PL114069B1 - Agent for undesirable vegetation control and for plant growth regulation - Google Patents

Description

The subject of the invention is an agent for combating undesirable growth, otherness and for regulating the growth of a plant, containing an 'active substance': N- / heterocyclo, minocarbonyl / -aryl sulfonamide. 1468747 Pall-position primary p-enylsulfamides of formula 13 are known, wherein P is hydrogen or halogen, the radical trifluo ["methyl-y or an alkyl radical". These compounds are useful as anti-diabetes agents. Logeman et al., Chem. Ab., 53, 18052 g (1959) disclose a number of sulfonamides including uracyl derivatives and compounds of formula 14 wherein R is butyl, phenyl, or the O 'radical of formula 15, in which R 1 is hydrogen a, or a methyl radical. These compounds were tested in rats at oral doses of 25 mg / 100 g. in order to establish their ability to lower blood sugar levels, with which was found to be the most potent compound of formula 14, in which R is butyl or phenyl rhodium, while t others work .sl ~ because or 'do not show azure at all.J. Woj-ciechow'ski, A cta Polon. Pharm. 19, pp. 121-125 (1962) [ehem.Ah., 59, 1033e] describes the syn of thesis N - [/ 2,-dimethdxypyrimidinyl-41-amino-amino] -4-methylbenzenesulfonam, 16 and based on the similarity of the structure of this compound with formula f6 to the concentration of sugar in the blood. 114 GIl Z Dutch patent specification No. 121788 discusses the method of producing and using general or selective herbicidal compounds of formula 17, where R 1 l and R 2 ISa are the same or different and represent almyl radicals with 1-4 carbon atoms, and R s and R (are the same or different and represent hydrogen atoms, chlorine atoms or alkyl radicals) of 1-4 carbon atoms. The publication and J. Drug Res. 6, 123 (1974) discusses compounds of formula 18 in which Y'm R is a pyridyl radical, and the action of It is known that undesirable vegetation causes 15 significant damage to the cultivation of used crops, especially those that satisfy basic needs. To "human in terms of food and fiber products, such as cotton, rice, corn, wheat, soybeans, etc. These needs grow Vv" 20 due to the significant growth of the population, also , it is necessary to increase the harvest of the above-mentioned plants. Cleaning up n-undamaged plants or limiting their growth will prevent loss, therefore, and reduce valuable crops or limit the 'S'trate. -. Numerous means of destroying damage are known. the vegetation or the halting (controlled) of its growth, including the middle and the usual means, which are vasicidal. Nevertheless, there is a need for very, more effective114 069 3 herbicides that would allow the destruction of varieties or inhibit their growth without causing significant damage to Ifoslin crops used, cumulative. ~ those, e.g. tiboras, are very positive to kill, zanie, and land, a total of 5 known herbicides used to combat Ciboras are non-selective; therefore, they can express more codes and Crop plants: according to the invention, it enables the selective or general control of undesirable vegetation 10 and 9 effectively both for pre-emergence and post-emergence application of plants. It is particularly effective at ~ it fights: ni'U tibory, and at the same time it causes n'~ n'even.only s ~ odes to cultivated plants, yes, i1m, like cotton, rice, hens, lemons, and others.anodek \ ve8lhg · invention, obdk, contains at least an enteric surfactant and (either liquid or solid l'oz ~ s) as A natural c'O component naively ~ one new N- / heterocycle 10aminocarlxmyil! 0 / -arylsulfonamide 'O with the general formula z 1. ~ one group of compounds of formula 1 are compounds in which R is of formula 4 or 5, in which x. denotes a hydrogen, chlorine or, brqplu, methyl, alkoxy radical <1-3 carbon atoms or methylthio, and is a methyl or methoxyl radical, R 1 is a group, formula 6a, wherein R a is an atom. hydrogen, fluorine, chlorine or bromine, alkyl radical with Q 1-3 "carbon atoms, 'group 30, pentitro,' methoxy Qi ~ a or trifluoroethylene, R. , 'chlorine or bromine, m'ethoxy or alkyl group of 1-3 carbon atoms, or R1 surrounds the group of formula 7 where Ylm Q is sulfur, and and Re is 3.5 - a hydrogen atom; and a group of compounds of formula 1 is oxygen or sulfur. Another group of compounds of formula 1 is based on compounds in which R is a group of formula 4 or 5, In the formulas X stands for ethylene radical, 40 for trifluoromethyl radical, or CH and OCH 2 - and Z stands for methyl or methoxy radical, R 1 represents the group of formula 6, where R a and R ~ however, there are different or different types of hydrogen, fluorine, chlorine, bromine and io atoms, alkyl and alkoxy radicals, 9 1-4 carbon atoms, nitro, trifluoromethyl groups; cyano or CHaS / O / n - 'or CH a CH 2 S / O / n, where .. are the formula, ah n denotes the number of zeros' ~, 1 or 2, R 4 'represents hydrogen, -fluorine,' chlorine, bromine or rhodium, and m'-ethyl, 'represents hydrogen,' fluorine,. , chlorine either. bromine or a methylol radical, or bromine or a methyl or methoxy radical, and R 7 stands for a hydrogen, fluorine, chlorine-or bromine atom, or an alkyl radical or an alkoxy radical with 1-2 carbon atoms, where when R s is , a substituent that is not a hydrogen atom, then at least one of R a, R (, Re and R 7 are other than hydrogen and, at least 2 of the sub-group: and k6w R a, R. (, Re iR 7 must denote the hydrogen atoms and when RI) denotes a volume of hydrogen. And. All the bases R a, R 4, RCJ and R 7 must denote chlorine atoms rub methyl radicals and! when both ': the -R a and R 7 substituents attach a hydrogen atom, then at least one of the sub-, 65 4: R 4, R s a, Either Re must be a hydrogen atom, or R 1 in formula I is a group of formula 7, where Q 'is oxygen or sulfur and R is hydrogen, rhodium, k' methyl or chlorine or bromine, or R 1 is a group of formula 8 or 9, where m in formula 8, R g and R 10 sa identical or different i. denote a hydrogen atom, chlorine radicals, and not chlorine or bromine radicals, "or when R is a group of formula 4 'or 5, in which <; l1 "ach X stands for hydrogen, chlorine or bromine atom, methyl ~ alkoxy group with 1 -: - 3 carbon atoms or methylthio and Z is methyl or m, ethoxy radical, then R 1, means group o in formula 6, in the short form R a and R, e are the same or different and represent hydrogen, fluorine, chlorine, bromine and iodine atoms, rhodium, alkyl and alkolciyl groups with 1-4 carbon atoms, gr1uPY ', nitrole, triiiIuoromethyl , cyano or groups of the formula CHaS / Ol n or CH a CH 2 S / O / n - where 'n is zero, 1 or 2, R 4 is hydrogen, fluorine, chlorine, bromine allbo a methyl group, R salt of a fluorine, -hlorine or bromine atom or a methyl radical of a methoxy group, and R7 being a hydrogen, fluorine, chlorine or bromine atom or an alkyl or alkoxy radical of 1 -2 carbon atoms, 'with IC ~ [mu] O, at least one of the substituents, in Ra, R 4, Re and R 7, another number of hydrogen and at least 2 of the subjuncts' R a, R. (, Re and R 7 must Mark hydrogen atoms, o. And both bases The radicals R a and R 7 'stand for hydrogen atoms, then at least ...;. less "one of R 4 or Reuu & OlZ replacing a hydrogen volume, allx R 1 in formula 1, is' g ~ upe of formula W /, in which Q is sulfur and Re is a compound: methyl or chlorine. - Or, bromine, or R 1 stands for a group of formula 8 or 9, where the formula is 8 bases, the cells R g and R 10 are the same or different, and denote hydrogen atoms, methyl radicals, chlorine atoms of arms, and W in formula 1 denote oxygen or sulfur altom, where "W and Q may be bottom or different. Compounds of formula 1 may be present in the agent according to the invention in free or salt form - suitable for use in agriculture. Due to their activity and / or their costs, 1) compounds of formula 1 above are preferred, in which - R 1 represents the group of in the formula 6, especially 2) when in the formula 6 R a represents a hydrogen, fluorine, chlorine or bromine atom, or an alkyl or alkoxy radical with 1 ~ 4 carbon atoms, a CHaS group or a CH and CH 2 S-, RI group) stands for .hydrogen atom, fluoro, .chlorine. u b bromine either. a methyl radical and Re represents a hydrogen, fluorine, chlorine or bromine atom, and qb an alkyl or alkoxy radical with 1-4 carbon atoms, a trifluoromethyl, nitro group, a CHaS- or CH a CH 2 S- group, when R s is a substituent other than r and 1 - hydrogen, then R a, R 4, Re or -. R 7 independently of each other are hydrogen, fluorine, chlorine, or methyl or methoxy radicals. Especially 3) , interchangeable compounds 'in paragraph 2), if (a) R is a pyrimidinyl radical, X is a methyl or alkoxy radical,' having 1-3 carbon atoms and Z is;,. a methyl or methoxy radical, or (b ) R is a triazinyl radical, X is a methyl radical or a R 9 -alkoxy radical with 1-3 carbon atoms and. Z is a methoxy radical. 4) Of the compounds mentioned in paragraph 3), in particular those in which R 3 represents a total of hydrogen, fluorine, chlorine or bromine, an alkyl or alkoxy radical with 1-2 carbon atoms, the group with the formula CHaS- or CH 3 CH 2 S-, 'R 4, R s and R 7 are the same or different and represent hydrogen, fluorine, chlorine or rpetyl atoms and Re is a hydrogen, fluorine, chlorine or bromine atom, an alkyl or alkoxy radical with 1-2 'carbon atoms, trifluoromethyl group, nitro group or group of the formula CHaS-, or CH and CH 2 S-. 5) Equally preferred are those compounds mentioned in paragraph 3) in which R s, R 4, R s, Re and R 7 are identical or different and represent hydrogen, fluorine, chlorine. Or methyl radicals, in particular, those compounds in which R 3 is a fluorine atom, a chlorine atom or a methyl radical, and R 4, R s, R e and R 7 are the same or different. and represent fluorine or chlorine or methyl radicals, provided that when Rs is not hydrogen, then both R4 and Re must be hydrogen. 7) Particularly preferred are those compounds mentioned in paragraph 3, where R s 'represents a fluorine or chlorine atom or a methyl radical, R 4 and Re represent -hydrogen atoms,' and R s and R 7 are the same or different and represent hydrogen, fluorine or chlorine atoms or methyl radicals, or also 8) in which R is a hydrogen atom. fluorine, chlorine or chromium, an alkyl or alkoxy radical of ~ 1-4 atoms. carbon, group of formula, CHaS or · CH s CH 2 S-, all substituents R., R s and R 1 OZ: - have hydrogen atoms and R 6 represents an atom, hydrogen, fluorine, chlorine or bromine, alkyl radical or alkoxy with 1-4 carbon atoms, trifluoromethyl, nitro or CHaS- or CH and CH 2 S-. - 9) From the relationships listed in paragraph 8). especially those in which "R 3 is fluorine, bromine, or chlorine, an alkyl or alkoxy radical with 1-2 carbon atoms, and Re is hydrogen, fluorine, chlorine or bromine, ro ..." alkyl or alkoxy group with 1-2 carbon atoms, trifluoromethyl or nitro group, especially 10) those in which R a represents a fluorine atom, a chlorine or bromine atom, or a methyl or methoxyl radical, and Re represents a hydrogen, fluorine, chlorine or bromine atom or a methyl or methoxy 50 '.10'YY radical or a nitro group. Also valuable for their activity and or valuable are the compounds of formula I in which Hl o ~ is 1 or 8 and R is a pyrimidinyl radical, Q in formula 7 is a sulfur atom, X in formula 4 is a methyl radical or an alkoxy radical with 1-3 carbon atoms .. and Z is a methyl radical or methoxy or R is a group of formula 5, in which X is a methyl radical or an alkoxy radical of 1-8 60 carbon atoms and Z is methoxy and Q in formula 7 is sulfur, or R1 "is gr-pe, of formula 7, wherein Q is sulfur. and R a is hydrogen. In view of the activity, the compounds of formula I are valuable, in which 'R 1 stands for the group of formula 9 and W stands for the' ilene atom '. ~ due to their very high activity and low production costs, or both, the following compounds are: 1) N - [/ 4-methoxy-6-methylpyrimidinyl-21-amino carbonyl] -2- <;. chlorobenzenesulfonamide, m.p. 194-196 ° C ', 2) N - [(4,6-dimethoxypyrimidinyl-2) -amino; carbonyl] i2,5-dichlorobenzenesulfonamide, m.p. 189-190 o C, 3) N - [(4-methoxy-6-methylpyrimidinyl-21-amino k-rbonyl] -2-methylbenzenesulfonamide, m.p. 172-17 ° C, 4) N [14,6-dimethylpyrimidinyl-2 [beta] -aminocarbonyl] -2-thiophenesulfonamide, m.p., 224-228 ° C. 5) N - [(4-methoxy: 6-methyl-1,3,5-triazinyl-21-amino-carbonyl] -2-chlorobenzenesulfonamide, melting point 174-178 ° C, 6) N [/ 4,6-dimethoxy-1,3,5- "triazinyl-2H-aminocarbonyl] -2-chlorobenzenesulfonamide, mp 199-189 ° C and 7) N- [(4,6-dimethoxy-1,3) , 5-triazinyl / aminocarbonyl-2,5-dimethoxybenzenesulfonamide with a melting point of 187-188 ° C. While all bunches of formula 1 have herbicidal properties, not all of them work exclusively in the cultivation of various plants but · by selecting the appropriate compounds, weed control can be achieved without harming the crop being cultivated.For example, some compounds are particularly herbicidal in wheat and rice crops, they control chiaroscuro in corn, cotton, and soybean crops. or rice and fight riffle and water hyacinth ~ In addition, compounds (formula 1 are useful centerpieces and re ...: gulujacymi plant growth, lalp. increase the content of sugar in the cane sugar and sorghum and inhibit the formation of sleepy lobes in grasses such as Bahia.A. The following compounds are particularly preferred for the selective control of wheat weeds: N- [14-methoxy-6-methylpyrimidinyl-2 / -aminocarbcnyl-2-chloro-5-methoxybenzenesulfonarriide with a melting point of 199-20 ° C, N- [4-methoxy-6-methylpyrimidy, niio-21-aminocar, bonyl-2-chloro-5-methoxybenzenesulfonamide, mp 199-200 ° C, N - [/ 4,6-dimethoxy-1,3, 5-.triazinyl-2 / -aminocarbonyl] -2-chlorobenzenesulfonamide, m.p. 188-1890C and N- [(4,6-dimethoxy-1,3,5-triazinyl- (2-aminocarbonyl] -2), 5-dimethoxybenzenesulfonamide, mp 187-188 ° CB D9 for the selective control of tibia in crops, the following compounds are particularly suitable: N- [/ 4,6-dimethoxypyrimidine, 10-21-aminocarbonyl, l-2, 5-dichlorobenzenesulfonamide with a melting point of 189 ~ 190 ° C and N- [I4; 6-dimethiopyrimidines10-2 /: "" aminocarbonyl] -2,6-dichlorobenzenesulfonamide with a melting point of 194-196 ° C. - C. The following compounds are suitable for fighting natural water knotweed: 114069 7 N - [/ 4-methoxy- 6-methylpyrimidinyl-21-aminocar bonyl] -2-chlorobenzenesulfonamide, m.p. 194-196 ° C, N - [(4-methoxy-6-methyl-1,3,5-triaz.ynyl-2H-amino carbonyl] -2-chlorobenzenesulfonamide with a melting point of ----- 5 F74-178 ° C, IN- [(4,6-dimethoxy-1,3J5-triazinyl-2 / -amino-carbonyl] -benzenesulfonampd with melting point - 183-185 ° C and .N - [(4-methoxy-6-inethyl-1,3,5-triazinyl-21-amino-carbonyl-2-chloro-5-methylbenzenesulfonamide, mp. 175 ... ., .... ~ 76 ° C..D. Compounds have the ability to regulate plant growth: .. _N- [I4,6-dimethyl opyrimidinyl-21-aminocarbony-15 10] -benzenesulfonamide - m.p. 228-230 ° C, '.N - [/ 4,6-dimethoxypyrimidinyl-2 / -aminocarbony-. 10] -2,5-dichlorobenzenesulfonamide with melting point 189-190 o C, o N - [(4,6-dimethoxy-1,3,5-triazinyl-2 H -aminocarbonyl] -benzenesulfonamide - melting point 183-185 0 C, N - [(4-methoxy-6-methyl-1,3,5-triazinyl-21-aminocarboyl] -benzenesulfonamide, N - [[[beta] -dimethyl-1,3,5- triazinyl-21-aminocarbonyl] -benzenesulfonamide, m.p. 200-20l o C i '\ N- [14-methoxy-6-methyl-'1,3,5: "triazinyl-2H-mino carbonyl] - 2-chlorobenzenesulfonamide, m.p. 174-178 ° C. . \ E. Examples of compounds suitable for weed control in rice cultivation are: eN: "[/ 4-methylpyrimidinyl-2 / -aminocarbony10] -2-chlorobenzenesulfonamide with a melting point of 201-203 ° C i. N- [/ 4,6-dimethoxypi Yymidines 10-21-aminocarbons 10] -2,5-dibromobene enesulfonamide, melting point 102-204 ° C. N - [/ 4,6-dimethoxy-1,3,5-triazine-10-21-aminocarbonyl] -benzene.sulfonamide melting at 183-185 ° C. As shown in Scheme 1, compounds of formula ~ 1 45 can be produced by 'reactions' corresponding to 2. -aminopyr-pyrrolidines or 2-amino: "1,3,5-t-iazines of formula 3, wherein R is as defined above, with an appropriately substituted isocyanate or isocyanate of formula 2, wherein R 1 and W 50 are as defined above These reactions are most preferably carried out in obo: "" riieprotonic, riieprotonic. organic solvents such as methylene chloride-tetrafuran or acetohitrile at room temperature and atmospheric pressure. The method of adding the reaction components is not critical, but it is preferable to add the compound of formula 2 while stirring to the suspension of the compound of formula 3. Since the compounds of formula 80 are usually liquid in consistency, therefore their addition can be adjusted for years. The reaction is · predominantly exothermic and sometimes the "product set" is insoluble in the warmer roieszahi: non-reactive and crystallizes pure from it. 85 II. Solvent products are isolated by evaporation of the thinner, dilution of the solid residue with solvents such as chlorobutane or ethyl ether, and drainage. In some cases, it is possible to obtain an isomeric product by the reaction shown in Scheme 1. These isomeric products result from the addition of a compound of formula 2 to endocyclic ammonium nitrogen atoms of formula 3. The compounds produced by this addition probably have a structure corresponding to formulas 10, 11 or 12. where W is "oxygen," can be prepared by reacting the corresponding sulfonamides - with phosgene in the form of n-butyl isocyanate under reflux in a solvent such as chlorobenzene according to method: 8; . Ulrich and A.A.Y. Sayigh in Newer Methods of Pre-. parative OrganicChemisty, Vol. VI, p. 223 "" "':" 241, ed. Academic Press, New York and London, v. Foerst. If the yield of the desired sulfonyl isocyanate is at Using this low method, then the sulfonylurea, prepared by reacting butylisocyanate with the appropriate sulfonamide, can be reacted with phosgene as described in the referenced publication. The production of ulphonamides from mono and sulfonylchloride hydroxides is widely described in the literature, pp. by CroS'sley et al., J.An.Chem.Co-pp. 60, 2223 (1938). The preparation of 2-furansulfonamide is described in 'J.Org.Chem. 18. 894 (1953). Certain sulfonyl chlorides are most preferably prepared by chlorosulfonation of substituted benzene, naphthalene or thiophene to carbon tetrachloride, method H.T. Crarka et al. Org.Synth.Coll. Vol 1, Issue 2, (1941) p. 85. Other Chloride "! ben" :. zenesulfonyl, more preferably, is produced by d: vaporization of the appropriate aniline with sodium nitrite in hydrochloric acid, and then reaction of the dithiazonium salt with sulfur dioxide and chloride: cuprous m in acid acetic acid, according to the method of HL Yale F. Sowinski, J. Drog. · Chem. 25, 1824 (1960). Furansulfonylchlorides are most commonly prepared according to the formula 2. In 1) chemac, it is the butylol radical, and Et () is the ethyl radical. Sulfonylisothiocyanates can be produced by acting on -sulfonamides with sodium disulfide and hydroxide with potassium hydroxide, followed by the formation of a dipotassium salt with iosg'en, according to K. Hartke, Ar'ch, Pharm. 299, 174 (1966). Synthesis of heterocyclic derivatives cumulative amines are discussed in The Chemisty of Heterocyclic Com .. pounds, Inter-science Publ., New York and Lpnd, and in Volume XVI, The Pyr.iJInidiens, DJ Brown describes 2-amino-pyrimidines. . Suitable for agricultural use, the salts of the compounds of formula 1 are also useful herbicides and can be made with a lyophilic, known manner. For example, metal salts can be prepared "by treating with formula 1 with a solution. of the alkali metal IUQ of the alkaline earth metal salts of sufficiently 114.069 35 25 30 15 10 which drains r, zy'many wasp ~. Product washed with 1-chlorobutane. The tQIPIllie at a temperature of 228-230 ° C and in the infrared spectrum shows the characteristics of the 1cme spectrum at 1710, 1620 and 1550, cm-1. This product is N - [(4,6-dimethyl'O'-pyrimidinyl-2 / -, aminocarbonyl] -benzenesulfonamide. D. Class II. N- [14-methoxJsy-6 ... metyIQlPyrimidinyl'-2 / -aminocarbOInyl] -2-chlororobenzeneOiSulfone Ig mid. For a suspension of 280 g of 2-am, ino-4-metho-sy-6-methylpyrimidine In 2000 ml of methylene chloride, 43.4 g of 2-chlorobenzene sulfonyl isocyanate are added, stirring for 16 hours, cool to 10 ° C, and filter, obtaining 470 g of solid prOd, U1ktu, melting at 195 -l96 ° C ~ The mass spectrum of the product shows that its molecular weight is 356.Anal, and ~ 'Calculated' for the formula C 18 H 1a CINO "S..Calculated: 43 , 89% C, 3.40 '(0H, 15.75 °). N Found: 43.47% C, 3.5f3G / o H, 15.30% N: The product is N- / 4-Met'o \ xy-6-methylpyrimidylly-2 / -aminocarbonyl] -2-chlorobenzenesulf'o: "nam! Id. After a partial evaporation of the plI, it drops out 20 g of the by-product with a melting point of 16o-162 ° C, the absorption spectrum of which in red-red is similar to the spectrum of the main product and which the molecular egotisar is 356. Analysis. Obli'C · zo ~ 'O: for the formula C 1a H lI OiN04, O "S Obli <: rono: "43.89% C, 3.40% H, 15.75% N-lesion: 44.09% C, 3.56% H, 14.9" / 0 N. Stosuja.c an equivalent amount of the corresponding 2-a'mi nopyrimidine and the suitably hyped-benzenesiphonyl isocyanate following the procedure described in example I or II, Q the compounds listed in Tables la, lB, IC, lD and IE are maintained. 20 "9 orchard an, i'ol1.! E (e.g. hydroxide, alkoxide, carbonate or hydride). Similarly, it is possible to prepare quaternary amine salts. It can also be produced by exchanging one cation for another. Chwa ~ toi ', bad a'monium salt, with a solution containing a cation that is to be entered by a total exchange. This method is most effective when the obtained salt containing the given cation is insoluble in water. and it can be drained. The process of exchange 'the brain also conducts and by passing an aqueous solution of soybean Lia, z' formula 1, for example salt 'with metallium, calcium or quaternary ammonium salt' This way, a cation exchange is obtained and the desired product is eluted from the lumen through the column. It is preferable, when the given salt is soluble in water. Salts: the addition of compounds 10 in the p-toluene compound can be prepared by themselves by reacting the compound of the formula 1 with a suitable acid, e.g. p-tolu acid. enesulfonic acid, trifluoroacetic acid, etc. The invention is illustrated in the following examples, Ipirz where 'examples I ---- J {IV. they illustrate in: the hardness, the compounds of formula 1, examples XV-XLIV and the illus and the tests carried out with the agent are described, the composition of the agents: according to the invention, and then ... according to the invention. I-N - [/ 4,6..Idimethylpyrimidinyl -2 / -aminocarbonyl'ol ~ ben'zenesulfonam, id For an anhydrous mixture of 12.4 g of 2-amino-4,6-di-dimethyl'opiorimidine in 250 miles. · Chloil "towards the methylen, stirring strongly, drips into the temperature and under ambient pressure · 18.3 g of benzenesulfonyl isocyanate and mixes for 2 hours, after that. Compounds of formula 19" 'R a RI. R s Re Rt Melting point Oc ---.- L-- 1 2 3 4 5 6 H H H H H 228 ~ 230 F H H H H 218-219 CHa H H H H. 195-19 ~ CI H H H H ~ 204-205 H. ~ NO. H 193- ~ 96 H H H H H CF. H. 183 / d! H Cl H H H 142-143 -CF.H- H H H 218-220 NO. H H H H - CI H H -SOCH. H ".- CI HH - ~ OCsHl H - CHaO- R CHaO HH 198 ':" "' - 199 ~ IHH NO. H - CHa HH NO. H 191-192 CH. HH - cH / CH a /. H ~ 57-160 CH ~ HH "CI H ~ 09 ~ 211 CI HH CH. .H 211-213 F H H F H 18 ~ -190 -11 114 069 12 cont. table I-A l I 2 I 3 I 4 I 5 I 6 J H H CHa H - ClI 3 S- H \ H NO! H - CI-I 3. () - HH CHa H Ig3-194 CI HHH CHa 230-232 CI HHH CI 177-182 FHHHF 208-211 N0 2 H CI HH 210-212 CI CI CI HH 215 --'- 217 CI II CI CI H 204-205 -CH / CHg / 2 H CI -CH / CHg / 2 H: 131-136 I nC 4 H gO HH nC 4 H gO H - nC 4 H g HH nC 4 H g H - CN II H CN H - C 2 1I s S0 2 - .lI HHH - CH a S0 2 - HHHH - CHg- H CHa H CHa 227-231 / dl FHFHF 173-180 CI H CI H CI 208--210 · C .Ha °: - H CHaO- H CHa 192-193 CI CI H CI CI 120-222 CHa CHa H CHa C ~ a 244-246 CI CI HHH 195-197 CI CHa HHH 196-199 CH: JO- CI 'H i HH 179-180 F CI HHH J.96-197 CH a CI HHH 208-209 Br H Br H Br - CI H CI HH 202-205 FH CI HH 202-203 -SOCHa HHHH - H CI CI HH 210- 212 CI FHHH - H CI H CI H 199-202 FHH CHa H 210-212 Clf 3 HHF, H 200-201 · CI-IaO- H CI CHaO H 202-203 CI HH CHsO- '"H 198-199 Br HH Br H 211--212 - CHaO- HH CHsO- H 193-195 CHa HH CHa H 204-205 CHa HH Br H 205-207 C 2 H s O- HHC 2 H s O- 208-210 CH 3 O- HHF 199-201 CI HH CI 212-213 H Br HI - HHH CHgS- CHaS - - H - HHC 2 H s S0 2 - C 2 H s S0 2 - - CHgO HH CI CI CI 209-210 CH a CH 2 CH 2 O li H CH a CH 2 CH 2 O CH a CH 2 CH 2 O 150 -152 CHg CHg H N0 2 N0 2 221-223 T ab I ica IB Compounds of formula 20 R s R4, R s R o -------- l 2 3 4 - H ~ HHHIH CHg HH Br HHH Temperature R 7 melts ~ ia oC 5 6 H 204-205 H 149-151 H 210-21113 114 069 14 cd Table I-B 1 1 2 I 3 I 4 I 5 I 6 F H H H 1-1 198-199 CHg H H H H 172-174 CN H H H H - S02CHg H 1-1 H H 170-171 H H Er NO! H - H CI HH Il 151-153 CH 3 0 HHHH 178-180 HH 11 CFg H 150-152 HHF CN H - HHH -SO2CHg H - HH II -SO2C 2 HS II - CI CI Il HH 199-200 CI CHg Il IH II I 177-186 CHgO- CI II HH 190-193 CH 3 CI HH 1-1 190-192 F CI II HH 193-195 CI FHHH - CH 3 Br HH: ar - C 2 H s HHHC 2 H s - H CI H CI C 2 H s O- - H CI CI H II 193-195 nC 1 H gO HIH nC 4 H gO H 182-183 FH CI HH '206-208 JHHHIH - N0 2 H HH H 223-225 CFg HH .HH 194-197 CI HFHH 199-201 CI H CI HH 195-197 CI H CH 3 0 HH - HH CRgO NO 2 H 211-213 H CI H CI H 207-211 H CHa CHg HH / 193-196 C 2 H s S- HH N0 2 H - FHHFH 177-178 CHgO- HH CI H '199-200 CHg HH CI HI 206-207 C 2 H s O- H 1-1 C 2 H s O- H 175-- 177 I CHg CI H CI H 187-189 CR 3 OH CR 3 0 H lI 182-184 CI HH CHg II 197-200 CHg H Il N0 2 H 194-195 CHg HH -CH / CH 3/2 H 136-142 CI HH N0 2 11 178-180 CHg HH CHg H 174-176 CH_ ~ H II Br H 195-197 Br HH Br H 207-209 CH 3 O- HH CH 3 O- H 175-177 CI H fI CI IH 174 -179 FHH CHg H 207-208 C Hg HHFH 173-175 CI HH CHgO- H 199-200 C 2 H s H fI C 4 H g H - Ct! Hg HHC 2 H s H - CHgO- H 1-1 CHg H 180-182 FHHHF 192-195 CI HHH CI 148-153 CI HH fI CHg 166-170 C 2 H s SÓ 2 - II HHH; 200-202 CH 3 S- HHH II - C 2 H s O- HH CI IH 180-183 CI HH -SOCI-I 3 -15 114 069 16 cd Table IB I 1 I 2 I 3 I 4 I 5 I 6 CI HH -SOC 2 H s - CI CI CI HH 186-187 CI H CI CI H 189-190 CHa H CHa H CHa 203-205 FHFHF 197-199 CI H CI H CI 181-186 CHaO H CI CHaO H 173-175 CH a CH 2 CH 2 OHH CH a CH 2 CH 2 OH 173-175 CHaS H 'H CI H 215-216 CHaO- H CHaO- H CHaO 185- 187 CI CI H CI CI 215-218 CHa CHa H CHa CHa 223-226 CHa CI H CI H '181-183 CHa CI H N0 2 H 182-183 CHa CHa II N0 2 H 191-193 T ab I ica IC Compounds of formula 21 R a R 7 Temperature. R 4 R 6 Re melting Oc 1 2 3 4 5 6 HHHHH 202 ~ 203 FHHHH 200-201 CI HHHH 1791-181 CHa HHHH 184 ~ 186 S02C 2H s HHHH ~ HHH NO 2 H - H CI HHH 250 HHH CF a H 1901-191 CI HH CHaS- H - CI HHC 2 H s S- H - CHa CI HHH 183 ~ 184 F CI HHH 244h245 FH CI HH 223-224 CI HFHH 203t --- 205 CI H CI HH 1'9 ~ 191 -SOC 2H s HH NO! H - CHaO- H CHaO- HH 182 ~ 184 FHHHF 213 ~ 215 CI HHH CI 192r-194.NOs H CI HH 196r-198 CHaO HH CHa H 2.27t-229 CI HH CF a H 16H --- 162 FHHFH 210 : -212 \ Br HH Br H 201 ~ 204 CHaO- HH CHaO- H 198-199 CHa HH Br H 1701-172 CI HH NO! H .225L ..- 22S; CI HH CHaO- H 180 ~ 181 C a H 7 O- HHC a H 7 0 H 188 ~ 189 nC 4 H gO- HH nC 4 H gO- H 165-167 C 2 H s O- HHC 2 H s O- H 181 ~ 183 CHaO- HHFH 192 ~ 194 CHaO- HH CI H 197-198 CI HH CI H 18-9-190 CHa HH CI II 181 ~ 183 CI HH CHa H 216-217, CHa CI H CI H. 186- 18917 114 069 18 cont IC table 1 I 2 I 3 I 4 I 5 I 6 I CHa H lI N0 2 II 205f - 207 CHa HH -CH / CH s / 2 H 110-116 'CHa H II CHa II 187-189 CHaO- HHJH - CHaO- H CHsO- H II 173'-175 CI HHH II 1711-174 CHa H CHa H CIl s 197 ~ 198 FHFH CHs 219-221 '/ CH a / 2 CH HH / CH S / 2 CH F 16H-163 CI H CI HH 1 ~ 4-195 CHaS H If H CI 211--214 eHaO- H ClI s () - H lI 180 ~ -181 CI CI H CI CIIsO-. 2.23t ---- 224 NO! HHH CI 219-220 CHa CHa H CHa H 182, -184 CHaS HH CI CHs 211-213 CHaO HHHH 193 ~ 195 CHaO H CI CHsO H 141-143 CF a HH H_ H 219-220 CHaO CI H CI H 183-185 CHa CI II NO ~ II 207-209 IHH CHaO NO! II 210-212 CHa CHa H N0 2 II 225-227 T ab I ica ID Compounds of formula 22 R a R, IR s I R., R 7 X Top temperature: erua Oc l 2. · 1 3 I 4 5 6 7, HHHHHH 187-189 CHa HHHH -CH 2 OCH a 157-158 CI HH II H -CH 2 OCH s 179'-180 CI HH CI H -CH 2 OCH s 174-176 CHaO- HH CHaO- H -CH 2 OCH a 155-157 FHHHHH 192t - 193: CH s HHH II H 2111-213 CI HHHHH 20h-203 'H CI H, HHH 198i --- 199 F, CI HHHH 219-220' CHa CI HHHH 211 L 213 FH CI HHH 222-235 / d / H CI H CI HH 201t-203 CHaO- HH CI HH 224: -226 CI HH CI HH 207t -'- 20i9 CHa HH CI HH 217L-219 FHHFH fI 173'-199 CI H II H CI II 160-163 HHHHHC 2 H s O- 180-182 CI HH CI HC 2 H s O- - CH, HH CI HC 2 H s O- - CHs H ~ H CHa HC 2 H s O- - HHHHH / CH S / 2 CHO- 116r - 120 HHHHH CI 213-215 I CHa HHHH CI - H CI HH II CI 194-195 CI HH CI H CI --- CHa HH CI HC 2 H s - C ~ HH Clf a H CHa -19 114 069 20. continued tabUcy I-D ..... I 1 I 2 I 3 I 5 I 4 I 6 I 7 · H, C ~ a H H H Br; - CI H H. H 'It Br; - Cll HH, - CJ.H ~ Br - HHHHH .CHaS- 201B1d / CI H Il - HH 'CllaS- -, CHa HHHH CHaS .. · - CI HH CI H CHaS: .- CHa HH CHa H CIlaS · - lo --- 'HHHHH.-CF a 179-182 CH ~' HHHH -CF 13 17 ~ r - 174 C'l HHHH, -CF a 173-175 HH 'H -CF ~ H: -CF B 160-163 'CI HH CI H, -CF ~ - C ~ IHH CI H -C ~ a - I CHa HH' Cll a H. -CF) J '- NO! HH II H CI 17c ».- 172 Table IE Compounds of formula 23 R a I R4, IR and IR 6 IR 7 IXI ~ empe ~ atW" a topn; ienia Oc H ....., HHHHH 199-200 / d! H. HH · HH -CH 2 OCH a - CHe H · H Il H -CH 2 OCH a - HHHHH CI 181-183 CI HHHH; CI 185-188 - CHa HHHH CI 176-178 Cl H EJ CI H CI - CHa H · H CHa H: CI - HH, HHH CHaS- 194--196 CI HHHH CH ~ S- - CH, .HHHH CHaS- - CI "HH" CI H CHaS- - CHa HH CI H CHaS- - HHHHH -CF a 164-168 Cil HH 'HH -CF a 204-208 CH. H' HH Hi -CF 8 171-173 IHH 'H -CF. H -CF a 191-194 CI H II ~~ H' - CF a - CHa HH CHa H -CF s - H II H: HH 'C 2 H s O- 163 ---- 165 ~ I --II' HHHC 2 H 5 O- 142 --- 144 CHa H 1- 1 HHC 2 H s O- 148-149 CI H II CI HC 2 H s O- - CHa HH CHa HC 2 H s O- - Example III. N - [/ 4,6-dimethylpiximidinyl- -2 / -AmlinOkaTbonyl] -2-triophenesulfonamide 55 To 12 g of 2-amino-4,6-dimethylpyrimidine in 250 ml of Aryl acelonite is added by mixing 19 g of isocyanate 2-thiophene: sulf'o-yl and mixes in 'c: iagu 2h-dzin, then ó dlsa: C'za, it will open ~ see the given product of constant consistency, melting at ~ a-60 a-60 hour 215: -216 °, C. The infrared abnormal spectrum of the product shows peaks at 1540, 1605 and 1700 cmt / P r yk: l a d IV. N - [/ 4,6-ldv; umethylpyrimidine-65 10-2 / -aminocarboxyl] -2,5-dichloro-3-triophenesulphon.a.mid.ZW1ialZJe'k, this was --- s'Pos6b, that to a suspension of 12 g of 2-am, ino-4,6-dW'umetyI '~ irimidine in 300 ml of ethylene chloride, 26 g of 2.5 g of cyanate are added at room temperature. -dwurchl'o-3-trophenesulfonyl, stirred for 16 hours and the solution evaporated to dryness. The solid residue is rubbed with the diethyl ether of the sewer. The solid product melts ~ "temperature ~ from 192-194 ~ C and in the infrared, shows absorption peaks at 1550, 1605 and 1690 cm-t. 114 069 22 T ab I ica II-B Compounds of formula 25 Terhpera R 9 RiO XZ melting sequence Oc I CI CI ~ Ha CHaO- 186 ~ 188 CI CI CHaO- CHaO.. 201-202 CH 3 CHa CHa CHa ...- - CHa CH j CHa CH. # JO- - Br Br CHa CHa - CHa CI CHa CHa - I Br Br CH 'a CHaO- - - CHa CH ;; CllaO- ClfaO ·· - IHH CHa Cl-IaO- - 25 30 40 45 Szajac, 23.3 g of 1-naphthalensulfonyl isocyallate: mixed then within 14 hours and drain the desired solid product, which after washing a small amount of ethyl ether, is at a temperature of 177-178 ° C. Using an equilibrium, Z [la length of the corresponding 2-nopyr) 7lm'idine and iso ~ yjanate 1-m.aphthalenesulftOnyIu 1 by following the way in the example a'da ~ VI, the following siff is obtained 1: N- [I4-chlor-o-6-methyl10pyrim 1 idyl10-21-aminocarbonyl] -1-naphthalene sulfonamide with a melting point of 205-207 ° C, N- [I4.6 -dimethylpyrim , idinyl-2 / -am'inocCyl "bonyl] -1-naphthalenesulfonamide having a temperature of [I" with a mp of 201-202 ° C, I. N - [(4-methylpyrinidinyl-2) -. Aminocarbonyl-1-na phthalenesulfonamide with a melting point of ~ 182-35 · -183 ° C and N- [I4-methoxy-6-methylO! Piiry, mitidines10-21- bonyl] -1- aminoicar: phthalenesulfonamird-o. temperature: melting point 210-211 ° C. . ..P r z y] {l a d VII. N ~ [/ 4,6-dJ-dimethylpJirimidine 10-21 ~ aminothiocar botnetyl] -besenesulfone ', mid.For anhydrous suspension n ~ 12.4 g 2-am'ino-4.6 ~ two-methylp: 1rymiJdyJl1y. · in 60 ml of acetonitrile, 19.9 g of benzenesulionyl isothiocyanate are added, the resulting heavy precipitate is filtered off and washed with anhydrous ether. The obtained N - [(4,6-dimethylpyrimidin-2) -aminoiioiketomethyl] -benzene sulfonamide melts at the temperature of 167-17.0 ° C. Proceeding in a similar manner to that described in Example VII, and using equivalent amounts of 50 ' The corresponding sulfonyl thiocyanthate and the appropriately substituted amine pyrithimidine are obtained from 'Wiiaz' and given in the table, ch III-A, III-B and III-CP of example V'III. Iz'Ocyaniariy 2-furansulfony- T a b l i c a II-A Compounds of Formula 24 Tempera- R s Q X Z melting temperature Oc H S CHa CHaO- 207-208 H S. CHaO- CHaO- ~ 06-207 CI S CHa CHaO- 186--187 CI S CHa CHa 198-199 CI SH CHa 197--198 CHa S Clf a CHaO- - HS Gl CHaO- - HS nC a H 7 O CHaO- - HS Br CHaO- - HS CF a CHaO- - HS 'CHaS- CHaO ~ - HS CH30CH ~ r CHa - CI S CllaO- CHaO- - Br S CHaO- CHaO- - CHI S CHaO- CHaO- - Br S CHa CHaO- - I CI S. CHa CHa - HO CHaO- CHaO: ".- HO CHa CHa - Br S CHa CHa - CHa .S CH s CHa - HO CHa CH ~ O '185-188 21. Example V. N- [I4, - metolxy-6 ... methylpyrid. YI1Y 10-21-amin10carbonyl] -2-fUiranesulfonamide. To a solution of 2.10- g of 2-furanesulfonyl isocyanate in 40 ml of methylene chloride is added sd 1.60 g of 2-amino- 4-metho-oxy-6-methylpyrimidine, stirred at room temperature for 1 hour, and kept pulsating at room temperature under cl). .sz'czalnik under reduced pressure, em. Permanent residue is restored for a period of 1 day, under 10 z diethyl ether. · awi ~ paring weak: dy a'c'eton: i: trill and 'next - Desiccant and SUSCly, poisoning an acidic product which melts at 185-188 ° C with a formula. Using an equivalent amount of the appropriate 2-amino-pyrimidine and appropriately substituted isocyanate thiophenesium: Eonyl or furansulfolllyl and taping the method described in example 111-V gives the compounds given in tables II-A and II-B.P r z y class VI. N- [I4,6-diUl11ethoxypyrimid- ". 20 nyl-2 / -aminocarbonyl-1-naphthalenes1phonamide. To a suspension of 15.6 g of 2-a-nino-4,6-dimethoxy pyrimidine in 400 ml of acetonitrile, add T ab I ica III-A Compounds of formula 26 I. Temperature 1 Re R 7 XZ melting-o R a R 4 ia Oc 1 2 3 4 5 6 I 'l. A IIIHIHIHIHIH CHa CHaO- 188-189 HHHH : El CHaO CHaO- 192-193114 069 Z3 24 cd of table III-A 1 2 3 4 5 -. 6 7 8 CI HHHH CHa Clf a - C 2 H s S0 2 HH CH 8 S0 2 H CHa CH ~ O - CI II HHH CHa CHaO- 184-185 CI HHHH CHaO- CHaO- 169-172 CI II H CI H CHa CHa - CI HH CI H CHa CHaO- - CHa HHFH CHa CH ~ - CHa II HHH CHa CHaO. 165-167 j CHa HHH li CHaO- CHaO-, 181-182 CI HHH CI CHa CHaO- - CHaO- HH CHaO- ... H CHa CHa - CHaO- H II CHaO.- H CHa CHaO- 178-180 CHaO- II II CH a - H CHaO- CHaO- 191-193 CI H II CI H nC SH 7 CHaO- ~ CI H II N0 2 H CHs CHaO- - CI H II CF a H CH · aO- CHaO- ---., CI H II N0 2 H CHa CHa - CHaO- HH CI- H CHa CHsO- - CHaO- HH CI H CF a CHa - CI H CI HH CH 3 S- CHaO- -'- CI H CI HH CH s OCH 2 - CHaO- ---- j C 2 H s O- HHC 2 H 5 O- H CHaO- CHa ---. 0 \ CHa H CHa H CHsO CHa CHaO- - CHa H CHa H CHa CH 2 H s CHa - CHa H CHa H CHa CHaO- CHaO- - HHH CF a H CHa CHaO- - CHa FH NO! HH CHaO- - CHa FH N0 2 HH CHaO- - nC "Hg HH nC, Hg \ H CI CH 3 - 'nC, HgO- HH nC, HgO H Br' CHaO- ~ F CI CI HH CHsO- CHaO- - CHa HH CI F CHaO- CHaO ..- NO! H i, HH Br CHaO- CHaO- ~ CI HH CI H CHsO- CHaO- - J Cll a \ HJH CHaO- CHaO- - CF a HFHH CHaO- CHaO- - CN H CHaO- CN H CHaO- CHaO- - CHaS- HH CHaS- H CHaO- CHaO- - Table III-B Compounds of formula 27 Feb. Pro: ceses - described in this example follow the scheme 3.A. 2- fu ['ano'Lithium suimate.T abli ca III-C Compounds of formula 28 Rg IR 10 IXIZ CH 3 I CHa' CHa CHa CHa CEa CHa CHaO- J CH 3 CHa CHaO- CHaO- CLCI CHa CHa CI CI CHa CHaO - CI CI I CHaO- CHaO- HH CHa CHaO- Br CHa CHaO- 50 55 45 To a solution of 39.6 g (58.5 mlHmoles) of furan in 200 ml of anhydrous ethyl acetate is added, : in a nitrogen atmosphere and keep the temperature of the mixture at 3.0 ° C or lower, 400 ml of 1.6 m of n-butyl lithium solution in hexane and mix until it becomes sd, that the sediment temperature -25 to -30 ° C and, through the mixture, slowly pass over a 2-hour period of excess gas dioxide, sulfur, and, then mix I Temperature: a I zx melting CH CHa CHa - H CHa CHaO- 196-197 H CHaO- CHaO- 202-204 CI CHa CHa - CI CHa CHaO- - CI CHaO- CHaO- - CHa CHa CHa - CHa CHa CHaO- - CHa CHaO- CHaO- - Br CHa CHa - Br CHa CHaO- - Br CHaO- CHaO- -, I 114069 Table l c'a IV-A Compounds of formula 29 · Table IV..B Phases of formula 30 x I ~. Z ~ Melting point Oc CHa CHa 200 ~ 201 CHaa CHaO ~ 183-185 CHaO. CHa 166-171 CI CHaa - C! H 5 CHaQ. - CHaOCH. CHaO -, CHaCH! CH1O. CHaO 121-124 ICHa /! CHO 'CHaO - CHaS CHaa 197-199 ICHa / iCHO CHa - CHaS CHa - CHaCH! O CHa', - H CH, O - ~ .- CF a CHaO - "I Br Cl; Ia O -: Tempera- Ra X - Melting point Oc 2., '1 3 4 -: CHa ClI; - CHa "168---.:162 ... CHa CHaO CHaO i4 ~ 147 CHa CHaOCH 1 CH, 1 ~ 7-150 CHa ICH a / 2 CHD CHaO - CHa CH a CH 2 CH! O CHaO - 'CHa CHaS CHaO 191 ~ 193 CI CH,, CH,: ~ \' 26 August dry. Stal'a, the 'residue of rOilJC' is rubbed with ethyl ether and acrylics. Otr, the contaminated N - [/ 4,6-dimethyl-1 / 3,5-triazinyl-2 / -aminocarbo-nyl / -2-chlorobenzenesulfonam: id that melts in the p-ratUlra 115-118 ° C and its in · idm'O · mag: of the net nuclear resonance ~) 'in the. acid tr6jfluoro · oc towyin' show ~ single peaks at 2.6.9 and '2.9. parts per million ... P r z y'k l a d XI. N - [(4,6-c) wumethoxy-1,3,5-triaoyl-.2H-amino-carbonyl} -2- -hlorobenzene Q'Sulfonamide. To ~ 5.6 g of 2-atn'ino-4, 6-dimethoxy-1,3,5-trdazine, in 300 ml of neutral methylene chloride, inducing 0.1 g 1,4-diazarbicyltl ~ [2,2,2} octane, they are added, 'mixture .c, 21 .g of 2 "chlorobenzen-olsulf'Onyl isocyanate and a mixture of 16 hours, then sucked off the old product and washed it with '1-chlorobenane', yielding N- [ (4,6-di-dimethoxy-1,3,5-tr-α-zinylQ-2) -aminocarbonyl] -2-chloro "benzenesulfon-20 · mid mp 188-189 0 C. 'Product spectrum infrared and shows absorption balls at 1740, 1630 and 1595 cm -: - l, typical for te ~~ Zaju.zvvja ~ ku. using the method described in Examples IX-XI and simultaneously the amount of the appropriate am-inotrhiazine and the corresponding substituted isocyanate 'sulfony- 10 25 15 30 35 85 45 80 50 55 25 additionally for 90 minutes at room temperature , odaczy, wyracolIlY 2-f ~ anosulfiIl! ia: n li; tu. and wash, and it with a / cetone. P ~ oduct has a melting point of 250 ° C, IR (nujol) 3400 -:; - 3'000 cm ~ l, (W), 1700 ohm-l, 1500 cm-l, (VW), 1210 Jcm-l , 1140 cm-lr 111-5 cm-l, (M), 10 ~ 0 -cm- l (VS), 910.cm-l, 880 cm-l, 825, cm- l (W), 735 ~ - l (S). B. 2-furansulf'Onyl chloride. .90 Iml of water, 410 ml- glo HCl li .68., 0 g of lithium 2-furanesulflinate 'mix' and cool. to a temperature of 10 -: - 15 ° C, then 'within 30 minutes' 12, ~ ml (39.4 g) of liquid chlorine are added dropwise, and then stirring for a further 30 mm at this temperature. at 5 ° C, poured into 16 ° C and extracted with methylene chloride. After chlorine, methylene chloride is evaporated, 44 g of 2-furan: sulfonyl chloride are obtained, boiling point 95.9 ° C / 7 µm Eg. IR (pure) 340 (M) 3120, 1800, 1550 (M: :), 1450 '(S), 1380 (VS) and 1210, 1160, 1120 (VS) ,. 1035 (M), 1010 (VS), 913.882 Icm l - (S). C. 2-furanesulfonamide. 23 g (138 millipoly) of 2-furansulionyl chloride are added dropwise at 0 --- 50C to 2 ° C of steep NH 4 OH, stirred. In the 'C ~ algae of the night at room temperature, distilled the water under reduced pressure, dreaming, the sediment is rinsed with icy water and dried. 14 g of 2-furanesulfonamide, mp 120-122 ° C, IR (nujol) 3250, 3100, 1600 (W), 1550; 1310, 1190, .1140, 1120, 1055, 1005, 930, 880, 843 cm-1 (S). This compound has a melting point of 12 ° -122 ° C according to the publication JOC 18, 894 (1953). .D ~. 2-Furansulfonyl isocyanate. 150 ml of anhydrous toluene, 25 ml, oxa-Hlu chloride (295 mlilim'ol) and traces of diazabicY '~ lo [2; 2.2] octane (DABCO) are heated to dJo, temperature 90 ° C and in continuous 15 minutes add 10 g of 2-furanesulfonam idu. after. which in a liter mixture, it is dyed at 95 ° C for 2 hours, on (Stepn: it seeps and 00 pellets of different solvent under reduced pressure. It yields 2.1 g of oil as a product. the infrared spectrum (2280 cm-1) shows the 'absorbance c': t characteristic for iso ~ yjanria-: nu. from class IX. N - [/ 4,6-dimethyl-1,3,5 -triazinyl-2 / -amino-carbonyl] -! 2-methyl-obenz-lQsulfon "mid. Up to 12.3 g of 2-amino-4,6-drwumethyl-1,3,5-triazine in 250 ml b AcetOlIliJtryl can be mixed by mixing 19.7 g of 2-methylbenzenesulfonyl isocyanate at a speed that avoids excessive temperature rise of the reaction mixture. , which is desalted, washed with a small amount of diethyl ether d. SU! obtained. N - [/ 4.6 .. -doubled 1 tyl-l, 3.5-1n "azinyl () '- 2 / - am.inOlcarbonyl] -2-methylbenzenesulfonamide which melts at a temperature of 141-145 C. / For example X. N - [/ 4,6-diethyl-1,3 , 5-triazines, 10-2H-amino-carbonyl-10-] - 2-chlorobenzenos, lphonamide. Up to 12.3 g of 2-amino-4,6-divumethyl-1,3,5-triazine in 200 ml. a: cetonitrile is added by stirring 21.7 g of isocyanate table IV-B 28 cont. table ~ VC 1 I 2 I 3 l 4 CI CHaO CHa 174-178 CI CHaO CHaO 188-189 CI Cll a OCH 2 CHa 142-145 CI Cll a ClI 2 0 CHa 117-121 CI CH s CH 2 0 CHaO 132- 133 J CH ~ CHa - F CHaO CHa 168-172 F CHaO CHaO 169-175 CF a CHa CI-I a 172-174 CF a CHa CHaO 165-167 CF a CHaO CHaO 171-1 "13 N0 2 CHa CHaO 178- 181 N0 2 CllaO CHaO / decomposition / 175-178 CHa CHaS CHa - CHa- H CHa - CHa CH a CH 2 0 CHa - CHa / CH a / 2 CHO Cll a - CI HC ~ a - CI CHaS CHa - CI CI CHa - 13r CHa Clf a .....- Br CHa CHaO - Br CHaO CHaO - N0 2 CHa CHa 105-110 FH CH g - F CHaS CH. ') - IF CH a CH 2 0 CHa - F CH a CH 2 CHa 168-170 F · CH a / 2 CIIO CH s - CHaS CHaO CHa 181-184 F CH a CH a CH 2 0 CI-IaO - CH, O CHa CHa - C 2 H 6 S0 2 H CHa - CHaO CHaS CHa - CHaO CH a ClI 2 0 - CHa -. NC (HgO CI CHa - CHaO CHaO CHa - CHaO CHaO CHaO - C 2 H s CHa CHa - C 2 H s CHaO CHa - C 2 H s CHaO CHaO - nC 4 H 9 CHa CHa - ICH a / 2 CH CHa CHaO - / CH a / 2 CH lICsO CHaO - - nC a H 7 HCaO CHaO - CN lICaO CHaÓ - CHaS llCsO CHaO 171-174 T ablic 'a IV-C Zw Compounds of formula 31 Tempera- R 6 X Z melting temperature Oc 1 2 E 4 CI I CHa CHa 190-191 CI CHa 'CHaO - CI I CHaQ CHaO above 2 · 50. 5 10 15 20 25 30 35 40 45 50 55 60 85 1 I 2 I 3 oj 4 CF a .... CHa CHa I 158 "": "'- 162 CHa CHa CHa 184 distribution CHa CHa CHaO - CH:] CHaO CHaO J74 Irozklad / CHa H CHa - CHa CH a CH 2 0 CHa - CHa CH a CH 2 0 CHaO - CI CHaS CHaO - Br CHa CHa - 'Er CHaO .. CHa.- Br CHaO CHaO ----' N0 2 CHa CHa - N0 2 CHaO CHa - N0 2 CHaO CHaO - CF a CHaO CHaO ---- 'CF a CHaO CHa - CH a S0 2 CHaC? CHaO - CH a CH 2 S0 2 CHaO CHaO - J CHa CHa - F CHaO CHa - FC 2 H s O CHa - FC 2 H s O CHaO - F CHaS CHaO - F / CH a / 2 CHO CHaO - CI H CHa - Rr H CHaO - CHaO CHa CHa - CHaO CHaO CHa -.CHaO CHaO CHaO ---- j CHaO C 2 H s O CHa - CHaO C 2 H s O CHaO - CHaO / CH a / 2 CHO CHaO - nC 4 Hg OH CHaO ----., CHaO H CHa - CHa CHa CHa - C 2 H s CHaO CHa - CN H CHa - CHaS CHaO CHaO - C 2 H s CHaS CHab - nC 4 H g CHa CHa - .. / CH a / 2 CH CHa CHaO - / C'H a / 2 CH CHaO CHaO - nC a H 7 CHa CH ~ - Ta bIica IV-D Compounds of formula .32 Tempera Ra R 4 XZ melting rate Oc 1 2 3 4 5 CI I CI CHa I CHa 130-140 CI CI CHa CHaO 182- 184 CI CI CHaO c ~ 192-193 F CI CHa 'C a 171-175 F CI Cl {s CHaO 190-191 F CI CH 8 0 .CHaO' 275 CI CHa CHa CHa 188-189 CI CHa CHa CHaO 18729 114 069 30 3 cont Tables IV-D 4 5 T a b l i c a IV-E - ..Zviazki of formula 33 lu, the compounds given in the table are obtained: from 30 IV-A to IV-O.P r z y \ k l a d XII. N - [(4-methdk-6-methyl-1,3,5 triazinyl-2 H -am'inocarbonyl] -2-thiophenesulfonamide. For lys, iny 14 °, 0 'g 2-amino -4-meto \ xy-6-methyl- I- CI CHa CllaO CHaO I 148 --- 151 CHaO CI ClfaO CHaO. 178 CHaO CI CHa Clf 3 () CH a () CI CHa CHa - CHaO 'CI CHaS CI- IaO --- CHa .CI Clf a CHa _ .. • CHa CI CHaO CHa - CHa CI CHaO CHaO - CHa F CHa CHa \ - CHa F CHa Cl-IaO - CHa lt-, ClfaO CHaO - "'- .F CHa CHa -, CHa _0- F CHa CHa CHaO ~ - F CI-! S CHaÓ CHaO - .FF CHaS CHaO - CHa Cll a CHa CHaO - CHa CH:} CHa CHa (l- Ii! CI CHaO CHa. ' - FH CHaO CllaO --- FF CHaO CHaO- - FF CHaO Cll a -, FF CHa CHa r- CHa CHa CHaO CHaO ~ CH 3 0 CHa CHa CHa - CHaO F CHa CHa - CH a () F "CHaO CHaO - CHa Br CHaq CHaO - CI Br CHaO ClfaO - IC 2 H s / CI CHa CHaO J-- 10 15 20 25 I Tempera- Il a R s XZ round ~ delays Oc CI CI rH! LO CHaO 182- t90.CI CI CHa CI-IaO - CI CI CHa CHa - FF ". CHa (J CH a () - FF CHa CHaO _.- CI F Cll a, CH a () .- CI F Clf a Cll a O - - CHa F CI-I s CllaO., - CHa F CllaO ClfaO - F CI CHaO CHaO - F Br CHa CFlaO ._- CHa CI1: A .. 'Cll a CH 3 0 .. • .- CHa CHa CHaO CHaO - Cll a "CI, CHaO CHaO - ClIaO. CI CrI a CHaO _.CHaO CIlaO CHaa CHaO 218-219 CE "a F CH 3 CHaO - CF a y -: -, C" H 2 O- 'CHaO ..l "- N0 2 CI CH 1 () CHa 163 -164 ~ Table IV-F Compounds of formula 34 - R a R 8 XZ Melting point Oc 1 2 3 4 5 CI CI CHa CHa 190-192 I CI CI CHa CHaO 186-188 CI CI -CHaO CHaO 185 ~ 188 CI CI CH a CH 2 0 CHa 155-159 CI CI CH a CH 2 0 - CII.v C 147-149 Cll a CI-I a CHa CH;) - CI H CHaO CH s' - 110-112 s61 z CICOO - CI H CHaO CHa oil 's61 Cll a CHa / CH a CH 2 CH 2 CIijl'4-N + CHa CHaO 160-163 Cll a -CHa CHaO CHaO 169-173 CHaO CI CHa CHa - CHaa. CI') CH a - CHaO 174-179 CHaO CI CHaO CHaO / "165 CHaO CI CH a CH 2 0 CHa 183-183.5 CHaO F CHaO CHaa 201-203 F CI CHaO CHaO - F CI CHa CHaO - FF CHa CHa 164 -: 165 F ' F, CHa CHaO - ~., ..F - CHaO CHaO 206-208 CI F CHaO ... CHaO -31 114 069 32 cd of table IV-F I 2. i 3 I 4 I 5 1 Cl / ..F CHa CHa - CI CHaO CHa CHan 176 CI C ~ a () CHaO CI-IaO 201 CI CHaO CHa Cll a + - CI CF a CHa CHaO 177-178 CI CF a CHaO CIlaO · 165-167 CI N0 2 .CH a CI-I a 142 ---- 1144 CI. WELL! Cll a. CI - !. aO - CI NO! CllaO CllaO 168-174. ClI a ClfaO CHa '. Cl a - Cll a CI-IaO CHaO CHaO - CRgO 9 H a CHaO CHa - Cll a () CHa CHaO CI-IaO 210-213 CH a () CHa CHa CH ~ - CI CHa CHa CHa - CI CHa CHa Clf a - CI H CHaO CHaO oil salt / -Cll a / CH 2 / eI, N + CHaS CI CHa CH 8 0 95-100 CHaS CI CHaO CHaO 190-194 CI Cll a CHaO CHaO - F Cll a CHa CHa 180-182 F CHa CHa CHaO 185-186! ~., CHa CHaO CHaO 191-192 CH ~ JF CHa CHa 201-205 CHa "F CHa CH 3 0 - CEf ~ JF CHaO CHaO 183-184 l ~ CR: l / cH a / 2 C lJO CHaO - F CIlaO CHa CHa - F 'CHaO CHa CHaO - F' CHaO CHaO CHaO - Clf a CF a CHa CHa - Cll a CF a CHaO CHaO I - CHa. / CH a / 2 CH CHaO C.HaO - F CF't a Cll a CHaO - .... F CF a CHaO 'CHaO - CHa Br CIJaO CHal - CI Br CHa CHa - CHa CH a S0 2 CHaO CHaO - CHaO N0 2. CHaS CHaO - Br F CI CHa - CHaO / CH a / 2 CH Br CHaO - / CH a / 2 CH 'CHaO CHaS CHaO - F CHa H CHa - CHa N? 2 CHa CHaO 190-191 CHa N0 2 CHaO CHaO 142-145 CHa N0 2 CHa CIJ g - CHa / CH a / 2 CH CHa ClI,) 167 CHa N0 2 CHa CllaO 190-230 / decomposition / salt Na oil CHaO CHaO CHa CHaO / CHaCH2CH2CH2 / 4Na + salt / CH a / 2 CH / CH a / 2 CH CHaO CIfaO 123-128 CII ~ / CH a / 2 CH CHa CHaO 115 CHa / CH a / 2 CH CHaO ClfaO 135 CHaCH! O CI CHa C.HgO 179- 181 CH a Cl! 20 .CH a CH 2 0 CHa CHa 134-136 CH a CH 2 0 CH ~ CH2l) CHaO CHaO 187-188 CHa CI CHa CHa 189-191 CHa CI CHa CHaO - CH s CI CHaO CHaO - CI CHa CHa CHa --l .... CI CHa CHa CHaO -114 669 83 34 2 3 4 cd Tables IV-: F -5 ("l CHa I CHaO CllaO - Br Br CHa CI-la 204-205 Br ' Br ella CI-laD 178-180 I Br Br Clll) CI-I s () 1.75 CHaO CHsO ella Cll s 144-150 CHsO CHaO ClI ') CI-IaO 187-205 / decomposition / CHaO CHaO CllaO CI-laO 187- 188 CHaO CHaO CI-I a CH 2 O Cll s 96-100 CHaO CHaO CH 3 CH 2 O CllaO 138 ~ 141 CH a CH 2 0 I CI CII 3 0 I CHsO 174-] 7 ~ Table IV-G Compounds o Compounds of formula 38 T abl i. ca IV-K Compounds of formula ~: g, ZZ x. Table IV-L Compounds of formula 40 I Temperature R 4 R 5 XZ melting rate Oc, ------ CI CI CI CHa CH s 178-184 CI CI CI CHa CHaO 169-171 CI CI CI CHaO CH 3 0 175-178 I -._------ CI CI CI CH;) CH 3 - CI CI 'CI CH:} CHaO ---- I CI CI CI CI CHaO CH 3 0 - CI CH 3 CI CHa CHa - CHa CHa ~ O2 CHaO CHa 182-184 / rozkl.l CHa CI CH;} CHaO CHa - CHaO CI CHa 'CH 3 0 CHa - CHa CHa N0 2 CH;) CHa 196-197 3 4 1 CH 3 CH 3 CHa CHaO ~ H3 - "CI CI CI CHaO CH 3 0 - FFF CH: 10 CH ;; O -: CH 3 CI, CI CHaO CH 3. 176-178 CHa CI CH 3 CHaO CH 3 - CHa F CH 3 CHaO CH 3 - CH 3 CI CI CHa CHa 168-17fl I CHa CI CI CH 3 0 CH 3 0 173-175 30 20 2f 35 40 50 Table LV-H Compounds of formula 3e I '"Ternpera Ra R 7 XZ melting sequence Oc CI CI CHa CI-I a 142-158 CI CI "CHa CHaO 203-206 CI CI CHaO CHaO 205-208 CI Br CH a OCH 2 CHa - CI C 2 H 5 CHa 'CH a - CI CHa CHa CHaO 171-172 CI CHa CHaO CHaO 173-176 F {F CHa CHa 192-193 F ~ -, CHa CHaO 213-215 F; F CHaO CHaO 275 CI CRaO CHaO CHaO - j CI C 2 H s O CHsO CHsO - Tempe ra- I R, ~ R 8) X Z melting stage Oc CI I. CI I CHa CliJ 210-213 CI CI CHsO CHaO 207 CHa CHa CIIsO CHa - CHa CHa CHaQ CHsO - CHa .CH a CHa CH, - CHs CI CHa CH, - CHa CI CHaO CH, - CHa CI CHaO CHaO - CHa F CHaO CHaO _.- CHa F CH. CHaO -. CHa F, CHa CH.T a table IV-lVI Compounds of formula 41 T ab I ica IV-I Compounds of formula 37 Tempera- Rd R s XZ melting rate · C --- CI I CI Cll a CHs 194-195 CI CI CHa CHsO, 198-190 CI I CI CHaO CHaO 280 I NO! CHsO CHa CHsO 182-185 I 55 60 65 Tempera- Ha R 5 R 6 X Z. melting sequence Oc CI CI CI CH 3 CLfj 184-186 Cl CI CI CH 3 eH 3 0 169-171 CI CI CI CHilO CH 1 0 165-168 CI CHa CI CHaO ClI'3 - CI CH 3 N0 2 CH 3 0 CHa - F CH 3 CI CH ;; O "CHa - I CHaO CI 'CHsO CHaO CHaO 195 ... 35 Table IV-N, Compounds of formula 42 114 069 L- 36 This table VB Compounds of formula 45 Tempera - R 3 -R j RTXZ melting cycle oC I 'CHa CHa CH a CH 3 CHa 205-207 CHa CH3 CHa CHa CHaO' 17_7-186 CH 3 CHa. CHa CHaO CHaO lGO · -167 FFF CH:}, CHa 163-169 FFF CHa CHaO. L;) ~ - .., 153 FFF CHaO CHgO 194-196. CI CI ci CH; l CHa lQ8-190 CI CI CI CH;) CHaO 159 ~ 161 CI CI CI GHaO CHaO 158- 161 CI CI CHa CH 3 'CHaO - FF CHa CH 3 0 CHaO - CI CHa CHa CH 3 CHaO - CHa F CHa CHa CHaO - F CI CI CH 3 0 CHaO - FF CI CHaO CHaO -. 5 10 15 20 I Temper-a- Ha X Li Q melting point Oc - H CHa CHa S, 174-176 H CHa CHaO S 182-184 H CHaO CHaO S 191-192 CHa CHa CHaO S - CHa CHaO CHaO S - I CHa CH a CH 2 0 CHsO S - CI CHa CHa S 192-195 Br. " CHa CHaO S ~ CI CHaO CHaO S 193--195 H CH s CH 2 CHa S 132 ~ 138 'H CHa' CHaO O - H CHaS CHa S 223-22 ~) H CHaO CHaO O - 30 25 Table IV-O Compounds of formula 43 \ Tempe- "ratura R 3 -R 4 R a Rr XZ melting Oc I CHa CH 3 • CH 3 CHa CH 3 CH 3 200-205 CHa CH. CH 3 CH3 CH 3 CH 3 0 195- 197 CH 3 CHa CHa CHa CH 3 0 CHaO 185-189 CJ CI CI __ CI CH 3 CH 3 - I CI CI CI. CI CHa CH30 tl.87 above I CI CI CI CI CI CH 3 0 CH 3 0 250 IP at cl ad XIII. N - [/ 4,6-dimume, toxy-1,3,5-triazine} o-2 / -amino1carbonyl] -1-naphthalenesulfonamid. in the way that 16 g of 2-amino-4,6-dl-dimethoxy-1,3,5-m-aine in 400 ml of alcetonitrile are added dropwise to the suspension, 23.3 g of isocyanate and 1.ianium are mixed with the mixture. naphthal-nosulfonyl, then mixed for 14 hours and sucked off the product. Wash the product with ethyl ether at a temperature of 171-172 ° C. Proceed as follows. described in example XII] and using the equivalent amount, s'c., and the corresponding derivatives 35. nYJch a 1 mino-1,3, The compounds of the formula are given in Table VI. Table VI Compounds of formula 46 l-1,3,5-triazine in 300 ml of acetonitrile are added dropwise Si ~ 19 g of thiophene isocyanate. -2-sulf: -onyl, mixes for 6 hours and drains the precipitate, constituting the desired product, which melts at 182-184 ° C. Proceeding as described in example XI and using an equivalent amount; 'Wiedhich derivatives of am' ino :: '1,3,5-triazines and' isocyjaI: late. sulfonyl compounds are obtained from the compounds given in tables VA and VB. This table VA Compounds of formula 44 I and Tempera- Rg Rto. , X / Z melting cycle Oc CI CI I CHa CHa I 127-133, CI CI CHa CH ~ O 165-171 CI CI CHaa CHaO 181-184 CHa CHa CHa CHaO -. CHa CHe CHaa -CHaO - Br, I Br CHaa CHaa - I H H CH s'; CHaO -! 40 45 50 55. 60 65 x I z I Melting temperature Oc CHa CHa 179-183 CHa CfJa O 186-188 CHaa CHaO 171-172 CH a OCH 2 CHa -, P r z ykla d XIV. N - [/ 4,6-dimet · oxy-1,3,5-tr.ia .: zinyl-2 / -aminothioketomethyl] ... benzenesul: flonam ~ d.Zw, iaze'l ~ this is produced in this a method with a mixture of 20 g of benzene sulfonyl isothio'cyllian: 15.6 g of 2-amino-4,2-d1-dimethoxy-1,3,5-thifiazine, 250 ml of acetonitrile and a catalytic amount of d'Wula: The dibutyltin urinate is mixed for 24 hours, then the reacted triazines are sucked off and evaporated from the flow and a'cetonitrile1. P'ozostalosc, with the consistency of rubber, is rubbed with ethyl ether and drains the product. Its melting temperature. is 148-150 o C · .P 'by doing the same. described in example XIV and using the actual, different amounts of the corresponding iso-thiocyanates and llamas, inotriazines, otr, the compounds of the application are pronounced: in Tab. VII.114069 37 Table VII ~ bundles of formula 47 38 about 1-99, 9,9 / 0 by weight of permanent, thin, thin or. pink <;: ienclZalnilk6 \ w ..,. In Table VIII, the composition of, according to the invention, is given in terms of, tolerance, and their forms ... Means according to the invention may, depending on the prediction and physics, their total properties . of a given compound 'Formula 1 ZC1' has the number of this active syntax greater than the above-mentioned. Sometimes also 10 is desirable to know, the value of the active substance in the component. ' active, where such .prepaxats are obtained by introducing, the substances are absorbed into the agent according to the formula or by mixing 15 into a collection. 'Typical' diluent steels described in the publication Watkins and WSlp. Handbook of.lnse-cticileDust Diluents and Carriers, 2nd edition, Dorland Books, Celdwell, 'New Jersey. 6w, and lower the absorption power to the devices in the form of dust. 'TyrpQwe' c ~ ekle; 1 "" OZ oenials and solubilizers are described in Marden's Solvents Guide, 2nd Edition, 'Inter- 25 ·· science, New York, 1950. For the preparation of concentrated suspensions, no further information is provided. solubility lower than 0.1% • Concentrated solutions should not undergo phase separation at a temperature of 0 ° C. Substance; cjepoi Surface-active for: recommended and! Ch sto'So- ~ 30 wani: e given in pub1i! Ka 1 part lch: 'Me Cutcheon's Deterg, ents and Emulsifier, s Ann ~ al, Me Publi smng Corp., Ridgewood, New Jersej 'And Sisely and W-ood, EncYJ ~ iqpedia' of Surfa'ce Actdve Agents) Chem ~ cal Publistri.ng Co., Inc .., ~ ew York, 1964, 35 All Resources May Include. substances, inhibiting, agglomeration, agglomeration, deterioration, growth of microorganisms, etc .: These measures are produced by known methods. The solutions are usually prepared by mixing the ingredients:: 40 substances. The continuous formulations are prepared in-between. shredding, usually combined with hammer milling or hydraulic milling. The slurries are prepared by wet milling (see, e.g., US Patent No. 38,60084). Granules and 45 grams can be produced by spraying the active guide on. previously granulated carrier, or by agglomeration methods, e.g. described by J.E. Browning, Agglomeration, Chemical Engine ering, 4.12. 1967, pp. 147 et seq. and at Perry's 50. Chemical Engineer's Handbook, 4th Edition, Me Graw-Hill, New York, 1963, pp. 8-59 et seq. Other information on the production of agents of this type is contained, for example, in the following publications: Eat. Am. no. "'3235361,' 55 ~ column 6, ~ line 16 to line 17 in column 7 and in the examples 10 --- ': 41, description of St. Zje Am. patent no. ~ 309192, coluIl? -na 5, line 43 to line 62 in column 7 and in examples 8, 12, · 15, 41, 52, 53) 58, 132, 138-149, 162-164, col. '167 and 169-182, 6.0 US Pat. No. 2891855, column 3, line 66 to line 17, column 5 as above 58, 132, 138-i40, 162-164, k-01.167 and 16 ~ -182. TroI as a Science, John Wiley and Sons In · c., New York, -1961, pp. 81-96 and _ in JD Fryer 65 and SA Evans, Weed ~ or; Ltrol Handbook, ed- I, / I ... pattern 48 pattern 49 ~~ pattern 48 pattern '50 - pattern 51 pattern 50 - pattern 52 pattern 53 - pattern 54 pattern 53 - pattern 55 pattern 53 182-185 pattern. 52 pattern 56 - pattern 55 pattern 56 - pattern 51 pattern 49 142-144' pattern 67 pattern 56 - design 58 design 56 - design 59 design 53 - design 60 wz6r 53 - design 61 secondary 53 · .. - wz1Jr 62 I / design 53 188-190 Irpzkl.f design 63 design 50 - design 59 design 56 - design 60 design 56. - pattern: r 62 pattern 56 - pattern '61 pattern 56 - pattern 64 pattern r 56 - I formula 6 \ formula 53 - '"Content in% by weight" - Substance- -' Type of agent substances active chemical- Diluted surfaces wettable powders 20 -90 0 ---- 474 1-10 Oil suspensions, emulsions, solutions ~ as well as emulsifiable concentrates 3-50 40-95 0-15 Aqueous suspensions, 10-50 40-84 0-15 Granules and lumps 0.1-95 5-99.9 1 ---- 120 Pyly 1 -: - 25 70-99 0-5 Concentrated agents 90-99 0 ---, 10 '0-2 Table VIII Agents The inventive compound containing the compound of formula 1 is prepared by known methods. These agents may be in the form of dusts, granules, decomposers, solutions, suspensions, emulsions, wettable concentrates, etc. Many of them we can slto say or indirectly in these forms. The spray can be sprayed with appropriate substances and for the dusting of stacks: ~ c in volumes ranging from a few to a few kilosets of litlI "6 lions per 1 \ j} a. as starting products for the production of: the following preparations Generally speaking, the compositions according to the invention contain about 0.1-990/0 by weight of the active ingredient or ingredients and at least one surfactant in ~ losci 0.1-20 0 / tonne by weight i114 069 39 40 30 35 45 40 55 or preferably after dilution with oils or after emulsifying with water.cycla d XX. Wettable powder.N - [/ 4,6-dimethylpyrimidinyl -2H-amino-carbonyl] -2,6-dichlorobenzea.sulfonamide 20% sodium alkyl naphthalene sulfonate 4 ° / 8 sodium lignin sulfonate 4% low viscosity methylcellulose 3% attapulgite .. 69% The ingredients are carefully mixed and ground in a mill with a hammer to the particle size below 100 microns, then mixed again, sieved through a sieve with 0.3 mm holes and packaged. d XXI. High concentration granulate. 4- [14-methoxy-6-methylpyrimidinyl-2H-aminar. carbonyl] -2-methylbenzenesulfonamide 1% N, N-dimethyl-oformamide 9% granulated attapulgite (0.84 -: - 0.42 mm) - 90% The active ingredient is dissolved in a solvent and sprayed on the dust-free granules in a two-stage mixer. After spraying is complete, the mixer is kept running for a short time before packing the product. P r y k, l a d XXII. Solution in the form of an aqueous suspension. N- [14,6-ctimethylpyrimQynyl-2 / -amino-carbonyl] -benzenesulfonamide 40% polyacrylic acid thickener 0.3% polyethylene glycol dodecylphenol ether 0.5 0 / Cl disodium phosphate 1% phosphate monosodium 0.5% polyvinyl alcohol 1.0 8/0 water 56.7% The ingredients are mixed and ground in a mixer until the veneer mass is obtained so that particles with a diameter of less than 5 microns are obtained. Example XXIII. The agent is in the form of a solution. N - [/ 4-methoxy-6-methylpyrimidinyl-2 / -amino carbonyl] -2-chlorobenzenesulfonamide in the form of its sodium salt 50/0 water 95 0 / Cl The salt is dissolved in water, by stirring, the resulting solution is immediately ready for use.Pages d XXIV. The agent in the form of granules of low concentration. N - [(4,6-dimethylpyrimidinyl) -aminocarbonyl] -2,6-dichlorobenzenesulfuramide 0.1% granulated attapulgite (0.84-0.4 ~ mm) 99.90 / 0 The active ingredient is dissolved in a solvent and the solution is sprayed onto the dust-free granules in a two-cone mixer. After spraying is complete, the product is heated in order to evaporate the solvent, allowed to cool and pellet. Granular agent. N- [14,6-dimethoxypyrimidinyl-21-amino ~, carbonyl] -2,5-dichloro-benzenesulfonamide wetting agent crude lignosulfonate containing 5-20% 60-natural sugars 100/0 'attapulgite clay 9 ~ / 0. mixes and grinds to pass through a 149 micron sieve, then introduces it into the fluid bed granulator and regulates the air flow to the fluid, for example XVII. Granulated agent. Wettable powder of example XVI 5% granulated attapulgite 0, e4-42 mm 95%. he is packing. He is packing. XVIII. Center in the form of extruded granules. .N - [/ 4-methoxy-6 "': methylpyrimidinyl-2 / aminocarbonyl] -2.:. Chlorobenzenesulfonamide 25% anhydrous sodium sulfate 10% crude calcium lignin sulfonate 5% sodium alkyl naphthalene sulfonate 1 ~ / 0 calcium bentonite -magnesium 59% The ingredients are mixed, ground in a hammer mill, approximately 12% of water is added and the mixture is extruded in the form of cylinders with a diameter of 'approximately 3 mm. These combs are cut into lumps approximately 3 mm long. this can be used as is, or .50 is dried and crushed so that it passes through a sieve with 0.84 mm holes. Lumps retained on a sieve with a hole diameter of 0.42 mm are packed as a finished product, and the finer part is recycled for processing. Example XIX Preparation in the form of a slurry of oil N- [14; 6-dimethoxypyrimidine10-2H-amino carbonyl] -2,5-dichlorobenzenesulfonamide 25% poloxyethylene sucobite hexaoleate 5% oil with high content of aliphatic hydrocarbons ~ 70% The ingredients are ground in a sand mill until particles with a diameter of is approximately 5 microns. The resulting suspension may be used directly 5, Blackwell Scientigic, Publications, Oxford, L968, pp. 101-103. In the following examples, unless otherwise noted, percentages and parts are percentages and parts by weight. p r z y cla d XV. Wettable powder., N - [/ 4,6-dimethylpyrimidine10-2 / - 'aminocarbonylol-benzenesulfonamide 80% sodium alkyl naphthalene sulphoylate 2% sodium lignin sulphonate 2'O / ~ 10 synthetic amorphous silica; 3% kaolin 13% ingredients are mixed and grinds in a hammer mill until all the solids are reduced to a grain size of less than 50 microns, then mixed again. For example XVI. Wettable powder. N - [(4-methoxy-6-methylpyrimidinyl-2) amino carbonyl] -2-chlorb-5-methoxybenzenesulfonamide 50% 20 sodium alkyl naphthalenesulfonate 2%: methylcell ~ low leavening 2% earth · Diatomaceous 46%. The ingredients are mixed and pre-milled in a hammer mill and then ground in a pneumatic mill · 52 until essentially all particles are less than 10 microns in diameter. The product is remixed prior to packing-114 069 41 42 25% 10% / 5% 1% 59% - below 50 microns, followed by additional mixing and packaging. Wettable powder N - [(4,6-dimethyl-1,3,5-triazines ~ 0-2) -aminocarbop.yl] benzenesulfonamide 50% sodium alkyl naphthalenesulfonate 2% methylcellulose low viscosity 2% Diatomaceous earth 46%. The ingredients are mixed, first in a hammer mill and then in a pneumatic mill, so as to obtain particles with a diameter of less than 10 microns. The product is mixed additionally before packing. p r z y cla d .XXXII. Aggregate in the form of granules. Wettable powder of example XXXI 5% granular emulsion stage (0.84-0.42 mm) 95% A wettable powder suspension containing about 25% solids is sprayed onto the surface of the granular emulsion stage in a two-cone mixer ~ u, then dried and packed. Order XXXIII. Oxygenated N - [(4-methoxy..6-methyl-1,3,5-triazinyl-2) - agent. aminocarbonyl] -2;., chlorobenzenesulfonamide anhydrous sodium sulfate crude calcium ligninsulfonate alkylnaphthalenesulfonate sodium calcium-magnesium bentonite. It joins in the form of cylinders with a diameter of about 3 mm and cuts, obtaining lumps with a length of about 3 mm. This product can be used immediately after drying or it can be crushed to pass through a screen with 0.84 mm openings. The lumps retained on a sieve with 0.42 mm holes can be packed, and the more expensive parts can be returned to the process. Oily suspension agent. N- [14,6-dimethoxy-1,3,5-triazinyl-2H-amino-carb'onyl] -: 2-chloro-5-methoxybenzenesulfonamide 25 0 h polyoxyethylene sorbitan hexaoleate . 5% oil with a high content of aliphatic hydrocarbons 70% 'The ingredients are ground in a mixer. To produce a molding mass until obtaining solid particles with a diameter of less than about 5 microns and the resulting suspension can be used directly. or after dilution with oils or emulsification with water. XXXV. The agent in the form of a wettable powder N - [1,4,6-dimethoxy-1,3,5-triazinyl- (2-alnincarbonyl] -2-chlorobenzenesulfonamide 200/0-alkyl naphthalene sulfonate sodium 4% sodium lignin phonate 4 ° /, .. 'low viscosity methylcellulose 3% attapulgite .69% The ingredients are thoroughly mixed and ground in a non-hammer mill, producing solid particles less than 100 microns in diameter, then mixed 20 55 60 65 • 80% 2,% 2% 3% 13% and grinds solid particles in the mill. about the size gently the material. A thin stream of tubing is directed to the fluidized material until the granules of a given size are obtained. The flow of water is then stopped, but the fluids continue to flow, possibly adding heat. until the water content is reduced to the desired number of bones, usually smaller rivets. 1%. The resulting product is generally screened through a 1410 ~ 149 micron sieve and packaged. ~ r z ykla d XXVI. High concentration concentrate. .N - [(4,6-dimethylpyrimidinyl-2) -amino-carbonyl] -2-thiophenesulfonamide 990/0 silica derogel 0.5 ° /, synthetic amorphous silica 0.5% 15 The ingredients are mixed and ground in a hammer mill so as to obtain the essential product ~ completely passing through a sieve with 0.3 mm apertures. This concentrate can be diluted if necessary, c. p r z e cla d XXVII. Agent in the form of a wetted powder. .N - [&lt; 4-methoxy-6-methylpyrimidinyl / amino-carbon [gamma] -1-] -2-chlorobenzenesulfonamide. 950/0 "dioctylsodium sulfosuccinate 0.1% synthetic, decomposition, reduced silica 4.90 / 0. The ingredients are mixed and ground in a hammer mill to obtain substantially all particles less than 100 microns in diameter, then sieved through a sieve with 0.3 mm holes and packs it. 30 Example XXVIII. The agent in the form of a wetted powder. N - [/ 4,6-dimethoxypyrimidinyl-2 / -aminocarbonyl] -2,5-dichlorobenzenesulfonamide 400 / 0 20% sodium lignin sulphonate. 35 Montmorillonite clay 400/0 Composed and mixed thoroughly, ground first in a hammer mill and then in a pneumatic mill, producing particles substantially less than 10 microns. The product is mixed an additional 40% and Packing. For example XXIX. Srdek in the form of an oil suspension. N - [(4-methoxy-6-methylpyrimidinyl-2 1 H-amino carbonyl] -2-methylbenzenesulfonamide 35% 45 mixture of carboxylic acid esters of polyhydric alcohols with oil-soluble petroleum sulfonates 60/0 - ~ xylene 59 % 50 The ingredients are mixed and ground in a molding pulper so as to obtain substantially all particles with a diameter below. 5 microns The product can be used as is or diluted with oils or emulsified in water. Product in the form of a wettable powder. j N- [(4,6-dimethoxy-1,3,5-triazinyl-2) -aminocarbonyl] -benzenesulfonamide alkyl naphthalene sulfonate sodium ligllin sulfonate synthetic amorphous silica kaolin The ingredients are mixed by suction until 114.069 was obtained. 44: Sift twice through a sieve with 0.3 mm holes. The ingredients are mixed and ground so that they can be stored ~ -. -. and 'PJlkuje. . . '- they were working through a sieve with holes 149 microns i., introduction '.p lo' z y k l · a d, XXXVI. Sradek in the form of a suspension to the granulator with a fluidized bed .. Do- .'- 8 1 l1Y w .., qle · ju.,, Flow,, regulates air. sk: so that · lag9nie .. f1u- .N - [/ 4; 6 ~ dimethox'y-1,3,5-tria! ynyl-2 / - 5. follow the material and on this material he introduces · ~ inokarbOnYlo] ~ beI.lzerios \ llf ~~~ mid ~ '. as "." a thin stream of water. The process of fiuidization was introduced into the "carcass", ",", and to obtain granules o '! -.: polyalcohol rZ 'soluble in "p ~ o-" oil. .fi 'bones, pq stops., water supply and' wheels! lty'- ". rlukt.ami · sulf, on oil fraction 6" "_, hums" fluidization,. possibly with heating, az '·. xylene, "".. '/' S ~ ,. 10 to reduce the content of the ode, usually to less ~,. The ingredients are 'mixed' and ground in a bowl 'to less than 1 "0.' The product is sifted through a sieve, usually 'molding', until a 'time-t' is obtained with holes of 141 ~ 149 'microns, and' packed 'into' 'uiyt- "orchard", below . 3 micron ~~. The product of the moina 'cone ..'. ''. - -: '_, ~ word direct ~ io l ~ b dilution; zonl!' oils- or. Example XLII. , Granular agent and masticated in water ~,. 15th concentration. ' ",, P.'Cla d, XXXvIII., Agent in the form of con-, N - [) 4-metaxy-6-methyl-I, 3,5-triazinyl-.2I-., A .d ~ zYm centrate 'concentration'1' ..aminocarbonyl] -2-chlorobenzenesUlphonamide 0.1 ". N: = - [14,6-dimethoxy ~ 1,3, ~ -triazinyl-2 / ~ - - granule ;; lpulgite (0.84-0.42 min), 99.9 ", '~ amiD'carbonyio] -bentenesulfonate 99", The active ingredient dissolves in W. solvent-' laryngeal aefol, 0.5 ". 10 ~ ikti and the solution is sprayed on the dust-free granulate a-la-- '~ y ~ thetycin. amorphous silica' O, S- ,. pulgite vr 'two-sided ~ mixer. After' zakon- '., ingredients, you cut and grind in Before using the atomization hammer, it is heated in order to evaporate to obtain a product which flows through the solvent, to leave it to undercooling and to 'through the sieve 9' of the Q formers, 3 mm. Concentrate, this one packs .. to be prepared additionally. 25. / P · r Zlykla d X'LIII. XXXVlP. "Sradek ~ granulated" powder. Low concentration. N - [/ 4-methoxy-6-methyl-1,3,5-tri.azinyl-21-N ": r / ~ -; methoxY-6- methyl-1,3,5-kiazinyl ~ 2 /: "aminQcarbonYlol-2: cllloro-5-meth-xYbenzene-,.-aminocarbonyl] -2-chloro" ': 5-methoXybenzene' sulfonamide, 95 1 /, "sulfonamide :. '1 "0 '30 dioctyl sodium stilphosuccinate'. O, l "at 'N, N ..; two ~ ethylformanlid g ~'. S)" ntetic, fragmented; niona ktzemi nka 4.9 "•. ~ Ariulated attapulgite - (0.84 ~ O, 42 mm) 90 "," Ingredients are mixed and ground in a mill with a hammer ~; 'Partial ingredient' dissolves' in '·, then releases) -' soak to an olefin 'size of particles of ~ .. nickel size' , i-ro ~ the formation of .spray, on .. dusted atap'-llgit in the downstream of ~ 100 n; lycrons, sieved through a sieve with a rotating opening of the 'mixer. After finishing the sprays 0'; 3 mm and packs... "o" mercury .. mixes and joints in a short part of the time, at the j 'he puts d ~ IV. The agent in the form of: wetted- ~ u and.steply packs the granular product. N - [(4-methoxy-6-methyl-1,3,5-triazinyl-2) - suspensions: \. 2-chlorobenzenesulfonamide 'aqueous agent. 40 ", I 'N - {(4,6-dimethYI ():. 1, ~, S-triazinyl-21- 40" sodium lignin sulfonate 20', ~ amine -carbonyl ... benzenesulfon ~ i ~ 40 "0 'Montmorillonite clay 40' /,, tag, eszczacz) made of polyacrylic 0; 3 ", 'S ~ ladniki' mixes exactly. ~ mly- ·, ether dode'cyIOf ~~ óI6 ~ y ':' g ~ ikQlu polyethylene; • non-hammer and then pulverized VI pneumatic- ", go .-,." "0.5 '/. - I am milling like this, to poison particles with a diameter of '~~,' disodium phosphate. '/' 1 '/,' '45' below 1.0. · Micron6w ~: Produkf mixes ~ b ~ extra- \ monosodium phosphate-,, o, S ", wo and '~ pak ~ je ~ I:.' polyicohOI; ", 1,0". Method and described in 'Examples' XV-r-XLIV 'water ~, J,', 56.7 ", you can make all the resources according to the invention. S ~ metrics. mixed - s ~ e and 'grinds' w. mixer ~ do lazku.- 'wYtwlU "~~ n \ a mass of formiersJ: tiej.' as basically 51 As mentioned above, compounds of formula l are All particles will be smaller than 5 ml ~ 6w., - useful as sr ~ herbicidal ~ and may be called a bad cla d .XL. The middle is in the form of a solution. Used before or after emergence - plant .. 'S6i' soya 'N ~ U4- methoxY-6-methyl "1, ~, 5-tria-., -'fi. to destroy 'undesirable' vegetation on. ob- '·, .zYNlo-2 / ... aminocarbonylol ~~~ chlorobenzeneo-, not cultivated as' id () selected sulfonamide 'S ",' '55 combating c.hwast6w. in crops , 'e.g. in the cultivation of ~ a, 95 °', in wheat .. Some of these compounds 'are obtained-' S61tozpu ~ become. in wQ, dzl, e and solution6 ~ may.be tef :: wrong vd ~ y fights ~ u 'cyberspace in crops, e.g. ~ ~ zp6sr, ~ nio, pakovfany: for use. ~', cotton, corn- and ryz.u, where they can be \,,: P · ~ 'zYklad' XLI. The agent 'in the form of a granule.' Used before or after the onset of rose- N- [/ 4,6-dimethoxy-1,3,5-triazinyl-2 / -amino-10 lun. 'use ~' kar'po ~ Ylo] .. 2,5, .. d \\ T \ 1m ~ tok8Ybenze · nosulfpna ~ id 80 "f 'nia, measures in ~ long in the invention m, means' using , in sUbst ~ ption zyVilzajaca J o'i. in order to 'cause useful changes in growth growth · -surówy ligninosultonhin of the trunk · (5-20 "0 na- -lin.;. ~ urainic sugars) l". 10 "0 l? ! 1 StosoW8-, 'ilin ~~' attapulgitowa g ", 58 nyrch in 'specific situations' advantages from the data to be used114 069 45 46 The compounds tested, their use and amounts, and the results obtained are given in Tables IX-A to IX-Y. The results are given in tables with the following symbols: O = no effect & = 10 = strongest effect B = 'burnout C = chlorosis or necrosis D = leaf loss E inhibition of plant emergence G. = Delayed growth in growth H = treatment of growth zones (stems or roots) I = intensification of -green coloring L, lodging p = pack destruction S = albinism (no chlorophyll) U = non-organic coloring 6Y == dropping of packets or flowers.% Z = formation growth. X = axial stimulation In table.ch the abbreviation "Post" means that the subject was used after plant emergence, and the abbreviation;, Pre "means that it was used before plant emergence. 40 25 of the livid growth were placed, the infestation of bloodstain (pigita ~ ia sp.), One-sided weed (Echinochloa crusgalli), gluche's oat (Ave na fatua), cassia (Cassiabora); food (Ipomoea sp.) turnip (Xanthium sp.), sorghum, maize, soybean, r.yzu, wheat and tuber, and then treated with the tested compounds dissolved in a non-toxic solvent for plants. . Simultaneously, the tested solutions were sprayed on cotton plants with 10 5 leaves of Oaczp.ie. with leaves), plants of spotted bean in the third leaf stage, · p ~ ll of bloody bean, 2 leaves, weed. one-leaf with 2 leaves, gluchego - oat with 1 leaf, cassia with 3 leaves (including leaves), morning glory with 15 leaves (including leaves), sorghum with 3 leaves ", corn with 3 leaves, soybeans of 2 leaves, rice with 2 leaves, wheat olives and lcibora with 2-5 leaves. I The treated plants and table plants in comparative trials were kept in the greenhouse for 20 'for 16 days, after which the test plants were compared with the control plants and their responses to the test treatment were visually assessed. 1_ 45 results-, in order to use the agent, type of weed, soil type, type and method of application, climatic conditions. and other factors ~ For these reasons, it is not possible to determine the amounts of the compounds used in general, but it can be assumed that it is preferable to use compounds of the formula l in amounts of about 0.005-20 kg / ha, in particular 0, 01-10 kg / ha. Smaller amounts are generally used on lighter soils for selective weed control in crops or when maximum performance is not required. Some compounds of formula 1 can be .. can be used. in very high amounts to contribute to plant growth, but larger amounts may also be used here depending on factors such as type of crop, duration of application etc: \ Compounds of formula .1 can be used in combination with other anticarcinides, especially 3- (3,4-dichlorophenyl) -1,1-di-. methylurea triazine derivatives such as 2-chloro-4- (ethylamino) -6- (isopropylamino) -symtriazine, with uracils such as 5-bromo-3-II-order. butyl-6-methyl, uracil, N- (phosphonomethyl) -glycine, 3-cyclohexyl-1-methyl-6-dimethylamino-sym-triazine- (1, H, 3H) -dione-2,4, N, N-dynetyl -2,2-di-phenylacetamide, 2,4-diorophenyoxylic acid and closely related compounds, 4-chloro-2-butynyl-3-chlorophenyl carbamate (Carbyne), diisopropylthiolcarbamic acid and its ester '30 Z 2,3-dichloroalkyl alcohol (Avadex) and its S- (2,3,3-trichloroallyl ester IAvadex BW), N -Qenzoyl-N- (3,4-dichlorophenyl) -2-amylpropropionate ethyl (Suffix), methyl sulfate 1,2-di.methyl ~ 3,5-diphenylpyrazilic acid (Avange /, me 'ester: 35 t-2 - [- / 2,4-dichlorophyloxy) -phenoxy) -propionic acid IHoelow, 4- amino-6-III-shoes 10-3- (methylthio / -1,2,4-triazinyl-4H) -one ';' 5 / Lexone /, 3- .- (3,4-dichlorophenyl) -1-methoxy -J-methylurea (Lorox), 2,2-dioxide 3-isopropyl- (1H) -2,1,3-benzothiodiazin- (3H) -one-4, a, a, a, -trifluoro-2, 6-awunite ... ro-N, N-dipropyl-p-toluidine, ion 1, 'r' - dwq.rnety 10-4,4'-bipyridinium, methanar i-1,1'-dimethyl-3- (α, α, -trifluoro-m-tolyl) / urea / Cotoran (monosodium sonate) (The action of the agents according to the invention was tested in tests carried out in greenhouses. The research was carried out in such a way that in the substrate it was possible to allow for I'i ca IX-A Compounds of the formula 65 ~ 2 -3- --4- --5-1 .., .. te 3C lC 2C tC lC 'tC o tC o 3G 3G 0 o, ooooooooo 0- oo' -------- --------., ....-------- 2G tH 'liG 2G. o 2G o 2G .0 o lG 7G 2G 5G 2C 9G 6F eu · a eu ~ o rJ) eu o ..c :: ~ rJ) ~ .o ..! ld ~ o 'C.) rAI o' {12 Ot o P "" "'4 en 1--1 6 I 7 Post 0.4 Pre 0.4 Post 0.4 Post 0.4 F - = - I ~ H _H _'- 1 ---- 1-" "" "'- I CHa Cli HH H114 069. 47 48 table continuation IX-_A I 7 I 8 I 9 I 10 I 11 l 12 1 13 1 14 I In I · 16 I 17 1 18 I J9 I 20 I' 21 I 6. Post 0.4 4G Pre 0.4 2H 4G 1H oo 9H oo SG. 9G 7G 4G Pre 0.4 G8 --------- ------------- ----- - -------- H CI H CI H POStt 0.4 2C 3C oo 1C oooooo 2G oo Posl 0.4 .f) H 7G 5G, Post 0.4 6Y Pre 6, 4 oo 1C ooooo 1e 9G 5G o --------- ---------------- ------------ FHHFH Post 0.4 3S 6C 2G o 1C oo 2G 2G 2C 2H 3G 3G 1C Post 0.4 7G 7G 3H 7G 7G Post 0.4. 6Y · pre 0.4 lH 8G 2C oo 1C oo eG 9G 8G o pre 0.4 2H 8G ~ --------- -------------------------- ------ - CI HHH CI 'POIIt 0, 4 9C ac 51 J 8H 5C 4G 1C SC 5G 9G 5C ac ac 7C Post 0.4 9G 9G 9G 5G 9G 9H 9G 9G Pre 0.4 9H 1e 9H 7G 6G 6G '9H 5G 9G 9G 9C AE Pre 0.4 I 9G .. I l 'I 2 1 3 I 4 I 5 \ Usefulness of vledlug measures The invention for selective weed control in wheat crops was tested by first performing a series of greenhouse trials. 4 such tests A, B, C and D are described below. Do A. Two deep bowls, 30 cm in diameter, made of plastic, were filled with fertilized and limed Fallsington sand dusty soil. One bowl was sown for chickens, sorghum and some grass weeds, and in the other one was sown soybean, purple cibore (Cyperus 35 rotundus) and some broadleaf weeds. As grassy weeds. and broad-leaved sticks (Digitaria sanguinalis), one-sided weed (Echinochloa crusgalli), deaf oats IA.vena f ~ tua), wild sorghum (Sorghum halepense), 40 "Ylosnice (Setaria faberii), panicle (Poa praten) - sis), stoklose (Bromus secalinus), mustard (Bras- sica arvensis), turnip (Xanthium pennsylvanicum), scarlet (Amaranthus retroflexus), indigo cow (Aeschynomene virginica), bindweed (Ipo- 45, mea hererasea) cassia (Cassia tora), weed wall herba (Sida spinosa), saplings (Abutilon theophrasti) and Datura stramonium (Datura stramonium). In addition, two cardboard cups with a diameter of 12.5 cm were filled with prepared soil and one hay of reams was filled with 50 hay And wheat, and in the second, beetroot and sugar. The above-described 4 vessels were treated with the test compounds before emergence of the plants, and the titer before the plants germinated on the surface of the soil, these compounds were sprayed in the vessels. the results and are collected in Table X, st ossing the markings - given in the discussion of tables IX. These results testify to the fact that wheat tolerates the tested compounds better than most of the weeds. 60 P roo B. Plastic bowls, 25 cm in diameter, are filled with dust-sandy soil ~ allsington and in the ground this was sown soya, baulne, alfalfa, maize, wheat, sorghum, sorghum (Ahutilon theophrasti), Serbians (Sesbania axal-65 tata), cassia (Cassia tora), PO \\ 7ój (Ipomea 'sp.), biele lun Dziedzierzawa (Datura stramonium), .rzepIen (Xanthium pensylvanicum), toe .. bloody (Digitaria sp.), .Cibore (Cyperus rotundus), a one-sided moment (Echinochloa crusgalli), wlosnfc ~ (Seta'ria faberii) and deaf ~ oats (Avena fatua) About 2 1/2 weeks after sowing, the young plants and the soil around them were dusted with the tested compounds. ~ ~ dissolved in a solution that was not toxic for plants ~ 7 ~ additive and after ~ '4 days from this time ~ Z3 ran ~, all plants were compared with plants not subject to the described procedures and visually. Niki pno.:ino In table XI, using symools. how. in the following and further tables. Do a C. Test compounds were dissolved in a non-toxic solvent for plants and these solutions were sprayed on plants grown in the ground in 25 cm diameter bowls. These solutions were sprayed on wheat plants (11 cm high, second leaf stage), deaf oats (Avena fatua) (9 cm high, 1 leaf stage), roof table (Bromus tectorum) (5 cm high, stages of 1 leaf), squares of rye (Bromus secalinus) (5 cm in height, stage of the 1st leaf), wild grasshopper (A.lopecurus myosuroides) (3 cm in height, stage of 1 leaf) and one-year-old ryegrass (8 'cm tall, 1 leaf stage). The same solutions were sprayed on the plants mentioned above, but before their emergence. The results were evaluated after 5 weeks and are shown in Tables XII-A and XII-B. Try D. Research compounds were dissolved in a non-toxic for plants solvent and sprayed on the following plants:. deaf oats (Avena fatua). 14 cm high, roof slope (Bro mus tectorum) 3 cm high, rye slope ( Bromus secalinus) 5 cm high, 22 cm high hedgehog (Kochia scoparia) 5 cm high, chamomile (Matricaria ino ~ dora) 3 cm high; wild mustard (Brassica-. 1- · 1-2-1-3-1-4-1 x R 3 R 4 R 5 l 'R 6 R 7 5 Table IX-B. Compounds of formula 22 co' a et ! ~ ~ et! ~ ctS ctS ctS. ~ ~ § .B: e ~ ctS ~ ctS o 'ao ~ ~ ~ ctS ~ EC. ~ ~ ~ ~ ~ ~.,.,' 5 fj 'o P "" " "4 C,) (]) 0 :::: $ c ... o ctS at 00 _ 'o. ~. ctS H 00, C,) O: tl: tlO LA ctS (]) C,): C 'j ~ v: ~.,., oo '00 00 N ~ H ~.,., N ::' NP " "C,: .. ~ ~ (]) 00. .n. ~ o ctS H ctS o.,. J o 00 1 "" 0-4 ~ ..c - m H o N ctS • ..- 1 r.I1 ~ ~ ~ P: l UJ .. ~ r.I1 ~ d ~ U. ~ ~ ~ ~ ~ ~ U 6 7 8 9 1-10- -1-1-1 12 1 13 1 1416 116-1-7- 18 I19I20 -----; l2; - ~ ~ - --' ---'--- 1 ---'--- 1 1 --- 1 --- 1 --- 1 --- 1 --- 1 --- 1 ---, - -, ---, ---,, ---, ---, _ ...... ...... ~ = ~ ~ l IC lIC I 4G I 3G I & C IOIO I- 3G II tC I IC I 2C I 2G IO lIC I 4H 4G 2G 2G JC 2G 2C 8G., 2C ~ g: ~ ~ G. 5G. ~~ 9G II ~ I -; - I ~ I - ;; - I ~~~ I ~~~ I ~ I ~ I ~ I ~ 9H 9G 2C 8G tC & E lC 5G I 9G 8G 9G & E 6H 9G 0, 4 '0.4 0.4: 2.0 2.0 2.0 2.0 Post Post Pre Pre Post Pre Pre HHHHHH CI H, IHHH CI H CI CI IHI H Post 0.4 38 5C O 2G 4G OO 4G O 3G le. & p f C l CI Post 0.4 7G 8G B'G 8G 7G 4G Post 0.4 BY • 5G 4G 5H O 2G & E O 3G '9G 8R tC I Pre 0.4 9G Pre 0.4 ----- - ~ --- ---'----- 1 ---- 1--1--1--1--1-_1--1 --'__ '__, -, __, - -, -, - CJ1 = O o & E 9G 9G 9G IG- Post Pre Pre HHHHH CHa 0.4 tC O ° ° tB OOIOOO lC O 9 0.4 OO ° OOOOOOO 9G 9G l C 0.4, I ' , 5G ----- F-Ictl ---; - I ----; - I ---; - IH IPost 0.4 3C ~~~~, ~ -o- ~ I ~~~~ ~ I ~ Post 0.4 9C 2H 9G BG BG 'i 9R 9G - 4G 9G Post 0.4, 9D 8G i Fre /' 0.4 2H tC 7H 5G 2G 9H I Je Pre 0.4 8G 7G BG - -------- 1 1 1 ---, •. . ,,. ---,, _ CH 3 HHH II H Post Pest Pre Pre 0.4 10.4 0.4 0.4 6e 9G BC 9G 2C 9G 9H 3C 9G 9G 2C 9 ....., u_ 8H lC 9G 9H IC 8G 2C 7G 5C 8G & E 5C 9H 9H 2C 7C 2C 9G & c 9G 9C & E Be 9G 9lJ ~ j: 9G & E • cd Table IX-B I 1 I, 21 3 1 4 I 5 1 6 7 8 9 I 10 1 ~ 112 ~ I 13 I 14 1 i5 '116 I 17 I 18 1191 20 1 21 122) Cl HHHH CH a OCH 2 Post Post Pre Pre 0.4 0.4 0.4 0.4 0.4 6C -I '1C I 69 9G 9G · DG 9H 9C I 6C 9G 9G' 9H 8C 9H 3C 7G 2C 8H 6C 8G & E 5C 9H 9H 2C I & c 8G 2C 9G 9G 9C 9G 5C I 9G 9G aG & E ---. ------'--- 1 I I __._ I IIIII '' I__ ~ 'I' _ 3C I '8G CI HIHHHHHHHHHH CI HHHHHHH CH a OCH 2 OC12H SHH Post Post Post Pre. Pre Post Post Post Pre Pre Pre Post Post Post Pre Pre 0.4 0.4 0.4, 0.4 0.4 2.0 2.0 2.0 2.0 2.0 2.0 2.0 2, 0 2.0 2.0 4C 8G 6Y tc 9G 6Y 5C 8G 3C 9G lC '1G 8H tC 8G 3C 9G 2H 2G 5G o 5G 3C 8G 9H 2C 7H 9G le 6H 5G 8G 3G 5C 9G 9G 9G 2C 8G 9G o 9G 9G 5G 8G & E 6G 9G Ot to- 'c, n ~ Io-l Io-l ~ o ~ ~ cd array. IX-B l 'I 2 I 3 I 4- I 5 I 6 I 7 I 8 I 9 I] 0 1 11 12 I. 13 r 14 I 15 I 16 I 17 I 18 I 19 I 20 I 21 1 22. , CH 3 HHHHH Post 2.0 lC 2C lC 6G lC 5G 5G 8G te 2C ac lC 3C 7C Post 2.0 8G 2H 6G 5L 6G 8G 7G 5G 5G 9G Post 2.0 6Y 8G, Pre 21.0 lC 9G 4H 9C 7G & E 2H 9G & E - 7 G & E Pre 2 ~ 0 83- 8G '9G "" II l I 1 I 1 1 I 1, 1 1 I I.' II 1 I · 1 - I 1 HHHHH OCH / CH a / 2 Post '2.0 ~ C 2C 2G 2G lC 2G o 5G lC o 5G 2C 2C 5G I Post 2.0 8G 5G' 5G 5G Post 2.0 6Y Pre 2.0 3H 5G 6G 5G '3G 9H ·. 20 Q 8G · & E 5G ~ E ~ CI OCH 3 HHHH 1; 1 Pust 2.0 2H 10 2G 4G IC QQ '5G Q o Q 2C lC I Post 2, Q, 7G 2H. 4G 6G Post 2.0 6Y '7G Pre 2.0 2G 4G 4G 2G 2G 9G o 5G 9G te le .1e \ Pre 2.0 6G 5G 9G cn Co \) en ~ t-ol t-ol ~ = = = T abli Ca IX-G Compounds formula 66 ClI gt "" "" "" "" "" ~ = = = as $ -to, .o U 5C & E. ~ 00 as ~ 6G lC 5G, ~ OJ "a OJ N ~ 5G 5G: o ~ o Pt 5G lC 5G 3G 5G ~ 0.-4 ~ ~ ~ 00 as Z ~ as $ -t Pt ~ le 7H 2C 6G as as ~ C,) ~ •.-4 o ~ $ -t ~ ~ 00 00 as o ~ ~ ..c :: '"OU o ~ oN ~ ~ tC 6G & E 00 OJ" ~. ~ ..c :: C,) :: s G te 5G o as C,) "2 OJ N 00 P -1 3G -, = ------------....: ...---------: ---- = -----... : ....--------.:. ----- '------'--------- 1 as · 0 er; le 2C as t '' "O ~ $ -t :: s ~ ~. ~ tC lC 5G 7G 6G lC lS 5G 6Y 2.0 2.0 2.0 2.0 2.0 Post Post Pre Pre HH r R ~ HR s HR 4 HR 3 ~ · 2 as ~ ~ ~ as ot; as t; 'o. () As ~, .o ~ ~~ OJ 10' o, C,) o as: <'o. () 00 '00 00 N "" "~ oo as $ -t as o. ~; :::: ~~ CO 00 --- o HI CI HHHH Post Post Post Pre Fre 2.0 2, 0 2.0 2.0 2.0 3C 3H 9G 2C 3H 9G & C 9G 9C lU 9G 3C 9G & E 9C 9G tc 8G 3C 8G & C & E & C 2C 9G 3C 8G lC 5G 2C 9G & E 4H 9G 9C 9C 2C 9G 8C I 9G & E ~ = Table IX-D Compounds of formula 19 ~ -ol 9G & E 6C 9G 9G 9C 9G 9G & C 5C SG 9H R j R 6 R 5 IIHR 4 R.CI I ~ I ~ I «S ro · ~ ro ~. ~ ro N; C,) ~ lA ~ ~ ro ro o · S 8 ~ .o ~ ro ~ .EC '. ~ ~ ~ ~ ~ ~. ..,' m ro, o; rn r-4 C,) OJ O; js ::::: .. c: ro o 00, o. ~ Ro H cg ~ ~~: e ~ ro ~ ~ ~. ~ ~ G oN ~ ~ ~ ~ ~ fr ~ oo o ~ o 0'0.0 ro ~ ro o; jo fil ~ ~ ..c: "O. o N ro.:3 1 ------- 'Ul ~ ~~~ _r: Q Ul ~ Ul- _P-t o ~ __ ~. ~ Ci ~ 004 _ ~ __ ~~ 1 I 2 I 3 I 4 I 5 I 6 7 8 9 10 11 12 I 13 I 14 15 161-1-7 --- 1-B-1 19 20 21 IHIHI CHa I Post 0.4 I 4C 5C 5U 5U 9C 3C 8G 5C 9C; Post 0.4 9G '9G 9G 9G 7G 7G Pre 0.4 & E & E 9H 9H 2C & E gR Pre 0.4 SG 3G 5G SG 5G I 5G 1-0' "" "" ~ = = ~ 5G 2C 9A 2C I 3G 9G 2H SG lC 7G le 9C 3C 9G 9G 5C I 9G I o 2G 4G 4G o 7G 2C SG lH "& E 9P 9G 9H 9G oo BG 8G o 7G 2G SG o lC 6G 2H 5G 5H 5H 6G le 3H 7G lG 9G 3H 9C 8R 2H 9G 5G 2C 2H 2H 2C 9G 2C 7G aG 2H 9G 6Y 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 Post.Po) c Post Pre PTe Post Post Post Pre HHH 'HHHH CI H OCH 3 CI HH CHa H Post PIast Post Pre P ~ re 0.4 0.4 0.4 0.4 0.4 3C 9G 6Y 3C 3R 9G 3U 9G 9R 9G 2C 9G 3C 3G 6H 5G G 7G SG 8G 9H lC 9H 9R aG 3G & C 9G 2C 9G & E 6C 9G 9G le 9G & E I: .n gig HHR NO! H Post Post Po'st ~ re Pce 2.0 2.0 -2.0 2.0 2.0 3C 7G 2C 3H aG lC SC 9R lC 9G 9G lC 7G 7H lC 7G 9R 2C 8G tC 8G SC I 3C 7R & E I 9H 3C aG 8G lC 8G 2C 6G 8G 6C 9G SG & E Ic.d. Table IX-D 1 I 2 I 3 I '4 I 5 l' 6 I 7 ~ 8 I g I 10 I 11 I 12 I 13 I 14 I 15 · 1 16 I 17 I 18 I 19 I 20 I 21 • CHa HHH, H Post 2.0 8G 2C lU 3U 9C 7C 7C 5C 9C 1e '9C 8C 9C te Post 2.0 6Y 2H 3C 8G 8G 7G 8G Post I 2.0 8D 8G 8G 5C P / re 2.0 & E & E I 3H & E 2C & E 9H 9G 9G - & E & E I. ? re 2.0 9G 9H IHHH CF 3 H Po9t 2.0 lB 3B 5G 4G 4G 1C 1G lC 1e O 2B 9C 2C 2H Pos ~ r 2.0 7G 3H 8G 8G 7G 8G Po ~ t 2.0 6Y 9G Pre 2.0 2C IlC 6H 7G 7G & E 2G O 8G 8G 8G & E Pre 2.0 5G 7G, CHa CHa H CHa, '! CH 3 Post, 0.4 0 OO 3G O ° O 4G OOOOOOP ~ e 0, 4 lC 1C le Je 1C 2G 3C 2G JC o LC 5G; 'Pr ~ 0.4 / 7G 3G 6R CH 3 HHI N0 2 H Post 0.4 38 2H 2U 9H I 2H G 8G 6G 2C 5G 2C IH 2C 2C Post 0.4 7G 3C 8G 8G 7G 5G - 6F 8G J Post 0.4 6Y 8G 7G1 Pre 0.4 I 7G IG 8C 8G 7H 5G 5G 6G 3R o. & E FHFHF Post 0.4 tC 2H o O 2G O oo lC O 2C 2C 3C o Rost '0.4 3C 8G 9G \ Pre 0.4 2G 5G O 2G O 5G 5G 4G 7G 8G 2G 8G CI H CI H CI Post 0.4 2C 2C o O 2G o OIO ooo 5G O / o 'Post 0.4 2H 4H II Pte 0.4, IO 4G O ooo O 5G 6G 8G O 5? I CI HH CI HP ~ st 2.0 2H I 2C lU IU 4H 7H 2C 2C 2C lC & C 9C 5C 1e Ppst 2.0 7G 5H 9G 9H 9G 5G 8G 9H 9G 9G Post 2.0 6Y 9G Pre 2.0 2C lC 6H 7G tc & E 2C 2C 9G I 8G aG & E P'l "e 2.0 9G 9G 6G 8G 6G 01 W er. = ~ ~ ~ = ~ = table IX-D 1 I 2 I 3 I 4 I 5 I 6 I 7 I 8 I 9 I 10 I 11 I 12 I 13 I 14 I 15 I 16 I 17 I 18 I 19 I 20 I 21 aCH 3 HH CI H Post 2.0 2H lC 2C 'lU 2C 1C 2C lC 8H lC I 2C 2C 9C 9G Post 2.0 • 8G 2H 2H 2H 2H 8G 9G & p 6G 9G 9G 51 Pd ~ t 2.0 6Y 9G 9G 9G 6G 8G Pre 2.0 9G 9G 5G tC tC & E 2C 5G 9G 8G tC & E Pre 2.0 9G 9G 8G BC aCHa H OCH 3 HH Post 0.4 3C o 5G 2C ooo 7C 2C a. 2C 3C ° o 0, Po \ St 0.4 6Y 5H 7H Pte 0.4 I 2C 2C 1C 7G 6G 9H 2C 6G o - o Pre 0.4 8G 9H 9G I CI HHHH Post 0.4 9C 9C 9U I 9U 9C 2U tC I 9C & c 9C 9C & C 9C 9C Pre 0.4 9H & E 9R 1C 2C I & E 3C 2C 9G 9H 9G & E Pre 0.4 I 9G 9G I 9G 9G 6G lH 1C I 3C te HHHHH Post 0.4 48 I 5C oo. 8G lC 2G 6G '3C Post 0.4 6G 9C GC 4G 9G 5G I Post 0.4 6Y Pte 0.4 2H tC 2H 7G 6G & E 2G 3G 8G & E 8G 9C I Pre '0.4 7G 9G "2C II CI I 2C I CH s HHH Pos ~ 0.4 tC 2C 2G tC 2C 3G 2G 4G I o tC 2C 3C Po ~ t D, 4 3G 2H 4C 3C 6G II POgt P, 4 7G 6F lC I Bre 0.4 tC lC lC 3C 2G 9H IO 1H 9G 9G 7G Pre 0.4 3G 5G 4G I 5G JF CI HHH ~ ost 0.4 58 BC 9U 9U 6C 4C lC 9C 3C le IC & C 9G 2C Post 0.4 8G 9G 9G 9G 9G 3G 9H 6G 7G 8C 9G Post 0.4 6Y Bre 0.4 lC 9G 8H: l 2C & E 2C 6G 5G 9G 9G. & E ~ lre 0.4 QG 7G 9G IHHH .HHP: ost 0.4 48 2U 9G 9G 2C 8G 9G 5C 9H 5G 9G lC I 5C 7G: Post '0.4 8G 5C f 4H 9G J 9G "Post 0.4 2H 9G 5X Bre 0.4 2C te IC aG 8G & E 7G O 7G 8G 8G aG <, Bre 0.4 9G 9G 5G I .... ~ ~ ~ ~ "" "" "" "" "" ~ Q = ~ continued. Table IX-D 1 I 2, I, 3 I 4 I 5 I 6 I 7 I 8 l 9 I 10 I 11 I 12 I 13 I 14 I 15 I 16 I 17 I 18 I 19 I 20 I 21 CHa HHHH: Post 0.4 5C 6C 1C 4C 4C 9G 9G ac 9C 1C & C 2C 2C 9C Post .0.4 9D 9G 9G 9G BG 6G 9G 9G ~ e 0.4 9H & E 9H 9G 2C & E 9H 5G 9G 9G 5C & E Pre 0 , 4 .... II 9G 9G FH CI HH Po ~ t 0.4 2G 2C 70 6G lC OO 7G 4C 3G 7G lC lC 2G Post 0.4 EG 9G 4G Pde 0.4 O lC 5G OO 1C OO 8G aG 3G O PDe 0.4 7C BG CHa CI HHH Post 0.4 5S 6C lC 2H 3R 2G O aG IOO lC 4C 3C 5X Post 0.4 9G 9G 9G BG '5G 9G 9G Post 0.4 6Y Pre 0.4 fiG ~ C 1C 70 7G 9H 2G. 3G 3G aG 7G 7G Pre 0.4 9G 3H H CI H CI HP, ost 0.4 2C 2C 5G ° le OO 40 le O 1C 5C 3C lC I Post 0.4 7H 3R 2H aG 4G Post 0.4 6F 7C 7G I Pre 0.4 6G 6G 1C 5G 3G 9H OO 1C aG 4G 5G Pre 0.4 2ll FHHFH Post 0.4 ~ H EC aG 3G lC 3G o .7G OO BG 5C O 3C / Post 0.4 CG 8G 4G 9G 9G Post 0.4 '6Y Pre 0.4 2H lC 2H 7G IO 9H O o 5G 8G 4G O 4' Pre 0.4 aG BG 6G - CI HHH CI Post 0.4 9C 9C 5U 9C 3C '6C 9C 9C · & C 9C 9C & C & C 9C Pl'e 0.4 5H & E 9H & E 9H & E 9H le 9G 9G 9C & E Prc 0.4 9G IF "HHHF Post 0.4 3C 6C 5U 5U 3R 4C lC 2C 6e 9G 3C 9C 2C 6C Post 0.4 9G 9G 9G 9G 9G 9G 9G aG EG 9R 9G 7G 9G 'Post 0.4 .6Y;' .Pre 0.4 9R l1G 9R 9G 9G & E 9R 6G 9G 9G 1C & E Prc 0.4 9G C7) ~ =. ~ To- '= ~ WN Q'c.d. Table IX-D 1 I 2 I 3 I 4 I 5 I 6 I "7 I 8 I 9 I 10 I 11 I 12 I 13 I 14 1 __ 15_1 16 I 1 ~ I 18 I 19 I 20 1 21 aCHa HHFHP, ost 0.4 28 2H 5U 5U 3C 8G 8G 3C 4C LC 2C 1R 5e gG Post 0.4 gG 3C gG gG gG 8G gH 7G 9G BG. Post 0.4 6Y 9G P; re 0.4 gR 9H 4H 9R 8G & E gR 2C 9G 8G 3C & E Pre 0 ; 4 6C 7G aCHa HH CH 3 H Post 0.4 3C SC 6G 3G SC O 2G SG 2C 2C 2C 3C 2C 3C Post 0.4 SG 3G 4G Post 0.4 6F ~ Pre 0.4 SC 2C tC 3G 3G 8G 2C tC 3G 2G 2G 3G Bre 0.4 7G 5G 4G CI CI 'HHH Post 0.4 4C 9C 3U 9C SC 3C 3C 6C 3C 5G & C & C 2C & C Post 0.4 9G 9G 9G 8G 9G 9H 8G Post 0, 4 6y Pre 0.4 & E 9G 9H 9H tC & E 2C tc 9G 9G 2C & E Pre 0.4 8G 9H 5G 9G I 4G IIH CI CI RH Post 2.0 2H 2C 8H 7H 2H O O. 9G 20 O 4G 5C tH Po ~ t 2.0 6G 7H 2A 9G Post 2.0 6F Pre 2.0 7H tc tC 5G O 9H 6C 2G 8G 8G 5G 4G Bre 2.0 8G 5G HFHH CH 3 Post 0.4 2C 2C 2H tC 3H OO & P 4G.1 2G tc 2C 7G "7C Post 0.4 4H 5H 9G 6G 9G 9G 8G 9G Post 0.4 9G 9G Pre 0.4 I 2H 80 6H O O 8H tC 2G 8G 9G 9C 80 Pre 0.4 9G 6G \ CHa R H F H Post 0.4 2H 2C tc 9H 3H 4G 2C 3C. 9H tH tC 2H tC lC 'Post 0.4 5G 2H 9G 8G 8G 9G 9G 8G 7G 8G Ol: Post 0.4 9G Pre 0.4 2H 2C 2G 7G I 8G & E 7G 2G I 9G 9G 9G & E P're 0 , 4 7G 9G .CI IHIHI OCI-J JI II I Post I 0.4 I 3H \ 3C I Su I 9G I 2H I 2C I 8G 1 2C I 6C I lC 19C I SC I 9C I 3C II Post 0.4 9D 3H 9G 9G 8G 9H 3G 9G 8G ~ g "1 ~ ~ I-ol = = ~ NI = ~ ~ ~ = = ~ ~ ~ CI ') ClIO cd Table IX-D 1 I 2 I 3 I 4 I fi l 6 I, .. I 8 I 9 I 10 I 11 I 12 I 13 I 14 I 15 I 16 I 17 I 18 I 19 I 20 I 21 •, 9G I 9G CI H aCHa H Post 0.4 9G 9G Rre 0 , 4 2R 9R 9R 7G BG & E 9H tc 90 & E Pre 0.4 9G 6G I CI Ci CI HH Post 2.0 2C 3C O 4G tC OOOOO 70 2C IO 2G Post 2.0 7G 9G I Pre 12.0 OOOOOOOOO 9G tH O CI H CI CI n Post 2.0 3H tH O 4H 3G O oooo 4G tC o I o Po.st 2.0 o tC 2G O o 70 2G o 8G 8G & E I o Bre 2.0 6G I CI CHa HHH Post 0.4 SC 3C 9U I 9C 6C 8G 7G SC & C 2H 9C & C 9C 3e JPost 0, .4 9G 4D 9G 9G 9G 4G 9H Post 0.4 6y 8G 9H I 9H Pre 0.4 9H 9H 9R I r & E 9H SG 9G & E 9G & E CHa IHIHIHIH Post 0.4 3C 6C Su SC 2C 4C SC SC 9C I SG 2C SC I 7C 2C I Post 0.4 9G 9G 9G 9G 9G 9G 9H 8G I 7G 9G 7G I Post 0.4 6 ~ I 2-chloroethyltrimethylamine salt Pre 0.4 9G & E 6H 9H 2C & E 9C I 8G 9G 9G 9G & E Pre 0 , 4 9H IH Br HH Br Post 0.4 48 3C 8H tC 2H O - 8G 4G O 6G 9C - 9G Bost 0.4 BG SH 6H 8G Post 0.4 6y 90 f Pre 0.4 7R 9H 2H 6G O 9H 6G O 6G & E SG BG CF 3 HHHH Post 0.4 9C 9C & C 9U 9C 4C 3C 3C 9C SC I & C 5C 6C 7C Pre 0.4 & E & E 9H 9H 2C & E 9H 9G 9G 8G 9G & E Pre 0.4 9R I aCHa HH aCHa H Post 0.4 4C 6C Su SC SH tC 2C sc l 9H SH & P 3H sc 4G Post 0.4 9G 9G 9G 9H 9G 7G '6G 9G 9G 9G 9G BO Post 0.4 6y Pr ~ 0.4 9R & H 9R 9H 9G & E 9H SG 9G 9G 9G 9G CI CI IHI CI I CI I Post I 2.0 I 38 I SC I 2U I 9H I 4C I SG I 7G lIC I SC I IC I sc I & C I sc I 9G Po., T 2.0 4H 9G 9H 9G 6G BG 2H 9Gc.d. Table IX-D 1 I 2 I 3 I 4 I es I 6 I 7 l 8 I 9 I 10 I 11 I 12 I 13 I 1: 4 I 15 I 16 I 17 I 18 I 19 I 20 I 21 CI CI H Ci CI p'ost 2.0 7G Pre. 2.0 9R 9R 8H 9G 9R 9H 9R 4C 9G 9G 7G & E Pre 2.0 SG -----------: .....---- = --_ 1 CH / CHa / IH CI CH / CH: d2 H Post 2.0 28 tC OO 4H 'OOO tC 2G OOOO' Post 2.0 SG Pre 2.0 5G lC 5H 7G 7G 7G 8G 2G 5G 2G 5G 30 Pre 2.0 8G CHa HH CH! H Post 2.0 2B 'tB 2H 9R 2H 4G 6G 7G 3C 5G SG lC 9C lC Post 2.0 6G 4H SG 7G 9H 4H 4G Post 2.0 6y 8G 4F P-Te 2.0 9R 9H 9H I 8G 7G & E 2C 5G 7G 8G 7G & E Pre 2, \ 1 SG I CHa HH CH / CHa / 2 H Post 0.4 48 2C OO tC O Ol 2G OO 2C 2C tc Post 0.4 8G 2H 5G 6G I Post 0.4 6y I Pre 0.4 O tC OOO 10 O 3G 2G 7G OO Pre 0.4 7G IIFHHHH Post 0.4 2 \ tC 6U 5U 9C 8G 2C 9C 3C 2C 9C & C 9C 9G Post 0.4 7G 2H 9G 9G 7G 9H 8G Post 0.4 6y 9G ~ re 0.4 I t C 9G 9R JC JC I & E] C Je 9G 9G 8G & E Pre 0.4 9G 9G 9H 9G I OC2H 6 HH OC2H 5 H Post 0.4 5D. 9C 2U 9R 3H lC 6G 3C I 3C 6G 5C 9H 3e I 90 Post 0.4 9G SG SG 6G 7G I 9G 9G 9G Post 0.4 6y I Pre 0.4 I 9R lC I 4H JC 7G 9R 2C 4G 9G 90 3C 9G Pre 0.4 8G 7G 8R --------, ----....: ....-...._--.: ....- ..; - .:. I CHa H H Er H Post 0.4 28 5C 2H 9H 5H O O 6G JC \ O 2C 2C 2C O Post 0.4 9G 9G 9G 7G 5H 5G 8G 5G I Post 0.4 6y! Pre 0.4 2H 8R JH l G 2G 50 2C 2C 3G 9G 6G te I Pre 0.4 5G 5G 7G 70 O) c: Q 'l = "" "" "" ""' "~ = = ~ continued. Table IX-D 1 I 2 I 3 I 4 I 5 I 6 I 7 I 8 I 9 I 10 I 11 I 12 I 13 I 14 I 15 I 16 I 17 I 18 I 19 I 20 I 21 CHa H CHa H CHa Post 0.4 1H O gG 2G 2R OOO ° OOOOO Pre 0.4 1C & G OOO lC OOO 70 OO Pre 0.4 5G 7R --- CI H CI HH Post ~ C 3C lC 2H 2G OII 5C 3R 4C 0.4 OOOO 4 I Post 0.4 gR gR 7G 9G 7G Post 0.4 6G 2G I 5G Pire 0.4 O 6G OOOO 2R 80 3G 4G -1 I- '-.:t ~ t-oL = = WN = T ab I ica IX-E Compounds of formula 23 I Ul C'j Q) ro ro. ~ Ro I :: · a ro NC,) I :: ~ I ~ ro '"O o ...... o R 3 R 4 R 5 R 6 R 7 X 1ZI ro I :: s-. ...... ~ ..o ro ro I :: ~ C,) ~ ~ ~ ~ ~ 'I ::' o ~ ro N a :; s-. · a Ul 1ZI Q) ro ro, ....... j C,) o :: s ... c = ro o 1ZI ro: 0 · a ro s-. 1ZI o: ~ ~ o ro ~ 'oJ) ~ ro Q) C,) ~ I :: ~ ~ ~. ....., oo 1ZI 1ZI N $ -l 0 N :: s t-.l Q) 1ZI ..o ~ o 8 ~ ro $ -l ro o ~ rP..C5 ~, .c: '"O ro $ -lo N ro UJ. ~ ~~ 00 UJ. • ~ rlJ o ... P: u CL) ~!: G ~ ~ ~ ......, HHHHR OC 2 H s Post 2.0 9D 3C 8G 7G 2R 3G 2G tC 3G 3G & C 3C 8G 2C Post 2.0 9G 9G 9G 9G 9G '7G Post 2.0 6F Pre 2.0 2R tC 9H 5G 5G & E 7G 8G 9G 8G 9G & E Pre 2.0 8G 9G, IHHHHHH Post 2.0 3C 5G 4G lC 2C OO 2G lC 2G lC 2C 5C lC Post 2.0 6F 6G 5G Pxe "2.0 IO 4G 5G OI 2G 9R 4G O 8G 6G '5G & E I ----- CI HHHH OC 2 H s Post 2.0 2H 8C lU 2C 6C tc ~ C 6C 9C tc 6C & c 9C 9C Post 2.0 9D 9R 9R 9G 6G 8G 9G 7G 9G Post 2.0 9G Pre 2.0 9H 9G 9R 9G 9G & E 9R 2C 9G 9G 9G & E Pre 2.0 • 9G CHa HHHH OC 2 H s Post 2.0 2H 7c te 3C 5C tC tC 3C 2C tc 9G & C 9C 9C Pblst 2.0 9D 9G 9H 9G 9G 5G 6G 9G 9H 4G I Po: st 2.0 9G Pfre 2 , 0 9G 9G 9H 8G 8G & E 9C 3C 9G 9G 9G & E I p're 2.a 9R 9G 'le, ..,' l ~ ~ ~ ~ = ~ ~ T ab I ica IX-F Compounds of formula 67. ... C1l., --- ----: --------- ~ - ~ ----- ~ - Ha R 4 R 5 R 6 R 1 x ro '2 .. c ro ~ ~ Ul oo Ul ~ o UJ ~ ro ' <:. J ... c = 'Ul ""' - .. o bO ~~ ro ~ rIl ro ro N .....- 4 U o ro rIl N ro ~ ~~ ro s :: Q) 8 : ro ~ o bO ~ o UJ ro N "O, ~ :: s ~ :: s ~ ro u '2 ro Q)' 1" "" ") N o rIl UJ P-4 rIl Q). ~ o, ..c: u ':: s 2;' N .. ~ ..-- i ro ro s :: us :: '.-4 pers :: 1-'4 ~ - ~ rIl 00 ro o 8: ~ ... c = "O (). ~ ~ '.-4 ~ ~ 8: rIl ro .8 8: ro ~ P..4 ~: at 8 :. o ~ 1 - '~' a Q) N ~. ~ rIl ro ~ ro Jt o ..c U ..... ..... ~ = ~ ~ & E & E I & C & c 8G 9C 9G & c 9H 6C 9G 5C I 5e 9G - 9G & E 9G I 9G & c 2G 6G 3G 9G & C 4G 2G 7G 6C 9G & E 5e 9G & E & p 9G 7G 2G 2C 5G 5C o 6G lC 6G 9G 9H 9H 2C 9G 2H 9G tC 8G 8R 2U 9G 9G 2H 7G 2C 7G 5U 9G & E BC 9G 5L 9G 3C 9D 9G 8D 9G 6Y 2.0 2.0 2.0 2.0 2.0 2.0 2 ~ 0 2.0 2.0 2.0 Post Post Post Pre Pre Post Post Post Pre Pre. . aCHa aCHa HHHHHHHH CI CH 3 HHHR aCHa Post Post Pre Pre 2.0 2.0 2.0 2.0 & D 9G 7C 9G SU 9G 9G 9H 9H 2C 9G 9R fiG 9H 7G 5C - 2C 9G 9H aG & E 2C 9H 5G 9G 5e 9G & E 2C lIC I & c 9G -9G 9G 9C I & E ~ O) T ab I ica IX-G Compounds of formula 20 21 20 19 18 17 16 15 14 13 12 11 10 9 7 - C'iS 'CJ .. c 'u) "' -.... o '0.0; ::::: ~ 6 C'iS -8 ..o C'iS ~ ~ en oo U) ~ o rn ~ 5 R 1 C'iS ~ U) C'iS C'iS N .....- 4 CJ o C'iS U) N C'iS $ -l ~~ I ~ - I --- I · -1 8 4 Re 3 R 5 2 R 4 1 R a CI HHHH I - PO: - Post I, po.st Pre. Pre Pre 0.4 0.4 0.4 0.4 0.4 0.4 0.4 9c & C 9C 9C & c 9C & C & C & C & C & C & C 9R & E & R & E & C & z 8C 9C 9C 9H 9R 9R BC 9 (. I 9C Be & c 9 (; 9C 9C 9C & E 9H I & E 9R 9H I & E & E 3C & E 9G 9C 15G 9C 3C & C 8G 9R 8G & R 9G 5C le 9G 9G & C & C 9C 9G gR 9G & C 6C & C 5C 9C 9G 9G 9R I '9R 9G 9C 5e 9C 9C 8G 9G & E' I 'I CH. CI HHH P.ost Post Pre Pre 0.4 0.4 0.4 0.4 5C 9G 7C 9G 5H 9G 2C 9H 2H 8G 9G 2R 9G 9R 5G lC 8G BG lC BH lC 7G 9R 5G 5L 2C BR 2G 1C 3G 9C 2C BR 9G & E 6G I 9G 8G I & E "" "" "" "" ~ = ~ ~ I - ---- FR CI RR Post Po ~ t Post Pre Pre 2.0 2.0 2.0 2.0 2.0 58 BG 6Y 6C 9G 9G 2C BR 6G 9G 2C 8G 2C 6R 2G 6G o 3G 8G 9R lC I 2C 7R 2C I 3G 7G "BC 9G 9G 7G 9G 5G 8G 9C & E 1 ----- ~: .....---- I. --- ...!: ------ -__ 7 _--- ~; ---........ ---- __ = _; _- F CI RRR Post Post Pre Pre 2.0 2.0 2.0 2.0 9C 9C 3C 9G & E 3C 9G 9G 3C 8H & E 9G 2C 9G 9G 2C 9G 9C & E 2C 9G 2C 9H 5G 4G 6C 9G 9G 9C 9G 9C 8G 5C 9G & E ~ co CH. RR CI H Post Post Pre Pre 0.4 0.4 0.4 '0.4 0.4 5C 9G 6Y 2R 5C 9G 9R 2C 9R 9H 9G 2C I 5G 9H gR 1- 9G 6G 2C 9G 6G 9H 8H 9L 2C 9H 2G lC 3G 9C 9G 5C 9G 9G 3C I 9G 9G 8G I & E OCH a IHIHI CI IHI Post, Post 0.4 0.4 I 5C I 6C I 9G '9G 3H 9G I: ~ \ 2C 9H I ~~ I 2C 9G I 9C I 9C liC I 6C 6G 9G 2C 8G I ~~ I gC 9Gc.d. array IX-G ~ <: O gC & E & E 1C 8G 9C BG 2C 5G ooo ~ C 8G 9H o BG o 7G 2C 3H 7G 9R ~ C 1C 90 5G I 3H 9G 2H 5C 9G 48 7G 6Y 0.4 0.4 0.4 0, 4 0.4 Post ~ ost Post Pre Pre H CI CI IH 1 H OCH 3 I 2 I 3 I 4 I - 5 I 6 I 7 I 8 I 9 10 I 11 I 12 I 13 14 I 15 16 l 7 I 18 I 19 I 20 21, IHIHI CI IHI ~: I ~ :: I, I 9H I 9G I 9H I 9H: ~ I & E ~~ ~~ I 9G I 9G \: ~ 2G 2C 2C 8G 7G 9G I 9G FHIHEH Post Post Post Pre Pre 0.4 0.4 0.4 0.4 0.4 38 7G 6Y 7C JC 9G 7G SL 9H 3U 90 9G 8C 9R 9G 8G 2C 7G & E JC 7G 9L 2C 7G 4C 3G 8C 9C SC 9C 9C & E l _. ---: ....- -: --__----: ... _ F CI HHHHH · HF CI Post Pre Pre Post Pre Bre 0.4 0.4 0.4 0.4, 0, 4 0.4 9C 9C 9C 9C 9U & C 6C & P SC 9C 9C SC 9C & C 9C 9C 9H & E 9R & E 9H & E 9H t C 9G 9G 9C & E 9G 9C I & C '& C I SC 6C 9C l & C I 3C & C & C & C 9C & E & E 9H & E & E 9R 2C 9C 9G 9C & E 9G I-oi = = CI- 'N = CI CI HHH Post Po ~ POS) t Pre Pre 0.4: 0.4 0.4 0.4 0.4 SC I 9C 9G 6Y su I 9C I 6C 3C tC I 9C I 3C tC I & E I & E I 9C I 9C 9G 9G 9G 9G 9H 4G 9H I & E I 9H I 9G I 9G I & E I 3 ~ I. 4C I 90 I 9G I 9C I & E 9H. 8G I 9H I 8G 9G I 9G SC I 8H I 8H I 3H '6G 8G 9H I 7G QIO = 9G I & E 9G 9C I 6C I 9C 9G 3H I 4H I te 9G SG 9G I 90 I tC 7G 9G SC 90 & E o 6G I 3C 9G 2G SC 2C 9G I 9H 6H I 2G o tC I & E 9G 4G 9H tC sc o 4G I 5G 8G 90 I 5c 9G 3C I 8H 9H 2C 7H 6C I 2U 9G I 9G 3H 7G 6F 4H 9G 6Y 0.4 0.4 0.4 0.4 0.4 2.0 2.0 2.0 2.0 2.0 Post Post Post Pre Pre Post Post Post Pre Pre H 1 H 1 1 IH CHa HI CI 1 ---; - 1 ---; - 1 I 1 1 F Hc.d. Table IX-G ll 2 I 3 I 4 I fi I 8 I 7 I 8 ~ 9 I 10 I 11 I 12 I 13 I 14. I · 15 I 16 I 11 I 18 j ~ I 20 I 2 ~ CH, HHFH Post 0.4 3H: SC 2H 3C 4C 6G 8G 2C 9C 9C 40 SC SC & C Post. 0.4 8G 9G 9G 9G 9G SG 9G Post 0.4 6Y Pre 0.4 9H 9G 9R 9H 9R ~ & E 9R 6G 9G. 9G 90 & E CI H H OCH. H Post 0.4 9C 6C 5U & C SC JC, te 2C I & C] H & C 9C 9C SC •. I Post 0.4 9G 9G 9G 4G 9G SG II 4G 9G Pre 0.4 3H & E 9H 9H 90 & E I & H Je 9G 9G 9G & .E Pre O ~ 4 9G 6G m IH- ~ IH- ~ I - H - ~ II ~; ~ --Po- ~ --- M ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~,, Pre. 0.4 9H & E 9H & C 9G & E 9C t C 9G & E 9G 9G Sodium Isol / Pr ~ 0.4 9G CI IHIHIHIJ; I Post 0.4 9C 9C & C & C SC 8C 9c- ~~ I ~ 1 & e & C I ~ & C. Pre 0) 4 & C & E 9H & E 90 & E 9C I JC I 9C 9G 90 9G Potassium salt /. Pre 0.4 \ ,, _ '90 ~ IHIH I. H "IH Pod - ~. ~ ~ I & C ~ SC oc 8c --- 1-9-C ~ - & - C - 2-C ~ I- & -c --- 9-e-. ~ -9-C - 9-C-. Pre 0.4 9H - & E 9H. & E 90. & E 9C lC I 9G 9G 9G & E Is p-toluenesulfonic acid salt p O4 I \ I_ ~ __ ~ __-: ---_----: - - = --- r_e _-.-: ..-, _ ~~ II -: --- 1 '---- SG_ ~ __ ~. _ FHH II H Post 0.4 9C 9C & C ~ & C & C 9C 9C I 9C & C 2C & C 9C & C tc "Post 0.4 2C & E 111 JC JC I & E \ lC tC 9G SG & E & E Pre 0 , 4 9G 9G 9G 9G I 9G 90 I -----: ----- "----; '---------: ----- ~ - = --- ---_-: -_ ~ - CHa IHIH l HIH Post 0.4-- ~ 9C 3C & C SC jc 2C SC 4C 7G 9C 9C SC Post 0.4 90 9G 9G 7G r 80 9G '80 Is sodium salt / Pre 0.4 & E & "'G 9II 9H 2C & E SC 2C 90 & E I Pre 0.4 ... I Se: 9H 9G 9G 9G I ---- ~ ----; ------; -------- ~ ----- - ---- - ----._----- ---.----. --- at --- I. .H H H CF s H Post 2.0 8e I 3B 2H 3H 9C. 6G 7G 3C 3C SG 9C. & C & C 9G l Pqst 2.0 SD SH 8a 90 SL 9G I Post 2; 0 90 \ \ 1 Pre. 2.0 I 3e 2C & E, 9G & E II & E. 1 Pre 2.0 90 90 9H I 9G, 8G 8G 60 80,. I I ---- ~ ----------- ~ _-- =: -----_---- ---- ---- --- 00 .... .. 00 l ~ ~ ~ ~. = ~ ~ CH 3. . ! lI CI-I ~ - H Post Post Pre 2.0 2.0 2.0 sc I SH 9H "1 9G 9C IEsc 9G & E I 9G 9C 9H SC SC 8G 8G 9H '9H & C I & C & EI 9H SC 90 8G & C 9G 2C \ & C 8G 9G 8G JC SG & Ec. Table IX-G 1J I 2 I 3 I 4 I 5 I "6 I t7 I 8 I 6 I 10 I 11 I 12 I 13 I 14 I 15 I 16 1 17 I 18 I 19 I 20 I 21 aCHa.H "HH Post, ° 1, 4 '2H SC 8H 9R SC O 9C 9C 2C' 4G SC 2C 90 8G CI Post 0.4, 9D 9G 9G 9G 9H 9G 9G Post 0.4 90 Pre 0.4 9R 9R 9H 9c & E & E 91-I 8G 9G 9G 9G 9G Pre 0.4, CHa FI H Br H Post 0.4 9D 7C 2R 9R 2C tC 2G 7G 9C 3G 9C 9C 9C & C Post 0.4 9G 9G 9G 9G \ .Pre 0, 4 2H 9H 9H 6G 8G 9R "9R 3C 9G 9G 9G & E Bre 0.4 9G 8G ---- CI H 'p HH Post 0; 4 8C 8C SU & C tC 2C tC 5C 3C 2C 8C 9C 2C SC Post 0.4 9 (; 9G 9G 2H 8G 8G 9G 9H 7G. Pre 0.4. 9H 9H 9H 9G 9G & E 9H 2C 9G 9G 9G & E Bre 0.4 SG \ I! CH! H CHa H CHa Post 0.4 28 3C 2R 6G 2H OO 8G 91-1 O 2C 2C te 6G I Post 0.4 8G 2H 9G SG 8G 9G SG III Post 0.4 6F 9G I & E I Pr'e 0.4 9G 9l-l 4H I 9G 8G t & E 9H I o 80 8G 8G I - ~ --- ~ - - CI H CI HH Post 0.4 38 ~ sc 9H 8H 3H OO SG tC At 2 H 2H SD 7d Post 0.4 8G 80 9G 8G 8G SG 5X Post 0.4 6P 3G I p're 0.4 lC 8G 7H 4C 2G SG 3G 8G 9G 9G 9G; . ' 5G iBre 0.4H. .I .CI H N'0 2 H Post 0.4 se 2C SC 4C 9C se 80 SC 6C SC SC 3H & P 9C Post 0.4 9G 3H 9G -9H 8G 7G 9G 9G 9G 90 9G Post 0.4 6Y 9G . ' Pre 0.4 9R 9G gR 9G 2C & E. 9H 9G 9G 9G 9G & E ~ Pre 0.4 8G j I - I CHa CHa H CHa 'CHa Pqsf 0.4 48 2C 2G 2G 3H 2H O O 4G 8e 3G tc tc O -, P.ost Q, 4. 7C Post 0.4 6Y I Pre 0.4 2U 2C le 4G 4G 8G 2C SG 8G SG lC 8G Pre 0.4 9G 5G I SG QC W 00 ~ lo- "lo-" ~ = ~ ~ o continued t; 1bl ~ cy IX-G 1 / I 2 I 3 I 4 l 5 I 6 I 7 - I 8 l 9 I 10 I 11 I 12 I 13 1- 14 I 1 \ 6 1 16 I 17 I 18 I 19 I 20 I 21 t H (jC I OC 2 H s HH OC2 ~ Post 0.4 SC 9C 2U JC 4H tc 3G 3e 3C Je 2C 6C 9G Post 0.4 9G 8G 9G 9G 6G - ~ 7G 9H 4G 9G 9H 9C pre 0.4 2U 2U 9H 9H 7G 9H 9H 2C 90 9H 2C 90 Pre 0.4 90 90 90 8G _o • .- "CHa HH CH / CHJ! H Post 0.4 3H 6C 7G 9H 3C OO 5G tC 2G - SC 3C 2C: Post 0.4 4C 9G 90 30 90 90 Post 0.4 90 Pre 0.4 90 9H, '8H SG SG 9H 9H 20 90 9G 90 / C Pre 0.4 9G -0 __- ___.___ aCHa HH CH 13 H Post 0.4 8C 9C '3C 3C 17C 4G SG SC 8C 7C & C SC 7C 3C Post o, ~ 7G 40 SO 60 50 Pre 0.4 & E SC 7G 8G SG & E 8G 6G 7G SG 3G & E Pre 0 , 4 9G I "t I OC 2 H s HH CI H Post 0.4 SC 9C 2C 90 3C 2C 70 2C SC 'Ii SG 9C. SC & P 9G I Post 0.4 90 8G 9G SG 7G. 9G 8H 8G Post 0.4 6Y '- I Pre 0.4 & E' 9G 9H 9G tC & E 9H 80 90 & E 90 O&E Pre 0.4 I 80 CF 3 HHHH Post 0.4 9C 9C 9C 9U I 5C 2C 2C 4C 9C 8C & C SC 9C 9C P're 0.4 & E & E 9H 9H 4C & E 91-1 9H & E & E 9G & E Pre 0.4. I 9H ~ .- I \ I & C I OCH 3 HHHH Post 0.4 9C 9C 5U I 9C 9C 9C 2C 3C 9C 9C & C SC 4C Pre 0.4 9H & E 9H 9H 4C & E 9H & E & E 8G I 9G & E \ \ Pre 0.4 I 8H IIO / CH 2/3 c1I 3 1 I - - IIIIIIIO / CH 2 / S CH s HHH Post 0.4 2C lC oo JC D o 0- DO tc 2C 2C OIII l Post 0.4 SO 4H 3H Post 0.4 6Y I · 1 III Pre 0.4 II 3G 3G I oo IO 70 I o DIDDI oo OCHs IHHHH Post 0.4 I 38 I 2C ~~ 19H I JC 4G I 6G I 3C I ic I 5G I 2C 3c "1 4C I lC Post 0.4 80 'SG JH 9G 9G. 4H I 4G · 1 I "Post I 0.4 6Y I, & E 2G I 9G 17G Pre 0.4 9G 91-1 JC & E 9H 9G 2C 12C Pre 0.4 8G 5H '7G 00 c.Jl oc O') ..... "" "'" ~ = ~ ~ Table IX-G I HI HI I CH3ICH ~ II 10 I 11 I- 12 I 13 r 14 I 15 I 16 l · 17 I 18 · 1 19' I 20 I 21 I 3H "I '3I-l OIO 20 LIC OOI rc l OO 2C OO l C 6G' 3C 2G 9G I & E 9G O 00 '-.::J & C & E 3C 9G 6C 9G 8C -: 9C 2C 6G 2C 9G SC 8G 80 I & E I. 9H 18G I & E I & E I 9G I & E 8G 4G ZU 9C -90 I 9C I 9C 9C 7C SC I 9 ~ SC 9C 9C 6C & E 9H 9H 3C & E 9R 90 & E 9G 9G 9C & E & E ~ I 9G I 9R I 9G 2U, 9G 3C I 9C 8G 6y lIC I 5G I 2 ~ I 9C I 9C I 181 9 7 0.4 0.4 0.4 0.4 0.4 0 ', 4 0.4 0.4 Post Pre 6 Post pre Post Post Post Pre 5 HI HJ ol HI 4 HHH 3 H CE: 3 I 2 l lj t HH NO JOI JC I SH 6G 9G 90 CI CI I CI HH Post Post Po 'st Pre Pre 2.0 2.0 2.0 2.0 2.0 2.0 3S 3R 8G 3e 6'y 8G 40 9H 3e 8G oo OO 3G 60 2a JG 2G, I, 3C 8G 2G SC 9G JC 2.C SG 7G & E I SG 2C 2G 8H CI HI ci Cl H Post Post Post Pre 2.0 2.0 2.0 2.0 2.0 3C 3C 7G 9G 6y 2G 4f-I 3R 9G "- 4G Je 2e 70 SG OI 3G O 2 <: 30 9I-1 41- {O SC I 2C 2C 2C 90. 9H 7G 98 & Eol. 9G 5G I - l I - l ~, = ~ ~ CI HIH CI -H Post Post Pre 0.4 0.4 0.4 0.4 4S 7C 8G 9G 6y IU 9H 3H 9G 9G 9R - ' & R 9R 4G 9R SG 8H JC 7d & E 2C I 2G 9H 9H I 3G & p ~ 2C 9G I 9G 9G 9G 3C I 8G 8G 9G I & E 9C I & C & C & H & E 9C & C 9C & E 9H '& E & e, I SC & E lIC 8G & C 9C 9G 9G Ot) 00 JC 9G & C 9G & E 90 6C 9G 9C 90 9G 6C 9a. & C & E 2H SO le 8G 9R 9C & E, J) C 9G 9R 2e 90 3C 9G 9H 9R 9C I 6C 9G I & E I 9H & E 9U 9G 8C 9G 7D 9C, 8C 9G 0.4 0.4 0.4 0 , 4 0.4 0.4 0.4 0.4 p · ost Post Pre Pre Post Pre Pre HHHHHHH CHa CI Br H CI H- HH Post Post '0.4 0.4 3H I 2H 90 _4C 2C 9R 9R 5C 9G 4G te 5G 8G 2a 2G 2R 7G SC SC 9G 8G .80c.d. Table IX-G 1 I 2 3 I 4 5 I 6 I 7 -I 8 I, 9 1/10 I 11 I 12 I 13 I 14 I 15 l 16 I 17 I 18 I 19 I 20 I 21 I CI - - HHHH Post 0.4 9G 90 Pre 0.4 9R 9H 9H 80 8G & E 2C 2C. 9G 9G 90 & E I • Pre 0.4 8G SG IH I 1 III - I CHa HH 'H Post 0.4 SC gC SU & C 9C, SC 2C ~ C 9C 70 SC 9C g'C 7C Post 0.4' 9G 9G 7G 7G 80 8G benzine salt Trimethylamine Post 0.4 6F: Pre 0.4 I 9G & E 90 & E 2C & E 9C 2C 9G gG 9G & E Pre 0.4 I gH 9G, --------- Br HH Brl I ~ Post 0.4 4C. SC 8R 9R 5H I 20 30 SG '8R lH 9C 9C SC 4C Post 0.4 9G 9eJ 9G 9G 9G Post 0.4 6Y Pre 0.4 8H 9G gH 8G 8G & E 9R 5G gG 90 9G 90 I - - - -_.._._- 1 & C aCHa HH aCHa.H Post I 0.4 9C sC SU 9H 6C 4C 4C 4G gC SC & C 9C SC Pre 0.4 & R & E gH & E gH & E yH 2C i 9G gO 90 & E Pre 0.4 sG i 1 --- 1 I .7G II CI CI H CI CI Post 2.0 4C ~ C 2U 8H 3C 2C SG 3C 3H 9G gC 9C sc i \ Post 2, .0 9G 9H sG 9G 9H / 8G I Post '2.0 6Y .... Pre 2.0 9R 1'9G gH 90 sG 9H 9R JC 9G 9G 2C I & E Pre 2.0 7G 9G .------ - I, ---- -, - --------, ------ - = - CI 'HH CI CHa Po'st 2.0 sC 9C SN 9U 9C lC SC & P gC 6C. & C & C gC 9C Pre 2.0 & E & E 9H 9R 3C & E 9H 9H & E 9G gG & E Pre 2.0 \ 9H "- --- ---- --- ----- - HHHHH Post 2.0 7C 6C le 2C 3C 2C -2C SC 2C 2C & C SC rC 9G Post 2.0 9G 9G, gG 90 8G 9G 80 8G SG 7G 9G Pre 2.0 gG & E 9G & E tC & E JC .., lC 9G gO 8G & E Pre 2.0 7R .9H 'sd ----- CHa HHHH Post 0.4 9G 9G & C & C 9C 9C & C 8C & C 9C 9C gG 9C l 3C Post 0.4 9C 9C' gC 9G Pre 0.4 & E & E gH & E 3C & E 2C 3C & E 9G & E & E 0.4 ..... Pre 9R ~ H 9G oc - ..) 1 "-0 =! -ol Io-l ~ Q ~ = cd Table IX-G 1 I. 2 I 3 l 4 I 5 I l 6 1 7 I 8 I 9 I 10 I 11 I 12 I 13 I 14 I 15 I · 1.6 I 17 I '18 I 19 I 20! 21 j elf \. 5C "HH NO = H Post 0.4 3C 4C 3A. 9C 3C te 8G 2C 2e 2C 2C 3C 9G Post 0.4 l 9G 9G gG 9G 8G 8G 9H 6C 8G 9H 7G t. Post 0.4 6Y I Pre 0.4 & E 9G I 9H glI lC gR gH tc 9G 80 8G & E J .. Pre 0.4 80 70 II CI HH ClI / CH a /! H Post. 0.4 3H 6C 3U 9G 2C 7G 7G 3C 2C 60 7C 3C6C I 9C Post 0.4 9G 9G 90 gO 9G gR 9G 90 90 'Post 0.4 6Y & E 8G i 9G I & E Pre 0.4 & E 9G gR gR gG & E gR 9G I -------, FHFHF Post 0.4 3S 3H 6G mi 2H 3G o 7G 50 o 2C. 5C 2A 7G Post 0.4 6G 5C 70 6G 6H 9G Post 0.4 6Y 9G 7'GI Pre 0.4 8H 30 5G 3G 9H 60 2G .gO I 9G 70 & E ---- I CI 'R CI It. CI Post 0.4 5S 4C 3G 2G 2H ooo 3G o 5C 3C tC 9C I Post 0.4 .9G 8D 8G 7G 9G & E I Post 0.4 6Y 9G j Pre 0.4 7G GC 2H 5G 60 o 5H 2C 9G - 5G Pre 0.4 & C I ---- ~ "" "~ o N" "" "" "" "" "~ = = = T ab li ca IX-H Compounds of formula 21 ~ ~ ~ = ~ = 9C & E & E 9C 9C 8G ro I ro. ~ 8 rf1 .o ro ..- 4 ~. U 20 .. I 21 ~ I ~~ & C 1-9 ~ - 9C 9C 9G 9G 9G & C 9G & C 3G 7G 2C 6G 7G 6C 9R 9R 9R l 9R 8G I 9R ro CJ c (1) N rf1 ~ ro '0 UJ. ro N 'O ~ H ~ ~ ~ ~ 9C 9G o' 0.0 H o ~~ 2U 7G le 9G "4H 9G 9C ro ~ rf1 ro s ::::: .ro N ~ - CJ - (1) o ro ~ ~ N ro ~~ D: l _I_8 9 7 2.0 2.0 2.0 2.0 Amount kg / ha 6 I Post Post Pre Pre Post Post Pre Pre u: l Q) ro •.-4 ro s ::::: ~. ~ § ~ .B b · c ~ 's :::::: ~ rf1 rf1 N ~. ~ (1), .. lo..4 ro o rf1 ro' o · a I ~ · N ~ E ~ ~ ~ (1) ~ ~ ..t :: a :; ro ~ o N Ci ~ u · ....., ~~ P-4 ~ I 10 I 11 I 12 I 13 I ~ 4 I 15 I 16 I 17 I 18 I 19 I. 9C I 7G 2C SC I 80 8G. 9ll I 9;: 1 9H & E I.,,,, Post 0.4 - 9C 6C 2H 9H 5C. OO ~ 3C 3C 2G 2H 5C 2C 2C I Post 0.4 9G 7G 9G 8G 8H 9G 9G 9G 9G P re 0.4 lC 9C 9R 4G 3G & E 2C 7G 9G 9G 9G & E I Pre 0.4. / 7H I 8R I • III, 0.4 6C I BC 2U 9H 2R 2G I 2G '. .. 0.4 9G 9G 9G 8G 0.4 9H 9H 9H 3G! 3G 0.4 I Application 5 HHR 1 H 4 H Br HR 6 ~ H HR 5 I 3 2 HH CI R 4 1 R a CHa CH:} aCHa CI HFHH Post Post Pre Pre 0.4 0.4 0.4 0.4 ae 9G ae 9G 2U I 9R 9G te 9G 7G 3C 9G 9H tC 7G tC 6G 3e 9G & E 9C lC 5G 2C 2C 8H. 6G 4C 8G 9G 9C 9G 4C I & C 8G 90 I & E CHs H CH 3 H CH 3 Post Pos t Post, Pre Pre 0.4 .. 0.4 0.4 0.4 0.4 2C 9G 6F 2CJ 2U 2H 9G 9G. 9G le 6G tC 8G 2R 9G 9R o 6G o 3G 7G & E 3H 9H o 3G 2C 90 8G 3H 9G 9G 2C / 1 6G 8G 9G I & E (C ~ 2C 8G & E 4C 7G SG 9G 9G 3G lC 3G 8G oo 8R CI I, H and H Post '0.4' 6C 5C 2G IC 3H IO-r2GIWI- OIOI & C I 9 <: Post 0.4 9G 9G 5G 9G Pre. 0.4 3G 7G Pre 0.4 H CI ~ ~ ~ = ~ = c: .o ~ 1. "'" ~ c.-d. tabUcy IX-H 19 I 20 I ~ ._ --- & C 9C & P SC 90 8G 9G 9G 9C & E 9C 9C 9C 80 8G & E 17 I 18 2C 8G 4C 9G tC, 2C 7G 6G 9H 9H 9H '& E 9C I SC IlU IC I 4C 1 O l "~ G 9G 9G 9H '9G I .9l-I 9R I 9H I SG 1- SG 9C I 9C I 8a 2H i 9C' I .sa I SG 9H 9G 9R 9H 8G 8 I 9 I 10 11 12 I 13 14 15 I 16 -I SC 2C 2C ZH 9C l 'IC 7G SC I SC 90 4H 9G 90 6G 8G 9G 6y 9G 9G 90 9H I 9G 7G & E 9H 2C -, SC 9H 9H 2C 2G JC tC 7Q 5G I 9C I- ~~ ----; ~ 7a 90 8G SG 9G SL 9G 9G 9G 6G 9G 9G SG 7G & E tC j tC 9G SG SG & E I 6G 6G I - I sc 3C I SG 6G & C oo 2G 7G 3G I 9C & C SC 9C 9G 7n 9L 6y 9G I \ I f! " I '8H 9G I 9R SG 2G 9H 9R! o '& E j 90 9G & E SC - ~ C 2U I sJ 3H 4G le 3H-- ~ 70 9C 9C 9C 9G 90 8G sa 7G 91-1 6 "' ~ I 9H '9G 8a 8G 8G & E 9H 90 90 90 9G & E I ~ "3C 3C Su 7U 9C te tC 3C 3C 2C 9C gC '3C f C 90. 9G 8G 90 8G 80 8G 8H 8G 9G gG 6y 9G 9G 9R 9G 9G 9R 9H t C 90 9G 8G I & E 9G 6C SC I 3C gR 3H oo 7G l G 2G & C 3C 3C 9G gG I 9G 90 9G 6G I gG " gG 5H 30 30 gH 2C 3G 9G SG 2C 90 I 9H 1- 5 -IHHH 6 7 Post 0.4 Post 0.4 Post 0.4 Pre e, 4 Pre 0.4 Post 0.4 Post O} 4 Plre 0 , 4 CHa I Po.st 0.4 Pre 0: 4 Post 2.0 Post 2.0 Post 2.0 Fre 2.0 Pre 2.0 ---- ..Po.st 0.4 Post '0, 4 Post 0.4 p ~ - ~ 0.4 4 H NO! OCR, 3 I, HHH 2 HHH '' 1 CI CI CI H CJ IHIHI CH 3 IH l Post 0.4 Post 0.4 Post 0.4 Pre 0.4 ----------- CH.IHIH NO! H '-Post 0.4 Post 0.4 Post 0.4 PTe 0.4 Pre 0.4 CH, IHI II I 'CHICH, !! IHI Post 0.4 Post 0.4 Pre 0.4 Pre 0.4 II., J Ci 1 H l, H 1 CI IH' I / SO salt gave jj! I ---- ---....: .. ~ III J '' - table IX-H 1,, I 2 j 3 I '4 I 5 \ 6 I 7 I 8 I g I 10 I 11 I 12 I 13 I 14 I 15 I 16 I 17 "I 19 I 19 I 20 I 21 \" - 'aCH a HHFH Post 0, .4 SD 9C l 5U 9C QC 4C SC 6C 9C * SC, 9C gC »9C 7C, Post 0, 4 90 9G 7G 7G gG 9G 9C Post 0.4 6y Pre 0.4 & E 9G gR 7R 2C & E gR 6C gC 9R SC & E "Pre 0.4 9G 90 8G F H H H 'H Post 0.4 3C SC 2C 90 gC. SO 4G SC 2C 6q 9C 9C gC 90 Post 0.4 8G gG. 8G 51 8G gH. Post "." 0.4 6 [mu] f Pre 0.4 gR 9G 9R 7G ~ G & E gG gG gG gG gG & E aCHa H R Cll a H Post 0.4 & C 7C SC 6G 8e SO 4G 7C & C 9C & C SC. SC 3C Post 0.4 7G ~ G. 7G 7G Pre 0.4 '... & E 7C 5C 7G SG & E 7C 4f & E 3C 4C & E "Pre 0.4 8G 7G 7G 3G / CF & H .HHHP o_st Q, 4 9C 9C lu 3D SC'. IC IC 4C SC .2C I & C 9C gC 2C 1 Pre 0.4 8G 2C gR 8G 8G & E gR 9H & E & E gC & E 1 Pre 0.4 8G, I aCHa HHIH 'H Post 0.4 9C gC 4U gC gC 2C 2C 4C' gC SC, EC 5C 9C & E ~ e 0.4 & E & E 9H. 9H 4C. & E gR & E. & E gG gG & E Pre 0.4 8R a / CH 2 / s-CHa HH a / CH 2 / a-CHa H Post 0.4 3S 3C 2G SH OOO 2G 2C O, IC Je lC O Post 0.4 5G 4H 1 I Post 0.4 BY / I i II Pre 0.4 BG OOO o BG OIO 'OO 5 "GI III i IIII aCHa H OCH ;; II H p ost 0.4 48 2C I te gH tC lC SG 2C 2C 50 IC 2C 3C 2C \ Post 0.4 7G 7G 8G 30 7G I 9G. Post 0.4 6y P, Te 0.4 gG 2C 2G 9G 8G & E I 9H 2C SG SG 7C & E PTe 0., 4 II SG .'1 CH 3 III, CHa H CHa CH ;; Post 0.4 2C 2C lU le le I 3G O le 2C 2C 2G 2C 1 2c.1 2C I 6G I Post I 0.4 9G 4I-l 7H 5H 8G JG 6G 5H 4Q Post! 0.4 6y 7G 'I \ I I I! "- cc. ...: t ~ ...... ~ = ~ = tO .QCl · cd of Table IX-H, 2 I 3 I - 4 I 5 I 6 I 7 I 8 I g I 10 1 11 ', I 12 I 13' I 14 I 15 I 16 I 17 I 18 I 19 j 20 I 26 1 CHs',. ICHs IH, I CHa ICHs I Pre I 0.4 II II 8G \ ~~ I 4H I IC I IC I 9H l 8H I ~~ I 9G I 7G I. 3C lIC Pre 0.4 7G FIHIHIHIFI Post I 0 ', 4', 1 9C I 9C I 9C I 9C I 9C I 9C I l CI sc I 9C I 9C I 9C I 9C I 9C I & C Pre 0.4. 9H & E. 9H & H 7G & E gH gH 9G 8 ~ 90 9G IFHFHF, Post 0.4 2C 3C. 7G 4G 4H O. O 7G lC '2G 2C 70 O 9G Post 0.4 80 3H 7G Post 0.4 6Y 60 PTe 0.4 8R 60 2R 40 20 9H 6G 40 gO 9G 4G & E ~ CI H CI H CI Post 0.4 3e 3C 3G O 5C OOO lC O 5C 9C 4C 90 POst 0.4 '9G 80 80 8G Post 0.4 6y \ Pre 0.4 8R 70 r 3H. 50 O 6G 7H 8G 90 I 9G 8H & E aCHa HH CI H Post 2.0 9C 90 2U & C 9C 90 2C 8G I & C 2C 90 2e 9C 90 Post 2.0 8C 90 5C '90 SC I 70 80 90 8C I Pre 2.0 '& H, 90 9H 9R 9H & E te 2C & E 9G 90 & E I Pre 2.0 f. 9H 80 • l CI HH CI H Post 2.0 9C 3H tC lH & C 50 lC · lC 2C 50 & C & C 9C 9G Post 2.0 5D 50 60 5G 60 8H se, 90 5L P ost 2.0 Pre 2.0 2H lu 90 lC lC '& E JC lC & E 90 90 & E Fre 2.0 80 90 80 70 7H 70 ..... Cll a HH CI H Post 0.4 gC 3H 50 lC 3C 5G o 20 2H 'lC 5C gC 5C JC • Fost 0.4 5C 50 2H 50 50 90 90 70 Post 0.4 9G 9G 5L Pre 0.4 i lC le gH 40 lC 2e 10 gO 90 9G 90 & E Bre 0 ~ 4 4G SG 40 70 F, CI HHH Post 0.4 9G 2H 2H 3H 2C 2C lC le tC lC 4G 2H '5C 2C Pdst 0.4 9C 3C 80 70 3J: 1 60 3G 80 40 30 80 9G gO J Post. 0.4 gG 8G 1t 'Pte 0.4 20 10 9H tC tC & E 4C 3C gO 90 90 & E Pre 0.4; 80 9G 5d 60 70 ~ ~ "" "" = = ~ ~ ~ = O ") ~ table IX-H 1 I 2 I. 3 I 4 l 5 I 6 I. 7 I 8 I 9 I 10 I 11 I 12 I 13 I 14 I 15 I 16 I. 17 I 18 I 19 I 20 I 21) CI JH HHH Post ~ 0.4 '9C 9C 5U & C 5C & C & C ~ C & C 2C & C & C & C 9C Pre 0.4 9G gG. gR gG tC & E '2C tC & E 9G 9G & E Pre 0.4 9G 9R 50 OC 2 HGHH OelH IR Post 0.4 5C gC 2C gR 5C 1C lC 3C 2C I 40 6C 8H 6C' 90: Eost 0.4 9G ~ O 80 50 30 6G 9H. GO \ 90 Post 0.4 6y I Pre 0: 4 9R 8H 2C tC lC 9H 9H 60 90 8G 6C & E Rre 0.4 4H 40 5G lr, CH ~ HH CHa • H, Post 0.4 9C 7C 70 gG 2C O ° 7G 2C 6G '9C 3H 6C' 90 Pnst 0.4 90 9G 9R. '90 90 / Pre 0.4 gR 2C 9H 8G 8G gR 9H 90 9G 8H 90 / & E Bre 0.4. 9G \., CI IHI, H, IHI CI I Post I 0.4 I 9C l 9C l ~~ I 2u I 9C lIC j 6G lIC I 3C 1 2C I & C \ 9C I 9C I & E Br ~ 0.4 9G 9R 90 80 & E 9R- 90 & E ~ E 90 & E l FI H CI HH Post. 0.4 4S 2H 7G lIC IC 10 la 80 40 2G SG 70 4C 9G I Post 0.4 80 5C ~ O 80 6F gC Pust 0.480 I 2C 70 20 20 9H 3C 10 9G & E 9G & E Pre 0.4 80 70 - CI HH CF 3 H Post 0.4 48 2C SH, 8H 2l-i I o ° o IH le SC Scl 2C 9G Pos ~ 0.4 8H 31-1 gG I fi 90 9H 70 I Post 0.4. 6y 90 I I I 8G I Pre 0.4 7G 70 ... 7R I 30 20 8H SG O 9G 8G & E I I I sc I 2G I 2C I 9C I H H R! 0.4 3C SC lC le F F Post 6H 2C 3H 3C SC 3C Post 0.4 80 9G 40 gG l 8b I gG 8G 9G Post 0.4 6y I ClO I aG. Pre 0.4 '"9H IC gH 3GI O & E I 3G 4G 9G & E I. I" Plre 0.4 90 II' \ III 2.0 3G I 2G O lG I 6G I 9H 2C IH ',' ~ 1 1 -1 HH Post 3C 2f-f 2C O 60 O 8G II 2.0 80 4C II Post I lG · 1. 90 8G I I I Po'st 2.0 6Y 9G \ 9G I 9G I 9G! l. II Pre I 2,0 8Il 9H OIO & E lH O & E IIII ~ = ~ ....... = N to "to" ~ = = CQ ~ ..... ~ o ~ ~ I- 'e ..., cont Table IX-H; ~ 1 I 2 I 3 I 4 I 5 I 6 I; 7 I 8 I 9 I 10 I 11 I 12 l 13 I 14 I 15 I 16 I 17 I 18 I 19 I 20 I 21 Br HH Br H P'ast 0.4 7C 6C 5G 4G 5H OO 50 lC lI-l 9C & C 9C 9C Pajst 0.4 9G 9G 9G 5H Pre 0.4 2H lC 9H 3G 3G 9H 8H ~ 4G 9G 9G '9G & E Pre 0.4 7G 9G aCHa HH aCHs H Piast 0.4 BD 9C 5u 5C 9C 2C 3C 5C 9C 4C '9C & C 9C 6C Hub 0.4 9G 9G 9G 8G 8G gO 90 9G Post 0.4 6y 9H I Pre 0.4 9H & E gR & E 9H & E I 9G I 9G 9G 9G & E III - ~ -----_... ----,; 'CI CI H. CI CI Bast 2.0 ae' 9C lC Je te le 4C 3G · 4C Je gC 9C gC 9C Past 2.0 9G 2G 7G 9G 9H 3H I Pre 2.0 8H 9H 9H 3G 2G 9H 9H JC gG gG. SC&E! Pre 2.0 SG 9G! HHH CF'8 H Post 2.0 SS 2H 5G lU 2C °. 7G 50 3G O 2C I & P 3C 9G Past 2.0 9G 9G 8G 90 9G 9G I Past 2.0 6y & E I Pre 2.0 4H 5G 3H / 'O 3G gH 2G lH 9G 8G 80 I Pre 2.0 9G IT table IX-J Compounds of formula 68 I ~ III fil m! Q). ~ Target ~ I • target mmu ~ R 3 R 4 R s R 6 R 7 IX 'c - + - JN o., ..- 1 o ~ fil m "O m ~ $ -l'.-4 ~ ..omm ~ ~ C,) ~ ~ ~ ~ ~ .. ~ ..o ~ m N c :; $ -l '8 ..c :.: 0 Q)' tS m ~~ ~ 1 "" " "4 C,) o :: s goal o fil goal 'a H fil o I ~ ol ~ bu ~ m Q) C,) ~ .§ .8 ~ ~' r- ~ o I o CI) N :: s 'NQ) w ..o Q o .3bb mt: target o :: s' 0 CI) G ~ ..c: CiJ I target $ -lo N co U UJ. ~ H ~ ~~ ~ e; .. ~ U) ~ ~ U · ...... ~ ~ ~ ~ ~ H 1-1 HHH CH 3 Post 2.0 3S lC 4G lC 2C OO 6G 2C 4G JC O 2C 7G Post 2.0 5H SG 3G 2H Post 2.0 6y Pre 2.0 SH lC 2H JC lC & E SC JC 6G 6G SG & E Pre 2.0 6H II -... IIHHHHH \ OCH 3 Post 2.0 2C 2C SG lH JC OO 7G 2C 2C 4G - 2G Je P'ost 2.0 3G 7G SG 7G 4G I Ptre "2.0 70 lC 2G 3G I 2G & E 3G 6G 7G SG SG & E Ftre 2.0 7G I- '= ~ 1 I-' = ~ ~ ~ ~ = ~ ~ Table IX-K Compounds of formula 69, ~ ~ ~ = ~ ~ 8G _ & E CIS ~ o: SU 221 ~ ~ I & E I & C & E GC I 9G 9H 2C 7G 9C 9G 9G SC 90 & C 90 SC 9G 9C 90, ~ ~ G., ......, I '~ I ..o ....... ro t Pot' 1 "'". P. Cl) ff ~ o N ~ Pl ~ ~ -1-9-j20! -2-1- 3G I & C I SC OO 60 O 3G 9H 9C I 2C 7G & E 3G 3C 9G 70 I & E 1C 9C 7G 9G 9C 8G 9H I ~ 9H 9R SC 9G 3H 90 9l-! 2C 8G & E & C 9C - I 9H II 2C 5G I 3H 90 8H 2C 9G 9D 2.0 2.0 2.0 2.0 I 2.0 2.0 2.0 2.0 Post Post Post Pre Pre CH 3 OCH 3 HIHHIHHHHH CI II, I ·. - 00 I l 'I I I. Q) I CIS. ~ ~ S :: R 3 II R4 I R s R 6 I R_ 7 I X,. ~ ~ Ro ~ ro ~! '~' ~ I ~ · .o ~, CIS..8 C, ~~ I ~ ~. ~ ~ I '..o p. CIS I ~ tl (1J O :: J' s :: .. c: I ro o IW I .. I ~ ~ ": ~: 2 I ~ ~ ~. ~" 3 . ~ ~ .3 \. ~ _ II l.§ ~ ~ I, ~ - + - J ~ '0.0 I CIS ~ en.:J o WQ) CIS ~ __________ Ul W ~ ~ ~ ~ __' 0_ ~ _ ~ _ ~ _0 ...._._, _ 0__ ~ __ ~~~ ~ 1 i 2 I 3 I 4 SI 6 7 --- 8- 9 I 10 1] 1 12 13] 4 -I] S 16 17 I 18 CH 3 1 HHH li I CH 3 Post I 2.0 '3H SC 3D -; ~ 2C 8G I 4C 1e 3G & C I Post 2.0 9G 8G gG 9G 9G 7G 9G 9H Post 2.0 6y I, Pre \ 2.0 '9H 9H 9H 8G 9G & E 2H 4G & E, Pre I 2.0 I' \ 9G l I SC SC 9G 90 6X "Post I Post, Post IH Pre jl CI IHI 3H 1 2C IO 80 sH 6y 8G OI 7G SG I 1C I- "= Ol? O & E 40 9C O SC 7G 9C 2C 9H 90 9C 9G 8G 9C 9G JC 30 OOOI 6G 2C 7G 70 2G 4G 9G & E OO oo 2C \ 1 / 2C 6G 70 90 I 9G 9H 5H 90 tC 9G 90 2H 80 9G I 6G 2C 4H 90 90 & D 2.0 2.0 2.0 2.0 2.0 0.4 0.4 0.4 0.4 p · ost Post Plost Pre Pre Post Post Post Pre aCH 3 aCHa HHHHHHH CH 3 - cont table IX-K "" "" = (O f3 I 14 I 15 I 16 I 17 I 18 I 19 I '20 I 21 I 22 9 I 10 I 11 I 12 8 7 6 15 4 3 2 1 I) IIHHH CF 3 H OCH 3 Post 2.0 38 lC OO 4H OOOOO & P & P SC O Post 2.0 8G 9G 9G Pbst 2 ~ O 6Y 2C Pre 2.0 OO, OOOOOO & C 9G OOHHH CF a H CHi Post 2.0 tC lH OO 4H OOOOO & P & P SG O Post 2.0 6G 9G, 'Pre 2.0 Pre 2.0 OOOOOOOO & C 9G OO al 5G I! IRHHH 'CHa Post 2.0 4S 2C SO lC 3G O 8G 3C lC 70 3e SC 8G -I Post 2.0 8G 9G 7G I 80 Post 2.0 6Y S: OI Pre 2.0 lH \ 7G 6H 7G 4G & E . ~ 2G O 8G & E SG & E! ~ ~ ~ = O "). ~ Table IX-L Test compound Application No. kg / ha ctS ~ 00 ro ro N ....... 4 CJ o ro 00 N ro $ -I ~~ ro ~ w ~ Q ~ o '0.0 $ -I o r.J2 ~ ro N "O ~ $ -I; j ~; j ~ ro · 0 rn. ro CJ · S Q) N Ul P-4 Ul (1). ~ o ~. ..c: u :: s (5 · N ~ o :: ro ~ CJ ~ •.-4 o ~ $ -I ~ ~ rJ) Ul ctS o ~ ~ ~. "O u. ~ ~. · S ~ N ~ I., ..., 00 ro 'O rE ~ I ~ ro' i-4 o ~ ~ _ P-4 .. ~ OJ · a OJ N ~. ~ Ul ro ~ ro $ -I o. .o U "" "" "" "" = By-product of example II Post Post Pre Pre 0.4 0.4 0.4 0.4 9C 9C .3U 9G 9H & C 9H 4H.I 'lC 9G 9G 9H 9H lC 9R 9H 9G & E tc 9H 2C 9G SG 6G 9C I 9C & E I 19G 7C 9C 9C & ET ab 1 ica IX-M 2 bundles of formula 71 R 1 x "z ro" a ..o ro ~ o ~ rf). oo UJ ~ o U2 ~ ro ~ C,) ... c: ~ rf). .......... o '0.0 ~~ 2 lfJ. ~ Co N ......- l c. ;. o te rJ) N ro / -; ~~ ej ~ Q) ~ ~ CO. ~ I rf). ro H o I- 'I-' .... ooo 2G -oo 9H 2G o. 2G & E 50 2G 20 tc 40 JC .4G tC 8H tC 7G & H tC 9G tC 9G ~ ~ ~ = ~ = te. I 9 ~ 9G 3G 2G 9H 9R o 90 90 9C & E 9G I & E 5C, 1_ Je 8G 7G 9G & E 6C I & C 8G & E 9G 5C I & C 7G 2C I & E 9G I- 'I-' ~ 9C I & E 2C 1,1 9C 8G 9H 9CI9CI9C 9G I \ 9G I '& E 9G 9G tC 60 4G 5G 9H 9H 9H 7G 5G SC 8G 3C 8G tC 5G 8G 5H 9G 9G 9R 8R 3H 9G tC 9G 3H 5C 9G 6C 9G SC 3C 3R 9C 0.4 0.4 0.4 0.4 0.4 ./ 2.0 2.0 2.0 2.0 Post Post Pre Pre Post Post I Post Pre Pre CHs 'CH a CHsO- CHsO- formula 64, formula 9 l' formula 73 CHs CHsO- Post Post 0.4 0.4 4S 7G 6C 9G 7G 3H 70, 2C I 20 8G o 2G 3C o 9C I 2H 9G 3C 'SO1 I, 2 I,,, I II-14 I 15 I 16 I 17 I 18 I -19- formula 73 I CH 3 I CH 3 0- I ~~: t I ~: : I - 6Y II 8H I 9G I 9H I 9G I 7G I 9H I 7H I 7H I 9G I 9G I 9G I & E '--------: ------ ..; ... , -------: ------- ~ ------,. ---- ....: ..-_- formula 73 CHaO II CH30- Post 0.4 2H 6C 2G 5G 2H OOO JC. O le 5C 3c 9C Post 0.4 5G gG 70 5H 9G 6G Pre. 0.4 6G 8G 9H 5G. O 5H 6H & E 8G 9G SG&E design 64 Cfl30 CHaO. Post 0.4 5C 7C 2! -1 9H! 8C 50,7G 5C 8C I 4C ~~ .---: ;;; ~ Post 0.4 8D, 90 8G 9G. 9G 9G 9G Post 0.4 gO and Pre 0.4 l 9H 5U 9H. .JC JC & E 3C i I, C 9G 9G SC & E Pre 0.4 9G 8G 8G 9G, 'I IG I 9G ~~ - ~ -3 ------; H30- Post - ~ 3C SC I JC 9G '& C lC JC 7C 9C 2C SC', 9C 'I 2C 2C l I Post 2.0 70 8G 7G -, 6G 6G 5G 50 7G Post 2 ° 3Y,. . Pre 2: 0 2C 9G 9R 9G 7G & E 2C I 3G 9G 90 I & E & E I Pre 2.0 8G I 8G! ! I formula 72 CH 3 CHa Post 2.0 SS 2C, I, JC JH JC O O 8G 40 with 4G 20 I SC JC _. ~~ - Post 2.0 6G '2H 50 4C 5G 8G SG l -,. Post 2.0 6Y 8G I Pre 2.9 Je & E 3G 7G JC & E 2C 2G 7G 8G 9G & E Pre 2.0 70 SG6G I ------- ': ----------- ----, ----, ----, -------- formula 64 CHa CHa Post I 2.0. sc I 2U 3U liC 2C SC 8G 7C 9G 2C I 8G 2C & P 8G Post 2.0 9G 4H 9G 8G 9G 8G gC 8G 8G 9G Post 2.0 6Y 9G Pre 2.0 JC & E 9G & E 2C & E 3C 9G I 9G 9G 8G & E Pre 2.0 9G and 7G 9H "l '~ _ pattern '73' CHa CHa Post 0.4 3G I 4H 5G 4G I 3G 2G O 3G il 2G I 4G and 2G ~ C 20 2G Post 0, 4 5C I ', Post 0.4 8G. II Pre 0.4 SO 3G 3H SG 30 7H I 4G I 30 8G 8a I 7G O formula 74 O "CHa I, CH30 Post 2.0 SC 6C 3U II! LC ~ C JC I 2C I 6C I 6C I 2C & C, SC 9G I Post 2,, 0 9G 9G 9G 80 I 8G I 90 I 9 ~! gG Post 2.0 I • 6Y 5X I i, continued array IX-M "" '"" "" "~" "" "" "" ~ ...... ...... t + ;; .. = ~ ~ I-' I- 'en cd "Table IX-M 17 I 18 I 19 9G 'I 9G 1 -----';:; 16 & E 15 9G 9.rw I Il I ~ 2 I 13 I 14, & E I gH-I ~ ~~ 1 / & E I 9H 8 & E 7 6 5 2, .0 2 ~ 0 1 4.P, re 'Pre 3 I. CHsO 2 CH, 3 1 formula 74 I formula 9 H CHa Post I 2.0 2I-f lB I 30 lC OO 3G IOOI & P 9H O- te 6H Post - 2.0 7G 60 80 70! Post 2.0 6Y (I '\ I gH 1' 2G Pre -2.0 60 70 5H 2B OO 90 gG 9G 2C Pre 2.0 i III 9G II 5G I '--- ------- --- - formula 9 .... CH ~ CHa Post 0.4 31-1 3C 8G 2C 2H le 2C 60 2C lC lB 9H tC Post 0.4 I '80 3H 70 30 8G 5G 9G Post O, ~ 6Y 90 Pre 0.4 5G 6G OOO 9H OO 5G & E 7G O --._--;. ~ ~ T ablic ci IX-N ~ Compounds of formula 75 ~ I and IIIII ~ RRRRRX. Method number 21 ~ I. ~ .§ §.! <:. I, 3 I 4 I 5 I 6 I T I of use kg / ha rf) ro ro ro o s :: e. .-4 ro ~ ~ CJ · ..j-) ~ s :: ~ I -c ro N - $ -. 4 •.-4 ~ ul rf) N ~ I · ....., Q) I - I ro r-4 c .; Q) o :: s c ~ ro o rf) -o ...- 4 10 \, 1 $ -. 4 ~ ~ ~ ~ ~. ~ ~ ~ · N ~ C .z ~ ~ ~ .r ;; ] ro $ -. 4 ~ o ~, o rf) - ~ ..c "O ro $ -. 4 o N ro ...- 4 ~ ~ co U1 ~ en. Pt oo: U. ~ ~~ P- 4 o: ~ e) HIHIHIHH CHa Post 2.0 2H I 2C ~ 8G 2C 2, C 40 7G I 2G gH 6G 40 2C lC 70 "Post 2.0 8G 2H SI 2H 70 SG 2G 5G ~, Post 2.0 6Y 70 6G I ~ 'Pre 2.0 lC 9q 2, G 90 70 & E lC 5G 60 - 5G 90 Pre 2.0 8G 8G' -. I H I H I H I H I H I H - I - Post --J 2.0 28 2C I 5G I 20 lC O O I 60 20 20 I 2G "tC I 3e" I. tC Post 2.0 3H 2H -. 6G 5G Post 2.0 6Y 4G Pre 2.0 I 6G I tC I tC I 40 I 4G I & E I 50 I b 1 7G I - I 7G I 5G Pre 2.0 6GT table IX-Q Compounds of formula 76 rl And _. u: l C]) ctS Method ctS. ~ ctS ~ R 3 R 4 R 5 R 6 R r Number of kG-ha ctS NC ,,) ~ ~ application ~ '"O o •. -4 ou: l ctS ctS ~ H '.-4 ~ I ro ~ ~ C ,,) ~ ..., ...: J ..., ...: J ~ ~ .. ~ ro NQ; H' a Ul Ul: o, C ]) ro .....- 4 C ,,) o :: s ..c: ro o rJl ctS · a ro H o ro ~ bJ) '~ ctS Q) C ,,) I ~ ~. ~ ~ ~. ...., o: J 'NQ) u: l I. rJl NH :::}' 0 N ..c: "O ctS, .Q l ctS H ej CI rJl ES ~ ctS H o N" U ~~ f = Q ~ ') \ ~ UJ. 0-4 ~ IU. ~ .., ~~ ~ ~ ~ · HHHHH Post 0.4 4C 5C lC I 8G 2C lG 7G 8C 9H 4G 3C lC 3C 7C I Post 0.4 90 80 gG II 8G 5G 7G Post 0.4 6Y I lC Pre 0.4 SG 9G 9H 9G 8G & E 2C le 9G 9G & E gG Pre 0.4 \ 8G 5G '"II --- Table IX -P Compounds of formula 7.7 IIIII .1 I rJl! Q) ctS i ctS method .. ~ ctS ~ R 3 R 4 R s R 6, 'RT Number kg / ha ro NC ,,) ~ use ~ ro "" O o ..... o ~ I rJl ctS ~ H. ~ ~ I ro ~ ~ C ,,) ~ ~ ~ .. ~ I ro N ~ H · a · ..c: rJl rJl: 0 C]) ro I .....- 4 C ,,) Q) oj ctS o 'a ctS HI ~ ~ ~ ~ ~ ro Q) C ,,) ~ ~ ~ ro I ~. ~ O \' 0 N :: s' N ~ ~ IC]) u: l .o- ro H 'C1: S o - :: s Ul S' ~ ..c: '"O ctS H o to1 ctS DI ~ ~, __ a: l__ ._UJ .__ ~ en ~ ~ U. ~ o ... ~ ~ ~ ~ HHHHH Post 0.4 4C 2C. Je 5H liC o I lC 3C 2C 2C .9C 8G 5C 5C Post 0.4 8G 3H 8G 8G 8G 9G Post 0.4 '6Y 6G Pre 0.4 I 9H 2U JC 4G 5G & E 2C 2C ~ G & E 9G & E Pre 0.4 90 6H AND 6G 80! i ----- ~ ~ 'l ~ ~ 00 ~ ~ ~ = O') = Table IX-Q Relations about wZfJrze -78 ~ ~ ~ = = ~ .......... ~ OO re 5G 4G 2C II I, C 1G 3C 2C 7G 4C 8G & C I 2C 50 90 2C '-9G IC 5G SC 90 9G o 2G 17 1 18 I. 19 1 20 r 21 ~. ~ ~. ....., '§ II eu ~ ~' o · a. ~ · 5, ....... 4: S ~ "Q) ~, 0 ~ - ~ &: ~ ~ tS o 1C I 3G 9R ~ ~ ~ C) ~ ...... o ~ H; ...;; ...; u: lu: l ~ o ~ ~ r-- "O ..... Q; U ......, · N ~ ~ & E o ~ ... c: u; jau: l Q). ~ O ~ C) · a Q) N u: l ~ ro · 0 rn ~ N '" O ~ H ::: s ~ ::: s ~ 6H gC o '0.0 H o UJ.JC 5H 9U 9G 9H I Jo I 11' I 12 I 13 I 14 1 15 I 16 I 9 ~ ~ 'Q) - ~ ~ ~ 2C 2H 5G 5C 9G 8 I 9C 3C 70 6Y ~; ...; u: l ~ c1j N, ....... 4 C) o c1j '(f) N ~ H ~~ 7 0 , 4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 Kgl.ha quantity Post Post Post Pre Pre Post Post Pre Pre 6 / Application method 5 IRHHR r JC I oo 4G I 6G I JC JC I JC JC o 2C II 2C 6G 8H I 8H Post 0.4 2C SC 8G "I 60 I 2C I o ~ - ~ oo tC I sc Post 0.4 8G 7G, I 70. 6G I 9G Post 0.4 6Y I I Pre 0.4 1C 5G i lC o o lC .. 2G · 2G tC o I o I o I 'Pfe 0.4 6G -I! 6G II .- SCI 2e IOI 9C I 9H'I 4G II 80 r 5C 9R 8G I 9G II 4 F II CI R 6 3 HHHR s 2 R 4 H CI CI FHR 3 CI o FHR CHs H Post Post Post Pre Pre 0.4 0.4 0.4 0.4 0.4 6D 2H; 6Y lC 9G 6G 2H 5G 2H 8G JC 3H IC top IC 2H 2C o le 9G 9R JC 2G 7H 2C 20 5G le 7G 9G I & C I 2C 70 2c .. 1 2C I _9G I 9G 2C 8G O .... .N = HC1. CI H H Post Post Pre 2.0 2.0 2.0 1B. 211 tC 3H o 3G o 5G IC 3H O o 5G O 2G 7G 4G o O o o tC 9G 3H 8G o 2C O o CI CI CI H 4f I-I Post Post Pre 2.0 2.0 2.0 2.0. 3H 8G 6Y 4C 9G 4G OO 2G 2C 2H 80 IC OO o OOO lC lC O 2G 2C 9G 5H 3C 9G 5H tC- o these O \. "./ ~ ....... ~ = ~ =" "' "N" "" "" "'" NW cont Table IX-Q 1 I 2 I 3 .1 4 I 5 I 6 I 7 8 9 10 I 11 12 13 14 15 I 16 J 17 l 18 19 J 20 21 "- o CI H CI HH Post 2.0 3C 2C O 20 5H OOOOO 6H 70. 20 O Post 2.0 4H Post 2.0 6Y \ Pre 2.0 30 lH O .. 30 OIOO 20 80 90 20 OHHHHH ·. Post I 2.0 -.lC lH 80 80 JC I 50 50 80 9R 5H JC 9C 7C lC Post 2.0 70 JC 51 50 I 5X 70 70 Post 2.0 6Y 8G "~ Pre 2.0 80 90 lH 60 50 & E 8G 30 80 & E 50 & E Pl ' e, 2; 0 ~ 5G CI HHHH Post 0.4 gC 9C gU gC 2C 2C LC 9C & C 5C & C. 9C 9C 9C I 90 90 6G Post 0.4 90 PrEJ 0.4 9H 90 9H 70 30 & E tC 80 9G 80 gO SG Pre 0.4 90 .1 CHa H CHs H CHa Post 0.4 Je 2G OO 8G OO 20 OI · o & C o I oo II, I Post 0.4: 80 II. Post 0.4 6F mi I Pre 0.4 O 2G lH O O 30 O O I 8G 80 O I I CI H I H N0 2 H. Post '0.4 2G O 8G 2H 2H 4G -OI sc 2C 3C ooo OI Pre 0.4 2G OO (f O 9H lC ooo. Oo Pre O / l I 7H IHIFIIII 0.4 I 3C III' 2 ~ IJ ~ I 2 ~ I ó I 2 ~ I 2 ~ I 3 ~ IIJ ~ IIIFHF Post OI ooo 3G l Pre 0.4 oooo & E CI H CI H CI Post 0.4 3C 5C 2G 2G 3H ooo JC o 2C 20 JH 3G Post 0, 4 8G '6G 6G Post -0.4 fY 2G Pre 0.4 o 4G 20 oo lH 2G 3G 4G o & E II ---------, H CJ IHHH, Post 0; 4 2C 3S lC 50 lC o O lC O o 70 & P lC lC I Post 0.4 70 80 3G 30 8G 80 5G I] - 'oc; t 0.4 6y J're 0.4 4G lC - tC o 2G 2C O 2G 8G 8R 5G 30 j Ple 0.4 70 9H; 'cont. Table IX-Q III fi .1 I (IIIIIIIIII 17. III 20 · I] 2 3 4 I 6, 7, 8 9 10 11 12 13 14 15 16 18 19 21 H CF li HH Post 2.0 2H lB lC 'O l O lC O 2C 2C' 2C lC 3 Post 2.0 3C '3C 6G 7G Post 2.0 6Y 2H 6F,, Pre 2.0 30 lC tH 4G 20 lC 2C tC 2C 3C, 4C tC \ I Pre 2.0 - 5G 2C 5G 4G.CHa HHHH Post 0.4 3C 3C 3G JC lC OO / 3G OOI 7G 2C and 3C 2G Post 0.4 6G 4H 5G 60 80 Post 0.4 6Y, 8G I Pre (0.4 O 3G 5H OO 2G. OO 70 8G 9G O / I 9U II I & c IF CI HHH Post 0.4 8C 3C 5'U 2C tc O 9C 9H 30 ~ C 9C lC Post 0.4 8G 90 9G and 9G 2H 8G 9: I Post 0.4 6Y 8G I Pre 0.4 2C 2C 2C 5G O. gH 1C O tc 2C 2C Pre 0.4 9H 9G. SH 5G gO 8G. "I - - Cfl 3 HHHH Post 0.4 9C 6C 8U 3D 6C 8G 8G & C 2C I 4G 9C 7G 2C 9G Post 0.4 90 9G 9G 9G gIl o 6F. 8G •,. Pre 0.4, 2H gG 8H 5G lC & E 'lC tC 9G 9G 9G O Pre 0.4 90 7G 9H ~ ~ ~ ..... ~ ~ = = ~ ~. ~ ~ SG 3C 8G I 9C II 9H sc I 2G 9G 9G 6C 5G I ~~ I 8G I 5H l ~~ I 2G IO j 7G I ~~ Im I 6H I ~~ IIIII 9C 2U 8G 9C 2G 2G 2C 9G 4G I 2G l 5G 5G 9H 5G 2G 5C SC 4H 2H lC 6G, 2G gC OO 4C 7G 2G O 9G 7G 90: G 8H 8G y6; 2C 2R lC 2G 2G 9R 3G 2G 3G 80 3G O 8R 7G 3H I 90 .. 3C SC 6H 7H 4H OO 2C 2G 4C SC 3C 2C gG 8G 9G gR 9G 90 7G 6G 6Y lH 50 2C 3G O 9H lC lC. 90 70 5C O 5H 7H 90 ------------ 2C 9G Pre I CHa HRHH Post 0.4 Post 0.4 Post 0.4 / Pre 0.4 Pre 0.4 CI HH ~ IH Post 0.4 Post 0.4 Post 0.4 Pre "'-. 0.4 Pre 0.4 CHa I H I H I CHa I H I PosOt I 0.4 .1 Post 0.4c.d. Table IX-Q 1 I 2 I 3 I 1 I 5 I 6 I 7 I 8 I 9 I 10 I 11 I 12 I 13 I 14 I 15 I 16 1 17 I 18 I 19 I 29. I 21 CHs I_ HIHI CHa, IHI Post I 0.4 I 6y, 7G I 201 2G 1 101 1 2G I '2G I 20 I 2G I 8G II 5G 1 I Pre 0.4 O 3G I 50 9G I 6G l I CHa HH N0 2 'H Post 0.4 8G O 8G lH 7G 80 2C 4G 6G lH 2G O Post 0.4 6F 9H I Post 0.4 7F Pre 0.4 3G 3G O 60 5G O 4G 30 5G OIOO et HIHI CH 3 HI Post I 0.4 I 7C 2H 5U 9H I 3C I 10 30 2C 9H .1G & C 9C 3C 9G Post O ~ 4 9G 4C 9G 90 80 8G Post 0.4 I 80 Pre 0.4 2C 2C 8H 2G 4G 9R 7G 2G 9G I 2C I & E I & E Ere u, 4 7G 8G 7G I Br HH Br H Post 0.4 JC 3H 6G 5G 2C 4G 2G 7G 2C tC 5H 2C SC 5G Post 0.4 gG 3C 8G 7H 9G Post 0.4 6y 9G, I Pre 0.4 3G 4G O 2G O 6G 3C 3G 9G 5H 2C o Pre 0.4. 5G I CH 3 0 HIH CI H Post 0.4 le 2H 9H I 7H I 2H 40 2G 8G 2C O 7G 5H I 3C 9G Post 0.4 9G 3C 90 9H 6G 'Post I 0.4 6y 8G Pre 0.4 lC lC o OO 7H 50 2G SO O 2C 3G. Pre 0.4 6G 4G CHsO II IHI CH 3 0 H Post, 0.4 SC 2C 2U 8G 2H 2G SG uP 8H 4G 9C 9R 2C 4C I Post 0.4 9G 2H 8G 7G 8G 7G 8G ~ Post 0.4 8G I Pre 0.4 le 7G lC 3G 6G 9H 5G 4G SG & E 2C O Pre 0.4 8G 70 I. - ~ Cl-I 3 I CH :, I H CH 3 I CH, Post 0.4 3C 3C 6G 2G. 2H lC lC 40 2C tC 2C tC JC tC II Post 0.4 gG 8G 7H SG SG, II Post 0.4 6Y I: I Pre 0.4 SG JC 31-I 3G 50 1C 2C 2G 90 O 5G 9G I ! I Pre 0.4 50 gH "" '"~ ~" "'" ~ Q ') ...... ...... ~ = ~ ~ "" "" "" "" "" ~ = ~ = cd Table IX-Q, 1 I 2 I 3 I 4 I 5 I f) I 7 I 8 I 9 I, 10 I 11 I 12 I 13 I 14 I 15 I 16 I 17 I 18 I 19 I 20 I 21 CH g H .H / CH 3/2 0H H Post 0.4 2S lH O 6H 2H OO 21-IOO 5G lH OO Post 0.4 6G 2C 5G Post 0; 4 6Y Pre 0; 4 O 3G OO, 2G O \ 4G 5G 8G 80 OO and _. II l CFs 'HR · H "H Post 0.4 & C 9C & C 9C SG 9C 6C 8G 9C, 90 I & C & C l' gG I 9C Post 0.4 SC 3 {: II 5C 6C I Pre 0, .4 9H gG '9H 9H lC & E 9I-i 9G I & E & E! 8G I 90 Pre O: 1 7G I' II 'I ------------------'-'-- - ~ - ~ - .FHHHF Post \ 0.4 gC 3C I 4C 4U 9C 3G O 2C 2C I 2C & C 9C 6C I 9C Post 0.4 80 I 9G 8G SG SG 7G 9G I Post 0.4 9G I Pre 0.4 II 2C JC 4H SG 2G & E 2C tC 8G 8G 9G 7G, Pre 0.4 9H ~ G gH 7G I I _-----: _....--: -----_- -: ..., ....: - = --__- = --_--- ..: .... -: --- ~ ._ ____: ....__ _____. .: .._ I CI HHIHH Post 0.4 9C 9C & C 9C 9C 9C 8G 8G ~ C! JC r & C & C sC 7C I Post 0.4 4C 4C I Pre 0.4 '& E & E 9H gH gG & E 9H 9G 90 8G. & E 9G ----: --- ~ ---------------- '~ - "'" "- CHsO. H CH 3 0 HH Post 0.4 tC O 8H 3G O 2G O tC 3C 2C 2C O 2C te 'Post 0.4 6y 3C' 8G 6G 5G I Post 0.4 9R 2C O 4G 5G & E 2C 4G 8G & E 2C 8G II Pre 0.4 8H I 80 II i I- 'i "~ I-' l \; l 'QCIT ab I iea IX-R Compounds o \' v'zor2e 7 '] Re R 4 R j R IS R r lr CI 2, CHa 3 H 4 HH Post Post Pre \ Pre 0.4 0.4 0.4 0.4 0, .4, gC f C gd hU ~ GJ ~ H SC f G pH S ~ sC ft · H lC 40 8G 'lC 3G lC 9C & E ~ C 9R lJ-I 9.C 5G lC 9G SG & .C 90 9C 4C 9G 4C I § 9G 7G ............ ~ = ~ = SO 3C SO 70 7G 9C SC 8G * 90 90 9C 9G 2C ~ G 90 20 I 9G 4 ~ I 2C 9G 7GI & C. 5G I 90 9H 2C 8H 2e SG SC 90 80 & E & E, SC 9G 2G o tC 5G 70 JC o 70 9H tC 9G 3C SC gO 9G 9G 5lj 9G ~ C SC 9G 6F 0.4 0.4 0.4 0.4 0.4 'Post, ~ ost Post Pre Pre H CHa HH CHa' ... .... 1 • ) li CHa HHHH Post 0.4 2H 2C 2H \ Post 0.4 rD 2H SG J Post 0.4 9G 9G i. \ Pre .. 0.4 SG l Pre 0.4 - I l 'j 9 € I rC .SC I. & E \ 9G 90 I 90 2C; 7G · ~ C tC ~ gG 6l'I gC & C 6G 9G, I. 6G & E I SIl 5G 9G! IG I 9C I SG. ------'- - I__ I__ ~ I g 5C 4C tC 2C! 'C! CI 2C I 9C I 9C I! · CI' LC ~ .G rO 3 G SG I 7l-l & E f 'H. S ~ 2C & E I 9H l' 1C 9H II BO] C 3C 7H 8G tC I 9R gR tU 7G ~ CI gU gG 9H SC lU 'gO 7G 3H 9G 6Y S'C 20 0.4 0.4 0.4 0.4 Post Post Pre Pre HHI '' Br CHsO HH Il H Br CHIO Post 0.4 Post 0.4 Post 0.4 Pre 0.4 I Pre 0.4 r J '~;' __ o _ I '.' I - ~ --- ._-------- CI CI H.CI CI Post 'Post · pre Pre 2.0 2.0 2.0 2.0 BC 90 7C rG 3U 9H 9H gC 9H SC 90 'gR 2C SO 9H SC. 9G · 2C 90 SC 9G & E ~ ..C 2C 9G 3e 8R 4C SG & C 9G' & C 9G 9C 9C 9 ~ 9Bc.d. table IX-R I 1 I 'IIIIIIIIIIIIIIII, 21 - I- I 2 3 4 5 6 7 8 9 10 11 12 13] 4 15 16 17 18 19 20 IIHHHHH Post 2.0, tS 3C 7G 2U I 3C 30 SG 3C I 2C 2C I 9C 4C 7C SC Post 2.0 '6G 9G SL 90 90 SX '80 9H SO, 80 80, Fost 2.0 6Y Pre 2.0 70 9G 90 SO SG & E 2C 8G 8G 80 70 & E. Pre 2.0 80 / CI HI CI H CI Post 0.4 3e I 6C 7R 7H I 3I-l IOIOOI 3H O SC 6C 6C 80 Post 0.4 9G. 9G 7G II 8G 90 -.Post 0 ~ 4 6Y I 8G I 2H SGI Pre 0.4 I 8H O 6G SG 40 8G 90 tC 2C. Pre 0.4 I. I, IJ 8G / I 9C I 7G CI II HHH Post 0.4 9C \ 9G 3C 7C 7C 9C & C I sc 9C & C I & C 9C I rre 0.4 tC I IC 1 9G JC 2C & E 2C 2G 90 9G 9G 7G .pre 0.4 - II 80 90 I 7G 60 I 6G II, - 30 I ~ 20 l H CI HHH Post 0.4 4C SC lU lU 2C, 4C I 2H 2G 9G. 2H 2C lC Post 0.4 6Y 6C 6G 3H 2H 8G 6G ~ 8G gO SG I Post 0.4 8G 9G & E ItH & C 'I Pre 0.4 lH 9G I 9H 3G 2G 2G 9G 8R 9G & C I Pre 0.4'; SG I 3G I mi I 2C! 3G I 9C CHa Cl-I 3 H CH 3 CH 3 Post 0.4 6C I 5C 8G IC lG 2G l; CI SC 6C SG Post 0.4 90 9G 6H I 9G I 7G 7l-I i I '8G 9G Pre '0.4 I 9R 2C 9R IO 40 & E 7H I 5G I 6.G & E 3G 9G Pre · 0.4 I 9H' II ... II le I ".. 'H CI H Cl H Post 0.4 3C JC 60 2C I 20 2G Je 2G 2G 2C 7G SC tC \ Post 0.4 4H I 4H 5G. 2H 7G '4G 70 Post 0.4 8G 7G "Pre' 0.4 4G 8G IC 8G 6G 9H 30 O 8G 90 2C O Pre 0.4 7H 70 F, HH} 'lI Post • 2.0 2C I Post 2.0 \ SH p Post 2.0 8G Post 0.4 2C 3C 9H SC 2C 30 9C 9H 2C 8C 9C 8C 2C Post 0.4 9G 9R 8G SG 80 \ "-..." "" "W looo" "" "" WN ~ ~ ~ = ~ ~ cd Table IX-R I I I I I I I I I I I I I I I 16, I I I / 19. I I - ~ - 1 2 3 4: 5 6. 7 a 9 10 11 12 13 14 15 17 18 20 21 FI HI HIHIFI Pre -I 0.4 IIII 9H I 9G I 9H I 9G j6G I & E I 2C 11C I 9G I 9G I liC lIC Pre 0.4 9H 6G ' 9G I & C I, FHHHF Post 0.4 gC SC 8U f C. SH 50, 3C 9C 8e 4C 70 3C JC l 'Post. / 0.4 8.G 9G 90 'I 7G 7G 80 Pre 0.4 2H "90 8H 9H tc & E 9RI 4C 9G • 90. 8C tC I Pre 0.4 .1 90 40 8G I 80 CI IHHH Gl Post 0 , 4 9C gC & E & C SC SC 2C 9C "& C & C 9C & C 9G 9C Post 0.4 9G 8G. 9G .- Pre 0.4 2U & H 9H & E 9R & E gH 2C 9G & E 9C & ~ Pre 0.4 90 9G II • II ----,., -, ----------_. .._-- F 'CI HHH Post 0.4 9C 9C 4U ~ C' SH SO 3e, SC 9H SC '& C 9C 9C .9C Post 0.4 ~ O. 90 ~ O 80 I're 0.1: I lu 90 9H tH tc & E. 9R JC 9G & E 9G 80 Pre 0.4 I 9G 70 60 .4G - '-, I I 8U I 3c-1 CI CI H H H Post 0.4 9C f, C SC su 9 <; 2C gC 6C 4G & C gC JC Post 0.4 9G 90 90 I 9H SG Pre 0.4 9H 1 ~~ 9HJ 8G IC I & E 2C SO 9G 9G SC tC i, Pre 0.4 60 9H 9G 7G III ol '3H I. 2 <;; ---_ o_- FH 1-1 CH 3 H Ipos t 0.4 2C 2H 6G 4G SC oo 4C SC 9C SC 2C Post 0.4 7G SC 9G 9G 9G 8G 8G 'Post 0.4 6F 9G Prc 0.4 8G 2C gH o I o 9R 2G o, 9G 2G · 9G 9G - II Pre 0.4 · 8G III • I 3C I rc I CI HHH CH 3 Post 0.4 9C SC SU SU 4C SU 3C. SO SC 9C '9C I SC Post 0.4 9G 9G 9G 8G 8G 8G 8G 9G Pre \ 9H 2C 9H 9H 9C 90 3e 0.4 & E 9G. & E & E & E. Pre 0.4 I 8G I 8G CHaO I HI I 7C I 5U I 90 I I & C 1 2C CI · H H Post 0.4 2H 2C I 4C. o '0 9R 3G I 9C 2C (Post 0.4 9D' 9H 9G 8G j. 9G 9G \ I aG Post p, 4 90 l, 9H j Pre 0.4 8H 9G o 2G & E 9G 4G 9G 9G 9G 7G IIIIIIIIIII . ..... in W ~ 'c, .. :) ~ ~ ~ ~ = = ~ 9G 2C 8G 3C 9G cd ~ ta ~ licy IX-R 90 SC 9G' 9C o tc JC 6G 2C 7H 30 3H 8G tC I 3C 9G 2H 6F 8G 0.4 0.4 0.4 0.4 0.4 Post Post Pre Pre CHa H CHa 'H 1 l I 2 I 3 I 4 I 5 I 6 rz I 8 1 I 9 I '10- I 1.1 I 12 r 13 I' 14 r 15 I · 16 117 .1 la- I 19 I 20 I, 21 3H IO. O 2C I ~ O 90 I 9G II 9H I 5G ° I 90 l O, I ·, 1- CHa ~ ~ ~ = = = ...... w (, J1 6C & E 2C 8G & E 2C 9G 9C 8G 9C I 6C EG 9C I 6C & E 9G 9 ~ 1 ~ 9G 9C 9G & C 9G & C 9C 9G 90 3C 3G tC 9G 6C 9H 4C SC I 2C & E 9H 8G 3C 2C 80 gR gH 7G c;.: E 3C & E 3G 80 JC 7G 60 'SC SG gH 6G 4H 1.20 9G !! HI 6G 9H 9G 9G 8M 6U 3H 4C & E ~ H gR 2U gH su 9G 9R 3U 9H ~ C sC 9C I ~ C 4C 90 6Y -gC 0.4 0 , 4 0.4 0.1 0.4 0.4 0.4 0.4 0.4 0.4 0., 4. Post Pre Pre Post Post Post Pre Pre Post Pre Pre HHHF CI CIJ 3 H HI ~ 0_ . _ HHHH CI I CHaO C 2 H gO CzHsO IHIH · IC 2H sO IHI, Post ~ .4 6C I ~ C 3D Je m. 1 JC 1 ('I 70 3C 2C I 9.cl l 5 ~ 6C 9G PQ8t 0.4 9G i _ sG. 8G 9C 8G i 3G. I 9H. 90 9G Pr _ ('~ 0.4! 9H gE IA} {i 70 SG _I 9I-I 9H gH. 1 gG · gG 2C & E Pre 0.41 , I,. '1. I 6G .-----: ------------: - ~ -----: --------'---- ----.--.; ---- JC I 2C I 9G I, ...... ~ = 9G lC 83. & E 90 O 9G 9C 3C 70 SG I 8H 6G I O 2C 80 8G SC 2C gH 63 9H LC 7G 9H SC 9R 9R 3C 80 9H 3C gG O 2G 8G 8G o gH. 8G 20 7H, I 6C 9G 9H 4C 4C 9G gO 9G SC 9G 90 8G 3C 9G 90 6C 9G 65 I 2H ju 90 '4C gG 6Y, I ~ GI --- --_.- o _ 9C 9C .. 9G 19G, 6C 9G 0.4 0.4 0.4 0.4 0, 4 0.4 0.4 0.4, 0.4 Post Post P: re Pre Post Post Post Pre 'Pre HH JI NO z ____ IIIIH' CHa H Post, '0. 41 1 SC 9C 3C 3G ~. 2 (} ll ~ 7C ~ CO & C 3C 5C O Post 0.4 3G SG SG 4G Post, 0.4 6Y HHHHHF CHa C.RsOc.d. table IX-H 1 I 2 I 3. I 4 I 'fi - I 6 I 7 I 8 I 9 I 10 I 11 I 12 I 13 I 14 'I 15 I 16 I 17 I 18 I 10 I 20 I 21 I CHaO IHIHI: CHa IHI ~~: I ~: ~ r II ~~ I 80 l ~~, \ 2 ~ I 3G I 7G I SC I 2G I 7G I 4G I SG I 3G CHa 'HR / CH 3/2 CH R _Post 0.4 4R 5C 2C. 9R I 3C lC lC 3C lC lC & C 5C I 2e O Post 0.4 9G 8G 9R 90, 40 90 40 50 90 • Post 0.4 6Y Pre I 0.4 2C lC SH 80 7G "9H 2C 4G 8G 9G • 5G & E Pre 0.4 9G 90 gG I -----.:.1__....:....----1....- 1 --- ..: ....-------. : ....--------: ---------- ~ --7 ___----- = ----------.,; --____ : ____-- CF, RR fI R Post O, ~ gC 9C 7G 8G I gG I 3G 30 SG gC 5G & C 8C 9G 9C Post 0.4 SU SC 2C. 2C 6C, Pre 0-, 4 SG 2C 9H 30 3G 8H 70 O 90 & E 9G 7G Pre 0.4 8G FH - IHHF Post 0.4 9C 8G. 8G 9G .: 7G I 4G 4G 7G I 9G I 6G 9C 9G! JC I Post 0.4 SU SC 2C I 2C 3C tC I SC. Pre 0.4 9H 9H gH 8G 80 & E 9H 9R! 9G & E & E & E --CI ------; - ~ HIH Post 0.4 9D 4C O 2G 2H IOO 4G tC O 4C 9C 4C 7G Post 0 , 4 9G 8G 9G 9G 7G Post 0.4 6F Pre, 0.4 ° tC SH OO 6G tC 3G & E 90 6C SO Pfe O, t ~ 7G CI HH N0 2 H Post 0.4 4S 2C 3C 2C 3C tC 70 5C 9C SC 2C 3C 3C 2C Post 0.4 8G 4H gO 8G 7G 70 70 .9G 6H 8H 7G Post 0.4 6Y Pre - 0.4 90 8G 2C 90 7G & E 9R 30 80 90 7G 5G -._- - ---- ------- -_.'- "" "'--- CHaO HH CI R Post 0.4 8D 2C 2C 9H 9C 6G 8G SC tC 5G 9C 9C te 9G Post 0.4 9G 3H 9G 9G gR Post 0.4 6Y 9G Pre 0.4 9R gG 9R 8G 8G & E 9H 4G 9G 9G 9C 4G FH 'i FH l' F Post I 0.4 4S I 2H 5G I 7H 3H oo I 3G 2C I tC 2e I 2R I 2G o I, Post 0.4 7G SC 70 7H 4H - Post, Q, 4 6Y 7G 5X II Pre 0.4 3C 2H 2e 80 o 2C 2C 5G 2e o SC 2C I, Pre 0 , 4 II 8G 9G II 9H 'I 7H I 6G I 8G I-' "'" ~ I-' ~ co ..... ..... ~ = ~ ~ l I 2 I 3 · 1 4 I 5 And 6 cd Table IX ~ RI 8 I 9 I 10 I 11 I 12 1 ', 13 I 1 ~ I 15 I 16 I 17 I 18 I- 19 I 20 I 21 CHa HHFH Post Post Pre Pre 0.4 0.4 0.4 0.4 9C 6C 9G 9H 2C 9G 9H 9H 9H. 9C lC SC 9G & E 9H 2C 9G 5C 9G lC 9H 2C 8H 3G 4G SC 9G 90 SC 9G 9G SC 7G 9C SC 9G SG CI H H 'CHaO H Post Post Post Pre Pre 0.4 0.4 0.4. 0.4 0.4 & D 2H 9G SC 9G 3U 9G LC 8H 2C 7G. 7G le 3H 9G 9H lC o 9G 8G SC 4C 3C 9G 9H 7G & E I 9R I 3C 60 9C 9G & C I 9C 9G I 9C & C & E ...... ~ ~ CI HH CF 3 H Post Post Post Pre Pre 0.4 0.4 0.4 0.4 0.4 4H I 3C It 6G I _8H 9G 3H .'6Y. 9G 8G I 7G 3H 9G 8H o 6G o SG, 9P I 6G 9G & E I 7H oo 9C 90 9C 9G 3C 9G SC 9G 9G JC 8G o H CI CI HH Post Post Post Pre Pre 2.0 2.0 2.0 2.0 2.0 3H 8G 6Y 2C 3H 8G 6G I 9H lC I. JC 60 I 90 3H 9G 2C o 60 o 2G 8G 9H 2G lC 6G oo lB 8G 9G JB 8G. 9G 2C 6G SG 3G ~ ~ ~ = ~ cc CI CI CI HH Post Post Pre 2.0 2, q 2.0 SC 9R SC 9G 3H lH 4H lC 2C 8H 2C oooo SO 4G JH lH lC o SC I gG I SC 9G 9G 9C & H lC le SG O 1 -; - 1 ----; - 1 ...... ~ = o 2C 9G SC 8G 6C I. 9C I 9G, SC 3C I 7G "9G 7G & C gH & E 9G 9G SC 9G 2C lC 2C I le 9H, 5G 9H · 1 '3C 7G I 2C 7G I & E 2C I JC SG IO BG 2C 7G SC 9G' 6G 3e o 2G 9H I 2U 9H SC 9G • • II • • 2C II 7C 2C II 9H 2C II 4G 40 II 6C 'I 9R l, 2H I & C and 6G 9G 8G 3H 9G SG 6Y 9G gR 4S 9G 6Y 0.4 0.4 0.4 0.4 0.4 2.0 2.0 2.0 2.0 I 2.0 'Post Post Pre Pre Pre Post Post,. Post Pre Pre R' HI CI CI CI H CI CI CI l'c.d. Table IX-R '1 I 2 I 3 I 4 I 5 I 6 I 7 I 8 I. 9 I 10 11 I 12 13, 14 I 15 I 10 I 17 I 18 I 19. I '20 21 CI -HHH CI Post 0.4 9C 9C 90 {) C 9C 9C 8C 8G 9C 8C & C & C 9C 9C_ Post 0.4 6C SC Pre 0.4 9H 9G 9H 9H lC & E 9H 9G 9G & E 90 9G Pre 0.4 8G - -------; - NO! HHHH Post 0.4 9C 9C 9G 9G 9C 4G 4G 4C 9C 9C & C 9G 9C & C Post 0.4 3C 7U 8G SC Pre 0.4 9G lC 9H ZH lC & E '9H 9G 9G 9G 9G 9G Pre 0.4 9G 8G .6G 9G ------ H CH 3 H H H Post 0.4 3C 6C, 7G 9H '9C O O 2C SC 2C 9C 9C 3C lC .... 0.4 7G 9G l 6G 7G 8G Post \ Post 0.4. 6Y, Pre 0.4 & E 9G 9H 8G 1C & E 2C 2C 9G 80 90 & E Pre 0.4 8G 9H 6G lo "'" ~ lo "'" lo "'" ~ N ~ ~ ~ = ~ = T ab I ica IX-S Compounds of formula 80 ..... ..... ~ = ~ = ~ ~ ~ 9C 9C 29 9G 40 6 r ', 0 ~~ G & C & C & C 9G 9G & E I 9G 9G 9C I 9C! .,; C 5G 2C LG 9C ~ C 9C & C 2C 9G 8G & E .9G 9H & C gC & C gH 2C 9G 9C I 9G I - I "I & E 6C 9G te & C I f C 9G & E 9H I JC 9G 4C 9G & E & E 3C JC SG tC 6G. TC 8G Je 8G 9H gC I 2C 9G 9G I tc, §G SC 8G 3C 7G 8G 7G 5H 9G 2C 4H 9H 9H, 9H & E & C I ~ C & E I 9H & C & C & C & E. 9G 9G gU 9G tC 9G 9U 9G 8U 9G 2C SG 9R gC 9C 9C 6C 9G 4C 9G 6Y 9C 9C 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0/4 0 , 4 0,, 4. 0.4 0.4 .0.4 Post Post Post Pre Pre Po.st Poat * Pre Pre * Pre Pre * H Post Post Pre Pre HHHHHHHHH CI R a F 'CI CHa & C I sc I "'__, __'__, __' .__ __, _ _, ___ 9G · 1 9G -. - .. I 'EC pc 9G & E ~ as • ...- 4 ro s ::. ~ / Ro ca ~ C,) ~ II', '....' ~ .a 0 · ...- 4 o ~ i \, 1 in,:; .H ~ R 7 ..o 8 ~ ~ ~. ~ ~ E.b · S ~, ~~ l ..o ~ I ro ~ tj ~ o 5. · S..c: ~ ~ ~ ~: 0. ~ Ro ~ I rn o ..c; ... ::: o ro ~ b.O ~ ro Q) c; ~ c :: J ~ ~ ~ .1 '"" ") o I g ~. ~ bJJ ~ ~ ro ~ :: J · 0, ~ oZ. ~ oC ro ~ E o ~ ~ ~ UJ. ~ H ~ ~ ~ co UJ ~ (f) ~. ~ ~ uS; ~ ~ ~ ~ bC (), --- - --- ----- - ---------------- -------- --------- ------------ ') 3 4 5. 6 - 7 8' g. L ° 11 12 13 14 15 16 17, 18,] 9 20 21 I -, l., .. 9C I- '"... ~ o 3G SC pG 6G ~ C gC & C 9G lC 70 ~ I 9G 9C le 80 4G sG ~ C 2C 2H 9G 2C 80 tC 6G lG, ~ G '3q 2C 9H & C Je 90 & E & E le & C Il ;; 2G tc 5G SC 2C 8G 5G & E 9R 3H 9G 3H 5G 60 9G 9H & C & E tC 8G gR '& C 91-I 7G 8H 9C 2C 2H 90 5H 9G 6Y gC 0.4 0.4 0.4 0.4 2, 0 2.0 2.0 2 .0 2.0 Post Post, Pre Pre Post Post ·, pr) st Pre Pre HHHHH CI CI, .. CI H CI:;: CI:. 7G • IFHH CH ~ II Po '; t Post 0.4 · 0.4 gC 9C 2C 8G 9R 6C 9G te tC 9C 2C 8H 4G 5C 90 & C.l SC 8G ~ C 6Gl F 1 2 1 3 I 4 1 5 1 6 I - I ~ IHI CH. I H I ~~: I 7 0.4 0.4 8 9 continued panel IX-S 3H 3C I 2G 8D 3H 9G 9G 9H I 8R 7H I 3H 9G & E IO ..... ~ ~ & E 8C QC 9C 2C I 9G 9G 9C 9C 9G 9G SC 9H 9C 9G 9C oo 2C SG 9B o I 7G I 7H 2G I & E I 6G 83 8G o tC tC 2G SG 2C 9G 3H 9H 3U 9G 9H tH 7U 9G & E 6C 9G 6C 9G 0.4 0.4 0.4 0.4 0.4 0.4 0 , 4 0.4 Post Post Post Pre Post Post Post Prvv HH CF 3 CH 3 0 HHHH CI CI CI CI CI CI H CI CI H CI HH Post Post Pre Pre Post Post Post Pre Pre 2.0 2.0 2.0 2.0 2.0 2.0 2.0 2.0 2.0 2.0 SC 9G 6y SC 9G 6y ~ C 9G SC 9G tc 8H SG 6H 3G ~ HI SC 9G tC I 7H 6G PH SC 9G tC 9H 8G ooo 3G o 1.7GI SG I 6G o I 6G o I 8H tC SH 2H tc 7H tc oo tC 2G & E.I 9C 9G I 9G 4C I 9C 9G 9G I 9G 3C SG SC 9G SC 9G 7C o 2C 8G o ~ ...... ~ = = ~ CHa IH 'LI 9C I SU 9G 9R (C tc 9G 9H 2H 8G,. G, C 8C 9G 9G ..... ~ 0 \ SC 8G 8G 9C tC 9G 9C 9G 9C 9C & C I & C 9G I 9G I & C I 9C 9G I 9G 8G 8G 7G 9G 2H 6G 2C 8G gR [oC 2H SG 2C 6G 9C 9H SC 19G! -IG I & E 9H & E 9C 6C 9G & E lC 4G tH tC I 9H I SG 8G 9G 7G 2H 8G SC 9G 9H 6C 9G gR 3e 9G 9H SC 9G 9G 9C 9G & C 9H II & E & C 3U 9G tc 9G 8 C 9G 8C 9G SC 9C I 9C 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4. 0.4 0.4 0.4 Post Post Pre-Pre Post Post Pre Pre Post Post Pre Pre HH HI H CI CHa HHHH CH 3 CI "CIc.d. tabUcy IX-S __1_1_ 2 _ I 3 1 4 1 5 1 6 I 1 7 1 8 I 9 I 10 and 11 I 12 I 13 I 14 I 15 I 16 I 17 I 18 I 19 I 20 I 21 I - Br H lI Br H Post 0.4- 9C 9C mi 8C 5C 40 50 4C 9C 7H 9C & C 8C tC Post 0.4 90 9H 90 90 80 Pre 0.4 9R I 90 9H SO 90 & E 9H 60 90 90 5C 70 Pre 0.4 90 I CHaO H CHaO li H Post 0.4 9C 9C 9U & C 5C 90 4C gC gC 2C 5C 5C 9C 90 Post 0.4 90 90 90 90 9.0 90 Pre 0.4 gR & E ~ H 9H 2C & E 9H 70 90 90 9C SO Pre 0.4 9H & C I - CI CI II CI CI Post?, O gC sC su rC 90 9C SC & C 4C & C & E 9C Post 2.0 90 90 7H Pre 2.0 & H & E I 9H 9H 9H & E gH 3C 90 90 9C 3C Pre 2.0 QO 90 CHaO IHH CI H Post 0.4 9C 6C 90 '90 SC SO SG SC se 2C 9C & C 9C o I Post 0.4sG 90 SO 9G 70 I Pre 0.4 90 90 - 9H gH Je & E gH 70 90 90 gG 80 Pre 0.4 70 I CI HHH CH 3 Post 0.4. 6C 6C SU gU & C se SC SC I 9C 9C & C & C 9C gC Post 0.4 90 90 90 90 80 Pre 0.4 9H & E 9H & E 2C & E I 9H 9H 90 90 8 0 & E Pre 0.4 SO I, 'FHF 1-1 F Post 0.1 2C 2C 2C 90 3H 20 o 4G 3C 2C 2C SC I o 20 Post 0.4 90 4H SO 80 80 70 9G Post 0.4 6Y SO Pre 0.4 2C 2e le 60 o 9H 3e 50 70 20 o 90 Pre 0 , 4 I 9G 90 80 CI H CI H CI Post 0.4 3C 3C 7H SH 2H ooo 2H 20 se 6C 40 SO Post 0.4 90 90 SO SO 90 90 Post 0.4. 6Y Pre 0.4 7H 70 3H 50 oo SO 40 90 90 o & E CEla H CHa HI CHa Post I 0.4 2C I 5C 3H I 40 2H OOI tC OIO 90 I 5C 60 I 5C Post 0.4 90 90 90 90 90 90 90 II Post 0.4 I 6F IIII l "" '"~ ~" "" ". ~ ClIO ~ ~ ~ = ~ = 1 CHa 2 IHI 3 CHa 4 HI 1'5 I ~ 6 Pre Pre 7 0.4 0.4 8 9 I 10 I 11 I 12 I 13 I 1 ~ I 15 II ~~ I ~~ I 9H I 5G I 5G I 9H I 16 O ~ ~ ~ = = ~ 9G 7G & C & C 9C 9G 6G 9G & E BC 9G I 9G 9C & E 9C & C 9C gC 9H 2C 9H 9C 6G 6G 9G lC lC SC tC 7G & E 6G SG SC SG SC SC 9H 2C & E SG ~ CI & E I gC & E I & E I 9H 9G & C I 9C SU 9H 2C gR 9G ~ C 9C 9C 9C 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.1 Post Post Pre Pre P'Ost Post Pre Pre CI HHHHHHH CI CF 3 l '. I _, - = - 1 9G 9C gC 9C & C 9C & C & E 9G 9G & E & E & E 9C 9G 9G f, C 9C 9G & E 9C 9C 9H 9R SC 9C & E & E 7C SC 2C ~~ IIIII ~ 7G I = sC HC 9C 9C 9H 9H 9H 9H 9G 9C 9C & C gC & E 2C & E & E 9C gC SC 9C 0.4 2.0 0.4 2.0 2.0 0.4 Pre Pre Post Post Pre Pr! ~ HHHH NO! Table IX -T Compounds of formula 81 rn ro Q) ro ro ro ~ ro ~ CJ ~ '2 ~ N o • ...- 1 o ~ R a R 4 R 5 R 1 X tIl ro "O ro ~ $ -I • ...- I. ~ ..o ro ro ~ ~ CJ ~ ~~ ~ ~ .. ~ ro NQ) ~ '8 U) U) Q) cu ..o ~' CJ ~ .....- 4 CJ o ~, .. c: ~ o tIl ro: 0 'a ro $ -IU) oo ro ~' 0.0 ~ ~ Q) CJ ~ ~ ~ ~ ~., ....., oo tIl 'u) - tIl N $ -IN ~ · NQ) tIl ..o ~ o ..8 ~ ev $ -I ~ o ~ · 0 Ul (5 ~, .. c: "O ev $ -I o N ro U rn ~ H .!: l ::: ~~ CO Ul ~ rfl ~ ~ U. ~ p .. ~ r :: L o =. ~ ------ -------------- -------- -18-1-] 9- ---- l 2 3 4 5 6 7 8 9 10 11 12 1.3 14 15] 6 17 90 21 CI HHHC 2 H s O- Post 0, 4 2H '2C 9H 2C SC lG lG SC 9H 6G 9C 4C SC 2C Post 0.4 9D 3H gH 9G 9G 9G 9G 7G Post 0.4 9G 9G Pre 0.4 6G 9H 9H SG SG & E 2C 2C 9G 3C 9G 9G Pre 0.4 9G 9G JHI IHHH ~ H CH 3 S Post 2.0 lH O 2C 2H OO 2G JC JC SH SH 2C O Post 2.0 8G I 8G 3H Pre 2.0 7G 6G 8H OO 9H 4G O 9G 9G 9G SG CH 3 HHH CH 3 S- Post 2.0 SC 4C 3G SG SC OO 5G I 6G SG SC O lC OI Post 2.0 9G 9G 9G 9G SG Pre 2.0 2H JC 9H 3G 2G 9H I 8G 2G 9G 9G 9G 7G Pre 2.0 7G 9G IIHH .HH nC 3 H 7 O - Post 2.0 3C SC 2C JC 2C 3G 3G 2C 3C 2C 2C lH 3C 3C Post 2.0 9G 9G 8R 9G 8G 7G 8G SG 8G 7G 8G Post 2.0 6Y Pre 2.0 lC 9G 8H '9G 8G & E 8G 4G 9G 9G 9G & E Pre 2.0 9G HHHH / CH 3/2 CHO Post 2.0 3C 2C 2C 2U 3C 2G SG 3C SC 7G 9C 8e 2C 7G Post 2.0 9G SD 7G 9G 9G 8G QH 7H. Post 2.0 6Y 9G Pre 2.0 9H 9G 9H 9G 8G & E 9H 8G 9G 9G 9G & E CHa HHH / CH S / 2 CHO Post 2.0 9G 8C 2C 2C 9C 2G SG SC SC 3G 8C 9C 9C le Post 2, 0 90 9G 9H 9G 9G 9H 7G Pre 2.0 9H 9H 9H 9H JC & E 2C 5G 9G 9G 9G 9G Pre 2.0. 8G I 9H ..... en .......... Ol N ~ ~ ~ = = ~ cont. table IX-R 1 I 2 I 3 I 4 I fi I 6 I 7 I 8 I 9 I 10 I 11 I 12 I 13 I 14 I 15 I 16 I 17 I 18 I 19 I 20 I 21 CHa HHH nC SH 7 O- Post 2.0 9C 7C JC 5U I 9C 5G 30 3C 2C 2C 9C 9C 3C tC Post 2.0 90 8G 9G I 8G gR 80 80 Pre 2.0 gH 9G gH 90 80 & E 2C 5G & C 90 90 & E I Pre 2.0 gH I ...... ~ ~ ...... ~ lliiIio ~ ~ ~ = = ~ T ab I ica I ~ -U Compounds of formula 82 R a R ox (tS 2 .o (tS -o ~ tr.loom ~ O rJlt; (tS "C,) ..c:" m I, .gd I - I ~ (tS. ~ m · m N ....- 4 C,) o ro tI.l N r, j H ~~ m. E OJ ~ ro ~ o llO $ -lo UJ. ~ N "C ~ $ -l :: 1 ~ :: 1 ~ m · 0 rJ: J. ~ C,) · S OJ N tI.l c ... fi) (1). ~ O ~ ..c: C,) ::: 1 a .I '~. ~ CtS ro c C,) c. ~ o C f-4 ~ ~ fi) u: l te o ~ C ..c: 'OU. ~ ~. ~ ~ ~ ~ u: lm .8 ~ m f-4 ~~ = 0 ~ o 0-4. .s :: Cl) · a Cl) N ~. ~ u: lm ~ rn ~. o '~ QU ..... <.n. tli CI H CH s OCH 2 - Post Post Pre 0.4 0.4 0.4 9C SC 9G 5U 9G gR 9C 9G 2C 9G 9R tC 6G 9H 2C 6G 7G SC 9C 9G & E I 9H 2C SG 7G SC SG 9G gC 9G se "9C 9G I & E CHa CHaO H CHaO CH a OCH 2 - C2H 5 0 Post Post Pre Pre Post Post Pre 0.4 0.4 0.4 0.4 0.4 0.4 0.4 6C SC DG 9G 9C I 3C 9G 2U 9G 9R 2C SG 9H 3C 9G & E 2U SG SG 9C gR 9C 9R 3G 2H SG tC 7G SG SG tC SG lC 6G 7G SC SG & E 6C 9G & E 9R gH 6C SG gG lC SG tc 4G 7G 5G 5C 8G 9G & C 9G 9C 9G 8G 5G 6C I 9C 9G & E & C 2C 9G 8G 3G ~ ~ ~ = = ec ~ C ~ C 4C j 5G 9G 8G 3C ~ BG 9C 9G 5G JC tC 7G 9R 9C 7G 3C & E 3G 5G C2H s OH CI Post 0.4 I 9C I 9C I 9G I 8G I 9G Post 0.4 5U 5U SH III:;.: ~ :: ": 9H 9G, 9H 5G 5G CHaO CI \ .C2H 5 0 Post Pre Pre. 0.4 0.4 0.4 0.4 9C 4C 9G 4U 9G lC BG 9G le 9G 3C 9G 9H 6G BG 7G 8G 4C 7G & E gR 9H BG 4G 9C 90 ~ c 6G BC RG 5C 7G 5G 9G ... ..CI1 Q) CI CI C2H s O Post Post Pre Pre 0.4 0.4 0.4 0.4 7C 9G 6C 9G 7G 'lG aH 9G 3R BG aH 5G IO fiG I 4G 2C 7G & E 2C gR ~ C BG 3G 5G 9C 9G 2G 5G 5C 8G 6C 2C 9G 7GT table IX-V Compounds of formula 83 ~ Ol ~ xz cd a, o cd 'o ~ CI.l OO Ul Po! About UJ. ~ Cont ..c: bo ~, c .; 'CI.l O; ::: J cd ~ tf.l cd cd NI "" "" "l c .; O cd tf.l N CiS H ~~ cd ~ Q) ~ cd ~ o bO H o UJ. cd N "O ~ H; j ~ ::::: 1 ~ cd · 0 UJ. cd c .; · A (L; r - ..: tf.l Pi tf.l (]). ~ O ~ ... t = c .;; i · N ~ ~ cd cd ~ c .; ~ ..... o ~ H ~ ~ tf.l tf.l cd o ~ ~ ..c: "OU. ~ ~ ..... ~ ~ ~ tf.l cd .8 ~ cd H Pi ~.: 0 ~ o Pi, ~ (]) · A (]) N ~. ~ Tf.l cd ~ co H o, o () t-ol t-ol ~ = ~ ~ SG 2G 2C 7G 9G 9G I & C & C 9G o 2G gH 2C gH & E 9C 2C 2G 2G 9H 9C 9C 9G 9U 9G 9G ·. 6C 9G 6C 9H 0.4 0.4 0.4 0.4 Post Pre Pre CHs CHsO I 3G II CHsO CHsO Post Post Pre 0.4 0.4 0.4 9C 6C 9G. 2U 9G gG 9H 9G SH 9G 9R JC 4G lC 3G SC 9G & E 2C 7H 6G oo & C I & C I SC 9G 9G I 9G 9G 2C 9G O CHs CHs Post 0.4 ~ tB tC Post 0.4 2H 2H Pre 0.4 9G 8G 'Bre 0.4 3G 2G lH o 2H 9G 2H oooo SG 4H oooo 3H 9G 6G 9H 8G tC 2G tC SG O ~ Ot 00T a table IX-W Compounds of formula 84 & C lIC 7G IC 7G & C I & C I 2C & P 8G I 8H 8G R s H x CHsO Z CHsO ro '8 ..o ro' o ~ U) oo Y1 ~ o U'J.1i; Post Post Pre Pre ro ... e bil ~ 'CJ, U) .8 H 2.0 2.0 2.0 2.0 ro ~ U) ro ro N -' CJ o ro U) N CIS S-4 ~~ & D 6Y ro ~ Q ) ~ CIS ~ 2C gG o bJ) S-4 o UJ 9G ro N '"O ~ S-4 :: s ~ :: s ~ f; G lU 9G CIS' 0 CI ) 8R 9R ro. ~ L :: Q) NU) P-4 9G 7G fI.l Q). ~ O ~ ... e CJ :: s G 3G 'N ~ ~ & E ro CIS ~ CJ ~' .- 4 o ~ ~~ fI.l U) CIS o ~ ~ ... e "OU. ~ ~ '.-4 ~ ~ ~ U) CIS rE ~ CIS S-4 P-4 ~: 0 ~ o o. .., ~ Q) 'a Q) N ~. ~ U) ro ~ ro S-4 o ..o U 2C 8G & E "" "" ~ l ~ CI CI li CHs CHsO CHsO CHs CHsO CHsO Post Post Post Pre Pre Post Post Post Pre Post Post Post Pre Pre t 2.0 2.0 2.0 2.0 2.0 2.0 2.0 2.0 2.0 0.4 0.4 n, 4 0-, 4 0.4 5S 6Y 7G lC 3G 6Y 2H 8G 6Y SC 7G SR 3C 9G 8C 9G IC 40 2C 3G IH lC 9G 2C 9G IC 'I. 7G 3G 2C le I & E SG IC 2C 4G 2H 60 I 8H 9R I 9C 2C I & E 9G 3G oo 2G o ° oo 2G 3G 2G 7G 3C 7G 6G 9G 9C & E IG o lG 2G 2C 9R 2C aH 4G o 2G 2G 6G lC 6G 4G lC 4H SC 9G 9G 9C 9G 9C IC 9G 6C 9G 9G BC 9G 9G 2G 2C 4H SC 7G 7C 9G 6C 9G 4G 3C tC 8G & E 9C 6C 8G "" "" ~ Q ~ ~ ~ = ~ ~ IR CHs CHsO Post Post Pre Pre 0.4 0.4 0.4 0 ', 4 9C 9G r; C 9G 8G 9C 9G gC 90 5G o 2C 4G lC 9C BG 9C 9G le 7H 2C BG te & C I 9C 9G I 9G 9C 9C tlC 9G 2GT table IX-X Compounds of formula 85 I- '= "" "" x CHaO with CHaO cU · 8 ..c ~ ..o ~ m OO 00 ~ O m. ~ CF.Post Post Pre ro ..c: --- bO ~ ..u '00 ..s 1--1 0.4 0.4 0.4 ~ + J 00 ~ ro N _l UO ~ 00 N ~ H r "': J _ ~ 4G ro ~ a :; ~ ~ o: J f C 9G O '0.0 H o Ul 2G 2G ~ N' "O: .H :: s ~ :: s ~ o ~ G ~ .'0 m 4C rG rH co u 8 Q) N Ul p-. o o m Q). ~ O:. ..c u .2 O o o · N:. o ::: at 40 -II ~ ro ~ U ~ • ....- 1 O ~ H + J + J mm ro O ~ ~ ..c: '"OU .9J. oo ~ • ....- 1:. ~ ~ M ro ~ ~ ro H 0-.} ~ O 2G: '0 ~ O ~ 4C 9G, ~ Q) · a Q) N o ::: 5C 4G. ~ M ro ~ LC 3G ro f ... 4 O, .QU 5G & E ~ ~ ~ Q ~ = CH s CHaO Post Post Post Pre 0.4 0.4 0.4 0.4 2C 8G 6Y ~ C 7G 5G I 20 5G I 6G 2H tG gH ° 4G o 2G 20 9R 2C 2G o 2G & C 9G 5C 9G 8G 2C 70 2C aG 9G "" "" ~ NT ab I ica IX-y Compounds of formula 86 R s Re x ro oS ..c ro ..o ~ u :: loou :: l ~ o rn. ~ ro 'u ..c:' CI.l -. o '0.0 ~~ ro ... oj ....,;} u :. ro m N - U o ro u :: l N ~ H ~~ ~ ro c Q) ~ ro ~ o '0.0 H o (/ 2 ro N "O ~ H :: s ~ :: s ~ ro · 0 r.fl ro u c Q) N CI.l Pt U'J. (]). ~ o ~ ..c: u :: s 6 · N ~ ~ ro C \ S ~ u ~ • ....- 1 o ~ H ~ ~ .CI.l CI.l ro o ~ c : ..c: "OU. ~ ~ • ....- 1 ~ ~ ~ u :: l ro ~ ~ ro H Pt ~ ~ ~ o P-4, ~ Q) · a Q) N ~. ~ u :: l ro ~ ro $ -to ..c D "" '"O) w & E 9C I 8U 9G 5C I 3D 9G gR 9H I gH I 9R ~ ~ ~ = C') =" "'" O) ~ gC & C 9C 9G & E & E IC 8G 9C 9C 9G 9G 9G & E 3C 9G gG 5C aG \, & C I 9C gC I 9C & E I 9G & E I gG 9C 5C & C 9H 6C 3C 9H 8G 91-I 9H & C I 9C 9H I 9R 5C 7G & E & E 3C aG & E 4C 8G 3G 2C 6G 8C 3C 2C aG 2C 5G 7G 5G lC 8G 9G 5C I gC 8G gC 9C 9H 9H 9C! LG & E 9U 9G cU 9H gR 9C gH 5C 9G 2C 8G 6Y gC f C 9G BY 2.0 2.0 2.0 2.0 0.4 0.4 0.4 0: '1 0.4 0.4 0.4 0.4 0.4 Post Post Post Pre' Post Post Post Pre Pre Post Post Pre Pre CHa CHa CHaO HH NO! CI CI CHa114069 25 -I Compound of formula 10 ~ 1/32 9G I 1/16 9G 30 Compound of formula II 110 "1/32, 9G9C. Compound of formula I- I 87 1/32 .. & C, i5 -; bundle pattern ~ II 135 1/32 aG Compound formula I (I 124 1/32 & G & C lG ~ bundle of formula 112 1/32 9G7C 1/16 9G7C 165 arvensis) 7 cm high , canine dill (Eupatorium capillifolium) with a height of -3 cm and wild buckwheat (Po lygonum convolvulus) with a height of 6 cm. The above-mentioned plants were treated prior to emergence with the same solutions. The trials were carried out in a greenhouse and the results were evaluated 4 weeks after the treatment. These results are given in Tables XIII-A and XIII-B. Tests for the control of tibia (Cyperus rotundus). In 10 cm diameter pots filled with Fal1sington's pollen loam soil, 5 cyperus mare (Cyperus rotundus) were planted, placing them about 2.5 cubic meters below the surface of the earth. Four types of trials were carried out with these compounds, namely before the emergence of plants, they were sprayed on rhizomes - cyprinids before planting, they were introduced into the ground to a depth of 2.5 cm and the leaves of plants were sprayed when they reached a height of about 8- 10 cm. The test compounds were applied as solutions in appropriate solvents in an amount corresponding to 560 liters of solution per 1 ha. The effects were visually assessed 4 weeks after. The results of the trials are given in Table XIV 'Trials of Selective Control of Taurus in Cultivation. In a row of plastic materials with a polyethylene lining, having a diameter of 2 cm and filled with dusty-clay soil of Sington Fal1, seed on corn (Zea mays), soybean (Glycine max.), Was placed at a depth of 2.5 cm. rice (Oryza sativa), cotton (Gossypium hirsu tunl) and tiger mare (Cyperus rotund '. ~ s). The test compounds were dissolved in appropriate solvents and sprayed before and after the emergence of plants in an amount corresponding to 560 liters of solution per 1 ha. After emergence, the plants were treated when they were 6-14 cm tall. After 4 weeks from. the treatment assessed the plant's reactions visually. The results are given in Table xv. Tests for controlling water plants. The test compounds dissolved in a non-oxic solvent for plants were sprayed on the small b ': - ~ sows in which the water hyacinth (Eichornia crassipes) was grown. The tests were carried out with plants 25-30 cm high in a greenhouse and the results were evaluated after 4 weeks have passed since the procedure. The results given in Table XVI show that the agent according to the invention is also suitable for the control of aquatic plants. This Table XVI I Tests with water hyacinth Test compound Amount of plant reaction kg / ha hyacinth l 2 3.I. Compound of formula II 132 '1/32 · 9G I Compound of formula I' 134 1/32 9G2C 1/16 9C Compound of formula 1/16 I 9G 136 1/8 9G 1/4 I 9G4C 1/2 9G4C. 10 15 20 45 50 55 60 65 166 l I 2 I 3 Compound of formula I l. 120 1/32 9G9C. Compound of formula I 138 I 1/32 9GIC 1/16 9GIC - Compound of formula 139 1/32 9G 1 / 16 9G -. Compound of formula 1.40 1/32 9G5C 1/16 9C Z'viclzek of formula 141 1/32 9G 1/16 9G2C III - Compound of formula 142 1/32 9G I Compound of formula 143 J 1/32 9G Attempts to regulate plant growth. Resources we ~ ilug. the invention, in addition to potency to combat: undesirable vegetation can also affect. favorable for the growth of some species of plants. Usually, amounts of funds are used to give 0.01-1.0 kg of active ingredient per 1 ha and the time of treatment is selected depending on the plant species, in order to obtain the desired results, with minimal toxicity for plants. In this way, both reproductive and vegetative development can be regulated. 3 types of trials A, B and #C are described below, in which the reactions of sugarcane, sorghum, bahia grass and other grasses were tested, and the agents according to the invention. In the case of sugar cane and so.rgo, "chemical maturation" is achieved, which manifests itself in a greater yield of dissolved substances and solids, mainly sugars, contained in the plant. In the case of other grasses, the inhibition of growth and stalks is observed, which reduces the movement requirements. These measures are also included in Table X. Pre-emergence use on Fallsington's dusty clay soil ~ ~ o H ~ :: sc: .J 7H 7G 7G 18G 7G IIO 7H 8H o 5H I 5H I 5H I 5H 3H 6G, III 6G I 7G I 8G I 5G 8G I · & C 4G ° 7G 5H ° 8G 5H 3G 8G 5H 5G 20 ~ c: .J ~ rn rS H ro ..c = '- bD ~ Test compound 00 IIIIIIII ro eu I l' CI) o ~ ~ ro ~. ~ bD ro c: .J ~ ~ ro ~. ~ § at 8 years. N ro. ~ Ro z :: N '0 ~ .B b Ul ~ .S ~ ~ u ~~ ~ ~ ~ ~ ~. ~ ~. ~ N ~ Ul UJ E CI) '0: a o H ~ CI) ro ro o CI) ..... rn c: .JN ~~ 'NI ..... ~: g ro ~ o ~ c: .J: g ~ rn c: .J] ~ ~' a ~ 8 ~ 'N ~ o. ~ ~ 2 ~ 2 'O ro ~ ro 1 "" "" 1 ~ ~ .§ H ~ ..... .9. ~. o "3 HQ) ro .o" O "O ~ rJ) ~: -t 'Ul C). ~ ....' NN 5-1 ro H..c :: o .- N tt ~ o NN. .... ~ (J) 'o ro, ... lo .., ", rn -' N o ~ Ul :: s P-4 ~ U. ~ en. O Q P- P- Ul ~ O ~ en. UH. ~ ~ ~ EJ ;: ~ ~ "O en. ~ Pt CQ 1 1 1- ~ -1-3--4--5 -, - 6--7- -8 - g-.1O -1 -1- '-} - 2- --L3-1415-1tl 1718192021222324251 5 Compound II, • Formula 87 I 0.06 ~ ~ ~ = ~ ~ 9G I 9R 9G & H I 4G 8G I & H IOI 9H I 8H I 2G I & H 9C 8H 7H I 5H I 5H I 9H & H I & H I & C I & C 8C 9C 8G 9G I 8G I 6G I 8G I gG - I 9Hi & H I & C I 7G & C I 80 I & C I & C 5H 8G & C 9H 9G & E & H I & H 2G 5H 8G 3H 7H 5H 7G 8G o 7G 3H 9H 9C & H gG 5H 8H 9G 8G 5H 5G 0.25 0.06 0.03 I 8H I 9H I 8H 'I 2GI 7H I 8H I 8H I 4H I & H I & H 18G I & H I 6G II -__ --_ O "._ ....-.-..- --- I 80 7G I 50 I 5H & C 3H & C I 6G. '".. Compound of formula 88 0.12 8G 8H 9H 9H 5G I 8H 9H 8H 8G 6H I & H I & H 3H & H I 7G 8G & H'I 8H 9H & H & H 80 5H 9G I 9G 8H I 9H 4G I & H 9G 0.25 I & H l & H I & H 3G & H & E 9G 9H & H I & H 7G I 7G 3C 5H SG BG 9H "" '"(7) oc & C 3G I 5H 5G 2G 8G I 9G l I & E 9H sH 90 I 8G tC & H I 9C I 9C & H I & 11 80 I 8H SG & C I 8G & H & H I 8G I & C I 6G 8H 8G I & C I & C & H & C 3G I 8R I & H 3C 6G 9H 5G 9H 6G 8R 5G 5G 3H 4G I 3C 6G 4C 8G 4C 2C 8G I 6G 0.12 0.50 I 9R Compound of formula 89 0.50 4C 1 gC 6G 4C I ~ C 8G 7G I 6C & C & C I 9C I & C I 8G I & C 4H I 9C I & C I gC I 5C I 8H 7G I 3G I & Cc.d. Table IX-Q 1 I 2 I 3 I 4 I 5 I 6 I 7 I 8 I 9 I 10 I 11 I 12 "I 13 _L_ ~~ I ~ __ 1 ~ 6__ I __ ~ 7_1 18 I 19 I 20 I 21 I 22 I 23 I 24 I 25 Compound 9G BG 8G 5G I BG 9G 9G 5G BG of formula 90 0.06 5G 3G ° 8G 6G & H & C & E & C 7G 7G & H O 9G 9H 8H 3H 5H 5H SE 8C 9C 9C I 0 , 25 I 7G I & H I BG II 8G I 6G I 9G I 8G I & H I & H I 9G I & c I 5G l & E I & c i & c I & c I & c I 8G I 8G I & H 1 2G, & C II aH IIII 9C I / IIII Compound I 0.06 I 2G 7G 8G aG 7G 5G of formula 91 O 4G 5G O ° 50 3G 5G aG & C 7G 4G aG & C 7G o 9G l 3H aH 5H 5H 5H I, 8G 8G 6G and 7G 7G 8G I 8G I 0.25 4G 3G 2G & c I BG & C & C & E & C 9G & C & C aG & H ° 9G aH aH 3H 3H 5H III Compound 5G 5G 5G aG 7G 9G 8G formula 92 0.06 6G 5G 2G 5G 4H 3H 5G & H 6G & H & H & H 9H aH O 8H 5H 2H 5H 5H 5H 9H aR. 7G 7G 6G 5G 7H aG aG 9G 9G 0.12 aH 3G 6H 5H 8H & II 5G & H 9H 9H 8H 9H 3G 9H 3H 7H 3H 3H 5H 5H 5H 8H 9H 8G 8G 6G aG 9G 9G 9G 0.50 9H 6G aH 8H 6H aH & H 8G & H & E & H & H & H 4G & H 5H 8H 5H 5H 5H gH 9H "" "~ c: .c" "'"' l ~ ~ ~ ~ = ~ c. = Table XI Treatment of entrust hni land of foliage ro 00 ~ ro ~. ~ ~ ~ ~ (.) ~ ~ eu ro ~ "'0 • ..- 1 oS o ro ro o' ..- 1 ~ ro (1), ~" ~ ~ ~ ; .J ..b (.) (.) N ~ "" "" 4 • ......, ~, ~ ON (1) ~ N ~ ro 00 tIl 0.-4 • ..- 1 ~ ; g 2. ~ ~ 'o ~ .E "' O 'a :: s ~ ct1 S ~ o 5, ~ -5 ~ '00 N Ul ~ ~ (.) Q) ClY (1) ~ ~ ~' N ..o p. c N o ~. ro (1) ro ro o :: s • ..- 1 'N N :: s ro ~ ~ 0 ..- 1 ... t ::: ~ Ul ~, .. :: ... at N UJ. ~ o: l ~ ~ ~ "'O ~ ~ ~ ~ ~. U U. ~ ~ t: 0 UJ. -4--5--6--7-lll-g-1O -} - I- - 1-2-} 3- ~ -1-5- --1-6- -i7- ~ 1-8- --1-9- 20 & G I & C I & G I & G I SG I & G I & G I & G I 9G I 3G I 5G I 5G III 5G Test compound 1 Compound of formula 93 Amount kg / ha 2 0.06 ct1 '0 fil. 3 ~ 8C 9C 9C 6C 8C 2C 2C 5C 5e aG o 2C BC 2C 2G 5G 3G 3e. .... ~ ..... & 0.1 & G I & G I & G I & G I & G 1 & G I & G I & G 1 --- 1 --- 1 --- 1 ~ __---- .: - - = - ...: .....-__--- = - 0.12 9C 9C 9C 7C 5C ~ C 4C tlC 6C 9G 9C 4G 2G 2C 80 EC 5G 3C 4G 5G 3C 3G 5G 3C ~ "" "'" ~ = = = ........... N 90 3C 80 o 70 7G o 5G 6G 4C o 40 80 5G I & G 1 & G I & 3 7G 5H 511 gO 5C 3C & G I & G 40 1 5G .. 1 80 5G 3C I 9C I 4C 5G oo 50 2G o 3C 8C 6C 6C & 0 I & G 6C 7G I & G 7G. I & G 2C I 9C gO 5G 6C I 6C 9C 9C 7C 6C & 0 1 & 0 4C 80 7C 8C gC 9C & 0 1 & 0 & 0 I & 0 I & G I & 0 I 8G & C Be 7C 8B 6C & G & 0 1 & G I & G I & 0 l & 0 I & G I & G 1 & G I & G I 90 & G I SC I 9C 1 & 0 0.06 0.50 0.06 0.25 0.25 ~ - ,,; ~ ia WZiOTze 94 Compound of formula e 95 3G II & 0 III 'II 60 I 3G I 4G I 20 40 o 80 II 9B I. I! JC I 9C I 9C I 9C I 9C I 2C 3C I EC. I and. & G I & G I & G I & G I & G I & G I & G I I & G I 7G I I I & 0 I & G I I. I 70 3e 3C 3C 2C 30 2C 60 5C oo lOB I 2C 2B '50 3G 2B 8G 2B 3B 40 80 SB 7B 7B 5B & G I & G I&G I ---. 1 --- 1 --- 1/1 1 1 1 1 1 1 1 1 1 II ~ I, _ 0.12 Compound of formula 96 & G I & G & G I & G 8G 1 & G 1 & G 2H i 3e 7H 5G I & G 3e 3e 3G 2e 80 3B 6G 5e 5G 5G 7G I 5H. & B 7B 6B 4B 7B "5B & B eB 5B 0.507G oo O o OOO table XI 10 I 11 I 12 I 13 I 14 I 12 I 16 I 17 18 1 19 I 20 II fiG IIIIII 6G 2 O, f 'tl, 13141_5_16171819, I & 0 I & 0 I & 0 I 30 I 60 I 30 I fiO 1 Compound of formula 97 4B 5C 7C 2H _____ 1 1 1 1 1 1 1 --- 1 --- 1 --- 1-- -1 --- 1 --- 1 ---' ---'--- 1 ---' ---'--- ~ ~ ~ = ~ cc 5G 4H I 5G SG I SG 3G O 7G O 4G I 2G 3G SG 7H 6G 7G 5G 3H 4H I 3G O SG I 4G 5H o 3I-II 6H & G I & G 7H I 5H I 7H I 7H I 6H II 5H I 3H II 5H I 6H III 5H I 7H I & G I & G, I & G I 5G jl lOG I 3G II OIO II 6C! O lo! OIOI 3G 4C SC SG 7C 5G & G & C 5C 7H I 7H i & C 51-1 '1 6H I 4H I 5H I 3H & G & G I SG I & G I SG I & G 7H & G 7B & G 'I & C f 0.50 0.1 ~~ 1/16 _____ 1 1 1 1 1 1 ---- 1 1 1' 1 1 '--- 1 --- 1 ---' --- '---'--- Relationship about pattern from 100 Compound of formula 99 & G 1 & G & G I 7G SG I 7G 1 SG I 5G II 0.25 I 5G OOI 5B I SC 7C I fiC 3C I 3C I 2C I 2H II 2H I 2C I · I 2H I ~ Compound of formula 98 II & 0 I & 0 I & 0 II & 0 IIIIIII · III 0.06 I --- I SG 6G & ~ I 6G I 3G OIOO 4G IOOIO 6G 4C ZC 5C 4C I 0.25 i :; --- 1 -: -; - 1 -: -; - 1 -: -; - -: -; - I -: -; - I - & - GI --- 1-5-GIO-1-2- Gi- 3 - G -I-6-Gj-2-GIO-1- 0 -ISG- ------- ~ --- · ~ I ~ I ~; J & 0 l 60 I 60 I 50 I so II 70 IIII & 0 III & 0 I 70 ----- 1 --- 1 --- 1 ----- 1 --- 1 -__ 1 --- 1 --- 1 --- 1 --- 1 --- 1 --- 1 --- 1 ---' ---'--- 1 ---. --- .--- 1/4 & G & C & G I & G & G & G SG & G & G 3G OIO & G SG 7B 9C 7C 6C 9C 5e 6C 9C 7C 3C O 4G O 3G 1/16 I - & G- --4-G - & - GI-4G- -4G- -4G- -7G- -50-- --- 0- -0-1-0- -5G- -SG - 0--0--0- -7G- ________ ~ 3_c ~ I_ ~~ _ · ~. I ~ I ~ I. And .. ~! li Compound of formula 101 1/16 & G 4G & G I 4G 1 4G 1 4G 1 7G I 5G 3C 2C 3C 2C 2C OOO 5G I 8G fiG O o O 7G ----- 1 --- 1 --- 1- --1 --- 1 --- 1 --- 1 --- 1 --- 1 --_. ---. ---. --- .--- 1 --- 1 --- 1 ---' ---'--- 1/2 l / SI & 0 i 60 I & 0 'I 50 I 60 I & 0 I SOI 70 I 40' 50 I 40 i OI 50 I 70 IO i 30 OI & 0 I ~~ I ~~ I ~~ I-- ~ I ~~ I ~ --I ~~ I ------ ~ & G & G I & G 6G I & G & 0 I SO 70 I - 6G I 6G 4G I SG 9G -I 70 8G 2G 6G 7C SC SC 2C BC 5C 3C 5C 2C 2C 3C 3e ~ ~ ~ = = ~ "" "" ...: t O ') "" "" ...: t C11 cd table XI 1 t 2 I 3 f 4 I 5 I 6 I fi I 8 I 9 :: / 5 I 10 I 11 I 12 I 13 I 14 I 15 I 16 J 17 I 18 6 I 19 I! version 1. 02 & G 7G & G SG 8G & G & G 60 60 80 8G 0.06 SG - O 2G JG 3G 60 5B 3C 9C BC BC 9C 6C 2C 2C 2H 3C -------------- ---- ---------------- & G & G & G & G & G & G & G & G & G 60 3G 60 6G & G 0, 25 & e 3G 6G 3G 3G 6B se 9C 6C 6C 7C 4C 5C 3C 3C 2C 2B 5C & G 7G & G I Compound of formula 103 & G & G & G & G & G & G 0.06 & e SG 5G 3C SG 2G 3G 2G SG 7C 7C 9C 7C 4C 7C 9C 3C 3C - -------- ----- ------------------ - & G & G & G & G & G 9G 9G & G & G & G 0.25 - & e & C & e 7G 7G & G 6G 7C 9C 9C 9C 9C 6C 6C 5C ,, 9C 8C I - Compound of formula 104 & G 5G 5G & G & G & 0 6G 0.06 7C & G 8G 5G O 4C 5G EG OOO SC 3C 2C 3C 8C SC 5H ------ --- - ---------------- ---- ----- & G 4G & G & G & G & G & G & G 0.25 9C 6C & e - & e 4G 7C 3G & G O 9C 3C f C 7C 7C 7C 6C I SR Compound of formula 91 & G & G & G & G & G 7G 6G 6G 0.06 8G 3G 3G OO 7C 2G OOO 7C 7C 9C 7C 8C 3C 5H 5H ---- --------- --- ------ ------------ & G & G & G & G & G I & G 7G SO & G 0.25 SG & e 5G 3 G 3G 7C 4G 2G 5G 7C SC ~ C f C 5C 7C 3C 3H 7H Compound of formula 88 I & G. & 3 I & G & G I & G & G I & 0 & G I & G 9G I 5G I 5G I 5G I 6G ~ I ~ I 2G OOO 0.06 8C SC 9C 6C 4C SC 6C 8e 5e 3e 2e 4e ---- -------- & G & G & G & G & G & G & G & G 90 40 9G 5G 7G 0.12 & e & C OO 3G 4G 7e 7e 6e ge 6e 6e 6e 8e 3e 7e 4C 5e ------------------ ------------------ & G & G & G & G & G & G 70 & G 9G 70 SG 9G SG 0.50 & C 4G I 2G I 6G I 7G I se I 9C I 7e 6e I 8e _se I 7e 3C I 9C 5e 6C 6e I 6ec.d. table XI '20 SG 2e 19 4G o 18 17 2H 16 3H 7G 15 2e 3G 14 4G o 13 12 6G SG SG 2e 7e & G 7G SG 3e 7e se & G 6B & G 2 I 3 I '4 I 5 I 6 I 7 I 8 I 9 I 10 I 11 II & G O, O ~ Compound of formula 87 l ....... ... .... ... QO 2C 4G 5e oooo 4C o 4G 2e I 2G 2H 3H 2G 5G oo 5e o 2G se 7C 6e 7C 5e 6e SC 6c 6e 3e & G I 9C ge &::; I & G & G I & G 9G I 8G I 9G 7G 9G I 7G I 2G 4G 9C I 6C SC I 8e I 4G SC I 8C 2C 6C I sc I sc ~ ~ I & G I SG I & G I & G SG IIOI 3H IOIOIOI 4e I ~ OIO: »~ I ~ sc Ile I 5c I 2e I 2e 6C 3e 5e I · ge ~ C l [c 5c & G & G & G I & G I & G. I & G I & G I 7G 3C I 3C 6e I 9C & G I & G I & G & G I & G I SG I 4G I. 7G II 6G 2G 2C ooo 6C I 9C I 4C 7e I 7C I 7e I 3C I 3H III 2C I & G I & G l & G II 6G & G I & G I & G 5GI. I 8G I I 2G 3G & G I I o o 3G. o - o 6e I 8C I 7C I 2C EC. 2C. 6C 5H. . 3H · I 2C '~~ & G ~~~ - & G.I & G ~ I-- · - ...- · - ~ ------ ~ & G I ~~ I ~~ --I ~~ I ~~ II-- ~ I ~~ I-- '--I: - I ~ & e. O 3G O · 4G 6B I 8e ge I Se 6e I 4e 3e I ge 2e I 4e I 3e SH I I I I 3e - & G I & G I & G I 6G I SG I 8G I & G l & G I &::; l 9G I 8G I 6G II 9G II SG OO 3G IO 3e I 5e I 5e I se I 5e I se se 3e 2e II 3e -7G & G ~ & G- ~~ - ~ I '- ~ - ~ - 7G 4G 5G 5G - IO 0.25 0.12 0.50 Compound of formula 106 Compound of formula 105 0.06 8e I 2e 6e 7e. ---- & G & G & G 7G 0.1 ~ 5e se 7e 3e -------- & G & G & G 9G I 0.50 I I I 501 6e ge I ge Compound of formula 9! & G I & G & G & G 0.06 SC SC SC 6C ------- & G & G & G & G 0.12 SC 9C 9C 7C --------- & G & G & G & G I 0.50 III 7e gC gC 7C179 114 069 Table XII-A 180 I Pre-emergence trials Amount Clear- One- Test compound kg / ha Wheat Deaf Stoklosa Stoklosa not one year old roof oat Rye field ryegrass l 2 3 4 I 5 6 7 8 Compound of formula 107 1 / 32 OOOOOO l / In OO oooo 1/8 ooo 3G 1G 1G Compound of formula 108 1/32 2G 4G - 8G & C 9C 9C 1/16 2G 5G 9G & C & C & C 1/8 8G 9C & C & C & C & C Compound of formula 109 1/32 OOOOOO 1/16 OOOOOO 1/8 - OO 5C 4C 2C Compound of formula 110 1/32 OOO 4C 5G 5G; 1/16 OOO 4G 5G 5G I 1/8 O 1C 1G 7G 7G2C 6G2C I Compound of formula .111 i1 / 32 OOO 1G 2G 5G 1/16 OOO 3G 3G 5G 1/8 b 1G O 5G 7G 8G2C Compound of formula 106 1/32 OOOOOO 1/16 OOO / lG 1G O - 1/8 OOO 5G 6G 6C1C Compound of formula 112 1/32 1C O 5G 5G 8G 6G1C 1/16 2C 2C 8G 8G 9G 9C l / H 3C 1 ') "" 9G 9G3C & C 9C.:' - 'Compound of formula 113 1/32 O 1G1C 6G 6G 7G1C & C 1/16 O 3G1C 6G 7G '9G2C 9C 1/8 2C 4G1C 8G 9G 9G & C. Compound of formula 114 1/32 1G 5G 8G 9G 9G & C 1/16 1G 5G 9G & C 9C & C 1/8 2G 5G 9G2C 9C 9C & C Compound of formula_ 106 1/16 - O 4G 9C 80 & C I 1/32 4G O 8G 9C- 9G & C / 8 4G O 8G I & C 8G & .C. Table XII-B Test compound Compound of formula 108 Compound of formula 107 - Compound of formula 112 Compound of formula 106 Number of kglha 2 1132 ~ / 16 1/8 1/32 1/1 l 1/8 1/32., 1/16 118 1/32 Attempts after plant emergence I Clean - One - Wheat Deaf Stoklosa Stoklosa not a year old roof oat rye field zycica I 3 4 fi 6 7 8 lG 4G I 7G 9G 9G6C 9G5C 1G 5G I 8G & C & C 9C 1G 7G 9G & C 9C 9C OOOOOOOOOOOO 1G OO 3G 5G 3C '0 O 2G 6G 8C 8G 3G 1G 5G aG & C 9C 3G1C 1G1C 8G3C I 9G & C 9C 1G o 5G I 8G3C 7G & C181 114 069 182 cd Tables XII-B 1, 2, I ~ I 4 I - 5 I 6 I 7 I / 8 1/16 1G 2G 8G 9C 9G & P 1/8 1G 2G I 9G2C 9G3C 9G ~ C Compound of formula 110 1/32 OOOO 3G 3G. 1 / l6 OOO 2G 4G .5G1C 1/8 1G 2G 3G 5G 7G 6G Compound of formula 111 1/32 O 1G O 1G 3G 6G, 1/16 1G OO 2G 4G 7G 1/8 OOO 6G 5G 7G Compound of formula 113 1/32 1G 3G 6G 4G 8C 9C 1/16 1C 3G 6G 7G & C 9C 1/8 3G 4G 9C 9G I 8C 9C WZOI = ze 114 1/32 O 2G 6G 7G 8C 9C '1/16 lG 3G 9G 9G SC 9C 1/8 2G 6G 9G 9G 9C & C Compound of formula 106 1/32 OOOO 1G 3G, / 16 OOOO 2G 5G 1/8 OOO 2G 2G 6G Table XIII-A Pre-rise tests (Ij ~ (Ij ( Ij o tI.l ..c: = · a CJ, Q) CJ ~ ~ (Ij N Amount. ~ (Ij ~ CJ ~ Test compound "O · N ~ ~ ~ $ -4 $ -l ~ o ..s :: o Q) 5-l kg / ha (Ij (Ij (Ij Q) · al :: = ~ 'oJ) o .. "cJ)' CJ ~ tI.l tfJ · aoo · s ~ (Ij .. ...- 4 o ..c: ~ ~ ...... o (Ij ~ (Ij Q) CJ N +: - 8 o .. ~ ~. N r8 oo CJ. ~ :: s U) · N .I "" 'l · NU) ~ ~ ar ~ & U) p .. t) UJ. UJ. ~: 21 Q ~ O ---- - - - 4 1 1 3 4 5 6 7 8 9 10 11 12 Compound of formula 112 1/16 OO 7G 5C 3G3C & C & C & C & C 9C 1/8 IG "2G 7G 8G 3G3C & C & C & C & C & C 1/4 3G 2G 8G 8G 3G3C & C & C & C & G & G 1/2 4G 2G 9G 9G 6G3C & C & C & C & C & C Compound of formula 106 1/16 OO 'OOO 8G 9C & C ~ C 9C 1/8 OOOOO 8G gC & C 9C 9C 1/4 1C - OOO 9G & C & C 9C 9C 1/2 1C 20 8C' 2G O 9G 9C. & C re 9C - I Compound of formula 113 1/16 O 4GIc 7G 70 4G 9C 9C & C 9C & C I 1/8 O 4GIc 7G 7G 4G & e & C & C 9C & C 1/4 2C 8GIC 9C 8G 6G & C 9C & C 9C 9C 1/2 2C 8Gle & C 9C 8G & C 9C & C & C & C Compound of formula 117 1/16 2C 3G 4G 6G 2C 9C & C & C & C '5G 1/8 3C 7G - 8G 2C & C & C & C & C 8G l 1/4 3C 7G 5G 8G 4G2C & C & C & C & G 9C l 1 / 2 4C 7G 8G 8G 5G2C & C & C & C & C 8G useful for regulating the growth of broadleaf woody plants and herbs. 6n try a A. Dwarf sugarcane plants, 6-8 months old and 3-5 stalks 1.5-3 m tall, were grown in pots 25 cm in diameter and treated with a solution of the test compounds (2 pots per compound). At the start of trial 85, and at the end of trial, each stem was measured to the highest visible base of the leaf to allow the plant to grow taller. After 5 weeks After the procedure, the reed was cut, its juice was extracted and its content of soluble solids inside it was determined at its top, middle part and bottom part. Wy-183 114 069 184 Table XIII-B Attempts to be found ro I ~ ro o ro Ul ..c: oS o OJ o ~ ~ ~. ~ Ro ~ N Number C,) ~ Test compound ro 'oN ~~ kk ~ ~ g / ha ro o ro ro ~ o ~ o OJ ko ~ Ul tI.l OJ oS o ~ '0.0 ~' 0.0 oS ..c: oo Os a) ro .....- l ro o ro: ; a ~ 0.-4 o ~ OJ o ~ N ~ 8 P4 ~ ~ .N :: 1 oo C,) OJ ~ tI.l ON 0.-4 0t :: J tI.la ~ ~ C]) " ~ ~ & rn ~ UJ. rJ) I-; lo ~ Q Compound of formula 112 1/16 OO - 2G O & C & C & C & G & C, l / B 3G - - 6G O & C & C & C & C & C 1/4 4G 3G - 8G 30 & C & C & G & C & C 1/2 4G 4G - gO 3G5C & C & C & C I & C & C - Compound of formula 106 1V16 OOOOO & C & C & C & C & C & C l / BOO - 20 O 8C & C & C & C [C 1/4 OO - ~ GO 9C & C & C & C & C 1/2 OOO 5G 2G & C & C & '3 & C & C II Compound of formula 113 1 / 1f5 IOO 6G 8G 20 & C & C & C & C I & C 1/8 IO 3G 6G 8G 20 & C & C & C & C & C 1/4 O 3G 90 BG 2G & C & C & C & C I & C 1/2 2G I 60 & C & C 7C & C & C & C i & C & C I! I Compound of formula 117 1116 O 2G 70 7G - & C & C & C & C & C l / BO 2G I 7G 7G 20 & C & C & C & C 7C 1/4 O 30 70 70 2G5C gC & C & C & C & C 1/2 3G 8G & C sC 4G5C & C & C & C & C & C I Ta blica XIV Tinea treatment and reaction after 4 weeks Under the surface - On the rhizomes and In the ground on I Test compound number kg / ha of the soil on the surface - depth On leaves after pre-emergence soil 2.5 cm before emergence before collection I Compound of formula 118 I 1/64 5E, 7G &, E & E 5C ,, 7G I 1/32 & E & E 9E, 9G &, CI 1/16 & E & E & E & C l / B . & E & E & E & C 1/4 & E & E & E &, C Compound of formula 119 1/32 1/16 1/8 1/4 5G 7E, 7G BE, 9G & C 5G 7E, 8G 9E, 9G 9C BE, BG & E 9E, 9G & C 5E, 6G & E &; E & C 10C 10C Compound of formula 120 Compound of formula 123 Compound of formula 122 Compound of formula 124 Compound of formula 121 I 1/8 & C & E & E & C 1 ------- ----- __E_4 __-- = --- & _, E _---,: ---- & - E ------.,; --- & - E ----: --- - & - C ---, I 1/32 OOOOI 1/16 3G 6G 7G 3C, 3G l / B 9E, BG. BG BG 9C I 1 / ~ 4C 5E, 5G 7E, 7G 2 9E, 9G 10E IDE ._ ~ I ~ - 1 1 // 8 4 5E, 8G SE, 9G 9E, 9G 7C, 7G 7E, SG lOE IDE 7C , BG I 1 / 1'-6 --.:...---- 3G ------- = ---- 7-G ----: ------ BG-- ---: ---- 1-0-C - 1 l / B BG 8G 8G 10C --I Compound of formula 125 1 / :! 5E, BG 9E, 9G IDE 7C! 10E 10E IDE 10CTa b l i c a XV Treatment plant reaction after 4 weeks ~ ~ ~ = = = to- 'QO CD ... QO en After emergence I'. Soybean I Ryz I Cibora 10 11 12 1 2H I 1G IO ~ 7H, 3G 3C, 4G 6G I 4H, 5 ~ 1 3C, 5 ~ I 5C ~: 7G 7H, 7G 5C "7C ~ & C I & C 1 7C, 8G I 6G & C 8C, 8G 5C, 7G 1 4H, 4G IOI 1G 5H, 5G 1G 4G -I - & E 1 2C, 3G I lG & C 3C, 30 6G -I & JC I 1G I 8G & C lG 8G I & C 1 OI 7G & C O 8G. & C IO 4C, 8G &, CO & C & C 1e & ~ C & iC 2G & C & lC 2C, 2G & C & C 2C, 3G & C SiC IO 3C, 7G & C O 4C 7G, \ & C O 4C, 7G & C O 4C, 8G & C lG 5C, 8G 9C, 8G 1 OI 2C, 7G & Je, O 5C, 7G & C 3G 5C, 7G & C 2G 7C, 8G & Je 3G 7C, 8G GGGGGGGGO 5H, 5G 5H, 7G & C I '30jCl I Ryz I Ci ~ ra -I 4 5 6 IOIOI 5G 1 9G lG 7G & iE - 1 I 1G 7H, 8G & E I 5H, ~ 3G 8H, 8G & E II .. 8H, 7G. 8H, 8G .1 & E 8H, 8G & H & E OIOIO LG 3G & 'EIII 7H, 6G 2H, 5G I 8G 9H, 8G 5H, 7G 9G Compound of formula 129 Compound of formula 130 Compound of formula 119 Compound of formula 128 Compound of formula 127 Compound of formula 131 1.O , O ~~ IO -1-- 0 'I ~ OIOI & E IOI & c 0.16 1G 1G o,' 0 2G O '& C. Compound of formula 132 I 0.015 2G IOO 1G I 9G I 2G I 2H, 5 0, 63 2G OO l'G & E 2G 7H, 7 0.06 2G O 1G 2G & .F ':': 2G 8H, 8 0.1 ! 5H, 6G lH 8H, 8G 5G & E 2G & C 0.25 I 7H, 6G ~ H, 1G I 8l-I, 8G I 5H, 7G & E 5H, 6G & C 0.5 8H, 8G 2H, 3G I 9H, 9G 7H, 8G & E 6H, 6G & C ---------- = --------_-------.: _---- Compound of formula 133 0.25 I 1G OI 2H, 2G 4G I 8E, 9G IOI 9C, 8 0.5 2G 2G 7H, 6G 1H, 6C ~ 9E, 9G O 9C, gl 7G 2G 9G, 8G 7H, 7G & E 2G 9C, g 2 7, H , 8G I 2H, 7G 9H, 9G I ": 'H, 7G &; E 1G & C 4 7H, OC 2H, 7G 9H, 9G 8H, 8G & E 1G & C Compound of formula 1311 0.015 OIOIOI 2G I 2G I 1G I 9C , 8 0.03 1G O 1G 4G 9E, 9G IQ 9G, 9 0.06 3G 1G 1G 6G & E 1G & C 0.12 3G Il 3G 5H, 6G 5H, 7G & E 1G & C 0.25: 5H, 7G 3G 7H , 8G 7H, 8G & E 2G & C187: ---- <00 every rci --- more every 1--114,069 lB8 the figures given in the handle XVII prove that the logs treated with the measure according to the invention had a greater soluble solids content, and their growth was smaller than in the case of plants only with water containing 0.2% of the Tween 20 surfactant preparation, without the tested active substances. Table XVII Contents of the cans. Tested Amount c :; ~ stalks compound kg / ha rJJ o Isro-I Wie- ~ N D'l. ~ o deccholek Compound of formula 144 0.25 15 18.2 17.6 11.1 1.0 9 18.3 19.0 14.6 Compound of formula 145 0.25 15 18.1 18.9 13 7 4 1.0 6 19.9 20.4 15.8 Compound of formula 112 0.25 3 19.9 20.2 16.8 I 1.0 4 18.8 19.9 16.6% Only and only solvent - 40 16.7 13.8 6.1 P r o l 'a B. Plants of sugar sorghum of the Tracy variety, grown one in each pot with a diameter of 15 cm, were sprinkled with the tested compounds just before hatching. The effect was visible after 3 weeks after the procedure. Four weeks after the treatment, the plants were harvested and each of them was divided into 3 parts (lower, middle and apical) and the percentage of soluble solids was determined for these parts. treated with the agents according to the invention, this content was increased and growth and flowering were inhibited. In this table, under the heading "Reaction after 3 weeks", the symbol F stands for delayed flowering. Table XIX Number Reaction after Inhibited- Test compound kg / ha after 45 days of clot development in% Compound with 0.03 2G JO formula 139 0.125 2G 30 I 0.5 3G, 2U 90 1.0 3G, 2U 100 Compound with 0.008 2 l G ° I formula 145 0.03 3G 3iO 0.125 9G, liC, 2U 95 0.5 9G, 2C, 2U 95 0.008 2G 70 Compound o 0.03 7G 70 formula 134 0.125 & G, 2C, 2U 95 0.5 & G, 3C, 2U ~ oe189 114069 Table XVIII 190 Value of soluble solids in% of the tested compound Amount kg / ha Reaction after 3 control attempts in sections of weeks dyg Dół I Middle IWierZ; hOlek \ 1 2 3 4 5 • Compound of formula 146 1.0 9G .. F .. 2lX 114 132 69 / 4.0 9G, F 115 1 ~ 8 Compound of formula 135 0.03 9G, F, 3X ~ 19 99 84 0.5 & G, F, 3X '119 1119 112 Compound of formula 147 1.0 8G, F, 2X 114 140 96 Compound of formula 139 0, i25 & G, F, lC lr9 109 88 2.0 & G, F .. 122 115 66 Compound lJ formula 93 0.5 9G, F, 2X 111 100 57 2.0 & G, F, 2X 118 105 59 Compound o pattern 148 0.5 7G 115 106 ~ 98 Compound of formula 143 0.125 9G, F, 1C 139 1115 140 0.5 9G, F, 2C 147 129 146 Compound of formula 149 0.125 & G, F 1'13. , t13 114 I 0, .5 & G, F! 120 113 121 Compound of formula 150 0.125 & G, F, lC 127: 127 136 0.5 & G, F, IX 127 127 136 Compound of formula 151 0.25 & G, F 120 120 121 1.0 & G, F 120 120 1 ~ 1 I 0.25. ~ Compound of formula 152 & G, F 120 113 10 i7 1.0 & G, F 113 113 10'7 Compound of formula 153 0.5 6G , F, 2X --- l 122 - ~ 'Compound of formula 154 0.125. 9G, F, 8X ---- and 130 - .. 0.06 Compound of formula 155 9G, F, 2X ~ 139 - Compound of formula 141 0.06 & G, F, 2U ---- 4 1 '63 - Compound of formula 156 0.06 & G, F, 1C ~ 165 - Compound of formula 136 0.25 O - 122 - Compound of formula 134 0.03 & G, F, 2X 119 112 116. 0.125 & G, .F, 2X 135 III 105 0, 5 & G, F, 2X 126 117 108 Compound of formula 125 0.125 .5G, F, 2X 116 107 101 0.5 8G, F 115 107 113 2.0 8G, F 118 107 113 Compound of formula 157 0.125 8G, F, 3X 128 123 118 0.5 9G, F 143 124 105 2.0 9G, F 127 111 132 Compound of formula 158 0.125 & G, F, lC 127 124 12fi 0 , 6 & G, F, 2C 120 113 79 2.0 & G, F, 2C - 133 '12O 114 Try a G. Bahia grass plants (Paspalum no tabum, Flugge), grown in 13 cm pots, were dusted with the test compounds just before the 60th emergence, when the plant height was about 35 cm. For each of the tested compounds, 3 pots were allocated and the plants were dusted from the top with solutions corresponding to 560 liters / ha. The corresponding content of the active ingredient is given in Table XIX, which also shows the results observed 45 days after the treatment. These results show that the agents according to the invention retarded the growth and inhibited the development of flower beds. Selective herbicidal properties test. Selective properties of herbicidal agents according to the invention were tested according to the invention. 191 eJUlA ~ esolJ {olS 00 I v \ O eM-Ot [: H ~ pesolJ {olS 00 I v ~ sa! Mo At [JnlD 00 I :: soo I .P "" l ~ J! Ua'Zsd CJ '00 .a 'N Ci OI ~ ~ 9MOd Cj OO) O') I 00 P-4 --- ~ UUOllsOupa ~ OOIO ~ J1U1SeM.qJ 0 ') 0') \ O - - JJ {sl} ode ~ ~ AH 00 OI AM-OJl} eZsaJw ~ AH 00 '1 - I' 8! UlA ~ -eSOlJ {OlS OO, li ") t '- eM-ot [J-ep esolJ {ol S 00 V) \ O SalM-O At [: nlD 0 0 ~ e Q) .P "" l '0 ~ CJ -eJJuazSd '00 .Ci) N ~' "C r9M-? d 00 OQ) ~ \ ON J-4 P-4 euuollsoupa ~ Ou O -eJ! Uls-eM-t [;) \ O O ') li ") .IJ {sqode ~ ~ AlI 0 0 O ~ AM.oJl} -ezsalw ~ AH OO ~ li ") I CIS I ..c :: -... ~ co ~ C '\ I ~' l" "" "4 -... M '; ::;' l" "" "4 - ... 'CJ' f "" "" l '00 OP "" "" l 1--1 ~ (1) N ro- 'f "" "" l. ~ R- o O)' f "" " "l N (1) (1) ~ N · N s :: J-4 $ -4 m O o" O. ~ N m '~ r: Q ~ o ~ ~ Q) (1) NN ro- ro- . ~. ~ NNO d Ciu 00 ~ 114 069 192 in such basic crops of plants as rice wheat. The research was conducted I? Before and after emergence of plants sown in pots, a stack of jac solutions Tested compounds, an toxic solvent for plants. Two compounds were used in the tests, constituting the active substances of the agent according to the invention. One of these compounds (compound of formula 101) was used for an intermediate mixed rice; Japanese rice, one-sided weed (Echinochloa crusga} Ji) and morning glory (Ipomea sp.), while the second (compound of formula 97) with regard to the above-mentioned plants and wheat, the deaf sheep (Afena fatua), the roof pileus (Bromus tectorum) and the rye staple (Bromus secalinus). Plants were grown in a greenhouse and visual inspection was performed approximately 3 weeks after treatment. The results are given in Table X) {'. Patent claims 1. An agent for combating undesirable vegetation, characterized in that, in addition to at least one surface-active substance and / or a solid or liquid solution, of the active ingredient contains at least one new N- (heterocycloamino-carbonyl) -3rylslllf1onam-id-o, general formula 1, vV wherein R is the group of formula 4 or 5, in which formula, or X is Hydrogen, chlorine or bromine, methyl, alkoxy, 1-3 carbon atoms or methoxy, and Z is methyl or methoxy flooflick, R 1 is grl.l'pe of formula Ba, where R s ~ is a hydrogen, fluorine, -chlorine or bromine atom, an alkyl radical with 1-3 carbon atoms, a group of 1-3 carbon atoms, methoxy .. lpv or trifluoromethyl, R 4 is a hydrogen atom, a fluorine atom, a chlorine atom , brO'mu, methoxy or alkyl group of 1-3 carbon atoms, or R 1 represents the group of formula 7, where; mQ ': represents S-atom and R s represents a hydrogen atom, and W in the formula 1 'may be in a free or salt form suitable for use in agriculture. 2. The measure according to claim A process as claimed in claim 1, characterized in that the active ingredient is N - [(4-methoxy-B ... methylpyrimidinyl-2'-amino'inoco, VbonylJ-2-chloro benzene-1sulfonamide). 3. Sr'Odek according to claim The method of claim 1, wherein the active ingredient comprises N- [14, B-dimethoxy pyrrinidine10-2H-a'minocavbony10] -2,5-dichloroX'-benzenesulfone'mlide. 4. A measure according to claim A process as claimed in claim 1, characterized in that the active ingredient is N - [(4-methoxy-B-methylpyrinllidine 10-2H-aminocarbonyl -] - 2-methylbenzene-sulfonamide). 5. The measure according to claim According to claim 1, characterized by. that it comprises N - [(4,6-dimethylpyrimidinyl-2 / -aminok'VQ.onyl0] .- ~ -thiophenesulfonate as active ingredient! d. 6. The measure according to claim A process as claimed in claim 1, characterized in that as an active ingredient: a N - [(4-methdxy-6-methylpyrinidin] 10-2H-aminocetboolyl] -2-'chloalkyl-5 ... I-methoxybenzenesulfonamide. 7. The measure according to claim 1, characterized by the fact that the active ingredient is N - [(4,6-dimethyl pyrimides: nyl-21-aminocarbanyl] -2,6-dichloro-benzenesulfonamide. 114069 193 194 45 20 40 25 10 30 of R 4, R s or Re must be hydrogen, or R 1 in formula 1 is a group of formula 7, where Q is' oxygen 'or sulfur and R s' is - hydrogen volume, methyl radical or chlorine or rhodium atom, or R 1. stands for the group pe of formula 8 or g ', while in formula 8 the constants R g and R l0 are the same or different and denote hydrogen atoms, .m · e1ty, lorvie, .atom1Y radicals of chlorine or bromine, and W in for formula 1 means: oxygen or sulfur atom, with cZ-Ylm W and Q. may be j ~ dlllalkQlw or different and the compound of formula '1 may exist in free or in form salt suitable for use in x'olnictvtie. 17. Measure for the control of damaged nasal plants, characterized by the fact that, in addition to '00', the least one surface substance is active and / or solid or solid l "o" The thin-walled active ingredient comprises at least one new N- (hetero-cyclo? minocarbonyl / -aryl? sulfonamide of general formula 1, in which R &lt; RTI ID = 0.0 &gt; 3 &lt; / RTI &gt; 4 or 5, in which X represents an atom of carbon or methylthio or bro'mu, rhodium, and k-methyl, al, col {1sylO'wy ', 1 to 3 atoms, carbon or methylthio and Z is the radical. methyl or met'olxyl, then R 1 denotes a group of formula 6, in which R a and Re are the same or different, and l denote hydrogen, fluOTU, chlorine, bromine, and iodine atoms, alkyl and alkoxy radicals o. 1-- -4 carbon atoms, g: nitro roups, tr6 j uoromethyl, cyano 1 or groups with WZOIf, le CHsS / O / n- or 'CHsCft ~ / O / n-, k; 1 or 2, R4, OZ! The number of hydrogen atom, fIU OTU "chlorine, bromine or a methyl radical, R & denotes a flu atom oru ,. chlorine or bromine or a methyl or methoxy radical, 35 R 7 is a hydrogen atom, fluo:, u, ~ hlor, lUD, bromine, or an alkyl radical of carbon, where at least one of substituents R s,. R "" R 6 and · R 7 is other than hydrogen and at least of the 2 'R s, R "" R 6 and. R 7 must be hydrogen atoms · and when both substitute R s. R a and R 7 are hydrogen, then at least one of the R or R 6 substituents must be a hydrogen atom or R 1 in the formula 1 is a group of the formula 7: where Q is a sulfur atom and R s is a radical . methyl or ", chlorine or bromine atom, or R 1 represents 8 or 9, where in" formula "8 R g and R 10 are single or different and represent hydrogen atoms, radicals / methyl, chlorine or bromine atoms, and W in the formula 1, meaning, for the oxygen atom or: sulfur, with W and Q may be the same or different and the compound of formula 1 may exist in free form ~ j or in the form of salt suitable for use in agriculture. ~ 8 ~ Agent for regulating the growth of plants, characterized by the fact that in addition to one substance on the surface The <active and / or solid or liquid solvent 'comprises: o the active ingredient of at least one new N- (heterocycloam-inoclaT'bonyl / aryl sulfonamide of the general formula I, wherein R stands for a group of formula 4 or 5, including a group of formula 4 or 5, including: a hydrogen atom, a chlorine or bromine atom, a methyl, ethyl or alkoxy radical, or 1-3 carbon atoms, ... pedigree ~ k tr6j: fluorometers- 50 60 85 8 '.. The agent according to claims A process as claimed in claim 1, characterized in that the active ingredient comprises N - [(4,6-dimethylpThymilidine10-2H-aminocarbony10] -benzenesulf'Ona-, midamide. 9. The measure according to claim A process as claimed in claim 1, characterized in that the active ingredient comprises N- [i4-mephoxY-6-methyl-1,3,5-tr.iallynyld-2'am-inoka.rbonyl] -2-chlorobenzenesulfonam, id. 10. Measure according to the provisions. 2. A process as claimed in claim 1, wherein the active ingredient is N - [(4,6-dimetoQ1'-s-1,3,5-triazinyl-2 / - 'alm-nocarbonyl] -2 "' chlo-oben-. zeno-sulfonamide. The agent according to claim 1, characterized in that the active ingredient is N - [(4,6-cfvumethoxy -1,3,5-tria 1 inocarbonyl) - 2,5-rdwu.me toxybenzene-1-isulfonamide The agent according to Claim 1, characterized in that, as a compound, the compound comprises N - [/ 4,6-dimethoxy -1 ~ 3,5-triazines1'0- 2 / -am'in'carbonyl] -benlZenesulfonamiide., 13, The agent according to claim 1, characterized in that the active ingredient is N- [14-methoxyrsy-6-methyl10-1,3,5- <RTI ID = 0.0> thI &quot; liazines10-2'-aminacr bonyl] -2 chlorine, o-5-methoxybenzenesulfon, m. id. 14. S, measure according to ~ a'str. 2. The process of claim 1, wherein the active s' aldehyde is N - [(4-methoxy-6-Iriethyl-1,3,5-triazinyl-2H-aminocarbonyl].:. -benzenosulf'Onamlid. 15. The measure according to the provisions of The compound of claim 1, wherein the active ingredient comprises N- [14,6-dimethylO-1,3,5-trilazinyl-2H-amdndlrorbonyl] -benz, enosulfon, amide. 16. An agent for combating undesirable plants, characterized by the fact that a part of at least one surface substance has been resolved: fruit or solid. or, a liquid rosin, a 7.al \ Viera extract as a combined component of at least one new N- / he t-eriOcycloaminocarbonyl / -arylsulfonamide of total HCO 1, in which R is a giTUpe of formula 4 or 5 in which. that N-alch X 'is CH and OCH 2 - and Z is a methyl radical or an ethyl radical, a trifluoromethyl or l-ethoxyl radical, R1 is a group of formula 6, in which R a and R 6 are the same. They are different and denote hydrogen,., fluorine, chlorine, ~ ohm and iodine, rhodium,: alkyl and alkoxy, 1-4 carbon atoms, nitro and tri? uoromethyl groups. cyano or. groups of the formula CHsS / O / n - or CH s CH 2 S / O / n, in which n is the number zero, 1 or '2, R "means a hydrogen, fluorine, chlorine, bromine or methyl radical, R 6 means a hydrogen, fluorine, chlorine or bromine atom or a methyl or tromine or a methyl radical; or methoxy, and R 7 'is an odor, fluorine, chlorine or bromine atom · or an alkyl or alkoxy radical with 1-2 carbon atoms, where when R 1 is being a non-hydrogen atom, then at least one of R a,. R 1, R 6 'and ~ 7 is different from a hydrogen atom and. at least 2 · Z substituents R a "R" " Re iR 7 mu ~ denotes hydrogen altoms and when R 1 is a hydrogen atom and all substituents. Fniki R a, R "" Re and R 7 m 'can denote chlorine atoms or rhodium atoms. and when both R a and R 7 are hydrogen, then at least one is a methyl radical CHa-S-1 or CH and OCH 2 -, and Z is a methyl radical. or metorxyl, R i denotes the group of the eagle 6, w, in which YIP R a li and Re are the same or different and are we 'hydrogen, fluorine, chlorine, bromine and iodine, alkyl and alkoxy radicals with 1-4 carbon atoms, g ["nitro, trifluoro-. methyl, cyano or CHaS / O / n or CH a CH 2 S / O / n-, in which in Z'or n is a number. zero, 1 or 2, R "denotes hydrogen, fluorine, chlorine, bromine, allbo and" methyl radical, Rs 10 oznCl! c ~ aja hydrogen, fluorine) chlorine or bromine atom or ["10dnJk methyl albomethoxy and R 7 enters a hydrogen, fluorine, chlorine or bromine atom, or an alkyl or alkoxy radical of 1-2 'carbon atoms, whereby when R 6 is a non-hydrogen substituent, then at least less one of the substitutes R a, R ", Re and R 7 is different from a hydrogen atom, and 'CO at least 2 of the substituents R a, R", Re. and R 7 must be denoted as: cZlacatomyw'o: "doru and when R s represents a hydrogen atom and all 20 subs, R a, R", R 0 and R 7 are different than hydrogen, and sometimes all bases: k and R a, R " , Re and HJ mUS: ia denote chlorine atoms or methyl radicals' or-az when both bases WD.i! Ki R ai R 7 o ~ na czaja a t.omy \\ ~ odor, including ~ eo ~ iej, one of the substituents R ", R s or Re must be a hydrogen atom, or R and in WZ: Qrze 1 denotes the group of formula 7, in which the rhythm Q denotes oxygen or sulfur. and Re '' is · hydrogen, rhodium-methyl-a 'or ch11Q: rt1 or br'omine, or,, R1 is a group of formula. 8 or 9, connected to the nucleus, and 196 bases R 9 and R 10, are one or different and represent a hydrogen atom, methyl radicals, chlorine atoms or. of bromine, and W in formula 1 'means l (number of oxygen or sulfur, where, W, and Q may be one: single or different li compound' O knot · Salt form appropriate to Istosowand! A ~ in agriculture, ie. 19. SJ "odek according to substitute; z. 18, characterized by the fact that as an active ingredient it contains N - [/ 4,6-dimethoxy pyrimidinyl 20. The agent according to Fig. 18, characterized in that the active ingredient is N - [/ 4,6-dimethyl pyrimidinyl -2H-aminoO'carbonyl] benzenesulfonamide. 21. The agent according to claim 18, characterized in that the active ingredient is N - [[beta] -methoxy-6'-methyl-1,3,5 -trJ.azine10-2 / -aminocarbony10] -2- -chlorobenzeneIllosulfonamid 22. The agent according to claim 18, characterized in that, as the main component, ZlawieTa N- [14,6-dimetic -1,3,5-tT liazines1'0-2 / -amiri.Qlcarbonyl] -benzenesulf'o ·· namid. 23. Measure according to z8strz. The process as claimed in claim 18, characterized in that the active ingredient is N- [14-m'ethoxy-6-methyl-1,3,5-, triazinyl-2 / -aminocCl "bonyl] -be.n zenesulone. billion. 24. The measure according to, gltr, z. 18, characterized by the fact that the active ingredient contains N - [/ 4,6-dimethyl -1, ~, 5-triJazy.nyl-2 / -aminocarbonyl0 '] - benzenesulphona'mid 114 069' vV R 1 -S0 -Nl-l II 2 -CN ~ -R WZ (jr 1 J: \ RQ 8 Formula 7 Formula 8 \ J '/ z (jr 2 WzO'r 3 x - <- (NN ~ Z WZr: 1r 5 Pattern 9 Pattern 60 W NH R II II fS02NHC -N / 'N ~~ ZNX Pattern 12 Pattern 13 -o- 10 H' I 'II 3 e _ 502 NHCNHR Pattern 14 Pattern 10 Formula 15 o OCH3 CHD- 'II A 3 _ S02 NH - C-NH - \. I ~. N ~ OCH3 Formula 16 Formula 17n 5 "5 / \ II S02NHCNHR Formula 18 114 069 R 6 R 7 OCH 3 ~ N, RS f, 502NHCNH ~ _ R 4 R 3 OCH 3 Formula 21 CH3 ~ N, S02 NCNH - {I N- HX Formula 22 Formula 24 x. ~ N- (/ 502NHCNH ~~ H JC ~ ZR g SR 10 Formula 25 Formula 26 Formula 23 Formula 27 x WN \\ 502NHCNH {'\' / i NZ R g 5 R 10 Formula 28 Formula 29 Formula 30 Formula 31 114 069 XR 7 XO (~ N- {~ ~ N - (O S02NHCNH - {~ NO S02NHCNH ~~. N == \ R 4 R 3 ZR 3 Z Formula 32 Formula 35 XX ~ N-- <~ N = <SO2NHCNH- {N SO2NHCNH \ - \ N N = \ R 4 Z Rit R 3 Z Formula 36 Pattern 39 X R 7 X ~ ~ N - (O ~ N = &Lt; RSSO2NHCNH- (NSO2NHCNH- {t N N == <, N- \ R 4 Z R 4 R 3 Z Formula 37 Formula 40 \ - ..... X X --O (~ N == <O / II N = "= \ R S O S02NHCNH - {N R S S02NHCNH- {N N - \ t ~ - \ R 4 R 3 Z R 3 Z Formula 38V / zór 42 X Re R 7. O N = <II J N S02NHCNH ~~ Z R4 R 3 3 Formula 4 114 069 Formula 45 x ~. N - {SO NHCNH --- f N 06 2 N == <~ ~ Z ~ I ~ Formula 46 x O N -, (II -.li N S02NH-C-NH \ = I) LJl N- \ R g SR 10 Z Formula 44 OCH 3. (Ni N == \ CH 3 CH 3 Pattern 51 Pattern 50 OCH 3 <~ (Ni N == \ OCH 3 F Formula 53. Formula 52 <~ <~ Cl Br 55 Formula 54 CH 3 <~ N - {(~ N N = \ OCH 3 OCH 3 Formula 57 Formula 56 <- Formula 48 <~ C 2, HS 'Pattern 58 ~ 3C ~ CH 3 Pattern 60 Pattern 62 nS ~ C (- Cl Pattern 59 Cl TL ~ CH3 Pattern 61 Cl Q- Cl Pattern 63 chip 64114069 Pattern 65 ~' N ~ CH3.SOiNHCNH) O (RX 3 Formula 68 3 V / zór 66 Formula 69 Formula 67 Formula 70 R1S02NH ~ NH- \ ~ Z Formula 71 n Cl SCl Formula 77 Formula 76 Formula 74 Formula 73 ~ O Formula 72 fi Cl S Formula 75 Formula 78 Formula 79 CH 3 ~ NO ~ sa NH-CNH- \ '- = ::. IN 2 N \ OCH3 Formula 80 Formula 61 x ~ N ~ S02NHCNH--) (J (N' of Cl S CI Formula 85 x ~ N ~ (+) 50 -N-CNH- 2 (-) N ~ R 3. 'OCH 3 Formula 86 114 089 Formula 82 Formula 83 OCr1 ~ O ~ J II N ~ ((5 \ -50 -NH-C -NH- (ON ~ 2 N ~. CI CH 3 Formula 88 OCH 3 n ~ NO ~ "sAsa -NH-C-NH- {N 2 N = <CH 3 Formula 89 Cl CH3 ~ N: d sa -NH-C-NH- (ON 2 N ~ OCH3 Formula 91 OCH 3 Q- ~ N ~ OS ~ -NH-C-NH- N ~ Ct OCH 3 Formula 92 o ~ OCH3 II N \ Q (S ~ -NH-C-NH) O Ci OCH 3 Formula 93 \ Vzór 97 114 869 Formula 94 o N ~ OCl ~ l3 50 -NH- ~ -NH- 2 N Cl CH 3 Formula 95 Formula 95 Formula 100 Formula 101 Cl o OCH 3 II N SO2- NH - C -NH- N OCH 3 CH 3 'vVz6r 99 Formula · 102 Formula 107 Cl °. OCH3. II N ~ SO2 -NH- C-NH- N ~ CH3 Formula 103 V '; zor 104 114 069 Formula 106 H CO - .3 \ C ~ c = - = NO -d 3 HC' - _ "- ~ _NF NH C-NH-S0 2 ~ J / ~~ 3CO Formula 112 C (F 3 C HC / ~ N Il IO fl / C, ~ C, II - -O 3 CN NH-C-NH-SO "2 ~ # V'Jor 109 q- 0 II 'N ~ # S02 - NH-C-NH-C "'::: CO-CH II J 3 CI N'C ~ N · I O - CH 3 Formula 110 YO II N ~. # 502 - NH-C-NH ~ C / ~ CO-CH II l 3 Cl N'C eN I O-CH 3 Formula 111 P O-CH 3 O li. ~ J ~ J S02-NH-C-NH-C ~ 'CO-CH I II 3 CI N ~ c / CH I CH 3 Formula 108 H 3 CO, Cl CN O -b 'I / ~' II -, N C-NH-C-NH-SO - ~ h \ / 2 ~ UC = N / H 3 C " Vz6r 113 H 3 CO \ H 3 CO C-NO rf ~ -NH- ~ -NH-SO ~ \. I 2., C = NH 3 Cd OCH3. Pattern 114Wz6r 115 Formula 116 Formula 117 114 069 Formula-118 Vlzó r 119 Formula 120 VJ Pattern 121 Pattern 124 CH O - / 3 II N ~ S · S ~ -NH-C-NH- Cy N ~ CH 3 Formula 122 CH 3 CH 3 ~ N :::: {S02-NH-C -NH ~ 0 <~ CH 3. OCH 3 Formula 123 Wz6r 125 VJzor 126Cl CH 3 N CF3 Formula 127 Cl CH 3 ~ N SOTNH- C- NH - N Cl H Wz6r 128 114069 FFF OCH3 o II N SO -NH-C-NH- 2 N OCH 3 Formula 130 Br OCH 3 ~ N sa -NH-C-NH- (O 2 N OCH 3 Formula 131 Formula 129 Formula 133 o (Q (11 N O-CH 3 O sa -NH-C-NH-C / ~ C "/ 2 II I, N, eCH et CI CH 3 Formula 134 Cl OCH3 ~ N SO -NH-C-NH- 2 N Cl OCH 3 Formula 132 Formula 136 OCH3 O II N Or s SO -NH-C-NH- II 2 N OCH3 Formula 137 H 3 CO, O -bF CN II Hc '/ ~ C-NH-C- NH-S02 O \ / C = N / H 3 C Formula 138 Formula 141 Formula 139 Formula 140 H 3 C, CI CN O - © Q ~ II He C-NH-C-NH-SO O \ .1 2 C = N / H 3 C Formula 145 CH _ ° NC 3 O- II Q \\. ~ # ~ -NHC-NH- CN == CCH \ CH 3 Formula 146 Pattern 147 114 ••• H 3 CO, H 3 CO CN O / I \\ II HC,, C-NH-C-NH-SO2 C == NH 3 Có 'OCH3 MODEL 142 Formula 143 Formula 144 Formula 148 CH 3 CH P- O Nt 3 II 1 / \\ ~ b S02-NH-C-NH- C CH \ / N = C CH 3 \ CH 3 Formula 1 ~ 9 -FC ~ 1 Ó- O / 3 - NC II II ~ I. S02-NHC-NH-C "CH .// \ / N == C \ CH '3 Formula 150O OCH3 O- NC C' II II ~. ~ B; :: 02-NHC-NH-C CH. - = Cl 1 CH 3 Formula 151. 114 069 C l OCH 3 OCH ° N '3 II \ - ~ SO2-NHC-NH- CH = c \ OCH3 Formula 154 _ ° CO CH: 3 o-SO2-NH ~ -NH-l-' 'cH \ / N = C \ OCH 3 Formula 152 Ó- Cl O, CH3 _ NC II II ~ ~ It S02-NHC-NH-C '\ CH ·' N- / -CH Formula 155 Cl Ci CH 3 ON Ci II - S02-NHC-NH -C '' 'cH \ IN = C \ CH3 Formula 153 .el F CH3 O- ° NI II II - \\ ~ b SO2-NHC-NH-C CH. \ / N = C \ CH3 VJz6r 156 CH ° '3 O- II tJ- ~ ~! J S02-NHC-NH-C I \ J \ - IN = C \ CH 3 Formula 157 "\ fzor 2 Formula 3 SCHEME Formula 1114 069 Oli O SCHEME 2 nBuLi EO RT t 2 '~) HOH r [2, - NH4 OH n excess (COCl) 2 0-5) ~ - ~) o S02NH2 SCHEME 3 PL PL PL PL PL PL

Claims (7)

1. Patent claims 1. An agent for combating undesirable vegetation, characterized in that, in addition to at least one surface-active substance and / or a solid or liquid diluent, it contains as an active ingredient at least ; less one new N- (heterocycloamino-carbonyl) -3rylslllf1onam-d-o, general formula 1, vV wherein R is the group of formula 4 or 5, wherein Eq, or X is n-o fu, chlorine or bromine, methyl, alkoxy, 1-3 carbon or methoxy radicals and Z is methyl or methoxy flooflyc, R1 is Grl.I'pe of formula Ba, where R s ~ denotes a hydrogen, fluorine, -chlorine or bromine atom, an alkyl radical with 1-3 carbon atoms, a group of 1-3 carbon atoms, methoxy .. lpv or trifluoromethyl, R 4 is a hydrogen atom, a fluorine atom, a chlorine atom, a brO group, a methoxy group An alkyl group of 1-3 carbon atoms, or R 1 is a group of formula 7, where mQ ': is a s-atom and R s is a hydrogen atom and W in the formula 1 'can reach, tepg'wac in the post ac. and free or in the form of salt suitable for use in agriculture. 2. The measure according to claim A process as claimed in claim 1, characterized in that the active ingredient is N - [(4-methoxy-B ... methylpyrimidinyl-2'-amino'inoco, VbonylJ-2-chloro benzene-1sulfonamide). 3. Sr'Odek according to claim The method of claim 1, wherein the active ingredient comprises N- [14, B-dimethoxy pyrrinidine10-2H-a'minocavbony10] -2,5-dichloroX'-benzenesulfone'mlide. 4. A measure according to claim A process as claimed in claim 1, characterized in that the active ingredient is N - [(4-methoxy-B-methylpyrinllidine 10-2H-aminocarbonyl -] - 2-methylbenzene-sulfonamide). 5. The measure according to claim According to claim 1, characterized by. that it comprises N - [(4,6-dimethylpyrimidinyl-2 / -aminok'VQ.onyl0] .- ~ -thiophenesulfonate as active ingredient! d. 6. The measure according to claim A process as claimed in claim 1, characterized in that as an active ingredient: a N - [(4-methdxy-6-methylpyrinidin] 10-2H-aminocetboolyl] -2-'chloalkyl-5 ... I-methoxybenzenesulfonamide. 7. The measure according to claim 1, characterized by the fact that the active ingredient is N - [(4,6-dimethyl pyrimides: nyl-21-aminocarbanyl] -2,6-dichloro-benzenesulfonamide. 114069 193 194 45 20 40 25 10 30 of R 4, R s or Re must be hydrogen, or R 1 in formula 1 is a group of formula 7, where Q is' oxygen 'or sulfur and R s' is - hydrogen volume, methyl radical or chlorine or rhodium atom, or R 1. stands for the group pe of formula 8 or g ', while in formula 8 the constants R g and R l0 are the same or different and denote hydrogen atoms, .m · e1ty, lorvie, .atom1Y radicals of chlorine or bromine, and W in for formula 1 means: oxygen or sulfur atom, with cZ-Ylm W and Q. may be j ~ dlllalkQlw or different and the compound of formula '1 may exist in free or in form salt suitable for use in x'olnictvtie. 17. Measure for the control of damaged nasal plants, characterized by the fact that, in addition to '00', the least one surface substance is active and / or solid or solid l "o" The thin-walled active ingredient comprises at least one new N- (hetero-cyclo? minocarbonyl / -aryl? sulfonamide of general formula 1, in which R &lt; RTI ID = 0.0 &gt; 3 &lt; / RTI &gt; 4 or 5, in which X represents an atom of carbon or methylthio or bro'mu, rhodium, and k-methyl, al, col {1sylO'wy ', 1 to 3 atoms, carbon or methylthio and Z is the radical. methyl or met'olxyl, then R 1 denotes a group of formula 6, in which R a and Re are the same or different, and l denote hydrogen, fluOTU, chlorine, bromine, and iodine atoms, alkyl and alkoxy radicals o. 1-- -4 carbon atoms, g: nitro roups, tr6 j uoromethyl, cyano 1 or groups with WZOIf, le CHsS / O / n- or 'CHsCft ~ / O / n-, k; 1 or 2, R4, OZ! The number of hydrogen atom, fIU OTU "chlorine, bromine or a methyl radical, R & denotes a flu atom oru ,. chlorine or bromine or a methyl or methoxy radical, 35 R 7 is a hydrogen atom, fluo:, u, ~ hlor, lUD, bromine, or an alkyl radical of carbon, where at least one of substituents R s,. R "" R 6 and · R 7 is other than hydrogen and at least of the 2 'R s, R "" R 6 and. R 7 must be hydrogen atoms · and when both substitute R s. R a and R 7 are hydrogen, then at least one of the R or R 6 substituents must be a hydrogen atom or R 1 in the formula 1 is a group of the formula 7: where Q is a sulfur atom and R s is a radical . methyl or ", chlorine or bromine atom, or R 1 represents 8 or 9, where in" formula "8 R g and R 10 are single or different and represent hydrogen atoms, radicals / methyl, chlorine or bromine atoms, and W in the formula 1, meaning, for the oxygen atom or: sulfur, with W and Q may be the same or different and the compound of formula 1 may exist in free form ~ j or in the form of a salt suitable for use in agriculture. ~ 8 ~ An agent for regulating the growth of plants, characterized in that in addition to one active surface substance and / or The liquid solvent comprises the following: an active ingredient of at least one new N- (heterocycloam-inocla T'bonyl / aryl sulfonamide of the general formula I, wherein R is the group of formula 4, or , wl ~ t6ry.ch to · in the X terms: hydrogen, chloro or bromine, methyl, ethyl or alkoxy radical, or 1-3 carbon atoms, ... rnn ~ k tr6j: fluorometh- 50 60 85 8 '.. The agent according to claim 1, characterized in that as) the active ingredient comprises N - [(4,6-dimethylpyrimlidine 10-2) -aminocarbonyl 10] -benzenesulf'Ona-, mid. 9. The measure according to claim A process as claimed in claim 1, characterized in that the active ingredient comprises N- [i4-mephoxY-6-methyl-1,3,5-tr.iallynyld-2'am-inoka.rbonyl] -2-chlorobenzenesulfonam, id. 10. Measure according to the provisions. 2. A process as claimed in claim 1, wherein the active ingredient is N - [(4,6-dimetoQ1'-s-1,3,5-triazinyl-2 / - 'alm-nocarbonyl] -2 "' chlo-oben-. zeno-sulfonamide. The agent according to claim 1, characterized in that the active ingredient is N - [(4,6-cfvumethoxy -1,3,5-tria 1 inocarbonyl) - 2,5-rdwu.me toxybenzene-1-isulfonamide The agent according to Claim 1, characterized in that, as a compound, the compound comprises N - [/ 4,6-dimethoxy -1 ~ 3,5-triazines1'0- 2 / -am'in'carbonyl] -benlZenesulfonamiide., 13, The agent according to claim 1, characterized in that the active ingredient is N- [14-methoxyrsy-6-methyl10-1,3,5- <RTI ID = 0.0> thI &quot; liazines10-2'-aminacr bonyl] -2 chlorine, o-5-methoxybenzenesulfon, m. id. 14. S, measure according to ~ a'str. 2. The process of claim 1, wherein the active s' aldehyde is N - [(4-methoxy-6-Iriethyl-1,3,5-triazinyl-2H-aminocarbonyl].:. -benzenosulf'Onamlid. 15. The measure according to the provisions of The compound of claim 1, wherein the active ingredient comprises N- [14,6-dimethylO-1,3,5-trilazinyl-2H-amdndlrorbonyl] -benz, enosulfon, amide. 16. An agent for combating undesirable plants, characterized by the fact that a part of at least one surface substance has been resolved: fruit or solid. or, a liquid rosin, a 7.al \ Viera extract as a combined component of at least one new N- / he t-eriOcycloaminocarbonyl / -arylsulfonamide of total HCO 1, in which R is a giTUpe of formula 4 or 5 in which. that N-alch X 'is CH and OCH 2 - and Z is a methyl radical or an ethyl radical, a trifluoromethyl or l-ethoxyl radical, R1 is a group of formula 6, in which R a and R 6 are the same. They are different and denote hydrogen,., fluorine, chlorine, ~ ohm and iodine, rhodium,: alkyl and alkoxy, 1-4 carbon atoms, nitro and tri? uoromethyl groups. cyano or. groups of the formula CHsS / O / n - or CH s CH 2 S / O / n, in which n is the number zero, 1 or '2, R "means a hydrogen, fluorine, chlorine, bromine or methyl radical, R 6 means a hydrogen, fluorine, chlorine or bromine atom or a methyl or tromine or a methyl radical; or methoxy, and R 7 'is an odor, fluorine, chlorine or bromine atom · or an alkyl or alkoxy radical with 1-2 carbon atoms, where when R 1 is being a non-hydrogen atom, then at least one of R a,. R 1, R 6 'and ~ 7 is different from a hydrogen atom and. at least 2 · Z substituents R a "R" " Re iR 7 mu ~ denotes hydrogen altoms and when R 1 is a hydrogen atom and all substituents. Fniki R a, R "" Re and R 7 m 'can denote chlorine atoms or rhodium atoms. and when both R a and R 7 are hydrogen, then at least one is a methyl radical CHa-S-1 or CH and OCH 2 -, and Z is a methyl radical. or metorxyl, R i denotes the group of the eagle 6, w, in which YIP R a li and Re are the same or different and are we 'hydrogen, fluorine, chlorine, bromine and iodine, alkyl and alkoxy radicals with 1-4 carbon atoms, g ["nitro, trifluoro-. methyl, cyano or CHaS / O / n or CH a CH 2 S / O / n-, in which in Z'or n is a number. zero, 1 or 2, R "denotes hydrogen, fluorine, chlorine, bromine, allbo and" methyl radical, Rs 10 oznCl! c ~ aja hydrogen, fluorine) chlorine or bromine atom or ["10dnJk methyl albomethoxy and R 7 enters a hydrogen, fluorine, chlorine or bromine atom, or an alkyl or alkoxy radical of 1-2 'carbon atoms, whereby when R 6 is a non-hydrogen substituent, then at least less one of the substitutes R a, R ", Re and R 7 is different from a hydrogen atom, and 'CO at least 2 of the substituents R a, R", Re. and R 7 must be denoted as: cZlacatomyw'o: "doru and when R s represents a hydrogen atom and all 20 subs, R a, R", R 0 and R 7 are different than hydrogen, and sometimes all bases: k and R a, R " , Re and HJ mUS: ia denote chlorine atoms or methyl radicals' or-az when both bases WD.i! Ki R ai R 7 o ~ na czaja a t.omy \\ ~ odor, including ~ eo ~ iej, one of the substituents R ", R s or Re must be a hydrogen atom, or R and in WZ: Qrze 1 denotes the group of formula 7, in which the rhythm Q denotes oxygen or sulfur. and Re '' is · hydrogen, rhodium-methyl-a 'or ch11Q: rt1 or br'omine, or,, R1 is a group of formula. 8 or 9, connected to the nucleus, and 196 bases R 9 and R 10, are one or different and represent a hydrogen atom, methyl radicals, chlorine atoms or. of bromine, and W in formula 1 'means l (number of oxygen or sulfur, where, W, and Q may be one: single or different li compound' O knot · Salt form appropriate to Istosowand! A ~ in agriculture, ie. 19. SJ "odek according to substitute; z. 18, characterized by the fact that as an active ingredient it contains N - [/ 4,6-dimethoxy pyrimidinyl 20. The agent according to Fig. 18, characterized in that the active ingredient is N - [/ 4,6-dimethyl pyrimidinyl -2H-aminoO'carbonyl] benzenesulfonamide. 21. The agent according to claim 18, characterized in that the active ingredient is N - [[beta] -methoxy-6'-methyl-1,3,5 -trJ.azine10-2 / -aminocarbony10] -2- -chlorobenzeneIllosulfonamid 22. The agent according to claim 18, characterized in that, as the main component, ZlawieTa N- [14,6-dimetic -1,3,5-tT liazines1'0-2 / -amiri.Qlcarbonyl] -benzenesulf'o ·· namid. 23. Measure according to z8strz. The process as claimed in claim 18, characterized in that the active ingredient is N- [14-m'ethoxy-6-methyl-1,3,5-, triazinyl-2H-aminocC11 "bonyl] -be.n zenesulone. billion. 24. The measure according to, gltr, z. 18, characterized by the fact that the active ingredient contains N - [/ 4,6-dimethyl -1, ~, 5-triJazy.nyl-2 / -aminocarbonyl0 '] - benzenesulphona'mid 114 069' vV R 1 -S0 -Nl-l II 2 -CN ~ -R WZ (jr 1 J: \ RQ 8 Formula 7 Formula 8 \ J '/ z (jr 2 Pattern 3 x - <- (NN ~ Z WZr: 1r 5 Pattern 9 Pattern 60 W NH R II II fS02NHC -N / 'N ~~ ZNX Pattern 12 Pattern 13 -o- 10 H' I 'II 3 e _ 502 NHCNHR Pattern 14 Pattern 10 Pattern 15 o OCH3 CHD- 'II A 3 _ S02 NH - C-NH - \. I ~. N ~ OCH3 Pattern 16 Pattern 17n 5 "5 / \ II S02NHCNHR Pattern 18 114 069 R 6 R 7 OCH 3 ~ N, RS f, 502NHCNH ~ _ R 4 R 3 OCH 3 Formula 21 CH3 ~ N, S02 NCNH - {I N- HX Formula 22 Formula 24 x. ~ N- (/ 502NHCNH ~~ H JC ~ ZR g SR 10 Pattern 25 Pattern 26 Pattern 23 Pattern 27 x WN \\ 502NHCNH {'\' / i NZ R g 5 R 10 Pattern 28 Pattern 29 Pattern 30 Pattern 31 114 069 XR 7 XO (~ N- {~ ~ N - (O S02NHCNH - {~ NO S02NHCNH ~~. N == \ R 4 R 3 ZR 3 Z Formula 32 Formula 35 XX ~ N - <~ N = <S02NHCNH- {N SO2NHCNH \ - \ NN = \ R 4 Z Rit R 3 Z Formula 36 Pattern 39 XR 7 X ~ ~ N - (O ~ N = <RS S02NHCNH - (N S02NHCNH- {t NN == <, N- \ R 4 ZR 4 R 3 Z Formula 37 Formula 40 \ - ..... XX --O (~ N == <O / II N = " = \ RSO S02NHCNH - {NRS S02NHCNH- {N N - \ t ~ - \ R 4 R 3 ZR 3 Z Formula 38V / zor 42 X Re R 7. o N = <II J N S02NHCNH ~~ Z R4 R 3 3 Formula 4 114 069 Formula 45 x ~. N - {SO NHCNH --- f N 06 2 N == <~ ~ Z ~ I ~ Formula 46 x O N -, (II -.li N S02NH-C-NH \ = I) LJl N- \ R g SR 10 Z Formula 44 OCH 3. (Ni N == \ CH 3 CH 3 Formula 51 Formula 50 OCH 3 <~ (Ni N == \ OCH 3 F Formula 53. Formula 52 <~ <~ Cl Br 55 Pattern Pattern 54 CH 3 <~ N - {(~ NN = \ OCH 3 OCH 3 Pattern 57 Pattern 56 <- Pattern 48 <~ C 2, HS 'l./ Pattern 58 ~ 3C ~ CH 3 Pattern 60 Pattern 62 n . S ~ C (- Cl Formula 59 Cl TL ~ CH3 Formula 61 Cl Q- Cl Formula 63 chip 64114069 Formula 65 ~ 'N ~ CH3. SOiNHCNH) O (RX 3 Formula 68 3 V / pattern 66 Formula 69 Formula 67 Formula 70 R1S02NH ~ NH- \ ~ Z Formula 71 n Cl SCl Formula 77 Formula 76 Formula 74 Formula 73 ~ O Formula 72 fi Cl S Formula 75 Formula 78 Formula 79 CH 3 ~ NO ~ sa NH-CNH- \ '- = :: .IN 2 N \ OCH3 Formula 80 Formula 61 x ~ N ~ S02NHCNH--) (J (N 'of Cl S CI Formula 85 x ~ N ~ (+) 50 -N-CNH- 2 (-) N ~ R 3 . 'OCH 3 Formula 86 114 089 Pattern 82 Formula 83 OCr1 ~ O ~ J II N ~ ((5 \ -50 -NH-C-NH- (ON ~ 2 N ~. CI CH 3 Formula 88 OCH 3 n ~ NO ~ "sAsa -NH-C-NH- {N 2 N = <CH 3 Formula 89 Cl CH3 ~ N: d sa -NH-C-NH- (ON 2 N ~ OCH3 Formula 91 OCH 3 Q- ~ N ~ OS ~ -NH-C-NH- N ~ Ct OCH 3 Formula 92 o ~ OCH3 II N \ Q (S ~ -NH-C-NH) O Ci OCH 3 Formula 93 \ Vform 97 114 869 Formula 94 o N ~ OCl ~ l3 50 -NH- ~ -NH- 2 N Cl CH 3 Formula 95 Formula 95 Pattern 100 Formula 101 Cl o OCH 3 II N SO 2 - NH - C -NH- N OCH 3 CH 3 'vVz6r 99 Formula 102 Formula 107 Cl °. OCH3. II N ~ SO2 -NH- C-NH- N ~ CH3 Formula 103 V '; zor 104 114 069 Formula 106 H CO - .3 \ C ~ c = - = NO -d 3 HC' - _ "- ~ _NF NH C-NH-S0 2 ~ J / ~~ 3CO Formula 112 C (F 3 C HC / ~ N Il IO fl / C, ~ C, II - -O 3 CN NH-C-NH-SO "2 ~ # V 'Jzór 109 q- 0 II' N ~ # S02 -NH-C-NH-C "'::: CO-CH II J 3 CI N'C ~ N · I O - CH 3 Formula 110 YO II N ~ . # 502 - NH-C-NH ~ C / ~ CO-CH II l 3 Cl N'C eN I O-CH 3 Formula 111 P O-CH 3 O li. ~ J ~ J S02-NH-C-NH -C ~ 'CO-CH I II 3 CI N ~ c / CH I CH 3 Formula 108 H 3 CO, Cl CN O -b' I / ~ 'II -, N C-NH-C-NH-SO - ~ h \ / 2 ~ UC = N / H 3 C "Vz6r 113 H 3 CO \ H 3 CO C-NO rf ~ -NH- ~ -NH-SO ~ \. I 2., C = NH 3 Cd OCH3. Ex6r 114Wz6r 115 Pattern 116 Pattern 117 114 069 Pattern - 118 Vlzór 119 Pattern 120 VJ Pattern 121 Pattern 124 CH O - / 3 II N ~ S · S ~ -NH-C-NH- Cy N ~ CH 3 Pattern 122 CH 3 CH 3 ~ N :::: {SO2-NH-C-NH ~ 0 <~ CH 3. OCH 3 Formula 123 Pattern 125 VJzor 126Cl CH 3 N CF3 Formula 127 Cl CH 3 ~ N SOTNH- C- NH - N Cl H Pattern 128 114069 FFF OCH3 o II N SO -NH-C-NH- 2 N OCH 3 Formula 130 Br OCH 3 ~ N sa -NH-C-NH- (O 2 N OCH 3 Formula 131 Formula 129 Formula 133 o (Q (11 N O-CH 3 O sa -NH-C-NH-C / ~ C "/ 2 II I, N, eCH et CI CH 3 Formula 134 Cl OCH3 ~ N SO -NH-C- NH- 2 N Cl OCH 3 Formula 132 Formula 136 OCH3 O II N Or s SO -NH-C-NH- II 2 N OCH3 Formula 137 H 3 CO, O -bF CN II Hc '/ ~ C-NH-C- NH-S02 O \ / C = N / H 3 C Formula 138 Formula 141 Formula 139 Formula 140 H 3 C, CI CN O - © Q ~ II He C-NH-C-NH-SO O \ .1 2 C = N / H 3 C Formula 145 CH _ ° NC 3 O- II Q \\. ~ # ~ -NHC-NH-CN == CCH \ CH 3 Formula 146 Pattern 147 114 ••• H 3 CO, H 3 CO CN O / I \\ II HC,, C-NH-C-NH-SO2 C == NH 3 Có 'OCH3 Formula 142 Formula 143 Formula 144 Formula 148 CH 3 CH P- O Nt 3 II 1 / \\ ~ b S02-NH-C-NH- C CH \ / N = C CH 3 \ CH 3 Formula 1 ~ 9 -FC ~ 1 Ó- O / 3 - NC II II ~ ~ I. S02-NHC-NH-C "CH .// \ / N == C \ CH '3 Formula 150O OCH3 O- NC C 'II II ~. ~ B; :: 02-NHC-NH-C CH. ~ = Cl \ CH 3 Formula 151. 114 069 Cl OCH 3 OCH ° N' 3 II \ - ~ SO2-NHC-NH- CH = c \ OCH3 Formula 154 _ ° CO CH: 3 o-S02-NH ~ -NH-l- '' cH \ / N = C \ OCH 3 Formula 152 Ó- Cl O, CH3 _ NC II II ~ ~ It S02- NHC-NH-C '\ CH ·' N- / -CH Formula 155 Cl Ci CH 3 ON Ci II - SO2-NHC-NH-C '' 'cH \ IN = C \ CH3 Formula 153 .el F CH3 O- ° NI II II - \\ ~ b SO2-NHC-NH-C CH. \ / N = C \ CH3 VJz6r 156 CH ° '3 O- II tJ- ~ ~! J SO2-NHC-NH-C I \ J \ - IN = C \ CH 3 Formula 157 "\ fzor 2 Formula 3 SCHEME Formula 1114 069 Oli O SCHEME 2 nBuLi EO RT t 2 '~) HOH r [2, - NH4 OH n excess (COCl) 2 0-5) ~ - ~) o S02NH2 SCHEME 3 PL PL PL PL PL PL PL