CN1274528A - N-(heterocycloformyl) sulfonamide herbicide - Google Patents
N-(heterocycloformyl) sulfonamide herbicide Download PDFInfo
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- CN1274528A CN1274528A CN 99112943 CN99112943A CN1274528A CN 1274528 A CN1274528 A CN 1274528A CN 99112943 CN99112943 CN 99112943 CN 99112943 A CN99112943 A CN 99112943A CN 1274528 A CN1274528 A CN 1274528A
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Abstract
The N-(heterocycloformul) sulfonamide herbicide and its composition are used in killing weed. It has one heterocycle with substituted C1-C6 alkyl group, C3-C6 alkyne group or C3-C6 epoxy alkyl group, and C1-C6 alkyl group, C1-C6 haloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, nitro group, cyano group or alkoxy carboxyl group.
Description
The invention belongs to the agricultural herbicide field.
Because weed killer herbicide or its composition are in use for some time, weeds can produce resistance to it, therefore, need constantly invention novel with improved herbicides compounds and composition.In addition, consider the factor of aspects such as energy economy ﹠ environment, the invention weed killer herbicide different with existing herbicide action mechanism also is very important.People such as Yoneyama are at Agric.Biol.Chem., and 47, people such as 593-596 (1983) and Takematsu have reported in 257 (on June 5th, 1979) that at US 4,157 the N-benzenesulfonyl benzamide compounds that replaces has activity of weeding.Yet, do not see the report of N-of the present invention (heterocycle formyl) sulfonamide herbicide.
In order to satisfy the requirement on the agricultural, the invention provides acceptable carrier on a kind of new N-(heterocycle formyl) sulfonamide herbicide, its composition, the agricultural, as broad-spectrum herbicide, before bud, use behind the bud and can effectively control single broadleaf weed.The present invention also relates to these compounds of preparation, uses the method that these compounds carry out weeding.
New N-provided by the present invention (heterocycle formyl) sulfonamide compounds is very effective aspect the control weeds, and its general formula is as follows:
In the formula:
W is a heterocycle, comprises pyridine, pyrazine, and pyrimidine, pyridazine, furans and thiophene etc. have halogen (C on the carbonyl ortho position on the ring
1-C
6) the alkyl replacement, and 1-3 the substituting group shown in Z can be arranged,
R is (C
3-C
6) alkynyl group or (C
3-C
6) epoxy alkyl,
N is 0,1,2 or 3, and X is halogen, (C
1-C
6) alkyl, (C
1-C
6) haloalkyl, (C
1-C
6) alkoxyl, (C
1-C
6) halogenated alkoxy, nitro, cyano group or (C
1-C
6) alkoxy carbonyl group.
W more suitable among the present invention is for there being the pyridine group of trifluoromethyl replacement at the carbonyl ortho position, R is propargyl or 2, the 3-glycidyl, and X is halogen or methyl, n equals 1.
Among the present invention more suitably W be 4-(trifluoromethyl)-3-pyridine radicals, R is a propargyl, X is 3-chlorine or 3-methyl.
Among the present invention, (C
1-C
6) alkyl represents the alkane of straight or branched, as methyl, ethyl, n-pro-pyl, isopropyl, normal-butyl, second butyl, tertiary butyl, n-pentyl and n-hexyl.(C
1-C
6) alkoxyl represents the alkoxy grp of straight or branched, as methoxyl group, ethyoxyl, positive propoxy, isopropoxy.Halogen is represented fluorine, chlorine, bromine or iodine.(C
1-C
6) haloalkyl represents the alkane of the straight or branched that replaced by one or more halogen atoms, as trifluoromethyl, pentafluoroethyl group, 2,2,2-trifluoroethyl.(C
1-C
6) alkoxy grp of the straight or branched that replaces by one or more halogen atoms of haloalkoxy basis representation, as trifluoromethoxy, five fluorine ethyoxyls, chlorine methoxyl group.(C
1-C
6) alkoxy carbonyl group represents the alkoxy grp of the straight or branched that links to each other with carbonyl, as methoxycarbonyl group and carbethoxyl group.(C
3-C
6) alkynyl group represents the alkynes of straight or branched, as propargyl, 2-alkynes butyl.(C
3-C
6) epoxy alkyl represents the alkyl chain of straight or branched, as contain n-pro-pyl, isopropyl, normal-butyl, second butyl, isobutyl group, n-pentyl and the n-hexyl of epoxide group, and for example, 2,3-glycidyl and 2,3-epoxy butyl.
The present invention also comprises by a certain N-(heterocycle formyl) the sulfonamide Herbicidal combinations of being made up of the compound and the carrier of activity of weeding shown in the general formula (I).
Other embodiments of the present invention are method of controlling weeds, and this method comprises that compound shown in the general formula of herbicidally effective amount (I) and agricultural are gone up N-(heterocycle formyl) sulfonamide Herbicidal combinations that acceptable carrier forms to impose on the surface of somatomedin of the places of described weeds or described weeds or described weeds.
According to the present invention, compound (I) by the benzsulfamide shown in the general formula (II) with make by the heterocycle acyl chloride reaction shown in the general formula (III):
Wherein, W, Xn is identical with definition in the general formula (I) with R.Compound (II) or compound (III) can maybe can be bought by the known method preparation.
Benzsulfamide (II) can carry out in solvent or under the solvent-free condition with the reaction of (heterocycloformyl) chlorine (III).Generally, use is more suitable to the solvent of reaction condition inertia.Spendable solvent is water, ethers, aromatic hydrocarbon, N, dinethylformamide, methyl-sulfoxide, pyridine and composition thereof.
The range of reaction temperature broad generally can be controlled between the reflux temperature of 0 ℃ and reactant mixture.Carry out under the pressure of the general environment around of reaction pressure.Reaction time was generally 30 minutes to 6 hours.
Benzsulfamide (II) is not very crucial with the ingredient proportion of (heterocycloformyl) chlorine (III) reaction, but benzsulfamide is excessive slightly usually, is favourable as excessive 5%-20% mole to reaction.
Reaction is carried out in the presence of the alkali as acid binding agent usually.Suitable alkali comprises alkali metal hydride, as sodium hydride; Alkali metal hydroxide is as sodium hydroxide and potassium hydroxide; And organic base, as pyridine and triethylamine.The consumption of alkali is generally excessive slightly with respect to (heterocycloformyl) chlorine (III), and common excessive 10%-200% mole is favourable to reaction.
N-of the present invention (heterocycle formyl) sulfonamide compounds and composition thereof can be used as emerge before and emerge the back weed killer herbicide.Generally speaking, herbicide before seedling stage was used before crop emerges usually.Herbicide after seedling is used with growing period after crop emerges.This compounds generally demonstrates selectivity to several important crop on the agricultural such as corn, cotton, paddy rice, soybean and wheat.
Compound of the present invention is administered on soil or the blade face with solution or dosage form.This compound is dissolved in the carrier usually or is mixed with preparation so that be easier to disperse when using as weed killer herbicide.For example: but these chemicals can be made into wet-milling, emulsifiable concentrate, pulvis, colloidal suspending agent, aerosol or missible oil.In these compositions, added a kind of liquid or solid carrier and when needs, can mix suitable surfactant.
Generally, particularly when on leaf, spraying, wish to contain in the composition adjuvant in the practical operation, as wetting agent, spreading agent, dispersant, sticker, adhesive etc.Be common to this class adjuvant of this area, can be at the John W.McCutcheon, the publication Detergents and Emulsifiers of company, Annual.Allured PublishingCompany, Ridgewood, New Jersey finds among the U.S.A..
N-of the present invention (heterocycle formyl) sulfonamide compositions can be used with the form of herbicide sprays by method commonly used, for example uses traditional high power capacity hydraulic atomizing, low capacity hydraulic atomizing, gas blowout mist, aerial spraying or dusting.Dilution factor and consumption will depend on the type of device therefor, the method for using and the weeds that will control, but the comparatively suitable effective dose of selecting usually is that per hectare 150 restrains 4800 grams, and preferred effective dose is that per hectare 600 restrains 3600 grams.
N-of the present invention (heterocycle formyl) sulfonamide compositions can mix with fertilizer before using mutually.Used in the solid fertilizer composition of said N-(heterocycle formyl) sulfonamide compounds in a class, fertilizer or getting fat component as ammonium sulfate, ammonium nitrate or ammonium phosphate, can have been applied with one or more compounds.Said solid chemical compound or solid fertilizer also can mix in mixing apparatus, and perhaps they can be combined into granular composition with fertilizer.Fertilizer can use any ratio, but the ratio of general said N-(heterocycle formyl) sulfonamide compounds in its Ru 2006101161 is about 5% to 25%.These compositions have been controlled the growth that does not need plant when fertilizer is provided, promotes required plant growth.
Use for some, can in weed killer herbicide of the present invention, add one or more other weed killer herbicide, can produce additional advantage and effect thus.When using Herbicidal mixtures, employed relative scale depends on the relative drug effect of this mixture to desire processing plant.The example of other weed killer herbicide that can together use with weed killer herbicide of the present invention comprises:
Carboxylic acid and derivative 2,3 thereof, 6-trichlorobenzoic acid and salt thereof; 2,3,5,6-tetrachloro-benzoic acid and salt thereof; 2-methoxyl group-3,5,6-trichlorobenzoic acid and salt thereof; 2-methoxyl group-3,6-dichlorobenzoic acid and salt thereof; 2-methyl-3,6-dichlorobenzoic acid and salt thereof; 2,3-two chloro-6-methyl benzoic acid and salt thereof; 2,4 dichloro benzene ethoxyacetic acid and salt thereof and ester; 2,4,5 T 2,4,5 trichlorophenoxy acetic acid and salt thereof and ester; 2-methyl-4-tomatotone and salt and ester; 2-(2,4, the 5-Trichlorophenoxy) propionic acid and salt and ester; 4-(2,4 dichloro benzene oxygen base) butyric acid and salt and ester; 4-(2-methyl-4-chlorophenoxy) butyric acid and salt and ester; 2,3,6-trichlorophenyl acetate and salt thereof; 3,6-epoxy hexahydrobenzene dioctyl phthalate and salt thereof; 4,3,5, the 6-DCPA; Trichloroacetic acid and salt thereof; 2,2-dichloropropionic acid and salt thereof; 2,3-dichloro isobutyric acid and salt 2-thereof (4-isopropyl-4-methyl-5-oxygen-2-imidazoline-2-yl) different third ammonium of nicotinic acid; 2-(4,5-dihydro-4-methyl-4-(1-first and second bases)-5-oxygen-1H-imidazoles-2-yl)-3-quinoline carboxylic acid; 6-(4-isopropyl-4-methyl-5-oxygen-2-imidazoline-2-yl)-meta-toluic acid methyl esters; 6-(4-isopropyl-4-methyl-5-oxygen-2-imidazoline-2-yl)-para Toluic Acid's methyl esters; N-(phospho methyl) glycine isopropyl ammonium salt; (3,5,6-three chloro-(2-pyridine radicals) oxygen) acetate; 3,7-two chloro-8-Quinoline Carboxylic Acids; DL-high lactamine-4-base (methyl) ammonium phosphate;
Carbamic acid derivative N, N-two (n-pro-pyl) thioxanthamide; N, N-two (n-pro-pyl) thiocarbamic acid n-propyl; N-ethyl-N-(normal-butyl) thioxanthamide; N-ethyl-N-(normal-butyl) thiocarbamic acid n-propyl; N, N-diethyldithiocar bamic acid 2-chlorine allyl ester; The phenylcarbamic acid isopropyl ester; N-(chlorphenyl) carbamic acid isopropyl ester; 4-chloro-2-butynyl-N-(chlorphenyl) carbamate; N-(3, the 4-dichlorophenyl) methyl carbamate; Dinitro one neighbour (sec-butyl) phenol and salt thereof; Pentachlorophenol and salt thereof; S-(4-chlorophenyl)-N, N-diethyl sulfide aminocarbamic acid ester.
Ureas 2-chloro-N-((4-methoxyl group-6-methyl isophthalic acid, 3, the 5-triazine-2-yl) amino carbonyl) benzsulfamide that replaces; 3-(3, the 4-dichlorophenyl)-1, the 1-dimethyl urea; 3-phenyl-1, the 1-dimethyl urea; 3-(3, the 4-dichlorophenyl)-3-methoxyl group-1, the 1-dimethyl urea; 3-(4-chlorphenyl)-3-methoxyl group-1, the 1-dimethyl urea; 3-(3, the 4-dichlorophenyl)-1-normal-butyl-1-methyl urea; 3-(3, the 4-dichlorophenyl)-1-methoxyl group-1-methyl urea; 3-(4-chlorphenyl)-1-methoxyl group-1-methyl urea; 3-(3, the 4-dichlorophenyl)-1,1,3-methyl urea; 3-(3, the 4-dichlorophenyl)-diethyl urea; N-(4-isopropyl phenyl)-N, the N-dimethyl urea; 2-((((4,6-dimethyl-2-pyrimidine radicals) amino) carbon back) sulfonyl) methyl benzoate; N-((6-methoxyl group-4-methyl isophthalic acid, 3,5-triazine-2-yl) amino carbonyl)-2-(2-chloroethoxy)-benzsulfamide; 2-(((6-methoxyl group-methyl isophthalic acid, 3,5-triazine-2-yl) amino carbonyl) sulfonyl) methyl benzoate; 3-(((6-methoxyl group-4-methyl isophthalic acid, 3,5-triazine-2-yl) amino carbonyl) sulfonyl)-2-thiophenecarboxylate; 2-((((4,6-dimethoxy-2-pyrimidine radicals) amino) carbon back) sulfonyl methyl) methyl benzoate; 2-(((6-methoxyl group-4-methyl isophthalic acid, 3,5-triazine-2-yl) methylamino carbonyl) sulfonyl) methyl benzoate;
The triazines 2-chloro-4 that replaces, 6-two (ethylamino)-s-triazine; 2-chloro-4,6-two (3-methoxyl group n-propylamine base)-s-triazine; 2-chloro-4-ethylamino-6-isopropylamino-s-triazine; 2-chloro-4,6-two (isopropylamino)-s-triazine; 2-chloro-4-ethylamino-6-(3-methoxyl group n-propylamine base) s-triazine; 2-methyl mercapto-4,6-two (isopropylamino)-s-triazine; 2-methyl mercapto-4-ethylamino-6-isopropylamino-s-triazine; 2-methoxyl group-4,6-two (isopropylamino)-s-triazine; 2-methoxyl group-4-ethylamino-6-isopropylamino-s-triazine; 2-methyl mercapto-4-(2-methoxyl group ethylamino)-6-isopropylamino-triazine; 4-amino-6-tertiary butyl-3-methyl mercapto-1,2,4-triazine-5 (4H)-ketone;
Diphenyl ether derivative 2,4-two chloro-4 '-itrodiphenyl ethers; 2,4,6-three chloro-4 '-itrodiphenyl ethers; 2,4-two chloro-6-fluoro-4 '-itrodiphenyl ethers; 3-methyl-4 '-itrodiphenyl ethers; 3,5-dimethyl-5 '-itrodiphenyl ethers; 2,4 '-dinitro-4-(trifluoromethyl) diphenyl ether; 2,4-two chloro-3 '-methoxyl group-4 '-itrodiphenyl ethers; 5-(2-chloro-4-trifluoromethyl) phenoxy group-2-nitrobenzoic acid sodium; 2-chloro-1-(3-methoxyl group-4-nitro) phenoxy group-4-trifluoromethylbenzene; 5-(2-chloro-4-trifluoromethyl) phenoxy group-2-nitrobenzoic acid carbethoxyl group ethyl ester; 5-(2-chloro-4-trifluoromethyl) phenoxy group-N-mesyl-2-nitrobenzamide;
Anilid class 2-chloro-N-(2-ethyl-6-tolyl)-N-(2-methoxyl group-1-Methylethyl) acetamide; 2-chloro-2 ', 6 '-diethyl-N-(2-propoxyl group ethyl) antifebrin; N-(3, the 4-dichlorophenyl) propionamide; N-(3, the 4-dichlorophenyl) MAAm; N-(3-chloro-4-aminomethyl phenyl)-2-methylpent acid amides; N-(3, the 4-dichlorophenyl) pivaloyl amine; N-(3, the 4-dichlorophenyl)-α, the alpha-alpha-dimethyl acetamide; N-isopropyl-N phenylchloride acetamide N-n-butoxy methyl-N-(2,6-diethyl phenyl) chloroacetamide; N-ethoxyl methyl-N-(2,6-diethyl phenyl) chloroacetamide;
Phenoxy carboxylic acid herbicides 2-(4-(2,4 dichloro benzene oxygen base) phenoxy group) methylpropionate; 2-(4-(3-chloro-5-trifluoromethyl-2-pyridine radicals oxygen base) phenoxy group) methyl propionate; (R)-2-(4-(5-trifluoromethyl-2-pyridine radicals oxygen base) phenoxy group) butyl propionate; 2-(4-((6-chloro-2-benzoxazolyl) oxygen base) phenoxy group) ethyl propionate; 2-(4-(5-trifluoromethyl-2-pyridine radicals oxygen base) phenoxy group) butyl propionate; 2-(4-(6-chloro-2-quinoline oxy) phenoxy group) ethyl propionate;
Uracil 5-bromo-3-sec-butyl-6-methyluracil; 5-bromo-3-cyclohexyl-1, the 6-dimethyl uracil; 5-bromo-3-isopropyl-6-methyluracil; 3-cyclohexyl-5, the 6-dimethyl uracil; 3-tertiary butyl-5-chloro-6-methyluracil;
Nitrile 2, the 6-dichlorobenzonitrile; Diphenylacetonitrile; 3,5-two bromo-4-4-hydroxy-benzonitriles; 3,5-two iodo-4-4-hydroxy-benzonitriles;
Other organic herbicide 2-chloro-N, N-diallyl acetamide; N-(1,1-dimethyl-2-propargyl)-3, the 5-dichloro-benzamide; Maleic acid hydrazide; 3-amino-1,2, the 4-triazole; Methylarsonic acid one sodium; Tonarsin; N, N-dimethyl-α, α-diphenyl acetamide; N, N-di-2,6-dinitro-4-5-trifluoromethylaniline; N, N-di-2,6-dinitro-4-methylaniline; N, N-di-2,6-dinitro-4-methyl sulphonyl aniline; O-(2,4 dichloro benzene base)-O-isopropyl methyl thio-phosphamide; 4-amino-3,5,6-three chloro-pyridine carboxylic acids; 2,3-two chloro-1,4-naphthoquinones; Two (methoxyl group sulfo-carbon back) disulphide; 3-(1-Methylethyl)-1H-2,1,3-benzothiadiazine-(4) 3H-ketone-2,2-dioxide.7-dihydrodi pyridine phenol (1,2-a:2 ', 1 '-c)-pyrazine two drone salt; 1 '-dimethyl-4,4 '-two pyridinium salt; 3,4,5,6-tetrahydrochysene-3,5-dimethyl-2-sulfo--2H-1,3,5 ,-thiadiazine; 2-(1-(ethoxy imino) butyl)-5-(different (ethylmercapto group) propyl group)-3-hydroxyl-2-cyclohexene-1-ketone; 2-(2-chlorphenyl) methyl-4,4-dimethyl-3-isoxazole alkane ketone; N-(1-ethyl propyl)-3,4-dimethyl-2,6-dinitrobenzamide; 4-chloro-5-(methylamino)-2-(m-trifluoromethylphenyl)-3-(2H)-pyridazinone; 2-(3, the 5-dichlorophenyl)-2-(2,2, the 2-trichloromethyl) oxirane.
When using the mixture of weed killer herbicide, employed relative quantity will depend on pending crop and the selectivity degree in the weed control of expection.
Should be clear and definite be, can carry out various conversion and change under the situation of the spirit and scope of the present invention defined by the claims.
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 is by the scope of the present invention shown in the claim.
Table 1: preferred compound
| Example | ?????R | ????Xn | ?????????????W |
| ??1 | Propargyl | 3-chlorine | 4-trifluoromethyl-3-pyridine radicals |
| ??2 | Propargyl | 3-chlorine | 2-trifluoromethyl-5-methyl-3-furyl |
| ??3 | Propargyl | The 3-methyl | 4-trifluoromethyl-3-pyridine radicals |
| ??4 | Propargyl | 3-chlorine | 2-chloro-4-trifluoromethyl-5-pyrimidine radicals |
The preparation of example 1:3-chloro-N-propargyl-N-(4-5-flumethiazine-3-carbonyl) benzsulfamide:
Sodium hydride (0.6 gram, 60%, 14mmol) joined 3-chloro-N-propargyl benzsulfamide under the frozen water cooling in 5 minutes (3.0 grams are 13mmol) in the solution that forms with 40 milliliters of THF in batches.Continue to stir after 20 minutes, (2.7 grams 13mmol) and 10 milliliters of solution that THF form, stirred 10 hours under the room temperature to drip 4-5-flumethiazine-3-formyl chloride in 5 minutes in mixture.Reactant mixture is poured in 100 milliliters of ethyl acetate and 100 ml waters, and the water of telling is with 2 * 50 milliliters of ethyl acetate extractions.Merge organic facies, with saturated sodium bicarbonate aqueous solution, water and saturated common salt water washing, anhydrous sodium sulfate drying.Slough solvent and obtain 4.0 gram oil.100 gram silica gel column chromatographies are purified, and flowing phase is 25% ethyl acetate/hexane solution, obtain 2.5 gram 3-chloro-N-propargyl-N-(4-5-flumethiazine-3-carbonyl) benzsulfamides.Fusing point: 82-85 ℃.
The preparation of example 2:3-chloro-N-propargyl-N-(5-Methyl-2-trifluoromethyl furans-3-carbonyl) benzsulfamide:
Operating procedure is identical with example 1.Replace 4-5-flumethiazine-3-formyl chloride with 5-Methyl-2-trifluoromethyl furans-3-formyl chloride, obtain 3-chloro-N-propargyl-N-(5-Methyl-2-trifluoromethyl furans-3-carbonyl) benzsulfamide.Fusing point: 70-72 ℃.
The preparation of example 3:3-methyl-N-propargyl-N-(4-5-flumethiazine-3-carbonyl) benzsulfamide:
Sodium hydride (0.4 gram, 60%, 10mmol) joined 3-methyl-N-propargyl benzsulfamide under the frozen water cooling in 5 minutes (2.1 grams are 10mmol) in the solution that forms with 40 milliliters of THF in batches.Mixture stirred after 20 minutes, in 5 minutes, drip 4-5-flumethiazine-3-formyl chloride (1.5 grams, 7mmol) and 10 milliliters of solution that THF form.Stirred 10 hours under the room temperature.Reactant mixture is poured in 50 milliliters of ethyl acetate and 50 ml waters, and the water of telling is with 2 * 25 milliliters of ethyl acetate extractions.Merge organic facies, with saturated sodium bicarbonate aqueous solution, water and saturated common salt water washing, anhydrous sodium sulfate drying.Slough solvent and obtain 2.0 gram solids.70 gram silica gel column chromatographies are purified, and flowing phase is 25% ethyl acetate/hexane solution, obtain 1.2 gram 3-methyl-N-propargyl-N-(4-5-flumethiazine-3-carbonyl) benzsulfamides.Fusing point: 111-114 ℃.
The preparation of example 4:3-chloro-N-propargyl-N-(2-chloro-4-trifluoromethyl pyrimidine-5-carbonyl) benzsulfamide:
Operating procedure is identical with example 1.With (2-chloro-4-trifluoromethyl pyrimidine-5-formyl chloride replaces 4-5-flumethiazine-3-formyl chloride to obtain 3-chloro-N-propargyl-N-(2-chloro-4-trifluoromethyl pyrimidine-5-carbonyl) benzsulfamide.Fusing point: 106-107 ℃.
Give birth to the survey method
Test before the seedling: in the vinyl disc of (wide * length * height) 20 * 30 * 8 centimetres, adding contains the soil that this locality of 1.0 to 1.5% organic matters obtains, and the seed degree of depth is 1.27 centimetres.
Test behind the seedling: it is in 7.62 or 10.16 centimetres the dish that the examination assortment is implanted in diameter, after emerging 7 to 21 days, when monocotyledon weed in the 2-4 leaf phase, broad leaved weed is sprayed when the 1-2 leaf period.
According to different hydrojet concentration, sprayed volume is 234 liters of per hectares or 468 liters usually.Usually with the former medicine of acetone solution, spray with mobile belt sprayer.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 drying box dry.
Examination material after the atomized 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 investigates in 2-3 week.Carry out active classification with 0% (invalid) to 100% (control fully).Inhibiting rate is total effect of various infringements such as chlorosis, withered spot, retarded growth or the calcination of leaf angle.With compare after obtain the result, see Table 2A and 2B:
Table 2A: active before the seedling
| Example | Dosage gram/hectare | ???BID | ????NS | ???SMT | ???VEL | ??BYG | ?CRB | ??FOX | ??RYE |
| ??1 | ??2400 | ???0 | ????0 | ???0 | ???15 | ??100 | ?100 | ??100 | ??0 |
| ??2 | ??2400 | ???20 | ????20 | ???50 | ???10 | ??0 | ?0 | ??0 | ??0 |
| ??3 | ??1200 | ???0 | ????0 | ???0 | ???0 | ??100 | ?100 | ??100 | ??0 |
| ??4 | ??2400 | ???0 | ????0 | ???0 | ???0 | ??0 | ?0 | ??0 | ??0 |
Table 2B: active behind the seedling
| Example | Dosage gram/hectare | ???BID | ???NS | ??SMT | ???VEL | ???BYG | ???CRB | ???FOX | ??RYE |
| ??1 | ???2400 | ???0 | ???20 | ??15 | ???25 | ???95 | ???60 | ???90 | ???0 |
| ??2 | ???2400 | ???0 | ???0 | ??0 | ???0 | ???0 | ???0 | ???0 | ???0 |
| ??3 | ???1200 | ???25 | ???40 | ??0 | ???30 | ???85 | ???20 | ???35 | ???0 |
| ??4 | ???2400 | ???0 | ???15 | ??0 | ???15 | ???0 | ???0 | ???35 | ???0 |
Table 3A: monocotyledon weed title
| Be called for short | Generic name | Latin name |
| ???BYG | The barnyard grass grass | Echinochloa?crus-galli |
| ???CRB | Lady's-grass (greatly) | Digitaria?sanguinalis |
| ???FOX | Green dog tail | Setaria?viridis |
| ???RYE | Perennial ryegrass | Lolium?perenne |
Table 3B: broad leaved weed title
| Be called for short | Generic name | Latin name |
| ????BID | Beggar-ticks | ????Bidens?pilosa |
| ????NS | Black nightshade (deceiving) | ????Solanum?nigrum |
| ????SMT | Few | ????Polygonum ????lapathifolium |
| ????VEL | Piemarker | ????Abutilon?theophrasti |
Claims (9)
1 one kinds of sulfonamides herbicides is characterized in that title compound of the present invention (I) belongs to agricultural herbicide, and general formula is:
Wherein:
W is a heterocycle, comprises pyridine, pyrazine, and pyrimidine, pyridazine, furans and thiophene etc. have halogen (C on the ring Yu on the carbonyl ortho position
1-C
6) the alkyl replacement,
R is (C
3-C
6) alkynyl group or (C
3-C
6) epoxy alkyl,
X is halogen, (C
1-C
6) alkyl, (C
1-C
8) haloalkyl, (C
1-C
6) alkoxyl, (C
1-C
6) halogenated alkoxy, nitro, cyano group or (C
1-C
6) alkoxy carbonyl group, n equals 0,1,2 or 3.
2 compounds as claimed in claim 1 is characterized in that: wherein W is for there being the pyridine group of trifluoromethyl replacement at the carbonyl ortho position, and R is propargyl or 2, the 3-glycidyl, and X is halogen or methyl, n equals 1.
3 compounds as claimed in claim 2 is characterized in that: wherein W is 4-trifluoromethyl-3-pyridine radicals, and R is a propargyl, and X is 3-chlorine or 3-methyl.
4 compounds as claimed in claim 3 is characterized in that: wherein X is a chlorine, and described compound is 3-chloro-N-propargyl-N-(4-5-flumethiazine-3-carbonyl) benzsulfamide.
5 compounds as claimed in claim 3 is characterized in that: wherein X is a methyl, and described compound is 3-methyl-N-propargyl-N-(4-5-flumethiazine-3-carbonyl) benzsulfamide.
6 one kinds of Herbicidal combinations is characterized in that: said composition comprises that described compound of claim 1 and agricultural thereof go up acceptable carrier.
7 one kinds of Herbicidal combinations as claimed in claim 6 is characterized in that: wherein also contain fertilizer or getting fat material.
8 one kinds of control method for weed, it is characterized in that: this method comprises the Herbicidal combinations as claimed in claim 6 of using herbicidally effective amount on somatomedin of these weeds or these weeds or place.
9 in accordance with the method for claim 8, and the growth place of its weeds is corn, cotton, paddy rice, soybean or wheat paddock.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN99112943A CN1091349C (en) | 1999-05-20 | 1999-05-20 | N-(heterocycloformyl) sulfonamide herbicide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN99112943A CN1091349C (en) | 1999-05-20 | 1999-05-20 | N-(heterocycloformyl) sulfonamide herbicide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1274528A true CN1274528A (en) | 2000-11-29 |
| CN1091349C CN1091349C (en) | 2002-09-25 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN99112943A Expired - Fee Related CN1091349C (en) | 1999-05-20 | 1999-05-20 | N-(heterocycloformyl) sulfonamide herbicide |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1091349C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003028458A1 (en) * | 2001-09-24 | 2003-04-10 | Bayer Cropscience Gmbh | N-thio-nicotinamide derivatives and related compounds for use as pesticides |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4157257A (en) * | 1976-10-01 | 1979-06-05 | Utsunomiya University | Benzenesulfonamide derivatives |
-
1999
- 1999-05-20 CN CN99112943A patent/CN1091349C/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003028458A1 (en) * | 2001-09-24 | 2003-04-10 | Bayer Cropscience Gmbh | N-thio-nicotinamide derivatives and related compounds for use as pesticides |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1091349C (en) | 2002-09-25 |
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