PL116723B1 - Herbicide and fungicide - Google Patents

Description

The subject of the invention is a herbicide and fungicide. In agriculture, there is a great demand for herbicides and fungicides that do not damage crop plants. Particular difficulties are associated with finding so-called selective herbicides for foliar application, because these agents are applied to the leaves of both weeds and useful plants, and are intended to control only weeds. Moreover, among the fungicides available There are very few preparations on the market that effectively combat fungi that cause plant diseases such as rust. It has now been discovered that the fungicides and herbicides according to the invention are safe, beneficial agents for combating weeds and plant pathogens, without having any harmful effects. on useful plants. The feature of the herbicide and fungicide according to the invention is that as an active substance it contains a compound of formula 1, in which Rx is a lower alkyl group, a cycloalkyl group with 3-5 carbon atoms, a lower alkenyl group, lower haloalkyl group, lower cyanoalkyl group, lower alkoxy group, cycloalkoxy group with 3-5 carbon atoms, lower alkynyl group, lower haloalkoxy group, lower alkenyloxy group, lower alkynyloxy group, lower alkylthio group, lower group u- 25 pe alkenylthio, lower alkynylthio group, alkoxyalkyl group with 1-2 carbon atoms in the alkoxy radical and 1-2 carbon atoms in the alkyl radical, alkylthioalkyl group with 1-2 carbon atoms in the alkylthio radical and 1-2 carbon atoms in the radical alkyl, a lower haloalkynyloxy group, an alkoxyalkoxy group with 1-2 carbon atoms in the alkoxy radicals or a 2-furfuryloxy group, R2 is a hydrogen atom or an alkyl group with 1-2 carbon atoms, R3 is the same or different substituents, such as a hydrogen atom, a halogen atom, an alkyl group with 1-4 carbon atoms, an alkoxy group with 1-3 carbon atoms, a haloalkyl group with 1-3 carbon atoms or an alkylthio group with 1-3 carbon atoms, n is an integer from 1 to 3, where when R3 is a fluorine atom, then n is an integer from 1 to 5, Y is an oxygen or sulfur atom, m is an integer from zero to 1, and Z is an integer oxygen, a sulfur atom, a straight or branched alkylene group of 1 to 6 carbon atoms, or a straight or branched alkylene group of 1 to 5 carbon atoms containing not less than one oxygen and/or sulfur atom at the terminal and/or center carbon chain. The compounds of formula 1 constituting the active substance of the agents according to the invention also include compounds of formula 1, in which Rx is a group of formula - NR'a, in which R1 is a lower alkyl group, a cycloalkyl group with 3-5 carbon atoms, lower haloalkyl group, lower alkenyl group, lower alkynyl group, lower haloalkynyl group, alkoxyalkyl group with 1-2 carbon atoms in the alkoxy radical and 1-2 carbon atoms in an alkyl radical, an alkylthioalkyl group with 1-2 carbon atoms in the alkylthio radical and 1-2 carbon atoms in the alkyl radical or a 2-furfuryl group, and W is an oxygen or sulfur atom, and R2, R3, 10 Y, Z, n and m have the meanings given above. The compounds of formula 1 constituting the active substance of the compositions according to the invention include those compounds of formula 1 in which Ra denotes the Ra group denoting a lower alkyl group, a 3-5 cycloalkyl group carbon atoms, a lower alkenyl group, a lower haloalkyl group, a lower cyanoalkyl group, a lower alkynyl group, an alkoxyalkyl group with 1-2 carbon atoms in the alkoxy radical and 1-2 carbon atoms in the alkyl radical or an alkylthioalkyl group with 1- 2 carbon atoms in the alkylthio radical and 1-2 carbon atoms in the alkyl radical, and R2, R3l Y, Z, n and m have the meanings given above. The term "lower group" as used herein refers to an alkyl group, al- kenyl, haloalkyl, cyanoalkyl, alkoxy, alkynyl, haloalkoxy, alkenyloxy, alkynyloxy, alkylthio, alkenylthio, alkylthioalkyl, haloalkynyloxy and alkoxyalkoxy means a group containing up to 8 carbon atoms , preferably up to 5 carbon atoms. Examples of substituents Rx are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tertiary-butyl, tert-butyl, n-pentyl, 1-methylbutyl, cyclopropyl- va, cyclobutyl, cyclopentyl, chloromethyl, bromomethyl, 1-chloroethyl, 2-chloroethyl, 1-chloropropyl, 2-chloropropyl, 3-chloropropyl, vinyl, allyl, methylallyl, dimethylallyl, ethynyl, propargyl, methoxymethyl, Methyl, n-propoximeter, isopropoxyme-45, metoxetyl, etoxethyl, n-propoxetle, isopropoxetic, methylomethyl, ethyl-thistle, n-propylotometh, n-butyliometric, methyteltile, ethylotille, ethylotille, ethylotille, ethylotille, ethylotille, ethylotille, ethyliotyl, ethyliotilowy, ethylotioletyl, ethylotioletyl, ethyliotyl, ethyl, isopropylotio- w ethyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy/isobutoxy, tertiary-butoxy, tert-butoxy, n-pentoxy, cyclopropoxy, cyclobutoxy, cyclobutylmethoxy, and xyl, 1-chloropropoxy, 2-chloropropoxy, 3-chloropropoxy, »[2-bromo-ethoxy, vinyloxy, 3-methylallyloxy, methylallyloxy, propargyloxy, methylpropynyloxy, 4-chloro-2-butynyloxy, methoxyethoxy , 2-ethoxyethoxy, methylthio, ethylthio, n-propylthio, etc. 65 4 Examples of substituents R3 are hydrogen, chlorine, bromine, iodine and fluorine, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, methoxy, ethoxy, isopropoxy, trifluoromethyl, pentafluoroethyl, methylthio, ethylthio, etc. Particularly preferred compounds of formula 1 constituting the active substance of the compositions according to the invention are compounds in which n is 1 and R3 is a substituent in position 3 or 4, compounds in which n is 2 and R3 is a substituent ¬ substituents in position 3 and 4, as well as compounds in which n is 3 and R3 is substituents in position 3, 4, 5. Preferred substituents for R2 are the lower alkyl group, the cycloalkyl group with 3-5 carbon atoms, the lower alkenyl group and the lower alkoxy group. When m is zero, then Z preferably represents an oxygen or sulfur atom, and when m represents 1, then Z preferably represents an alkylene group having 1-3 carbon atoms. Examples of preferred compounds of formula 1 constituting the active substance of the compositions according to; of the invention are N-[3-(3,4-dichlorophenylethoxy)phenyl]propionamide, N-[3-(3,4-dichlorophenylpropoxy)phenyl]propionamide, N^[3-(3,5-dichlorophenyloxymethyl) phenyl]propionamide, N-[3-(2-dichlorophenylethoxy)phenyl]propionamide, N-[3-(2-methylphenylpropoxy)phenyl] propionamide, N-i[3-(3,4-dichlorophenylpropoxy)phenyl ]cyclopropylamide, N-[3-(3-chlorophenylethoxy)phenyl]cyclopropylamide, etc. It has been found that the compounds of formula 1 have a herbicidal effect when applied to treatments before and/or after the emergence of plants, the effect being is particularly strong when applied after the plants have emerged. Compounds of formula 1 are selective towards such crop plants as cotton, soybean, rice, corn, wheat and sugar beets*, therefore they can be used as herbicides on flooded and upland rice fields, in soybean, cotton, sugar beet, corn, wheat, etc., as well as in vegetable crops, etc. These compounds are also suitable for use in orchards, mulberry crops, uncultivated areas, pastures, forests, etc. It has also been found that the compounds of the formula 1 have the ability to prevent and inhibit many plant diseases occurring among useful plants, fruit trees, etc. Examples of diseases in the fight against which the compounds of the formula 1 are particularly effective ¬ susceptible to powdery mildew of apples, pears, grapes, oranges, cucumbers, melons, wheat, etc., downy mildew of grapes, oranges, cucumbers, melons, etc., rust of root crops, e.g. radish and wheat rust, beans, etc.5 Table 1 116 723 G cont. table 1 J Compound number 1 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 1 22 1 23 1 24 25 1 26 | 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 .49 50 51 52 53 54 55 56 Chemical structure of the compound 2 formula 2 formula 3 formula 4 formula 5 formula 6 formula 7 formula 8 formula 9 pattern 10 pattern 11 pattern 12 pattern 13 pattern 14 pattern 15 pattern 16 pattern 17 pattern 18 pattern 19 pattern 20 pattern 21 pattern 22 pattern 23 pattern }24 pattern 25 pattern 26 pattern 27 pattern 28 pattern 29 pattern 30 pattern 31 pattern 32 pattern 33 pattern 34 pattern 35 pattern 36 pattern 37 pattern 38 pattern 39 pattern 40 pattern 41 pattern 42 pattern 43 pattern 44 pattern 45 pattern 46 pattern 47 pattern 48 pattern 49 pattern 50 pattern 51 pattern 52 pattern 53 pattern 54 pattern 55 1 pattern 56 pattern 57 Temperature melting or refractive index | 3 I 124—125°C 122—124°C 91—92°C 65—670C 157—158°C 119—120°C 101—103°C 119—121°C 122—123°C 116—118°C 102-104°C 105-107°C 76-77°C 99-100°C 104-106°C 74-76°C 60-61°C 80-81°C 88-89°C 84-85°C 65—66°C 84—85°C | 74—75°C 69—71°C 100—102°C 86—88°C 60—61°C 96—98°C . 78-79°C 59-60°C 126-128°C 95-96°C 115-116°C 120-122°C 113-114°C 103-105°C 116-117°C 109-110°C 103—104°C 67—69°C 109^110°C 95—96°C 123—124°C 99—101°C 92—93°C 102—103°C 99—100°C n^ 1.5867 90—91°C 75—76°C 73—74°C 57—58°C 47—49°C 59—61°C 82—83°C 52—53°C 57 58 59 60 61 62 63 64 65 66 67 68 69 70 71 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86 87 88 89 90 91 92 93 94 95 96 97 98 99 100 101 102 103 104 105 106 107 and 108 109 110 111 112 113 114 115 pattern 58 pattern 59 pattern 60 pattern 61 pattern 62 pattern 63 pattern 64 pattern 65 pattern 66 pattern 67 pattern 68 pattern 69 pattern 70 pattern 71 pattern 72 pattern 73 pattern 74 pattern 75 pattern 76 pattern 77 pattern 78 pattern 79 pattern 80 pattern 81 pattern 82 pattern 83 pattern 84 pattern 85 pattern 86 pattern 87 pattern 88 pattern 89 pattern 90 pattern 91 pattern 92 pattern 93 pattern 94 pattern 95 pattern 96 pattern 97 pattern 98 pattern 99 pattern 100 pattern 101 pattern 102 pattern 103 pattern 104 pattern 105 pattern 106 pattern 107 pattern 108 pattern 109 pattern 110 pattern 111 pattern 112 pattern 113 pattern 114 pattern 115 pattern 116 85—87°C 48—51°C ng 1.5768 n2D4 1:5828 n" 1.5919 n2D5 1.3926 n^ 1.5009 ng'5 1.5948 88—89°C 138—140°C 141—143°C 81—82°C 59—60°C 75—76°C 61—63°C 83—84°C 109—110° C 105—107°C n^'5 1.5637 94—96°C 112—114°C 131—133°C 79—80°C 79—80°C n^l.55t98 70—71°C 143— 145°C 66—67°C 59—60°C 127—130CC 149.5—153°C 134.5—137.5'°C 101—102°C n^ l;5520 nJJ 1.5585 97—100 °C 98—99°C 122—123.5°C n^° 1.5542 79—80°C 88—90°C 84—87°C 56.5—58.5°C 104—106.5° C 60.5—62°C 103—105°C 105.5—108°C 112—115.5°C 99—99.5°C 117—118°C 144—146.5°C 148.5— 151°C 106—107°C 85—86°C 83—84°C 104—105°C 111—114°C n^'5 1.5643 n^ 1.5732116 7 cont. table 1 1 1 116 117 118 119 120 121 122 123 124 125 , 126 , 127 128 129 130 131 132 133 134 135 136 137 138 139 140 | 141 1 142 143 144 145 1 146 147 148 149 150 151 and 152 153 154 155 156 157 158 159 160 161 162 163 164 165 166 and 167 168 169 f 170 171 172 173 1 J 2 pattern 117 pattern 118 pattern 119 pattern L20 pattern 121 pattern 122 pattern 123 pattern 124 pattern 125 pattern 126 pattern 127 pattern 128 pattern 129 'pattern 130 "pattern 131 pattern 132 pattern 133 pattern 134 pattern 135 pattern 136 pattern 137 pattern 138 pattern 139 wzpr 140 pattern 141 pattern 142 pattern 143 pattern 144 pattern 145 pattern 146 pattern 147 pattern 148 pattern 149 pattern 150 pattern 151 pattern 152 pattern 153 pattern 154 pattern 155 pattern 156 pattern 158 pattern 159 pattern 160 pattern 161 pattern 162 pattern 163 pattern 164 pattern 165 pattern 166 pattern 167 pattern 168 pattern 169 pattern 170 pattern 171 pattern 172 pattern }73 pattern 174 1 3 1 79—81°C 55—56°C 100—101°C n^'5 1.6044 n*J ,1.6090 73—75°C n**'5 1.6091 147—148°C 63—65°C 96—98°C n^ 1.6046 n£'5 1.5895 InJJ 1.5972 75—77°C 66—67°C 91—92°C 83 —85°C n22'5 1.5955 86—87°C 128—131°C 111—113*C 60—62°C 78—79.5°C n*J'5 1.5631 66.5—68 ,5°C n2?' 5 1.5661 | 98.5—100°C 56.5—58°C 74^75°C n£ 1.56.62 | 52„5—54°C 1 ng'5- 1.5628 1 94— 96°C 91—92°C 108.5—LI0.5°C 95.5—97°C 56—57° 65—67°C 97—98y5°C 91—93.5°C 63—65°C 103—104°C 88—90°C rip7 1.577.2 83—85°C 94—95°C 123—124°C 80—81°C n2]'5 1.5529 ng 1.5661 n2D5.5 1, 59(12 102.5—104°C 83—85°C 77—80°C 104—107°C ng'5 1^712 n2* 1.5653 42-45°C | 8 continued table 1 1 1 174 175 1 176 177 178 179 180 181 182 183 184 185 186 187 188 1 189 1 190 191 192 193 194 195 196 197 198 199 200 201 202 203 2 04 205 206 207 1 ^ pattern 175 pattern 176 pattern 177 pattern 178 pattern 179 pattern 180 pattern 181 pattern 182 pattern 183 pattern 184 pattern 185 pattern 186 pattern 187 pattern 188 pattern 189 pattern 190 pattern 191 pattern 192 pattern 192 pattern 193 pattern 194 pattern 195 pattern 196 pattern 197 pattern 198 pattern 199 pattern 200 pattern 201 pattern 202 pattern 203 pattern 204 pattern 205 pattern 206 pattern 207 pattern 208 1 3 1 115—116°C I 70-73°C n2^ 1.5550 n2D9.51.5863 j I n2^ 1.5839 ! 140—140.5°C 1 104 -106°C 1 141^144.5°C 133„5—127°C ! 101—102°C j 114—115.5°C 101—103°C 1 103—104°C 124—126°C 85—86°C 120-121 °C | 121—122°C 1 90—92°C 109—110.5°C 104-105°C 80-85°C ng 1.5643 128—132°C 85—86°C 110.5—112°C 111 ,5^114°C 91—93°C 112—113°C 78—80°C 78.5—79.5°C 81—84°C n2^ 1.6158 91.5—92°C 106—107 .5°C Compounds of the formula I have particularly beneficial preventive and inhibitory effects in the case of rust diseases such as barley and wheat rust caused by Puccinia striiformis, wheat leaf rust caused by Puccinia recondita, oat crown rust caused caused by Puccinia coronata, bean rust caused by Uromyces sojae, bean rust caused by Uromyces appendiculatus and coffee rust caused by Hemileia vastatrix. that they act not only preventively, but also curatively. Therefore, compounds of formula 1 can be used not only as herbicides, but also as fungicides. The simultaneous herbicidal and fungicidal action of the compounds of formula I can be expected especially in rice crops in flooded and upland fields, cotton crops, soybeans, corn, wheat, barley, etc. The table shows examples of some of the compounds of formula I constituting substances116 723 10 active herbicides and fungicides according to the invention. The compounds of formula 1 are used in the form of preparations such as wettable powders, emulsifiable concentrates, granules, fine granules and dusts. Solid or liquid carriers may be used to prepare these preparations. Examples of solid carriers are powdered minerals, e.g. kaolin, bentonite, clay, montmorillonite, talc, diatomaceous earth, mica, vermiculite, gypsum, potassium carbonate and apatite, powders of vegetable origin. , e.g. soybean powders, flour, wood flour, tobacco powder and crystalline cellulose, macromolecular compounds, e.g. petroleum resins, polyvinyl chloride, damara and ketone resins, and aluminum oxide, wax, etc. As thin carriers can be use alcohols, e.g. methanol, ethanol, ethylene glycol, benzyl alcohol, aromatic hydrocarbons, e.g. toluene, xylene and methylnaphthalene, halogenated hydrocarbons, e.g. chloroform, carbon tetrachloride and chlorobenzene, ethers, e.g. dioxane and tetrahydrofuran, ketones, e.g. acetone, methyl ethyl ketone and cyclohexanone, esters, e.g. ethyl acetate, butyl acetate and ethylene glycol acetate, acid amides, e.g. 25 N,N-dimethylformamide, nitriles, e.g. acetonitrile, alcohol ethers, e.g. ethylene glycol ether, water, etc. Any non-ionic surfactants can be used as surfactants for emulsification, dispersion or dusting. , anionic, cationic or amphoteric. Examples of such agents are polyoxyethylene alkyl ethers, polyoxyethylene alkyl aryl ethers, polyoxyethylene fatty acid esters, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, polyoxyethylenes, polyoxypropylenes. , polyoxyethylene alkyl phosphates, salts of fatty acids, alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates, alkyl phosphates, polyoxyethylene alkyl sulfates, quaternary ammonium salts, etc. Optionally, gelatin, casein, sodium alginate, starches may be used as auxiliary agents. , agar, polyvinyl alcohol, etc. Below are examples of herbicidal and fungicidal preparations containing compounds of formula 1 as active substances. Example I. 8 parts by weight of a compound of formula 29 or 73, 5 parts by weight of polyoxyethylene alkyl aryl ether and 15 parts by weight synthetic hydrated silicon dioxide is mixed thoroughly and pulverized to obtain a wet powder. Example II. 30 parts by weight of the compound of formula 37 or 159, 7 parts by weight of polyoxyethylene alkyl aryl ether, 3 parts by weight of alkyl aryl sulfate and 60 parts by weight of xylene are mixed thoroughly to obtain an emulsifiable concentrate. Example III. 1 part by weight of the compound of formula 24 or 161, 1 part by weight of white carbon, 5 parts by weight of lignosulfonate and 93 parts by weight are mixed thoroughly and powdered, then thoroughly mixed with water, granulated and dried to obtain granulates. Example IV. 40 parts by weight of bentonite, 5 parts by weight of lignosulfonate and 55 parts by weight of clay are mixed thoroughly and powdered, then thoroughly mixed with water, granulated and dried, obtaining granules without the active substance. The granules are then saturated with 5 parts by weight of the compound of the formula 52 or 164, obtaining granules. Example V. 3 parts by weight of the compound of the formula 61 or 175, 0.5 parts by weight of isopropyl phosphate, 66.5 parts by weight how many and 30 parts by weight of talc are mixed thoroughly and powdered to obtain dust. Compounds of formula 1 can be used together with other herbicides to enhance their action, and in some cases a synergistic effect can be expected. Examples of such herbicides are those from the group of phenoxyalkanecarboxylic acids, e.g. 2,4-dichlorophenoxyacetic acid, 2-methyl-4-chloro-phenoxyacetic acid and 2,4-di-chlorophenoxybutyric acid (and their salts and esters), agents from the group diphenyl ethers, e.g. 2,4-dichlorophenyl-4'-nitrophenyl ether, 2,4,6-trichlorophenyl-3'-methoxy-4'-nitrophenyl ether and 2,4-dichlorophenyl-3'-methoxycarbonyl-4 '-nitrophenyl, agents from the triazine group, e.g. 2-chloro 4,6-diethylamino-1,3 5-triazine, 2-chloro-4-ethylamino_6-isopropylamino-1,3 5-triazine, 2- methylthio-4,6-diethylamino-1,3,5-triazine and 2-methylthio-4,6-di-isopropylamino-1,3,5-triazine, agents from the triazinone group, e.g. - no-6-phenyl-1,2 4-triazin-5(4H)-one and 3-(methylthio)-4-amino-6-III butyl_1,2,4-triazin-5(4H)-one, agents from the urea group, e.g. 1,1-dimethyl-3--(3,4-dichlorophenyl)urea, 1-methoxy-1-methyl- - 3(3,4-dichlorophenyl(urea, 1,1-dimethyl-3- -(3-chloro-4-difluorochloromethylthiophenyl(urea, 1,1-dimethyl-3-[4-4-chlorophenoxy)phenylol] urea and 1,1-dimethyl-3-(3'-trifluoromethyl(phenylurea, carbamate agents, e.g. phenyl(methyl carbamate and 4-chloro-2-butynyl m-chlorocarbamate, thiolcarbamate agents, e.g. S-(4-chlorobenzyl) N,N-diethylthiocarbamate, S-ethyl N,N-hexamethylenethiolcarbamate and S-ethyl dipropylthiolcarbamate , agents from the group of acid anilides, e.g. 3, 4-dichloroproponanilide, N-methoxymethyl-2, 6-di-ethyl-2-chloroacetanilide and 2-chloro-2', 6'-diethyl--N-(butoxymethyl)acetanilide , agents from the uracil group, e.g. 3-second-butyl-5-bromo-6-methyluracil and 3-cyclohexyl-5,6-trimethyleneuracil, agents from the pyridinium salts group, e.g. bis(l) dichloride -methyl-4-pyridine), agents from the group of organophosphorus compounds, e.g. N-(phosphonomethyl)glycine, N-II-rt. butylamide116 723 11 12 0-ethyl-0-2-nitro-5-methylphenyl phosphorothioate and O-methyl-0-2-nitro-4-methylphenyl phosphorothioate N-isopropylamide, agents from the toluidine group, e.g. -dinitro-4-trifluoromethyl-N,N-dipropylaniline and 2,6-dunitro-4-trifluoromethyl-N-cyclopropylmethyl-N-propylmethyl-N-propylaniline and N-II-rt. butyl-4-III butyl-2,6-dinitroaniline, 3,5-dinitro- 4-N,N-dipropylaminosulfanilamide, 5-III butyl-3(2,4-dichloro-5-isopropoxyphenyl-1, 3, 4-oxadiazolinone-2, 2,2-dioxide 3-isopropyl-1H-2, 1, 3-benzothiadiazin-4(3H) )-one (and its salts), -diethylpropionamide, 3-amino-2,5-dichlorobenzoic acid, 2-butyl-4,6-dinitrophenol, N-l-naphthylalamide acid, 5-amino-4- chloro-2-phenyl-3(2H)-pyridazinone, sodium salt of 2-i[1-(N-aryloxyamino)butylidene]-5, 5^dimethyl-4-methoxycarbonylcyclohexanedione-1,3,(±/- Methyl 2-[4-)i2;4-clwuchlorophenoxy]propionate, (±/-2-j[4-)3,5-dichloro-2-pyridyloxy/phenoxy]methyl propionate, sodium salt of 2- -< [4-(3,5-dichloro-2-pyridyloxy)phenoxypropionic acid, etc. The compounds of formula 1 can also be used together with fungicides, microbiological insecticides, pyrethroid insecticides and other insecticides, with plant growth regulators or fertilizers. Examples of fungicides that can be used together with compounds of formula 1 are 1,2-dimethylcyclopropane dicarboxylic acid N-(3,5-dichlorophenyl)imide-1,2, N-3-pyydylimidodithicarbonate S-n-butyl-S-p-III-row butylbenzyl, 0,0-dimethyl-0,2,6-dichloro-4-methylphenyl thiophosphate, methyl N-benzimidazolyl-2-N-(butylcarbamyl) carbamate, cyclohexene-4-dicarboxylic acid N-trichloromethylthioimide-1,2, cis-N-(1, 1, 2,2-tetrachloroethyl)cyclohexene-4-dicarboxylic acid-1,2 thiomide, polyoxin, streptomycin, zinc ethylene-bis-dithiocarbamate, zinc dimethylthiocarbamate, ethylene- manganese bis-dithiocarbamate, bis(dimethylthiocarbamyl) disulfide, tetrachloroisophthalonitrile, 8-hydroxyquinoline, dodecylguanidine acetate. 2-methyl-5,6-dihydro-1,4-oxathin-carboxylic acid-3 anilide, N'-dichlorofluoromethylthio--N,N-dimethyl-N'-phenylsulfonamide, 1-(4-chloro-phenoxy)-1 -(1,2,4-thiazolyl-1)-3,3-dimethylbutanone-2,1,2-bis)3-methoxycarbonyl-2-thioureido)benzene, etc. Concentration of compounds of formula 1 in weedicides and fungicides according to the invention is generally 1-80% by weight. In practice, the application rate of the agents according to the invention as herbicides is 2-200 g/are, preferably 5-30 g/are, and as fungicides preferably 0.2-10 g /ar. As shown in the examples below, the compounds of formula 1 have low toxicity towards crop plants and have a strong herbicidal and fungicidal effect, and they constitute excellent selective herbicides. ¬cidal. In the tests described in the examples, the control compounds used were fluometuron (compound of formula 209), basagran (compound of formula 210), propanil (compound of formula 211), swep (compound of formula 212), chloramben (compound of formula 213), diulon (compound of formula 2ll4\ MCP (compound of formula 215) and triforine compound of formula 216). Example VI. Herbicidal effect when treated after the plants have emerged. An emulsifiable concentrate containing the compound of formula 1 as an active substance was prepared (using the procedure given in Example II) and sprayed on plants grown in a greenhouse with a height of 5-15 cm, to obtain the dose of the active substance given in tables 4 and 5. Spraying was carried out using 5 liters of the preparation per 1 are. After 3 weeks, the herbicidal effect and damage to crop plants were assessed by comparing the weight of the aerial parts of the treated plants in their fresh state. and analogous weight in the case of control plants. During the evaluation, the criteria given in Table 2 were used. Table 2 Index 5 4 3 2 | 1 0 Weight of plants in a fresh state 1 (percentage in relation to the weight of control plants) in % weeds 0 1— 10 11— 20 21— 40 41— 60 61—100 useful plants 0—39 40—59 | 60—79 r 80—89 90—99 | lt0 [' Indicators 5 and 4 were generally taken to reflect a sufficient degree of weed control, and indicators zero and 1 to reflect proper protection of useful plants. Identical indicators were also used in the tests in further examples. The test results are given in the tables 3 and 4. Example VII. Test of herbicidal effect during treatment before plant emergence. Wagner pots (ii) 50000 ara) were filled with soil from upland fields and seeds of cotton, soybean, corn, wheat, rough amaranth (Amaranthus retroflexus), and quinoa (Chenopodium) were sown in individual pots. album), purslane (Portulaca oleracea) and red fingerling (Digitaria sanguinalis). Weed seeds were sown at a depth of 0.3-0.5 cm, and useful plant seeds were sown at a depth of 2-3 cm. A specific amount of wettable powder containing the tested compound was dispersed in water and the suspension was sprayed over the entire soil surface using 30-50 g of active substance per 1 are. After the procedure, the pots were placed in the greenhouse, and after 24 25 \ 26 27 28 29 30 31 | 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 1 48 49 50 51 52 53 54 55 1 56 | Dose of active substance in g/are 2 1 20 .20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 . 20 20 20 20 20 20 20 20 20 20 20 20 | Herbicidal effect 1 - one-sided weed 1 ~3 1 4 4 .5 5 4 4 4 4 4 4 ' 4 4 4 3 4 4 3 5 4 5 4 4 4 4 5 5 4 4 4 4 4 4 4 4 1 4 5 5 5 5 4 5 4 5 5 4 4 4 4 4 4 4 4 4 1 4 1 5 5 1 radish |_4 1 5 5 5 5 5 5 5 5 5 4 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 4 5 5 5 5 4 5 5 4 5 5 5 5 4 5 4 5 5 4 4 4 5 5 | rough quack 5 5 5 1 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 4 5 5 5 5 5 5 5 5 5 5 4 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 4 5 5 5 * 1 Ko- 1 white mosa | 6 1 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 | 5 1 5 5 5 5 5 5 5 5 4 5 5 5 5 5 5 5 5 5 1 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 1 14 cont. table 3 1 1 57 58 59 60 61 62 63 64 65 66 67 68 69 70 71 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86 87 88 89 90 91 92 93 94 95 96 97 98 99 100 101 102 103 104 105 106 107 108 109 110 111 1 112 113 114 115 116 1 117 LUU- 20 20 20 20 20 20 20 20 20 .20 20 20 20 20 20 20 20 20 20 20 20 20 20 1 20 1 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 .20 1 * 5 5 4 5 ' 4 4 4 4 1 5 1. 5 ¦ 5 4 4 1 4 1 4 4 5 5 3 3 3 3 5 3 3 4 5 5 4 5 4 4 4 5 4 4 4 5 4 4 3 " 4 5 5 5 5 4 4 5 4 3 3 5 . 5 3 5 4 5 4 5 J 5 1 UL. 5. 5 5 5 5 5 5 5 5 5; 5! 5 5 5 5 5 5 5 5 5 5 4 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 4 5 5 5 5 5 4 5 5 ¦ 5 .5 5 5 5 5 5 5 .5 . 5 5 5 5 ,' 5 5 5 5 ¦ 5 -. 4 4 5 5 5 5 5 .5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 ¦ '5 ¦ 5 5 5 5 5 5 5 5 5 '5 5 5 1 UJ 5 5 4 5 .5 5 .5 5 5 .5.. -5 .5 5 5 5 5 5 5. 1 4 1 5 5 4 5 5 % 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 .5 5 515 continued table 3 16 continued table 3 118 1(19 120 121 122 123 124 126 126 127 128 129 ISO 131 132 133 134 136 136 137 188 139 140 141 142 143 144 145 146 147 148 149 150 IM. 152 153 154 155 156 157 158 159 160 161 162 163 164 165 166 167 188 169 170 171 172 173 174 175 176 177 178 20 20 20 20 20 20 20 20 20 20 20 20 '20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 20 ^20 20 20 20 20 20 20 3 3 3 3 3 3 3 3 3 4 3 4 4 4 3 3 5 4 3 5 5 4 5 5 5 3 4 3 5 3 5 3 3 4 4 3 3 3 5 4 4 3 5 5 5 5 5 5 5 3 5 5 5 5 5 5 5 4 3 3 3 4 4 4 4 4 3 4 4 4 5 5 5 5 5 5 5 5 5 4 5 5 5 5 5 5 4 5 5 5 4 5 5 5 5 5 5 5 5 5 5 5 4 5 5 5 5 5 5 5 § 5 5 5 5 5 .5 5 5 5 4 4 5 4 4 4 4 5 5 5 5 5 4 5 5 5 4 4 5 5 5 5 5 5 5 5 5 5 5 5 5 4 5 5 5 5 5 4. 4 4 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 4 4 4 4 5 4 5 4 4 4 4 5 4 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 4 5 5 5 5 5 5 5 5 5 5 5 5 5 4 5 5 5 5 5 10 15 20 25 30 35 40 45 50 W 179 180 iai 182 183 184 185 186 187 188 189 190 191 192 193 194 195 196 197 198 199 200 201 202 1 203 20 20 20 20 20 20 20 20 20 20 20 20 2 0 20 20 20 20 20 20 20 20 20 20 20 20 6 3 I 5 I 4 I 5 3 5 I 4 I 5 3 I 5 I 4 I 5 5 5 5 5 5 I 5 I 5 5 5 I 5 I 5 5 5 j 5 I 5 I 5 5 I 5 I 5 I 5 5 I 5 I 5 I 5 5 I 5 I 5 I 5 5 5 5 5 5 I 5 I 5 5 5 I 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 I 5 4 I 4 I 5 I 5 5 I 5 I 5 I 5 4 I 5 I 5 5 5 I 5 I 5 || 5 5 5 5 II 5 5 I 5 5 'I 5 5 5 5 5 05 wie 3 weeks herbicidal effect and damage to crop plants were assessed. The test results are presented in Table 5. Example VIII. Test in flooded rice fields. Wagner pots (1) 5000 ares were filled with soil from flooded rice fields containing weed seeds, placing 1.5 kL of soil in each pot. The pots were kept flooded. Rice seedlings at the three-leaf stage were planted into the pots and the pots were placed in a greenhouse. After 15 days, the required amounts of the tested compounds were introduced into the water covering the soil in the pots using emulsifying concentrates diluted with water. After 25 days after the procedure, the degree of damage was assessed using the indicators given in Example VI. The broadleaf weeds used in the test were Monochoria viaginalis, Linderna pyxidaria and Rotala indica Koehne, and Cyperus difformis. The test results are presented in table 6. Example IX. Protective effect against wheat leaf rust. Wheat variety Nohrin No. 61 were grown in a 9 cm diameter flower pot to the monoleaf stage, infected with Puccinia recondita and placed in a humidification chamber. After 18 hours, the plants were sprayed with aqueous suspensions of emulsifiable concentrates containing the tested compounds, using 15 ml of suspension per pot. The pots were placed in a humidification chamber at a temperature of 20°C and grown under the light of a fluorescent lamp for 10 days. i-H BUJBZD B^UBTSd iii B^Bia BSOUIO^I T2j;SIOZS ;bjjbzs Mapi -pozH ? ^H Bzp^J BOiuazsj iCMOj^no ^Bjne etos BUfaMBg JB/S AV Cauu^zo iCouBlsans B^MBa ri^ZBTMZ lauunN H rH rH CO rH O OS CO t^ co lO ^ co - 1T 116 723 18 Tt* rt * co ^ -^ co -^ co cyj t^ co co... rf t^ co m io t& ^ co co 10 ^ jo io . ^ .tj< .m ^ ^ m^eoiri^Tf m^n in^M.mww ift.^co m^co m:^M io^co mcoM tn^co io^co ¦"tfjcocoip^co.in^ co i/Jmco m^eo m m ^ m m "3< mi rf co ioiOt^ io^co irt^^ m^co up.-^co lOioio m m -"tf1 lO^Mn^w^mw^-; mioio io ifl io lom^mmco m w -m ¦ m m-m m io in m w m w. w f m io io w w m icioio m in m m io m lomip inmm mmm mmmmm 1 io io in m*om m lq io mmm mmm mmm to ^ *0 m m in in m m m.m ] mmm mm^mm^mm^mm^mm^mio^^ioi^mm^miojioin^ miom mmmmmi «^^^ mmm mmm mmm mmin mmmmmm o o ' | oo[ oo| oo| oo| m^h| oo | f-«o| i-«o| i-i,-,] «h| Ml N | H.o-I He| | .| | « r. | - o | | | | - o | «-|||| -o||||~o||||oo||11«-|~°l hh|hh| | | | | | |«h| | | | ho| | | | | | | | | | | 1 i-h o ' | o o | o o | |||^o|i-Ho|rHo|oo|oo|cMo| ,-H rH | rH © | 00| O © | rH rH | 00| rH rH | rHo| Oo | rH © | oomoomoómoomoomoomoomoomoomoom 1 N H CN r-( W H N H CNrH N H M H N H N H N H ¦ l.CO^C^CNCOiOCOt^-. OOrH 1 rH rH CS] CO CO CO cont. table 4 CO i »—t 00 1—1 9 | 10 / 11 1 co r co iO M CO Cl io ^f 't iw* Tt* m to w n inioco m m ^ ^t^co lo ifl^nf^nM^^nio^Mio^nioionio LnioTP^Pon^^nio^ TjtiCTfTfiLn^Mm io ifl ^ lo lo lo mT^rf* io m ^ io lo rt* io lo co lo LO lO lo lOlOlO lOlOTj* LO rj< Tf lO irt ^ IOLOlO LO io m 10 n m io lo lo m lo lo lo then lo lo lo lo lo lo lo lo m in Tjl m m ^ lo lo lo lololo lo lo lo io lOioioinlOTfioioicioiOT^ioiOTflioioiOLC lo lo lo m in m io lo tH m m ^ lo lo lo o lo lo lo oo| oh| oh| you *-» | oh| what| o C4 o | «-and about | |||oi-i|oo|e^o| | |||eo|oo|^.e| | | | ~ o | | |! | |||^^|rtrt|^0| and | | H oo[oo|oo|^o|cio|-H— | | T-ne| O O LO O O LO OOiO O O LO OOlO OOlO O Cl -^ C^l -i—t Cl ^h CO LO O LO t^- o CO ¦^ "^ LO lO LO CC tO LO ^ LO Tf* TJ* LO Tjl Tf lO TH TF LOTt^OO LO^Tt* rl«-^ 't W M rf ^ CO ^ CO CO T^rt^CO ^ tH ^ LOTt* t^t^CO LOt^t^ LO "^ CO rjl^eo LO LO what LO LO LO LO LO LO lolOlOlOlOlOlOlOlOlOlOlOlOlOlOlOiO «=I1IIIMIIIII|oo| |llll! °o||MM|oo| | 1 o o | - o | | | | -o| ho| 1 o|-oi! l||IMMlll || |lloo|oo|-o|c.o| | | o e | || |8o|ho|h0| OlOOOlOOOlOOCJLOOOlOOOlO T-t ci ^ ci —< ci —< ci ^ cq^H ci co tP en <= t- t- L t*- C021 116 723 22 .o irt ^ co m in eo w ^ m ^ m w .^ ^ po lo m co m ^ co lo ^ co io i< ^ m ^ co . ^ ^ co iot^-^ rt< CO PO ^ ^ M «^ PO CO t^^CO LO r*< ^ t^^CO lO^"^ lo LO CO lO CO CO LO-^CO -^r^CO lO ^ Ifl Ifl ^ CO lO*^4^ rf< PO PO ^ fO P3 lOTfiOm^rM lOlOCO K3 ifi CO lO^OO ^ CO CO lO ^ CO W ^ CO lo lo lo ifl io ifl m w io io io to io io m lo io io io m m lo m io lo io lo w m m m m m io io ^ io in io ioioio m m m lo ito m io w io Lomio.io»oio_iowio.ioiaio w m w m lo lo io io lo io iA irj lo m lo io w w. w w w io lo m lo io lo m m mi ifl io m lo io lo m m m io io io lo lo lo io io lo lo lo lo m m m m m w m w m io io m io lo io io lo io lo io io m m f lo lo io lo io io lo lo lo lo lo lo lo lo lo lo lo io. m m m io lo io lo lo lo lo lo lo io m io mioio m in io m w ic io ifl ifl in m io lo io io irjiofo in m m lo io lo io lo lo io lo m in lo m m ic ifl w io w lo lo lo III | | | oo | || I 111=° ,-H O O O I I I I I I I I I I I - -I © ,H © I I I I I O © © O I I o o II MIII IM | | |oo|o=| I I I - o I o o I Ml Ml © © —< © I I I - o I I I I - o I I I I IM Ml l © i^H © lo <5 © ©om © © io ©©to © © io ©©io ©©lo ©©lo ©©lo ©©lo ©©lo ©©lo ^ H (N H (MrH CO 05 C\J o cq ©23 116 723 24 o ci m n* cv ic Tjt ^ m^fco »o ^ co in id ^ lo ¦ «# rt* irt ^ co m ^ ^ io ^ co io^-^ in iw* co torM^ mTf ? 0 iC^W ift CO M "^^CO m tF CO lC ^ W lO CO CO lO rj* CO iClOCO lO rt4 CO TfTl ift M CO m t+* CO t? 4 t*4 CO Tt< CO CO m tP CO lO ifi CO lO ^ CO l/J-r^rt4 ift lC CO lO-^CO ifl rf CO m Tl* tP lo m io in io dzii io io io tnirtLO mmio io m mi ic w io ic m in io in m m m m m m lo ifl w in io m io w ic i mioirt w mi ifl mmio lomio m m mifi io m m io io iOlolo inioio m io m in m kO w m io irj ifi ic m m m m mi ift mmio io ifli ifi icioio m m in m io m m m m toicio io io io LOirjTjl m m io ic ic m mifi ic m m io m m in lo m mtoio m m io io m m m m m ms »^ lo io io io ic io iffi ifti/jift mi ifi io m io ifl »nioic m m m iniem icioic ia id io m m tn tn m io Lomirs lo m m m ic ic m m i^ m ^ ^ io m m iciom icicio mioic io m ic to mm o o o I I I I I I I II II I 1 I I I I I V M I I I - o i i i i i ^H O O O I I I I I I l-»l I II I I I I I I I I I MMMM | | <-H C | O O | O O I -» o I o o —i O i-H O o I I M M I I -o I I I I I 1 I I I I I I I I I I -* I I I I I I I oom oom oom oom o ó ic oom oom oom oom oom o o m oom t*h CC Oi cc co oo25 m ^ co m ^ ^ 10 rj< co lo-^co rt^^co m rH CO lO"^^ ^ Tf CO ^«^C0 m ^ CO . m ^ co 10 ^ co ^ co co ic^eo ^ co co w ifl w mmio lomm irtioio m m ^ 116 723 26 o o o i5 ^ ^ M O H ¦ O lO lO lO IO u*5 lO lO lO ift lO lO LO lO lO io lO m iO iO ^ icioio m m m mioiomiom m m mifi lO lO irtioioiou^m mioio m io in ioioio lO lO lO minio ioioio ifi in io ioioin lOioiolioinio io m mio io io io io io io m m m in m m m -^ cm I I III III III III I I o o Ml i-t O *-» O | O O I I I -= I III II I I « « | io ooio o o m ooio oom o o io O) 1 ° 5 5 rt w rt PP a o S-( FU CO116 723 27 28 Table 5 Compound number 7 25 36 38 43 45 50 5(5 60 73 80 81 112 137 158 161 163 172 185 196 201 Chloramben Diuron Dose of active substance in g/are 50 30 50 30 50 30 50 30 50 30 50 30 50 30 50 30 50 30 50 30 50 30 50 30 50 30 '50 30 50 30 50 30 50 30 50 30 50 30 50 30 50 30 20 10 20 10 Cotton 0 — 0 — 0 — 0 — 0 — ¦ 0 — 0 — 0 — 0 — 0 — 0 — 0 — 0 — 0 — 0 _ 0 — 0 — 0 — 0 - 0 - 0 - 4 - 3 - Soybeans 0 - 0 - 0 - 0 - 0 - 0 - 0 - 0 - 0 - 0 - 0 - .0 - 0 - 0 - 0 - 0 - 0 - 0 - 0 — 0 — 0 — 0 — 5 — commercial Corn 0 ! — 0 — 0 — 0 — 0 — 0 — 0 — 0 — 0 — 0 — 0 — 0 — 0 — 0 — 0 — 0 — 0 — 0 — 0 - 0 - 0 - 3 - 5 - Wheat 0 - 0 - 0 - 0 - 0 - 0 - 0 - 0 - 0 - 0 - 0 - 0 - 0 - 0 - 0 - 0 - 0 - 0 - 0 — 0 — 0 — 1 — 5 — Weeds | Rough amaranth 4 3 5 4 5 4 5 4 5 4 5 4 5 5 5 5 5 5 5 5 5 4 5 3 5 3 5 4 5 5 5 5 5 5 5 5 4 5 3 0 4 and 5 5 2 2 5 5 White quinoa 5 4 5 3 5 4 4 3 5 4 4 3 5 5 5 5 5 4 5 5 5 4 4 4 5 5 5 4 5 5 5 5 5 5 5 5 5 4 5 4 5 5 2 1 5 5 | Purslane 5 4 5 3 4 4 5 4 5 5 5 5 4 3 5 5 5 5 5 5 5 4 4 3 5 4 5 4 5 5 5 5 5 5 5 5 5 4 4 4 5 5 5 5 5 5 Bloody finger 4 3 3 .3 3 3 4 4 4 3 3 3 4 [ 4 5 4 4 3 I 4 3 3 3 3 3 ' 4 3 3 3 4 3 4 4 4 4 4 3 4 3 3 3 E 4 i. 3 3 2 5 4 [29 116723 30 Table6 cont. table 6 1 1 175 132 186 188 193 198 201 MCP Pro- panil Swep 2 40 20 40 20 40 20 40 20 40 20 40 20 40 20 20 10 20 10 20 10 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 8 1 0 (0 0 | 4 4 3 4 4 ' 4 4 ¦ i3 1 3 4 3 4 1 3 ! 4 4 4 3 3 3 3 2 5 5 5" ¦ 5 ¦ 5;" 5 5* 5 : 5- ' 5'" 5 " 5 ' 5 5 5 5 5 4 3 5 4" ¦ ¦ 6 5 5 ¦ 5 5 5 . 5 ; 5 : 5 -\ 5 5 5 \ 5 " 5 5 5 5 2 1 0 5 ; 4 ;| J number [compound 1 1 7 1 1 18 1 25 J 38 "i i 4i 1 I 43 50 j 55 5(7 60 1 68 1 79 82 85 1 91 95 1 100 J | 104 1 ] 109 1 J 115 J 135 j 139 1 1 144 A 152 i 1 161 1 164 i 1 Active substance dose in g/are 2 40 20 40 20 40 20 40 20 40' 20 40 ¦ '20 40 20 40 20 4 0 20 40 20 40 20 40 20 40 20 40 20 40 20 40 20 40 20 40 20 40 20 40 20 40 20 and 40 20 40 20 40 20 40 20 40 20 Crop Rice 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 o ¦ 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 Weeds Weeds one-sided | 4 3 3 4 3 3 1 3 1 3 3 5 5 5 3 3 3 5 5 5 4 5 4 $ 4 4 3 4 3 3 3 3 3 I 3 1 3 4 4 4 4 5 4 4 4 3 3 3 3 4 |3 4 3 5 4 5 4 Broad-leaved | 5 5 5 5 5 5 4 5 5 5 5 5 5 5 1 4 5 5 ¦5 5 5 5 5 5 5 5 5 5 5 5 1 5 5 . 5 5 5 5 5 5 5 5 5 5 , 5 5 5 5 5 5 5 5 5 5 5 5 Cibara 1 6 I 5 5 5 5 5 4 1 5 4 5 5 5 5 5 4 5 5 5 5 5 5 5 5 5 5 5 5 5 4 5 5 1 5 1 5 5 5 5 5 5 5 5 5 5 5 5 4 5 5 5 5 5 5 5 5 Disease index 0 1 2 4 1 8 Infection status j No infection outbreak on! the examined leaf; \\ Less than 10 outbreaks of infection on the examined leaf; ' 11-20 outbreaks of infection per! examined leaf: j 21-50 foci of infection on the examined leaf; \ Above 51 ognjhsk infections! on the examined leaf j Number of compound i 1 3 5 7 9 10 12 15 16 17 24 27 1 31 35 37 Table 7 Concentration of the active substance in parts per million 2 500 500 500 500 500 500 500 500 500 500 500 500 500 500! 500 and ,; | i , L i ^ ( severity of m disease j I in% 1 ¦ H ; 3 : ' -8.0 ! 0„0 10.0 0.0 3.8 9.5 . 8.8 0.0 0.0 7.5 0.0 0.0 | 0.0 1 3.4 0.0 [116723 31 32 1 1 38 39 1 44 45 50 63 1 65 I 68 71 1 72 73 74 80 85 90 91 95 | 97 99 105 1,107 1,108 1,109 1,134 | 137 j 139 1,140 I 147 I 148 1,151 152 156 i 157 161 162 165 174 179 188 190 193 Triforine No treatment | i 2 50 0 500 500 500 500 500 500 500 500 500 500 500 500 500 500 500 500 500 500 500 500 500 - 500 500 500 500 500 500 500 500 500 500 500 500 500 500 500 50 0 500 500 500 | 500 - continued table 7 and ¦ « 1 0.0 « 7 0.0 1 22 0.0 4.8 0.0 0.0 8.0 0.0 6.4 0.0 7.4 0.0 0.0 5.2 3.4 3.2 10, 0 1 4.5 10.0 0.0 0.0 0.0 »,8 0.0 1.3 3.7 1 0.0 0.0 0.0 0.0 2.6 3.2 «,o 4 ,0 0.0 9.8 0.0 4.7 0.0 8.5 100.0 | 10 15 20 25 35 The following criteria were adopted as the basis for observing the infection status and calculating the severity of the disease: Severity (disease index) (number of leaves) diseases" 8X (total number of leaves examined) where R^ is a lower alkyl group, a lower cycloalkyl group with 3-5 carbon atoms, a lower alkenyl group, a lower haloalkyl group, a lower alkoxy group, a cycloalkoxy group with 3-5 carbon atoms, a lower alkynyl group, a lower haloalkoxy, lower alkenyloxy, lower alkynyloxy, lower alkylthio, alkoxylalkyl with 1-2 carbon atoms in the alkoxy radical and 1-2 carbon atoms in the alkyl radical, alkylthioalkyl group with 1-2 carbon atoms in the alkylthio radical and 1-2 carbon atoms in the alkoxy radical, a lower halogenalkynyloxy group or an alkoxyalkoxy group with 1-2 carbon atoms in the alkoxy radicals, R2 is a hydrogen atom, R3 is identical or different substituents, such as a hydrogen atom, a halogen atom, a group an alkyl group with 1-4 carbon atoms, an alkoxy group with 1-3 carbon atoms, a haloalkyl group with 1-3 carbon atoms, or an alkylthio group with 1-3 carbon atoms, n is an integer from 1 to 3, wherein when Rj is a fluorine atom, then n is an integer from 1 to 5, Y is an oxygen or sulfur atom, m is a zero and Z is an oxygen atom. 2. A herbicide and fungicide according to claim 1. 1, characterized in that it contains 1-80V of the active substance by weight. 3. A herbicide containing an inert carrier and an active substance, characterized in that the active substance is a compound of formula 1, wherein Rx is a lower alkyl group, a cycloalkyl group with 3-5 carbon atoms, a lower alkenyl group, a lower haloalkyl group, a lower cyanoalkyl group, lower alkoxy group, cycloalkoxy group with 3-5 carbon atoms, lower alkynyl group, lower haloalkoxy group;, lower alkenyloxy group, lower alkyloxy group, lower alkyl thio group, lower alkenylthio group, lower alkynes - lotio, alkoxyalkyl group with 1-2 carbon atoms in the alkoxy radical and 1-2 carbon atoms in the alkyl radical, alkylthioalkyl group with 1-2 carbon atoms in the alkylthio radical and 1-2 carbon atoms in the alkyl radical, lower halogenalkynyloxy group , an alkoxyalkoxy group having 1 to 2 carbon atoms in the alkoxy radicals or a 2-furfuryloxy group, R 3 represents a hydrogen atom or an alkyl group having 1 to 2 carbon atoms, R 3 represents identical or different substituents, such as a hydrogen atom , halogen atom, alkyl group with 1-4 carbon atoms, alkoxy group with 1-3 carbon atoms, haloalkyl group with 1-3 carbon atoms or alkylthio group with 1-1 carbon atoms, n is an integer) from 1 to 3| , wherein when R3 is a fluorine atom, then n is an integer from 1 to 5, Y is an oxygen or sulfur atom, m is an integer from zero to 1, and Z is an oxygen atom, a sulfur atom, straight or branched an alkylene group of 1 to 6 carbon atoms or a straight or branched alkylene group of 1 to 5 carbon atoms containing not less than one oxygen and/or sulfur atom at the end and/or center of the carbon chain, except where B^ is lower falkyl group, lower cycloalkyl group with 3-5 carbon atoms, lower alkenyl group, lower haloalkyl group, lower alkoxy group, cycloalkoxy group with 3-5 carbon atoms, lower alkynyl group, lower haloalkoxy- lower, lower alkenyloxy group, lower alkynyloxy group, lower alkylthio group, alkoxyalkyl group with 1-2 carbon atoms in the alkoxy radical and II-2 carbon atoms in the alkyl radical, alkylthioalkyl group with 1-2 carbon atoms in the alkylthio radical and 1 -2 carbon atoms in the alkyl radical, a lower haloalkynyloxy group or an alkoxyalkoxy group with 1-2 carbon atoms in the alkoxy radicals, R2 and 34 ao denotes a hydrogen atom, R3 denotes identical or different substituents, such as a hydrogen atom, a halogen atom, an alkyl group with 1-4 carbon atoms, an alkoxy group with 1-3 carbon atoms, a haloalkyl group with 1-3 carbon atoms, or an alkylthio group with 1-3 carbon atoms, n is an integer from 1'- 3u, wherein when R3 is a fluorine atom, then n is an integer from 1 to 5, Y is an oxygen or sulfur atom, m is zero and Z is an oxygen atom. 4. A herbicide and fungicide according to claim. 3, characterized in that it contains 1-80% by weight of the active substance.MMCOC=CH2 Formula 7 npattern 6 Pattern3 ^NHCO-OK CL Pattern9 CH; Hi*4 ^-NHCO-OH I * C\. Formula 10 .. ^*WL nzor iu locHrO ^v^ TT* mór5 *. W ^NHC0C2H5 Formula 11116 723 m ZE CM O o O ZE f x° u o V ZE o 1 o o X116 723116 723116 723 X O 11! O o (_ X 2 9: 4, X o o o X <\l (fi X X o o V o 1 o o X O O O : O CsJ X o C\J X o £ 3 5: X o x° o 9. X o 8 X o 1 X O . 1 X o o o X CM X ^ X U o , ^116 723116 723 i116 723 .TO 3 8 O X o X* o x" o I X 116 723 I*5 O 8 CJ 4, X X NHCHO CH-tQ)J-CH Cl^C7 XCCl3 Formula 216 PL PL PL

Claims (4)

1. Patent claims 1. A herbicide and fungicide containing an inert carrier and an active substance, except that as substances it contains a compound of formula 1, in which R^ is a lower alkyl group, a lower cycloalkyl group with 3-5 and 65 carbon atoms, lower alkenyl group, lower haloalkyl group, lower alkoxy group, cycloalkoxy group with 3-5 carbon atoms, lower alkynyl group, lower haloalkoxy group, lower alkenyloxy group, lower alkynyloxy group, lower alkylthio group, alkoxylalkyl group with 1-2 carbon atoms in the alkoxy radical and 1-2 carbon atoms in the alkyl radical, alkylthioalkyl group with 1-2 carbon atoms in the alkylthio radical and 1-2 carbon atoms in the alkyl radical, lower group haloalkynyloxy or an alkoxyalkoxy group with 1-2 carbon atoms in the alkoxy radicals, R2 means a hydrogen atom, R3 means identical or different substituents, such as a hydrogen atom, a halogen atom, an alkyl group with 1-4 carbon atoms, an alkoxy group with 1 —3 carbon atoms, a haloalkyl group having 1 to 3 carbon atoms, or an alkylthio group having 1 to 3 carbon atoms, n denotes an integer from 1 to 3, wherein when Rj denotes a fluorine atom, then n denotes an integer from 1 to 5, Y is an oxygen or sulfur atom, m is the number zero and Z is an oxygen atom. 2. A herbicide and fungicide according to claim 1. 1, characterized in that it contains 1-80V of the active substance by weight. 3. A herbicide containing an inert carrier and an active substance, characterized in that the active substance is a compound of formula 1, wherein Rx is a lower alkyl group, a cycloalkyl group with 3-5 carbon atoms, a lower alkenyl group, a lower haloalkyl group, a lower cyanoalkyl group, lower alkoxy group, cycloalkoxy group with 3-5 carbon atoms, lower alkynyl group, lower haloalkoxy group;, lower alkenyloxy group, lower alkyloxy group, lower alkyl thio group, lower alkenylthio group, lower alkynes - lotio, alkoxyalkyl group with 1-2 carbon atoms in the alkoxy radical and 1-2 carbon atoms in the alkyl radical, alkylthioalkyl group with 1-2 carbon atoms in the alkylthio radical and 1-2 carbon atoms in the alkyl radical, lower halogenalkynyloxy group , an alkoxyalkoxy group having 1 to 2 carbon atoms in the alkoxy radicals or a 2-furfuryloxy group, R 3 represents a hydrogen atom or an alkyl group having 1 to 2 carbon atoms, R 3 represents identical or different substituents, such as a hydrogen atom , halogen atom, alkyl group with 1-4 carbon atoms, alkoxy group with 1-3 carbon atoms, haloalkyl group with 1-3 carbon atoms or alkylthio group with 1-1 carbon atoms, n is an integer) from 1 to 3| , wherein when R3 is a fluorine atom, then n is an integer from 1 to 5, Y is an oxygen or sulfur atom, m is an integer from zero to 1, and Z is an oxygen atom, a sulfur atom, straight or branched an alkylene group of 1 to 6 carbon atoms or a straight or branched alkylene group of 1 to 5 carbon atoms containing not less than one oxygen and/or sulfur atom at the end and/or center of the carbon chain, except where B^ is lower falkyl group, lower cycloalkyl group with 3-5 carbon atoms, lower alkenyl group, lower haloalkyl group, lower alkoxy group, cycloalkoxy group with 3-5 carbon atoms, lower alkynyl group, lower haloalkoxy- lower, lower alkenyloxy group, lower alkynyloxy group, lower alkylthio group, alkoxyalkyl group with 1-2 carbon atoms in the alkoxy radical and II-2 carbon atoms in the alkyl radical, alkylthioalkyl group with 1-2 carbon atoms in the alkylthio radical and 1 -2 carbon atoms in the alkyl radical, a lower haloalkynyloxy group or an alkoxyalkoxy group with 1-2 carbon atoms in the alkoxy radicals, R2 and 34 ao denotes a hydrogen atom, R3 denotes identical or different substituents, such as a hydrogen atom, a halogen atom, an alkyl group with 1-4 carbon atoms, an alkoxy group with 1-3 carbon atoms, a haloalkyl group with 1-3 carbon atoms, or an alkylthio group with 1-3 carbon atoms, n is an integer from 1'- 3u, wherein when R3 is a fluorine atom, then n is an integer from 1 to 5, Y is an oxygen or sulfur atom, m is zero and Z is an oxygen atom. 4. A herbicide and fungicide according to claim. 3, characterized in that it contains 1-80% by weight of the active substance. MMCOC=CH2 Formula 7 W ^NHCOC^Hj 0CH,-O mor 2 ^^ X=^NHC0C2H5 /O. npattern 6 Pattern3 ^NHCO-OK CL Pattern9 CH; Hi*4 ^-NHCO-OH I * C\. Formula 10 .. ^*WL nzor iu locHrO ^v^ TT* mór5 *. W ^NHC0C2H5 Formula 11116 723 m ZE CM O o O ZE f x° u o V ZE o 1 o o X116 723116 723116 723 X O 11! O o (_ X 2 9: 4, X o o o X <\l (fi X X o o V o 1 o o X O O O : O CsJ X o C\J X o £ 3 5: X o x° o 9. X o 8 X o 1 X O u. 1 X o o o X CM X ^ X U o , ^116 723116 723 i116 723 .TO 3 8 O X o X* o x" o I X £116 723 I*5 O 8 CJ 4, X X X o I116 723 Cl ^'* ckVn-c-o-ch, Formula 213 DyN-c-NCCH3 W iQ /NHCHO CH-tQ)J-CH Cl^C7 XCCl3 Formula 216 PL PL PL