J H＝7.6Hz)，7.22(1H，s)，7.52-7.56(1H，t，J H＝7.8Hz)， 7.64-7.66(1H，d，J H＝7.6Hz)，7.99-8.01(1H，d，J H＝8.0Hz)，8.04(1H，s)
7 0.97(3H，s)，0.98(3H，s)，1.64-1.75(3H，m)，2.39(3H，s)，4.19-4.23(2H，t，J H＝7.4Hz)， 7.21(1H，s)，7.53-7.56(1H，t，J H＝7.6Hz)，7.65-7.66(1H，d，J H＝7.6Hz)， 7.99-8.02(2H，m)
8 1.44-1.48(3H，t，J H＝7.2Hz)，2.44(3H，s)，4.52-4.57(2H，m)，7.23(1H，s)， 7.55-7.59(1H，t，J H＝7.8Hz)，7.69-7.71(1H，d，J H＝8.0Hz)， 7.96-7.98(1H，d，J H＝8.0Hz)，7.99(1H，s)
9 2.42(3H，s)，7.317(1H，s)，7.57-7.60(1H，t，J H＝7.8Hz)，7.68-7.70(1H，d，J H＝7.6Hz)， 8.02(1H，s)，8.09-8.11(1H，d，J H＝7.6Hz)，11.77(1H，s)
10 2.38(3H，s)，3.85(3H，s)，6.94-6.99(2H，m)，7.35-7.40(3H，m)，11.21(1H，s)
Table 4 compound (II)
Figure G2005100132073D00071
1HNMR composes data
No. 1HNMR(6，CDCl 3)
11 2.53(3H，s)，7，37(1H，s)，7.38-7.46(2H，m)，7.58-7.65(2H，m)，7.72-7.75(1H，d，J H＝7.8Hz)， 7.83-7.86(1H，m)，8.04-8.07(1H，d，J H＝7.8Hz)，8.106(1H，s)
12 2.53(3H，s)，7.37(1H，s)，7.39-7.43(1H，m)，7.61-7.64(2H，m)，7.73-7.77(2H，m) 8.03-8.06(1H，d，J H＝7.8Hz)，8.094(1H，s)
13 2.516(6H，s)，7.22-7.24(1H，d，J H＝8.1Hz)，7.36(1H，s)，7.42(1H，s)， 7.57-7.63(1H，t，J H＝7.95Hz)，7.69-7.74(2H，m)，8.04-8.06(1H，d，J H＝8.1Hz)，8.10(1H，s)
14 2.52(1H，s)，7.34(1H，s)，7.58-7.63(1H，t，J H＝7.8Hz)，7.72-7.75(1H，d，J H＝7.8Hz)， 7.82-7.84(1H，d，J H＝5.4Hz)，7.97-7.99((1H，d，J H＝7.8Hz)，8.022(1H，s)， 8.77-8.78(1H，d，J H＝5.4Hz)
15 2.68(3H，s)，7.41(1H，s)，7.42-7.46(1H，t，d，，J H＝7.4Hz)，7.52-7.56(1H，t，d，，J H＝7.6Hz)， 7.62-7.66(1H，t，d，，J H＝8Hz)，7.75-7.77(1H，d，，J H＝7.6Hz)，7.91-7.93(1H，d，J H＝7.6Hz)， 8.05(2H，s)，8.16-8.18(1H，d，J H＝8Hz)
16 2.705(3H，s)，7.45(1H，s)，7.65-7.69(1H，t，d，，J H＝8Hz)，7，78-7.80(1H，d，J H＝7.6Hz)， 8.05(2H，s)，8.23-8.25(1H，d，J H＝9.2Hz)，8.39-8.42(1H，m)8.87(1H，d，J H＝2.0Hz)
Embodiment 6: the primary dcreening operation of weeding activity is measured
The little agar diffusion method of barnyard grass grass: add a filter paper in the beaker of the 50ml of covering one deck granulated glass sphere, add 5 milliliters of certain density test compound solution, 10 of the barnyard grass grass seeds that sowing shows money or valuables one carries unintentionally, under 25 ± 1 ℃, illumination 12 hours, under dark 12 hours the culture system, cultivate and measure plant height, root length, fresh weight and range estimation albefaction rate after 7 days. by compound the growth-inhibiting and the albefaction effect of barnyard grass grass are come the weeding activity of detection compound.
The little agar diffusion method of rape; Add a filter paper in the beaker of the 50ml of covering one deck granulated glass sphere, add 5 milliliters of certain density test compound solution, 10 of the Semen Brassicae campestriss that sowing shows money or valuables one carries unintentionally, under 25 ± 1 ℃, illumination 12 hours, under dark 12 hours the culture system, cultivate to measure after 7 days to cultivate and measure plant height, root length, fresh weight and range estimation albefaction rate after 7 days.。By compound the growth-inhibiting and the albefaction effect of rape are come the weeding activity of detection compound.
Table 5 part of compounds (I) weeding activity (II)
Figure G2005100132073D00091
Annotate: albefaction degree and rape plant height, the long inhibiting rate grade scale of root:
Below the A:85-100% B:70-84% C:55-69% D:40-54% E:40%
A1：85-90％ A2：90-95％ A3：95-100％.

Claims (3)

1. 4-substituted benzene radical pyridazine compound is characterized in that the compound of its general formula for (I):
Wherein,
R 1: haloalkyl;
R 2: substituent position is 6 on a pyridazine ring, and substituent type is: alkyl; N=1;
R 3: H, alkyl, thiazolinyl, ester group, alkoxy carbonyl, benzyl;
Said alkyl is C 1～C 6Alkyl.
2. compound according to claim 1 is characterized in that said R 1Be-m-CF 3, R 2Be 6-CH 3-, R 3Be-CH 3,-C 2H 5,-CH 2CH 2CH 3,-CH 2CH (CH 3) CH 3,-CH 2CH=CH 2,-CO 2C 2H 5,-CH 2COOC 2H 5,-CH 2C 6H 5
3. the described application of compound of claim 1 is characterized in that, as bleaching herbicide, can prevent and kill off annual gramineous weed and broadleaf weeds.
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