PYRIDINE SULFONYL UREA DERIVATIVES

Abstract: The present invention relates to novel pyridine sulfonyl urea derivatives, having a herbicidal activity, which is described in structure of general formula (I), wherein P is P-1, P-2, P-3 or P-4; E is single bond or CH2; R<2> is C1-C6 alkyl substituted with 1 SIMILAR 3 halogen; R<3> is H or CH3; W is O or S; R1 and A are defined in the claims, and these may be an agriculturally suitable salt.

Description: PYRIDINE SULFONYL UREA DERIVATIVES TECHNICAL FIELD 5 The present invention relates to novel pyridine sulfonyl urea derivatives having agriculturally suitable for herbicidal activity. BACKGROUND OF THE INVENTION ι o It is publicly well known that sulfonyl urea derivatives have a herbicidal activity. Here are the formulas for the sulfonyl ureas. 1) U. S. Patent No. 4,332,611 discloses the compound having the following formula wherein, O O I! II L is OH, O-C-NH-R 12 or O-C-OR 13 ; 0 R is H, F, Cl, Br, N0 2 , CF 3 or Q-C, alkyl or alkoxy ; R 1 is H or C,-C 4 alkyl ; R 2 is H or CH 3 ; R 8 is H, CH 3 or OCH 3 ; A is pyrimidine or triazine. 5 2) U.S. Patent No. 4,786,314 discloses the compound having the following formula wherein, 5 R'is F, Cl, Br, C r C 4 alkyl, OH, alkoxy, alkylthioor C j - alkyl substituted with phenyl group ; R 2 is -CHR-CN etc. 3) U.S. Patent No.4,838,926 discloses the compound having the following i o formula wherein, Qis C Γ C 4 alkyl substituted with R 2 ; 5 R 2 is OR 3 , R 3 is H, C r C 4 alkyl ; Lis R 12 is H or CH, 4) European Patent No. 125,205 discloses the compound having the following formula wherein, R 6 is H, alkyl or F ; R 7 is H or CH 3 ; W is O or S ; R 8 is haloalkyl or alkoxyalkyl. 5) U. S. Patent No. 4,348,220 discloses the compound having the following formula wherein, L is OR 9 ; R 1 is H or C,-C 4 alkyl ; R 2 is H or CH 3 ; R 9 is C r C 6 alkyl. 6) U. S. Patent No. 4,822,403 discloses the compound having the following formula wherein, n is 0 or 1 ; W is G j -C j alkenyl substituted with 1 ~ 3 F, Cl, Br, OH or alkoxy. i o 7) U.S. Patent No. 4,662,933discloses the compound having the following formula wherein, 5 Q is linear -(CH.^- substituted with -Q haloalkyl ; n is an integer of 1 ~ 3 ; R 2 is SH, N 3 or SCN. 8) European Patent No. 13,480 discloses the compound having the following C formula wherein, R 1 is H, Cl, Br, F, alkyl, alkoxy, alkylthio or C0 2 R 5 . 9) U. S. Patents No. 4,435,206 and No. 4,522,645 disclose 2-pyridine sulfonyl urea substituted with R 1 on 3-position, wherein Rl is H, Cl, Br, F, alkyl, alkoxy, alkylthio, C0 2 R 5 or S0 2 NR 6 R 7 . 10) U. S. Patent No.4,339,267 discloses 3-pyridine sulfonyl urea compound having the following formula wherein, R 4 is H, Cl, Br, F, alkyl, alkoxy, N0 2 , C0 2 R 6 or SR 13 . 11) European Patent No. 30,433 disclose the compound having the following formula wherein, R 3 is H, Cl, Br, F, C0 2 R n or SOnR 12 . 12) U.S. Patent No. 4,456,469 discloses the compound having the following formula wherein, R is alkyl, alkenyl, CF 3 CHF 2 or CH 2 CF 3 ; Z is H, F, Cl, Br or SCH 3 . 1 C 13) U. S. Patent No. 4,487,626 discloses 2,3- or 4-substituted pyridine sulfonyl urea compound having the following formula wherein, A is R 2 is H, Cl, Br, F, alkyl, alkoxy, C0 2 R 5 , SOmR 6 , S0 2 NR 18 R 19 or C SO j NCOCH^CH, . 14) U. S. Patents No. 4,421,550 and No. 4,496,392, and European Patents No. 125,846/155,767/161,905/164,269/171,286 disclose pyridine sulfonyl urea substituted with Cl, Br, S0 2 R or SO- j NR'R 2 on 2- or 3-position. 15) U.S. Patent No. 4,549,898 discloses pyridine sulfonyl urea compound having the following formula wherein, ι o W II R 2 is H, alkyl, haloalkyl, halogen, N0 2 , alkoxy, -C-R 8 , S0 2 NR 6 R 7 or SOnR ; R 3 is H, halogen, alkyl, OCH 3 , N0 2 or CF 3 ; R 5 is H, N0 2 , F, Cl, Br, CH 3 , CF 3 , SOn alkyl, -C0 2 R or alkoxy. 15 16) U.S. Patent No. 4,579,583 discloses pyridine sulfonyl urea compound having the following formula 0 wherein, X is O, S, SO or S0 2 ; A is a optionally substituted alkyl, alkenyl or alkynyl ; R 1 is H, halogen, alkyl, alkoxy, haloalkyl, alkylthio or alkylsulfonyl. 17) U.S. Patent No.4,518,776 discloses a method for preparing the compound having the following formula wherein, R 1 is alkylsulfonyl or dialkylamino sulfonyl group ; R 2 is H, halogen, No 2 , CF 3 , alkyl or alkoxy. 1G 18) European Patent No. 101,670 discloses manufacture of pyridine sulfonyl urea having the following formula 15 wherein, R 1 is Q alkyl or S0 2 N R 4 R 5 ; Q is S or SOn ; R 2 is H, halogen, CF 3 , N0 2 , alkyl or alkoxy. z _ 19) U.S. Patent No. 4,521,597 discloses manufacture of pyridine sulfonyl urea compound having the following formula 5 wherein, 5 R 3 is H, F, Cl, Br, N0 2 , OCH 3 or CF 3 ; R 5 is SOm alkyl or S0 2 NR 8 R 9 ; R 6 is H, F, CH 3 or OCH 3 . 20) European Patent No. 184,385 discloses the compound having the following ι o formula 21 ) U.S. Patent No. 4,747,870 discloses O-alkylcarbonyl pyridine sulfonyl urea 5 compound, and U. S. Patent No.4,838,926 discloses O-substituted alkylpyridine urea compound. And, U.S.Patent No. 4,747,337 discloses the compound having the following formula 0 wherein, J is R 1 is H, alkyl, haloalkyl, halogen, N0 2 , alkoxy, alkylthio or CN ; R 2 - R 6 are alkylthio, alkylsulfinyl, alkylsulfonyl, cycloalkylthio, S0 2 R 8 , S0 3 R 8 N 3 , CN, CHP, CHF 2 , CH , haloalkyl or PO(0 alkyl) 2 . As the above patents, many sulfonyl urea herbicides have known until recently. Even with these herbicides, more and more weeds develop immunity forwards these herbicides and cause undesirable vegetations. Thus, continuous research is in demand to develop more effective and newer for a good harvest. Therefore, the object of the presentation is to invent a new pyridine sulfonyl urea derivative having a very prominent herbicidal activity with a good selectivity for various vegetations and agriculturally suitable herbicides for treatment of pre- emergence and/or post-emergence or plant growth regulants. SUMMARY OF THE INVENTION The present invention relates to novel pyridine sulfonyl urea derivatives having the following formula (I) o w II II P-S-NH-C-N-A ( I ) O R wherein, P is P-l, P-2, P-3 or P-4 as follows ; E is single bond or CH 2 ; R 1 is H, Cj- alkyl, C,-C 3 haloalkyl, halogen, CN, N0 2 , - alkoxy, C r C 3 haloalkoxy, S0 2 NR r R π , Cj-C, alkylthio, C,-C, alkylsulfinyl, C,- C 3 alkylsulfonyl, SCH^, NH 2 , NHCH 3 , N(CH 3 ) 2 , - alkyl substituted with C j - alkoxy, C j - haloalkoxy, SH, SCH 3 , CN or OH or C0 2 R ; and then R 1 is H, C r C 4 alkyl, C^ cyanoalkyl, methoxy or ethoxy ; R π is H, C j - alkyl, C 3 -C 4 alkenyl, or when taken together, connecting R 1 and R 11 , -(CH 2 ) 3 -, -(CH 2 ) 4 -, -(CH 2 ) 5 - or CHjCH-OCHjO , may be formed ; R ID is C,-C 4 alkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl, C j -C 4 alkyl substituted with 1 ~ 2 halogen orcyano groups, C 5 -C 6 cycloalkyl, C^ cycloalkylalkyl or C 2 -C 4 alkoxyalkyl ; R 2 is C alkyl substituted with 1 - 3 halogen ; R 3 is H or CH 3 ; W is O or S ; A is Al, A2, A3, A4, A5, A6 or A7 as following ; A 4 A l A 2 A 3 A 5 A 6 A 7 wherein, X is H, -C 4 alkyl, C r C 4 alkoxy, C r C 4 haloalkoxy, C r C 4 haloalkyl, C r C 4 haloalkyl thio, C j -C 4 alkylthio, halogene, C^ alkoxyalkyl, Cj- alkoxyalkoxy, amino, C j -C j alkylamino, diCC j - alkyl) amino or C 3 -Cs cycloalkyl ; Y is H, C,-C 4 alkyl, C r C 4 alkoxy, C r C 4 haloalkoxy, C C 4 haloakylthio, C r C 4 alkylthio, C j - alkoxyalkyl, C 2 -C 5 alkoxyalkoxy, amino, - alkylamino, di(C j -C j alkyl)amino, C 3 -C 4 alkenytoxy, C 2 -C 5 alkylfliioalkyl, C^ C 4 haloalkyl, C 2 -C 4 alkynyl, azido, cyano, C 2 -C 5 alkylsulfinylalkyl, C 2 -C 5 alkylsulfonylalkyl, CH j OH, - cycloalkyl, ^-C; cycloalkoxy, C,-C 4 O II alkynyloxy, -C-R 6 , CH 3 I or -N-OCH 3 ; m is 2 or 3 ; L 1 and L 2 are independently O or S ; R 4 and R 5 are independently C alkyl ; R 6 is H, or CH 3 ; X 1 is CH 3 , OCH 3 , OC 2 H 5 or OCHF 2 ; Y 3 is H or CH 3 ; Y 2 is CH 3 , CH 2 CH 3 , OCH 3 , OCftCft, SCH 3 or SCINCH, ; X 2 is CH 3 , CftCft, or CH 2 CF 3 ; X 3 is CH 3 or OCH 3 ; Y 4 is CH 3 , OCH 3 , OCft, CftOCft or Cl ; X 4 is CH 3 , OCH 3 , OOft, CftOCft or Cl ; and these may be an agriculturally suitable salt, and then, (1) if X is Cl, Br, F or I, Z is CH and Y is OCft, OCft, NCH 3 (OCH 3 ), Nft, NHCH 3 , N(CH 3 ) 2 or OCHF 2 ; (2) if X or Y is OCHF 2 , Z is CH ; (3) X 4 and Y 4 are not Cl simultaneously ; (4) if W is S, R 3 is H, A is A„ Z is CH or N and , Y is CH 3 , OCH 3 , OCftCft, CH 2 OCH 3 , Cft, CF 3 , SCft, OC,ftCΗ=Cft, OCftC≡CH, OCftCftOCft, CH(OCH 3 ) 2 or (5) if a number of total carbon atoms X and Y are more than 4, a number of carbon atoms of R 2 is 4 or less than 4. DETAILED DESCRIPTION OF THE INVENTION Among the definitions according to the present invention, the following 5 terms have the following meanings ; a) " Alkyl" used ether alone or in compound word such as "alkylthio" or "haloalkyl" etc. denotes straight chain or branched alkyls such as methyl, ethyl, n-propyl, isopropyl or buthyl isomers. b) "Alkoxy" denotes methoxy, ethoxy, n-propoxy, isopropoxy or buthoxy ι c isomers. c) "Alkenyl" denotes straight chain or branched alkenes, for example, vinyl, 1- prophenyl, 2-prophenyl, or buthenyl, pentenyl, hexenyl or heptenyl isomers etc. d) "Alkynyl" denotes straight chain or branched alkynyl such as ethynyl, 1- 5 propynyl, 2-propynyl, or buthynyl, pentynyl or hexynyl isomers. e) "Halogen" used ether alone or in compound ward "halo" denotes chlorine, fluorine, bromine or Iodine. A preferred group of pyridine sulfonyl urea derivatives having the formula shown as the below (I), in view of compounding of the polymer and herbicidal C activity, wherein (1) R 3 is H, W or O ; (2) R 1 is H, F, Cl, C r O alkyl, 0-Ohaloalkyl, C r O alkoxy, -0 haloalkoxy, 0- alkylthio, CftOCft or CftSCft ; (3) X is Cft, OCft, OCftCft, Cl, F, Br, OCHF 2 , CftF, OCH 2 CftF, OCftCHF 2 , OCftCF 3 , CF 3 , CftCl or CftBr ; Y is H, - alkyl, OCft, OCftCft, CftOCft, NHCft, NCft(OCft), N(CH 3 ) 2 , CF 3 , SCft, OCH 2 CH=CH 2 , OCftC≡CH, CftOOft, OCftCftOCft, CftSCft, OCHF j , SCHF-, cyclαpropyl, C≡CH, or C≡ C-CH 3 ; (4) R 2 is CftF, CHF 2 , CHFCl, CftCl, CH 2 Br, CHFCH 3 , CftCftF, CftCftC CHC1CH 3 , CHC1 2 , CHFCftF, CHC1CH 2 C1, CHFCftCl or CftCF 3 ; (5) A is A,, and Z is CH ; X is CftOCft, OCftCft, Cl or OCHF 2 ; Y is Cft, Oft. OCft, CftOCft, CH(OCH 3 ) 2 , OCHF 2 , NHCft, N(Me) 2 o cyclopropyl, and R 1 is H, Cft, OCft or Cl . The novel compounds having the above formula(I) according to the presen invention have a very strong herbicidal activity and a good selectivity for a useful vegetation. The compounds of the present invention can be prepared by reactions as described in herein below. The compound of general formula(I) can be obtained by hydrolyzing the compound of following formula (II) with alkali under water, organic solvent or the mixture solution thereof. ( Method 1 ) ( π ) ( I ) wherein, is or and R ] is not para substituent of sulfonyl urea. In the above reaction scheme of Method 1, Ac is acetyl group, but it may be a protecting group easily dissolved by acid, alkali or others. In order to hydrolyze the above Ac group, alkali base such as NaOH, KOH, LiOH, Na 2 C0 3 , K 2 C0 3 , etc., 5 preferably LiOH, may be used. The above reaction of Method I is carried out under water or organic solvent, and also a mixture of water with unreacting solvent such as methanol, ethanol, acetone or THF etc., or solvent alone. The hydrolysis in the reaction occurs at the temperature of 0 ~ 80 . and the i c reaction time of 1 ~ 24 hours, and then the obtained product may be easily seperated by acidifying with HC1 water solution. As an other process, after acidifying, the obtained product is extracted with methylene chloride, ethyl acetate, etc. then concentrated crystalized to obtain the final product. If necessary, a pure product can be obtained by purification to 15 column chromatograph. The compound of the above formula(I) according to the present invention can be prepared by reaction the compound having the following formula(III) with alkali at the temperature of 25 ~ 40t_ . (Method 2) (III ) The reaction of Method 2 may be preferably carried out under alkali such as NaOH etc. of a small quantity. The product may be seperated as the same with the above Method I. On the other hand, the compound of the above fσrmula(II) used in the present invention can be prepared by reacting the compound of following formula(IV) with formula(V). ( IV ) ( V ) The above reaction may be carried out in solvent of dioxane or acetoni ryl under in active atmosphere at the temperature of 251_ for 1 ~ 2 hours. The i o obtained product may be easily seperated by acidifying with HC1 water solution. As another process, after acidifying, the obtained product is extracted with solvent of methylene chloride or ethylacetate and dried/evaporated to obtain final product. Also, the compound of the above formula(III) used in the present invention 15 can be obtained by the method disclosed on U.S. Patent No. 4,370,480. Meanwhile, phenylcarbamate(V) used for preparing the above formula(II) can be composed by reacting heterocyclic amine of A-NHR 3 of formula(VI) with diphenylcarbonate or phenyl chloroform ate under a base such as NaH, pyridine, K 2 C0 3 , etc. after adding of dimethyl aminopyridine(DMAP), and then the reacting 0 mixture is stirred in a solvent such as THF etc. at 25 ~ 65 . for 12 ~ 36 hours. ιι O PhO-C-Cl + PhO-dJ-N-A - R i I 3 ( VI ) ( V ) The compound of the formula(IV) can be prepared by treating N-t- buthylsulfonamide(IV) with an acid such as trifluoroacetic acid(TFA), polyphosphoric acid(PPA) or p-toluensulfonic acid(p-TS A). ( VII ) In order to prepare the above formula(IV), the compound of the above formuIa(VII) is added in trifluoroacetic acid(about 0.3M) of an excess. And they are stirred at about 2513 for 1 ~ 72 hours to easily carry out the reaction. Then, a volatile metter is evaporated under vacuum and the residue is ciystalized in a solvent such as diethylether, 1 -chlorobutane, ethylacetate, etc. to isolate the product, sulfonamide of formula(_V). This reaction shall be referenced by J.D. Catt and W. L. Matier, J. Org. Chem., 38, 1974(1973). Also, sulfonamide of the above formula(IV) can be prepared by the following reaction process. As the above reaction, the compound of formuIa(_V) can be obtained by adding ammonia of a great quantity in sulfonylchloride, preferably temperature below -lO .:, and as a solvent such as ethylacetate, ether, THF, methylene chloride etc. may be used. On the other hand, the compound of the above formula(VII) can be prepared by the following reaction process. ( IXa) (4) Ac O/Py (Vπa) (wherein, L is H, OOft, NMe 2 or N(OCft)CH 3 ) In the above reaction, n-butyl lithium of 2 equivalents is added in the compound of the above formula(IXa) in order to lithiation ; and thereafter aldehide, ester or amide taking ketone compound, or N,0-dimethyl hydroxyamide is added ; if aldehide is used, hydroxy compound is produced directly ; and then the compound of formula(VIIa) can be prepared by acylation under pyridine ; if the compound of R 2 CHO is not obtained, after obtaining ketone compound then hydroxy compound be obtained by reduction of that with NaBft ; and then the compound of formula(VIIa) is easily obtaind by acylation. This reaction process is able to be carried out by a skill person in this technical field. Also, in the case of 2-pyridine sulfonamide, the compound of formula(VIIa) can be obtained by the same with the above reaction process. ( IXb) (Vllb) (3) NaBH /MeOH (4) Ac O Py Also, sulfonamide can be obtained by reacting su_fonylchloride(V_π) with t- BuNft as the following reaction scheme. (Vffl ) (IX) In the above reaction, sulfonylchloride can be prepared by the method of U.S.Patent No. 4,456,469 or 4,740,233 as following scheme. 5 ( XI ) (V ) Wherein, the reaction may be preferably carried out at low temperature of 10 . and below it. The compound of formula(XII) can be prepared by the following reaction G scheme. R-0 -CH JI R _Q avκvi (3) Cl 2 /HOAc (XIII) ^^ This reaction is disclosed in U.S. Patent No.4,420,325. The compound of formula(XI) can be prepared by the following reaction process. ( XV ) 3. NaBft In the reaction process, metalation reaction using LDA of 2-fluoropyridine may be carried out by the method of T, Gungor, F. Marsais and G. Gueguiner, J. Organomet Chem., 1981, 215, 139-150, and thereafter acylation by a common method. Halopyridin of the above formula(XV) is transformed to sulfide of formula(XIV) by rearing with a mercaptane under a base. This reaction is disclosed by U.S. Patent No. 4,456,469. Lithiation of fluoropyridine or transform reaction to sulfonyl chloride which is consisted of transformation to sulfide from fluoropyridin and its chloridization, can be easily carried out by the method of U.S.Patent No. 4,774,337. The compound of formula(XVI) can be composed by the following reaction process. It was well-known the reaction which is transformed aminopyridine to sulfonamide as preferably reference of U.S.Patent No.4,456,459. Also, exchange 5 reaction to metal halogen from bromosulfonamide was well-known, and thereafter sulfonamide (XVI) may be prepared by the above reaction scheme for manufacturing the above formula(VIIa). The heterocyclic amine compound of formula(VI) may be prepared by a skill person in this technical field from a method disclosed in literatures or the C simple transformation of it. For example, European Patent Application No. 84,244 (Pub. July 27, 1983) and J. Am. Chem. Soα, 69,3072(1947) of W. Braker et al. disclose a method for preparing aminopyrimidine and triazine substituted with acetyl group. European Patent No.72,347 and U. S. Patent No.4,443, 243/4, 487, 915 disclose a method for preparing aminopyrimidine and/or triazine substituted with haloalkyl such as OCHF 2 , SCHF 2 , OCftCftF and OCftCF 3 etc. and haloalkylthio as a substitution group. European Patent No. 108,708, U.S.Patent No. 4,515,626/4,600,428 disclose cyclo propylpyrimidine and/or triazine substituted with alkyl, haloalkyl, alkoxy, haloalkoxy, alkylamino, dialkylamio and alkoxyalkyl group etc. European Patent No. 15,863 discloses a method for preparing the compound of the above formula(VI), as 5,6-dihydro-puro[2,3-d] pyrmidine-2-amine 5 compounds and cyclopenta[d]pyrimidine-2-amine compounds which A is A 2 ; and 6,7-dihydro-5H-pyrano-[2,3-d] pyrimidine-2-amine compound which A is A 3 . European Patent No. 46,677 discloses puro[2,3-d]pyridine-2-amine compounds which A is A 4 in the formula(VI), and European Patent No. 73,562 discloses heterocyclic compounds which A is A 5 . i c The compound of formula(VI) which A is A 6 can be prepared by European Patent No. 94,260. The compound of formula(VI) which A is A 7 , can be manufactured by the method of European Patent No. 125,864. Common methods for preparing aminopyridine and triazine compounds is arranged on the following literatures : 15 " The chemistry and Heterocyclic compounds", Series, Interscience Publishers, Inc., New York and London ; " Pyrimidines" , Vol. 16, D.J. Brown Ed. ; "S-Triazines and Derivatives", Vol. 13, E.M. Smolin and L. Rapaport. Composition of triazine compounds is disclosed in F.C. Schaefer, U.S.Patent No. 3,154,547 and K.R. Huffman and F.C. Schaefer, J. Org. Chem., 28, 1812(1963). . " c On the other hand, salts of the compound of the above formula(I) also is useful as herbicide, and they can be prepared by various methods according to prior art. For example, metal salts of the compound can be prepared by reacting the above formula(I) compound with strong basic anion, e.g. alkali or alkaline earth r * . metal solution having hydroxyl group alkoxyde or carbonate, and also quaternary amine salt alike. A salt of the formula(I) compound may also be obtained by cation exchange. The cation exchange can be manfacturcd by directly reacting solution containing cation for exchange with solution of salt of formula(I), for example aqueous solution of alkali metal or quaternary amine salt. This method is useful when the desirable salt is water soluble, especially sodium, potassium or calcium salt. 5 The above manufacturing methods is summarized briefly, but the method can be carried out easily by a skill person in this technical field of composition and manufacturing for sulfonyl urea or organic composition. The compounds of said general formula(I) of the present invention specify the following Table ; 5 Table 1. Table 2. 39 Table 3. Table 4. Table 5. Table 6. Table 7. 58 Table 8. Table 9. Table 10. Table 11. Table 12. Table 13. Table 14. 65 Table 15. Table 16. Table 17. 68 Table 18. Table 19. Table 20. Table 21. Table 25. Table 26. Table 27. Table 28. Test results indicate that the compounds of the present invention are highly active pre-emergent or post-emergent herbicides or plant growth regulants. Many of them have utility for broad-spectrum pre- and or post-emergency weed control in areas where complete control of all vegetation is desired, such as around fuel storage tanks, ammunition depots, industrial storage areas, parking lots, drive-in theaters, around billboards, highway and railroad structures. Some of the compounds have utility for selective weed control in crops such as wheat and barley. Alternatively, the subject compounds are useful to modify plant growth. The rates of application for the compounds of the present invention are determined by a number of factors, including their use as plant growth modifiers or as herbicides, the crop species involved, the types of weeds to be controlled, weather and climate, formulations selected, mode of application, amount of foliage present, etc. In general terms, the subject compounds should be applied at levels of around 0.05 to 10 kg ha, the lower rates being suggested for use on lighter soils and/ or those having a low organic matter content, for plant growth modifications or for situations where only short-term persistence is required. Formulations Useful formulations of the compounds of formula(I) can be prepared in conventional ways. They include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates and the like. Many of these may be applied directly. Sprayable formulations can be extented in suitable media and used at spray volumes of from a few liters to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation. The formulations, broadly, contain about 0.1% to 99% by weight of active ingredient(s) and at least one of (1) about 0.1% to 20% surfactant(s) and (2) about 1% to 99.9% solid or liquid inert diluent(s). More specially, they will contain these ingredients in the following approximate proportions : * Active ingredient plus at least one of a surfactant or a Diluent equals 100 weight percent. Lower or higher levels of active ingredient can, of course, be present depending on the intended use and the physical properties of the compound. Higher ratios of surfactants to activate ingredient are sometimes desirable, and are achieved by incorporation into the formation or by tank mixing. Typical solid diluents are described in Watkins, et al., "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Doriand Books, Caldwell, N.J., but other solids, either mined or monufactured, may be used. The more absorptive diluents are preferred for wettable powders and the denser ones for dusts. Typical liquid diluents and solvents are described in Marsden, "Solvent Guide", 2nd Ed., Interscience, New York, 1950. Solubility under 0.1% is preferred for suspension concentrates ; Solution concentrates are preferably stable against phase separation at Ot. . "McCutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp., Ridgewood, N.J., as well as Sisely and Wood, "Encyclopedia of Surface Active Agents", Chemical Publishing Co., Inc., New 5 York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foaming, caking, corrosion, microbiological growth, etc. The methods of making such compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by ι o blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see, for example, Littler, U.S. Patent No. 3,060,084). Granules and pellets may be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See J.E. Browning, "Agglomeration", Chemical Engineering, Dec.4, 1967, 5 pp, 147ff. and "Perry's chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York, 1973, pp. 8-57ff. For further information regarding the art of formulation, see for example : H.M. Loux, U.S.Patent. No. 335,361, Feb. 15,1966, Col. 6, line 16 through Col. 7, line 19 and Examples 10 through 41 ; R.W. Luckenbaugh, 0 U.S.Patent. No. 3,309,192, Mar. 14, 1967, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162- 164, 166, 167 and 169-182 ; H. Gysin and E. Knusli, U.S.Patent No. 2,891,855, June 23, 1959, Col. 3, line 66 through Col. 5, line 17 and Examples 1 - 4 ; G.C.Klingman, "Weed Control as a Science", John Wiley and S.A. Evans, "Weed control Handbook", 5th Ed., 5 Blackwell Scientific Publications, Oxford, 1968, pp. 101-103. The compounds of the present invention can be used independently and may be used in combination with any other commercial herbicide. A summary of the possible combination herbicides is given below. propham pyrazon quizalofop sethoxydim SL-49 tebuthiuron terbuthylazine thiameturon methyl triclopyr trimeturon vernolat 15 EXAMPLE 1 : 2-Huoro-3-fluoroacetyl pyridine To a stirring solution of 1.5M lithium diisopropylamide mono (tetra¬ hydrofuran) (69ml) in 50ml anhydrous tetrahydrofuran cooled to -70 * 0 under nitrogen atmosphere is added dropwise 2-fluoropyridine(10g). To the solution is added dropwise ethyl fIuoroacetate(13g) in 5ml of _r. anhydrous tetrahydrofuran at -70 T_. and stirred for 3 hours at -70 _ . The reaction mixture is then poured into 200ml of cold water and neutralized with dilute H 2 S0 4 The mixture is extracted three times with methylene chloride. The methylene chloride portions are combined, dried over magnesium sulfate, filtered and evaporation of the methylene chloride, a residue is 5 obtained. This is chromatographed through silica gel using 1 : 3 ethyl acetate- hexane as eluant. Evaporation of the solvent mixture yields 12g of the desived product(Yield : 74%). ΗNMR (CDCI,): δ 5.1(1H, d), 5.8QH, d), 7.4 (1H, m), 8.4(2H, m). EXAMPLE 2 : 2-Huoro-3-(l-hydroxy-2-fluoroethyl) pyridine To 12g of 2-fluoro-3-(fluoroacetyl)pyridine dissolved in 30ml of methanol is added dropwise 1.44g of sodium borohydride. After stirring at 012 for 30 5 minutes to the solution is added 40ml of water. The resulting solution is extracted three times with methylene chloride and the methylene chloride phase is dried over magnesium sulfate, filtered and evaporated to obtain 12g of the desired product(colorless oil, Yield : 98%). ι o EXAMPLE 3 : 2-(Phenylmethylthio)-3-(l-hydroxy-2-fluoroethyl) pyridine To a stirring solution of a 60% dispersion of sodium hydride in mineral oil(3.9g) in 200ml anhydrous dim ethylform amide cooled to -512 under nitrogen atmosphere is added 11.6ml of benzyl mercaptan by using a syringe at a temperature of <0t_ . 5 After stirring at room temperature for one hour a solution of 2-fluoro-3-(l- hydroxy-2-fluoroethyl)pyrine(12g) in Ami of anhydrous dimethylformamide is slowly injected at 512. The resulting mixture is warmed slowly to room temperature and stirred for 24 hous. Water(200n_0 is then added and the mixture is extracted three times with 0 Et 2 0. The organic phase is washed with cold water and dried with magnesium sulfate. The solvent is removed under reduced pressure, and the residue is chromatographed on silica gel(n-hexane/EtoAc = 5 : 1 ) to afford the desired product(16g, oil). 5 * H NMR(CDC1 3 ) :S 3.4 (lH,m), 3.9-4.3(lH,m), 4.6(2H,s), 4.7-5. l(lH,m), 5.2-5.6(lH,m), 7.0-7.6 (6H.m), 7.9 (lH,m), 8.6 (lH,m). EXAMPLE 4 : 2-(Phenylmethylthio)-3-(l-acetoxy-2-fluoroe_hyl) pyridine A solution of 2-(phenylmethylthio)-3-(l-hydroxy-2-fluoroethyl)pyridine (16g) in dry THF and acetic anhydride(7.4g) is stirred with a catality amount of 4- dimethylaminopyridine at room temperature for 12 hours. The reaction mixture is then poured into water and neutralized with dilute H 2 S0 4 . The mixture is 5 extracted three times with methylene chloride, the combined extracts are dried(MgS04), evaporated to obtain the desired product(oil, 17.2g, Yield : 93%). Η NMR(CDC1 3 ): 2.2(3H, S), 4.2(1H, d), 4.5(2H, s), 5.0QH, d), 6.1,6.4(1H, t), 7.0~7.8(7H, m), 8.4(1H, m). \ EXAMPLE 5 : 3-(l-Acetoxy-2-fluoroethyl)-2-pyridinesulfonamide To a stirred solution of 2-(phenylmethylthio)-3-(l-acetoxy-2-fluoro-ethyl)- 2-pyridine(21g) in 350ml of methylene chloride and 350ml of water is added at 012 10.5zs_ ofconc. HCl. To the reaction mixutre 175ml of 10% sodium hypochlorite solution is 5 added for 30 minutes keeping the temperature below 112. The mixture is stirred at 012 for 20 minutes, poured into 80m/ of cold water and extracted three times with cold methylene chloride. The organic phase is separated, washed with sodium bisulfite and dried wish magnesium sulfate keeping the temperature below 0 . The dried solution is cooled in a dry ice-acetone C bath(-70 ) and then a slow stream of ammonia gas is passed for 10 minutes. The mixture is evaporated until the volume of the solution reaches lOOroZ. To the concentrated solution 50ml of water is add and the mixture is extracted three times with methylene chloride. The combined organic layer is dried with magnesium sulfate. The solvent is removed under reduced pressure and the residue is chromatographed on silica gel to afford the product(12g, Yield : 67%). m. P. : 127-129 12 Η NMR(DMSO-d 6 ) :£ 2.2(3H, s), 4.3(1H, t), 5.2QH, t), 6.7-7.1(1H, m), 7.2(2H, s), 7.7(1H, m), 8.0(1H, m), 8.6(1H, m). EXAMPLE 6 : N-[(4,6-Dimethoxy pyrimidin-2-yl)aminocarbonyl]-3-(l -acetoxy -2-fluoroethyl)-2-pyridinesulfonamide To 4.1 g of 3-(l-acetoxy-2-fluoroethyl)-2-pyridinesulfonamide in 50ml of 5 acetonitrile is added 4.22g of phenyl(4,6-dimethoxypyrimidin-2-yl)carbamate and 2.4g of l,8-diazabicyclo[5.4.0]undec-7-ene (DBU). After stirring at room temperature for 2 hours the solution is acidified to pH 4.5 with 5% hydrochloric acid. The resultant solution is extracted with methylene chloride and the methylene chloride phase is dried over magnesium sulfate, filtered and evaporated. i c Trituration of the residue with Et 2 0 yields 6g of the product(solid, Yield : 89%), which is washed with a mixture solvent of ethylacetate/n-hexane(l/l). m. p. : 145-147 2 -H NMR (CDC1 3 ) :S 2.2(3H, s), 4.0(6H, s) 4.5 (1H, m), 5.3(1H, m), 5.8(1H, s), 6.8-7.2(lH, m), 7.6(1H, m),8.3(lH, m), 8.7 (1H, m), 5 13.0(1H, Is). EXAMPLE 7 : N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-3-(l-hydroxy -2-fluoroethyl)-2-pyridinesulfonamide To 4g of N[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3-(l-acetoxy-2- C fluoroethyl)-2-pyridinesulfonamide in 100ml of methanol is added 0.46g of lithium hydroxide monohydrate and lml of water. After stirring at room temperature for 3 hours the solution is acidified to pH 4.5 with 5% hydrochloric acid. The resultant solution is extracted three times with methylene chloride. The organic phase is washed three times with water, 5 dried over magnesium sulfate, filtered and evaporated to yield 3.3g of the subject compound(Yield : 90%). m. p. : 1 19-120 12. Η NMR(Acetone-d 6 ) :S 3.97 (6H, s), 4.38-4.91(2H. m), 5.36(1H, s) 5.91(1H, s), 6.03 (1H, m) 7.74(1H, m), 8.43(lH,d), 8.57(lH,m), 9.55(lH,s), 13.02(1H, s) EXAMPLE 8 : 2-(l-Acetoxy-2-fluoroethyl)-3-pyridinesuIfonamide 5 5.3g of N-t-butyl 2-(l-acetoxy-2-fluoroethyl)-3-pyridinesulfonamide is added to 20ml of trifluoroacetic acid and allowed to stir at room temperature for 12hours. The acid is evaporated and the residual oil is taken up in CftCly This solution is washed with sat. aq. NaHC0 3 , evaporated and the crude solid product is crystallized from ethyl acetate and n-haxane ; 3.1g (Yield : 71%). 1 C m.p. : 141-14312 ΗNMR(CDCl 3 + DMSO-d 6 ) : δ 2.13(s, 3H), 4.83(m, 2H), 6.63-7.06(m, 1H), 7.20(S, 2H), 7.42-7.63(m, 1H), 8.32-8.86(m, 2H), IR(KBr) 1717 cm- 1 (C = 0) 5 EXAMPLE 9 : N-[(4,6-Dimethoxy-pyrimidin-2-yl)am_nocarbonyl]-2- (l-acetoxy-2-fluoroethyl)-3-pyridinesulfonamide To a solution of 2-(l-acetoxy-2-fluoroethyl)-3-pyridines_dfon__τι_de(2.10g) and phenyl(4,6-dimethoxypyιimidin-2-yl)carbamate(1.49g) in 50ml acetonitrile is C added dropwise 0.7 ml of l,8-diazabicycIo[5.4.0]undec-7-ene(DBU) at 1512. After stirring for 2 hours the resultant solution is extracted with methylene chloride and 5% hydrochloric acid. The orgaic phase is dried over magnesium sulfate, filtered and evaporated to yield the subject compound. m.p. : 188-19012 ■ HNMR(CDCI 3 ) : δ 2.03(s, 3H), 4.00(s, 6H), 4.84(dd, x = 460, J 2 = 6.0Hz, 2H), 5.84(s, 1H), 6.50-6.90(m, 1H), 7.33-7.68(m, 2H), 8.60-8.93(m, 2H), 13.33(s, 1H) IR(KBr) : 1737, 1702 cm "1 ( C = O ) EXAMPLE 10 : N-[(4,6-Dimethoxy-pyrimidin-2-yl)aminocarbonyl]-2- ( 1 -hydroxy-2-fluoroethyl)-3-pyridinesulfonamide To 0.88g of N-[(4,6-ctimemox * ypyrimidin-2-yl)aminoca__)onyl]-2-l-acetoxy- 5 2-fluoroethyl)-3-pyridinesulfonamide in 20ml of methanol is added 0.25g of lithium hydroxide monohydrate. The mixture is heated to reflux for 1 hour, then allowed to cool and the methanol is evaporated. The residue is taken up in 15ml of CH 2 C1 2 and lOnzZ of water, and acidified to pH 2-3 with IN HClaq. The organic phase is dried over magnesium sulfate, l o filtered and evaporated to yield 0.42g of the subject compound, m. p. : 162-16412 * HNMR(CDC1 3 + DMSO-d 6 ) : δ 4.02(s, 6H), 4.78(dd, J, = 4.6, J 2 = 5.0Hz, 2H), 5.88(s, 1H), 7.53-7.73(m, 1H), 5 8.53-8.98 (m, 2H) IR(KBr) : 1704 cm '1 ( C = 0 ) EXAMPLE 11 : N-( 1 , 1 -Dimethylethyl)-3-(chloroacetyl)-2-pyridinesulfonamide Under a nitrogen atmosphere, to a stirred solution of N-(l,l-dimethylethyl 2-pyridinesulfonamide(4.0g, 18.7 mmole) in 50τnl of anhydrous THF is slowly injected at -7012 17ml of 2.5M n-BuLi. The mixture is stirred for 3 hours at -4012 , cooled to -7012 and then 3g of ethyl chloroacetate is injected dropwise. The reaction mixture is stirred at -4012 for 1 hour, poured into cold water ~~ . and extracted three times with CH 2 C1 2 . The organic phase is dried over magnesium sulfate, filtered and evaporated. The residue is purified by chromatography to give the pure product(3.68g, Yield : 68%). NMR(CDC1 3 ) : δ 1.2(9H, s), 4.67(2H, s), 5.3(1H, s), 7.8(2H, m), 9.0(1H, m) EXAMPLE 12 : N-(l,l-Dimethylethyl)-3-(l-hydroxy-2-chloroethyl)-2- pyrimidinesulfonamide To a stirred solution of N-(l,l-dimethylethyl)-3-(chloroacetyl)-2-pyridine- 5 sulfonamide(3.68g, 12.7mmole) in 100_z_ of methanol is added at 012 NaBH 4 (0.24g, 6.35 mmole). The reaction mixture is stirred at 012 for 1 hour, added 10 ml of water and extracted three times with CH 2 C1 2 . The orgainic phase is dried over magnesium sulfate, filtened and evaporated to yield 3.56g of the subject compound (Yield : 96%). ιc EXAMPLE 13 : N-(l,l-Dimethylethyl)-3-(l-acetoxy-2-chIoroethyl)-2- pyrimidinesulfonamide To a stirred solution of N-(l,l-dimethylethyI)-3-(l-hydroxy-2-chloroethyl> 2-pyridinesulfonamide in dry THF is added 1.6g of Ac z O and a catality amount of 4-dimethyIaminopyridine. The mixture is stirred at room temperature for 12 hours, water is added, neutralized with dilute H 2 S0 4 and extracted three times with CH 2 C1 2 . The organic phase is evaporated to give the subject compound(3.6g, Yield : 88%). NMR(CDCI 3 ) : δ 1.2(9H, s), 2.2(3H, s), 4.0(2H, m), 5.7(1H, s), 7.0(1H, ), _r _ 7.7(1H, m), 8.1(1H, m), 8.7(1H, m). EXAMPLE 14 : 3-(l-Acetoxy-2-chloroethyl)-2-pyridinesulfonamide 3.6g of N-(l,2-dimethylethyl)-3-(l-acetoxy-2-chloroethyl)-2-pyridine- sulfonamide is added to 20ml of trifluoroacetic acid and alowed to stir at 4012 for 5 12 hours. The acid is evaporated and the crude product is purified by column chromatography to give the subject compound(3g). m. p. : 146-147 12 NMR(CDC1 3 ) : δ 2.1(3H, s), 4.0(2H, m), 6.0(2H, s), 6.9(1H, m), 7.7(lH, m), 8.1(1H, m), 8.7(1H, m) EXAMPLE 15 : N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-3- ( 1 -acetoxy-2-chloroethyl)-2-pyridinesulfonamide To a stirred solution of 3-(l-acetoxy-2-chloroethyl)-2-pyridinesulfonamide 5 (200mg) and phenyl(4,6-dimethoxypyrimidin-2-yl)carbamate(197mg) in 20ml of acetonitrile is added dropwise 109mg of DBU. After stirring at room temperature for 2 hours the solution is acidified to pH 4.5 with 5% aq. HC1. The resultant solution is extracted three times with methylene chloride and the methylene chloride phase is dried over MgS0 4 , filtered i o and evaporated. Trituration of the residue with Et^lOraZ ) yield 280mg of the solid product, m. p. : 159-161 12 EXAMPLE 16 : N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-3- 5 (1 -hydroxy-2-chloroethyl)-2-pyridine sulfonamide To 140mg of N[(4,6-dimethoxypyrimidin-2-yl)aminoca_bonyl]-2-(l-acetoxy -2-chloroethyl 2-pyridinesulfonamide in 20ml of methanal is added 20mg of LiOH • H 2 0 and 0.5 ml of water. After stirring at room temperature for 3 hours the solution is acidified to pH 4.5 with 5% aq. HC1. The resultant solution is 0 extracted three times with CH 2 C1 2 . The organic phase is evaporated and the trituration of the residue with E^O yields the solid product, m. p. : 135-137 12 5 In the following example, all parts are by weight unless otherwise indicated. EXAMPLE 17 Wettable Powder 3-( 1 -hydroxy)-2-fIuoroethyl)-N-[(4,6-dimethoxy pyrimidin-2-yl) amino carbonyl]-2-pyridinesulfonamide 80% sodium alkylnaphthalenesulfonate 2% i C sodium Iigninsulfonate 2% synthetic amoφhous silica 3% kaolinite 13% The ingredients are blended, hammer-milled until all the solids are 5 essentially under 50 microns, reblended, and packaged. EXAMPLE 18 Wettable Powder C 3-( 1 -hydroxy-2-fluoroethyl)-N-[(4-methoxy-6-methyl-pyrimidin-2-yl) amino carbonyI]-2-pyridine sulfonamide 50% sodium alkylnaphthalenesulfonate 2% low viscosity methyl cellulose 2% diatomaceous earth 46% The ingredients are blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in diameter. The product is reblended before packaging. EXAMPLE 19 Granule 5 wettable powder of Example 18 5% attapulgite granules(U.S.S. 20-40 mesh ; 0.84 ~ 0.42 mm) 95% A slurry of wettable powder containing 25% solids is sprayed on the surface of attapulgite granules in a double-cone blender. l o The granules are dried and packaged. EXAMPLE 20 Extruded Pellet 5 3-( 1 -hydroxy-2-fluoroethyl)-N-[(4,6-dimethoxypyrimidin-2-yl) amino carbonyl]-2-pyridinesulfonamide 25% anhydrous sodium sulfate 10% crude calcium lignisulfonate 5% sodium alkylnaphthalenesulfonate 1% 0 calcium/magnesium bentonite 59% The ingredients are blended, hammer-milled and then moistened with about 12% water. The mixture is extruded as cylinders about 3 mm diameter which are cut to pioduce pellets about 3mm long. They may be used directly after drying, or 5 the dried pellets may be crushed to pass a U.S.S. No. 20 sieve(0.84 mm openings). The granules held on a U.S.S. No. 40 sieve(0.42 mm openings) may be packaged for use and the fines recycled. EXAMPLE 21 Oil Suspension 3-( 1 -hydroxy-2-fluoroethyl)-N-[(4,6-dimethoxy pyrimidin-2-yl) amino carbonyl]-2-pyridinesulfonamide 25% polyoxyethylene sorbitol hexaoleate 5% highly aliphatic hydrocarbon oil 70% The ingredients are ground together in sand mill until the solid particles have been reduced to under about 5 microns. The resulting thick suspension may be applied directly, but preferably after being extended with oils or emulsified in water. EXAMPLE 22 Wetting Powder 3-( 1 -hydroxy-2-fluoroethyl)-N-[(4,6-dimethoxypyrimidin-2-yl) aminocarbonyl] -2-pyridinesulfonamide 20% sodium alkylnaphthalenesulfonate 4% sodium ligninsulfonate 4% low viscosity methyl cellulose 3% attapulgite 69% The ingredients are thoroughly blended. After grinding in a hammer-mill to produce particles essentially all below 100 microns, the material is reblended and sifted through a U.S.S. No.50 sieve(0.3 mm openings) and packaged. EXAMPLE 23 Low Strength Granule 5 3-( 1 -hydroxy-2-fluoroethyl)-N-[(4,6-dimethoxypyrimidin-2-yl) aminocarbonyl]-2-pyridinesulfonamide 1 % N,N-dimethylformamide 9% attapulgite granule (U.S.S. 20-40 sieve) 90% i c The active ingredient is dissolved in the solvent and the solution is sprayed upon dedusted granules in a double cone blender. After spraying of the solution has been completed, the blender is allowed to run for a short period and then the granules are packaged. 5 EXAMPLE 24 Aqueous Suspension 3-( 1 -hydroxy-2-fluoroethyl)-N-[(4,6-dimethoxy pyrimidin-2-yl) aminocarbonyl]-2-pyridinesulfonamide 40% 0 polyacrylic acid thickener 0.3% dodecylphenol polyethylen glycol ether 0.5% disodium phosphate 1% monosodium phosphate 0.5% poly vinyl alcohol 1% 5 water 56.7% The ingredients are blended and ground together in a sand mill to produce particles essentially all under 5 microns in size. EXAMPLE 25 Solution 5 3-(l-hydroxy-2-fluoroethyl)-N-[(4,6-dimethoxy pyrimidin-2-yl) aminocarbonyI3-2-pyridinesulfonamide, ammonium salt 5% water 95% The salt is added directly to the water with stirring to produce the solution, l c which may then be packaged for use. EXAMPLE 26 Low Strength Granule 5 3-( 1 -hydroxy-2-fluoroethyl)-N-[(4,6-dimethoxy pyrimidin-2-yl) aminocarbonyl] -2-pyridinesulfonamide 0.1 % attapulgite granules (U.S.S. No.20-40 mesh) 99.9% The active ingredient is dissolved in a solvent and the solution is sprayed 0 upon dedusted granules in a double-cone blender. After spraying of the solution has been completed, the material is warmed to evaporate the solvent. The material is allowed to cool and packaged. 97 EXAMPLE 27 Wettable Powder 5 3-(l-hydroxy-2-fluoroethyl)-N-[(4,6-dimethoxy pyrimidin-2-yl) aminocarbonyl]-2-pyridinesulfonamide 40% dioctyl sodium sulfosuccinate 1.5% sodium ligninsulfonate 3% low viscosity methyl cellulose 1.5% i o attapulgite 54% The ingredient are throughly blended, passed through an air mill, to produce an average particle size under 15 microns, reblended, and sifted through a U.S.S. No. 50 sieve(0.3mm opening) before packaging. All compounds of the invension 5 may be formulated in the same manner. EXAMPLE 28 Granule 0 wettable powder of Example 18 15% gypsum 69% potassium sulfate 16% The ingredients are blended in rotating mixer and water sprayed on to 5 accomplish granulation. When most of the material has reached the desired range of 1.0 to 0.42 cm (U.S.S. #18 to 40 sieves), the granules are removed, dried, and screened. Oversized material is crushed additional material in the desired range. These granules contain % active ingredient EXAMPLE 29 High Strength Concentrate 5 3-(l-hydroxy-2-fluoroethyl)-N-[(4,6-dimethoxy pyrimidin-2-yl) aminocarbonyl]-2-pyridinesulfonamide 99% silica aerogel 0.5% synthetic amoφhous silica 0.5% ιc The ingredient are blended and ground in a hammer-mill to produce a material essentially all passing a U.S.S. No. 50 screen (0.3 mm opening). The concentrate may be formulated further if necessary. EXAMPLE 30 5 Wettable Powder 3-( 1 -hydroxy-2-fluoroethyl)-N-[(4-methoxy-6-methyl-pyrimidin-2-yl) aminocarbonyI]-2-pyridinesulfonamide 90% dioctyl sodium sulfosuccinate 0.1% C synthetic fine silica 9.9% The ingredient are blended and ground in a hammer- mill to produce particles essentially all below 100 microns. The material is sifted through a U.S.S. No. 50 screen and the packaged. EXAMPLE 31 Wettable Powder 5 3-(l-hydroxy-2-fluoroethyl)-N-[(4,6-dimethoxy pyrimidin-2-yl) aminocarbonyl)-2-pyridinesulfonamide 40% sodium ligninsulfonate 20% montmorillonite clay 40% i o The ingredients are throughly blended, coarsely hammer-milled and then air- milled to produce particles essentially all below 10 microns in size. The material is reblended and the packaged. EXAMPLE 32 Oil Suspension 3-( 1 -hydroxy-2-fluoroethyl)-N-[(4,6-dimethoxy pyrimidin-2-yl) aminocarbonyl)-2-pyridinesulfonamide 35% blended of polyalcohol carboxylic estes and oil soluble petroleum 6% 0 xylene 59% The ingredients are combined and ground together in a sand mill to produce panicle essentially all below 5 microns. The product can be used directly, extended with oil, or emulsified in water. EXAMPLE 33 Dust 5 3-(l-hydroxy-2-fluoroethyl)-N-[(4,6-dimethoxy pyrimidin-2-yl) aminocarbonyl)-2-pyridinesulfonamide 10% attapulgite 10% pyrophyllite 80% i c The active ingredient is blended with attapulgite and then passed through a hammer-mill to produce particles substantially all below 200 microns. The ground concentrate is then blended with powdered pyrophyllite until homogeneous. EXAMPLE 34 5 Emulsifiable Concentrate 3-( 1 -hydroxy-2-fluoroethyl)-N-[(4,6-dimethoxypyrimidin-2-yl) aminocarbonyl)-2-pyridinesulfonamide 10% chlorobenzene 84% sorbitan monostearate and polyoxyethylene condensates thereof 6% The ingredients are combined and stirred to produce a solution which can be emulsified in water for application. EXAMPLE 35 Pre-emergence test To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with 5 parts by weight of acetone, 1 part by weight of alkylaryl polyglycol ether of emulsifier is added and the concentrate is diluted with water to the desired concentration Seeds of the test plants are shown in normal soil and, after 24 hours, 5 watered with the preparation of the active compound. It is expedient to keep constant the amount of water per unit area. The concentration of the active compound in the preparation is of no importance, only the amount of active compound applied per unit area being desicive. After three weeks, the degree of damage to the plants is rated in % damage in comparison to the i c development of the untreated control. The figures denote : 0% = no action (like untreated control) 20% = slight effect 70% = herbicidal effect 15 100% = total destruction. In this test, the active compounds(I) according to the preparation Examples exhibit a better herbicidal activity against nomo- and dicotyledon weeds. EXAMPLE 36 Post-emergence test To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with 5 parts by weight of acetone, 1 part by weight of alkylaryl polyglycol ether of emulsifier is added and the concentrate is diluted with water to the desired concentration. Test plants which have a height of 5 ~ 15 cm are sprayed with the preparation of the active compound in such a way as to apply the particular amounts of active compound desired per unit area. The concentration of the spray liquor is so chosen that the particular amounts of active compound desired are applied in 2,000 of water/ha. After three weeks, the degree of damage to the plants is rated in % damage in comparasion to the development of the untreated control. The figures denote : 0% = no action (like untreated control) 20% = slight effect 70% = herbicidal effect 100% = total destruction. In this test, the active compounds(I) according to the preparation Examples exhibit a better herbicidal activity against mono- and dicotyledon weeds. It is understood that the specification and examples are illustrative but not limitative of the present invention and that other embodiments within the spirit and scope of the invention will suggest themselves to those skilled in the art. The herbicidal proficiency of the active ingredients of the present invention is evident from the test results which are recorded in following Table 29. The following Table 29 below is represented pre- and post-emergence herbicidal evaluation [PRIMARY SCREENING (Herbicide)] of following "test compounds". PLANT RESPONSE SCREENING (Herbicide) Cornpound TYPE JgΛia SORBI ECHOR BROJA DIGSA PANDI SOLNI AESIN ABUTH XANSI CAGHE no, (SETVI) [AGRSM] 1 PRE .05 100 100 100 100 100 50 90 100 100 100 POST .05 100 100 100 100 100 50 100 100 100 100 2 PRE .05 100 100 (100) 100 100 30 80 90 100 POST .05 100 100 (100) 100 100 20 100 90 100 100 3 PRE .05 90 60 [0] 50 100 0 0 0 0 85 POST .05 90 100 [70] 90 100 60 25 20 50 70 4 IRE .05 100 100 [90] 100 100 100 80 90 90 100 POST .05 100 100 [100] 100 100 70 100 90 100 100 5 PRE .05 100 100 [50] 100 100 65 30 90 85 100 POST .05 100 100 [60] 100 100 60 90 85 100 100 6 PRE 4 100 100 [100] 100 100 100 100 90 100 100 POST 4 100 100 [100] 100 100 100 100 100 100 100 7 PRE 4 100 100 [90] 100 100 100 90 100 90 100 POST 4 100 100 [100] 100 100 100 100 100 100 100 S PRE 4 100 100 [90] 1O0 100 100 100 90 90 100 POST 4 100 100 [100] 100 100 100 100 100 100 100 9 PRE 4 100 100 [100] 100 100 100 100 90 90 100 POST 4 100 100 [100] 100 100 100 100 100 100 100 10 PRE 4 100 100 [90] 100 100 100 90 90 90 100 POST 4 100 100 [100] 100 100 100 100 90 100 100 PLANT RESPONSE SCREENING (Herbicide) Compound TYPE kg/ha SORBI ECHOR BROJA DIGSA PANDI SOLNI AESIN ABUTH XANSI CAGHE no, (SETVI) [AGRSM] 11 PRE .05 100 90 [70] 95 90 30 40 75 90 100 POST .05 60 100 [50] 60 80 0 90 65 90 85 12 PRE .05 100 100 [90] 95 100 80 65 80 85 100 POST .05 100 100 [80] 100 100 40 100 80 100 60 13 PRE .05 90 70 [20] 50 90 90 0 25 60 60 POST .05 70 65 [15] 0 60 30 20 0 70 60 14 PRE 4 100 100 [90] 100 100 100 100 90 100 100 POST 4 100 100 [100] 100 100 100 100 100 100 100 15 PRE 4 100 100 [90] 100 100 100 100 90 90 100 POST 4 100 100 [100] 100 100 100 100 100 100 100 16 PRE 4 100 90 [90] 100 100 100 70 90 90 100 POST 4 100 100 [80] 100 100 100 100 90 100 100 17 PRE 4 100 100 [90] 100 100 100 90 90 90 100 POST 4 100 100 [90] 100 100 100 100 100 100 100 18 PRE 4 90 90 [70] 100 100 100 85 90 90 100 POST 4 100 100 [70] 100 100 100 90 80 90 100 19 PRE .05 100 100 [90] 100 100 70 30 80 90 95 POST .05 100 100 [70] 65 100 30 100 70 100 70 20 PRE .05 100 90 [80] 100 90 60 20 60 90 100 POST .05 90 100 [65] 60 90 10 65 30 80 70 PLANT RESPONSE SCREENING (Herbicide) 1 PRE .05 100 80 [60] 65 50 30 0 0 45 70 POST .05 100 80 [0] 0 65 20 0 0 35 20 2 PRE .05 100 100 [50] 100 100 60 50 85 90 100 POST .05 100 100 [40] 100 100 60 100 90 90 90 3 PRE .05 90 90 [40] 100 100 60 50 90 90 100 POST .05 90 65 [55] 60 60 30 80 85 90 85 PRE .05 0 0 [0] 15 50 0 0 10 0 0 POST .05 0 0 [0] 0 0 0 0 0 0 0 PRE .05 0 0 [0] 0 0 0 0 0 0 65 POST .05 0 0 [0] 0 0 0 0 0 0 10 PRE .05 20 10 [0] 0 0 0 0 0 0 0 POST .05 0 0 [0] 0 0 0 0 0 0 0 PRIMARY SCREENING (Herbicide) Compound TYPE kg/ . ZEΛMX GLXMX GOSHI TRZAW ORYSA SORBI ECHOR BROIA DIGSA PANDI SOLNI AESIN ABUTH XANSI CAGHE no, (SETVI) [AGRSM] PRE .1 100 100 100 100 100 100 100 (100) 100 100 70 70 100 100 100 .05 100 100 100 100 100 100 100 (100) 100 100 40 60 100 100 100 .025 70 100 100 100 100 100 100 (100) 100 100 0 40 90 100 100 .0125 60 100 70 100 100 100 100 (100) 100 100 0 30 80 70 100 .00625 40 70 40 65 100 100 90 (100) 100 100 0 0 60 70 100 .025 80 100 70 100 100 100 100 (90) 100 100 50 65 90 100 100 .0125 70 90 70 90 100 100 90 (85) 100 100 40 40 80 90 100 .00625 40 80 50 80 100 100 85 (80) 100 100 40 30 70 100 .003125 0 65 50 75 100 90 80 (70) 100 100 30 20 70 100 .00151 0 50 40 40 70 80 70 (70) 100 100 30 0 50 60 PRIMARY SCREENING (Herbicide) Compound TYPE kg/h. ZEΛMX GLXMX GOSiπ TRZA ORYSA SORBI ECHOR BROIA DIGSA PANDI SOLNI AESIN ABUTH XANSI CAGHE no, (SETVI) [AGRSM] POST .1 100 100 100 100 100 100 100 (100) 100 100 100 100 100 100 .05 100 100 90 100 100 100 100 (100) 100 100 100 100 100 100 .025 100 100 70 100 100 100 100 (100) 100 100 100 100 100 100 .0125 70 100 60 80 100 100 100 (100) 100 100 90 100 100 90 .00625 30 100 20 70 100 100 100 (100) 100 100 60 80 70 80 .025 80 100 60 90 90 100 100 (100) 100 100 40 100 100 100 100 .0125 70 100 50 90 95 100 100 (100) 100 100 40 100 100 100 100 .00625 60 100 30 65 90 100 100 (100) 100 90 20 100 100 100 100 .003125 0 30 75 0 60 90 100 (90) 90 80 0 60 60 95 65 .00151 0 70 0 50 70 100 100 (80) 90 80 0 50 50 65 65 PRIMARY SCREENING (Herbicide) Compound TYPE kg/hi ZEΛMX GLXMX GOSHI TR7AW ORYSA SORBI ECHOR BROTA DIGSA PANDI SOLM AESIN ABUTH XANSI CACHE no, (SETVT) [AGRSM] 100 80 (90) 100 100 40 60 70 90 100 100 95 (80) 100 100 20 20 40 90 100 80 75 (70) 95 100 0 0 20 40 100 20 50 (30) 80 90 0 0 0 0 100 100 100 (100) 100 90 70 80 100 100 100 60 100 (90) 100 90 30 60 60 100 100 50 90 (90) 80 90 10 40 60 90 90 40 60 (90) 70 30 10 20 40 60 60 PRIMARY SCREENING (Herbicide) Compound TYPE kg/h« ZEΛMX GLXMX OOSiπ TRZAW ORYSA SORBI ECHOR BROJA DIGSA PANDI SOLNI AESIN ABUTH XANSI CAGHE no, (S-TVI) [AGRSM] 4 PRE .1 80 100 100 100 100 100 100 [90] 100 100 80 65 100 100 100 .025 70 70 80 100 100 100 100 [70] 100 100 60 10 65 70 100 .006 30 30 50 60 100 100 70 [40] 100 100 20 0 20 40 100 .00156 0 0 0 0 50 60 30 [0] 40 70 0 0 0 0 20 .00039 0 0 0 0 0 0 0 [0] 0 0 0 0 0 0 0 POST .l 100 100 70 100 100 100 100 [100] 100 100 60 70 90 100 100 .025 50 100 20 100 100 100 100 [70] 100 100 60 60 70 100 100 .006 0 100 0 50 100 70 100 [60] 100 100 30 20 40 50 80 .00156 0 40 0 0 70 70 80 [20] 70 70 0 0 0 30 40 .00039 0 0 0 0 0 30 50 [0] 0 65 0 0 0 0 0 PRIMARY SCREENING (Herbicide) Compound TYPE kg/h» ZEAMX GLXMX GOSHI TRZAW ORYSA SORBI ECHOR BROJA DIGSA PANDI SOLNI AESIN ABUTH XANSI CAGHE no, (SETVI) [AGRSM] 100 100 100 100 [100] 100 100 60 30 70 65 100 100 90 [50] 100 100 20 0 20 20 70 100 20 [0] 20 90 0 0 0 0 10 20 0 [0] 0 40 0 0 0 0 0 0 0 [0] 0 0 0 0 0 100 100 100 100 [50] 100 100 50 70 60 90 100 100 100 [40] 100 100 40 40 50 30 60 60 70 [0] 30 90 0 20 0 0 0 0 0 [0] 0 60 0 0 0 0 0 0 0 [0] 0 0 0 0 0 PRIMARY SCREENING (Herbicide) Compound TYPE kg/tit ZEAMX GLXMX GOSHI TRZAW ORYSA SORBI ECHOR BROJA DIGSA PANDI SOLNI AESIN ABUTH XANSI CAGHE no, (SETVD [AGRSM] (. PRE .1 100 100 100 100 100 100 100 [100] 100 100 70 100 100 100 100 .025 100 100 100 100 100 100 100 [100] 100 100 60 30 100 100 100 .00625 100 60 70 70 100 100 100 [60] 100 100 40 0 50 90 80 .00156240 30 40 30 100 90 60 [0] 80 100 0 0 0 30 30 .00039 0 0 0 0 70 0 0 [0] 0 0 20 0 0 0 0 POST .l 100 100 90 100 100 100 100 [100] 100 100 100 100 100 100 100 .025 100 100 80 100 100 100 100 [100] 100 100 50 100 80 100 100 .00625 100 100 70 90 100 100 100 [70] 100 100 30 60 70 100 60 .001562 40 80 40 30 100 80 80 [30] 60 90 0 0 0 60 50 .00039 0 30 0 0 60 60 40 [0] 0 60 0 0 0 0 20 ______ , , . PRIMARY SCREENING (Herbicide) Compound TYPE kg/ht ZEΛMX GLXMX GOSHI TRZAW ORYSA SORBI ECHOR BROJA DIGSA PANDI SOLNI AESIN ABUTH XANSI CAGHE no, (SETVI) [AGRSM] 100 100 100 100 [80] 100 100 70 20 60 70 100 60 100 100 100 [40] 100 100 40 0 0 65 60 30 100 90 70 [0] 30 40 20 0 0 40 30 0 60 60 20 [0] 0 0 0 0 0 0 0 0 40 0 0 [0] 0 0 0 0 0 0 0 100 100 100 100 [100] 100 100 100 65 40 100 100 100 [80] 100 100 100 40 20 100 70 50 [30] 40 80 30 0 0 50 50 20 [0] 0 30 0 0 0 0 20 0 [0] 0 0 0 0 PRIMARY SCREENING (Herbicide) Compound TYPE kg/h « ZEΛMX GLXMX GOSHI TRZΛW ORYSA SORBI ECHOR BROJA DIGSA PANDI SOLM AESIN ABUTH XANSI CAGHE no, (SETVT) [AGRSM] 100 100 70 [30] 65 80 20 0 60 60 20 [0] 20 60 0 0 20 0 0 [0] 0 0 0 0 0 0 0 [0] 0 0 0 0 [0] o 100 60 [30] 30 100 0 70 40 [0] 0 0 0 0 0 [0] 0 0 0 0 0 [0] 0 0 0 0 0 [0] 0 0 0 PRIMARY SCREENING (Herbicide) Compound TYPE kg h« ZEAMX GLXMX GOSHI TRZAW ORYSA SORBI ECHOR BROJA DIGSA PANDI SOLM AESIN ABUTH XANSI CAGHE no, (SETVI) [AGRSM] 100 70 60 [60] 80 100 20 20 70 80 70 65 20 40 [0] 40 50 0 0 0 30 20 20 0 0 [0] 30 0 0 0 0 0 0 0 0 0 [0] 0 0 0 0 0 0 0 0 0 0 [0] 0 0 0 0 0 0 0 50 100 [50] 80 70 0 30 [0] 0 0 0 0 [0] 0 0 0 0 [0] 0 0 0 0 [0] 0 0 PRIMARY SCREENING (Herbicide) Compound TYPE kg/h« ZEAMX GLXMX GOSiπ TRZΛW ORYSA SORBI BCHOR BROJA DICSA PANDI SOLM AESIN ABUTH XANSI CAGHE no, PETVI) [AGRSM] PRIMARY SCREENING (Herbicide) Compound TYPE kg/h> ZEΛMX CLXMX GOSHI TRZAW ORYSA SORBI ECHOR BROJA DIGSA PANDI SOLM AESIN ABUTH XANSI CAGHE no, (SETVT) (AGRSM] 14 PRE .1 100 100 90 100 100 100 100 [100] 100 100 70 80 100 100 100 .025 20 90 80 100 100 100 100 [70] 100 100 40 50 70 90 100 .00625 0 60 50 50 100 100 70 [30] 60 100 0 0 50 80 70 .00156 0 20 0 0 50 50 40 [0] 0 80 0 0 0 30 30 .00039 0 0 0 0 0 0 0 [0] 0 0 0 0 0 0 0 POST.1 90 100 60 100 100 100 100 [90] 100 100 60 100 90 100 100 .025 40 100 40 90 90 100 100 [60] 100 100 50 100 60 100 100 .00625 0 80 0 50 90 100 70 [40] 40 90 0 40 50 100 40 .00156 0 60 0 20 50 50 50 [0] 0 90 0 0 0 40 20 .00039 0 30 0 0 20 0 0 [0] 0 60 0 0 0 0 0 PRIMARY SCREENING (Herbicide) Compound TYPE kg/hi ZEΛMX CLXMX GOSHI TRZΛW ORYSA SORBI ECHOR BROJA DIGSA PANDI SOLM AESIN ABUTH XANSI CAGHE no, CSETVI) [AGRSM] 15 100 100 100 [60] 100 100 30 40 100 80 80 [0] 100 90 0 0 40 0 20 [0] 50 80 0 0 0 0 0 [0] 0 20 0 0 0 0 0 [0] 0 0 0 0 100 70 100 [70] 100 100 70 80 90 40 90 [30] 50 80 0 50 40 0 60 [0] 0 20 0 20 0 0 0 [0] 0 0 0 0 [01 PRIMARY SCREENING (Herbicide) Compound TYPE kg/hi ZEΛMX C XMX GOSHI TRZAW ORYSA SORBI ECHOR BROJA DIGSA PANDI SOLM AESIN ABUTH XANSI CAGHE no. (SETVI) [AGRSM] PRIMARY SCREENING (Herbicide) Compound TYPE kg/hi ZEAMX CLXMX GOSHI TRZAW ORYSA SORBI ECHOR BROJA DIGSA PANDI SOLM AESIN ABUTH XANSI CACHE no, (SE VT) (AGRSM] 17 PRE .1 0 70 50 60 100 100 100 [50] 100 100 80 0 40 70 70 .025 0 0 20 40 100 90 70 [30] 40 90 40 0 0 40 40 .00625 0 0 0 30 50 30 20 [0] 0 40 20 0 0 0 0 .00156 0 0 0 0 20 0 0 [0] 0 0 0 0 0 0 0 .00039 0 0 0 0 0 0 0 [0] 0 0 0 0 0 0 0 100 100 [50] 100 100 60 40 30 90 40 60 100 [0] 50 80 40 0 0 60 20 20 60 [0] 0 0 0 0 0 20 0 0 0 [0] 0 0 0 0 0 0 0 0 0 [0] 0 0 0 0 0 0 0 PRIMARY SCREENING (Herbicide) Compound TYPE kghi ZEAMX CLXMX GOSHI TRZAW ORYSA SORBI ECHOR BROJA DIGSA PANDI SOLM AESIN ABUTH XANSI CACHE no, (SETVI) [AGRSM] 100 100 100 [80] 100 100 80 20 100 80 70 [20] 50 100 40 0 70 50 0 [0] 0 70 0 0 0 0 0 [0] 0 0 0 0 0 0 0 [0] 0 0 0 0 100 100 100 [80] 100 100 70 70 70 100 90 [40] 20 90 40 40 30 40 40 [0] 0 40 30 0 0 0 0 [0] 0 0 0 0 0 0 0 [0] 0 0 0 0 PRIMARY SCREENING (Herbicide) Compound TYPE kg/h« ZEAMX GLXMX GOSHI TRZAW ORYSA SORBI ECHOR BROJA DIGSA PANDI SOLM AESIN ABUπi XANSI CAGHE no, (SETVI) [AGRSM] 100 100 [70] 100 100 60 30 70 100 70 20 20 [20] 30 30 0 0 10 100 50 0 0 [0] 0 0 0 0 0 30 0 0 0 [0] 0 0 0 0 0 0 0 0 0 [0] 0 0 0 0 0 0 0 90 100 [50] 50 60 40 50 [0] 0 0 0 0 [0] 0 0 0 0 [0] 0 0 0 0 [0] 0 0 PRIMARY SCREENING (Herbicide) Compound TYPE kg/hi ZEAMX CLXMX GOSHI TRZAW ORYSA SORBI ECHOR BROJA DIGSA PANDI SOLM AESE. ABUTH XANSI CACHE no, (XBTVI) [AGRSM] 22 PRE .1 100 100 100 20 100 100 100 [40] 100 100 70 100 100 100 100 .025 100 100 80 0 100 100 100 [30] 90 90 60 60 80 70 100 .00625 90 50 40 0 60 80 80 [0] 50 60 20 20 70 30 30 .001562 30 40 0 0 40 30 20 [0] 0 20 0 0 0 0 20 .00039 0 20 0 0 20 0 0 [0] 0 0 0 0 0 0 0 POST.l 100 100 100 60 100 100 100 [50] 100 100 100 100 100 100 100 .0025 100 100 80 10 50 100 100 [30] 80 100 50 40 70 100 50 .00625 70 70 40 0 30 60 40 [0] 40 40 40 30 60 60 40 .00156220 40 0 0 0 20 0 [0] 0 0 30 0 0 20 30 .00039 0 0 0 0 0 0 0 [0] o o o o o o o PRIMARY SCREENING (PADDY SUBMERGED)-HERBICIDE Compound DAT kg*» ORYSA ORYSA ECHOR SCPJU MOOVA CYPSE SAGPY no. ( . Leaf) («eed) 100 70 100 90 80 70 50 PRIMARY SCREENING (PADDY SUBMERGED)-HERBICIDE Compound DAT kgΛia ORYSA ORYSA ECHOR SCPJU OOVA CYPSE SAGPY no. (3L_-i) freed) 12 .05 90 90 90 90 90 90 90 .05 100 100 100 100 100 100 100 025 100 100 100 100 100 100 100 .0125 100 100 100 100 100 100 100 .006 100 100 70 100 100 100 100 Λ03 80 90 50 70 100 100 100 .05 100 100 100 95 90 100 100 .0125 40 70 40 60 50 70 100 .003 0 0 0 0 0 0 0 .00078 0 0 0 0 0 0 0 .0002 0 0 0 0 0 0 0 19 PRIMARY SCREENING (PADDY SUBMERGED)-HERBICIDE 22 .05 60 60 60 90 90 100 90

Claims: WHAT IS CLAIMED IS 1. Compounds of Pyridine sulfonyl urea derivatives having the structure of following general formula(I) o w II II P-S-NH-C-N-A ( I ) II I O R 3 wherein, P is P-l, P-2, P-3 or P-4 as follows ; (P-3) (P-4) E is single bond or CH 2 ; R 1 is H, C,-C 3 alkyl, C ,-Cj haloalkyl, halogen, CN, N0 2 , C r C 3 alkoxy, C.- haloalkoxy, SO^R'R 11 , Cj-Q alkylthio, - alkylsulfinyl, C r C 3 alkylsulfonyl, SCH 2 F, NH 2 , NHCH 3 , N(CH 3 ) 2 , C r C 2 alkyl substituted with C j -C, alkoxy, C j - haloalkoxy, SH, SCH 3 , CN or OH or C0 2 R m ; and then R ~ is H, C r C 4 alkyl, - cyanoalkyl, methoxy or ethoxy ; R π is H, C C 4 alkyl, C 3 - alkenyl, or when taken together, connecting R 1 and R π , -(CH^-, -(CH^-, -(CH-V or CH j CH j OCH j CIl j -, may be formed ; R m is C r C 4 alkyl, .C 3 -C 4 alkenyl, C 3 -C 4 alkynyl, C r C 4 alkyl substituted with 1 ~ 2 halogen or cyano groups, - cycloalkyl, C 3 -Cj cycloalkylalkyl or C 2 -C 4 alkoxyalkyl ; R 2 is C j - alkyl substituted with 1 ~ 3 halogen ; R 3 is H or CH 3 ; W is O or S ; A is Al, A2, A3, A4, A5, A6 or A7 as following ; A l A 2 A 3 A 4 A 5 A 6 A 7 wherein, X is H, C r C 4 alkyl, C j -C 4 alkoxy, C r C 4 haloalkoxy, C r C 4 haloalkyl, C,-C 4 haloalkylthio, C r C 4 alkylthio, halogene, C j -G j alkoxyalkyl, Gr alkoxyalkoxy, amino, C j -C, alkylamino, diCC j - alkyl) amino or C 3 -C 5 cycloalkyl ; Y is H, C r C 4 alkyl, C,-C 4 alkoxy, C r C 4 haloalkoxy, C r C 4 haloakylthio, C r C 4 alkylthio, C 2 -C 3 alkoxyalkyl, C 2 -G ; alkoxyalkoxy, amino, C r C 3 alkylamino, diCC j - alkyl)amino, C 3 -C 4 alkenyloxy, C J -C J 5 alkylthioalkyl, C r C 4 haloalkyl, C 2 -C 4 alkynyl, azido, cyano, C 2 -G; alkylsulfinylalkyl, C 2 - alkylsulfonylalkyl, CYLβH, C 3 -C 5 cycloalkyl, G j - cycloalkoxy, C 3 -C 4 O II I o alkynyloxy, -C-R 6 , CH 3 I 5 or -N-OCH 3 ; m is 2 or 3 ; L 1 and L 2 are independently O or S ; R 4 and R 5 are independently C,- alkyl ; R 6 is H, or CH 3 ; Y 1 is O or CH 2 ; X 1 is CH 3 , OCH 3 , OC^ or OCHF 2 ; Y 3 is H or CH 3 ; Y 2 is CH 3 , O^CH,, OCH 3 , OCH j CH,, SCH 3 or SCH 2 CH, ; 5 X 2 is CH,, CH^CH,, or CH^CF, ; X 3 is CH, or OCH 3 ; Y 4 is CH,, OCH 3 , O ^H j , C¥L,OCH 3 or Cl ; X 4 is CH 3 , OCH 3 , OC j Hs, CI^OC^ or Cl ; and these may be an agriculturally suitable salt, 0 and then, (1) if X is Cl, Br, F or I, Z is CH and Y is OCH,, OC^, NCH 3 (OCH 3 ), NH,, NHCH 3 , N(CH,) 2 or OCHF 2 ; (2) if X or Y is OCHF 2 , Z is CH ; 5 (3) X 4 and Y 4 are not Cl simultaneously ; (4) if W is S, R 3 is H, A is A Zis CH or N and , Y is CH 3 , OCH 3 , OCH j CH,, CH j OCHs, C^, CF 3 , SCH,, OCH j O^CH,, (5) if a number of total carbon atoms X and Y are more than 4, a number of carbon atoms of R 2 is 4 or less than 4. 5 2. Compounds as defined in the claim 1, wherein E is single bond, W is O, and R 3 is H. 3. Compounds as defined in the claim 1, wherein R 1 is selected from the group consisting of H, halogen, C j -C j alkyl, C^G j alkoxy, C j -C^ haloalkyl, C j -C- C alkylthio, haloalkoxy and CH 2 CN ; X is selected from the group consisting of C j - alkyl, C j -Q alkoxy, Cl, F, Br, I, OCHF 2 , CH 2 F, CF 3 , OCH j CH-F, OCH 2 CHF 2 , OCH 2 CF 3 , CH 2 C1 and CH 2 Br ; and Y is H, Q-Q alkyl, C r C 2 alkoxy, CH 2 OCH„ CH C^CH,, NHCH 3 , N(OCH 3 )CH,, N(CH 3 ) 2 , CF 3 , SCH 3 , OCH 2 CH=CH 2 , OCH 2 C≡CH, CH ^, OCH j CH CH,, CH j SCH,, OCHF 2 , OCF 2 Br, SCHF 2 , cyclopropyl, C ≡ CH or C≡C-CH 3 , and then R 4 and R 5 are C j - alkyl, R 6 is H or CH 3 , L 1 and L 2 are O or S and m is 2 or 3 . 4. Compounds as defined in the claim 1, wherein P is P-l ; Z is CH ; X is CH 3 , C 2 Hi, OCH 3 , OCH 2 CH,, Cl or OCHF 2 ; Y is CH 3 , OCH 3 , OC-Hs, QH j , CH 2 OCH 3 , NHCH 3 , CH(OCH 3 ) 2 or cyclopropyl. 5. Compounds as defined in the claim 1, wherein R 2 is CH 2 F, C^CH^F, CHF-CH 3 , CH 2 C1, CH 2 Br, CHC1 2 , CHFCl, CH^Cl, CHC1CH 3 , CHF 2 , CHC1-CH 2 C1, CHFCH 2 C1, CHF-CH or CH 2 CHF 2 . 6. Compounds as defined in claim 1, wherein said general formula(I) is 3-(l- hydroxy-2-fluoroethyl)-N-[(4,6-dime_hoxypyrimidin-2-yl)aminocarbonyl]- 2-pyridinesulfonamide. 7. Compounds as defined in claim 1, wherein said general formula(I) is 3-(l- hydrox y-2-fluoroethyl )-N-[(4-methosy-6- methyl-pyrimidin- 2- yl)aminocarbonyl]-2-pyridinesulfonamide. 8. Compounds as defined in claim 1, wherein said general formula(I) is 3-(l- hydroxy-2- fluoroethy l)- N-[(4-chrolo- 6-methoxy -pyrimidin-2- yl)aminocarbonyl]-2-pyridinesulfonylamide. 9. Compounds as defined in claim 1, wherein said general formula(I) is 3-(l- hydroxy-2-fluorc«thyl)-N-[(4,6-dimethyl-py__midin-2-yl)aminoca_ )onyl]-2- pyridinesulfonylamide. 10. Compounds as defined in claim 1, wherein said general formula(I) is 3-(l- hydroxy-2-fluoroethyl)-N-[(4-chloro-6-ethoxy-pyrimidin-2-yl) aminocarbonyl]-2-pyridinesulfonylamide. 5 11. Compounds as defined in claim 1, wherein said general formula(I) is 3-(l- hydroxy-2-fluoropropyl)-N-[(4,6-dimethoxy-pyrimidin-2-yl)amino carbonyl]-2-pyridinesuIfonylamide. ic 12. Compounds as defined in claim 1, wherein said general formula(I) is 3-(l- hydroxy-2-fluoropropyl)-N-[(4-methyl-6-methoxy-pyrimidin-2-yl) amiπocarbonyl]-2-pyridinesulfonylamide. 13. Compounds as defined in claim 1, wherein said general formula(I) is 3-(l- 5 hydroxy-2-fluoropropyl)-N-[(4,6-cUmethyl-pyrimidin-2-yl)aminoca_l)onyl]- 2-pyridinesulfonyIamide. 14. Compounds as defined in claim 1, wherein said general formula(I) is 3-(l- hydroxy-2-fluoropropyl)-N-[(4-chlθ-O-6-methoxy-pyrimi_lin-2-yl)amino C carbonyl]-2-pyridinesulfonylamide. 15. Compounds as defined in claim 1, wherein said general formula(I) is 3-(l- hydroxy-2-chIoroethyl)-N-[(4,6-dimethoxy-pyrimidin-2-yl)aminocarbonyl]- 2-pyridine sulfonylamide. 16. Compounds as defined in claim 1, wherein said general formula(I) is 3-(l- hydroxy-2-chloroethyl)-N-[(4-methoxy-6-methyl-pyrimidin-2-yl) aminocarbonyl]-2-pyridinesulfonylamide. 17. Compounds as defined in claim 1, wherein said general formula(I) is 3-(l- hydroxy-2-chloroethyl)-N-[(4,6-dimethyl-pyrimidin-2-yl)aminocarbonyl]-2- pyridinesulfonylamide. 5 18. Compounds as defined in claim 1, wherein said general formula(I) is 3-(l- hydroxy-2-chloroethyl)-N-[(4-chloro-6-methoxy-pyrimidin-2-yl) aminocarbonyl]-2-pyridinesulfonylamide. l o 19. Compounds as defined in claim 1, wherein said general formula(I) is 3-(l- hydro xy-2- fluoroethyl)- N- [(4-methoxy-6-methyl-triazin-2-yl) aminocarbonyl]-2-pyridinesulfonylamide. 20. Compounds as defined in claim 1, wherein said general formula(I) is 3-(l- 5 hydroxy-2-fluorobutyl)-N-[(4,6-c_;met-ioxy-pyrimidin-2-yl)aιninocarbonyl]- 2-pyridinesulfonylamide. 21. Compounds as defined in claim 1, wherein said general formula . I) is 3-(l- hydroxy-2-chloropropy l)-N-[(4,6-dimethoxy-pyrimidin- 2-yl) o aminocarbonyl]-2-pyridinesulfonylamide. 22. Compounds as defined in claim 1, wherein said general formula(I) is 3-(l- hydroxy-2-fluoroethyl)-N-[ (4-chloro-6-methoxy-triazin- 2-yl) aminocarbonyl]-2-pyridinesulfonylamide. 5 23. Compounds as defined in claim 1, wherein said general formula(I) is 3-(l- hydrox y-2-chloroethyl)-N-[(4-methoxy-6-methyl-triazin-2-y l) aminocarbonyl]-2-pyridinesulfonylamide. 24. Compounds as defined in claim 1, wherein said general formula(I) is 3-(l- hydroxy-2-chloroethyl)-N-[(4-chloro-6-methoxy-triazin-2-yl) aminocarbonyI]-2-pyridinesulfonylamide. 5 25. Compounds as defined in claim 1, wherein said general formula(I) is 3-(l- hydroxy-2-fluoropropyl)-N-[(4-methoxy-6-methyl-triazin-2-yI) aminocarbonyl]-2-pyridine sulfonylamide. ιc 26. Compounds as defined in claim 1, wherein said general formula(I) is 3-(l- hydroxy-2-fluoropropyl)-N-[(4-chloro-6-methoxy-triazin-2-yl) aminocarbonyl]-2-pyridinesulfonylamide. 27. Compounds as defined in claim 1, wherein said general formula(I) is 2-(l- 5 hydroxy-2-fluoroethyl)-N-[(4,6-dimemoxy-pyrimidin-2-yl)aminocarbonyl]- 3-pyridinesuIfonylamide. 28. Compounds as defined in claim 1, wherein said general formula(I) is 2-(l- hydroxy-2-fluoroethyl)-N-[(4-methoxy-6-methyl-pyrimidin-2-yl) C aminocarbonyl]-3-pyridinesulfonylamide. 29. Compounds as defined in claim 1, wherein said general formula(I) is 2-(l- hydroxy-2-fluoroethyl)-N- [(4-methyl-6-methoxy-triazin-2-yl ) aminocarbonyl]-3-pyridinesulfonylamide. 30. Intermediate compounds of the formula(I) in the claim 1 having the following general formula(II) wherein, R 1 , R 2 , R 3 , E, W and A are respectively as defind in the above claim 1. 31. Compounds as defined in the claim30, wherein, R 1 is H ; R^s CH j F, CH-C1, CHF 2 , CHFCH 3 or CH j CH j F ; R 3 is H ; A is A x ; and W is O. 32. Intermediate compounds of the formula(I) in the claim 1 having the following general formula(IV) wherein, R 1 and R 2 are respectively as defined in the above claim 1 ; Ac is acetylgroup or protected group regenerating hydroxy group by seperating under the condition of acid or alkali. 33. Compounds as defind in the claim 32, wherein R - is H, Ac is acetyl group, R 2 is C, ~ C 6 alkyl group substrated with 1 ~ 3 halogens. 34. Compounds as defined in the claim 32, wherein R 2 is CH 2 F, CHF 2 , CHjCl, CHFCH 3 , CHC1CH 3 or CH j L . 35. Compounds as defined in the claim 32, wherein said formula(_V) is 3-(l- acetoxy-2-fluoroethyl)-2-pyridinesulfonamide. 36. Compounds as defined in the claim 32, wherein said formuIa(IV) is 2-(l- acetoxy-2-fluoroethyl)-3-pyri__.nesulfonamide. C 37. Herbicides containing at least one of the following general foimula(I) of pyridine sulfonyl urea derivatives as an active ingredient O W II II P— S — NH — C— N — A ( I ) II I q O R wherein , P, W, R 3 and A are respectively as defined in said claim 1. 38. A method for controlling weeds by which apply effective amount of at least one of the following general fσrmula(I) of pyridine sulfonyl urea derivatives in weedy area at pre-emergence or post-emergence O W P— S — NH — C — N — A ( I ) II I o R , 3 * wherein P, W, R 3 and A were repectivly as defined in said claim 1. 39. Herbicide compositions being mixed at least one of the following general ■ formula(I) of pyridine sulfonyl urea derivatives as effective ingredient with other agricultural chemicals thereof o w II II P— S — NH — C — N — A ( I ) O R 3 wherein P, W, R 3 and A are respectively as defined in said claim. 1.

Inventors: CHANG HAE SUNG, JO IN HO, KIM DAE-WHANG, RYU JAE WOOK, CHANG, HAE, SUNG, JO, IN, HO, KIM, DAE-WHANG, RYU, JAE, WOOK
Applicants: KOREA RES INST CHEM TECH, KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY
Application year: 1992
Main classification: C07D213
IPC codes: A01N47, C07D213, C07D401, C07D491, C07D521