PYRAZOLESULFONAMIDE DERIVATIVE, PROCESS FOR ITS PRODUCTION AND HERBICIDE CONTAINING IT

Abstract: A pyrazolesulfonamide derivative represented by Formula (I): wherein R represents a hydrogen atom or a methyl group; X represents a hydrogen atom or a fluorine atom. The compound is useful as a herbicide having not only excellent killing effect on weeds but also the selectivity on certain crops. Useful processes for synthesizing the compound are also disclosed.

Description: BACKGROUND OF THE INVENTION This invention relates to a novel pyrazolesulfonamide derivative, a process for preparing the compound and a herbicide containing the compounds as an active component. In order to protect important crops such as rice plants, wheat, cotton and sugar beets from damages by weeds to achieve an increased yield, it is indispensable to use a herbicide. In recent years in particular, a herbicide having selectivity (or discriminativity) is saught after as it can kill only weeds selectively (or discriminatively) without damages to crops by agricultural chemicals even when a foliage treatment is applied simultaneously on crops and weeds in a cultivated land wherein useful crops and weeds are grown together. Also, from viewpoints of the prevention of environmental pollution, the transportion, and the economical cost reduction in application of chemicals, studies and researches have been made over many years on such compounds that may achieve a higher herbicidal activity with use of chemicals in a lower amount. Some of the compounds having such a property are presently used as the herbicide having selectivity. Still, however, there are further demands for new compounds having such a property. As a prior technique, European Patent Publication No. 87,780 discloses a pyrazolesulfonylurea which may have the structure similar to the compound of this invention. However, there has been nothing disclosing the compound wherein a heterocyclic ring is substituted on a pyrazole ring as this invention discloses. SUMMARY OF THE INVENTION The present inventors have made researches over many years to develop herbicides having the selectivity on important crops, and have examined herbicidal properties of a number of compounds to create compounds haivng a higher herbicidal effect and the selectivity. As a result, it was found that a pyrazolesulfonamide derivative of Formula (I) shown below has a strong herbicidal effect to various weeds while retaining high safety to the important crops in either case of the soil treatment or the foliage treatment. According to the invention, there is provided a pyrazolesulfonamide derivative represented by Formula (I): wherein R represents a hydrogen atom or a methyl group; X represents a hydrogen atom or a fluorine atom. Subject matter of the present invention are therefore pyrazolesulfonamide derivatives of formula (I) according to claim 1. Preferred embodiments thereof are subject matter of claims 2, 3 and 4. Further subject matter of the present invention is a process according to claim 5 or 6 for preparing a pyrazole sulfonamide derivative of formula (I) according to the present invention. A further subject matter of the present invention is a herbicide according to claim 7 comprising as an active component one or more of a pyrazol sulfonamide derivative of formula (I). Preferred embodiments thereof are subject matter of claims 8, 9 and 10. A still further subject matter of the present invention is a method according to claim 11 of selectively protecting important crops while exerting a herbicidal effect on various weeds, which method is characterized by the application of an effective amount of one or more compounds of formula (I). Compounds of this invention have selectivity to wheat. The certain compounds of the compound of this invention, having the selectivity on wheat, are suited for selectively controlling wild oats. Wild oats are known to be improtant weeds growing with the culture of wheat. However, since wheat and wild oats belong to a plant species which is akin to each other, the known sulfonylurea type herbicides (the above-mentioned chlorsulfuron, for example) having the selectivity on wheat have also no effect to the wild oats, and thus it has been difficult to control them. The compound of this invention, on the other hand, shows a high herbicidal activity in a very low amount of the active component as compared with the conventional herbicides, and accordingly it is useful also as a herbicide for orchards and uncultivated lands. DESCRIPTION OF THE PREFERRED EMBODIMENTS The compound of this invention, represented by Formula (I) can be readily prepared by selecting either one of the procedures according to claim 5 or 6. Namely, a pyarazolesulfonyl isocyanate derivative (II) is dissolved in an inert solvent of suffciently dried dioxane, acetonitrile, etc., to which a pyrimidine, derivative shown by Formula (III) is added to carry out stirring, whereupon a compound of this invention is obtained by generally swift reaction. When the reaction proceeds with difficulty, a suitable base or bases such as triethylamine, triethylenediamine, pyridine, sodium alkoxide and sodium hydride may be added to allow the reaction to proceed readily. Or a pyrazolesulfonamide derivative (V) is reacted with chloro formate or carbonate in a solvent such as acetone, methyl ethyl ketone and acetonitrile and in the presence of a base or bases such as potassium carbonate to form a compound (IV), followed by heating together with a compound (III), to obtain a compound according to the invention. The starting pyrazolesulfonyl isocyanate (II) or pyrazolesulfonyl carbamate derivative (IV) used in the reactions can be synthesized by first synthesizing a pyrazolesulfonamide (V) by selecting a suitable process as mentioned below, and further making reference to the process disclosed in European Patent Publication No. 87,780 and Japanese Unexamined Patent Publication No. 13266/1980. This pyrazolesulfonamide which is an intermediate used in this ivention is also a novel compound, and may be obtained by selecting a suitable process from the processes shown in Reaction Schemes 1 to 4 below. Reaction Scheme 1 Reaction Scheme 2 Reaction Scheme 3 Reaction Scheme 4 In the above; (a): NaNO₂·HCl or NaNO₂·HBr (b): SO₂·Cu salt (c): NH₄OH or ammonium carbonate (d): Cu salt (e): POCl₃ or POBr₃ (f): P₂S₅ (g): NaSH (h): NaOH·NH₄OH·NaOCl (i): NaSCH₂Ph (j): Cl₂/CH₃COOH·H₂O (k): BuLi or LiN(i-Pr)₂, followed by Cl₂ or Br₂ (l): an oxidant (n): 1) BuLi or LiN(i-Pr)₂, 2) SO₂, 3) N-chlorosuccinimide (o): ClC(=S)NMe₂/base (p): heating In the above formulae, B, D and A, have the meaning and position as indicated in table 1 below. Usually, pyrazolesulfonamide (in) is obtained by reacting a corresponding pyrazolesulfonylchloride with ammonia water or ammonium carbonate. In order to introduce a sulfonyl group into pyrazole, the following methods may be used: (i) An amino group is subjected to diazonium decomposition in the presence of sulfur dioxide to obtain pyrazolesulfonylchloride. (ii) Hydroxypyrazole is formed into o-pyrazolethiocarbamate, and thereafter a sulfur atom is introduced into pyrazole ring by a rearrangement reaction, followed further by oxidation to obtain pyrazolesulfonylchloride. (iii) A sulfur atom is introduced into pyrazole by a nucleophilic substitution with a halogen atom, etc., followed further by oxidation, if necessary, to obtain pyrazolesulfonylchloride. (iv) Carbanion of pyrazole is formed by use of a base, on which sulfur dioxide is acted, followed by halogenation to obtain pyrazolesulfonylchloride. (v) Pyrazolesulfonylchloride is directly obtained by sulfuryl chloride. (vi) A pyrazole derivative obtained by any of the above methods is modified with other functional group by utilizing an attribute of pyrazole. More specifically; (i) Taking the procedures of Reaction Scheme 1, aminopyrazole is formed into a diazonium salt with use of sodium nitrite, etc. in hydrochloric acid or hydrobromic acid, and then sulfur dioxide is acted on it in the presence of a catalyst such as copper salt usually used for the diazonium decomposition, to obtain the corresponding pyrazolesulfonylchloride. By allowing ammonia water to act on it, the desired pyrazolesulfonamide (V) can be obtained. (ii) Taking the procedures of Reaction Scheme 4, hydroxypyrazole is used as a starting material to obtain o-pyrazolethiocarbamate, which is then heated for its transition to s-pyrazolethiolcarbamate, followed by oxidation with use of chlorine in a solvent such as acetic acid to obtain pyrazolesulfonylchloride. The desired pyrazolesulfonamide can also be obtained by allowing ammonia water to act on the pyrazolesulfonylchloride. Both of these Reaction Schemes 1 and 4 are not affected by the position of substituent. (iii) A nucleophilic substitution against pyrazole usually takes place most readily at the 5-position, and, in the next place, at 3-position it may sometimes takes place when an electron attractive group is substituted on the 4-position. Taking the procedures of Reaction Scheme 2 by utilizing this tendency, a sulfur atom is introduced into the 5-position by treating halogenated pyrazole with use of sodium hydrosulfide, sodium salt of benzylmercaptan, etc., followed by oxidation with use of chlorine in a solvent such as acetic acid to obtain pyrazolesulfonlchloride. Similar to Reaction Scheme 1, the desired pyrazolesulfonamide (V) can be obtained by allowing ammonia water to act on it. It is also possible to obtain the desired pyrazolesulfonamide (V) by forming an intermediate 5-mercaptopyrazole into sulfenamide, followed by oxidation thereof. The starting 5-position halogenated pyrazole can be obtained by diazo decomposition of aminopyrazole, a reaction of hydroxypyrazole with phosphorous oxychloride or phosphorous oxybromide, or by formation of a 5-position anion with use of a strong base such as butyl lithium and lithium diisopropylamide, followed by halogenation. (iv) When a substituent is at the 1-position, the hydrogen at the 5-position of a pyrazole ring generally has relatively strong acidity. Taking the procedures of Reaction Scheme 3, an anion can be formed with use of a strong base such as butyl lithium and lithium diisopropylamide, thereafter treating it with sulfur dioxide and N-halogenosuccinimide to form pyrazolesulfonylchloride, and then treating it with ammonia water to obtain the desired pyrazolesulfonamide (V). It is also possible by utilizing an attribute of pyrazole to obtain various types of pyrazolesulfonamide (V) by newly introducing a substituent into pyrazolesulfonamide, or by modifying a substituent having been introduced in it. Pyrazoles used as starting materials in the above reactions can be synthesized in most cases by making reference to A.N. Kost and I. I. Groundberg, Advan. Heterocyclic Chem., Vol. 6, p.347, 1966; T. L. Yacobs, Heterocyclic Compounds, R. C. Elderfield, Vol. 5, p.45, Wiley, New York, 1957; or K. Shofield, M. R. Grimmett and B. R. T. Keene, Heterocyclic Nitrogen Compounds The Azoles, Cambridge University Press, London, New York, Melbourne, 1976; Kevin T. Potts, Comprehensive Heterocyclic Chemistry, Vol. 5, p.167, Pergamon Press, 1984. When the group A is substituted on the 1-position of a pyrazole ring, it can be obtained by using A in place of hydrazine, methylhydrazine, phenylhydrazine, etc. in the above publications. Usually, it is possible for one skilled in the art to obtain an intermediate of the compound of this invention by studying experimental conditions on the basis of the descriptions hereinabove and the known arts in the above publications. In the following, synthesis examples for synthesizing the compound of this invention and the intermediate pyrazolesulfonamide will be described concretely as Exampels and Reference Examples, by which, however, by no means the invention is limited. Reference Example 1 Synthesis of 4-methoxycarbonyl-1-(2-pyridyl)pyrazole-5-sulfonamide (m.p. : 151 to 153°C), Synthesis was carried out according to Reaction Scheme 2 via the Methyl 5-chloro-1-(2-pyridyl)pyrazole-4-carboxylate, (m.p.: 86 to 88°C) and Methyl 5-mercapto-1-(2-pyridyl)pyrazole-4-carboxylate, (m.p.: 120 to 121°C). Reference Example 2 Synthesis of 4-methoxycarbonyl-3-methyl-1-(2-pyridyl)pyrazole-5-sulfonamide: Synthesis was carried out following Reference Example 1. m.p.: 196 to 198°C. Reference Example 3 Synthesis of 1-(6-fluoropyridin-2-yl)-4-methoxycarbonylpyrazole-5-sulfonamide: Synthesis was carried out following Reference Example 1 m.p.: 174 to 175°C. Each of the intermediates had the following property. Methyl 5-amino-1-(6-fluoropyridin-2-yl)pyrazole-4-carboxylate, m.p.: 143 to 145°C. Methyl 5-chloro-1-(6-fluoropyridin-2-yl)pyrazole-4-carboxylate, m.p.: 112 to 115°C. Methyl 1-(6-fluoropyridin-2-yl)-5-mercaptopyrazole-4-carboxylate, m.p.: 120 to 122°C. Reference Example 4 Synthesis of 4-methoxycarbonyl-3-methyl-1-(2-pyridyl)pyrazole-5-sulfonamide: (procedures other than Reference Example 2) Properties of intermediates: Methyl 5-amino-3-methyl-1-(2-pyridyl)pyrazole-4-carboxylate, m.p.: 115 to 116°C. Methyl 5-chloro-3-methyl-1-(2-pyridyl)pyrazole-4-carboxylate, m.p.: 111 to 112°C. Methyl 3-methyl-5-mercapto-1-(2-pyridyl)pyrazole-4-carboxylate, m.p.: 102 to 105°C. Synthesis of 4-methoxycarbonyl-3-methyl-1-(2-pyridyl)pyrazole-5-sulfonamide: In 200 ml of methylene chloride, 20.4 g of methyl 3-methyl-5-mercapto-1-(2-pyridyl)pyrazole-4-carboxylate was dissolved, and thereafter 200 ml of water was added. While maintaining the mixture at not higher than 5°C, 64 ml of conc. hydrochloric acid was added thereto, to which 250 ml of an aqueous solution of sodium hypochlorite (effective chlorine concentration: 6 %) was added dropwise at -5°C, followed by stirring at -5°C for 10 minutes. After separation of organic layer, extraction was carried out by adding 100 ml of methylene chloride to the aqueous layer. Organic layer was combined with the previous organic layer, followed by washing with an aqueous solution of sodium bisulfite, and then 40 ml of 28 % ammonia water was added at 10°C or lower. After stirring at room temperature for 10 minutes, solvent was evaporated. Crystals precipitated were filtered, washed with water, further washed with ether and dried to obtain 18.3 g of the title compound. m.p.: 196 to 198°C. Reference Example 5 Synthesis of 1-(6-fluoropyridin-2-yl)-4-methoxycarbonyl-pyrazole-5-sulfonamide: Synthesis was carried out following Reference Examples 1 m.p.: 174 to 175°C. Each of the intermediates had the following property. Methyl 5-amino-1-(6-fluoropyridin-2-yl)pyrazole-4-carboxylate, m.p.: 143 to 145°C. Methyl 5-chloro-1-(6-fluoropyridin-2-yl)pyrazole-4-carboxylate, m.p.: 112 to 115°C. Methyl 1-(6-fluoropyridin-2-yl)-5-mercaptopyrazole-4-carboxylate, m.p.: 120 to 122°C. Example 1 Synthesis of N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl)-4-methoxycarbonyl-1-(2-pyridyl)pyrazole-5-sulfonamide (Compound (1) ): 1,9 g of 4-methoxycarbonyl-1-(2-pyridyl)pyrazole-5-sulfonamide, 0.82 g of methyl chloroformate and 1.4 g of anhydrous potassium carbonate were heated under reflux in 50 ml of anhydrous acetonitrile for 4 hours. After the reaction was completed, solvent was evaporated under reduced pressure. After dilution with ice water, insolubles were filtered off, and the filtrate was precipitated with use of diluted hydrochloric acid. Crystals precipitated were filtered, washed with water and dried to obtain N-[4-methoxycarbonyl-1-(2-pyridyl)pyrazole-5-sulfonyl]methylcarbamate. 0.91 g of N-[4-methoxycarbonyl-1-(2-pyridyl)pyrazole-5-sulfonyl]methylcarbamate and 0.33 g of 2-amino-4,6-dimethylpyrimidine were heated under reflux in 30 ml of toluene for 6 hours while allowing the toluene to evaporate little by little. Toluene having been decreased was occasionally supplemented. After the reaction was completed, toluene was evaporated under reduced pressure. Isopropyl ether was added to the residue, which was then stirred to obtain the title compound as crystals. m.p.: 159 to 160°C. Following the procedure described in Example 1 above the compounds 132 (m.p: 129 to 132°C), 5454 (m.p.: 156 to 159°C) and 5485 ( ) indicated in Table I below, have been prepared. In the above, Q₁ and Q₇₉ each represent the following heterocyclic group. In application of the compounds of this invention as herbicides, they can be applied by mixing with suitable carriers such as solid carriers, including for example clay, talc, bentonite, diatomaceous earth and others or liquid carriers, including for example water, alcohols (methanol, ethanol and the like), aromatic hydrocarbons (benzene, toluene, xylene and the like), chlorinated hydrocarbons, ethers, ketones, esters (ethyl acetate, etc.), acid amides (dimethylformamide, etc.) and others. They can be provided for practical use with addition of any desired additive selected from an emulsifier, a dispersing agent, a suspending agent, a wetting agent, a spreader and a stablizer and in any desired form such as a soluble concentrate, an emulsifiable concentrate, a wettable powder, a dust, a granule, a suspension concentrate, etc. In the following, there are shown examples of formulations of herbicides containing the compounds of this invention as active ingredients, but they are not limitative of this invention. In the exemplary formulations shown below, "parts" mean "parts by weight". Exemplary Formulation 1 : Wettable powder Compound No. 1 of this invention 10 parts Ziegleit PFP (kaolin type clay; trade name; produced by Ziegleit Kogyo Co., Ltd.) 83 parts Solpol 5039 (mixture of nonionic surfactant and anionic surfactant; trade name; produced by Toho Kagaku Co., Ltd.) 5 parts Carplex (anticaking agent) (white carbon; trade name; produced by Shionogi Seiyaku Co., Ltd.) 2 parts The above components are mixed and pulverized homogeneously to prepare a wettable powder. Exemplary Formulation 2 : Wettable powder Compound No. 132 of this invention 20 parts Ziegleit PFP (kaolin type clay; trade name; produced by Ziegleit Kogyo Co., Ltd.) 73 parts Solpol 5039 (mixture of nonionic surfactant and anionic surfactant; trade name; produced by Toho Kagaku Co., Ltd.) 5 parts Carplex (anticaking agent) (white carbon; trade name; produced by Shionogi Seiyaku Co., Ltd.) 2 parts The above components are mixed and pulverized homogeneously to prepare a wettable powder. If desired, the compound of this invention may be applied as a mixture with other kinds of herbicides, various insecticides, sterilizers or adjuvants during preparation or spraying In particular, when applied in beet fields, useful ones include phenmedipham, desmedipham, lenacil, pyrazone., ethofumesate and so on. As the other kinds of herbicides mentioned above, there may be included those as described in Farm Chemicals Handbook, 70th Edition (1984). The compounds of this invention can also be applied, in addition to the agricultural and horticultural fields such as farm fields, paddy fields, fruit gardens and the like, to athletic grounds, vacant lands, belts along railroads and others. The amounts of the pesticide to be applied, which may differ depending on the scenes to be applied, the time of application, the application method, the kinds of the objective grasses and the crops harvested, may generally range suitably from about 0.25 to about 10 kg per hectare. When applied to beets in particular, it may range suitably from 0.25 to 500 g/ha, preferably from 0.5 to 250 g/ha. The following test examples are set forth for illustration of the utility of the compounds of this invention as herbicides. Test Example 1 : Herbicidal effect test by soil treatment In a plastic box of 15 cm length, 22 cm width and 6 cm depth, there was placed a sterilized deluvium soil, and seeds of (A) rice ( Oryza sativa ), (B) barnyardgrass ( Echinochloa crusgalli ), (C) large crabgrass ( Digitaria adscendens ), (D) annual sedge ( Cyperus microiria ), (E) black nightshade ( Solanum nigrum L.), (F) hairly galinosoga ( Galinosoga ciliata ), (G) rorippa ssp. ( Rorippa atrovirens ), (H) corn ( Zea mays ), (I) wheat ( Triticum vulgare ), (J) soybean ( Glysine max ), (K) cotton ( Gossypium ) and (L) sugar beet ( Beta vulgaris ) were sown mixedly. After covering soil to about 1.5 cm over the seeds, herbicides were sprayed evenly on the soil surface to predetermined proportions of the active ingredient. In spraying, the wettable powder as shown in the foregoing exemplary formulations was diluted with water and sprayed over the entire surface by means of a small sprayer. Four weeks after spraying, the herbicidal effect on crops including rice, etc. and the various weeds were examined according to the judgement criteria shown below. The results are shown in Table 2. Some of the compounds of this invention show the selectivity on certain crops. The above growth control rates are determined by measuring the top fresh weights of the treated plants and those of the non-treated plants, and calculated from the following formula: Test Example 2 : Herbicidal effect test by stem-leaf treatment In a plastic box of 15 cm length, 22 cm width and 6 cm depth, there was placed a sterilized deluvium soil, seeds of (A) rice ( Oryza sativa ), (B) barnyardgrass ( Echinochloa crusgalli ), (C) large crabgrass ( Digitaria adscendens ), (D) annual sedge ( Cyperus microiria ), (E) black nightshade ( Solanum nigrum L.), (F) hairly galinosoga ( Galinosoga ciliata ), (G) rorippa spp. ( Rorippa atrovirens ), (H) corn ( Zea mays ), (I) wheat ( Triticum vulgare ), (J) soybean ( Glysine max ), (K) cotton ( Gossypium ) and (L) sugar beet ( Beta vulgaris ) were sown in shapes of spots, respectively, followed by covering of soil to about 1.5 cm over the seeds. After respective plants have grown to the second and the third leaf stage, herbicides were sprayed evenly onto the stem-leaf portion at predetermined proportions of the active ingredient. In spraying, the wettable powder as shown in the foregoing exemplary formulations was diluted with water and sprayed over the entire surface of the stem-leaf portions of various weeds by means of a small sprayer. Four weeks after spraying, the herbicidal effect on crops including rice, etc. and the various weeds were examined according to the judgement criteria as shown in Test example 1. The results are shown in Table 3. Test Example 3 : Agricultural chemical damage test on wheat In a plastic box of 15 cm length, 22 cm width and 6 cm depth, there was placed a sterilized deluvium soil, and seeds of (I) wheat ( Triticum vulgare ) and (P) wild oat ( Avena fatua ) were sown in shapes of spots, respectively, followed by covering of soil to about 1.5 cm over the seeds. After respective plants had grown to the third and the fourth leaf stage, herbicides were sprayed evenly onto the stem-leaf portion at predetermined proportions of the active ingredient. On 20 days after treatment, the herbicidal effects on weeds and agricultural chemical damages on wheat were examined. The results are shown in Table 4. Comp. No. Amount of active ingredient applied kg/ha (I) (P) 1 0.01 0 4 0.02 0 5 0.04 0 5 1 3 2 0.01 0 4 0.02 0 5 0.04 0 5

Claims: A pyrazolesulfonamide derivative represented by formula (I): wherein R represents a hydrogen atom or a methyl group; X represents a hydrogen atom or a fluorine atom. A compound of claim 1, which is N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-4-methoxycarbonyl-1-(2-pyridyl)pyrazole-5-sulfonamide. A compound of claim 1, which is N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-4-methoxycarbonyl-3-methyl-1-(2-pyridyl)pyrazole-5-sulfonamide. A compound of claim 1, which is N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-4-methoxycarbonyl-1-(6-fluoropyridin-2-yl)pyrazole-5-sulfonamide. A process for preparing a pyrazolesulfonamide derivative represented by formula (I) according to claim 1: wherein R represents a hydrogen atom or a methyl group; X represents a hydrogen atom or a fluorine atom, which comprises allowing a pyrazolesulfonyl-isocyanate derivative represented by the formula (II) wherein R and X have the meaning given in claim 1, to react with the derivative represented by the following formula (III) in an inert solvent. A process for preparing a pyrazolesulfonamide derivative represented by the formula (I) according to claim 1: wherein R represents a hydrogen atom or a methyl group; X represents a hydrogen atom or a fluorine atom, which comprises allowing a pyrazolesulfonyl carbamate derivative represented by the formula (IV): wherein X has the meaning as given in claim 1, and R¹ represents a C₁-C₈ alkyl group or a phenyl group, to react with the derivative represented by the formula (III) in an inert solvent. A herbicide comprising as an active component one or more of a pyrazolesulfonamide derivative represented by formula (I) wherein R represents a hydrogen atom or a methyl group; X represents a hydrogen atom or a fluorine atom, and an agriculturally acceptable carrier. A herbicide of claim 7, wherein one of the active components is N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-4-methoxycarbonyl-1-(2-pyridyl)pyrazole-5-sulfonamide. A herbicide of claim 7, wherein one of the active components is N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-4-methoxycarbonyl-3-methyl-1-(2-pyridyl)pyrazole-5-sulfonamide. A herbicide of claim 7, wherein one of the active components is N-[(4,6-dimethylpyrimidin-2-yl)amino-carbonyl]-4-methoxycarbonyl-1-(6-fluoropyridin-2-yl)pyrazole-5-sulfonamide. A method for controlling the growth of undesired vegetation which comprises applying to the locus of such vegetation an agriculturally effective amount of one or more compounds of claim 1.

Inventors: IKAI,TAKASHI, KAKUTA, TAKUYA, MORIMOTO, KATSUSHI, NAWAMAKI, TSUTOMU, OYA, EIICHI, SATO, TOSHIAKI, YAMAMOTO, SUSUMU
Applicants: NISSAN CHEMICAL INDUSTRIES LTD.
Application year: 1986
Main classification: C07D401
IPC codes: A01N47, C07D521