CN1145723A - Herbicidal compositions containing metolachlor and sulfonylureas and their method of use - Google Patents

Abstract

The invention relates to sulfonylurea and acetanilide compounds with weeding activity, and the method of them controlling adverse plants growth in paddy.

Description

The Herbicidal combinations and the application method thereof that contain metolachlor and sulfonylureas

The present invention relates to the agriculturally useful compositions of some sulfonylurea and monoacetylaniline class and the using method that conduct is used for the selective herbicide of rice thereof with herbicide effect.

The noval chemical compound that can effectively control the undesirable plant growth has demand always, under modal situation, seeking such compound is in such as useful crops (only lifting several examples) such as cotton, rice, corn, wheat and soybean, optionally controls weed growth.Weed growth in these crops will cause heavy losses as not adding control, reduces farmer's income, increases consumer's cost.In other cases, need to control the weed killer herbicide of all plant growings.Need the zone that all plants are controlled fully be had, for example rail near zone, basin and industrial reservoir area.Have many products that are used for above-mentioned purpose to sell on the market, but that people still seek is more effective, cost is lower and the product of environmental sound constantly.

" sulfonylurea " weed killer herbicide is the extremely strong class weed killer herbicide of finding recent years of effectiveness, generally by a sulfonylureas bridge (SO ₂NHCONH-) connect two aromatic rings or hetero-aromatic ring and constitute.

The monoacetylaniline class also is the potent weed killer herbicide of a class, but its phytotoxicity is defective when being applied to rice.

The open JAP-60 (1985)-45,507 of Japan Patent discloses the sulfonylurea of following formula and the Herbicidal synergistic activity between the monoacetylaniline classes such as the fourth grass lock and the third careless amine:

Wherein:

A is a low alkyl group;

B is H or low alkyl group;

R is a low alkyl group;

X and Y are low alkyl group or lower alkoxy independently. Fourth grass lock

Isobutyl grass lock

U.S.4,645,530 disclose ethyl chloride Sulfometuron Methyl (chlorimuron ethyl) and metolachlor or the mixture of weeds lock and the practicality in soybean thereof.

Open JAP-62 (1987)-67,007 of Japan Patent and EP-A-282,613 disclose the sulfonylurea of following formula and the Herbicidal synergistic activity between weed killer herbicides such as metolachlor or weeds lock:

Wherein:

R ₁Be halogen;

R ₂Be low alkyl group;

X and Y are alkyl, alkoxyl, halogen or OCF independently ₂H;

Z is CH or N.

These lists of references are both not open, and also the hint rice of the monoacetylaniline class of formula II being caused with formula I sulfonylurea damages and detoxifies.

The present invention relates to some Herbicidal combinations, these compositions comprise the monoacetylaniline compounds of a kind of formula IIa-IIc of one or more formulas Ia-Ie sulfonyl urea compound of herbicidally effective amount and herbicidally effective amount.The invention still further relates to a kind of method of controlling undesirable plant in the rice, this method comprises, uses the above-mentioned composition of herbicidally effective amount in the undesirable plant place.The method of the monoacetylaniline class weed killer herbicide infringement that the present invention relates to protect rice to avoid formula IIa-IIc; this method comprises; with the described monoacetylaniline class weed killer herbicide of herbicidally effective amount and one or more formulas Ia-Ie sulfonylureas of herbicidally effective amount, combined administration is in rice plants or rice plants place.The monoacetylaniline class of formula Ia-Ie sulfonylurea and formula IIa-IIc is following compound and is suitable for agricultural salt: 2-((((((4,6-dimethoxy-2-pyrimidine radicals) amino) carbonyl) amino) sulfonyl) methyl) methyl benzoate (bensulfuron-methyl, Ia);

(((((4,6-dimethoxy-2-pyrimidine radicals) amino) carbonyl) amino) sulfonyl)-(ethyl pyrazoles sulphur swells (pyrazosulfuron ethyl) 1-methyl isophthalic acid H-pyrazoles-4-carboxylic acid, ethyl ester 5-, Ib);

2-(((((4-methoxyl group-6-methyl isophthalic acid, 3,5-triazine-2-yl) amino) carbonyl) amino) sulfonyl) methyl benzoate (metsulfuron-methyl, Ic); 2-(((((4-chloro-6-methoxyl group-2-pyrimidine radicals) amino) carbonyl) amino) sulfonyl) ethyl benzoate (ethyl chloride Sulfometuron Methyl (chlorimuron ethyl), Id);

N-(((4,6-dimethoxy-2-pyrimidine radicals) amino) carbonyl)-1-methyl-4-(2-methyl-2H-tetrazolium-5-yl)-1H-pyrazoles-5-sulfonamide (Ie); 2-chloro-N-(2-ethyl-6-aminomethyl phenyl)-N-(2-methoxyl group-1-Methylethyl) acetamide (metolachlor, IIa);

2-chloro-N-(2,6-diethyl phenyl)-N-(methoxy) acetamide (the weeds lock, IIb);

2-chloro-N-(ethoxyethyl)-N-(2-ethyl-6-aminomethyl phenyl) acetamide (metolachlor, IIc); Its prerequisite is:

If a) herbicidal composition only contains a kind of formula I sulfonylureas, then this sulfonylureas is not the ethyl chloride Sulfometuron Methyl, (Id);

B) if formula I compound is Ie, then formula II compound is IIc, i.e. metolachlor.

Preferred composition of the present invention comprises:

1, a kind of herbicidal composition, it comprises one or more formulas Ia-Ie sulfonylureas and as the metolachlor of the monoacetylaniline of formula IIa.

2, a kind of herbicidal composition of preferred composition 1, wherein sulfonylureas is a formula Ie compound, promptly N-(((4,6-dimethoxy-2-pyrimidine radicals) amino) carbonyl)-1-methyl-4-(2-methyl-2H-tetrazolium-5-yl)-1H-is than azoles-5-sulfonamide.

3, a kind of herbicidal composition of preferred composition 1, wherein sulfonylureas is a formula Ib compound, promptly ethyl pyrazoles sulphur is grand.

4, a kind of herbicidal composition of preferred composition 1, wherein sulfonylureas is formula Ic compound, i.e. metsulfuron-methyl.

5, a kind of herbicidal composition of preferred composition 1, wherein sulfonylureas is formula Ia compound, i.e. bensulfuron-methyl.

6, a kind of herbicidal composition of preferred composition 1, wherein sulfonylureas is that formula Ia compound is that bensulfuron-methyl and formula Ic compound are metsulfuron-methyl.

7, a kind of herbicidal composition of preferred composition 1, wherein sulfonylureas is that metsulfuron-methyl and formula Id compound are the ethyl chloride Sulfometuron Methyl for the Ic compound.

8, a kind of method of controlling undesirable plant in the rice, this method comprise, uses the monoacetylaniline of the formula IIa-IIc of a kind of formula Ia-Ie sulfonylureas of herbicidally effective amount and a kind of herbicidally effective amount.

The most preferred composition of the present invention is the herbicidal composition of formula IIa and Ia and the herbicidal composition of formula IIa and Ib.

The sulfonylurea of formula Ia-Ie can improve the tolerance of rice to some monoacetylaniline class weed killer herbicide.The present composition can improve safety, the reduction rate of application of crop when being applied to rice, perhaps can reach the weeds control effect when being better than using each component separately.

Formula I and II compound can prepare with the following known method of this area:

The compound number list of references

Ia U.S.4,420,324

Ib U.S.4,931,081

Ic U.S.4,383,113

Id U.S.4,547,215

Ie U.S.4,746,311

IIa U.S.3,937,730

IIb U.S.3,442,945

IIc U.S.4,258,196

Preparation

Formula I and II compound can be prepared with multiple mode:

(a) can prepare antipoison and weed killer herbicide respectively, and use or use simultaneously (for example as the bucket mix formulation) respectively with suitable weight ratio; Or

(b) can antipoison and weed killer herbicide be fitted over together by suitable weight ratio.

The useful preparation of formula I and II compound can prepare with conventional method.These preparations comprise pulvis, granula, pill, solution, suspending agent, emulsion, wetting powder, missible oil etc.Wherein there are many preparations directly to use.Spray agent can be scattered in the suitable medium, uses with every hectare of several sprayed volume that rise to several hectolitres.High concentration composition is mainly as the intermediate for further preparation usefulness.Put it briefly, these preparations contain the 0.1-99% that has an appointment (weight) active component and following (a) and (b) at least a composition: (a) about 0.1%-20% surfactant; (b) about 1%-99.9% solid or liquid inert diluent.More particularly, the general proportions of contained each composition is as follows in these preparations:

Percetage by weight ^*

Active component diluent surfactant wettable powder 20-90 0-74 1-10 oil-suspending agent, emulsion, solution (comprising missible oil) 3-50 40-95 0-15 aqueous suspension agent 10-50 40-84 1-20 pulvis 1-25 70-99 0-5 granula and pill 0.1-95 5-99.9 0-15 high concentration combination 90-99 0-10 0-2

^*Active component adds that at least one composition in surfactant or the thinner equals 100% (weight).

Certainly, the content of active component can be lower or higher, and this depends on the desired use and the physical property thereof of compound.The ratio of wishing surfactant and active component sometimes is higher, and this can realize by mixing surfactant in the preparation or mixing by bucket.

The typical solid thinner is described in people's such as Watkins " no matter agent of insecticide dust dilution agent and carrier handbook second edition (Dorland Books, Caldwell, New Jersey), but also can use other solid are mineral or industrial products.The preferred stronger thinner of water imbibition concerning wetting powder, the bigger thinner of preferred density concerning pulvis.Typical liquid diluent and solvent are described in " solvent guide " second edition (Interscience, New York, 1950) of Marsden.The preferred dissolution degree is lower than 0.1% concerning suspension concentrate, and concentrated solution is preferably under 0 ℃ stable to being separated." McCutcheon detergent and emulsifier year comment " (MC PublishingCorp., Ridgewood, New Jersey) and " surfactant complete works " (Chemical Publishing Co. of Sisely and Wood, Inc., New York, 1964), many surfactants and recommended use thereof have been listed.All preparations are all stung and are contained a small amount of additive to reduce foaming, caking, burn into growth of microorganism etc.

It is known preparing these method for compositions.Simple each composition that mixes can make solution.The fine powder solid composite prepares by mixing, and normally grinds in hammer-mill or fluid energy mill.Suspending agent prepares (referring to the United States Patent (USP) 3,060,084 of for example Littler) with wet grinding.The method that granula and pill can be used in spray active substance on the preformed particulate vector prepares, also can prepare with agglomeration technique (referring to J.E.Browning, " agglomeration ", ChemicalEngineering, on December 4th, 1967, the 147th page reaches each page later on; " Perry chemical industry handbook the 5th edition, McGraw-Hill, New York, each page after 1973, the 8-59 pages or leaves reach).

The further data of relevant preparing process, referring to for example:

The United States Patent (USP) of H.M.Loux on February 15th, 3,235,361,1996, the 6th hurdle the 16th walks to the 7th hurdle the 19th row, and embodiment 10 to 41;

The United States Patent (USP) of R.W.Luckenbaugh on March 14th, 3,309,192,1967, the 5th hurdle 43 walks to the 7th hurdle the 62nd row, and embodiment 8,12,15,39,41,52,53,58,132,138-140,162-164,166,167 and 169-182.

The United States Patent (USP) 2,891,855 of H.Gysin and E.Knusli, on June 23 nineteen fifty-nine, the 3rd hurdle the 66th walks to the 5th hurdle the 17th row, and embodiment 1-4;

G.C.Klingman " control of weeds " (" Weed Control as a Science ", JohnWiley and Sons, Inc., New York, 1961, the 81-96 pages or leaves);

J.D.Fryer and S.A.Evans " control of weeds handbook the 5th edition (" Weed contralHandbook ", B1ackwell Scientific Publications, Oxford, 1968, the 101-103 pages or leaves).

In the following example, all umbers all by weight, unless otherwise noted.

Embodiment A

Wetting powder

Metolachlor 45%

Bensulfuron-methyl 5%

Negel 2%

Sodium lignosulfonate 5%

Diatomite 43%

Each composition is mixed,, carry out the gas mill then, obtain particle diameter substantially all at the particle below 10 microns with the hammer-mill corase grind.Product is mixed once more, then packing.

Embodiment B

Granula

Metolachlor 5%

Bensulfuron-methyl 5%

Attagel particle (the 20-40 order U.S. 90%

Sieve; 0.84-0.42mm)

In double-cone mixer, the oily active component is sprayed onto on the Attagel particle surface.To pack again after the particle mixing.

Embodiment C

Oil-suspending agent

Metolachlor 22%

Bensulfuron-methyl 2.5%

Metsulfuron-methyl 0.5%

Polyoxyethylene sorbitol six oleates 5%

Senior fatty hydrocarbon ils 70%

Each one-tenth is placed in grinds together in the sand mill, reduce to about below 5 microns up to the granularity of solid particle.The thickness suspending agent of gained can directly be used, but is preferably in oil dilution back or uses after the emulsification in water.

Embodiment D

Wetting powder

Metolachlor 17%

Ethyl pyrazoles sulphur grand 3%

Negel 4%

Sodium lignosulfonate 4%

Low viscosity methylcellulose 3%

Attagel 69%

Fully mix each composition.In hammer-mill, grind to form basically all behind the particle below 100 microns, material is mixed once more and, then packing by 50 order U.S. sieves (aperture is 0.3mm).

Embodiment E

The low concentration granula

Metolachlor 1%

Bensulfuron-methyl 1%

Carrene 8%

Attagel particle (20-40 order U.S. sieve) 90%

Active component is dissolved in the solvent, in double-cone mixer, this solution is sprayed onto through taking off on the particle of dirt.After having sprayed solution, allow mixer turn round a bit of time, and then particle is packed.

Embodiment F

Aqueous suspension agent

Metsulfuron-methyl 5%

Metolachlor 5%

Polyacrylate thickeners 0.3%

Dodecylphenol polyglycol ether 0.5%

Sodium hydrogen phosphate 1%

Sodium dihydrogen phosphate 0.5%

Polyvinyl alcohol 1.0%

Water 82.2%

Mix each composition and grinding together in homogenizer, obtain granularity basically all at the particle below 5 microns.

Embodiment G

The low concentration granula

Metolachlor 0.1%

Metsulfuron-methyl 0.1%

Attagel particle (20-40 order U.S. sieve) 99.8%

Active component is dissolved in the solvent, in double-cone mixer, this solution is sprayed onto through taking off on the particle of dirt.After having sprayed solution, warm material makes the solvent evaporation.Make the material cooling, then packing.

Practicality

Formula Ia-Ie compound can be used for improving the tolerance of rice class crop to formula IIa-IIc weed killer herbicide institute induced damage resistive.The present composition can improve safety, the reduction rate of application of crop when being applied to rice, or produces the weeds control effect when being better than using each component separately.One or more formulas Ia-Ie compound and a kind of formula IIa-IIe compound combined administration in the plant place, can be realized agricultural weed control and crop safety.Formula Ia-Ie compound can be avoided infringement that formula IIa-IIc causes rice class crop or it is reduced to qualified level, and the control action to trouble some weed in the paddy rice (Oryza sativa) such as barnyard grass (Echinochloa crus-galli) and arrowhead (Saggitaria spp.) does not reduce or reduction hardly simultaneously.The control action of barnyard grass had both been comprised before the bud that activity of weeding also comprised activity of weeding behind the bud.

Formula Ia-Ie weed killer herbicide can be prepared with formula IIa-IIc weed killer herbicide respectively, also can with these compound after with the gained mixture as single entities preparation with use.Like this, these weed killer herbicides can be applied to crop simultaneously, also can fit over earlier to be applied to crop together again.

The herbicidally effective amount of formula Ia-Ie compound and formula IIa-IIc compound will become along with factor such as the value volume and range of product of selected particular compound, environmental aspect, preparation, application process, relevant plant.In general, formula Ia-Ie herbicide application rate should be 0.0005-1 kilogram active component/hectare, and the rate of application of formula IIa-IIc weed killer herbicide should be 0.01-5 kilogram active component/hectare.This area professional determines to reach the weeds control of expection level and the ratio of the required rate of application of crop safety and formula Ia-Ie weed killer herbicide and formula IIa-IIc weed killer herbicide easily.

Herbicidal composition of the present invention can use separately, also can mix usefulness with other commodity weed killer herbicides, insecticide or fungicide.Following table has been listed some can be for mixing the weed killer herbicide that uses.The mixture of one or more following weed killer herbicides and herbicidal composition of the present invention may be specially adapted to weeds control.Popular name chemical name Acifluorfen 5-(2-chloro-4-(trichloromethyl) phenoxy group)-2-nitrobenzoic acid acrolein 2-acrolein anilofos S-4-chloro-N-cumene carbamyl methyl-O, the O-dimethyl

The phosphorodithioate Aunar draw clean N-ethyl-N '-(1-Methylethyl)-6-methyl mercapto-1,3,5-triazines-

2,4-diamines aminotriazole 1H-1,2; 4-triazole-3-amine Amcide Ammate Amcide Ammate asulam ((4-aminophenyl) sulfonyl) methyl carbamate atrazine 6-chloro-N-ethyl-N '-(1-Methylethyl)-1; 3,5-triazine-2,4-

Diamines barban N-(3-chlorphenyl) carbamic acid 4-chloro-2-butynyl ester second fourth trefanocide N-butyl-N-ethyl-2; 6-dinitro-4-(trifluoromethyl) aniline Bensulfide O, two (1-Methylethyl) S-((2-((benzenesulfonyl) amino) second of O-

Base) phosphorodithioate Bentazon 3-(1-Methylethyl)-(1H)-2,1,3-benzothiadiazine-4 (3H)-ketone

2; 2-dioxide benzofluor N-(4-ethylmercapto group-2-(trifluoromethyl) phenyl) Methanesulfomide suffer N-benzoyl-N-(3; the 4-dichlorophenyl)-DL-methyl lactamine nitrofen 5-(2; the 4-dichlorophenoxy)-2-nitrobenzoic acid methyl esters bromacil 5-bromo-6-methyl-3-(1-methyl-propyl)-2; 4 (1H, 3H) pyrimidine two

Ketone Bromoxynil 3,5-two bromo-4-hydroxy-phenylformonitrile fourths grass lock N-(fourth oxygen methyl)-2-chloro-N-(2,6-diethyl phenyl) acetamide fourth sulphur imidazolone 3-(5-(1, the 1-dimethyl ethyl)-1,3,4-thiadiazoles-2-yl)-4-

The happy clever 4-(1, the 1-dimethyl ethyl) of hydroxyl-1-methyl-2-imidazolone fourth-N-(1-methyl-propyl)-2, the 6-dinitro

Two (2-methyl-propyl) the thiocarbamic acid S-ethyl ester Phytar cacodylic acid alkene grass of aniline Butilate peace 2-chloro-N, N-two-2-acrylic acetamide CDEC N, N-diethyldithiocar bamic acid 2-chlorallyl ester CGA 142,464 3-(4,6-dimethoxy-1,3,5-triazine-2-yl)-1-(2-(2-methoxy

Base oxethyl) urea chloramben 3-amino-2 benzenesulfonyl); 5-dichlorobenzoic acid chlorine metobromuron 3-(4-bromo-3-chlorphenyl)-1-methoxyl group-1-methyl urea chlormethoxynil 2; 4-dichlorophenyl-4-nitro-3-methoxyphenyl ether Mo 9 granular 2; 4; 6-trichlorophenyl-4-nitrobenzophenone ether Chloroxuron N '-(4-(4-chlorophenoxy) phenyl)-N; N-dimethyl urea chlorpropham 3-chlorphenyl carbamic acid 1-Methylethyl ester chlorine sulphur swells 2-chloro-N-(((4-methoxyl group-6-methyl isophthalic acid; 3,5-triazine-2-yl)

Amino) carbonyl) benzsulfamide chlortoluron N '-(3-chloro-4-aminomethyl phenyl)-N, N-dimethyl urea cinmethylin extroversion-1-methyl-4-(1-Methylethyl)-2-((2-aminomethyl phenyl) methoxy

Base)-and 7-oxabicyclo (2.2.1) heptane clothodim (E, E)-(±)-2-(1-(((3-chloro-2-acrylic) oxygen) imino group)

Propyl group)-5-(2-(ethylmercapto group) propyl group)-3-hydroxyl-2-cyclohexene-

1-ketone clemazone 2-((2-chlorphenyl) methyl)-4, and 4-dimethyl-3-isoxazole alkyl ketone cloproxydim (E, E)-2-(1-(((3-chloro-2-acrylic) oxygen) imino group) fourth

Base)-5-(2-(ethylmercapto group) propyl group)-3-hydroxyl-2-cyclohexene-1-

Ketone clopyralid 3, the calcium salt Cyanazine 2-of 6-two chloro-2-Pyridinecarboxylic Acid methylarsonic acid calcium methylarsonic acids ((4-chloro-6-ethylamino-1,3,5-triazines-2-yl) amino)-

The hot grand 3-ring octyl group-1 of 2-methyl propionitrile Cycloate cyclohexyl ethylenebis dithiocarbamate carbamic acid S-ethyl ester ring, the fast 1-methyl-4-phenylpyridinium cation cyprazine 2-chloro-4-(cyclopropyl amino) of the 1-dimethyl urea benzene grass-luxuriant peace of 6-(isopropyl amino) s-triazine ring N-(5-(2-chloro-1, the 1-dimethyl ethyl)-1,3,4-thiadiazoles-2-

Base) the cyclopropane carboxamide ring third Stam F-34 N-3 ', 4 '-dichloro cyclopropane-carboxylic acid anilide dalapon 2,2-dichloropropionic acid dazomet tetrahydrochysene-3,5-dimethylbenzene-2H-1,3,5-thiadiazine-2-thioketones dcpa 2,3,5,6-tetrachloro-1, the sweet grass spirit of 4-rutgers (3-(((phenylamino) carbonyl) oxygen) phenyl) urethane

Red two (1-Methylethyl) the thiocarbamic acid S-of ester desmetryn 2-(isopropyl amino)-4-methylamino-6-methyl mercapto s-triazine dichloro alkene (2,3-two chloro-2-propylene

Base) ester Dianat 3; 6-two chloro-O-Anisic Acid dichlobenil 2; 6-dichlorobenzonitrile 2; 4-drips propionic acid (±)-2-(2; the 4-dichlorophenoxy) propionic acid 2; 4-drips methyl phenylpropionate (±)-2-, and (4-(2; the 4-dichlorophenoxy) methyl propionate diethatyl N-(chloracetyl)-N-(2 phenoxy group); 6-diethyl phenyl) glycine ion grass pyrazoles 1; 2-dimethyl-3, the 5-diphenyl-1H-pyrazoles cation dimepiperate piperidines-1-bamic acid S-1-methyl isophthalic acid-happy amine N of phenethyl ester diethyl fluorine ³, N ³-two bases-2,4-dinitro-6-(trifluoromethyl)-1,3-benzene two

Amine dinoseb 2-(1-methyl-propyl)-4,6-dinitrophenol diformazan acetyldiphenylamine N, N-dimethyl-α-Ben Jibenyixian amine dipropetryn 6-ethylmercapto group-N, N '-two (1-Methylethyl)-1,3,5-triazine-2,4-

Diamines diquat 6,7-dihydrodi pyridine also (1,2-a:2 ', 1 '-c) the pyrazine sun from

Sub-diuron N '-(3, the 4-dichlorophenyl)-N, N-dimethyl urea dnoc 2-methyl-4, the disodium salt sand-grass of 6-dinitrophenol first arsine disodium methylarsonic acid is swelled N-(4-aminomethyl phenyl)-N '-(1-methyl isophthalic acid-phenylethyl) urea Aquathol 7-oxabicyclo (2.2.1) heptane-2,3-dioctyl phthalate EPTC dipropyl thiocarbamic acid S-ethyl ester esprocarb (SC2957) N-ethyl-N-(1, the 2-dimethyl) propyl group) thiocarbamic acid S-benzyl

Base ester alkene trefanocide N-ethyl-N-(2-methyl-2-acrylic)-2,6-dinitro-4-(trifluoro

Methyl) aniline ethofumesate (±) methanesulfonic acid 2-ethyoxyl-2,3-dihydro-3,3-dimethyl-5-benzo

Furans ester Fenac 2,3,6-chlorfenac fenoxaprop (±)-2-(4-((6-chloro-2-benzoxazolyl) oxygen) phenoxy group)

Propionic acid fenuron N, the salt flamprop N-benzoyl-N of N-dimethyl-N '-phenylurea fenuron trichloroacetic acid fenuron and trichloroacetic acid-(3-chloro-4-fluorophenyl)-DL-alanine fluazifop (±)-2-(4-((5-(trifluoromethyl)-2-pyridine radicals) oxygen) benzene

The oxygen base) propionic acid fluazifop-P (R)-2-(4-((5-(trifluoromethyl)-2-pyridine radicals) oxygen) benzene oxygen

Base) propionic acid fluchloralin N-(2-chloroethyl)-2,6-dinitro-N-propyl group-4-(trifluoromethyl) benzene

Amine fluometuron N, N-dimethyl-N '-(3-(trifluoromethyl) phenyl) urea fluorochloridone 3-chloro-4-(chloromethyl)-1-(3-(trifluoromethyl) phenyl)-2-pyrroles

Alkane ketone fluorine first fluorodifen p-nitrophenyl α, α, α-three fluoro-2-nitro p-tolyl ether fluoroglycofen 5-(2-chloro-4-(trifluoromethyl) phenoxy group)-2-nitrobenzoic acid carboxylic

Methyl ester fluridone 1-methyl-3-phenyl-5-(3-(trifluoromethyl) phenyl)-4 (1H)-pyrroles

Pyridine ketone fomesafen 5-(2-chloro-4-(trifluoromethyl) phenoxy group)-N-mesyl-2-

Nitrobenzamide fosamine hydrogen (aminocarbonyl) etherophosphoric acid glyphosate N-((phosphonomethyl)) glycine haloxyfop 2-(4-((3-chloro-5-(trifluoromethyl)-2-pyridine radicals) oxygen) benzene

The oxygen base) propionic acid potassium hexafluoroarsenate potassium hexafluoroarsenate hexazinone 3-cyclohexyl-6-dimethylamino-1-methyl isophthalic acid, 3,5-triazine-2,4 (1H,

3H)-diketone imazamethabenz 6-(4-isopropyl-4-methyl-5-oxygen-2-imidazoline-2-yl) between the toluene first

Acid methyl esters and 6-(4-isopropyl-4-methyl-5-oxygen-2-imidazoline-2-

Base) methyl p toluate imazapyr (±)-2-(4, the 1-Methylethyl of 5-dihydro-4-methyl-4-))-5-oxygen

-1H-imidazoles-2-yl)-and 3-pyridine carboxylic acid imazaquin 2-(4,5-dihydro-4-methyl-4-(1-Methylethyl)-5-oxygen-1H-miaow

Azoles-2-yl)-3-quinolinecarboxylic acid imazethapyr (±)-2-(4,5-dihydro-4-methyl-4-(1-Methylethyl)-5-oxygen-

1H-imidazoles-2-yl)-5-ethyl-3-pyridine carboxylic acid iodine oxalic acid dinitrile 4-hydroxyl-3,5-diiodo-benzonitrile isopropalin 4-(1-Methylethyl)-2,6-dinitro-N, N-dipropyl aniline isoproturon N-(4-isopropyl phenyl)-N ', N '-dimethyl urea isouron N '-(5-(1, the 1-dimethyl ethyl)-the 3-isoxazolyl)-N, N-two

Methyl urea isoxaben N-(3-(1-ethyl-1-methyl-propyl)-5-isoxazolyl)-2,6-two

Methoxy benzamide Te Weilong (1, the 1-dimethyl ethyl) carbamic acid 3-(((dimethylamino) carbonyl)

Amino) phenylester lactofen (±) 5-(2-chloro-4-(trifluoromethyl) phenoxy group)-2-nitrobenzoyl

Acid 2-ethyoxyl-1-methyl-2-oxoethyl ester lenacil 3-cyclohexyl-6,7-dihydro-1H-encircle penta pyrimidine-2,4 (3H, 5H)-

Diketone lorox N '-(3, the 4-dichlorophenyl)-and mono-ammonium 2 first 4 chlorine (4-chloro-2-methylphenoxy) acetate Thistrol 4-(4-chloro-2-methylphenoxy) butyric acid MON 7200 2-(difluoromethyl)-4-(2-methyl-propyl)-6-(trifluoromethyl)-3 of N-methoxyl group-N-methyl urea methylarsonic acid methylarsonic acid arsine grass ammonium methylarsonic acid, 5-

Pyridine sulfo-dioctyl phthalate S; S-dimethyl ester Vi par (±)-2-(4-chloro-2-methylphenoxy) propionic acid mefenacet 2-(2-[4-morpholinodithio base) oxygen-N-methyl-phenyl acetanilide,Phenacetylaniline mefluidide N-(2,4-dimethyl-5-(((trifluoromethyl) sulfonyl) amino)

Phenyl) acetamide methalpropalin N-(2-methyl-2-acrylic)-2,6-dinitro-N-propyl group-4-(trifluoro

Methyl) the benzamide methabenz thiazuron 1, and 3-dimethyl-3-(2-[4-morpholinodithio base) urea Carbathiin methyl aminodithioformic acid is Dinged Cao Evil 2-(3, the 4-dichlorophenyl)-4-methyl isophthalic acid, and 2,4-oxadiazole alkane-3,5-two

Ketone methoxuron N '-(3-chloro-4-methoxyphenyl)-N, N-dimethyl urea metribuzin 4-amino-6-(1, the 1-dimethyl ethyl)-3-methyl mercapto-1,2, the 4-diazine-

5 (4H) ketone maleic hydrazide 1,2-dihydro 3,6-pyridazine diketone molinate hexahydro-1 H-azepines-1-bamic acid S-ethyl ester one chlorine lorox 3-(rubigan)-1-methoxyl group-1-methyl urea monuron N '-(4-chlorphenyl)-N, single sodium salt naphthalene third peace N of the salt Ansar methylarsonic acid of N-dimethyl urea monuron trichloroacetic acid monuron and trichloroacetic acid, the grand 1-butyl-3-(3 of N-diethyl-2-(1-naphthoxy) propionamide alanap 2-((1-naphthylamino) carbonyl) benzoic acid fourth enemy, the 4-dichlorophenyl)-1-methyl urea nicosulfuron 2-(((4,6-dimethoxy-pyridine-2-yl) amino carbonyl) amino sulphur

Acyl group)-N; the happy clever 4-mesyl-2 of N-dimethyl-3-pyridine carboxamide first sulfone; 6-dinitro-N; N-dipropyl aniline nitrofen 2; 4-two chloro-1-(4-nitrophenoxy) benzene nitrofluorfen 2-chloro-1-(4-nitrophenoxy)-4-(trifluoromethyl) benzene norea N; N-dimethyl-N '-(octahydro-4,7-methylene-1H-indenes-5-yl)

Urea 3a α ,-4 α, 5 α, 7 α, 7a αYi Gouti fluorine pyridazone 4-chloro-5-methylamino-2-(3-(trifluoromethyl) phenyl)-3 (2H)-rattle away

Piperazine ketone sulphur dipropalin 4-(dipropyl amino)-3, (2,4-two chloro-5-(1-methyl ethoxy) phenyl)-(1,1-two for 5-for the careless Evil 3-of 5-dinitro benzene sulfonamide pine

Methylethyl)-1; 3; 4-oxadiazole-2 (3H)-ketone oxyfluorfen 2-chloro-1-(3-ethyoxyl-4-nitrophenoxy)-4-(trifluoromethyl) benzene paraquat 1; 1 '-dimethyl-4; 4 '-bipyridine cation restrains careless red butyl ethyl thiocarbamic acid S-propyl ester pendimethalin N-(1-ethyl propyl)-3; 4-dimethyl-2; 6-dinitroaniline benzene fluorine sulphur peace 1; 1,1-three fluoro-N-(2-methyl-4-(benzenesulfonyl) phenyl) first sulphur

Acid amides first two Wheelings (3-aminomethyl phenyl) carbamic acid 3-((methoxycarbonyl group) amino) phenyl

The ester poisonous weeds are decided 4-amino-3,5,6-three chloro-2-pyridine carboxylic acid PPG-1013 5-(2-chloro-4-(trifluoromethyl) phenoxy group)-2-nitro-acetophenone oximes

-O-methyl acetate third careless amine α-chloro-2,6-diethyl-N-(the 2-third oxygen ethyl)-monoacetylaniline procyazine 2-((4-chloro-6-(cyclopropylamino)-1,3,5-triazines-2-yl) amino)

-2-methyl propionitrile ring third trefanocide the N-(cyclopropyl methyl)-2,6-dinitro-N-propyl group-4-(fluoroform

Base) aniline prometryn 6-methoxyl group-N, N '-two (1-Methylethyl)-1,3,5-triazines-2,4-

Diamines prometryn N, N '-two (1-Methylethyl)-6-methyl mercapto-1,3,5-triazines-

2,4-diamines alkynes Stam F-34 3,5-two chloro-N-(1,1-dimethyl-2-propynyl) benzamide propachlor 2-chloro-N-(1-Methylethyl)-phenyl acetanilide,Phenacetylaniline Stam F-34 N-(3, the 4-dichlorophenyl) propionamide propazine 6-chloro-N, N '-two (1-Methylethyl)-1,3,5-triazine-2,4-two

Amine propham phenylcarbamic acid 1-Methylethyl ester methyl mercapto nitralin H-((4-(dipropyl amino)-3,5-dinitrophenyl) sulfonyl)

-S, S-dimethyl disulfide imines butine propachlor 2-chloro-N-(1-methyl-2-propynyl)-monoacetylaniline pyrazo1ate p-methyl benzenesulfonic acid 4-(2,4 dichloro benzene formoxyl)-1,3-dimethyl pyrazole

Azoles-5-base ester is warded off pyridazone 5-amino-4-chloro-2-phenyl-3 (2H)-pyridazinone quinclorae 3,7-two chloro-8-quinolinecarboxylic acid quizalofop ethyl (±)-2-(4-((6-chloro-2-quinoxalinyl) oxygen) phenoxy group) third

The logical N-ethyl of other fourth of acetoacetic ester-6-methoxyl group-N '-(1-methyl-propyl)-1,3,5-triazines-

2,4-diamines sethoxydim 2-(1-(ethoxy imino) butyl)-5-(2-(ethylmercapto group) third

Base)-the grand N-(2-methylcyclohexyl) of 3-hydroxyl-2-cyclohexene-1-ketone hexamethylene-N '-phenylurea Simanex 6-chloro-N, N '-diethyl-1,3,5-triazine-2,4-diamines SK-233 1-(α, α-Er Jiajibianji)-3-(4-aminomethyl phenyl) urea Sulfometuron 2-(((((4,6-dimethyl-2-pyrimidine radicals) amino) carbonyl) ammonia

Basic) sulfonyl) methyl benzoate trichloroacetic acid trichloroacetic acid tebuthiuron N-(5-(1, the 1-dimethyl ethyl)-1,3,4-thiadiazoles-2-yl)-

N, and the special chlorine pyridine 5-chloro-3-(1, the 1-dimethyl ethyl) of N '-dimethyl urea-6-methyl-2,4 (1H, 3H)-pyrimidine

Diketone terbuchlor N-(fourth oxygen methyl)-2-chloro-N-(2-(1, the 1-dimethyl ethyl)-6-first

The base phenyl) acetamide Garagard uncle 2-fourth amino-4-chloro-6-ethylamino s-triazine Azac methyl carbamic acid 2, the clean N-(1 of the special fourth grass of 6-di-t-butyl p-methylphenyl ester, the 1-dimethyl ethyl)-N '-ethyl-6-methyl mercapto-1,3,5-

Triazine-2,4-diamines thifensulfuron methyl 3-(((((4-methoxyl group-6-methyl isophthalic acid, 3,5-triazine-2-yl) ammonia

Base) sulfonyl amino carbonyl)))-two (1-Methylethyl) the thiocarbamic acid S-(2 of 2-thiophenecarboxylate thiobencarb diethyl thiocarbamic acid S-((4-chlorphenyl) methyl) ester triallate; 3,3-three chloro-2-third

Thiazolinyl) ester tribenuron methyl 2-((((N-(4-methoxyl group-6-methyl isophthalic acid, 3,5-triazine-2-yl)-N-

Methylamino) methyl benzoate second daxtron ((3 sulfonyl amino carbonyl))); 5; the 6-trichloro-2-pyridyl) acetate tridiphane 2-(3 oxygen); the 5-dichlorophenyl)-2-(2; 2; 2-three chloroethyls) oxirane trefanocide 2; 6-dinitro-N; N-dipropyl-4-(trifluoromethyl) aniline trimeturon 1-rubigan-2; 3; 3-trimethyl pseudo-urea 2; 4-drips (2,4 dichloro benzene oxygen base) acetate 2,4-Embutox 4-(2; the 4-dichlorophenoxy) the red dipropyl thiocarbamic acid S-propyl diester Xylachlor 2-chloro-N-(2, the 3-3,5-dimethylphenyl) of butyric acid weed eradication-N-(1-Methylethyl) acetamide

In some greenhouse tests, found the herbicidal properties of motif compound.Test procedure and result are as follows.

Test A

A part of sandy loam of packing in plastic flowerpot, water makes soil saturation then.Divide two bunches of japonica rice (Oryza sativa) seedlings (every bunch 3 strain seedling) of transplanting the 1.5 leaf phases of 6 strains in this soil, implantation depth is 2cm.In the 1.0cm soil of top, broadcast seed into barnyard grass.Be implanted into the arrowhead stem tuber at soil, implantation depth is 0.5cm.Horizontal plane brought up to exceed soil surface 3cm, and in whole test, keep this level.Handle of the solvent preparation of the compound of usefulness with plant-less toxicity, and after rice is transplanted 5 days, just implant arrowhead after and barnyard grass be in 1.5 leaves during the phase, directly be applied in the flowerpot water.

Processed group plant and adjoining tree were kept in the greenhouse 21 days, then with plant and relatively also range estimation grading of control group.Measure the weight of rice plants shoot in each flowerpot.The plant reaction grade is summarized in table 1 and table 2, represents than the percentage that the untreated control group descends with rice plants shoot weight.The range estimation grade of barnyard grass is summarized in table 3, and the range estimation grade of arrowhead is summarized in table 4, all represents with the yardstick of 0-100, and wherein 0 is harmless, and 100 are control fully.

Table 1

Due to Compound I a handles usefulness Compound I Ia

The detoxification ability compound administration rate % rice infringement of rice infringement

(gram active component/hectare) experimental value expected value ⁽¹⁾IIa 100 33 -IIa 200 45 -IIa＋Ia 100＋5 35 34IIa＋Ia 100＋10 21 41IIa＋Ia 100＋20 20 34IIa＋Ia 200＋5 39 46IIa＋Ia 200＋10 25 52IIa＋Ia 200＋20 28 46Ia 5 2 -Ia 10 12 -Ia 20 2 -

1, calculates rice infringement value by Cole than equation with the infringement value of each weed killer herbicide respectively.Be used to calculate the Cole of synergistic effect than equation following (Co1by, S.R., Weeds, 15:20-22,1967):

E＝A＋B－A×B/100

The E=expected value

The experimental value of A=Compound I Ia

The experimental value of B=Compound I a

For example

In the table 1: the experimental value 45% of A=200 gram/hectare IIa

The experimental value 2% of B=5 gram/hectare Ia

E＝45％+2％－45％×2％/100

E＝46％

Table 2

Compounds ib, Ic and Ia+Ic are to using compound

The detoxification ability compound administration rate % rice infringement of rice infringement due to IIa handles

(gram active component/hectare) experiment value desired value IIa 75 32-IIa+Ib 7,5+5 18 36IIa+Ib 75,+10 19 36IIa+Ib 75,+20 21 38Ib 5 7-Ib 10 6-Ib 20 10-IIa+Ic 7,5+1 15 38IIa+Ic 7,5+2 26 41Ic 1 7-Ic 2 14-IIa+Ia+Ic 75+,5+1 9 39IIa+Ia+Ic 7,5+1,0+2 28 37Ia+Ic 5+1 12-Ia+Ic 1,0+2 8-

Table 3

Compound I a is to the compound administration rate that the influences activity of Compound I Ia control barnyard grass activity

(gram active component/hectare) experiment value desired value IIa 100 95-IIa 200 100-IIa+Ia 10,0+5 98 95IIa+Ia 100,+10 95 96IIa+Ia 100,+20 98 97IIa+Ia 20,0+5 98 100IIa+Ia 200,+10 100 100IIa+Ia 200,+20 100 100Ia 5 0-Ia 10 20-Ia 20 30-

Table 4

Compound I Ia is to the compound administration rate that the influences activity of Compound I a control arrowhead activity

(gram active component/hectare) experiment value desired value IIa 100 0-IIa 200 0-IIa+Ia 10,0+5 30 0IIa+Ia 100,+10 65 70IIa+Ia 100,+20 80 80IIa+Ia 20,0+5 50 0IIa+Ia 200,+10 60 70IIa+Ia 200,+20 75 80Ia 5 0-Ia 10 70-Ia 20 80-

Claims (5)

1. control the agricultural composition that is suitable for that undesirable plant is grown in the rice class crop for one kind, said composition comprise the formula IIc compound of 0.01-5kg/ hectare and 0.0005-1kg/ hectare one or more be selected from the sulfonyl urea compound of formula Ia-Ie, and they are suitable for agricultural salt: 2-chloro-N-(ethoxyethyl group)-N-(2-ethyl-6-aminomethyl phenyl) acetamide (metolachlor);

2-((((((4,6-dimethoxy-2-pyrimidine radicals) amino) carbonyl) amino) sulfonyl) methyl) methyl benzoate (bensulfuron-methyl);

5-(((((4,6-dimethoxy-2-pyrimidine radicals) amino) carbonyl) amino) sulfonyl)-1-methyl isophthalic acid H-pyrazoles-4-Ethyl formate (ethyl pyrazoles sulphur is grand);

2-(((((4-methoxyl group-6-methyl isophthalic acid, 3,5-triazine-2-yl) amino) carbonyl) amino) sulfonyl) methyl benzoate (metsulfuron-methyl); 2-(((((4-chloro-6-methoxyl group-2-pyrimidine radicals) amino) carbonyl) amino) sulfonyl) ethyl benzoate (ethyl chloride Sulfometuron Methyl); N-(((4,6-dimethoxy-2-pyrimidine radicals) amino) carbonyl)-1-methyl-4-(2-methyl-2H-tetrazolium-5-yl)-1H-pyrazoles-5-sulfonamide; Its prerequisite is:

If a) only contain a kind of sulfonylureas among the formula Ia-Ie in the herbicidal composition, then this sulfonylureas is not Id (an ethyl chloride Sulfometuron Methyl);

Described composition also comprises at least a following material: surfactant, solid diluent or liquid diluent.

2. the herbicidal composition of claim 1, wherein sulfonyl urea compound is formula Ia.

3. the herbicidal composition of claim 1, wherein sulfonyl urea compound is formula Ic.

4. the herbicidal composition of claim 1, wherein sulfonyl urea compound is formula Ia and Ic.

5. the method for undesirable plant growth in the control rice class crop in, this method comprise, to each composition among the claim 1-4 of rice class crop applying herbicidally effective amount.