JPS6325588B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention relates to novel N-(heterocyclic aminocarbonyl)-o-(pheenylbenzenesulfonamides) useful as agricultural chemicals, particularly as herbicides and growth regulators. 1966 September Dutch patent issued on May 15th
121788 teaches the preparation of compounds of formula () and their use as general or selective herbicides: [In the formula, R ₁ and R ₂ independently have 1 to 4 carbon atoms
and R ₃ and R ₄
can independently be hydrogen, chlorine or alkyl of 1 to 4 carbon atoms] Compounds of formula () and their use as antidiabetic agents are described in J. Drug. Roe. 6 , 123 (1974). ) is reported in: [In the formula, R is pyridyl. ] U.S. Patent No. 4,127,405 contains the general formula [In the formula, R ₁ is

【formula】

【formula】

[Formula] or

[Formula], R ³ and R ₆ are independently hydrogen, fluorine, chlorine, bromine,
Iodine, alkyl having 1 to 4 carbon atoms, 1 carbon number
-4 alkoxy, nitro, trifluoromethyl, cyano, _CH3S (O) _o- or _CH3CH2S ( _O ) _o-
, R ₄ is hydrogen, fluorine, chlorine, bromine, or methyl, R ₅ is hydrogen, fluorine, chlorine, bromine, methyl, or methoxy, and R ₇ is hydrogen, fluorine, chlorine, bromine, and has 1 carbon number. ~2
is alkyl or alkoxy having 1 to 2 carbon atoms, R ₈ is hydrogen, methyl, chlorine or bromine, R ₉ and R ₁₀ are independently hydrogen, methyl, chlorine or bromine, and W and Q are independently oxygen or sulfur, n is 0, 1 or 2, X is hydrogen, chlorine, bromine, methyl, ethyl, alkoxy having 1 to 3 carbon atoms, trifluoromethyl,
CH ₃ S- or CH ₃ OCH ₂ - and Z methyl or methoxy, with the proviso that (a) when R ₅ is other than hydrogen, R ₃ , R ₄ , R ₆
and at least one of R ₇ is other than hydrogen,
and at least two of R ₃ , R ₄ , R ₆ and R ₇ must be hydrogen (b) R ₅ is hydrogen and R ₃ , R ₄ , R ₆ and R ₇
When all of are other than hydrogen, R ₃ , R ₄ ,
All of R ₆ and R ₇ must be chlorine or methyl, and (c) when R ₃ and R ₇ are both hydrogen, R ₄ ,
at least one of R ₅ or R ₆ must be hydrogen] or agriculturally suitable salts thereof are disclosed. In particular, the patent discloses ortho-substituted compounds in which the substituents are _C1 - _C4 alkyl. The presence of undesirable plants causes substantial damage to useful crops, especially those that satisfy basic human food needs, such as soybeans, corn, wheat, and the like. Due to the recent population explosion and resulting global food shortages, improvements in the production efficiency of these crops are desired. One method of improving efficiency is to prevent or minimize the loss of such valuable crop parts by eliminating or inhibiting the growth of undesirable plants. A wide variety of substances are available that are used for the control or control of unwanted plant growth, and such substances are commonly referred to as herbicides. However, there is a need for more effective herbicides that control or retard the growth of weeds without causing significant damage to useful plants. The present invention relates to novel compounds of the formula, suitable agricultural compositions containing them, and methods of their use as general and selective herbicides. [In the formula, R is

[Formula], R ₁ is H, F, Cl or Br, R ₄ is H, F, Cl or Br, R ₅ is H, and A is

[Formula], X is CH ₃ , OCH ₃ or OCH ₂ CH ₃ , Y is CH ₃ , OCH ₃ or OCH ₂ CH ₃ , and Z is N or CH] Relatively high herbicide Preferred for reasons of activity and/or relative ease of synthesis are: 1 X is CH ₃ , OCH ₃ or OCH ₂ CH 3 and Y is _{CH 3 or} OCH ₃ 2 A compound of the formula 1, wherein R ₄ is H or Cl; 3 A compound of 2 above, wherein R ₁ is H or Cl. Particularly preferred for the highest herbicidal activity and/or the most favorable ease of synthesis are: 3,2'-dichloro-N-[(4-methoxy-6-
Methyl-1,3,5-triazin-2-yl)-
Aminocarbonyl][1,1'-biphenyl]-sulfonamide N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl][1,1'-biphenyl]-
2-Sulfonamide, N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl][1,1'-biphenyl]-
2-Sulfonamide, N-[(4-methoxy-6-methylpyrimidine-
2-yl)aminocarbonyl][1,1'-biphenyl]-2-sulfonamide, N-[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl][1,1 ′−
biphenyl]-2-sulfonamide, N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl][1,
1'-biphenyl]-2-sulfonamide, N-[(4-methoxy-6-methyl-1,3,5
-triazin-2-yl)aminocarbonyl]
[1,1'-biphenyl]-2-sulfonamide. Compounds of formula can be prepared by the following reaction sequence: Sulfonylisocyanates can be prepared, for example, by the method of Ulrich et al. [J.Org.Chem.34, 3200].
(1969)]. sulfonamide,
Boil under reflux with the reactants and excess thionyl chloride acting as solvent. The reaction is continued until no sulfonamide protons can be detected in the proton resonance spectrum. Generally, an overnight reaction time (approximately 16 hours) is sufficient. The thionyl chloride is evaporated and the residue is dissolved in an inert solvent (eg toluene, benzene, xylene, etc.) and contacted with a catalytic amount of pyridine and then with at least one equivalent of phosgene. Heat the mixture to about 60~140°,
Heat preferably to 80-100°. Conversion to isocyanate is substantially complete within about 1/4 to 3 hours.
The mixture containing the sulfonylisocyanate can be used directly for the next reaction step (formation of the sulfonylurea), or the sulfonylisocyanate can be isolated by filtration and evaporation of the solvent. The isocyanate is redissolved in a suitable solvent (such as methylene chloride, benzene, toluene, xylene or acetonitrile) and the solution is contacted with the aminoheterocycle _H2NA ,
Sulfonylurea products can also be provided. The reaction is generally exothermic. Conveniently, the starting reaction temperature is room temperature, but can vary from about 0 DEG to 100 DEG if desired. The product can be isolated by filtration if it precipitates from the reaction mixture, or by evaporation of the solvent and thereby obtaining a residual product, optionally in an organic solvent in which it is sparingly soluble. (e.g. diethyl ether, 1
-chlorobutane, etc.). Illustrative compounds with structural formulas are listed below:

【table】

【table】

【table】

【table】

【table】

【table】

【table】

【table】

【table】

[Table] Example 1 3,2'-dichloro-N-[(4-methoxy-6-
methyl-1,3,5-triazin-2-yl)
Aminocarbonyl][1,1-biphenyl]-2
-Sulfonamide a 3,2-dichloro-[1,1-biphenyl]-
2-Sulfonyl chloride 250 g of 2-chloroaniline was added dropwise to 588 ml of concentrated HCl and 196 ml of water at 0-10°.
Flush the mixture with nitrogen and 147 at 0-5°.
g of sodium nitrite in 294 ml of water for 1 hour. After 0.5 hours at 5-10° and 1.2 hours at 0-10°, the mixture was
ml of cold ₍ 5-10°) conc. and the mixture was stirred gently overnight. The heavy oil was removed, the aqueous layer was extracted with butyl chloride, and the combined organic parts were washed with water (twice),
Wash with half-saturated sodium bicarbonate solution (until the wash water is basic) and with saturated saline, then
Dry over _MgSO4 , treat with activated charcoal, and filter. The liquid was evaporated to a deep red oil and vacuum distilled to remove material boiling below 119° at 0.1 torr. The vessel residue was dissolved in butyl chloride, filtered through silica gel, and the liquid was evaporated to an oil that was distilled in vacuo.
The fraction boiling at 180-196°/(0.7-1.0 Torr) was chromatographed on a column of silica gel with butyl chloride/hexane (1:6-1:4 volume ratio) and after evaporation of the solvent the sulfonyl chloride in orange oil (Rf 0.58, butyl chloride/hexane, 1:6 on a silica gel-coated TLC plate).
(using a volume/volume eluent). Approximately 95% for gas chromatography/mass spectrometry
showed purity. The above isomer structure was confirmed by NMR. b 3,2'-dichloro-[1,1'-biphenyl]-
2-Sulfonamide A solution of 1.5 of the sulfonyl chloride (from a) in tetrahydrofuran (THF) with ammonia is then diluted with water, the aqueous layer is decanted, and the residual white solid is separated and washed with butyl chloride. did.
The solid was dissolved in hot ethyl acetate, the solution was dried (MgSO ₄ ), and diluted with hexane to give the desired sulfonamide, 1.33 g (90% yield), mp
151-153° was precipitated. c 3,2'-dichloro-[1,1'-biphenyl]-
2-Sulfonylisocyanate The sulfonamide (from b) was dissolved in 40ml of thionyl chloride and refluxed for 42 hours. Unreacted thionyl chloride was evaporated to yield N-sulfinyl sulfonamide as a yellow oil. This oil was mixed with 10 ml of a 13.8% phosgene solution in toluene and 1
A drop of pyridine was contacted and heated on a steam bath (under a dry ice condenser) for 1.7 hours. The mixture was evaporated and the residue was dissolved in acetonitrile and filtered. A sample of the acetonitrile solution was evaporated to a gum, treated with a small amount of methylene chloride, and the infrared spectrum of the gum thus diluted was examined. The presence of isocyanate was confirmed by a strong absorption peak at 2330 cm ^-1 . d 3,2'-dichloro-N-[(4-methoxy-6
-Methyl-1,3,5-triazin-2-yl)aminocarbonyl][1,1'-biphenyl]
-2-Sulfonamide A solution of the sulfonylisocyanate (from c) in acetonitrile was treated with 0.7 g of 2-amino-4-methoxy-6-methyl-S-triazine and the mixture was stirred at room temperature for 18 hours. The white solid was separated and the liquid was evaporated to a sticky solid. It was based on the title sulfonylurea. This product was ground with butyl chloride and dissolved in THF,
It was then further purified by precipitation from THF solution by dilution with 0.5NHCl. The solid was redissolved in THF. The butyl chloride solution obtained from the initial grinding is evaporated, the residue is dissolved in THF and precipitated by diluting the THF solution with 0.5NHCl, the precipitate is dried and boiled with butyl chloride. The mixture was then filtered and the liquid diluted with hexane to precipitate a white solid. Dissolve this solid in THF,
The solution was combined with the THF solution obtained earlier and evaporated. The residue was washed with butyl chloride and hexane to give the title sulfonylurea in the form of 1.17 g of a white solid, mp 141° (dec.). The IR spectrum showed an absorption at 1720 cm ¹ consistent with the urea carbonyl group. Example 2a 1,1'-biphenyl-2-sulfonylisocyanate Dry ice-cooled reflux condenser, stirrer, gas inlet tube and thermometer.
In a 500 ml three-necked round bottom flask, add 12 g of 1,1
-biphenyl-2-sulfonamide, 100 ml xylene, 0.2 g 1,4-diaza[2.2.2]bicyclooctane (DABCO) and 5 g n-butyl isocyanate. The mixture was heated to 135° and then phosgene was passed through the system until the temperature dropped to 125°. Continue heating and mixing to bring the mixture to 135°C, then add more phosgene and reduce the temperature to 120°C. This cycle was repeated until the temperature of the reflux mixture was maintained at 120° without further addition of phosgene. The mixture was then cooled to room temperature, filtered and concentrated in vacuo. Due to the extreme reactivity of sulfonylisocyanates, contact with moisture was carefully avoided. The product thus obtained (yield 10.4 g) showed an absorption peak at 2200 cm ^-1 in the infrared spectrum, which was consistent with sulfonylisocyanate. Example 2b N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl][1,1'-biphenyl]
-2-Sulfonamide To a suspension of 1.2 g of 2-amino-4,6-dimethylpyrimidine in 25 ml of acetonitrile was added 2.6 g of 1,1'-biphenyl-2-sulfonylisocyanate with stirring at room temperature. After stirring for 2 hours, the mixture was filtered and the liquid was concentrated in vacuo. The residue thus obtained, after being triturated with chlorobutane, melted at 78° with evolution of gas. It is δ2.2 (singlet, CH ₃ ) in the nuclear magnetic resonance spectrum (60MHz),
δ6.56 (singlet, pyrimidine CH) and δ6.8−7.9
(multiplet, phenyl hydrogen) in a ratio of 6:1:9, which was consistent with the desired structure. Preparations Useful preparations of compounds of formula may be prepared in conventional manner. They include powders, granules, tablets, suspensions, emulsions, wettable powders, concentrated emulsions, and the like. Many of these can be applied directly. The spray preparations can be bulked up in a suitable medium and used in spray volumes of a few liters to a few hundred liters/ha. High strength compositions are primarily used as intermediate products for subsequent formulations. Generally speaking, the preparation comprises about 0.1-99% by weight of active ingredient, and a) about 0.1-20% surfactant.
% and b) from about 1 to 99.9% of a solid or liquid diluent. More particularly the preparation will contain these ingredients in approximately the proportions indicated below:

Table of Contents Of course, lower or higher amounts of active ingredient than those shown in the table may be present depending on the intended use and physical properties of the compound. A high proportion of surface-active to active ingredients is particularly desirable and is achieved by incorporation into the formulation or by mixing in a tank. Typical solid diluents are described in “Handbook of Insecticide” by Watkins et al.
"Dust Diluents and Carriers", 2nd edition, Dorland Books, Caldwell, N.
J.), but other solids, natural and synthetic, may also be used. Adsorptive diluents are also suitable for wettable powders and powder concentrates. Typical liquid diluents and solvents are described by Marsden,
"Solvents guide", 2nd edition, Interstience, NY, 1950. Solubility below 0.1% is suitable for concentrated suspensions; concentrated solutions are preferably stable to phase separation at 0°C. “McCutcheon’s Detergents and
Emulsifiers Annual”, Allured Publ. Corp., NJ, and by Sisely and Wood.
“Encyclopedia of Surface Active Agents”
Chemical Publ.Co.Inc., N.
Y.), 1964, indicates surface activity and its recommended uses. All preparations may contain small amounts of additives to reduce foaming, caking, corrosion, microbial growth, etc. Methods for producing such compositions are well known.
Solutions are prepared by simply mixing the components. Finely divided solid compositions are produced by mixing and commonly grinding using a hammer mill or fluid energy mill. Suspensions are made by wet milling (see Littler, US Pat. No. 306,084). Granules and tablets may be produced by spraying the active substance onto preformed granular carriers or by agglomeration methods. References, by J.E. Browning,
“Agglomeration”, Chemical Engineering, 12
Monthly issue, 147 pages (1967), and Perry.
Author, Chemical Engineer's Handbook, 5th edition,
pp. 8-57, McGraw-Hill, Inc.
Hill, NY), 1963. For further literature on preparation techniques see, for example: HM Loux, US Pat. No. 3,235,361
No. 6, column 6, line 16 to column 7, line 19, and Examples 10 to 41. R.W. Luckenbaugh, U.S. Patent No. 3,309,192, column 5, line 43 to column 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138 to
140, 162-164, 166, 167, 169-182. H. Gysin and E. Knusli,
U.S. Pat. No. 2,891,855, column 3, line 66 to column 5, line 17 and Examples 1-4. By GC Klingman, (Weed
Control as a Science”, John Willy
John Wiley and Sons
Inc., NY), 1961, pp. 81-96. JD Fryer and SA Evans, “Weed Control Handbook” No. 5
Edition, Blackwell Scientific Publications
Publications, Oxford), 1968, pp. 101-103. In the following examples, all parts are by weight unless otherwise indicated. Example 3 Wettable powder 3,2'-dichloro-N-[(4-methoxy-6-
methyl-1,3,5-triazin-2-yl)
Aminocarbonyl][1,1'-biphenyl]-2
- Sulfonamide 80% Sodium alkylnaphthalene sulfonate 2% Sodium lignin sulfonate 2% Synthetic amorphous silica 3% Kaolinite 13% The above components were mixed and ground in a hammer mill to reduce the average particle size to 50 microns or less. . The material was remixed, passed through a No. 50 US standard sieve, and packaged. Example 4 Wettable powder N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl][1,1'-biphenyl]
-2-Sulfonamide 50% Sodium alkylnaphthalene sulfonate 2% Low viscosity methylcellulose 2% Diatomaceous earth 46% The above ingredients were mixed and coarsely ground in a hammer mill, then air milled to essentially reduce the actual diameter. All produced particles of 10 microns or less. The product was remixed and packaged. Example 5 Granules Wettable powder of Example 4 5% Attapulgite particles (US standard 20-40 mesh 0.84-0.42 mm) 95% Wettable powder slurry containing 75% solids was placed in a double cone mixer. Sprayed onto the surface of attapulgite particles. The particles were dried and packaged. Example 6 Extruded tablet N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl][1,1'-biphenyl]
-2-Sulfonamide 25% Anhydrous sodium sulfate 10% Crude calcium lignin sulfonate 5% Sodium alkylnaphthalene sulfonate 1% Calcium/magnesium bentonite 59% The above ingredients were mixed and processed in a hammer mill, then about 12% water I moistened it with This mixture was extruded into cylinders with a diameter of about 3 mm, which were cut into tablets with a length of 3 mm. It could be used directly after drying, or the dried tablets could be crushed and passed through a No. 20 US standard sieve (0.84 mm opening). It was packaged for use with particles that fit through a No. 40 US standard sieve (0.42 mm opening), and the area under the sieve was circulated. Example 7 Oily suspension 3,2'-dichloro-N-[(4-methoxy-6-
methyl-1,3,5-triazin-2-yl)
Aminocarbonyl][1,1'-biphenyl]-2
- Sulfonamide 25% Polyoxyethylene sorbitol hexaoleate 5% Higher aliphatic hydrocarbon oil 70% The above ingredients were ground together in a sand mill to reduce solid particles to less than about 5 microns. The resulting suspension was applied directly, preferably after being extended with oil or emulsified in water. Example 8 Wettable powder N-[(4-methoxy-6-methylpyrimidine-
2-yl)aminocarbonyl][1,1'-biphenyl]-2-sulfonamide 20% Sodium alkylnaphthalene sulfonate 4% Sodium ligninsulfonate 4% Low particle size methyl cellulose 3% Attapulgite 69% The above components were thoroughly mixed. After milling in a hammer mill to produce particles essentially all below 100 microns, the material was remixed, passed through a No. 50 US standard sieve (0.3 mm opening), and packaged. Example 9 Aqueous suspension N-[4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl][1,
1′-biphenyl]-2-sulfonamide 40.0% Polyacrylic oxidizing agent 0.3% Dodecylphenol polyethylene glycol ether 0.5% Disodium phosphate 1% Monosodium phosphate 0.5% Polyvinyl alcohol 1.0% Water 56.7% Mix the above ingredients, They were then milled together in a sand mill to produce particles essentially all below 5 microns in size. Example 10 Low strength granules N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl][1,
1'-Biphenyl]-2-sulfonamide 0.1% Attapulgite (US standard sieve 20-40 mesh) 99.9% The active ingredient is dissolved in the solvent and the solution is sprayed onto the dedusted particles in a double cone mixer. did. After spraying the solution was complete, the material was warmed to evaporate the solvent. The material was cooled and then packaged. Example 11 Granules 3,2'-dichloro-N-[(4-methoxy-6-
methyl-1,3,5-triazin-2-yl)
Aminocarbonyl][1,1'-biphenyl]-2
- Sulfonamide 80% Wetting agent 1% Crude lignin sulfonate (contains 5-20% natural sugar) 10% Attapulgite clay 9% The above ingredients are mixed and ground into a 100 mesh sieve. I passed it. This material was then added to a fluidized bed granulator, the air flow was adjusted to gently fluidize the material, and fine mist droplets of water were sprayed onto the material being fluidized. Fluidization and atomization continued until particles of the desired size range were produced. Even when spraying is stopped, the water content remains at the desired level, typically 1%.
Fluidization was continued, optionally with the addition of heat, until reduced to below. The material was then removed, sieved to the desired size range, generally 14-100 mesh (1410-149 microns), and packaged for use. Example 12 High thickener N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl][1,1'-biphenyl]
-2-Sulfonamide 99% Silica aerosol 0.5% Synthetic amorphous finely divided silica 0.5% The above ingredients were mixed and ground in a hammer mill so that essentially all of the
0.3 mm) was produced. This material was then used in various ways to produce preparations. Example 13 Wettable powder 3,2'-dichloro-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl][1,1'-biphenyl]-2 −
Sulfonamide 90% Dioctyl Sodium Sulfone Succinate 0.1% Synthetic Fine Silica 9.9% The above ingredients were mixed and ground in a hammer mill to produce particles essentially all below 100 microns. Pass the material through a No. 50 U.S. standard sieve;
Then it was packaged. Example 14 Wettable powder N-[(4-methoxy-6-methyl-1,3,5
-triazin-2-yl)aminocarbonyl]
[1,1'-biphenyl]-2-sulfonamide
40% Sodium Lignosulfonate 20% Montmorillonite Clay 40% The above ingredients were ground to produce particles essentially all below 10 microns. This material was remixed and then packaged. Example 15 Powder N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl][1,1'-biphenyl]
-2-Sulfonamide 10% Attapulgite 10% Pyrophyllite 80% The active ingredient was mixed with the attapulgite and then passed through a hammer mill to produce particles substantially all of which were less than 200 microns. The milled concentrate was then mixed with powdered pyrophyllite until homogeneous. Example 16 Solvent N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl][1,1'-biphenyl]
-2-Sulfonamide Sodium Salt 5% Water 95% The salt was added directly to water with stirring to make a solution, which was packaged for subsequent use. Uses The compounds of the invention are active herbicides. They are suitable for pre-emergence of weeds in areas where complete suppression of all vegetation is expected, such as around fuel storage tanks, around ammunition depots, industrial storage areas, oil well sites, amphitheaters, around public notice boards, highways and railway tracks. /Also has a wide range of utility for post-emergence control. By suitable selection of application rates and times of application, the compounds of the invention can be used to advantageously improve plant growth and selectively suppress weeds in crops such as rice and wheat. The rate of use of the compounds in the formula depends on many factors, including the specific end result desired, the coexisting crop species, the weed species to be controlled, the weather and climate, the formulation selected, the method of application, the amount of foliage present, etc. Determined by Generally speaking, the compound is about 0.01-20Kg/
ha, preferably in amounts of 0.1 to 10 Kg/ha. In this case, lower doses in the above range are used when applied to light soils and/or soils with low organic matter content, when selectively controlling weeds, or when only short-term persistence is required. Ru. Compounds of formula can also be combined with other weed agents, and are particularly useful in combination with: 3-(3,4-dichlorophenyl)-
1,1-dimethylurea (diuron); triazines, such as 2-chloro-4-(ethylamino)-6
-(isopropylamino)-s-triazine (atrazine); uracils, e.g. 5-bromo-3-
Secondary-6-methyluracil (bromacil); N-(phosphonomethyl)glycine (glyphosate); 3-cyclohexyl-1-methyl-6-
Dimethylamino-s-triazine-2,4 (1H,
3H)-dione (hexazinone); N,N-dimethyl-2,2-diphenylacetamide (diphenamide); 2,4-dichlorophenoxyacetic acid (2,
4-D) (and closely related compounds); 4-chloro-2
-Butynyl 3-chlorophenylcarbamate (Balban); S-(2,3-dichloroallyl)diisopropylthiocarbamate (Dialert); S-
(2,3,3-trichloroallyl) diisopropylthiocarbamate (trialate); 1,2-
Dimethyl-3,5-diphenyl-1H-pyrazolium methyl sulfate (diphenzocatomethyl sulfate); Methyl 2-[4-(2,4-dichlorophenoxy)-phenoxy]propanoate (dichlorohopmethyl) ;4-amino-6-tertiary-
Butyl-3-(methylthio)1,2,4-triazin-5(4H)one (metribuzin); 3-(3,
4-dichlorophenyl)-1-methoxy-1-methylurea (linuron); 3-isopropyl-1H-
2,1,3-benzothiodiazin-4(3H)-one-2,2-dioxide (pentazone); α, α,
α-Trifluoro-2,6-dinitro-N,N-
Dipropyl-p-toluidine (trifluralin); 1,1'-dimethyl-4,4-bipyridinium ion (paraquat); -sodium methane arsonate (MSMA); 2-chloro-2',6'-diethyl (methoxymethyl) Acetanilide (alachlor); 1,1-dimethyl-3-(α,α,α-
Trifluoro-m-tolyl)urea (fluorometuron); N-(butoxymethyl)-2-chloro-N
-(2,6-diethylphenyl)-acetamide (butachlor); 4-(2,4-dichloro-phenoxy)-2-methoxy-1-nitrobenzene (chloromethoxynyl) and S-[(4-chlorophenyl)methyl ] Diethyl carbamothioate (thiobencarb). The herbicide properties of this compound have been demonstrated in numerous greenhouse tests. The test method and results are as follows. Test A Digitaria sp., Echinochloa crusgalli, Avenafatua, Cassia tora, Ipomoea sp., Xanthium
sp.), sorghum, corn, soybean, rice,
Wheat seeds and tubers of common grass were planted in a growth medium and subjected to pre-emergence treatment using the compounds of Table 4 dissolved in a solvent that is non-toxic to the plants. At the same time, cotton with five leaves (including cotyledons), kidney bean with the third three leaflets spreading out, crabgrass with two leaves, goldenberry with two leaves, oat with two leaves, and three leaves with three leaves. Ebisugusa with leaves (including cotyledons), morning glory with four leaves (including cotyledons), Japanese sorghum with four leaves (including cotyledons), four-leaf sorghum, four-leaf corn, soybean with two cotyledons, trifoliate of rice, single-leaf wheat, and three to five-leaf trifolium were also sprayed with a solution of the listed compound in a non-phytotoxic solvent. Treated and control plants in a greenhouse
kept for 16 days and compared all seeds to controls,
Response to treatment was assessed visually. Using the following evaluation method: 0 = no effect 10 = maximum effect C = etiolation/destruction E = germination inhibition G = growth retardation H = effect of formation 6Y = abscessed flower or bud

【table】

Table: Test B Fallsington fertilized and limed in two plastic bulb pans.
Filled with silt loam soil. One pan was planted with corn, sorghum, Kentucky bluegrass, and various herbaceous plants. In the other pan, put the cotton,
Soybeans, Cyperus rotundus and various broad-leaved weeds were planted. The following herbaceous plants and broad-leaved weeds were planted. Digitaria (Digitaria)
sanguinalis), Isbie (Echinochloa)
crusgalli), oat (Avena fatua), sorghum halepense, dallis grass (Paspalum dilatatum), setaria faberii, bromus secalinus, mustard (Brassica)
arvensis), Ona fir (Xanthium
pennsylvanicum), Amaranthus
retrofexus), morning glory (Ipomoea hederacea),
Cassiatora, Sida spinosa, Abutilon
theophrasti), and Datura stramonium. Furthermore, 2 with a diameter of 12.5 cm
Rice and wheat were planted in two pots filled with prepared soil. The other 12.5cm pot was planted with sugar beets. The above four containers were pre-emergent treated with several test compounds falling within the scope of the invention. After 28 days of treatment, the response of the plants to the chemical treatment was visually evaluated using the evaluation system described above in Test A. This data is shown in Table B. Certain compounds may prove useful in pre-emergence treatment of weeds in crops.

【table】

[Table] Test C Soybean, cotton, alfa, maize, rice, wheat, sorghum, velvet leaf (Abutilon theophrasti), and sesbania in 25 cm diameter plastic pots filled with Fallsington manure. (Sesbania
exaltata) Cassia tora, Ipomoea sp., Datura
stramonium), Onamomi (Xanthium
pennsylvanicum), crabgrass (Digitaria sp.),
Cyperus rotundus, Echinochloa crusgalli, Setaria faberii, and Avena
fatua) was planted. Approximately 2-1/2 weeks after planting, the young plants and all of the soil around them were sprayed with test chemicals dissolved in a solvent that is non-toxic to the plants. Fourteen days after treatment, all species were visually evaluated for response to treatment compared to untreated controls. The rating system was as described above with respect to Table A. The data are shown in Table C. Several compounds tested by this method were useful for post-emergent weed control in crops.

【table】

[Table] Test D Falsington silt loam soil was placed in a plastic flower pot with a diameter of 10 cm, and Cyperus rotundus tubers were planted at a depth of approximately 2 cm. Five tubers were planted in each pot. The compounds of the invention were dissolved in a diluent that is non-toxic to plants and sprayed at a rate of 560 l/ha according to four application methods. That is, this preparation can be applied to the soil surface, tubers/soil, inside the soil,
and applied after germination. This soil surface spraying consists of spraying the present compound onto the surface of tightly covered soil, and the tuber/soil spraying consists of spraying the present compound onto the exposed tubers and soil in the veins of the leaves;
Then it was time to add untreated cover soil. In-soil treatment consisted of mixing the compound with the covering soil and then using it to coat the tubers. Post-emergence treatment consisted of spraying the preparation on the leaves and the surrounding soil surface of the leaf sedge when it germinated and grew to about 12 cm in height. Pots that received post-emergence treatment were placed directly in the greenhouse. Pots treated with other treatments were misted with approximately 0.3 m ³ of water before being transferred to the greenhouse. Response evaluations made after 4 weeks are recorded in Table D based on the same evaluation system as described in Study A.

【table】

Claims (1)

[Claims] 1. The following formula [wherein R is [formula], R ₁ is H, F, Cl or Br, R ₄ is H, F, Cl or Br, R ₅ is H, A is [formula] , X is CH ₃ , OCH ₃ or OCH ₂ CH ₃ , Y is CH ₃ , OCH ₃ or OCH ₂ CH ₃ , and Z is N or CH]. 2 3,2'-dichloro-N-[(4-methoxy-6
-methyl-1,3,5-triazin-2-yl)
The compound according to claim 1, which is aminocarbonyl][1,1'-biphenyl]-sulfonamide. 3 N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl][1,1'-biphenyl]-
Claim 1, which is 2-sulfonamide
Compounds described in Section. 4 N-[(4,6-dimethoxypyrimidine-2-
yl)aminocarbonyl][1,1'-biphenyl]
The compound according to claim 1, which is a -2-sulfonamide. 5 N-[(4-Methoxy-6-methylpyrimidin-2-yl)aminocarbonyl][1,1'-biphenyl]-2-sulfonamide. 6 N-[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl][1,
1′-biphenyl]-2-sulfonamide,
A compound according to claim 1. 7 N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl][1,
1′-biphenyl]-2-sulfonamide,
A compound according to claim 1. 8 N-[(4-methoxy-6-methyl-1,3,
5-triazin-2-yl)aminocarbonyl]
The compound according to claim 1, which is [1,1'-biphenyl]-2-sulfonamide. 9 The following formula [Wherein, R is [Formula], R ₁ is H, F, Cl or Br, R ₄ is H, F, Cl or Br, R ₅ is H, A is [Formula] , X is CH ₃ , OCH ₃ or OCH ₂ CH ₃ , Y is CH ₃ , OCH ₃ or OCH ₂ CH ₃ , and Z is N or CH]. An undesirable plant growth inhibitor characterized by comprising: 10 The compound is 3,2'-dichloro-N-[(4-
Methoxy-6-methyl 1,3,5-triazine-
The agent according to claim 9, which is 2-yl)-aminocarbonyl][1,1'-biphenyl]-sulfonamide. 11 The compound is N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl][1,1'-
The agent according to claim 9, which is biphenyl]-2-sulfonamide. 12 The compound is N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl[1,1'-
The agent according to claim 9, which is biphenyl]-2-sulfonamide. 13 The compound is N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]
The agent according to claim 9, which is [1,1'-biphenyl]-2-sulfonamide. 14 The compound is N-[(4,6-dimethyl-1,
The agent according to claim 9, which is 3,5-triazin-2-yl)aminocarbonyl][1,1'-biphenyl]-2-sulfonamide. 15 The compound is N-[(4,6-dimethoxy-
The agent according to claim 9, which is 1,3,5-triazin-2-yl)aminocarbonyl][1,1'-biphenyl]-2-sulfonamide. 16 Claims in which the compound is N-[(4-methoxy-6-methyl 1,3,5-triazin-2-yl)aminocarbonyl][1,1'-biphenyl]-2-sulfonamide The agent according to item 9.