CN1064986A

CN1064986A - The Herbicidal mixtures that contains sulfonylurea and monoacetylaniline class

Info

Publication number: CN1064986A
Application number: CN 92101836
Authority: CN
Inventors: 杨永胜; 李普; 王焕明; 惠兆香; 柳元虎
Original assignee: EI Du Pont de Nemours and Co
Current assignee: EIDP Inc
Priority date: 1991-03-19
Filing date: 1992-03-19
Publication date: 1992-10-07
Also published as: CN1145723A

Abstract

The present invention relates to the agricultural composition that is suitable for of some sulfonylurea and monoacetylaniline class, and they are as the using method that is used for the selective herbicide of rice with herbicide effect.

Description

The Herbicidal mixtures that contains sulfonylurea and monoacetylaniline class

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, a general field 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 fourth grass lock and the isobutyl grass lock monoacetylaniline classes such as (pretilachlor):

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.

U.S.4,645,530 disclose ethyl chloride wood grand (chlorimuron eth-yl) 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 were both not open, and also hint is not detoxified to the rice infringement that formula II monoacetylaniline class causes with formula I sulfonylurea.

The present invention relates to some herbicidal compositions, these compositions comprise one or more formula I a-I e sulfonyl urea compound of herbicidally effective amount and a kind of formula II a-II c monoacetylaniline compounds of 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 present invention relates to protect rice to avoid the method for formula II a-II c monoacetylaniline class weed killer herbicide infringement; this method comprises; with the described monoacetylaniline class weed killer herbicide of herbicidally effective amount and one or more formula I a-I e sulfonylureas of herbicidally effective amount, combined administration is in rice plants or rice plants place.Formula I a-I e sulfonylurea and formula II a-II c monoacetylaniline class are following compound and are suitable for agricultural salt:

（Ⅰa）

(I a) for methylbenzene sulphur grand (bensulfuron methyl) for 2-((((((4,6-dimethoxy-2-pyrimidine radicals) amino) carbonyl) amino) sulfonyl) methyl) methyl benzoate;

（Ⅰb）

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

（Ⅰc）

2-(((((4-methoxyl group-6-methyl isophthalic acid, 3,5-triazine-2-yl) amino) carbonyl) amino) sulfonyl) methyl benzoate (methyl first sulphur swells (metsulfuron methyl), I c);

（Ⅰd）

2-(((((4-chloro-6-methoxyl group-2-pyrimidine radicals) amino) carbonyl) amino) sulfonyl) ethyl benzoate (ethyl chloride wood grand (chlorimuron ethyl), I d);

（Ⅰe）

N-(((4,6-dimethoxy-2-pyrimidine radicals) amino) carbonyl)-1-methyl-4-(2-methyl-2H-tetrazolium-5-yl)-1H-pyrazoles-5-sulfonamide (I e);

（Ⅱa）

2-chloro-N-(2-ethyl-6-aminomethyl phenyl)-N-(2-methoxyl group-1-Methylethyl) acetamide (metolachlor, II is a);

（Ⅱb）

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

（Ⅱc）

2-chloro-N-(ethoxyethyl)-and N-(2-ethyl-6-aminomethyl phenyl) acetamide (metolachlor, II c);

Its prerequisite is:

If a) herbicidal composition only contains a kind of formula I sulfonylureas, then this sulfonylureas is not an ethyl chloride wood grand (I d);

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

Preferred composition of the present invention comprises:

1, a kind of herbicidal composition, it comprises one or more formula I a-I e sulfonylureas and as the metolachlor of formula II a monoacetylaniline.

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

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

4, a kind of herbicidal composition of preferred composition 1, wherein sulfonylureas is a formula I c compound, promptly methyl first sulphur is grand.

5, a kind of herbicidal composition of preferred composition 1, wherein sulfonylureas is a formula I a compound, promptly methylbenzene sulphur is grand.

6, a kind of herbicidal composition of preferred composition 1, wherein sulfonylureas is that formula I a compound is that methylbenzene sulphur swells and formula I c compound is that methyl first sulphur is grand.

7, a kind of herbicidal composition of preferred composition 1, wherein sulfonylureas is that formula I c compound is that methyl first sulphur swells and formula I d compound is that ethyl chloride wood is grand.

8, a kind of method of controlling undesirable plant in the rice, this method comprise, use a kind of formula I a-I e sulfonylureas of herbicidally effective amount and a kind of formula II a-II c monoacetylaniline of herbicidally effective amount.

The most preferred composition of the present invention is the herbicidal composition of formula II a and I a and the herbicidal composition of formula II a and I b.

The sulfonylurea of formula I a-I e 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 several sprayed volume that rise to several hectolitres of per hectare.High concentration composition is mainly as the intermediate for further preparation usefulness.Put it briefly, these preparations contain the 0.1-99%(weight of having an appointment) 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 thinner surfactant

Wetting powder 20-90 0-74 1-10

Oil-suspending agent, emulsion, 3-50 40-95 0-15

Solution (comprising missible oil)

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 composition 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 Publishing Corp., 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 all can contain 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.Erowning, " agglomeration ", Chemical Engineering, 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, 3,235,361,1966, 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 the 43rd 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 ", John Wiley 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 Control Handbook ", Blackwell 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%

Methylbenzene sulphur grand 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%

Methylbenzene sulphur grand 5%

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

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%

Methylbenzene sulphur grand 2.5%

Methyl first sulphur grand 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%

Methylbenzene sulphur grand 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

Methyl first sulphur grand 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%

Methyl first sulphur grand 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 I a-I e compound can be used for improving the tolerance of rice class crop to formula II a-II c 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 formula I a-I e compound and a kind of formula II a-II e compound combined administration in the plant place, can be realized agricultural weed control and crop safety.Formula I a-I e compound can be avoided infringement that formula II a-II c 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 I a-I e weed killer herbicide can be prepared with formula II a-II c 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 I a-I e compound and formula II a-II c 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, the rate of application of formula I a-I e weed killer herbicide should be 0.0005-1 kilogram active component/hectare, and the rate of application of formula II a-II c weed killer herbicide should be 0.01-5 kilogram active component/hectare.This area professional determines to reach the rate of application that weeds are controlled and crop safety is required of expection level and the ratio of formula I a-I e weed killer herbicide and formula II a-II c weed killer herbicide easily.

Herbicidal composition of the present invention can use separately, also can mix use 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.

The popular name chemical name

Acifluorfen 5-(2-chloro-4-(trichloromethyl) phenoxy group)-the 2-nitrobenzoic acid

Acrolein 2-acrolein

Anilofos S-4-chloro-N-cumene carbamyl methyl-O, O-Methyl disulfide substituted phosphate

Aunar draws clean N-ethyl-N '-(1-Methylethyl)-6-methyl mercapto-1,3,5-triazines-2,4-diamines

Aminotriazole 1H-1,2,4-triazole-3-amine

The Amcide Ammate Amcide Ammate

Asulam ((4-aminophenyl) sulfonyl) methyl carbamate

Atrazine 6-chloro-N-ethyl-N '-(1-Methylethyl)-1,3,5-triazines-2, the 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) ethyl) phosphorodithioates of O-

Bentazon 3-(1-Methylethyl)-(1H)-2,1, the 3-benzothiadiazine-4(3H)-and ketone 2, the 2-dioxide

Benzofluor N-(4-ethylmercapto group-2-(trifluoromethyl) phenyl) Methanesulfomide

Suffer N-benzoyl-N-(3, the 4-dichlorophenyl)-DL-alanine

Methyl esters nitrofen 5-(2, the 4-dichlorophenoxy)-2-nitrobenzoic acid methyl esters

Bromacil 5-bromo-6-methyl-3-(1-methyl-propyl)-2,4(1H, 3H) hybar X

Bromoxynil 3,5-two bromo-4-hydroxy-phenylformonitriles

Fourth grass lock N-(fourth oxygen methyl)-and 2-chloro-N-(2,6-diethyl phenyl) acetamide

Fourth sulphur imidazolone 3-(5-(1,1-dimethyl ethyl)-1,3,4-thiadiazoles-2-yl)-4-hydroxyl-1-methyl-2-imidazolone

Ding Leling 4-(1, the 1-dimethyl ethyl)-the N-(1-methyl-propyl)-2, the 6-dinitroaniline

Two (2-methyl-propyl) the thiocarbamic acid S-ethyl esters of Butilate

The swollen acid of Phytar dimethyl

Alkene grass 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-triazines-2-yl)-1-(2-(2-methoxy ethoxy) benzenesulfonyl) urea

Chloramben 3-amino-2, the 5-dichlorobenzoic acid

Chlorine metobromuron 3-(4-bromo-3-chlorphenyl)-1-methoxyl group-1-methyl urea

Chlormethoxynil 2,4 dichloro benzene base-4-nitro-3-methoxyphenyl ether

Mo 9 granular 2,4,6-trichlorophenyl-4-nitrobenzophenone ether

Chloroxuron N '-(4-(4-chlorophenoxy) phenyl)-and N, the N-dimethyl urea

Chlorpropham 3-chlorphenyl carbamic acid 1-Methylethyl ester

Chlorsulfuron 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, the N-dimethyl urea

Cinmethylin extroversion-1-methyl-4-(1-Methylethyl)-2-((2-aminomethyl phenyl) methoxyl group)-7-oxabicyclo (2.2.1) heptane

Clethodim (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

Clomazone 2-((2-chlorphenyl) methyl)-4,4-dimethyl-3-isoxazole alkyl ketone

Cloproxydim (E, E)-2-(1-(((3-chloro-2-acrylic) oxygen) imino group) butyl)-5-(2-(ethylmercapto group) propyl group)-3-hydroxyl-2-cyclohexene-1-ketone

Clopyralid 3,6-two chloro-2-Pyridinecarboxylic Acids

The calcium salt of the swollen acid of the swollen sour calcium first of first

Cyanazine 2-((4-chloro-6-ethylamino-1,3,5-triazines-2-yl) amino)-2-methyl propionitrile

Cycloate cyclohexyl ethylenebis dithiocarbamate carbamic acid S-ethyl ester

The hot grand 3-ring octyl group-1 of ring, the 1-dimethyl urea

The fast 1-methyl-4-phenylpyridinium cation of benzene grass

Cyprazine 2-chloro-4-(cyclopropyl amino)-and 6-(isopropyl amino) s-triazine

Encircle luxuriant peace N-(5-(2-chloro-1,1-dimethyl ethyl)-1,3,4-thiadiazoles-2-yl) cyclopropane carboxamide

Encircle the third Stam F-34 N-3 ', 4 '-dichloro cyclopropane-carboxylic acid anilide

Dalapon 2, the 2-dichloropropionic acid

Dazomet tetrahydrochysene-3,5-dimethyl-2H-1,3,5-thiadiazine-2-thioketones

Dcpa 2,3,5,6-tetrachloro-1,4-rutgers

Sweet grass spirit (3-(((phenylamino) carbonyl) oxygen) phenyl) urethanes

Desmetryn 2-(isopropyl amino)-4-methylamino-6-methyl mercapto s-triazine

Red two (1-Methylethyl) the thiocarbamic acid S-(2 of dichloro alkene, 3-two chloro-2-acrylic) ester

Dianat 3,6-two chloro-O-Anisic Acids

Dichlobenil 2, the 6-dichlorobenzonitrile

2,4-drips propionic acid (±)-2-(2, the 4-dichlorophenoxy) propionic acid

2,4-drips methyl phenylpropionate (±)-2-(4-(2,4-dichlorophenoxy) phenoxy group) methyl propionate

Diethatyl N-(chloracetyl)-and N-(2,6-diethyl phenyl) glycine

Ion grass pyrazoles 1,2-dimethyl-3,5-diphenyl-1H-pyrazoles cation

Dimepiperate piperidines-1-bamic acid S-1-methyl isophthalic acid-phenethyl ester

The happy amine N of diethyl fluorine ³, N ³-diethyl-2,4-dinitro-6-(trifluoromethyl)-1, the 3-phenylenediamine

Dinoseb 2-(1-methyl-propyl)-4, the 6-dinitrophenol

Diformazan acetyldiphenylamine N, N-dimethyl-α-Ben Jibenyixian amine

Dipropetryn 6-ethylmercapto group-N, N '-two (1-Methylethyl)-1,3,5-triazines-2,4-diamines

Diquat 6,7-dihydrodi pyridine also (1,2-a:2 ', 1 '-c) the pyrazine cation

Diuron N '-(3, the 4-dichlorophenyl)-N, the N-dimethyl urea

Dnoc 2-methyl-4, the 6-dinitrophenol

The disodium salt of the swollen acid of the swollen disodium first of first

Sand-grass is swelled the N-(4-aminomethyl phenyl)-N '-(1-methyl isophthalic acid-phenylethyl) urea

Aquathol 7-oxabicyclo (2.2.1) heptane-2, the 3-dioctyl phthalate

EPTC dipropyl thiocarbamic acid S-ethyl ester

Esprocarb N-ethyl-N-(1, the 2-dimethyl) propyl group)

(SC2957) thiocarbamic acid S-benzyl ester

Alkene trefanocide N-ethyl-N-(2-methyl-2-acrylic)-2,6-dinitro-4-(trifluoromethyl) aniline

Ethofumesate (±) methanesulfonic acid 2-ethyoxyl-2,3-dihydro-3,3-dimethyl-5-benzofuranyl ester

Fenac 2,3, the 6-chlorfenac

Fenoxaprop (±)-2-(4-((6-chloro-2-benzoxazolyl) oxygen) phenoxy group) propionic acid

Fenuron N, N-dimethyl-N '-phenylurea

The salt of fenuron trichloroacetic acid fenuron and trichloroacetic acid

Flamprop N-benzoyl-N-(3-chloro-4-fluorophenyl)-DL-alanine

Fluazifop (±)-2-(4-((5-(trifluoromethyl)-2-pyridine radicals) oxygen) phenoxy group) propionic acid

Fluazifop-P (R)-2-(4-((5-(trifluoromethyl)-2-pyridine radicals) oxygen) phenoxy group) propionic acid

Fluchloralin N-(2-chloroethyl)-2,6-dinitro-N-propyl group-4-(trifluoromethyl) aniline

Fluometuron N, N-dimethyl-N '-(3-(trifluoromethyl) phenyl) urea

Fluorcchloridone 3-chloro-4-(chloromethyl)-1-(3-(trifluoromethyl) phenyl)-2-Pyrrolidone

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 carboxymethyl ester

Fluriaone 1-methyl-3-phenyl-5-(3-(trifluoromethyl) phenyl)-4(1H)-pyridone

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) phenoxy group) propionic acid

The 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) methyl p toluate meta-toluic acid methyl esters and 6-(4-isopropyl-4-methyl-5-oxygen-2-imidazoline-2-yl)

Imazapyr (±)-2-(4,5-dihydro-4-methyl-4-(1-Methylethyl)-5-oxygen-1H-imidazoles-2-yl)-the 3-pyridine carboxylic acid

Imazaquin 2-(4,5-dihydro-4-methyl-4-(1-Methylethyl)-5-oxygen-1H-imidazoles-2-yl)-the 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)-and N ', N '-dimethyl urea

Isouron N '-(5-(1,1-dimethyl ethyl)-3-isoxazolyl)-and N, the N-dimethyl urea

Isoxaben N-(3-(1-ethyl-1-methyl-propyl)-5-isoxazolyl)-2,6-dimethoxy benzamide

Te Weilong (1, the 1-dimethyl ethyl) carbamic acid 3-(((dimethylamino) carbonyl) amino) phenylester

Lactofen (±) 5-(2-chloro-4-(trifluoromethyl) phenoxy group)-2-nitrobenzoic acid 2-ethyoxyl-1-methyl-2-oxoethyl ester

Lenacil 3-cyclohexyl-6,7-dihydro-1H-encircles penta pyrimidine-2,4(3H, 5H)-diketone

Lorox N '-(3, the 4-dichlorophenyl)-N-methoxyl group-N-methyl urea

The swollen acid of methylarsonic acid first

The mono-ammonium of arsine grass ammonium methylarsonic acid

2 first, 4 chlorine (4-chloro-2-methylphenoxy) acetate

Thistrol 4-(4-chloro-2-methylphenoxy) butyric acid

MCN 7200 2-(difluoromethyls)-the 4-(2-methyl-propyl)-the 6-(trifluoromethyl)-3,5-pyridine sulfo-dioctyl phthalate S, S-dimethyl ester

Vi par (±)-2-(4-chloro-2-methylphenoxy) propionic acid

Mefenacet 2-(2-benzothiazolyl 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-(trifluoromethyl) benzamide

Methabenz thiazuron 1,3-dimethyl-3-(2-benzothiazolyl) urea

Carbathiin methyl aminodithioformic acid

Ding Cao Evil 2-(3, the 4-dichlorophenyl)-the 4-methyl isophthalic acid, 2,4-oxadiazole alkane-3,5-diketone

Methoxuron N '-(3-chloro-4-methoxyphenyl)-N, the N-dimethyl urea

Metribuzin 4-amino-6-(1, the 1-dimethyl ethyl)-3-methyl mercapto-1,2, the 4-triazine-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, the N-dimethyl urea

The salt of monuron trichloroacetic acid monuron and trichloroacetic acid

Single sodium salt of the swollen sodium methylarsonic acid of first

The naphthalene third peace N, N-diethyl-2-(1-naphthoxy) propionamide

Alanap 2-((1-naphthylamino) carbonyl) benzoic acid

The grand 1-butyl-3-(3 of fourth enemy, the 4-dichlorophenyl)-1-methyl urea

Nicosulfuron 2-(((4,6-dimethoxy-pyridine-2-yl) amino carbonyl) amino-sulfonyl)-N, N-dimethyl-3-pyridine carboxamide

The happy clever 4-mesyl-2 of first sulfone, 6-dinitro-N, N-dipropyl aniline

Nitrofen 2,4-two chloro-1-(4-nitro-phenoxies) benzene

Nitrofluorfen 2-chloro-1-(4-nitro-phenoxy)-and the 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)-pyridazinone

Sulphur dipropalin 4-(dipropyl amino)-3,5-dinitro benzene sulfonamide

Pine careless Evil 3-(2,4-two chloro-5-(1-methyl ethoxies) phenyl)-and 5-(1, the 1-dimethyl ethyl)-1,3, the 4-oxadiazole-2(3H)-ketone

Oxyfluorfen 2-chloro-1-(3-ethyoxyl-4-nitrophenoxy)-and the 4-(trifluoromethyl) benzene

Paraquat 1,1 '-dimethyl-4,4 '-bipyridine cation

Restrain 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) Methanesulfomide

First two Wheelings (3-aminomethyl phenyl) carbamic acid 3-((methoxycarbonyl group) amino) phenylester

Poisonous weeds are decided 4-amino-3,5,6-three chloro-2-pyridine carboxylic acids

PPG-1013 5-(2-chloro-4-(trifluoromethyl) phenoxy group)-2-nitro-acetophenone oxime-O-methyl acetate

Pretilachlor α-chloro-2,6-diethyl-N-(2-third oxygen ethyl)-monoacetylaniline

Procyazine 2-((4-chloro-6-(cyclopropylamino)-1,3,5-triazines-2-yl) amino)-2-methyl propionitrile

Encircle the third trefanocide N-(cyclopropyl methyl)-2,6-dinitro-N-propyl group-4-(trifluoromethyl) 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-triazines-2,4-diamines

Propham phenylcarbamic acid 1-Methylethyl ester

Methyl mercapto nitralin N-((4-(dipropyl amino)-3,5-dinitrophenyl) sulfonyl)-and S, S-dimethyl disulfide imines

Butine propachlor 2-chloro-N-(1-methyl-2-propynyl)-monoacetylaniline

Pyrazolate p-methyl benzenesulfonic acid 4-(2,4-dichloro-benzoyl base)-1,3-dimethyl pyrazole-5-base ester

Ward off pyridazone 5-amino-4-chloro-2-phenyl-3(2H)-pyridazinone

Quinclorac 3,7-two chloro-8-quinolinecarboxylic acids

Quizalofop ethyl (±)-2-(4-((6-chloro-2-quinoxalinyl) oxygen) phenoxy group) ethyl propionate

Fourth is led to N-ethyl-6-methoxyl group-N '-(1-methyl-propyl)-1,3,5-triazines-2,4-diamines in addition

Sethoxydim 2-(1-(ethoxy imino) butyl)-5-(2-(ethylmercapto group) propyl group)-3-hydroxyl-2-cyclohexene-1-ketone

Hexamethylene swells the N-(2-methylcyclohexyl)-N '-phenylurea

Simanex 6-chloro-N, N '-diethyl-1,3,5-triazines-2,4-diamines

SK-233 1-(α, α-Er Jiajibianji)-the 3-(4-aminomethyl phenyl) urea

Sulfometuron methyl 2-(((((4,6-dimethyl-2-pyrimidine radicals) amino) carbonyl) amino) sulfonyl) methyl benzoate

The trichloroacetic acid trichloroacetic acid

Tebuthiuron N-(5-(1,1-dimethyl ethyl)-1,3,4-thiadiazoles-2-yl)-N, N '-dimethyl urea

Special chlorine pyridine 5-chloro-3-(1, the 1-dimethyl ethyl)-6-methyl-2,4(1H, 3H)-hybar X

Terbuchlor N-(fourth oxygen methyl)-and 2-chloro-N-(2-(1,1-dimethyl ethyl)-6-aminomethyl phenyl) acetamide

Garagard uncle 2-fourth amino-4-chloro-6-ethylamino s-triazine

Azac methyl carbamic acid 2,6-di-t-butyl p-methylphenyl ester

The clean N-(1 of special fourth grass, the 1-dimethyl ethyl)-N '-ethyl-6-methyl mercapto-1,3,5-triazines-2, the 4-diamines

Thifensulfuron methyl 3-(((((4-methoxyl group-6-methyl isophthalic acid, 3,5-triazine-2-yl) amino) carbonyl) amino) sulfonyl)-2-thiophenecarboxylate

Thiobencarb diethyl thiocarbamic acid S-((4-chlorphenyl) methyl) ester

Two (1-Methylethyl) the thiocarbamic acid S-(2 of triallate, 3,3-three chloro-2-acrylic) ester

Tribenuron methyl 2-((((N-(4-methoxyl group-6-methyl isophthalic acid, 3,5-triazine-2-yl)-N-methylamino) carbonyl) amino) sulfonyl) methyl benzoate

Second daxtron ((3,5, the 6-trichloro-2-pyridyl) oxygen) acetate

Tridiphane 2-(3, 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-(2,4-dichlorophenoxy) butyric acid

The red dipropyl thiocarbamic acid of weed eradication S-propyl diester

Xylachlor 2-chloro-N-(2, the 3-3,5-dimethylphenyl)-the 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 chemical compounds I a is to the detoxification ability with rice infringement due to the compound ii a processing

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 (Colby, S.R., Weeds, 15: 20-22,1967);

E＝A+B-A×B/100

The E=expected value

The experimental value of A=compound ii a

The experimental value of B=chemical compounds I a

For example:

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

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

E＝45%+2%-45%×2%/100

E＝46%

Table 2

Compounds, I c and I a+ I c are to using compound

The detoxification ability of rice infringement due to II a handles

Table 3

Chemical compounds I a is to the influence of compound ii a control barnyard grass activity

Table 4

Compound ii a is to the influence of chemical compounds I a control arrowhead activity

Claims

1, a kind of agricultural composition that is suitable for of controlling the growth of undesirable plant in the rice class crop, a kind of compound that is selected from formula II a-II c that said composition comprises herbicidally effective amount is selected from the sulfonyl urea compound of formula I a-I e with one or more, and they are suitable for agricultural salt:

2-chloro-N-(2-ethyl-6-aminomethyl phenyl)-N-(2-methoxyl group-1-Methylethyl) acetamide (metolachlor);

(Ⅱb)

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

(Ⅱc)

2-chloro-N-(ethoxyethyl group)-N-(2-ethyl-6-aminomethyl phenyl) acetamide (metolachlor);

(Ⅰa)

2-[[[[[(4,6-dimethoxy-2-pyrimidine radicals) amino] carbonyl] amino] sulfonyl] methyl] methyl benzoate (methylbenzene sulphur is grand);

(Ⅰb)

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);

(Ⅰc)

2-[[[[(4-methoxyl group-6-methyl isophthalic acid, 3,5-triazine-2-yl) amino] carbonyl] amino] sulfonyl] methyl benzoate (methyl first sulphur is grand);

(Id)

2-[[[[(4-chloro-6-methoxyl group-2-pyrimidine radicals) amino] carbonyl] amino] sulfonyl] ethyl benzoate (ethyl chloride wood is grand);

(Ie)

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 I a-I e in the herbicidal composition, then this sulfonylureas is not Id (ethyl chloride wood is grand);

B) if formula I compound is I e, then formula II compound is II c, i.e. metolachlor;

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

2, a kind of herbicidal composition of claim 1, its Chinese style II compound is II a, i.e. metolachlor.

3, a kind of herbicidal composition of claim 2, the sulfonyl urea compound of its Chinese style I are I e, i.e. N-(((4,6-dimethoxy-2-pyrimidine radicals) amino) carbonyl)-1-methyl-4-(2-methyl-2H-tetrazolium-5-yl)-1H-pyrazoles-5-sulfonamide.

4, a kind of herbicidal composition of claim 2, the sulfonyl urea compound of its Chinese style I are I c, and promptly methyl first sulphur is grand.

5, a kind of herbicidal composition of claim 2, the sulfonyl urea compound of its Chinese style I are formula I a, and promptly methylbenzene sulphur is grand.

6, a kind of herbicidal composition of claim 2, the sulfonyl urea compound of its Chinese style I are that formula I a is that methylbenzene sulphur swells and formula I c is that methyl first sulphur is grand.

7, a kind of herbicidal composition of claim 1, its Chinese style II a-II c compound is II c, sulfonyl urea compound is formula I a.

8, a kind of herbicidal composition of claim 7, wherein sulfonyl urea compound is formula I c.

9, a kind of herbicidal composition of claim 7, wherein sulfonyl urea compound is formula I a and I c.

10, a kind of method of controlling undesirable plant growth in the rice class crop, this method comprises, each composition in the claim 1-9 of rice class crop applying herbicidally effective amount.