HU191006B - Herbicidal and plant growth regulating compositions comprising n-(phenyl-sulfonyl)-n'-triazinyl- or pyrimidinyl-urea-derivative as active substance and process for preparing the active substance - Google Patents

Abstract

N-Phenylsulfonyl-N'-pyrimidinyl- and -triazinyl ureas of the general formula <IMAGE> and the salts of these compounds with amines, with alkali metal bases or alkaline earth metal bases or with quaternary ammonium bases, possess good selective, pre-emergent and post-emergent, herbicidal properties. In this formula A denotes a C1-C6-alkyl radical which is substituted by halogen, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylsulfinyl, C1-C4 -alkylsulfonyl, C1-C4-haloalkoxy, C1-C4-haloalkylthio, C1-C4-haloalkylsulfinyl or C1-C4-haloalkylsulfonyl, or denotes a C2-C6-alkenyl radical which is optionally substituted by the enumerated substituents, E denotes the methine group or nitrogen, X denotes oxygen, sulphur, or a sulfinyl or sulfonyl bridge, Z denotes oxygen or sulphur, m denotes the number one or two, R1 denotes hydrogen, halogen, C1-C5-alkyl, C2-C5-alkenyl, or a radical -Y-R5, R2 denotes hydrogen, halogen, C1-C5-alkyl, C2-C5-alkenyl, C1-C4-haloalkyl, or a radical -Y-R5, -COOR6, -NO2 or -CO-NR7R8, R3 and R4, independently of each other, denote hydrogen, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4- haloalkyl, halogen or alkoxyalkyl having at most 4 carbon atoms, R5 and R6 in each case denote C1-C5-alkyl, C2-C5-alkenyl or C2-C6-alkynyl R7 and R8, independently of each other, denote hydrogen, C1-C5-alkyl, C2-C5-alkenyl or C2-C6-alkynyl, and Y denotes oxygen, sulphur, or a sulfinyl or sulfonyl bridge.

Description

FIELD OF THE INVENTION The present invention relates to herbicidal and plant growth regulating agents containing novel N-phenylsulfonyl-N-plimidinyl and triazinylcarbamides as active ingredients and to a process for their preparation.

The agents of the invention are particularly useful for controlling weeds, in particular for their selective control in crop plants, and for controlling plant growth and inhibiting growth.

The novel N- (phenylsulfonyl) -N'-pyrimidinyl and triazine ureas correspond to formula (I). In this formula

A is C 1-5 alkyl substituted with 1 to 5 halo or C 1 -C 4 alkoxy, C 1 -C 4 alkyl, C 1 -C 4 alkylsulfinyl or C 1 -C 4 alkylsulfonyl groups. or C 1 -C 6 alkenyl optionally substituted with 1 or 2 halogens,

-E represents a methylene group or a nitrogen atom,

X is oxygen, sulfur, sulfinyl or sulfonyl,

-Z is oxygen or sulfur,

-the value is 1 or 2,

R 1 is hydrogen, halogen, C 1 -C 5 alkyl or C 14 alkoxy,

-R j is hydrogen or halogen,

R3 and _R4 are independently C1-4 alkyl, C1-4 alkoxy, C1-4 alkylthio group, C1-4 haloalkyl or halogen, with the proviso that m is 2 when X is sulfur, sulfinyl or each sulfonylhyde and A, meanwhile, represent a C 34 alkenyl group.

The agents of the invention may also contain salts of said compounds as active ingredients. The invention also relates to a process for the preparation of salts.

Herbicidal urea compounds, triazine compounds and pyrimidine compounds are generally known. For example, herbicides and arylsulfamoyl-heterocyclylaminocarbamoyl compounds having herbicidal activity have recently been disclosed in European Patent Nos. 1514 and 1515, 4,127,405. U.S. Patent Nos. 2,715,786; and French Patent Nos. 1,468,747.

Alkyl as used herein means straight or branched chain alkyl groups such as methyl, ethyl, η-propyl, isopropyl, the four isomers butyl, n-amo, isoamyl, 2-amu or 3 amflcsoport.

Alkoxy means methoxy, ethoxy, n-propoxy, isopropyloxy and the four isomeric butyloxy groups, in particular methoxy, ethoxy or isopropyloxy.

Examples of alkylthio include methylthio, ethylthio, η-propylthio, isopropylthio and n-butylthio, in particular methylthio and ethylthio. pose.

Examples of alkenyl include vinyl, allyl, isopropenyl, 1-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-isobutenyl, 2-isobutenyl. Ι-Pentenyl, 2-pentenyl, 3-pentynyl, and 4-pentenyl, in particular vinyl, allyl and 4-pentenyl, may be mentioned.

False alkylsulfinyl groups include, for example, methylsulfonyl, ethylsulfinyl, n-propylsulfonyl and n-butylsulfonyl, but especially methylsulfinyl or ethylsulfinyl.

Examples of alkylsulfonyl include methyl-azulfonyl, ethyl-sulfonyl, η-propylsulfonyl, and n-butylsulfonyl, in particular methylsulfonyl and ethylsulfonyl.

The term halogen as used in A, R 1 -R 4 and haloalkyl means fluorine, chlorine and bromine, preferably fluorine and chlorine.

The compounds of formula (I) may also be used in the compounds of the invention in the form of basic addition salts, preferably salts thereof with amines and alkali metals.

As the salt-forming alkali metal hydroxide, lithium, sodium and potassium hydroxides, in particular sodium or potassium hydroxide, may be used.

Suitable amines for the formation of salts are primary, secondary and tertiary aliphatic and aromatic amines such as methylamine, ethylamine, propylamine, isopropylamine, the four isomers butylamine, dimethylamine, diethylamine, diethanol. amine, dipropylamine, diisopropylamine, di-n-butylamine, pyrrolidine, piperidine, morpholine, trimethylamine, tripropylamine, quinuclidine, pyridine, quinoline and isoquinoline, especially ethyl, propyl, diethyl or triethylamine, in particular isopropylamine and diethanolamine.

The compounds of the formula I can be divided into two major subgroups. These groups consist of compounds of formula I wherein A is

1) C 1 -C 5 alkyl substituted with C 14 alkoxy, C 14 alkyltlo, C 14 alkylsulfonyl or C 14 alkylsulfonyl, or C 2 -C 6 alkenyl optionally substituted with 1 or 2 halogens;

2) C 1-5 haloalkyl.

Within Group 1), those compounds in which

(a) Z is oxygen; and

b) R3 and R4 together do not contain more than 4 carbon atoms.

Subgroup 1a) can be divided into two further subgroups consisting of compounds wherein aa) m is 1 and b) m is 2.

Preferred compounds of the group laa) are those in which the -X-A group is in the 2 or 3 position relative to the sulfonyl group. Of these, compounds in which the -X-A group is in the 2-position are even more preferred.

Preferred compounds of the foot group are those in which the two -X-A groups are in the 2-position and the 5-position of the sulfonyl group.

Further preferred representations of the sub-groups laa and ft) listed above, when the substituents R ₃ and R 4 together contain up to 4 carbon atoms. A particularly preferred group of compounds are those groups having the formula (a) (aafc) only one -XA group at the 2-position relative to the sulfonyl group, Z represents an oxygen atom, and R ₃ and R <together contain up to 4 carbon atoms, and ) there are two -XA groups at the 2 and 5 positions relative to the sulfonyl group, Z is oxygen and R3 and R4 together are up to 4 carbon atoms.

Preferred compounds of the group aab) are those wherein R 1 is hydrogen and the substituent R ₂ is in the 5 or 6 position relative to the sulfonyl group. _>

Among these compounds, those particularly preferred are those wherein R _{2 is} hydrogen or halogen.

Further preferred compounds within the latter group are those wherein R _{2 is} hydrogen or fluoro, R ₃ and R 4 are C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, desire halogen and R ₃ and R, taken together, is up to 4 carbon atoms.

Also preferred among these compounds are those wherein R 1 is hydrogen, R ₃ and R ₃ are C 14 alkyl, C 14 alkoxy, methylthio, or halogen.

Within the latter group, compounds in which X is O or S are particularly preferred.

Particularly preferred compounds are those wherein A is C2-C8 alkoxyalkyl, C2-C4 haloalkenyl or C2-C6 alkenyl.

Of the latter group, three further subgroups of compounds are preferably used in them

a) A is C 2 -C 8 alkoxyalkyl,

R ₃ and R ₄ are methyl, ethyl, chloro or methoxy,

β) A is C 2 -C 6 alkenyl and R ₃ and R ₄ are methyl, ethyl, chlorine or methoxy; and

γ) A is vinyl substituted with 1 or 2 halogen atoms, and R ₃ and R ₄ are methyl, ethyl, chloro or methoxy.

Among the compounds of formula I wherein Z is sulfur, they are preferably those wherein X is oxygen or sulfur, R ₃ and R ₄ are each independently C 1-3 alkyl, C 1-3 alkoxy or C 1-3 alkyl. thio and said groups together contain up to 4 carbon atoms, A is -CH ₂ -CH * CH ₂ , -CH ₂ -CH = CH-CH ₃ , -CH ₂ -CH (CH ₃ > CH ₃ , methoxyethyl) , methoxymethyl or -CC1 = CHCl, and -XA occupy position 2 while m is 1.

Preferred individual compounds which may be used are N- [2- (allyloxy) phenylsulfonyl] -N- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) urea.

Within Group 2), compounds in which ______

a) a -X-A group is in the 2 or 3 position of the benzo ring; ·

b) only one -X-A group is present and occupies the 2-position of the benzene ring.

c) R 1 and R _{2 are} hydrogen; and

d) R ₃ and R ₄ independently of one another contain up to 2 carbon atoms.

Of group 2), compounds having only one substituent -XA and occupying the 2-position of the benzene ring, in which R ₃ and R 4 independently are not more than 2 carbon atoms and R ₁ and R ₂ are each hydrogen, are particularly preferred.

Particularly preferred among the latter compounds are those wherein R ₃ and R ₄ independently of one another are methyl or methoxy.

Such group includes those compounds of formula (I) wherein R, and R ₂ is hydrogen, X and Z are oxygen, E is nitrogen, R ₃ methoxy, R ₄ is methyl or methoxy and A is a difluoromethyl group and the difluoromethyl and the group -XA occupies the 2-position on the benzene ring and may also represent X as a sulfur atom when R _{3 is} methyl.

Such unique compounds are: ₍

N- [2- (difluoro-methoxy) phenyl] -N '- (4,6-dimethoxy-1,3,5-triazin-2-yl) -urea,

N- [2- (difluoromethoxy) phenylsulfonyl] -N '- (4-methyl-6-methoxy-1,3,5-triazin-2-yl) urea,

N- [2- (Difluoromethylthio) phenylsulfonyl] -N- (4-methyl-6-methoxy-1,3,5-triazin-2-yl) urea, _t

N- [2- (1,1,2,2-tetrafluoroethoxy) phenylsulfonyl] -N- (4-methyl-6-methoxy-1,3,5-triazin-2-yl) carbarpide,

N- [2- (trifluoromethoxy) phenyl] sulfonyl] -N- (4-methyl-6-methoxy-1,3,5-triazin-2-yl) urea,

N- [2- (trifluoromethoxy) phenylsulfonyl] -b | '- (4-methyl-6-methoxy-pyrimidin-2-yl) -urea,

N- [6-chloro-2- (difluoromethoxy) phenylsulfonyl) -N- (4-methyl-6-methoxy-1,3,5-triazin-2-yl) urea and,

N- [2- (difluoromethoxy) -5-fluorophenylsulfonyl] -N- (4-methyl-6-methoxy-1,3,5-triazin-2-yl) urea.

A further subgroup of group 2 are those compounds of formula I wherein A is C 1 -C 5 haloalkyl, with the proviso that m is 2 when A is -CHF ₂ , -CH ₃ at the same time. -CH ₂ -CF ₃ , -CF ₂ -CHF ₂ -, -CF 3 -CHFCl, -CF ₂ -CHFBr or -DV ₂ -CHF-CF ₃ ,

R ₃ is OCH ₃ or -CH ₃ ,

R 1 is -OCH ₃ , H H ₃ or -OC ₂ H _S and the benzene ring is not substituted or is substituted at the 2, 3, 5 or 6 position with ew only with respect to the sulfonyl group a fluorochlorine or bromine atom or a methyl group.

Preferred compounds of this subgroup 2.1 are those in which

(a) Z is oxygen; and

b) R ₃ and K group containing up to four carbon atoms together.

Sub-group 2.1a) can be divided into two further subgroups, in which aa) m is 1 and b) m is 2.

Preferred compounds from group 2.1aa) are those in which the -X-A group is in the 2 or 3 position relative to the sulfonyl group. Of these, compounds in which the -X-A group is in the 2-position are further preferred.

From group 2) compounds are preferred groups in which the two -X-A groups occupy positions 2 and 5 relative to the sulfonyl group.

Preferably from the ^main listed ent 2.1a) and 2.láb) subgroups food compound are those which contain up to 4 carbon atoms, R ₃ and R ₄ together. A particularly preferred group of compounds of formula I are those wherein aab) has only one -XA group at the 2-position for the sulfonyl group, and R ₃ and R 4 together have up to 4 carbon atoms and abb) two -XA groups. group is selected from relative to the sulfone 2- and 5-position, R ₃ and R 4 together are no more than 4 carbon atoms is enforced.

Further preferred compounds of sub-group 2.1 aab) are those wherein A is -CHF ₂ , -CF ₃ or -CH ₂ -CH ₂ Cl.

Of subgroup 2.1 aab), compounds wherein R _{t is} hydrogen and R _{2 is in the} 5- or 6-position relative to the sulfonyl are preferably used.

In particular, those compounds in which R _{2 is} hydrogen or fluorine are particularly useful.

Within the latter group, compounds wherein X is oxygen are sulfur.

Among them it is particularly useful for those compounds wherein R _and R ₂ substituents are both hydrogen, R ₃ is chloro or fluoro, methyl, chloromethyl, alkoxy, οχί- isopropyl, ethyl or methoxy and R4 is methyl, ethyl, methoxy or ethoxy.

Two further preferred subgroups of the latter group are those in which (a) X is a oxygen atom and

β) A is -CF ₂ G wherein G is hydrogen, fluoro, chloro or bromo, trifluoromethyl, or methyl.

Within group (p), compounds in which G is chlorine or bromine or trifluoromethyl should be highlighted.

Compounds in which A is -CH ₂ F-, -CH ₂ -CH ₂ Cl, or -CH ₂ -CH ₂ F occupy a preferred position similar to groups a) and β).

Among the compounds of formula I wherein Z is sulfur, they are preferably used wherein X is oxygen or sulfur and R ₃ and R 4 are each independently C 14 alkyl, C 14 alkoxy or C 14 alkylthio and together containing up to 4 carbon atoms. A is CHF _2, CF _3, C ₂ F • _s or -CF ₂ -CHF ₂ group and the group -X is in the 2-position.

Preferred compounds are the following derivatives at ru »water» 77nlr τηριτ ·

N- (2- (difluoromethoxy) phenylsulfonyl] -N '- (4-methyl-6-methoxy-1,3,5-triazin-2-yl) -urea,

N- [2- (difluoromethoxy) phenylsulfonyl] -N- (4,6-diethoxy-1,3,5-triazin-2-yl) carbamyl,

N- [2- (difluoromethoxy) phenylsulfonyl-N- (4-chloro-6-methylpyrimidin-2-yl) urea,

N- [2- (pentafluoroethoxy) phenylsulfonyl) -N '- (4-methoxy-6-methyl-1- ₍ 3,5-triazin-2-yl) carbamate,

N- [2- (difluoromethyl) thio -fenlI-sulfonyl] -N '(4-chloro-6-nsetoxl-pyrimidin-2-yl) -karbaniid,

N- [2,5-bis (difluoromethoxy) phenylsulfonyl] -N '- (4-netoxy-6-methyl-1,3,5-triazin-2-yl) urea,

N- [2- (di-fluoromethoxy) phenylsulfonyl] -N- (4-methoxy-6-isopropyloxy-1,3,5-triazin-2-yl) urea, ₍

N- [2- (difluoromethyl-ylthio) phenyl] sulfonyl] -N ^- {4-ethyl-6-methoxy-l, 3,5-triazin-2-yl) urea and

N- [2- (difluoromethoxy) phenyl-sulfonylamino] -N- (4-chloro-6-methoxy-pyrimidin-2-yl) urea.

The compounds of formula (I) are prepared in an inert organic solvent.

In a first embodiment, the compounds of Formula I are prepared by reacting a phenylsulfonamide of Formula II wherein A, R 1, R ₂ , X and m are as defined above, in the presence of a base of Formula III. With N-pyrimidinyl or -triazinylcarbamate wherein E, R ₃ , R ₄ and Z are as defined above.

In a second embodiment, the compounds of formula (I) are obtained by reacting a phenylsulfonyl isoclanate or isothiocyanate of formula (IV) wherein A, R 1, R ₂ , m, X and Z are as defined above, optionally in the presence of a base. , With an amine of formula (V) wherein E, R ₃ and R ₄ are as defined above.

In another embodiment, the compounds of formula (I) are prepared by reacting a sulfonamide derivative of formula (I), optionally with an isocyanate of formula (VI) in the presence of a base, wherein E, R 1; R ₄ and Z are as defined above.

Finally, may be prepared by (I) Compounds of formula (VII) with N-phenylsulfonyl-Carbamates of general formula wherein A, _{R}, R2,} m and X are same as defined above, (V) with an amine of formula is reacted with .

The resulting compounds of formula (I) may, if desired, be converted into basic addition salts with amines or alkali metal hydroxides. For example, the conversion is carried out by reacting the compound with an equimolar amount of base and evaporating the solvent.

The starting materials of the formulas (II), (IV) and (VE) are partially novel and can be prepared by the following methods:

The sulfoamide derivatives of formula (I) used as new and intermediates are diazotized from the corresponding anilines and the diazo group is replaced with sulfur dioxide in the presence of a catalyst such as copper (I) chloride in hydrochloric acid or acetic acid and hydroxylated with phenylsulfonyl chloride. we produce it.

The compounds of formula (II) may also be prepared by subjecting the hydroxy or thiophenylsulfonamides to the corresponding halides or sulfuric acid esters by oxygen or sulfur alkylation or alkenylation, or by addition of ortho-halophenylsulfonamides with metal alcoholates and in this case they are oxidized with, for example, peodates or peracids to the corresponding sulfoxides and sulfones.

The ortho-substituted hydroxyphenyl or substituted ortho-hydroxyphenylsulphonanyl derivatives of the general formula (VIII) wherein R 1 -Ee.R 1 is as defined for the general formula (1) and X is an oxygen or sulfur atom. The starting materials for the sulfonamide compounds of formula (II) are novel compounds other than orthohydroxy-phenylsulfonamide. These compounds can be prepared by etherification of the corresponding C 1 -C 4 alkoxyphenylsulfonamides, such as boron trihalide (Such reactions are described in U.S. Pat. No. 3,904,680 and J. Am. Chem. Soc. 64, 1128 (1942)). ) Or by hydrogenolysis of the corresponding benzyloxyphenylsulfonamides as described in J. Chem. Soc. 1958, 2903.

The alkoxyphenylsulfonamides can be obtained from the corresponding alkoxyl anilides as described above or by the chlorosulfonation of the alkoxybenzenes and the reaction of the resulting phenylsulfonyl chlorides with ammonium hydroxide solution. Such reactions are known from J. Am. Chem. Soc. 62, 603 (1940).

The intermediates (H) and (VIII) used as intermediates are novel or partially novel and have been developed for the synthesis of compounds of formula (I).

The phenylsulfonyl isocyanates of formula (IV) may be prepared by reacting the sulfonamides of formula (H) with phosgene in the presence of butyl isocyanate in a chlorinated hydrocarbon solvent while heating to reflux. Similar methods of preparation are described in Newer Methods of Prep. 223-241. (Academic Press New York, and London).

Isothiocyanates of formula (IV) may be prepared by treating the parent amide of formula (II) with carbon disulfide and potassium hydroxide and subsequently reacting the resulting dipotassium salt with phosgene. Such procedures are described in Arch. Pharm. 299, (1966).

The N-phenylsulfonylcarbamates of Formula VII can be prepared by reacting the sulfonamides of Formula II with diphenylcarbamate in the presence of a base. Similar procedures are described in Japanese Patent Application No. 61,169.

The starting materials of formulas (III), (V) and (VT) are known or can be prepared by known methods.

Reaction of amines of formula (V) with oxalyl chloride in chlorinated hydrocarbon solvents leads to isocyanates of formula (VI). The amines of formula (V) are known and are partly commercially available or may be prepared by known methods. Such methods of preparation are described in "The Chemistry of Heterocyclic Compounds", XIV. (Interscience Publishers, New York, London).

Conversion to compounds of formula (I) is preferably carried out in proton-free, inert organic solvents such as methylene chloride, tetrahydrofuran, acetonitrile, dioxane or toluene. ₀

The reaction temperature is preferably -10 ° C to + 120 ° C. The reactions are generally slightly exothermic and can be performed at room temperature. In order to shorten the reaction time or to initiate the reaction, it is preferable to heat the reaction mixture to reflux temperature for a short time. The reaction times can also be shortened by adding a few drops of base or isocyanate as the reaction catalyst.

The final products may be isolated by evaporation and / or evaporation of the solvent and the solid residue may be purified by recrystallization or trituration from solvents in which the product is poorly soluble. Such solvents include ethers, aromatic hydrocarbons and chlorinated hydrocarbons.

The active compounds of formula (I) are stable compounds and do not require any particular treatment.

Agents containing compounds of formula (I) have potent growth regulating properties, in particular growth inhibitory properties, and affect the growth of both monocotyledonous and dicotyledonous plants.

Thus, for example, the growth of leguminous plants, often planted as cover crops in agriculture, can be selectively inhibited by their use, thereby preventing soil erosion between crop plants.

Agents containing the active compounds of formula (I) are also suitable for preventing the germination of the harvested potato. In winter storage, potatoes often germinate and these germs cause shrinkage, decay and weight loss of the potato.

Our experiments show that the use of higher amounts causes all plants to be damaged or destroyed.

The agents according to the invention exhibit good selective growth inhibitory and selective herbicidal activity at lower application rates, which make them very useful in crop weed control, particularly useful in cereals, cotton, soy, maize, and rice weeds. The treatment with the agents according to the invention also partially damages weeds that have been hitherto restricted to so-called weeds. it could be eradicated with totiflblcids.

The agents of the present invention have an unusual mode of action. Many of these can be translocated, that is, taken up by the plants and transported to another site of the plant where they act. Unusual means is that the active ingredients are transported not only through the bundle of vessels in the wood, i.e. from the roots to the leaves, but also through the fibrous tubes in the bark, from the leaves back to the roots. In this way, it is possible, e.g. to damage perennial weeds to the roots by treating the upper part of them. The agents according to the invention containing the compounds of the formula I are effective even at very low amounts compared to other herbicides and plant growth regulators.

The herbicidal and plant growth regulating agents containing the compounds of formula (I) as active ingredients can be used to control weeds before and after emergence and to inhibit the growth of monocotyledonous and dicotyledonous plants, in particular grasses, hot soil coverings and tobacco shoots.

Agents containing the active compounds of formula (I) contain excipients conventionally used in pesticide formulations and may be prepared in the usual manner and form. Examples include emulsifiable concentrates, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusting agents, granules, capsules, for example encapsulated in polymeric materials, and the like. The application method, such as spraying, fogging, dusting, spraying or casting, is selected according to the type of agent and the intended purpose to be used.

Morality, i.e. the preparation of a composition or composition comprising the active ingredient of formula (I) and a solid or liquid additive, is carried out in conventional manner, for example, by mixing the active ingredients with fillers such as solvents, solid carriers and optionally surfactants (surfactants). / or grind.

Suitable solvents are: aromatic hydrocarbons, preferably C8-C12 fractions, for example xylene mixtures or substituted naphthalenes, phthalic esters such as dibutyl or dioctyl phthalates, aliphatic hydrocarbons such as cyclohexane or paraffins, alcohols and glycols, other ethers and esters such as ethanol, ethylene glycol, ethylene glycol monomethyl or ethyl ether, ketones such as cyclohexanone, highly polar solvents such as N-methyl-2-pyrrolidone, dimethyl sulfoxide or dimethylformamide; optionally epoxidized vegetable oils, such as epoxidized coconut oil or soybean oil or water.

Solid carriers, for example, for dusting and dispersible powders, are usually natural rock flour, khaki, talc, kaolin, montmorrillonite or attapulgite. Highly dispersed silica or a highly dispersed absorbent polymer may also be used to improve physical properties. Porous granular materials, such as pumice, brick, sepiolite or bentonite, as well as non-sorbent carriers, such as calcite or sand, may be used as particulate adsorptive granule carriers. In addition, many pre-granulated materials of inorganic or organic nature, in particular dolomite or shredded plant waste, can be used for this purpose.

Depending on the active ingredient of the formula (1) to be formulated, the surfactants are non-ionic, cationic and / or anionic surfactants with good dispersing, emulsifying and wetting properties. Tensides also include surfactant mixtures.

Suitable anionic surfactants include so-called water-soluble soaps and water-soluble synthetic surfactants.

Suitable soaps include the alkali metal and optionally substituted ammonium salts of higher carbon (10-22 carbon atoms) fatty acids, such as sodium or potassium salts of oleic or stearic acids, or natural fatty acid mixtures such as coconut oil or tallow oil. Mention may also be made of fatty acid methyl taurine salts.

More commonly, however, so-called synthetic surfactants are used, especially fatty alcohol sulfonates, fatty alcohol sulfates, sulfonated benzimidazole derivatives or alkylaryl sulfonates.

The fatty alcohol sulfonates or sulfates are usually used in the form of alkali metal, alkaline earth metal or optionally substituted ammonium salts having from 8 to 22 carbon atoms and the alkyl moiety also includes the alkyl moiety of the acyl moiety. These include the sodium or calcium salts of lignin sulfonic acid, dodecyl sulfuric ester, or fatty alcohol sulfate derived from natural fatty acids. Also included are the salts of the fatty acids of the sulfuric acid salts and fatty alcohol ethylene oxide adducts. The sulfonate-free benzimidazole derivatives preferably contain 2 sulfonic acid groups and a C 8 -C 22 fatty acid moiety. Alkylarylsulfonates include, for example, sodium, calcium, or triethanolamine salts of dodecylbenzenesulfonic acid, dibutylnaphthalenesulfonic acid or formaldehyde condensation product of naphthalenesulfonic acid.

The salts of the phosphoric acid ester of the corresponding phosphates, such as the p-nonylphenol (4-14) ethylene dioxide adduct, may also be used.

Suitable nonionic surfactants are, in particular, poly (glycol ether) derivatives of aliphatic or cycloaliphatic alcohols, saturated or unsaturated alcohols and alkyl phenols having from 3 to 30 glycol ether groups and from 8 to 20 carbon atoms in the They contain 18 carbon atoms in the alkyl portion of the alkyl phenol.

Other suitable nonionic surfactants are water-soluble polyethylene oxide adducts having 20-250 ethylene glycol ether groups and 10-100 propylene glycol ether groups, polypropylene glycol, ethylene diaminopropylene glycol. These compounds usually contain from 1 to 5 ethylene glycol units per piopylene glycol unit.

Examples of nonionic surfactants are nonyl phenol poly (ethoxyethanol), castor oil poly (glycol ether), polypropylene poly (ethylene oxide) adduct, tributyl phenoxy ethanol, polyethylene glycol. and octylphenoxy-poly (ethoxyethanol).

Fatty acid esters of polyoxyethylene sorbitan such as polyoxyethylene sorbitan trioleate may also be used.

The cationic surfactants are, in particular, quaternary ammonium salts which contain at least one C 8 -C 22 alkyl group as the N-substituent and further lower alkyl optionally halogenated alkyl, benzyl or lower hydroxyalkyl groups. The salts are preferably halides, methylsulfates or ethylsulfates, such as stearyltrimethylammonium chloride or benzyldi (2-chloroethyl) ethylammonium bromide.

The surfactants which can be used in the formulation are described, inter alia, in the following literature:

McCutcheon's Detergents and Emulsifiers Annual, MC Publishing Copr., Ringwood, New Jersey, 1979,

Slsely and Wood, Encyclopedia of Surface Active Agents, Chemical Publishing Co., Inc. New York, 1964.

The herbicidal compositions are usually 0.0195% by weight, in particular 0.1-80% by weight of the active compound of the formula I, 5 to 99.9% by weight of the solid or liquid.

They contain 191 006 kitchen scavengers and / or other additives, in particular tenzld.

The following compositions are particularly preferred: (% =% by weight)

Solutions active ingredient 1-30%, preferably 5-20%, solvent 90-0%, preferably 95-0%, surfactant 0-99%, preferably 0-95%,

Emulsifiable concentrates contain from 1% to 20%, preferably from 5% to 10%, surfactant from 5% to 30%, preferably from 10% to 20%, liquid carrier from 50% to 94%, preferably from 70% to 85%. Powders of active ingredient 0.1-10%, preferably 0.1-1%, solid carrier 99.9-90%, preferably 99.9%

-99%.

Suspension concentrates contain from 5% to 75%, preferably from 10% to 50%, water from 94% to 25%, preferably from 90% to 30% surfactant, from 1% to 40%, preferably from 2% to 30%.

Wettable powders contain 0.5-90% active ingredient, preferably 1-80%, surfactant 0.5-20%, preferably 1-15% solid carrier 5-95%, preferably 15-90%.

Granules active ingredient 0.5-30%, preferably 3-15% solid carrier 99.5-70%, preferably 97-85%

Concentrated agents are preferred as commercially available products, while diluted agents are generally used by users. The formulations may be diluted to a concentration of 0.001% w / w. The application rates are usually 0.01 to 10 kg of active ingredient / ha, preferably 0.025 to 5 kg of active ingredient / ha.

The agents of the present invention contain additional additives, such as stabilizers, antifoams, viscosity regulators, binders, tackifiers, and fertilizers, or may be mixed with other active ingredients to achieve specific effects.

The invention is further illustrated by the following examples. In the examples, the temperature is given in degrees Celsius (° C) and the pressures in millibars (mb).

«

Production examples

Example 1

To a suspension of 2-hydroxyphenylsulfonamide 2 g of methyl 2-methoxyphenylsulfonamide in 210 ml of dry methylene chloride was added 22.2 ml of boron tribromide under nitrogen at room temperature for 15 minutes and the reaction mixture was stirred at room temperature for 1 hour. The mixture was cooled to 0 ° C and methanol (200 mL) was added over 15 minutes and the clear solution was evaporated. The oily residue was taken up in ethyl acetate, washed twice with water, dried over sodium sulfate and evaporated. The residue was triturated with petroleum ether to give 25.1 g of 2-hydroxyphenylsulfonamide, m.p. 136138 ° C.

In a similar manner, hydroxy-phenylsulfonamides of the general formula (VIIIa) listed below are prepared. In Table ₂ the substituents R, and R values of the position of the -OH group and the physical data of the product.

Example 3

a) 2- (Difluoromethoxy) phenylsulfonyl chloride

D

To a solution of 6.4 g of copper sulfate in 276 ml of a mixture of 36% acetic acid and 72 ml of vlx is added 10 µl of 2 g of 40% sodium bisulphite solution at a temperature below 0 ° C. To the resulting solution was added dropwise 101.2 g of sodium bisulfite solution and dlazonium salt solution cooled to -10 ° C, which was obtained by cooling 28.8 g of sodium nitrite in 44 nl of water. is added dropwise to a solution of 63.7 g of 2-difluoromethoxyaniline in 39 ml of water and 84 ml of 36% hydrochloric acid. Meanwhile, the reaction mixture is heated to 30 ° C with simultaneous gas evolution. After stirring for 18 hours, a brown oil was formed. After separation of the organic phase, the aqueous phase is extracted with methylene chloride. The organic layers were combined and evaporated to give crude 80.3 2- (difluoromethoxyphenylsulfonyl chloride) as a brown oil.

b) 2- (difluoromethoxy) phenylsulfonamide

To a mixture of 250 ml of methylene chloride, 250 ml of water and 250 ml of 30% ammonium hydroxide solution is added slowly 80.3 g of crude 2-difluoromethoxy-phenylsulfonyl chloride in 50 ml of methylene 30-chloride. . After completion of the exotherm, the reaction mixture was refluxed for 2 hours. The organic phase is then washed with water, dried over sodium sulfate, evaporated and the residue is recrystallized from methanol. This gives 40.5 g of 2- (difluoromethoxy) phenylsulfonamide, m.p. 128-130 ° C.

Example 4

a) 2-Pentafluoroethoxy) sulfonyl chloride

6.4 g sub-sulfate 276 ml of 36% hydrochloric acid under cooling with 72 ml of a solution of ^u water mixture below 0 ° C temperature, 101.2 g of 40% sodium hydrogen szulflt was added dropwise. To the resulting solution was added dropwise a solution of 40 g of sodium bisulfite solution 40% and diazonium salt solution cooled _to -10 ° C, which was obtained by cooling, while cooling, 28.8 g of sodium nitrite in 44 ml of water. To a solution of 8 g of 2- (pentafluoroethoxy) aniline in 39 ml of water and 84 ml of 36%. Meanwhile, the reaction mixture is heated to 30 ° C with simultaneous gas evolution. The reaction mixture was stirred for 18 hours to give a brown oil. After separation of the organic phase, the aqueous phase is extracted with methylene chloride. The organic layers were combined and evaporated to give the crude product

2- (pentafluoroethoxy) phenylsulfonyl chloride is obtained in the form of a brown oil.

b) 2- (pentafluoroethoxy) phenylsulfonamide

To a mixture of 250 ml of methylene chloride, 250 ml of water and 250 ml of 30% ammonium hydroxide solution, add θθ to the solution of 4a. The crude 2- (pentafluoroethoxy) phenylsulfonyl chloride obtained in Example 1d was dissolved in 50 ml of methylene-71 chlorine. After completion of the exotherm, the reaction mixture was refluxed for 2 hours. The organic layer was washed with water, dried over sodium sulfate, evaporated and the residue was recrystallized from methanol. 65.0 g of 2- (pentafluoroethoxy) phenylsulfonamide are thus obtained. 145-146 ° C.

In a similar manner, the following new intermediates for the synthesis of compounds of formula (1) are prepared, which are listed in the following table. The table indicates, for Rj, _R2, X, A and m are the values of the position of the -X group and the physical data. The compounds listed in Table 3 correspond to Formula II.

_______ Table I ____

R. R-, -OH- Physical Data Situation ____ ~ ___ Λ _

5-CH H 2 90-91 ° C ch ₃ 2-CH ₃ H 5 2-C1 H 5 5-F H 2 141-142 ° C 5-Br Η 2 169-170 ° C 5-NO ₂ H 2 180-185 ° C 3 <H ₃ H 2 Op.133134 C 2-CH Η 3 3-C1 Η 2 6-CH ₃ Η 2 3-OCH Η 2 2-OCH ₃ Η 2 3-CH 5Γ ₄ Η ₉ (1) 2 Mp 137-137 ° C 6 OCHq Η 2 6-OH Η 2 5-OCH ₃ Η 2 Ορ.119-120 C 2-OCH ₃ Η 5 Ορ. 213-215 ° C 5-CH Η 2 Ορ. 155-156 ° C 6-C1 Η 2 Ορ. 190-191 ° C 3-NO ₂ Η 2

3-COOCH ₃ H 2 5-COOCH, H 2 171-172 ° 5-C1 H 2 176-179 ° 5-NO ₂ -CF 3, 2 5-NO ₂ 3-C1 2 ^{5C ,?} 3 3- ⁿ⁰ 2 2 ^{5c ,,} 3 3CH ₃ 2 5-Cl 3 NO, 2 5 -Cl 3-C1 2 156-158 ° 5-Bi 3-OCH ₃ 2 5-Bi 2OCH ₃ 3 194-197 ° 3-OCH ₃ 5-COOCH ₃ 2 2-OCH ₃ 5C00CH, 3 5-CH ₃ 3-Br 2 5-Br 3-NO ₂ 2 5-Br 3-COOCH ₃ 2 5-COOCH ₃ 3-NO ₂ 2 5-0 3-B 2 M.p. 247-249 ° 3-NH ₂ H 2 5-NH, 5-COOC ₃ H ₇ H 3 -NO ₂ 2 2 (0 '5-CON / CH _3/2 H 2 6-NO ₂ 6-COOCH, H H 2 2

Example 2

2- (allyl-phenyl-szulfonainid)

A mixture of 3.5 g of 2-hydroxy-phenylsulfonanide, 5.5 g of potassium and 1.7 ml of allyl bromide in 100 ml of methyl ethyl ketone is stirred at reflux under nitrogen for 1 hour. The reaction mixture was cooled to room temperature, filtered and evaporated and then recrystallized once from ethyl acetate. 3.27 g of 2- (allyloxyphenylsulfonamide) are thus obtained, m.p.

Similarly, the compounds of formula (Ha) listed in the following table were prepared. In Table Rj, _R2, X and A are selected from halogen atoms, the position and physical data of the products in the group -X.

19Ι 006 ___ 2 / Table χ ....... Ν ~

Η Η Η Η Η Η Η Η Η Η Η Η Η Η Η Η Η

Η Η

Η Η Η Η Η Η

S

S0 so ₂ ο

S

S0

S02 ο

S ο

S ο

ο 'CCI {ΊΚ Ί -CChCHCI

-Cd CIKI CCHCHCI

Η Η

Η Η

Η Η

Η Η

Η Η

Η Η

Η Η

Η Η

Η Η

Η Η

Η Η

Η Η

6-0 II

6-CI Η

6-0 Η

6-0 Η

6-0 Η

6-CI II

Η

6-0 Η

6-OCHj Η

6-0CH Η

6-OCH ³ H

S ο

S ο

S ο

ο ο

ο

S ο

ο ο

ο ο

ο ο

ο ο

ο ο

ο ο

CH -CCl 2 -CH <Cl ₂ (II CCI,

ΟΙ ΟΊ ~

CINCII (Π2 -ClljCII CH, ch ₂ c-ch ₂ ^{c ,,} 3 ch ₂ ocli ^ <CH ₂ ) ₂ ci £ ch ₂ (Cll ₂ ) ₃ ClhCH ₂

CH ₃

-ch ₂ -cicc ^Π, 3 ch ₂ cii = cc »i ₃

-CH ₂ -CH = CHCH ₃

-CII ₂ CH = CHCH ₃ ch ₃

CH

CH-CHCl

CH

CH = CH ₂

-CH ₂ OCH,

-ch ₉ -oc ₂ h,

-CH ₂ -S-CH ₃

-CII ₂ CH ₂ -OCH ₃

-CH ₂ CH ₂ -OCH ₃

-CH ₂ CH ₂ -OC ₂ FI ₅

-ClkCHySCíV

-CH ₂ CH <H ₂ ch ₃

-CH ₂ -C = CH ₂ ch ₃

-ch ₂ -ch = c ch ₃ .ch ₂ och, {CFkKOCH-j

-CH ₂ SCH ₂

-CH ₂ -Cl 1 = CH-CH ₃

-ch ₂ -ch = ch ₂

CH

-CH ₂ -C = CH ₂ <cif ₂ ) ₂ -oc ₂ h ₅ ch ₃

-X-A's position

Physical data ~ ÖfÖ47- Í49®

104-105 °

Mp 104-105 °

Mp 113 ° C-4 ° C

Decomposition from 12 l °

2

Mp 110-112 °

127-128 °

191 006 __2. spreadsheet__

Rj R ₂ X

-X-Á 'Physical data position

6-OCH 3 H

6-OCH ₃ H

6-CH 3 H

6-CH ₃ H

6-CH ₃ H

6-CH, H

Η H

6-NO ₂ H

6-NO 2 H

6-NO ₂ H

6-NO ₂ H

6-NO ₂ H

6-COOCH, H

5-Cl H

5-CI H

5-Br H.

5-Br H.

5-Br H.

5-F H

5-F H

SHE

SHE

SHE

CH

5-CH

5-CH

CH

5-CH ch ₃

5-CH

5 <h2

5-CH ₃

5-NO ₂

5-NO ₂

5-NO

5-OCft ₃

H

H

H

H

H

H

H

H

H

5-OCH

5-OCH ₃

5-OCH ₃

5-OCH

Cl £ -CON

H

H

H

H

Oh o

o o

-C1LCH-C ch ₃

- (CH ₂ ) ₂ -CH = CH ₂

-ch ₂ -Ch = ch ₂ ch,

-ch ₂ -c = ch ₂

- (citvoatj

-CH ₂ SCH ₃

-CH ₂ CH ₂ -OCH ₂ CH = CH ₂

-CH ₂ -CH = CFU

-ch ₂ -ch = chÍ: h ₃

-CH ₂ -OCH ₃

-CH ₂ -CH ₂ -OC ₂ H ₅

-ch ₂ -c <^ h ₂

-ch ₂ -ch = cr ₂

-ch ₂ -ch = cb ₂

· CH,

-ch ₂ -c = ch

CH, ch -, - c = ch,

-ch ₂ -ch = cFi ₂

-ch ₂ -och ₃

-CH ₂ -CHCH ₂ ch ₃

-ch ₂ -ch <

CH

CH

-CH ₂ -CH = C ch ₃

-ch ₂ -ch = ch ₂

-CH ₂ -CH ₂ -OCH ₃ .

T

122 °

Mp 110-111 °

Mp 113-114 °

CH

CH

-CH ₂ CH ₂ OCH ₃

-CH ₂ -CH = CH ₂

-ch ₂ -ch = ch ch ₃

-ch ₂ -ch = ch-ch ₃

-CH ₂ -S-CH ₃

-ch ₂ ch = ch,

-ch ₂ ch = ch;

CH

-CH ₂ -C = CH ₂

-CH ₂ CH = CH-CH ₃

-ch ₂ and ₃

-ch ₂ ch ₂ -sch ₃

-CH ₂ -ClUCH ₂ oil

Mp 139-140 ° 2 2 2

138-141 °

Mp 88-89 °

CH-101

191,006

^R 1 - -χ- THE -X Your position Physical data 5-OCN ^CH 3 5COOCH ₃ H 0 UH ₂ -C-CH ₂ 2 H 0 -CH ₂ -CH <H ₂ 2 ch ₃ 5-COOCH ₃ H 0 -ch ₂ -c = ch ₂ 2 5 j-COOCH H 0 -CHyOCHJk -CH ₂ -CH = CT1 ₂ 2 5-NO ₂ -CF 3, 0 2 ⁵ ' ⁿ ° 2 3-Cl 0 -CH ₂ -CH = CH ₂ 2 5-NO ₂ 3-Cl 0 ch ₃ -ch ₂ -c = ch ₂ 2 5-CF ₃ 3-NO ₂ 0 -ch ₂ -ch = ch ₂ 2 5-CH ₃ 3-CH ₃ 0 -ch ₂ -ch = ch ₂ 2 5-CH 3-CH ₃ 0 -ch ₂ -ch = ch ch ₃ -CH ₂ -CH = CH-CII ₃ 2 5-Cl 3-NO ₂ 0 2 5-Cl 3-Cl 0 -ch ₂ -ch = ch ₂ -ch ₂ -ch ₂ -och ₃ ch ₂ -och 2 Mp 161-162 ° 5-Cl 3-Cl 0 2 5-Cl 3-Cl 0 2 5-Br 3-OCH ₃ She -CH ₂ -CH = CH ₂ -ch ₂ -ch = ch ₂ 2 5-Br 2-OCH ₃ 5-COOCH ₃ 0 3 resin 3-OCH ₃ 0 CH, CH = CH 2 ch ₃ ² 2-OCH 5-COOCH, 0 -ch ₂ -c = Ch ₂ 3 5-CH 3-Br 0 -ch ₂ -och ₃ 2 3 5-Br 3-NO 0 -CH ₂ CH = CH ₂ -ch ₂ -ch <h ₂ 2 5-Cl 3-Br " 0 2 Mp 179 ° 5-Cl 3-Br 0 CH, -CH ₂ -C = CH ₂ -CH ₂ -CH ₂ -OCH ₃ 2 5-Cl 3-Br 0 3 H H salt -CH ₂ -CH = CH ₂ 2 H H salt. -CH ₂ -CH = CH ₂ 2 H H salt -CH ₂ -CH = CH-c _h 3 2 H H S ° 2 -CH ₂ -CH = CH-CH ₃ 2 H H 0 -ch ₂ so-ch. 2 H H 0 -CH ₂ -SO ₂ -CH ₃ 2 H H 0 -CH ₉ -CH ₂ -SO ₉ -CH ₃ 2 cl H H 0 -CH ₂ -C = CH ₂ 2 cl H H 0 -CH ₂ -C = CH-Cl 2 cl H H She -CH ₂ -CH = C-CH ₃ 2 cl H H 0 -ch ₂ -ch < 2 cl cl 5-CH H 0 -ch ₂ -c = ch ₂ 2 cl 5-NO, H She -CH ₂ C = CH-Cl 2 cl 5-Br H 0 -CH ₂ -C = CH ₂ 2

(Ί li

-111

191,006

2..táVláaL.

-π; -x

A -X A 'Physics? position of data

5-C 1 H

5- CH (CH ₃ ) ₂ H

3-CH 3 H

6- CH ₃ H

6-OCH ₃ H

5- OCH ₃ H

6- Cl H

3-NO ₂ H

3-CH ₃ H

3-NO ₂ H

3-Cl H

3-Cl H

3-C 1 H

3-OCH ₃ H

3-OCH ₃ H

2-OCH ₃ H

-CII ₂ CK = C Cl

cl

O -CH ₂ C ₁ C-Cn ₃ Cl

-CU ₂ -C-CH ₂

cl

O -CH ₂ -C <II ₂

cl

-CH ₂ -C = ClIC 1

cl

O -CH ₂ -CII-C

cl

cl

O -CH ₂ -C <H ₂ Cl

-CH ₂ -CH = C ('H ₃

O -CH ₂ -C 1ICH ₂

O -Cl ₁₂ CH = CH ₂

O -CH ₂ C1FCII ₂

O -CH ₂ -CH = CHCl ₃

C.)

O -CHyCAll-j

-CH ₂ -C = Clk

O -CH ₂ -CH = CH ₂

O -CH ₂ -CH = CH ₂

114-116 ° 2 2

Mp 113-114 °) 2

-121

191,006

3, Table

^R 1 K --- ™ A · tendon The situation H H 0 1 2 6 <OOCH ₂ CH ₃ H 0 ^Cl2 F2 1 2 6-COOCH ₂ CH ₃ H s GIF, 1 2 6-j-COOCH H salt chf; 1 2 6-COOCH ₃ CH ₃ H so ₂ CHF " I 2 6-C1 5-C1 ) CI1F ₂ 1 2 6-C1 5-Cl s chf ₂ I 2 6-C1 5-Cl salt -CHF-, 1 2 6-Cl 5-Cl- so ₂ -C11F ₂ 1 2 H 5-CF ₃ She chf ₂ 1 2 H 5-CF ₃ s chf ₂ 1 2 H 5-CF ₃ salt chf ₂ I 2 H 5-CF ₃ so ₂ · Cili, 1 2 H H 0 chf ₇ 2 2.5 H H s chf ₂ 2 2.5 H 11 salt -CNF, 2 2.5 H H so ₂ CHF, 2 2.5 H 6-NO ₂ 0 ⁽ ' ^{,, p} 2 1 3 6-COOCH CH ₃ 6-COOCH ^ CH ₃ H H 0 s ^CF 3 ⁿ 3 1 1 2 2 6-COOCH ₂ CH H salt ^CF 3 1 2 6-COOCH ₂ CH ₃ 6-COOCH ₂ CH ₃ H H so _? 0 ^{ 'i {P ₂ rln ₂ 1 1 2 2 6-COOCH ₂ CH ₃ H s -CF ₂ C! IF ₂ 1 2 6-COOCH ₂ CH ₃ 6-COOCH ₂ CH ₃ H salt -CF / 'HF _? 1 2 H so ₂ -cf ₂ chf ₂ 1 2 3-F H 0 -CH _? F 1 2 3-Br H She CíkF 1 2 5-Cl H 0 -CIHF 1 2 H 6-OCH ₃ 0 -cu, r ] 2 5-SCH H 0 -ClkF 1 2 5-CH H 0 -CH ₂ F 1 2 5-Br H 0 -CHF-, 1 2 H 6-F 0 -ch ₂ f 1 2 5-N ° 2 H 0 -chf ₇ 1 2 5-SO ₂ CH ₃ H 0 CH, f 1 2 H H s ^C 2 ^F 5 1 2 H H salt ^F 2 ^F 5 1 2 H H so ₂ ^C 2 ^F 5 1 2 H 5-F 0 -ch ₇ f 1 2 6-F H 0 c ₂ f ₅ 1 2 H 5-F 0 ^C 2 ^H 5 1 2 H 6-COOCH ₂ CH ₃ 0 CF 1 3 H 6-COOCH ₂ CH ₃ s ^CF 3 1 3 yl 6-COOCH ₂ CH ₃ salt ^CF 3 1 3 H 6-COOCH ₂ CH ₃ SALT-, 1 3 (1 ({ 0 ' ^CF 2 ^CF 2 ^CI 1 2 11 () -CF ₂ CF ₇ Br 1 2 11 11 0 CIlvClLl 1 2 11 11 s -cil gi / 1 2 ! 1 II s - (Τζ {Ί · ₂ ? 1 1 2

Mp 145-146 ^

176-178 °

Pizikaí data

-131

3, Table continued 191,006 Table 3 ; ^R i r ₂ X ........... Λ m -ΧΆ Physical data - situations. H H 0 -CF ₂ -CIL 1 cH ₂ -ccr ₃ 1 2 H H s 2 H II 0 CF ₂ CI 1 2 H H salt CF ₂ CI 1 2 H II S (K -CF ₂ C1 1 -CH ₂ -CH, ci 1 2 H H 0 2 110 ° H H s ch -, - ch; ci 1 / l {F * 1 <hf ₂ 1 2 • " 6-COOCH3 H 0 2 6-NO ₂ H 0 2 H H 0 -CF ₃ 1 2 Mp 176-178 ° H H s CF. 1 2 H H salt cf ₃ 1 2 H H so ₂ -CF ₃ 1 2 H 11 0 <HF ₂ 1 2 Mp 128-130 ° H H s -CHF ₂ 1 2 Mp 141-142 ° H H salt -CHF ₂ 1 2 158-160 ° H H so ₂ 0 CHF, I -CFj-CHClF 1 CF ₂ -CHCl 1 CF ₂ -CHCIF 1 2 H H 2 H H s 2 H H salt 2 H 11 so ₂ CF ₂ CHCl 3 2 H 11 0 CF ₂ Cfir ₂ 1 2 Mp 116-118 ° H H s CF ₂ -CHF ₂ 1 2 H H salt CF ₂ -CHI ₂ 1 2 H H so ₂ CF ₂ -CHF ₂ 1 2 H H 0 CFjCHBiF 1 CF ₂ -CHBfF 1 2 H H s 2 H H salt CF ₂ CHBiF 1 2 H H so ₂ 0 CFyCHBiF 1 -chf ₂ 1 2 6-Cl II 2 M.p. 90-95 ° 6-C1 II s chf ₂ 1 2 6-C1 H salt -chf ₂ 1 2 6-Cl H _S O ₂ -chf ₂ 1 -CHF ₂ 1 CF ₂ .CirciF 1 -CFyCHCIF 1 CF _? CHCIF | 2 H 5-Cl 2 Op 129 Ι3Γ H 5-Cl s 2 H 5ΓΙ salt 2 11 5-C1 SO ₂ 2 H 5-Cl SHE CFn 1 2 H 5 -Cl s -CF ₃ 1 2 H 5-F s -CHF ₂ 1 2 H 5-F 0 -CHF ₂ 1 2 Mp 138-140 ° H 5-F salt CHF ₂ 1 2 H 5-F SALT-, -CHF _? 1 2 H 5 (Ί so ⁷ • CF? 1 2 11 5-Cl ^so 2 -cf ₃ 1 2 H lithium s -cfh ₂ 1 3 H 11 salt -CHF ₂ 1 CIIF ₃ i -CHF ₂ l 3 II H SO ₂ 3 6-F II s ^z 2 14

-141

191,006

Continuation of Table 3

Table 3

^R 1 7 - _χ - THE m -3CX- The situation Physical data 6-F H so ₂ CHF, 1 2 6-F H so ₇ -CHF ₂ 1 2 H 6-CH ₃ 0 -chf ₂ 1 3 H ⁶ ' ^CH 3 s -chf ₂ 1 3 H 6-CH ₃ salt chf ₂ 1 3 H · 6-CH, so ~ -chf ₂ 1 3 H 6-C1 0 -chf ₂ 1 3 H 6-C1 s -chf ₂ 1 3 H 6-C1 salt -chf ₂ 1 3 H 6-C1 S0 ₇ chf _? 1 3 H 6-C1 o ² Cl · '-. 1 3 H 6-C1 s -C ^p 3 1 3 H 6-C1 salt ^<Ρ 3 1 3 H 6-C1 so ₀ * ^F 3 1 3 gas evolution

Example 5

(a) To a suspension of N- [2 (allyloxy) phenylsulfonylphenylcarbamate in 0.56 g of sodium hydride (55%) in 5 ml of absolute dimethylformamide at a temperature not exceeding 20 ° C under nitrogen for 5 minutes. 2.76 g of 2 (ayloxy) phenylsulfonamide in 20 ml of dimethylformamide are added dropwise and the mixture is stirred for about 10 minutes and then 2.91 g of N-phenylcarbamic acid phenyl ester dissolved in 20 ml of dimethylformamide are added dropwise. The mixture is stirred for 0.5 hour and then taken up in a mixture of 80 ml of ethyl acetate, 80 g of ice and 12.3 ml of 2N hydrochloric acid. The organic layer was washed twice with ice-water, dried over sodium sulfate (40) and evaporated, and the residue was crystallized from ether / petroleum ether (1: 1). 3.5 g of N- [2- (allyloxyphenylsulfonylphenyl) carbamate are thus obtained.

Mp 140-141 C.

_b ) N - [2- (Allyloxy-phenylsulfonyl) -N '- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) -urea

A mixture of 3.33 g of N- (2-allyloxyphenylsulfonyl) phenylcarbamate and 1.4 g of 2-amino-4-methoxy-6-methyl-1,3,5-triazine in 30 ml of absolute dioxane was added. After refluxing for 0.5 h, it was cooled to 20 ° C, filtered, concentrated and the residue was crystallized from ether and then recrystallized from ethyl acetate / petroleum ether 1: 1 to give 2.0 g of N. [2- (Allyloxyphenylsulfonyl) -N- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) urea is obtained.

Op. 146-147 ^b C.

Similarly, the compounds of formula (Ia) listed in the following table are also prepared. The table shows the serial number of the compound and the values of the substituents A, R 1, R 1, R 4, X and E.

-151

Table 4

The chemical- let number - _r π r ₃ É physical data First -CH ₂ -CH = CH ₂ 6-Cl ch ₃ and ₃ She N 142-145 ° 2 -CH ₂ -CH = CH ₂ 6-Cl ch ₃ and ₃ 0 CH Mp: 163-164 ° Third -CH ₂ -CH = CH ₂ 6-Cl and ₃ 0 N 4th -ch ₂ -ch = ch ₂ 6-Cl and ₃ 0 CH 5th -ch ₂ -ch = ch ₂ 6-Cl and ₃ and ₃ 0 N 6th CH, -ch ₂ -c = ch ₂ 6-C1 ch ₃ and ₃ 0 N ^CH 3 • 7th -CH ₂ -C = CH ₂ 6-Cl ch ₃ and ₃ 0 CH 8th CH, -CH ₂ -C = CH ₂ 6-Cl ^C 2 ^H 5 and ₃ 0 N 9th CH, -ch ₂ -c = ch ₂ 6-Cl and ₃ and ₃ 0 N 10th ch ₃ -ch ₂ -c = ch ₂ -CH ₂ -CH = CH-CH ₃ 6-Cl and ₃ ^and 3 0 CH 11th 6-Cl and ₃ and ₃ 0 CH 12th -CH ₂ -CH = CH-CH ₃ 6-Cl and ₃ and ₃ 0 N 13th -ch ₂ -ch = ch-ch ₃ 6-Cl and ₃ CH 0 N 14th -ch ₂ -ch = ch-ch ₃ 6-Cl and ₃ ch ₃ 0 CH CH 15th -CH ₉ -CH = C 6-Cl ^CH 3 and ₃ 0 N ^CH 3 16 -CH _? - ( 'H, C 6-Cl ch ₃ and ₃ 0 CH ch ₃ 17 -CH -OCH, 6-Cl ch ₃ and ₃ 0 CH 18th CH ₂ OCH ₃ 6-Cl ch ₃ and ₃ 0 N 19 -ch ₂ -och ₃ <ch ₉ ) ₉ -och ₃ 6-Cl cX and ₃ 0 N 20 6-Cl ch ₃ and ₃ 0 N 21 22 <ch ₂ ) ₂ -och ₃ jCH ₂ -SCH ₂ 6-Cl 6-Cl CH, ch ₃ och ₃ och ₃ 0 0 CH CH 23 -CH ₂ -SCH ₂ <ch ₂ ) ₂ -sch ₃ 6-Cl ch ₃ and ₃ 0 • N 24 6-Cl ch ₃ and ₃ 0 N 25 <ch ₉ ) ₉ -sch ₃ 6-Cl ch ₃ and ₃ 0 CH 26 -ch ₂ ch = ch ₂ 6-OCH ₃ CH and ₃ 0 CH 27 -ch ₂ ch = ch ₂ 6-OCH ₃ CH and ₃ 0 N 28 -ch ₂ ch = ch ₂ 6-OCH ₃ ^C 2 »5 OCH ₃ and ₃ 0 N 29 -ch ₂ ch = ch ₂ 6-OCH ₃ and ₃ 0 N 30 -ch ₉ ch = ch ₉ ^C «3 6-OCH ₃ and ₃ and ₃ 0 CH 31 -CH-C = CH ₉ 6-OCH ₃ and ₃ and ₃ 0 CH 32 ² ch, -CH ₂ -C = CH ₂ 6-OCH ₃ ch ₃ and ₃ 0 N 33 ch ₃ -ch ₂ -c = ch ₉ - {CH 2 H 6-OCH ₃ 6-Och3 CH and ₃ 0 CH 34 ch ₃ and ₃ 0 CH 35 - (CH ₂ ) ₂ -OC ₂ H ₅ ch ₃ -ch ₉ -ch = c 6-OCH ₃ ch ₃ and ₃ 0 N 36 6-Cl ch ₃ and ₃ 0 N CH 36 -ch ₂ -ch = c 6-Cl ch ₃ and ₃ 0 N

ch ₃

-161 .4. Continue Table

The end- let me wait --j.- ^R 1 'F - _r -F Physical data 37 -CH ₂ -CH = C 6-Cl CH ₃ and ₃ 0 CH ch ₃ cl 38 -ch-c = ch ₂ 6-OCH ₃ ch ₃ and ₃ 0 N the 39 -CH-C≡CH, 6OCH ₃ ch ₃ and ₃ . 0 CH cl 40 -CH = C = CH. 6-C1 ch ₃ and ₃ 0 CH Op. 163-164 ' '· cl 41 -CH-C = CH ₂ -ch ₂ -ch = ch ₂ 6-C1 ch ₃ and ₃ 0 N 142-145 * 42 6-CH ₃ ch ₃ and ₃ 0 N 43 -CH ₂ -CH = CH ₂ 6-CH ch ₃ och ₃ and ₃ 0 CH 44 -CH ₂ -CH = CH ₂ 6-CH and ₃ 0 CH 45 -ch ₂ -ch = ch ₂ 6CH | and ₃ and ₃ 0 N 46 ^CH 3 ch ₂ -c = Ch ₂ 6-CH ₃ ch ₃ and ₃ 0 N ch ₃ 47 -ch ₂ -c = ch ₂ 6-CH ₃ ch ₃ and ₃ 0 CH CH 48 -CH ₂ -C = CH ₂ 6-CH ₃ and ₃ and ₃ 0 N 49 CH, -ch ₂ -c = ch ₂ 6CH ₃ and ₃ and ₃ 0 CH 50 -CH ₂ -OCH ₃ 6-CH ₃ and ₃ and ₃ 0 CH 51 -CH -OCH ₃ 6-CH and ₃ ch. 0 CH 52 53 -ch2-och ₃ <ch ^) _? -ch = ch ₇ 6-CH ₃ 6-OCH ₃ och ₃ och ₃ ch ₃ ch ₃ 0 0 N ch 55 -ch ₂ -sch ₃ 6-CH ₃ and ₃ ch. 0 CH 56 -ch ₂ -sch ₃ -ch ₂ -ch = ch ₂ 6 € H ₃ OCH, ch ₃ 0 N 57 6-NO ₂ CH and ₃ 0 N 58 -CH ₂ -CH = CH ₂ 6-NO ₂ ^CH 3 and ₃ 0 CH 59 -ch ₂ -ch = ch ₂ 6-NO ₂ and ₃ and ₃ 0 CH 60 4? H ₂ -CH = CH ₂ 6-NO ₂ and ₃ and ₃ 0 N 61 -ch ₂ -ch = ch-ch ₃ 6-NO ₂ and ₃ and ₃ 0 N 62 -ch ₂ -ch = ch-ch ₃ 6-NO ₂ and ₃ and ₃ 0 CH 63rd -ch ₂ -ch = ch-ch ₃ 6-NO ₂ and ₃ ch. 0 CH 64th -ch ₂ -ch = ch-ch ₃ 6 female and ₃ ch ₃ 0 N 65th -ch ₂ -och ₃ 6-NO ₂ and ₃ CH? 0 N 66th -CH ₂ -0CH, -CH, -CH, -0C _? H _s 6-NO ₂ and ₃ ch. 0 CH 67th 6-NO ₂ and ₃ ch. 0 CH 68th -ch, -ch ₇ oc, h _s 6-NO ₂ and ₃ ch ₃ 0 N 69th ch ₃ -ch ₂ -c = ch ₂ 6-NO ₂ and ₃ ch ₃ 0 N 70th ch ₃ -ch ₂ -c = ch ₂ 6-NO ₂ 6-COOCH ₃ and ₃ ch. 0 CH 71st -ch ₂ -ch = ch ₂ and ₃ ch ₃ 0 CH 72nd -CH ₂ -CH = CH ₂ 6 COOCHj and ₃ ^CH 3 and ₃ 0 N 73rd -ch ₂ -ch = ch ₂ 6 COOCHj and ₃ 0 N 74th -CH ₂ -CH = CiF, 6-C00CH, OCH, and ₃ 0 CH 75th -CH ₂ -CH = CH ₂ 5-C1 CH and ₃ 0 N Mp: 164-166 ' 76th € H ₂ -CHCH ₂ / 5-Cl ch ₃ and ₃ 0 CH Mp: 197-198 '

-171

Continuation of Table 4

191,006

Table 4

-Τψ-17

The number of the chemical account

* T

Physical data

77 € H ₂ -CH = CH ₂ 5-Cl OCH 3 and ₃ . 0 N M.p. 173 ° 78th -ch ₂ -ch = ch ₂ 5-Cl and ₃ and ₃ 0 CH 79 -CH ₂ -CH = € H ₂ 5-Cl ^C 2 ^H 5 and ₃ 0 N po. CHj -ch ₂ -c = ch ₂ 5-Cl ch ₃ and ₃ 0 N M.p. 167 ° 81st CHj -ch ₂ -c = ch ₂ -ch ₂ ch = ch ₂ 5-Cl ch. and ₃ 0 CH 0p.:115° 82nd 5-Br CH and ₃ 0 CH 83rd -ch ₂ ch = ch ₂ 5-Br ch. OCH, 0 N M.p .: 190-191 ° 84th -ch ₂ ch = ch ₂ 5-Br ^C 2 »5 ch ₃ 0 - N ch ₃ 85th -ch-c = ch ₂ 5-Br ch ₃ and ₃ 0 N 86th ch ₃ -CH-C = CH ₂ 5-Br and ₃ and ₃ 0 N ch ₃ 87th -ch-c = ch ₂ 5-Br CH and ₃ 0 CH 88th ch ₂ and ₃ 5-Br CH- and ₃ 0 CH 89th -ch ₂ -och ₃ -ch ₂ -ch = Ch ₂ 5-Br CH and ₃ 0 N 90th 5-F ch ₃ and ₃ 0 N 159-161 ° 91st 92nd -ch ₂ -ch = ch ₂ -ch ₂ -ch = ch ₂ 5-F 5-F ch ₃ och ₃ and ₃ 0 0 CH N 200-201 ° 93rd -ch ₂ -ch = ch ^ 5-F and ₃ 0 CH 162-164 ° 94th -ch ₂ -ch = c ch ₃ ch ₃ 95th CH, CH = C 5-F ch ₃ OCH 0 CH ch ₃

96th

^CH 3

-ch ₂ c = ch ₂

CH

97th 98th -CH, -C = CH, ^{2 CH} 3 -ch ₂ -c = ch ₂ 5-F CH 5-CH CH ch ₃ ch ₃ och ₃ och ₃ 0 0 N N 99th ch ₃ -CH ₂ C = € H ₂ 1 5-CH ch ₃ ch ₃ and ₃ 0 CH CH ch ₃ ch ₃ 100th CH, CH-C 5-CH ch ₃ and ₃ 0 CH ch ₃ ch ₃ ch. ^CH 3 101 ch ₂ ch = c 5-CH ch ₃ and ₃ 0 N ch ₃ CH ch ₃ 102nd -ch ₂ ch = ch ₂ 5-CH ch ₃ and ₃ 0 N

CH.

-181

4, Table

Continuation of Table 4

191,006

The chemical- let number . •• - • χ THE ^R 1 -5T " E Physical data 103rd -ch ₂ -ch = ch ₂ 5-CH CH CH and ₃ 0 CH 139-140 ° 104th -ch ₂ -ch = ch ₂ 5-CH CH, ^CH 3 c ₂ h. and ₃ 0 N

105th ch ₃ N Op. 219-220 ° -ch ₂ -ch = ch ₂ 5-CH 1 ch ₃ and ₃ and ₃ 0 106th -CH ₂ -CH ₂ -OCH ₃ 5-CH ^CH 3 and ₃ 0 N ch ₃ ch ₃ 107th ch ₂ -ch ₂ -och ₃ 5-CH ch ₃ and ₃ 0 CH ch ₃ 108 -CH ₂ -CH ₂ -OCH ₃ 5-CH ₃ ch, and ₃ 0 CH 109th -ch ₂ -ch ₂ -och ₃ 5-CH ch, OCH, 0 N 110th -CH ₂ -CH ₂ -OCH ₃ 5-CH ₃ ^CH 3 cl 0 CH 111th -CH ₂ -CH ₂ -OCH ₃ 5-CH. och, cl 0 CH 112th -ch ₂ -ch = ch ₂ 5-CH ₃ ch ₃ OCH, 0 N 158-162 ° 113th -ch ₂ -ch = ch ₂ 5-CH ₃ and ₃ 0 N 114th -ch ₂ -ch = ch ₂ 5-CH ₃ ^C 2 ^H 5 and ₃ 0 N 115th -ch ₂ -ch = ch ₂ 5-CH ₃ and ₃ and ₃ 0 N 160-165 ° 116th -ch ₂ -ch = ch ₂ 5-CH ₃ and ₃ and ₃ 0 CH Op. 220-202 ' 117th -ch ₂ -ch = ch-ch ₃ 5-CH ₃ OCH, and ₃ 0 CH t 118th -CH ₂ -CH = CH-CH ₃ 5-CH CH and ₃ 0 CH Mp 179-182 ° 119th -ch ₂ -ch = ch-ch ₃ 5-CH ₃ ch. and ₃ 0 N 120th -ch ₂ -ch = ch-ch 5-NO ₂ CH and ₃ 0 N 121st -ch ₂ -ch = ch-ch | 5-NO ₂ ch ₃ and ₃ 0 CH 122nd -ch ₂ -ch = ch-ch ₃ 5-NO C ft and ₃ 0 N 123rd -ch ₂ -ch = ch-ch ₃ 5 Νθί and ₃ and ₃ 0 N 124th -ch ₂ -ch = cii ₂ 5-NO ₂ och. and ₃ 0 N 125th -ch ₂ -ch = ch ₂ 5-NO ₂ ch. and ₃ 0 N 131-132 ° 126th -ch ₂ -ch = ch ₂ 5 Νθί ch. and ₃ 0 CH 127th -ch ₂ -sch ₃ 5-NO ₂ ch. and ₃ 0 CH 128th -ch ₂ -sch ₃ 5-NO ₂ ch ₃ and ₃ 0 N 129th -CH ₂ -SCH ₃ 5-NO ₂ and ₃ and ₃ 0 N 130th -ch ₂ -sch ₃ 5-NO OCH, OCH 0 CH 131st -ch ₂ -ch = ch ₂ 5-OCH ₃ ch ₃ O ^ 0 N 142-143 ° 132nd -ch ₂ -ch = ch ₂ 5-OCH ₃ ch ₃ □ ^ch 3 0 CH Mp 138-139 ° 133rd 42H ₂ -CH = CH ₂ 5-OCH ₃ and ₃ and ₃ 0 CH 134th -CH ₂ -CH = CH ₂ 5-OCH ₃ and ₃ OCH, 0 N 135th -ch ₂ -ch = ch ₂ 5-OCH ₃ and ₃ ^C 2 ^H 5 0 N 136th ^CH 3 -ch ₂ -c = ch ₂ 5-OCH ₃ and ₃ ch ₃ 0 N 137th ^CH 3 ch ₂ -c = ch ₂ 5OCH ₃ and ₃ ch ₃ 0 CH ch ₃ 138th -ch ₂ -c = ch ₂ 5-OCH ₃ and ₃ OCH, 0 N 139th -ch ₂ -ch = ch _xh3 5-OCH ₃ OCH, ch ₃ 0 CH Γ41, -CH ₂ -CH = CH 11 ₁₃ 5-OCH ₃ ^0CH 3 and ₃ 0 CH 142nd -ch ₂ -ch = ch-ch ₃ 5OCH ₃ and ₃ and ₃ 0 N

-191

Continuation of Table 4

191,006

The number of the chemical

Table 4 —writes—

X E Physical data

143rd -ch ₂ -och ₃ -ch ₂ -och ₃ -ch ₂ -och ₃ 5-OCH ₃ OCH, and ₃ 0 N 144th 5-OCH ₃ ch ₃ and ₃ 0 N 145th 5-OCH CH OCH, 0 CH 146th -CHj-OCH, -ch ₂ -ch ₂ -sch ₃ 5-OCH ₃ ^c 2fl ₅ CH, OCH, 0 N 147th 5 OCHj and ₃ 0 N 148th -CH ₂ <H ₂ -SCH ₃ 5OCH ₃ ch ₃ and ₃ 0 CH 149th -ch ₂ -ch ₂ -sch ₃ 5-OCH ₃ and ₃ CH, and ₃ 0 N 150th -ch ₂ -ch = ch ₂ 5-CON CH, ch ₃ and ₃ 0 N 151st -CH ₂ -CH = CH ₂ 5-CON CH, ch ₃ OCH She CH 152nd ch ₃ -ch ₂ -c = ch ₂ 5-CON CH, ch ₃ and ₃ 0 N

153rd 154th -CH ₂ -C = CH ₂ CH, -ch ₂ -c = ch ₂ ch ₃ 5-CON 5 COOCHj ch ₃ ch ₃ och ₃ och ₃ 0 0 CH CH 155th -ch ₂ -c = ch. -CH ₂ -CH = CH ₂ 5 COOCHj CH and ₃ 0 N 156th 5 COOCHj 5-COOCH, CH OCH, OCH 0 N 157th -ch ₂ -ch = ch ₂ CH? OCH 0 CH 158th -ch ₂ -ch = ch ₂ 5 COOCHj 5 COOCHj and ₃ 0 N 159th -CH ₂ -CH = CH ₂ and ₃ OCH, 0 CH 160th -CH ₂ -OC ₂ H ₅ -OC ₂ H _-CH2-CH2-C = dH ₂ Cl, -CH ₂ -C = CH ₂ Cl, 5-COOCH, 5 COOCHj OCH OH, 0 N 161st and ₃ CH 0 N 162nd 5-CH3 and ₃ ch ₃ 0 N 163rd 5-CH 3 and ₃ ch ₃ 0 CH cl 164th -CH, -C = CH, 4. L cl 5-NO ₂ and ₃ CH? 0 CH 165th _CH2 = CH-C 1 -C 5-NO ₂ and ₃ CH? 0 N cl 166th -CH ₂ -C = CH-Cl 5-Br and ₃ CH? 0 N 167th -CHj-CH-C-Cl cl 5-Br OCH CH? 0 CH 168th _-CH2-C = CH-C1 5-Cl OCH CH? 0 N cl 169th -CH ₂ -C = CH ₂ 5-C1 CH3 and ₃ 0 CH cl 170th -CH, -CH = C ch ₃ Cl 5-Cl ch ₃ OCH 3 0 N 171st -CH ₂ -CH = C 5-C1 ^CH 3 OCH 0 CH CH, cl CH

Continue Table -201

Table 4

The chemical- let wing THE ^k i ^ft 3 -χ- -t- Physical data 172nd _-CH2 CIHC 5-CH ^CH 3 qch ₃ 0 CH cl cl CH CH 173rd CH, CH = C 5-CH ch ₃ and ₃ 0 N cl ch ₃ cl 174th -ch ₂ -c = ch ₂ 3-CH3 ch ₃ and ₃ 0 N cl 175 -CH ₂ -C = CH ₂ • 3-CH ₃ ch ₃ and ₃ 0 CH cl 176th -CH ₂ -C = CH ₂ 6-CH ₃ ^CH 3 and ₃ 0 N cl 177th -CH ₂ -CH = CH ₂ 6-CH ₃ ch ₃ and ₃ 0 CH cl 178th -CH ₂ -C <H ₂ 6-OCH ₃ ch ₃ and ₃ 0 CH cl 179th _-CH2-C = CH-C1 6-OCH ₃ ch ₃ and ₃ 0 N cl 180th -CH ₂ -CH = C . 5-OCH3 ch ₃ and ₃ 0 N cl cl 181st -ch ₂ -ch = c 5-CH ₃ ch ₃ and ₃ 0 CH cl - Cl 182nd -ch ₂ -c-ch ₂ 6-C1 ch ₃ and ₃ 0 N cl 183rd -CH ₂ -C = € H ~ -ch ₂ -ch = ch ₂ 6-C1 CH and ₃ 0 CH 184th 3- ⁿ ° ₂ CH and ₃ 0 CH 185th -ch ₂ -ch = ch ₂ 3-NO ₂ ch ₃ and ₃ 0 N 186th -CH ₂ -CH = Cl ₁₂ 3-NO ₂ and ₃ 0 N 187th -ch ₂ -ch = ch ₂ 3- ⁿ ° ₂ and ₃ 0 N 188th -ch ₂ -c = ch ₂ 3-NO ₂ ch ₃ ³ and ₃ 0 N 189, CH, -ch ₂ -c = ch ₂ 3- ⁿ ° ₂ ch ₃ and ₃ 0 CH 190th ^ch 3 -ch ₂ -c = ch ₂ 3-NO ₂ and ₃ and ₃ 0 N 191st CH, ch ₂ -c = ch ₂ 3-NO ₂ and ₃ and ₃ 0 CH

192nd -CH ₂ -CH = C-CH ₃ Cl 3-NO ₂ and ₃ 0CH ₃ 0 CH cl 193 -CH.-CH = C-CH α 3-NO ₂ and ₃ ch ₃ 0 CH 194 -CH ₂ -CiHC-CH ₃ 3-NO ₂ and ₃ CH 0 N 195 -ch ₂ -ch = ch ₂ 3-CH ₃ and ₃ CH 0 N Mp 255-256 * 196 -ch ₂ -ch = ch ₂ 3-CHL and ₃ CH 0 CH Op. 163-164 ' 197 -CH ₂ -CH = C1u 3-CH ₃ CH 0 N 198 -ch ₂ -ch = ch ₂ 3-CH CH 0 N Op. 183-184 ' 199 -CH ₂ -CH = CH ₂ 34¾ OCH 3 ch ₃ 0 CH

-214. Continue Table

4, Table

The chemical- let number - · .. --¾. _ THE -rf r ₄ "T T Physical data 200 -CH ₂ -CH = CH ₉ 3-C1 ^0CH 3 CH 0 N Mp 183-187 ° 201 -CH ₂ -CH = € H ₂ 3-C1 and ₃ ch ₃ 0 N 202 -ch ₂ -ch = ch ₂ 3-C1 and ₃ OCH, 0 N 203 CH, CH = CH, 3-C1 and ₃ OCH- 0 CH 204 ^CH 3 -ch, -c = ch, ch ₃ 3-C1 and ₃ and ₃ 0 N 205 -CH, -C = CH ₂ 3-C1 and ₃ ch ₃ 0 N 206 -CH ₂ -C = CH ₂ 3-C1 OCH, CH 0 CH 207 -CH ₂ -CH = CH-CH ₃ 3-C1 CH / OCH, 0 N 208 -ch ₂ -ch = ch-ch. 3-C1 ^CH 3 OCH, 0 CH ch ₃ 209 -ch ₂ -c = ch ₂ 3-OCH ₃ ch ₃ and ₃ 0 CH 210 ^CH 3 -ch ₂ -c = ch ₂ 3-OCH ₃ ch ₃ ^0CH 3 0 N 211 -CH _? -CH = CH ₂ 3-OCH CH OCH, 0 N 212 -CH ₂ -CH = CH ₂ 3-OCH ₃ ^CH 3 ^0CH 3 0 CH 213 -ch ₂ -ch = ch ₂ 3-OCH ₃ OCH, and ₃ 0 CH 214 -ch ₂ -ch = ch ₂ 3-OCH ₃ C-H and ₃ 0 N 215 -ch ₂ -ch = ch ₂ 3-OCH ₃ ° ^ 3 and ₃ 0 N Table 5 1 Compounds of general formula (1b) Example THE R ³ R ⁴ X E Physics data

number

301 « ch _{3 is} -CH, -C = CH-CH ₃ ^CH 3 ^CH 3 0 N 95-103 ° 302 -ch ₂ -c = ch ₂ ch ₃ och ₃ 0 N 142-143 ° 303 -ch ₂ -c = ch ₃ och ₃ och ₃ 0 N Mp 145-153 ° 304 ch ₃ -ch ₂ -c = ch ₂ och ₃ oc ₂ h ₅ 0 N 305 ch ₃ -CH, -C = CHch ₃ ² -ch ₂ -ch ₃ och ₃ 0 N Op. 150-152 ' 306 -ch ₂ -c = ch ₂ -ch ₂ -ch ₃ ch ₃ 0 N Mp 129-130 ° 307 ch ₃ -ch ₂ -c = ch ₂ -Cl and ₃ 0 N 308 CH? -CH, - (> CH -OCH / ch _3/2 och ₃ 0 N 309 CFK -CH, -C = CH -OCH / ch _3/2 och ₃ 0 N 310 ch ₃ -ch ₂ -c = ch ₂ -OCH / ch _{3/2 CH3} 0 N ch ₃

-221

Continuation of Table 5

Example number THE -p, R ⁴ X E Physics .data 311 -CH ₂ -C = CH ₂ -0CH ₃ sch ₃ 0 N ch ₃ 312 -ch ₂ -c = ch ₂ -och ₂ h _s oc ₂ h ₅ 0 N Op, 118-120 ' ch ₃ 313 -ch ₂ -c = ch ₂ ch ₃ -och ₃ -ch ₂ -och ₃ 0 N 314 -ch ₂ -c = ch ₂ -CH ₂ a and ₃ 0 N ch ₃ 315 -ch ₂ -c = ch ₂ -ch ₂ f and ₃ 0 N Oh ₃ 316 -CH ₂ -C = CH ₂ -ch ₃ and ₃ 0 CH 172-177 ^ch 3 317 ch ₂ -c = cg ₂ -och ₃ and ₃ 0 CH M.p. 218-219 ° ch ₃ 318 -ch ₂ -c = ch ₂ ch ₃ ch ₃ 0 CH ch ₃ 319 -ch ₂ -c = ch ₂ ^C 2 ^H 5 and ₃ 0 CH ch ₃ 320 -CH _n -C = CH, and ₃ the 0 CH Mp 179-180 ' ^CH 3 321 -ch ₂ -c = ch ₂ ch ₃ the 0 CH ^CH 3 322 -ch ₂ -c = £ h ₂ - ·· ^CH 3 cf ₃ and ₃ 0 CH 323 -ch ₂ -c = ch ₂ ch ₃ -ch ₂ -och ₃ OCH 3 0 CH 324 -ch ₂ -c = ch, Ól Br and ₃ 0 CH 325 -CH _? -C = CH ₂ Br ^CH 3 0 CH 6h ₃ 326 -ch ₂ -c = ch ₂ and ₃ SCL ^ 0 CH ^CH 3 327 -CH ₂ -C = CH ₂ ch ₃ ^SCIi 3 0 CH ^CH 3 328 -ch ₂ -c = ch ₂ and ₃ oc ₂ h ₅ 0 CH 329 -ch ₂ -ch = ch-ch ₃ CH and ₃ 0 N Mp 163-164 330 -CH ₂ -CH = CH.CH ₃ ch ₃ ^CH 3 0 N 331 -ch ₂ -ch = ch-ch ₃ and ₃ 0 N Mp 139-140 ' 332 CH 0 N Op. 148-151 ' 333 -ch ₂ -ch = ch-ch ₃ and ₃ 0 N Mp 148-149 334 -CH ₂ -CH = CH-CH ₃ och. oc ₂ il 0 N 335 -ch ₂ -ch = ch-ch ₃ oc ₂ h ₅ -CH - OCH, S ' ^! 0 N 100-193 ' 336 -ch ₂ -ch = ch-ch ₃ 0 N 337 -CH ₂ -CH = CH-CH ₃ ch ₃ ² and ₃ 0 CH 185-186 ' 338 339 -ch-ch = ch-ch ₃ -CH ₂ -CH = CH-CH ₃ OCH, ^CH 3 -CH - OCH, och, ch ₃ 0 0 CH CH 340 -CH ₂ -CH = CH-CH ₃ OCH, 0 CH 341 -ch ₂ -ch = ch-ch ₃ ch ₃ och ₃ cl 0 CH 342 -ch ₂ -ch = ch-ch ₃ cl 0 CH M.p. 193-195 ° 343 -CH ₂ -CH <H-CH ₃ and ₃ OC ₂ ^H 5 0 CH

CH?

-231

Continuation of Table 5

191,006

Mace ~ AR ³ 'R ⁴ XE number

344 CH CH? CH 3 and ₃ 0 N 345 -CH, -CH = C, CH ch ₃ ch ₃ 0 N 346 -CH, -CH = C CH, ^CH 3 ^C 2 ^H 5 ch ₃ 0 N 347 CH, CH = C CH CH ^C 2 ^H 5 and ₃ 0 N 348 -CH, -CH = CH, ch ₃ and ₃ and ₃ 0 N 349 -CH - CH-C CH and ₃ oc ₂ h ₅ 0 N 350 CH, CH = CH CH CH, CH = C CH <* 2 ^H 5 oc ₂ H ₅ 0 N 351 -ch ₂ -och ₃ and ₃ 0 N 352 CH, CH = C CH <4 ch ₃ and ₃ 0 CH 353 CH ₂ -CH = C CH, CH, and ₃ and ₃ 0 CH 354 -CH, -CH = C CH, ^CH 3 ch ₃ ch ₃ 0 CH 355 -CH, -CH = C CH, CH ₃ and ₃ cl 0 CH 356, -ch ₂ -ch = c ch ₃ cl 0 CH

CH.

357 -CH, -CH = C ch ₃ Cl OCH 3 oc ₂ h ₅ 0 CH 358 -CH ₂ -C = CH ₂ Cl ch ₃ OCH 3 0  N 359 -CH ₂ -C = CH ₂ Cl ch ₃ ch ₃ 0 CH 360 -CH, -C = CH, cl ^C 2 ^H 5 ch ₃ 0 N 361 -CH, -C = CH, -CH, -CCHC1 ^C 2 ^H 5 and ₃ 0 N 362 and ₃ and ₃ 0 N 363 -CH, -C «CH ² Cl and ₃ oc ₂ h ₅ 0 N

Mp 141-145 '

Payment data

162-164 '

Mp 165-158 '

100-105 '

Op. 150-152 '

-241

5, Table continued

191,006

Example number THE R ³ R ⁴ X E Physics data 364 -ch ₂ c = ch ₂ Cl -ch ₂ -c = ch ₂ Cl ° c ₂ h ₅ ^OC 2 ^H 5 ⁵ 0 N 365 -ch ₂ -och ₃ and ₃ 0 N • 366 -ch ₂ -c = ch ₂ Cl ch ₃ OCH, 0 CH 367 -CH ₂ -C = CH ₂ Cl and ₃ and ₃ 0 ch 202-205 ° 368 -ch ₂ -c = ch ₂ Cl and ₃ and ₃ 0 CH 202-205 369 -ch ₂ -c = ch ₂ Cl and ₃ cl 0 CH 370 -CH ₂ -C = CH ₂ Cl ch ₃ cl 0 CH 371 -CH ₂ -C = CH ₂ Cl -CH ₂ -C = CH ₂ oc ₂ h ₅ ocn ₃ 0 CH 372 -CH _? -OCH, ^CH 3 and ₃ 0 CH 373 -CH ₂ -OCH ₃ ocr ₃ 0 N 155-157 ° 374 -CH ₂ OCH ₃ and ₃ and ₃ 0 N 375 -CHyOCH, ^C 2 ^H 5 0¾ OCH, CH 0 N 376 · -CH ₂ -OCH ₃ 0 N 377 -CH ₂ -OCH ₃ and ₃ 0 N 378 -CH ₂ -OCH ₃ and ₃ oc ₂ h ₅ 0 N 379 -CH ₂ -OCH ₃ OC, Ης oc ^ 0 N 380 -CH ₂ -OCH ₃ -CH, -0CH, OCH ₃ 0 N 381 -ch ₂ -och ₃ OCíL SCH, 0 N 382 -ch ₂ -och. and ₃ ch ₃ 0 CH Mp 168-175 * 383 -ch ₂ -och ₃ a and ₃ and ₃ 0 CH 384 -CH ₂ -OCH ₃ ch ₃ ch ₃ 0 CH 385 -ch ₂ -och ₃ ^CH 3 cl 0 CH 137-143 ° 386 -CH ₂ -OCH ₃ and ₃ the 0 CH 387 -ch ₂ -och ₃ 0¾ and ₃ 0 CH 388 -ch ₂ -och ₃ a and ₃ 0 CH 389 -ch ₂ c = ch ₂ ^CH 3 ^C 2 ^H 5 and ₃ 0 CH 390 -CH ₉ -CH = C ^CH 3 C ₂ ^H 5 and ₃ 0 CH 391 -CH ₂ -CH = CH-CH ₃ Title ⁵ and ₃ 0 CH 392 -CH ₂ -S-CH ₃ OCH, 0 N 141-143 ° 393 -ch ₂ -s-ch ₃ ^CH 3 CH 0 N 394 -CH ₂ -S-CH ₃ cClean ^CH 3 and ₃ 0 N 395 -CH ₂ -S-CH ₃ 0 N 396 -ch ₂ -s-ch ₃ OCH, 0 N 397 -CH ₂ -S-CH ₃ and ₃ ocJ ₅ OCH ₃ och ₃ 0 N 398 -CH ₂ -S-CH ₃ -CH y S -CH ₃ -ch ₂ -och ₃ CR, 0 N 399 0 CH 169-171 ° 400 -CH ₂ -SCH ₃ OCR, OCH, 0 CH 401 -CH ₂ -S-CH ₃ -CH ₂ -S-CH ₃ ^CH 3 ch ₃ 0 CH 402 c ₂ n ₄ 03 -ch ₂ -sch ₃ and ₃ the O CH

-251

5. Continue Table

Example number THE R ³ R ⁴ X E Fizi. data '403 -CHj-S-CIf OCH cl 0 CH 404 -ch ₂ -s-ch ₃ CH ₃ the 0 CH 405 -CH ₂ -S-CH ₃ OCH, OC, H, 0 CH 406 -CH ₂ -CH _? OCH ₂ H _s CH OCH, 0 N 118-120 ° 407 -CH ₂ -CH ₂ -OC ₂ H <; , CH ₃ ch ₃ 0 N 408 -CHyCHyOqH ,. cJ, 0 N 409 410 -CH ₂ -CH ₂ -OC ₂ H ₅ CH ₂ OC ₉ H ₉ -CH <; . OCR, och ₃ 0 0 N N Op. 186-188 ' 411 -ch ₉ -ch ₂ -oc ₉ h _s ^CH 3 and ₃ 0 CH 412 -CH ₂ -CH ₂ -OC ₂ H ^ and ₃ och. 0 CH 163-164 ° Mp 166-168 ° ' 413 -CH ₂ -CH ₂ -OCH ₃ OCH, the 0 CH 414 -CH ₂ -CH yOCH ₃ CH cl 0 CH 432 _-CH2 -SO-rH ₃ ch ₃ ^0CH 3 0 N 433 .CH ₂ -CO-Cl ₃ -CH ₂ -SO-CH ₃ ^CH 3 and ₃ and ₃ 0 CH 434 och. 0 N 435 -ch ₂ -so-ch- -CH ₂ -SO ₂ -CH ₃ and ₃ OCH, 0 CH 436 och. OCH ₃ 0 CH 437 -ch ₂ -so ₂ -ch ₃ ch. OCH, 0 CH 438 -ch ₂ -so ₂ -ch ₃ -CH ₂ -SO ₂ -CH ₃ ch. ^CH 3 OCH, OCH ₃ 0 CH 439 ^CH 3 0 N 440 -ch ₂ -so, ch ₃ ^CH 2 ' ^CH 2' ^SOc H ₃ och. 0 N 441 and ₃ and ₃ 0 N 442 '-CH ₂ -CH ₂ -SO ₂ -CH, and ₃ CH She N 174-175 ° 443 -ch ₂ -ch ₂ so-ch, ^0CH 3 CH 0 CH 444 -CH ₂ -CH ₂ -SO ₂ -CH, and ₃ CH 0 CH 445 -CH ₂ -CH ₂ -SO ₉ -CH, OCH, ch ₃ och ₃ 0 N Mp 183-185 ' 446 -CH, -CH, -SO, -CH, crf ₃ ch ₃ 0 N 149-151 ° 449 -CH ₂ -CH = C ch ₃ and ₃ s CH CH ^CH 3 450 -ch ₂ -ch = c ch ₃ and ₃ s N 453 ch ₃ -CH ₂ -CH ₂ -OCH ₃ CH and ₃ s CH 454th -CH ₂ -CH ₂ -OCH <ch ₂ ) ₂ -ch = ch ^ ch. ^0CH 3 s N 127-128 ° 455 CH and ₃ 0 N 456 <ch ₂ ) ₂ -ch = ch ₂ 3 ™ och 0 CH 457 - (CH ₂ ) ₂ -CH = CH ₂ CH? ch ₃ 0 N 458 <ch ₂ ) ₂ -ch = ch ₇ CH ^CH 3 0 CH 459 / ch ₂ ) ₃ -ch = ch ₂ CH ₃ ocft ₃ 0 N 460 - (CH ₂ ) - CH = CH ₉ ch ₃ OCH ₃ 0 CH ch ₃ 461 CH ch ₃ and ₃ 0 N

CH = CH ₂ ch ₃

462 -CH ch = ch ₂ ch ₃ and ₃ 0 CH 463 -ch ₂ -oc ^ h ₅ ch ₃ and ₃ 0 CH 464 -ChI -OC ^ k CH and ₃ 0 N 465 -CH ₂ -OC ₂ H ₅ ^{C 2} 5 and ₃ 0 N

2o

-261 'Continuation of Table 3 ..

191,006

Example number

AR ³ R ⁴

E 'Physics. data

466 -CH ₂ -OC ₂ H ₅ CH CH 0 N 467 CH ₂ OC ₂ H ₅ -CH ₂ CH ₂ OC ₂ H ₅ -CH ₂ CH ₂ -OCH ₃ CH, ^CH 3 and ₃ CH, ch ₃ OC 1 0 CH 468 469 0 0 CH N Mp 179-180 ° Mp 141-142 ° 470 -ch ₂ -ch ₂ -och ₃ CH OCH ₃ 0 N 134-138 ° 471 -CH ₂ -CH ₂ -OCH ₃ -CH ₂ -CH ₂ -SCH ₃ CH and ₃ 0 CH 160-162 ° 472 CH and ₃ 0 CH 473 -ch ₂ -ch ₂ -sch ₃ a. -CH ₂ -C = CH-Cl Cl -CH ₂ -C = CH-a CI1 ₃ and ₃ 0 N Op.'116-117 ° 474 CH ₃ and ₃ 0 N 180-182 ° 475 ch ₃ and ₃ 0 CH cl 476 -CH ₂ -CH = C-CH ₃ ^CH 3 and ₃ 0 CH cl 477 ^{CH 2} -CH = C-CH, Cl ³ ch ₃ and ₃ 0 N 479 -ch ₂ -ch = c a a ch ₃ and ₃ 0 N 479 / a. -ch ₂ -ch = ch ch ₃ and ₃ 0 CH the 480 -CH ₂ -CH ₂ -CCH ₂ - ch ₃ and ₃ 0 CH , -CH = CH ₂ 481 -CH _r CH, -C-CH, -CH <? H ₂ ch ₃ and ₃ 0 N 482 -ca = cci ₂ ch ₃ and ₃ 0 N 483 -CC1 = CHC1 ^0CH 3 and ₃ 0 N OP. 244-246 ° 484 -CC1 = CC1 ₂ och, ^CH 3 och, CH, OCH ₃ and ₃ 0 N 485 -CC1 = CC1 ₂ and ₃ 0 OH 486 -CC1 = CC1 ₂ och, 0 CH 487 -CC1 = CC1 ₂ cl 0 CH 488 -CC1 = CC1 ₂ cl 0 N 489 -cf = cf ₂ OCH, the 0 N 49Ö -cf = cf ₂ CH OCH, cl 0 CH 491 -ch = cci ₂ OCH ₃ ^0CH 3 0 N 492 -CH6CC1 ₂ ^CH 3 and ₃ 0 CH 493 -ch = cci ₂ and ₃ 0 CH 494 -CH = ca ₂ ^C 2 ^H 5 5¾ och ₃ och ₃ 0 N 495 -CF = CF ₂ -CG = CHCl 0 N 496 and ₃ s N 169-172 ° 497 -CCFCHG ^CH 3 and ₃ 0 N 169-172 ° 498 -CCFCHCl C ₂ ri OCH, 0 N 499 -CC1 = CHC1 ch ₃ ⁵ CH 0 N 500 -CC1 = CHCl and ₃ cl 0 CH Mp 196-198 ' 501 -CCFCHC1 and ₃ OC _? H _S OCR? 0 N 168-169 ° 502 -CCFCHC1 and ₃ 0 CH 503 -CCl = CHCl address £ ⁵ OCH, 0 CH 504 -CCKHCl Cl ³ 0 CH 505 -CCl = CHD ^CH 3 OCH ₃ s CH 506 -CC1 = CHC1 OCH, OCH, s CH

-271>. Resume table

191,006

Example number THE r3 R ⁴ X E Fizla. data 507 -cf = cf ₂ ^CH 3 OCH She - N 508 -cf = cf ₂ OCH and ₃ 0 N 509 -cf = cf ₂ CH? OCH 0 CH 510 -cf = cf ₂ and ₃ and ₃ 0 CH 511 -ch ₂ -ch = ch ₂ -CH (CH 3) ₂ and ₃ 0 CH 512 -ch ₂ -ch = ch ₂ OCH SCJ1, 0 CH 513 ch ₂ -ch = ch ₂ ^0CH 3 sc: h; 0 N 514 -ch ₂ -ch = ch ₂ OCH -SC 11 (CH 3) ₉ 0 N 515 -ch ₂ -ch = ch ₂  the CH? 0 N Op. 128-130 ' 516 -ch ₂ -ch = ch ₂ CH? Br 0 N 517 -ch ₂ -ch = ch ₂ chf ₂ OCH 0 N 518 -ch ₂ -ch = ch ₂ chf ₂ CH? 0 N 519 -CH ₂ -CH = CH ₂ CH-CFj ³ 0 N 520 -CH ₂ -CH = CH ₂ CH, CF, OCH 0 N 521 -ch ₂ -ch = ch ₂ -CHyCF, ^CH 3 0 N 522 -ch ₂ -ch = ch ₂ OCX oc ₉ h < 0 N Op. 138-142 ' 523 -ch ₂ -ch = ch ₂ OC, H, <. oc ₉ h. 0 CH 524 -ch ₂ -ch = ch ₂ C ₂ fl ₅ and ₃ 0 N Op. 206 ' 525 -CH ₂ -CH = CH ₂ c H ₅ oc ₂ h ₅ 0 N 526 -ch ₂ -ch = ch ₂ cflj ⁵ oc ₉ h. 0 N Op.129-131 " 527 -ch ₂ -ch = ch ₂ CH? ^CH 3 0 CH 180-182 ' 528 -ch ₂ -ch = ch ₂ CH? OCH 0 CH 98-100 ° 529 -ch ₂ -ch = ch ₂ CH? Η 0 N 530 -ch ₂ -ch = ch ₂ ^C 2 '5 cl 0 CH ) 531 -ch ₂ -chch ₂ C ^H 5 cl 0 CH 532 -ch ₂ -ch = ch ₂ CH3 ⁵ cl 0 CH Op. 153-154 ' 533 -ch ₂ ch = ch ₂ CH? SCHj 0 CH 534 -ch ₂ -ch = ch ₂ CH? F ³ 0 CH 535 -ch ₂ -ch = ch ₂ CH? Br 0 CH 536 -CH ₂ -CH = CH ₂ ^C 2 ”5 OC, H, 0 CH 537 -ch ₂ -ch = ch ₂ c ₂ h ₅ SCHj 0 CH 538 -ch ₂ -ch = ch ₂ ^C Y CH? 0 CH 539 -ch ₂ -ch = ch ₂ CFLC1 CH ³ 0 CH 540 -ch ₂ -ch = ch ₂ ch ₂ ci OCH 0 CH 541 -CH ₂ -CH = CH ₂ OCH cl 0 CH Mp 173-179 * 542 -ch ₂ -ch = ch ₂ ³ cl 0 CH 543 -ch ₂ -ch = ch ₂ OCH SCHj 0 CH 544 • ch ₂ -ch = ch ₂ OCH -OCH (CH 3 O) CH 545 -CH ₂ -CH = CH ₂ ch ₉ f OCH 0 CH 546 -ch ₂ -ch = ch ₂ CH ₉ F CH? 0 CH 547 -ch ₂ -ch = ch ₂ CF? OCH 0 CH 548 -ch ₂ -ch = ch ₂ ^C 2 & 5 -OCH (CH 3) ₀ O N 549 -CH ₂ CH = CH ₂ ^C 2 ^H 5 cl 0 N 550 -CH ₂ -CH = € H _? ^C 2 ^H 5 SCHj 0 N 551 -ch ₂ -ch = ch ₂ ^C 2 ^H 5 CH? 0 N Op.128-131 ° 552 -ch ₂ -ch = ch ₂ C, H ⁵ cX 0 N 553 -ch ₂ -ch = ch ₂ OCIL -och (ch ₃ ) ₂ O N 119-120 ' 554 -ch ₂ -ch = ch ₂ OCH ₂ -OCH (CH 3) 0 N CH2CH 555 -ch ₂ -ch = ch ₂ ^CH 3 -CH (CH 3) ₉ O N 96-98 ' 556 -ch ₂ -ch = ch ₂ -ch (ch ₃ ) ₂ the 0 N

-281

Continuation of Table 5

Example number THE R ³ R ⁴ X E Physics .data 557 -ch ₂ -ch = ch ₂ -CHÍCH ^ k and ₃ 0 N 124-128 " 558 -CH ₂ -CH = CH ₂ -CH (CH 3) _{2 5} OC2H 0 N 559 -CHj-ClKIU CH (CH.). sch. 0 N 560 -ch ₂ -ch = ch ₂ ch ₂ ci ch ₃ 0 N 561 -CH ₂ -CH = € H ₂ ch ₂ g OCH. 0 N 562 -ch ₂ -ch = ch ₂ ch ₂ f ^CH 3 OCH. 0 N 563 -ch ₂ -ch = ch ₂ ch ₂ f 0 N 564 -CH ₂ -CH = CH ₂ ch ₂ f -ch ₂ -och ₃ OC.H. 0 N 565 -CH ₂ -CH = CH ₂ 0 N 566 ~ ch ₂ -ch = ch ₂ -CH _r SCH " 0 N 567 -ch ₂ -ch = ch ₂ -ch ₇ -sch ₃ CH. 0 N 568 -CH ₂ -CH = CH ₂ -CH ₂ -SCH ₃ SCH. 0 N 569 -ch ₂ -ch = ch ₂ -ch ₂ -sch ₃ ci ³ 0 N 570 -ch ₂ ch = ch ₂ -ch ₇ -sch ₃ oc ₂ h ₅ 0 N 571 -ch ₂ -ch = ch ₂ SC1L cl 0 N 572 -ch ₂ -ch = ch ₂ sch ₃ and ₃ 0 N 573 -ch ₂ -ch <h ₂ sch ₃ oc ₂ h ₅ 0 N ch ₃ 574 -CH ₂ -CH = CH ₂ SCH ₃ OCH She N CH. 575 -CH ₂ -CH = CH ₂ -OCH (CH ₃ ), cl 0 N 576 -ch ₂ -ch = ch ₂ cf ₃ and ₃ 0 N 577 -CH ₂ -CH = CH ₂ cf ₃ ^CH 3 0 N 578 -ch ₂ -ch = ch ₂ ^CF 3 oc ₇ h. 0 N 579 -ch ₂ ch = ch ₂ cci. and ₃ 0 NN 580 -ch ₂ -ch = ch ₂ CCL SCH. 0 N 581 -ch ₂ -ch = ch ₂ ^CH 3 and ₃ the 0 N 128-130 * 582 -ch ₂ -ch = ch ₂ cl 0 N 583 -ch ₂ -ch = ch ₂ and ₃ F 0 N 584 -ch ₂ -ch = ch ₂ and ₃ Br 0 N 585 -ch ₂ -ch = ch ₂ ^CH 3 OCH. F 0 N 586 -ch ₂ -ch = ch ₂ OCH. 0 CH Mp 184-186 ° 587 -CH -CH = CH. 2 ² ch ₃ ³ 3 ™ 0 N 139-141 ° 588 -CH ₂ -CH = CH ₂ and ₃ oc ₇ h _s 0 N 589 -CH ₂ -CH = CH ₂ och ₃ ch ₇ och ₃ 0C.h ₅ och ₃ 0 CH 590 -CH ₂ -CH = CH ₂ 0 CH 591 -CH ₂ -CH = CH ₂ ch ₂ and ₃ and ₃ 0 N 592 593 -CH-CH = CH ₂ -CH ² -CH = CH ₂ cLÓch ₃ and ₃ OCH. CH ₃ and ₃ 0 0 CH N 595 -CH ^ -CH = _CH2 0 N Mp 148-149 ° 596 -CHCHC1 ch. and ₃ 0 N 597 -CII-CHCl ch ₃ and ₃ s N 598 -CC1 = CHC1 ch ₃ and ₃ 0 CH M.p. 208-209 ° 599 -CH = CH _{1 2} ^CH 3 and ₃ 0 N 600 -CC1 = CHC1 and ₃ and ₃ 0 N 199-200 ° 601 -CH ₂ -CH = CH ₂ ch ₃ and ₃ 0 N 146-147 °

-291

191,006

Example number R ³ 5.a. Spreadsheet Compounds of formula (Ib) E R ^h X 650 -ch ₂ -ch <h ₂ -CH ^ -CH-OCH ^ CH ÖCH, She N 651 ch ₃ ^and 3 0 N 652 -CCl = CIIA ^CH 3 and ₃ 0 N 653 654 ch ₂ -och ₃ -ch ₂ -ch = ch <h ₃ och ₃ och ₃ 0 0 N N 655 -CH ₂ -C (CH ₃ ) = CH ₂ > ^CH 3 and ₃ 0 N

Table 6 Compounds of Formula Ic

Compound A X-A R ¹ R ² X E 701 ch ₂ -ch = ch ₂ 4 2CK ₃ H 0 N 702 -ch ₂ -ch = ch ₂ 5 2-CH ₃ H 0 CH 703 ^CH 3 -ch ₃ -c = ch ₂ 5 ^2CH 3 11 0 CH 704 ^CH 3 -ch ₃ -c = ch ₂ 5 2C1K H 0 N 705 -CH ₂ -CH = CH-CH ₃ 5 2-CH ₃ II 0 N 706 -ch ₂ -ch = chch ₃ 5 2CH ₃ H 0 CH cl 707 -CH ₂ -C = CH ₂ 5 2-CH ₃ H 0 CH cl 708 -CH ₂ -C = CH ₂ 5 2-CH H 0 N 709 -CH ₂ -Cll = cn ₂ 5 · 2 Cl '' H 0 N 710 -CH ₂ -CH = CH ₂ 5 2-Cl H 0 CH cl 711 -CH ₂ -C = CH ₂ 5 2-Cl H 0 CH cl 712 -CH ₂ -C = CH ₂ 5 2-Cl H 0 N 713 ch ₃ -CH ₀ -C = CH ~ 5 2-Cl H 0 N 714 ^CH 3 ch ₂ -c = ch ₂ 5 2-Cl H 0 CH 715 -CH ₂ -OCH ₃ 5 2-Cl H 0 CH 716 -CH ₂ -O-CH ₃ 5 2-Cl H 0 N 717 -CHyS-cil 5 2-Cl H 0 N 718 -CH ₂ -S-CH ₃ 5 2-Cl H 0 CH 719 -CH ₂ -CH = <7H _{rH 3} 5 2-Cl H 0 CH 720 -CH ₂ -CH = CH-CH ₃ 5 2-Cl H 0 N 721 -ch ₂ -ch ₂ -ch ₃ 5 2-a H 0 N 722 -CH ₂ -CH ₂ -OCH ₃ 5 2-Cl H 0 CH 723 -CHyOCÍH, 5 2-Cl H 0 N 724 -CHOC-H? 5 2-Cl H 0 CH 725 -CH ₂ -CH ₇ -SCH ₃ 5 2-Cl H 0 CH 726 -CHyCHySCH, 5 2-Cl H "0 N 727 -ch ₂ -ch <: h ₂ 3 2-CH ₃ H 0 N

-301

Continuation of Table 6

191 006

Table 6

Formula (Ic) compounds The compound X-A R ¹ R ² X E 728 -CH ₂ -CH = CH ₂ 3 2-CH ₃ H 0 CH 729 CH, -CH ₂ -C = £ H ₂ CH, 3 2-CH ₃ H 0 CH 730 -ch ₂ -c = ch ₂ -CH ₂ -CH = CH ₂ 3. 2-CH H 0 N 731 • 3 2-OCH ₃ H 0 N 732 -ch ₂ -ch = ch ₂ 3 2-OCH ₃ H 0 CH 733 ^CH 3 -ch ₂ -c = ch ₂ . 3 2-OCH ₃ H 0 CH 734 - ^ch 3 -CH, -C = CH, 3 2-OCH ₃ H 0 N 735 ^CH 3 -ch ₂ -c = ch ₂ ^CH 3 3 2-OCH ₃ H 0 N 736 -ch ₂ -c = ch ₂ 3 2-OCH ₃ H 0 CH 737 -ch ₂ -ch = ch-ch. 3 2-OCH ₃ H 0 CH 738 -ch ₂ -ch = chch ₃ 3 2-OCH ₃ H 0 N 739 -ch ₂ -ch = ch ₂ 5 2-OCH ₃ H 0 N 740 -ch ₂ -ch = ch ₂ ^CH 3 5 2-OCH ₃ H 0 CH 741 -CH _? -C = CH, 5 2-OCH ₃ H 0 CH 742 CH, -Clk-C-Cf L -CH ₂ -CH = CH-CH ₃ Cl 5 2 OCTL H 0 N 744 5 2-OCH ₃ H 0 CH 745 -CH ₂ -C = CH ₂ 5 2-OCH ₃ H 0 CH 746 -ch ₂ -c = ch ₂ -ch ₂ -ch = ch ₂ 5 2-OCH H 0 N 747 3 5-B, ³ 2-OCH 0 N 748 -CH ₂ -CH = CH ₂ 3 5-Br 2-OCH ₃ 0 CH 749 CH, -ch ₂ -c = ch ₂ ^CH 3 3 5-Br 2-OCH ₃ 0 CH 750 -ch ₂ -c = ch ₂ -ch ₂ -ch = ch 3 Five-br 2-OCH ₃ 0 N 751 3 5-COOCH ₃ 2-OCH 0 N 752 -CH ₂ -CH = CH ² 3 5COOCH ₃ 2-OCH ₃ 0 CH 753 ^CH 3 -CH ₂ -C = CH ₂ CH, 3 5-COOCH ₃ 2-OCH ₃ 0 CH 754 -ch ₂ -c = ch ₂ -ch ₂ -ch = chch ₃ 3 5-COOCH ₃ 2-OCH ₃ 0 N 755 3 5-COOCH ₃ 2-OCH ₃ c N 756 -CH ₂ -CH ₄ CH-CH ₃ 3 5-COOCH ₂ 2-OCH 0 CH 757 -ch ₂ -ch = ch ₂ 2 5-NO ₂ 2-CF 0 N 758 -ch ₂ -ch = ch ₂ 2 5-NO ₂ 3-CF ₃ 0 CH 759 -ch ₂ -ch = ch ₂ 2 5-NO ₂ 3-C1 0 CH 760 -ch ₂ -ch = ch ₂ • 2 5-NO ₂ 3-C1 0 N 761 CH, -ch, -c = ch, ch ₃ 2 5-NO ₂ 3-C1 0 N 762 -CH ₂ C = Cl ₁₂ 2 5-NO ₂ 3 -Cl 0 CH • 763 -ch ₂ -ch = ch ₂ 2 5-CF 3-NO ₂ 0 CH 764 -ch ₂ -ch = ch ₂ 2 5-CF ₃ 3-NO ₂ 0 N

Mp 258-259 ° mp 156-157 °

-312

Continuation of Table 6

191 006

Table 6 Compounds of formula Ic

Compound A X-A R ¹ R ² X r- E 7Ó5 -ch ₂ -ch = ch ₂ 2 5-CH ^3CH 3 0 N 766 -ch ₂ -chch ₂ 2 5-CH 3 3-CH 0 CH 767 -ch ₂ -ch = ch-ch ₃ 2 5-CH ₃ 3-CH ₃ 0 CH 768 -ch ₂ -ch = ch-ch ₃ 2 5-ch ₃ ^3CH 3 0 N 769 -CHCH = CH-CH ₃ -CH ₂ -CH = CH-CH ₃ 2 5-a ^3NO 2 0 N 770 2 5-Cl 3-NO ₂ 0 CH 771 -ch ₂ -ch = ch ₂ -CHyCHCH 1 2 5-a 3-NO 0 CH 772 2 5-a 3-NO? 0 N 773 -ch ₂ -ch = ch ₂ 2 5-a 3-a 0 N 774 • -CH ₂ -CH-CH ₂ -ch ₂ -ch _? -och ₃ 2 5-a 3-Cl 0 CH 775 2 5-Cl 3-a 0 CH 776 -CHyCHloCHo -ch ₂ -och ₃ 2 . 5-a 3-a 0 N 777 2 5-a 3-a 0 N 778 -CH, -OCH 2 5-C 3-a 0 CH 779 CH, ³ -ch ₂ -c = ch ₂ 2 5-a 3-a 0 CH ch ₃ 780 -ch ₂ -c = ch ₂ -CH ₂ -CH = CH ₂ 2 5-a 3-a 0 N 781 2 5-Br 3-o ₃ 0 N 782 -ch ₂ -ch = ch ₂ 2 5-Br 3-OCH ₃ 0 CH 783 ch ₂ -ch = ch ₂ 3 5-Br 2-OCH ₃ 0 CH 784 -CH ₂ -CH = CH ₂ 3 5-Br 2-OCH ₃ 0 N 785 -ch ₂ -ch = ch ₂ 2 5 COOCHj 3-OCH ₃ 0 N 786 '-ch ₂ -ch = ch _? 2 5-COOCH, 3-OCH ₃ 0 CH 787 -CH ₂ -CH = CH ₂ 3 5-COOCH ₃ 2-OCH ₃ 0 CH 788 -ch ₂ -ch = ch ₂ 3 5-COOCH ₃ 2-OCH ₃ 0 N 789 CH, -CH ₂ -C = CH ₂ 3 5-COOCH ₃ 2-OCH ₃ 0 N 790 CH, -ch ₂ -c = ch ₂ 3 5-COOCH ₃ 2-OCH 0 CH 791 -CH ₂ -CH = <? H ₂ 2 5-CH ₃ 3-Br 0 CH 792 -ch ₂ -ch = ch ₂ 2 5-CH ₃ 3-Br 0 N 793 -ch ₂ -och ₃ 2 5-CH ₃ 3-Br 0 N 794 -ch ₂ -och, -ch ₂ -ch = ch ₂ 2 5-CH 3-Br 0 CH 795 2 5-Br 3-NO ₂ 0 N 796 -ch ₂ -ch = ch ₂ 2 5-Br 3-NO 0 CH 797 -ch ₂ -ch = ch ₂ 2 5-a 3-Br 0 CH 798 -ch ₂ -ch = ch ₂ 2 5-a 3-Br 0 N Op. 799 CHj -ch ₂ -c <h ₂ 2 5-a 3-Br 0 N 800 CH, -ch ₂ -c = ch ₂ 2 s-a 3-Br 0 CH 801 -CH ₂ -CH ₂ -O-CH _q 2 5-a 3-Br 0 CH 802 -CH ₂ -CH ₂ -O-CH ₃ -CH ₂ -O-d ₃ 2 5-a 3-Br 0 N 803 5 2-NO H 0 CH 804 -CH ₂ -O-CH ₃ -CH ₂ -CH ₂ -OCH _3, -CH ₂ -CH = £ _H2 3 H ¹ H s CH 805 806 2 2 5-OC ₉ H ₄ -H -och; 5-0CH, -CH = CH- H 0 0 N N 807 -CH ₂ -OCH ₃ -ch ₂ -ch ₂ -och ₃ 2 5-OCH, OCH 5 H 0 N 808 2 5-SC ₂ H ₄ -OCH ₃ Η s N

-321

Continuation of Table 6 191 006 X-A Table 6 Compounds of formula (le) The compound THE R ¹ R ² X E ...... 809 -ch ₂ -sch ₃ 2 5-S-CLK-SCIk II s N 810 -ch ₂ -so-ch ₃ 2 5-S-Clk-SOCl ₃ II s N 811 -CH ₂ -SO ₂ -CH ₃ 2 5-CH ₂ SO ₂ ClI ₃ H s N

Example 6

a) N- (2- (Difluoromethoxyphenylsulfonyl) phenylcarbamate

To a suspension of 0.84 g of a 57.5% sodium hydride dispersion in 5 ml of absolute dimethylformamide and cooled to 0-10 ° is added 4.5 g of 2- (difluoromethoxy / phenylsulfonemide) in 5 ml of absolute dimethylformamide. To complete the evolution of hydrogen, the reaction mixture is heated to 25 DEG C. with stirring. After completion of the evolution of hydrogen, the mixture is cooled to -30 DEG C. and 4.7 g of N-phenylcarbamic acid phenyl ester (5 ml.) are added. After stirring for 18 hours, the reaction mixture was allowed to warm to 25 DEG C. The reaction mixture was poured into a mixture of 11 ml of 2N hydrochloric acid and 100 g of ice, and the precipitated product was taken up in ethyl acetate. The residue was recrystallized from methanol to give 5.6 g of (n - [- (difluoromethoxy) phenylsulfonyl] phenylcarbamate) as colorless crystals, m.p. 115-117 °.

b) N- [2- (Difluoromethoxyphenylsulfonyl) -N- (4-ethyl-6-methoxy-1,3,5-triazin-2-yl) urea

5.4 g N- [2- (difluoromethoxy) phenylsulfonyl P-phenylcarbamate and 2.42 g 2-amino-4-ethyl-6-methoxyl-1,3,5-triazine in 60 ml absolute dioxane The resulting solution was heated under reflux for 5 hours and then poured into 600 ml of ice water. The precipitated product is taken up in ethyl acetate, washed with water, dried and evaporated. This gives an oil which is redissolved in ethyl acetate and washed five times with saturated sodium bicarbonate solution. The combined aqueous layers were acidified with dilute hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layer was dried and evaporated, and the residue was recrystallized from methanol. 5.1 g of N- [2- (difluoromethoxy-phenylsulfonyl) -N- (4-ethyl-6-ethoxy-1,3,5-triazin-2-yl) -urea are obtained, m.p. .

Example 7

N- [2- (Difluoromethoxy) phenyl] sulfonyl] -N- [4-chloro-6-methylpyrimidin-2-yl urea

The procedure of Example 90 was followed and N- [2- (difluoromethoxy) phenylsulfonyl) isocyanate was reacted with 2-amino-4-chloro-6-methylpyrimidine to afford N- [2- (difluoromethyl) pyrimidine. methoxy) phenylsulfonyl-N- (4-chloro-6-methylpyrimidin-2-yl) urea. 190-191 °

Example 8

a) N- [2- (Difluoromethoxy) phenylsulfonyl] -4,6-dichloro-1,3,5-triazin-2-yl] -urea

To a solution of 3.9 g of 4,6-dichloro-2-isocyanato-1,3,5-triazine in 50 ml of absolute dioxane is added

4.5 g of 2- (difluoromethoxyphenylsulfonamide) was heated at reflux for 5 hours and then the resulting clear solution was poured into ice water. The precipitated product was extracted with ethyl acetate, the organic phase was dried and concentrated. 8.5 g of product are obtained which is dioxane and N- [2- (difluoromethoxy) phenylsulfonyl] -N / 4,6-dichloro-1,3,5-triazine-2-N-urea. 105: 107 °.

b) Ν- [2 / 4ίΠιιθΓ-ηιβΙοχϊ) 46ηϋ-8ζη1ΓοηίΙ] -Ν - [4,6-ethoxy-1,3,5-tyrazin-2-yl] -urea

5.5 g of 8a. to a solution of the N- [2- (difluoromethoxy) phenylsulfonyl] -N74,6-dichloro 1,3,5-triazin-2-yl / urea / dioxane adduct obtained in example 10 in absolute ethanol λ, - A solution of 1.9 ml of sodium ethylate in 10 ml of absolute ethanol is added dropwise over 1 minute. The reaction mixture was heated at reflux for 2 hours, then concentrated and the residue was dissolved in 200 ml of ice water and then acidified with dilute hydrochloric acid. Thus, 3.2 g of N- [220- (dichloromethoxy) phenylsulfonyl] -N- (4,6-diethoxy-1,3,5-triazin-2-yl) -urea are obtained in the form of colorless crystals. 117-118 °.

Example 9

a) N- [2- (Pentafluoroethoxy) phenylsulfonyl] -N-methyl35 urea

4b. The 2-pentafluoroethoxy) -phenylsulfonamide obtained in Example 1b is suspended in 400 ml of methylene chloride. To the suspension was added 16.3 g of methyl isocyanate, followed by the dropwise addition of 28.2 g of triethylamine over 15 minutes. A clear solution is formed, which is completely evaporated. The residue was dissolved in 5% sodium bicarbonate solution and acidified again with 10% hydrochloric acid. This gives 74.6 g of N- [2- (pentafluoroethoxy) phenylsulfonyl] -N-methylurea. 177-179 °.

2- (Pentafluoroethoxy) phenylsulfonylisoclanate, 74.6 g of N- [2- (pentafluoroethoxy) phenylsulfonyl] -N-methylurea are suspended in 1300 ml of chlorobenzene and azeotropically distilled off about 100 ml of solvent. make the suspension absolute. Subsequently, 48 g of phosgene were introduced into the suspension at 120-130 ° C for 3 hours, and the chlorobenzene was completely distilled off. 65 g of 2- (pentafluoroethoxy) phenylsulfonyl isocyanate are thus obtained in the form of a colorless oil. .

c) N- [2- (Pentafluoroethoxy) phenylsulfonyl] -N- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) urea

3.2 g of 2- {pentafluoroethoxy phenyl phenylsulfonyl isocyanate and 1.4 g of 2-amino-4-ethoxy-6-methyl-1,3,5-triazine are mixed with 40 ml of absolute dioxane for 90 hours to 100 ml. ° C. The solution is then cooled to 20 °, filtered and concentrated to about 1/4 of its volume. From the residue, 50 g of ether add 3.3 g of N- (2-pentafluoroethoxy) phenylsulfonyl) -N 33

-331,4 / 4-methoxyl-6-methyl-1,3,5-trlazine-241 / carbamyl is also added. 157-159 *.

Example 10

N- [2- (trifluoromethoxy) phenylsulfonyl] -N- [4-methoxyl-6-methyl-1,3,5-triazine-24H] -carbamyl

5.4 g of a solution of N- [2-difluoromethoxyphenylsulfonyl] phenylcarbamate and 2.2 g of 2-amino-4-methoxyl-6-methyl-1,3,5-triazine in 60 ml of absolute dloxane. The mixture is heated at reflux for 1 hour and then poured into 600 nd of ice water. The precipitated product is taken up in ethyl acetate, washed with water, dried and evaporated. This gave an oil which was redissolved in ethyl acetate, washed five times with saturated sodium bicarbonate solution, the combined aqueous phases acidified with HCl HCl and extracted with ethyl acetate. The ethyl acetate layer was dried and evaporated and the residue was recrystallized from methanol. There was thus obtained 5.0 g of N- [2-difluoromethoxy-phenylsulfonyl] -N74-methoxyl-6-methyl-1,3,5-triazin-2-yl-urea, m.p. 132-134 ° C. .

Example 11

N- [2- (difluoromethyl-tl-phenylsulfonyl) -N- [4-methoxy-6-methyl-13,5-trlazine -2-N] -urea

3a-b. in the same way as in the example

From 2-difluoromethyl ⁺ -o-aniline Starting with ld and sulfonyl chloride, 2-difluoromethylthiophenylsulfonamide is obtained, m.p. 141-142 °. Is converted to 2-difluoromethyl-thiophenylsulfonyl] -phenylcarbamate and

2-Amino-4-methoxy-6-methyl-1,3,5-triazinyl-9-yl is reacted with N- [2-difluoromethyl-thiophenylsulfonyl] -N- [4-methoxy-6-methyl-1,3]. , 5-triazin-2-yl) urea. 169-172.

Example 12

N- [2- (difluoromethoxy-phenylsulfonyl) -N- (4,6-dimethoxy-1,3,5-triazin-2-yl) -urea

5.5 g of 7a. Example 15 A solution of N- [2-difluoromethoxyphenylsulfonyl] -N- (4,6-dichloro-1,3,5-triazln-2-yl) -urea / dloxane adduct prepared in 10 ml absolute methanol was prepared in 15 minutes. a solution of 1.5 g of sodium methylate in 10 ml of absolute methanol is added dropwise. The mixture was heated at reflux for 2 hours, then concentrated and the residue dissolved in 200 ml of ice water. The solution was acidified with dilute hydrochloric acid

3.2 g of N- [2- (difluoromethoxy) phenylsulfonyl] -N- (4,6-dlmethoxy-1,3,5-triazol-2-l)) urea are obtained in the form of colorless crystals. 135-137 °.

Example 12.1

N- [2- (dl Fluoromethoxy) -phenylsulfonyl] -N < 4 &gt;

To a solution of 4.5 g of 2-difluoromethylxenylphenylsulfonamide in 50 ml of dloxane is added dropwise at 20-25 ° C 5.5 g of N <4,6-dimethoxymethyl-pyrhnidine-241) -phenylcarbamate in 50 ml of dloxane. solution. After stirring the reaction mixture for 3 hours, the solvent was evaporated. The residue was dissolved in water (100 mL) and treated with IN hydrochloric acid. The precipitate was collected and dried, yielding 6.8 g of N- [2- (dichloromethoxy) -phenyl] -N- (4,6-dbnethoxymethyl-n-2-U) -carbamide, m.p. 152-154 ° C.

Example 12.2

Sodium salt of N- [2- (methoxy-ethoxy) -phenyl] sulfonyl] -N '- (4-methoxy-16-methyl-1,3,5-triazine-2-fl) -carbamyl,

To a solution of 4.0 g of N- (2-methoxyethoxy) -phenylsulfonyl-N '- (4-methoxy-5-methyl) -1,3,5-trlazin-2-yl) urea in 50 ml of methanol was added a solution of 20 g. A solution of 0.4 g of sodium hydroxide in 30 ml of methanol is added at 25 ° C. The volume of the solution is reduced to 30 ml by evaporation of the solvent. The precipitated salt was isolated and dried, 3.8 g of N- [2-methoxy-ethoxy) -phenylsulfonyl] -N '- 4-methoxy-6-methyl] -1,3,5-triazin-2-yl} -carbanide. m.p. 205208 ° C.

Example 12.3

N- [2- (methoxy-ethoxy) -phenylsulfonyl] -N- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) -urea-1,4-diazabicyclo [2.2.2. ] octane salt

To a solution of 4.0 g of N- (2-methoxy-ethoxy) -phenylsulfonyl] -N'-4-methoxy-o-methyl-13.5-triazin-2-l) -carbamide in 50 ml of acetonitrile was added 20-25 °. 1.1 g at C

1,4-Diazabicyclo [2.2.2] octane is added. The solution was evaporated to dryness and the residue treated with a small amount of acetone-ether. The precipitated salt was collected and dried, yielding 4.5 g of N- [2-methoxy-ethoxy] -phenylsulfonyl] -N <4-methoxy-6-methyl-1,3,5-triazine-2-yl] -carbamyl. l, 4-dlazabiciklo [2.2.2.] octane salt, which melts at 100-105 ^e C (dec).

In a similar manner, the compounds listed in the following table were prepared. In the table, in addition to the exemplary number, the meaning of the substituents A, E, R ₃ , R * and X, the physical characteristics of the compounds are also indicated.

-341

191 006

Table 7 Compounds of Formula Ib

THE E ^R 3 ^R 4 X Physical data ^CH 2 N ^OC 2 ^H 5 OC Η 0 117-118 ° CHF, CH 0C, H, oc ₂ h, N0Ü ₄ fi _q 0 146-152 ° chf ₂ N · CH 0 shrinks from 110 ° cf ₃ N 0C, H, ^oc 2h ₅ 0 158-160 ° ^CF 3 CH OC ₂ ^H 5 0 cf ₃ N ch ₃ OC ^ Hq 0 -CF _r CHF ₉ N · OC, ^ oc ₉ h. 0 103-106 ° -cf ₂ -cfh ₂ -cf ₂ -chf ₂ -cf ₂ chf <3 CH N N 0C ₉ H, ch ₃ oc ₂ h ₉ i 1 oc ₉ h <C2H5 -cf ₂ -chfci 0 0 N Mp 147-148 'OC2H5O -cf ₂ -chfcl CH oc ₉ h. ° C2 ^H 5 oc ₄ h ₉ 0 -cf ₂ -chfci N ch ₃ 0 CF ~ -CHFBr N OC, Η ,. OCjH, 0 -CF ₂ -CHFBr CH 0C, H, oc ₂ h ₅ 0 -CFyCHFBr N ch; OCJL 0 CHF, ca . N ^CCl3 OCH3 4 9 CCK 0 137-145 ° N OCH ₃ 0 185-187 ° CF, -CCLF ~ N OCR, and ₃ 0 CHF, N C H <?; OCH, 0 114-116p -chf ₂ N c; H OC, H, 0 -chf ₂ N CH n-OC ₃ H ₂ 0 -chf ₉ N ch ₅ γι-OCAHq 0 153-154 ° ^C 2 ^F 5 N ch ₅ and ₃ 0 ^C 2 ^b 5 N cfl ₃ and ₃ 0 Op.145-149 ° C2 ^F 5 N ch ₃ ^OC 25 0 ^ 2 ^F 3 N OC, H, oc ₉ h ^ 0 ^C 2 ^F 5 CH CH ₃ ^CH 3 och ₂ och ₃ 0 173-175 ° ^C 2 ^F 5 c ₂ f ₅ CH CH ^c A CH ₃ 0 0 165-170 ° ^C 2 ^F 5 CH OCH, OCH, 0 Mp 192-193 ^C 2 ^F 5 N ch ₃ ³ ch ₃ 0 Mp 189-190o chf ₂ N cl cl 0 105-107 ° C with 1 mol of dioxane -CFyCHFBr N ^CH 3 n-OC ₂ H ₄ s -cf ₂ -cf ₂ ci -CF, -CBrF, chf ₂ N and ₃ and ₃ s N N och ₃ ca. och ₃ ca ₃ . s s chf ₂ N ^C 25 and ₃ s 146-147 ° chf ₂ N ^C 2 ^H 5 OCH, salt CHF, N ^C X OCH salt. ^C 2P ² CHF, ch ₂ N OCíL Ocre s ² N N OC, H, ch ₃ ocjL n-ÖC., H _Q s s 142-143 ° chf ₂ CH OC ₂ ^H 5 oc, it s chf ₂ N oc ₉ h. OCX salt chf ₂ CH OC ₂ ^H 5 oc ₉ h. salt chf ₂ N oc ₂ h ₅ oc ₂ h ₅ so ₂

-351

Continuation of Table 7

191 006

R ₄ X Physical Data

The number of compound A

ER ₃

947 chf ₂ CH oc ₂ h ₅ and ₅ so ₂ 948 cfh. N ch ₃ n-0C ₄ Hn so ₂ 949 cf ₃ N oc ₂ h ₅ ^OC 2 «5 s 950 cf ₃ CH oc ₂ h ₅ oc ₂ h ₅ s 951 CF, N ch, oc ₄ h s 952 -cf ₂ -chf ₂ Ν ' oc ₂ h ₅ oc ₂ h ₅ s 953 -CF -CHF CH a, h < 0¾ s 954 ^{-CF2 -CHF2} N ch. n íXLH, s 955 -cf ₂ -chfci N oc ₇ h. ^OC 2 «5 s 956 -CFyCHFCl CH a, h ' ^OC 2 ^H 5 s 957 -cf ₂ -chfci N ch ₃ n-O _{1 4} H ₉ s 958 -CFyCHFBr N och, ch, OCH, CH s 959 CF-CHFBr CH 0C ₂ fl ₅ oc ₂ rf ₅ s 960 ^C 2 ^F 5 CH CH the 0 961 X eZ ^C 2 ^F 5 N OCH, the 0 153-155 ° 962 ^ 2 ^F 5 CH ch ₃ F 0 963 ^C 2 ^F 5 N och, och, 0 185-187 ° 964 c, f. N and ₃ OC-H, 0 965 c ² f ^{5 v} 2 ^r 5 N ch ₂ q ocL ⁵ 0 966 ^C 2 ^F 5 H -Cri (CH ₃ ) ₂ OCH 0 967 ^C 2 ^F 5 N c ₂ h ₅ cl 0 968 969 CF ^l 2 5 ^C 2 ^F 5 N N -Ch ₂ and ₃ ch ₃ och, 0 0 970 C, Fr CH -CH, OCH and ₃ 0 971 c ² f ^{5 c} 2 ^ 5 N ocrf ₃ -OCH (CH ₂ ) ₂ 0 972 ^ 2 ^F 5 N OCH, SCH, 0 973 C ₂ ^F 5 N ch ₃ OCH ³ , s 974 ^C 2 ^F c CH ch, OCH, s 975 PF ⁵ N OCH, OCH, s 976 CF ₂ Br N ch ₃ OCH, s 178-179 ° 977 ^CF 2 ^Br N OCH, OCH, s 978 CF ₂ Br CH ch ₃ OCH, s 979 CF ₂ Br CH OCH, OCH, s 980 CF ₂ Br CH CH CH s 981 ^CF 2 ^Br N ^C A OCH, s 982 ^CF 2 ^Br N ch ₃ OCH, 0 983 CF ₂ Br N OCH, OCH, 0 984 CF ₂ Br N ^C 2 ^H 5 OCH, 0 985 ^CF 2 ^Br CH cft ₃ OCH, 0 986 CH ₂ Br CH OCH, OCH, 0 987 ^CF 3 CH CH ³ cl 0 988 C ^f 3 N and ₃ -OCH (CH,), 0 989 CF, N cl OCH, 0 990 CF, Ν ' c, h ₅ OCH, 0 991 992 CF, CF, N N -OH (CH ₃ ) ₂ • OCH (CH ₃ ) ₂ OCH, OCH, 0 0 993 -CH ₂ -CF, CH ch. the 0 994 CH - CF H OCH, the 0 995 cf ₂ ci CH -CH (CH) ₃ ) ₂ and ₃ 0 996 cf ₇ ci CH OCH, -SC H, 0

-361

Continuation of Table 7

191 006

Compound AE & ₃ R * X Physical Data Issue ____

997 cf ₂ ci N OCH, * ^SC 2 ^H 5 -SCH (CH,) ~ 0 998 cf ₂ ci N OCH, 0 999 cf ₂ ci 'N CC1, CH 0 1000 cf ₂ ci N CH, chf ₂ Br ³ 0 1001 cf ₂ ci N OCH, 0 1002 cf ₂ ci chf ₂ ch, Cf, CH 0 1003 cf ₂ ci N ³ 0 1004 cf ₂ ci N ch ₂ cf. OCH, 0 1005 ^CF 2 ^C1 N ch, cf, ch ₃ 0 1006 cf ₂ ci N oc ₂ h ₅ oc ₂ h ₅ 0 1007 CF ₂ á CH OC-H- oc ₂ h ₅ 0 1008 CF ₂ C1 N ^C 2 ^H 5 och. 0 1009 cf ₂ ci N C, H OC, H, 0 1010 ^cf 2Q N dl ⁵ ocA, ⁵ 0 1011 ^CF 2 ^a N CH OC, H, 0 1012 cf ₂ ci CH CH ^CH 3 0 1013 gf ₂ ci CH ch ₃ and ₃ 0 1014 cf ₂ ci N ch ₃ bi 0 1015 CF ₂ C1 N ^CH 3 Η 0 1016 cf ₂ ci CH cA ⁵ cl 0 1017 CF ₂ C1 CH the 0 1018 cf ₂ ci CH CH sch ₃ 0 1019 cf ₂ ci CH CH F 0 1020 CF ₂ C1 CH CH Br She 1021 ^CF 2 ^C1 CH ^C A S ⁵ uviiq 0 1022 cf ₂ ci CH cfC ⁵ 0 1023 cf ₂ ci CH ch ₃ 0 1024 cf ₂ ci CH CH2 ^a ch ₃ 0 1025 cf ₂ ci CH and ₃ 0 1028 cf ₂ ci CH sch ₃ 0 1029 cf ₂ ci CH and ₂ -OCH (CH,), 0 1030 cf ₂ ci CH ch ₂ f OCH, 0 1031 cf ₂ ci CH ch ₂ f CH ₃ and ₃ OCH (CH,), 0 1032 cf ₂ ci CH ch ₃ 0 1033 ^CF 2 ^Q N c ₂ ri ₅ 0 1034 cf ₂ ci N CÍHg C Hg cl 0 1035 cf ₂ ci N SCH, 0 1036 cf ₂ ci N ^C 2 ^H 5 CH 0 1037 1038 cf ₂ ci cf ₂ ci N N § & ₃ C ₂ H ₅ -och (ch ₃ ) ₂ 0 0 1039 cf ₂ ci N and ₃ och-ch ₃ -ch ₂ ch ₃ 0 1040 cf ₂ ci N ch ₃ -ch (ch ₃ ) ₂ -CHfCHX 0 1041 cf ₂ ci N. cl 0 1042 cf ₂ ci N -ch (ch ₃ ) ₂ OCH, 0 1043 cf ₂ ci N -ch (ch ₃ ) ₂ scfl ⁵ 0 1044 cf ₂ ci N -CH (CH,) ~ 0 1045 cf ₂ ci N ch ₂ ci CH ₃ 0 1046 CF ₂ C1 N ch.ci OCH, 0 1047 cf ₂ ci N CH ₂ F CH ₃ 0

-371

Continuation of Table 7

191 006

Compound A E Rj X Physical data.

number

1048 cf ₂ ci N ch ₂ f OCH, ο 1049 cf ₂ ci N ch ₂ f ocJt 0 1050 cf ₂ ci N -ch ₂ and ₃ ^C 2 «5 0 1051 CFjCl N -ch ₂ sch ₃ OCH, 0 1052 cf ₂ g N -ch ₂ sch ₃ ch ₃ 0 1053 cf ₂ g Ν ' ^- ch ₂ sch ₃ sch ₃ 0 1054 cf ₂ ci N -ch ₂ sch ₃ the She 1055 cf ₂ ci N -ch ₂ sch ₃ OC ₂ ^H 5 0 1056 cf ₂ g N scrf ₃ (3 0 1057 cf ₂ ci N sch ₃ and ₃ 0 1058 cf ₂ ci N sch ₃ ^QC 2 ^H 5 0 1059 1060 ^CF 2 ^C1 cf ₂ ci N N sch ₃ -OCH (CH ₂ ) ₂ ooi (ch ₃ ) ₂ Cl 0 0 1061 cf ₂ ci N CF, and ₃ 0 1062 CF ₂ C1 N CF, ch ₃ 0 1063 1064 CF ₂ C1 cf ₂ g N N cf ₃ CCl, OC ^ H, ocR ₃ 0 0 1065 ^c F ₂ C1 N CG, SCH, 0 1066 cf ₂ ci N CH cl 0 1067 CF ₂ ^C1 'N OCfi ₃ cl 0 1068 cf ₂ g N och, F 0 1070 cf ₂ ci N ch ₃ F 0 1071 cf ₂ ci CH och, OCH, s 1072 cf; ci N ch ₃ CH s 1073 cf ₂ ci N OCH-j OC-H- s 1074 ^CF 2 ^C1 CH -CH ₂ OCH, ocfl ₃ s 1075 ^CF 2 ^C1 N and ₃ and ₃ s 1076 cf ₂ g CH C ₂ H ₅ and ₃ s 1077 1078 C ^p 2 ^{C1 CF} 2 ^C1 N N address £ ⁵ ch ₃ och ₃ s salt 1079 cf ₂ ci N OCH, and ₃ salt 1080 cf ₂ ci CH CH and ₃ salt 1082 , CF ₂ C1 N ch ₃ OCH, salt. 1083 1084 CF, G CF ₂ C1 N N ch ₃ OCH, CH, och ₃ salt: salt: 1085 ^cf 2G CH CH OCH, salt: 1086 cf ₂ g CH ^CH 3 ch ₃ salt; 1087 ^cf 2G CH and ₃ and ₃ salt: 1088 -CF-CF N OCH, -OCH (CH ₃ ) ₂ 0 1089 • ^CF Í ^F 3 N cl -OCH (CH ^ U 0 1090 cf.ci N SCH, OCH ₃ s 1091 CF ₂ ^C1 N CF, OCH, s 1092 ^CF 2 ^C1 N cm the s 1093 cf ₂ ci N ocm cl s 1094 cf ₂ ci N c _? h. CH s 1095 cf ₂ ci N and ₃ -Odl (CH ₃ ) ₂ s 1096 cf ₂ ci N -CH (CH,), and ₃ s 1097 cf ₂ ci N CH ₂ Cl and ₃ s 1098 cf ₂ g N 2 F OCH, s 1099 cf ₂ ci CH cl s 1100 cf ₂ ci CH Cfl ₃ ⁵ the s

-381

Continuation of Table 7

191 006

The number of compound A E «3 ^R 4 X 1101 cf ₂ ci CH ch, F s 1102 cf ₂ ci CH och. cl s 1103 cf ₂ ci N OC, H, OC, H, s 1104 cf ₂ ci N c, fl ₅ OCR? s 1105 ^CF 2 ^a N cfl, ⁵ och, s 1106 cf ₂ ci N CH OC, H, s 1107 ^CF 2 ^a CH CH CH s 1108 CF ₂ C1 CH ^CH 3 och, s 1109 cf ₂ ci CH OCH, och. SHE 1109 cf ₂ ci CH OCH, OCH, 0 1110 cf ₂ q N ch ₃ ch ₃ 0 1111 CF Cl N and ₃ oc, h _s 0 1112 ^cf 2C1 CH OCH, oc ₂ h ₅ 0 1113 CF ₂ C1 CH -ch ₂ and ₃ and ₃ 0 1114 CF ₂ C1 N -CH, OCH och, 0 1115 of ₂ ci N och, och, 0 1116 cf ₂ ci N -ch ₂ -och ₃ ch. 0 1118 chf ₂ CH -ch (ch ₃ ) ₂ and ₃ s 1119 chf ₂ CH och. sc, rf ₅ s

Physical data

1120

1121

1122

1123

1124

1125

1126

1127

1128

1129

1130

1131

1132

1133

1134 135

1136

1137

1138

1139

1140

1141

1142

1143

1144

1145

1146 1147.

1148

1149

1150

1151

CHF, chf ₂ chf ₂ chf ₂ chf ₂ chf ₂ chf ₂ chf ₂

CHF2 chf ₂ chf ₂ ^CHF 2 chf ₂ ^CHF 2 ^CHF 2 chf ₂ cfh ₂ ^CHF 2

CHF, chf ₂ ^chf 2 ^CHF 2 chf ₂ chf ₂ chf ₂ ^CHF 2

CHF.

^CHF 2 chf ₂ chf ₂ chf ₂ chf ₂

N

N

N

N

N

N

N

N

N

N

N

N

N

N

N

OCH,

OCH,

CC1,

CH

CHF, chf ₂ -ch ₂ cf, -CH, CF, cr

CH

-CH ² -ock

-CHySCH,

-ch ₂ -sch,

-ch ₂ -sch, how-sch,

SOR ^SC 2 ^H 5 soi (ch,) ₂ ch ₃

Br

OCH,

CH

cl

OCH,

CH

CH, ch ₃

SCH, a

OC, H,

cl

N N N sch ₃ sch, sch ₃ OCH, oc ₂ h ₅ oCh (Ch ₃ ) ₂ S S S op N -OCH (CH ₃ ) ₂ cl S op N CF, OCH, S N CF, CH s N cf. a, h. s N ccr ₃ and ₃ s N CC1, SCH, s N CH the s w and ₃ cl s op N and ₃ F s N OCH, Br s N CH F s N CH Br s N CH H s CH ^C 2 5 cl s

Mp.162-163 ° Mp 159-161 °

Mp 147-149 °

151-153

-391

Continuation of Table 7

191 006

The number of compound A E ^R 3 ^R 4 X Physical data 1152 chf ₂ CH CH cl s 194-196 ° 1153 chf ₂ CH CH SCH, s 1154 ^CHF 2 CH CH I ³ s Mp. 186-187 ^p 1155 chf ₂ CH Cik Br s 1156 1157 chf ₂ CHF, CH CH C C ₂ ^H 5 sct £ ⁵ s s 1158 ^CHF 2 CH, CF CH s 1159 ^CHF 2 CH ² Cl @ Cl CIK s 1160 ^chf 2 CH CIKCl OCH, s 1161 ^chf 2 CH and ₃ cl s 159-165 ° 1162 ^CHF 2 CH and ₃ SCFL s 1164 chf ₂ CH OCH -OCIRCHJ, s 1165 chf ₂ CH ch ₂ f and ₃ s 1166 ^CHF 2 CH ch ₂ f ^CH 3 s 1167 1168 ^CHF 2 chf ₂ CH N och ₃ • och (ch,), s s 1169 ^CHF 2 N c H ₅ cl s Op.163-164 ° 1170 chf ₂ N c H sch ₃ s 1171 chf ₂ N c ₂ h CH s Mp 166-167 ° 1172 CHF, N C, H, (Jk s 1173 chf ₃ N and ₃ (X'HICH ₃ ) ₂ s Mp 120-122 ° 1174 ^chf 2 N ° ch ₃ -och-ch ₃ s 1175 chf ₂ N ch ₃ ch ₂ ch ₃ -Cl ^ CH,), s 169-170 ° 1176 CHF N -CH (CH ₃ ) ₂ cl s 1177 ^CHF 2 N -CH (CH ₃ ), OCH, s Mp 148-150 ° 1178 ^CHF 2 N -CH (CH,), OC, H, s 1179 ^CHF 2 N - (ClbCHX SCH, s 1180 ^chf 2 N ch ₂ ci ^CH 3 s 1181 ^CHF 2 N ch ₂ ci and ₃ s 1182 ^CHF 2 N ch ₂ f CH s 1183 chf ₂ N ch ₂ f OCH, s 1184 CHF, N ^CH 2 ^F OC, H, s 1185 ^chf 2 N -ch ₂ -och ₃ ^C Á s 1186 ^CHF 2 N -ch ₂ -sch ₃ OC; s 1187 ^CHF 2 CH -CHfCH ₃ ) ₂ OCH, 0 141-143 ° 1188 chf ₂ CH and ₃ SC, H _s 0 1189 CHF, N ^0CH 3 ^SC 2 ^H 5 SHE 1190 chf ₂ N and ₃ -SCT1 (CH,), 0 1191 chf ₂ N cci, ^CH 3 0 1192 chf ₂ N ch ₃ Br 0 1193 chf ₂ N CHF? and ₃ 0 1194 chf ₂ N ^CHF 2 CH ³ 0 1195 chf ₂ N. CH, CF, cl 0 1196 CHF, N CH, CF, OCH, 0 1197 chf ₂ N -ch ₂ -cf ₃ CH 0 1198 C » ^F 2 N CH, 0CH ch ₃ 0 1199 chf ₂ N CH on 0 1200 chf ₂ N ^CH 3 H 0 1201 chf ₂ CH c rt cl 0 158-159 ° 1202 chf ₂ CH c ₃ ⁵ cl 0 190-191 ° 40

-401

Continuation of Table T.

191 006

The number of compound A E ^R 3 ^R 4 X Physical data 1203 chf ₂ CH CH sch ₃ 0 Mp 171-172 ° 1204 ^CHF 2 CH ch ₃ F 0 174-176 ° 1205 CHF ^ CH ^CH 3 Br 0 1206 chf ₂ CH C, H, SC ^ ^H 5 0 1207 ^CHF 2 CH C., H ₅ 0 1208 ^CHF 2 CH CH 0 1207 ^CHF 2 CH CH, C1 CH 0 1210 1211 CHF-chf ₂ CH CH CH ₂ C1 OCH, OCH, C1 0 0 Mp 167-168 ° Mp 165-167 ° 1212 ^CHF 2 CH cl cl 0 Mp 183-188 ° 1213 ^CHF 2 CH and ₃ sch ₃ -OCHÍCH ^ 0 1214 chf ₂ CH OCH, 0 72-74 ° 1215 CHF CH CH, M OCH- 0 175-176 ° 1216 CHF, CH F-CH ch ₃ och ₃ -OCHÍCH ^ 0 1217 1218 CHF, chp ₂ CH N ^CH 3 c ₂ fi ₅ 0 0 152-154 ° 1219 ^CHF 2 N ^C 2 ^H c cl 0 135-137 ° 1220 CHF, N ^C 2 ^H 5 SCH 0 1221 chf, N c ₂ h CH, ³ 0 136-138 ° 1222 CHF, . N C-H C, H 0 1223 chf ₂ N since -QCH (CH ₃ ) ₂ 0 113-115 ° 1224 chf ₂ N and ₃ -och-ch ₃ ch, ch ₃ -CHttH-k 0 1225 CHF, chf ² N ch ₃ 0 Op.137-140 ° 1226 N -CHÍCH-jk cl 0 Op.160-162 ° 1227 chf ₂ N -CHfCH's OCH ₃ 0 M.p. 75-78 ° 1228 chf ₂ N -ch (ch ₃ ) ₂ oc-ri ₅ 0 1229 chf ₂ N -CH (CH -) - SCH 0 1230 chf ₂ N ch ₂ ci CH ₃ 0 113-115 ° 1231 CHF, N ch ₂ ci c> ch ₃ 0 94-96 ° 1232 ^CHF 2 N ch, f CH, ° ch ₃ 0 1233 CHF, N CH, M She 1234 CHF, N CH, F -ch, och ₃ OC, H 0 1235 CHF, N 0 1236 chf ₂ N -ch, sch ₃ 0 1239 CHF, N -cf, sch ₃ -ch, sch, scil cl 0 1240 CHF, N OC-H- 0 1241 chf ₂ N cl 0 Op.147-149 ° 1242 CHF, N sch ₃ OCH ₃ 0 Op.161-162 ° 1243 CHF, N sch ₃ a, h -OdH (0H-k 0 1244 chf ₂ N sch ₃ s 163-164 ° 1245 CHF, N -0CH (CH,), cl 0 103-104 ° 1246 CHF, N cf ₃ OCH- 0 87-90 ° 1247 chf. N cf ₃ ^CH3 ^ 0 1248 CHF, N ^CF 3 C-H 0 1249 chf ₂ N ccr ₃ ocir ₃ 0 142-146 ° 1250 chf. N CC1, sch. 0 1251 chf. N ch ₃ och ₃ Cl ³ 0 160-161 ° .1252 chf ₂ N cl 0 167-168 ° 1253 chf ₂ N and ₃ F 0 1254 CH ^f 2 N and ₃ Br 0

-411

7. Continue Table

191 006

The compound number ! t A E ^R 3 ^R 4 X 1255 chf ₂ N CH F . 0 1256 ch ₂ f N ch ₃ OCH, and ₃ 0 1257 ch ₂ f N OCH, 0 1258 ch ₂ f N ch ₃ ^CH 3 and ₃ 0 1259 ch f ~ N 0 1260 ch ₂ f CH and ₃ s 1261 1262 ch ₂ f ^CH 2 ^F CH CH OCH, ch ₃ och ₃ s s 1263 C ^H 2 ^F . N CH ₃ 0 1264 ch ₂ f CH ch ₃ och ₃ and ₃ 0 1265 ^CH 2 ^F CH and ₃ 0 1266 CH.F N OCH, 0 1267 ch ₂ f -CFl-CF-Br N ch ₃ 0 1268 N CH and ₃ 0 1269 • On CFyCF ^ CH CH and ₃ 0 1270 -cf ₂ -cf ₂ ci -ClU-CHF N CH OCH, s 1272 N CH OCH, 0 1273 -ch ₂ -ch ₂ f N CH3 CH ³ 0 1274 -ch ₂ -ch ₂ f N OCH, ocíL 0 1275 1277 -ch ₂ -ch ₂ -f. -CH ₂ -CH ₂ F CH CH ch ₃ OCH, och ₃ OCH, 0 0 1278 -ch ~ -ch ₂ f CH CH CH ₃ and ₃ 0 1279 -ch ₂ -ch ₂ f N ^CH 3 s 1280 -ch ₂ -ch ₂ f -CH ₂ -CClt N OCH, and ₃ s 1281 N CH OCH, and ₃ 0 1282 -CHyCCl, N OCR, 0 1283 -ch ₂ -cci ₃ CH CR, och ₃ ^0CH 3 0 1284 -ch ₂ -cci ₃ CH and ₃ 0 1285 1286 -ch ₂ -cci ₃ -cf ₂ -ch ₃ N N C ~ H, obi. och ₃ ^0CH 3 0 0 1287 -CFyCH, N CH OCH, 0 1288 -cf ₂ -ch ₃ N CH CR, och. 0 1289 -cf ₂ -ch, CH ch ₃ OCH, ch ₃ och ₃ 0 1290 1291 1292 -CF.-C1L -CirCHLC1 -CH _? -CH _? C1 CH N N OCH, och ₃ och ₃ 0 s s 1293 -CH ₂ -CH ₂ C1 N ^C 2 ^H 5 and ₃ s 1294 -ch ₂ -ch ₂ ci N CH OC, H, s 1295 1296 -ch ₂ -ch ₂ ci -CU _V C1LC1 CH N $ OCIL ⁵ 0C ₂ H, s 0 1297 -ch ₂ -ch ₂ ci N CH ₃ □ C ~ H < s 1298 -ch ₂ -ch Cl CH OCH, ocá, ⁵ s 1299 -CH ₂ -CH ₂ Cl CH CH OCH, s 1300 -ch ₂ -ch ₂ ci N CF, OCH, 0 1301 -CH ₂ -CH -Cl CH ch ₂ f OCH, 0 1302 . -CH ₂ -CH ₂ C1 CH ch ₂ ch, ocfi ₃ ³ She 1303 -ch ₂ -ch, ci CH cl She 1304 -CH ₂ -CH ₂ C1 CH _<H2 -och ₃ OCH 3 0 1305 '1306 -CH ₂ CH ₂ CV -Clt-ClÉCl -CH ₂ -CH ₂ Cl N N -CH, -OCH, ^CH 3 OCH, OCR, 0 0 1307 N and ₃ OCR, 0

Physical data.

Mp 186-187 °

154-155 °

136-138 °

Mp 174-175 ° Mp 166-168 °

-421

Continuation of Table 7

191 006

Compound A is the E number

R ₄ X Physical Data - .... ..... 1 IM ----- T ~

1308 ch ₂ -ch ₂ ci N ch, CH OCH, 0 169-171 ° 1309 -ch ₂ -ch ₂ ci N c ₂ h ₅ 0 164-165 ° 1310 -ch ₂ -ch ₂ ci N dl ⁵ CH 0 169-170 ° 1311 -ch ₂ -ch ₂ ci N σ ³ 0 1312 -ch ₂ -ch ₂ ci N CH ₂ C1 OCH, and ₃ 0 1313 -CH ₂ -CH ₂ C1 -CH ₂ -CH ₂ -Cl N -OCH (CH,) ₉ sch ₃ and ₃ 0 1314 N OCH, 0 1315 -CH ₂ -CH ₂ C1 N -CH (CH,) ~ 0 1316 -CH ₂ -CH ₂ Cl -CH ₂ -CH ₂ a -CH, -CH ₂ Cl 'N 0C, H, and ₃ 0 151-152 ° 1317 N Oca OC, H, 0 1318 N OCH, Cl ² 0 1319 -ch ₂ -ch ₂ ci CH CH ' OCH, OCH, 0 1320 -CH ₂ -CH ₂ C1 CH OCH, 0 Mp 184-186 ° 1321 -CH ₂ -CH ₂ C1 CH CH CH 0 Mp 181-183 ° 1322 -CH ₂ -CH ₂ C1 CH CH Cl ³ 0 1323 -ch ₂ -ch ₂ ci CH CH F 0 1324 -CH ₂ -CH ₂ -CH ₂ C1 ₂ C1 -CHC1CH CH c ₂ fl and ₃ 0 1325 N ⁵ och. 0 117-118 ° 1326 -CH ₂ -CHCl-CH ₂ C1 N and ₃ OCH, 0 106-110 ° 1327 -ch ₂ -chci-ch ₂ ci N CH CH 0 1328 -CH ₂ -CHCl-CH ₂ C1 N ^C 2 »5 och, och. 0 1329 -CH ₂ -CHCl-CH ₂ Cl CH cn 0 1330 -CH ₂ -CHCl-CH ₂ C1 CH OCH, OCH, 0 170-173 ° 1331 -CH ₂ -CHCl-CH ₂ Cl CH CH CH 0 1332 -CH ₂ -CHCl-CH ₂ Cl N CH och, s 1333 -CH ₂ -CHCl-CH ₂ Cl N and ₃ och. s 1334 3335 -CH ₂ -CHCl-CH ₂ C1 CH OCH, OCH. s 1336 -CH ₂ -CHCl-CH ₂ C1 N OCH, CL 0 1338 CHN-CHCl-CHCl CH CH CL 0 1339 ^ch 2F N ch ₃ ^OC 2 ^H 5 0 1340 ^CH 2 ^F CH CH ci ² 0 1341 ^CH 2 ^F -CH ₂ -CHCl 1 -CH ₂ Cl N and ₃ cl 0 1342 CH ^C 2 ^H 5 cl 0 1343 -CHÍCHBr-ClKBr -CIL-CHCl-CHCl N CB, OCH, 0 Mp 183-184 ° 1344 N CH3 och. 0 106-108 ° 1345 ^CH 3 -Clk-CHCl-CHCl N and ₃ and ₃ 0 1346 CH, -ch ₂ -chci-chci N ch ₃ CH 0 1347 CH -CH, -CHC1-CHC1 CH CH OCH, 0 1348 CH -Cyclohexyl-CHCl-CHCl CH ch ₃ cl 0 1349 ch ₃ -CH _r CHCl-CHCl CH and ₃ OCH, 0 1350 CH, -ch ₂ -chcichci N ^ 2 ^ 5 OCH, 0 1351 < ^h 3 cf ₂ -chf ₂ N c ₂ h ₅ and ₃ 0 158) 160 °

Continuation of Table -432 λ

191 006

Number of compound A E ^R 3 ^R 4 X Physical data 1352 -cf ₂ -chf ₂ CH CH? OCH, cl 0 1353 -cf ₂ -chf ₂ -cf ₂ -chfci -CF ₂ -CHFa CH cl 0 164-165 ° 1355 CH CH OCH, the 0 177-179 ° 1356 CH cl 0 164-165 ° 1357 -cf ₂ -chfci N -ch (ch ₃ ) ₂ and ₃ 0 Mp 128-130 °

-LIáblázaL

Compounds of formula 0a

The number of the chemical A let X-A state rj ^R 3 ^R 4 X E 1401 chf ₂ ........ 2 5-F Title ⁵ and ₃ OC ^ 0 N 1402 chf ₂ 2 5-F the 0 CH 1403 chf ₂ 2 5-F sch ₃ -OCH (CH 2), 0 N 1404 CHF 2 5-F OCH, 0 N 1405 chf ₂ 2 5-F OCH, the 0 N 1406 chf ₂ 2 5-F C & ⁵ OCH 3 s N 1407 chf ₂ 2 5-F the s N 1408 chf ₂ 2 5-F CH the s CH 1409 chf ₂ 2 5-F ^C 2 ”5 CH 0 N 1410 chf ₂ - 2 5-F CH 0 CH 1411 chf ₂ 2 5-F ³ 0 CH 1412 chf ₂ 2 5-F 0C ₂ H _s the 0 N 1413 chf ₂ 2 5-F CH3 F 0 N 1414 chf ₂ 2 5-F CH Br 0 N 1415 chf ₂ 2 5-F CH Br 0 CH 1416 chf ₂ 2 5-F CH F 0 CH 1417 chf ₂ 2 5-F ' $ the 0 CH 1418 CHF 2 5-F OCH ₃ 0 N 1419 ^C 2 ^F 5 2 5-F CH and ₃ 0 N 1420 ^ 2 ^F 5 CIF, 2 5-F CH OCH, 0 N 1421 2 5-F ch ₃ OCH, OCH ₃ 0 CH 1422 2 5-F OCH, 0 CH 1423 ^C 2 ^F 5 2 5-F CH the 0 CH 1424 c! ^F 5 2 6-F ch ₃ and ₃ 0 N 1425 C? F < 2 6-F CH and ₃ 0 CH 1426 ^ 2 ^F 5 2 6-F CU7 and ₃ 0 • N 1427 2 6-F and ₃ s N 1428 ^ 2 ^F 5 2 6-F CH OCH? s CH 1429 ^ 2 ^F 5 2 6-F $ OCH, och? s N 1430 1431 ² c ⁵ ^ 2 ^F 5 2 2 6-COOCH ₃ 6-COOCH, OCH, OCH, 0 0 NN N 1432 ^ 2 ^F 5 2 6-COOCH ₃ CH och. 0 CH 1433 1434 -¾ 2 2 6-F 6-F C ^ He cC ⁵ OCH3 OCH, OCH, 0 0 N N 1435 chf ₂ 2 6-F the 0 CH 1437 chf ₂ í 6-F -OCH (CH ₃ ) ₂ 0 N 1438 chf ₂ 2 6-F and ₃ the 0 N

Physical data

140-141 °

160-161 °

-441

Continuation of Table 8

191 006

The number of the chemical-A let _

CHF 1439,

1440 CHF ₂

1441 CHF ₂

1442 CHF ₂

1443 CHF ₂

1444 CHF ₂

1445 CHF ₂ 1445 CHF ₂

1447 CHF ₂

1448. CHF ₂ 1449 CHF ₂

1450 CHF ₂

1451 CHF ₂

1452 CHF ₂

1453 CHF ₂

1454 CHF ₂

1455 CHF ₂

1456 CHF ₂

1457 CHF ₂

1458 CHF ₂

1459 CHF ₂

1460 CHF ₂

1461 CHF ₂

1462 CHF ₂

1463 CHF ₂

1464 CHF ₂

X-A state ^R 1 ^R 3 ^R 4 X E Physical data 2 6-F -CH (CHA, OCH, 0 N 2 6-F ^C 2 ^H 5 OCH, 0 CH 2 6-F the 0 CH 2 6-F SCH, 0 N 2 6-F OCH, SCH, 0 N 2 - * 6-F -OCH (CH ₃ ) ₂ a 0 N 2 6-F C, H, CH 0 N 2 2 6-F 6-F -ch (ch,) ₂ ch ₂ f ^C 2 «5 CH OCH, 0 0 N N 4 6-F OCH, s N 2 6-F the s CH 2 6-F ch, OCH, Br s CH 2 6-F the s CH 2 2 6-F 5-F C ₂ H ³ ocrij CH OCH, s She CH N Mp 150-151 ° 2 6-Q OCH, OCH, 0 N 162-165 ° 2 6-C1 OCH, OCH, 0 CH Mp 148-1 S4 ° 2 6-a CH OCH, CH OCH, 0 CH Mp 189-191 ° 2 5-Cl 0 N 164-166 ° 4 2-CH CH OCH, 0 N 147-150 ° 2 5-Cl OCH, 0 N 130-132 ° 2 5-Cl OCH, 0 N 149-151 ° 2 5-Cl CH the 0 CH Mp 182 ° l (dec) Mp 170-172 ° Mp 128-135 ° 2 2 5-Cl 5-Cl och, a -OCH (CH,) ₂ OCH, 0 0 CH N 2 5-Cl OCH, SCH, 0 CH

-451

191 006

Table 9 Compounds of formula 1c

A ve- compound number THE -X-A state ^R 1 ^R 2 X E Physical data 1S01 CFH, 3 6-NO 3-Br s N 1502 ^CF 3 3 6 C00C H < 3-Br 0 N 1503 cf ₃ 3 '6-COOC, H. 3-Br s N 1504 ^CF 3 3 O-CH 2-a salt, CH 1505 chf ₂ 3 6-CH ₃ 2-a SO ₂ CH 1506 ^CHF 2 3 2-NO ₂ 2-a 0 N 1507 chf ₂ 3 2-NO ₂ 2-a 0 CH 1508 chf ₂ 3 C00C 2 H, 2-a 0 N 1509 ^CHF 2 3 2 COOC H < 2-a s N 1510 CHF, 3 6-C1 2-a 0 CH 1511 chf ₂ 3 6-C1 2-a s CH 1512 chf ₂ 3 6-C1 2-a salt N 1513 CHF, . 3 6-C1 2-a salt, N 1514 chf ₂ 3 2-CF 2-a 0 ² N 1515 CHF, 3 5-NO ₂ 2-a 0 N 170-172 ° 1516 chf ₂ 3 6-OCH ₃ 2-a 0 CH 1517 chf ₂ 3 6-OCH 2-a 0 N 1518 ^CHF 2 3 6-SCH? 2-a 0 CH 1519 chf ₂ 3 6-SCH ₃ 2-a 0 N 1520 CHF, 3 2-SO ₂ CH ₃ 2-a 0 CH 1521 chf ₂ 3 2-SO ₂ CH ₃ 2-a 0 N ...........- Table 10 Compounds of formula (Id) . ..

A physical-AXM -XA RJ R ₄ Physical data frigate position number.

1601 1602 1603 ^CHF CHF CHF ₂ 2 ₂ 0 s 0 2 2 2 2.5 2.5 2.6 N N N CH CH CH och, och- och ₃ 1604 chf ₂ 0 2 2.5 CH CH och, 1605 chf ₂ 0 2 2.5 CH ³ CH / 1606 chf ₂ 0 2 2.5 CH the och. 1607 chf ₂ 0 2 2.5 N C, H, OC ^h 3 1608 chf ₂ 0 2 2.5 N £ 0Cf och. 1609 • cp ₂ .cfh 0 2 2.5 N CH and ₃ 1610 cf ₃ 0 2 2.5 N CH3 and ₃

-461

191 006

Table 11 Compounds of Formula Ia ^R 3 ^R 4 ^X

Physical data

The compound is the number of E

1701 "ΤΓ 1702 chf ₂ CH 1703 chf ₂ N 1704 chf ₂ N 1705 ^CHF 2 N 1706 chf ₂ CH 1707 chf ₂ N 1708 CHF, ^C 2 ^F < N 1709 N 1710 ^C 2 ^F 5 N 1711 CF ,, jCHF N 1712 cf ₂ chf ₃ N

-CH (CH 1) ^C 2 ^H 5 ^C 2 ^H 5

3'2

Ch (ch ₃ ) ₂

CFK

CH?

-dcá (CH)

3 ⁷ 2

He, (7

OCH, O

-OCH (CH ₃ ) ₂ O och ₃ 0 och ₃ s och ₃ s

-OCH (CH ₃ ) ₂ S och ₃ s och ₃ o

OCH ₃ s och ₃ o och ₃ 0

Table 12 Compounds of formula (lf)

Compound A number E ^R 3 ^R 4 X z Physical data 1801 chf ₂ N CH OCH, 0 0 132-134 ° 1802 chf ₂ N CH OC, fL 0 0 Mp. 121 ° C 122 _r 1803 chf ₂ CH CH ch ₃ SHE 0 199-201 ° 1804 CHF CH ch ₃ OCH, 0 0 Mp 189-191 ° 1805 chf ₂ CH 0CFL O ^ 0 0 152-154 ° 1806 chf ₂ N ch ₃ and ₃ SHE s Mp 148-150 ° 1807 chf ₂ N ch, ch ₃ S 0 Mp 148-159 ° 1808 CHF, N CH OCH, S 0 169-172 ° 1809 chf ₂ N CH oc ₂ r. s 0 154-155 ° 1810 chfÍ N CH OCH, s s 1811 ^CHF 2 CH CH CH s 0 176-178 ° 1812 CHF, CH ch ₃ and ₃ s 0 172-174 ° 1913 chf ₂ CH OCH, OCH, s 0 155-162 ° 1814 chf ₇ N CH ch ₃ SHE 0 1815 cf ₃ N CH and ₂ salt 0 1816 cf ₃ CH ^C H3 and ₃ salt 0 1817 cf ₃ N CH and ₃ so ₂ 0 1818 cf ₃ CH CH and ₃ so ₂ 0 1819 chf ₂ N CH OCH, salt 0 165-167 ° 1820 chf ₂ N CH ^CH 3 salt 0 1821 chf ₂ N ch ₃ ^OC 2 ^H 5 salt 0 156-158 ° 1822 chf ₂ CH CH ch ₃ salt 0 1823 chf ₂ CH ch ₃ and ₃ salt 0 195-197 ° 1824 chf ₂ CH OCH, and ₃ salt 0 1825 ^CHF 2 N CH OCH, salt s 1826 chf ₂ N ch. ^CH 3 so ₂ 0 1827 chf ₂ N ch ₃ OCH, so ₇ 0 1828 chf ₂ N ch ₃ OC, H, so ₂ 0 1829 chf ₂ N ch ₃ and ₃ so ₂ s

-471

Continuation of Table 12

191 006

Compound A number E ^R 3 ^R 4 X z Physical data 1830 chf ₂ CH CH CH OCH, eat ₂ . SHE 1831 chf ₂ CH CH OCH, so ₂ 0 1832 CHF, CH OCH, salt, 0 1833 CF, N CH OCH, 0 ² 0 160-162 ° 1834 ^CF 3 N CH CH 0 0 1835 CF, N CH OC, H, 0 0 1836 CF, CH CH CH OCH, OCH, 0 0 1837 1838 cf, ^CF 3 CH CH CH OCH, 0 0 0 0 Opr148-152 ° 1839 ^CF 3 N CH OCH, 0 s 1840 CF, N CH CH OCH, s 0 1841 (¾ N CH s 0 1842 N CH oc ₂ fl ₅ s 0 1843 cf ₃ N CH OCH, s s 1844 CF, CH CH CH OCH, s 0 1845 CF, CH CH OCH, s 0 1846 CF, CH OCH, s 0 1847 CF, CHF, N CH OCH, 0 0 170-174 ° 1848 -cf ₂ -chf ₂ N CH CH 0 0 1849 -cf, -chf ₉ N CH OC, H, 0 0 136-140 ° 1850 -CFyCHF, CH CH CH OCH, OCH, 0 0 1851 1852 -cf ₂ -chf -CFyCHR CH CH CH OCH, 0 0 0 0 178-180 ° 1853 -cf ₂ -chf. N CH OCH, 0 s 1854 -cf ₂ -chf ₂ N CH CH OCH, s 0 1855 CR-CHF, N CH - s 0 156-158 ° 1856 -CFyCHF, N CH OC, H, < OCH, s 0 1857 CF, CHF, N CH s s 1858 -cf ₂ -chi- CH CH CH OCH, s 0 1859 -cf ₂ -chf ₂ CH CH OCH, s 0 1860 cf ₂ -chf ₂ CH OCH, s 0 1861 -CF 1 -CHClp -cf ₂ -chcif N CH OCH, 0 0 Mp 148-150 ° 1862 N CH CH3 0 0 1863 -CF ₂ -CHC1F N CH OC, H, 0 0 1864 -cf ₂ -chcif CH CH ch] 0 0 178-180 ° 1865 -cf ₂ -chcif CH CH OCH, OCH, 0 0 1866 -cf ₂ -chcif CH OCH, 0 0 1887 -cf ₂ -cfcif N CH OCH, 0 s 1868 -CF ₂ -CFC1F N CH CH OCH, s 0 1869 -CFj-CFCIF N CH s 0 1870 cf ₂ -chcif N CH OC-H, OCH, s 0 1871 • cf ₂ -chcif N CH s s 1872 -cf ₂ -chcif CH CH CH OCH, s 0 1873 -cf ₂ -chcif CH CH OCH, s 0 1874 -CF ₂ -CHC1F CH OCH, s 0 1875 -CFyCHBrF N CH OCH, 0 0 1876 CFyCHBrF N CH CH 0 0 1877 -CFyCHBrF N CH oc ₂ h _s 0 0 1878 -CFyCHBrF CH CH CH OCH, 0 0 1879 -CF ₂ -CHBrF CH CH OCH, 0 0 1880 -CF ₂ -CHBrF CH OCH 0 0

-481

12. Continue Table

191 006

The number of compound A - ^R 3 ^R 4 X z Physical data 1881 -CF.-CHBrF N CH OCH? 0 s 1882 -CF ₂ -CHBrF N CH ch ₃ s 0 1883 -CFyCHBrF N CH och, s 0 1884 -CF.-CHBrF N ch. oc ₇ fL s 0 1885 -CFÍ-CHBrF N ch. OCH, s s 1886 -CFyCHBrF CH ch. CH s 0 1887 -CF ^ -CHBrF CH ch. and ₃ s 0 1888 CF'-CHBrF CH OCH and ₃ s 0 1889 chf ₂ N OCH ³ OCH, 0 0 135-137 ° 1890 CHF, N OCH, och. s 0 Mp 145-147 ° 1891 CHF ¹ N OCH, and ₃ salt 0 1892 CHF N OCH, OCH, salt, 0 1893 <* 3 N and ₃ and ₃ 0 ² 0 174 ° (dec.) 1894 ^CF J N and ₃ OCH s 0 1895 -CF _? -CHF _? N OCH, och. 0 0 Op.179-181 ° 1896 -cf ₂ -chf N and ₃ och. s 0 1897 CF.CC1F, N and ₃ och. 0 0 1898 chf ₂ N and ₃ oc ₂ h. 0 0 114-116 ° 1899 chf ₂ N ch ₃ ocn ₃ 0 0 132-134 ° 1900 chf ₂ N OCÍk OCH, 0 0 135-137 ° 1901 chf ₂ N ch ₃ och. s 0 Op.169-172 °

Compounds of formula (Ig)

Number of compound THE E ^R 2 ^R 1 X Physical constants 2001 chf ₂ N CH H 0 2002 ch ₂ N Cl ³ H 0 2003 cf, N G H 0 2004 crirj N H H 0 153-154 ° 2005 chf ₂ CH H H 0 2006 ' chf ₂ N F H 0 2007 chf ₂ CH F H 0 Table 14 Ve igyületek The compound THE E ^R 1 ^R 2 X Physical constants number 2101 chf ₂ N H G 0 154-157 ° 2102 chf ₂ CH H G 0 Mp 168-170 ° 2103 chf ₂ CH H G s 2104 CHF. N H G s 2105 -CF.-CHCIF N cl H 0 2106 CF, N G H 0 2107 chf ₂ N cl H s 2108 chf ₂ N H F 0

-492

Continuation of Table 14

191 006

Number of compound THE E ^R 1 ^R 2 X Physical constants 2109 ^CHF 2 CH Η F. She 2110 chf ₂ N F H 0 116-118 ° 2111 chf ₂ CH F H 0 152-154 ° 2112 chf ₉ CH cl H 0 2113 chf ₂ N cl H 0 Op.139-140 ° 2114 chf ₉ CH CH? H 0 2115 chf ₂ N CH? H 0 2116 chf ₂ CH Br ³ H 0 2117 chf ₂ N Br H 0

Example 13

Examples of Formulations of Liquid Active Ingredients of Formula I (% by Weight)

the) 20% b) 10% c) 50% 5% 4% 5.8% 5% 4% - 30% 20% 40% 62% 93%

active ingredient Ca-dodecylbenzenesulfonate castor oil poly (ethylene glycol) ether (36 mol AeO) cyclohexanone. xflolelegy

Such concentrates can be diluted with water to form any desired emulsion, b) Solutions

a) Wettable

the) b) c) agent 20% 60% 0.5% Na lignlnszulfonát 5% 5% 5% Na lauryl sulfate 3% - - Na-dizobutil naftalln- sulfonate - 6% 6%

octyl- fenfl-pollen-ethylene-glycol

ether (7-8 moles ethylene) oxy - 2% 2% highly dispersed silica 5% 27% 27% kaolin 61% - - NaCI - - 59.5 '

the) b) c) d) active ingredient 20% 10% 5% 1% ethylene glycol monomethyl ether 30% 50% 50% polietiléngllkol- molecular weight 400 70% 20% N-methyl-2-pyrrolidone 50% 20% 44% 28% epoxidized coconut oil - 1% 1% Solutions for use very small drops · c) Granules agent the) 5% b) 10% kaolin 94% - highly dispersed silica 1% - attapulgite - 90%

The active ingredient is dissolved in methylene chloride, sprayed onto the vehicle and the solvent is then removed in vacuo.

d) Dusting agents active substance high dispersion silica talc kaolin

a) b)

0.1% 1% 1% 5% 98.9% - - 94%

The lubricants are thoroughly mixed with the active ingredient to give a ready-to-use powder.

Example 14 Examples of formulations containing the solid active ingredient of formula (I) (% =% w / w)

The active ingredient is mixed well with the additives and ground in a suitable mill. In this way, a spray powder is obtained which can be diluted with water to a suspension of any desired concentration.

b) Emulsifiable concentrate the) b) agent fenlT polletlléngllkol-octyl ether 10% 1% (4-5 moles ethylene oxide) 3% 3% Ca dodecllbenzolszulfonát 3% 3% castor oil pollgllkoléter (36 moles ethylene oxide) 4% 4% cyclohexanone 30% 10% xflolelegy 50% 79%

From this concentrate, any emulsion of the desired concentration can be prepared by diluting with water,

a) b) 0.1% 1% talc 99.9% kaolin 99%

The active ingredient is mixed with the lubricant and ground in a suitable mill to provide a ready-to-use powder.

d) Extrider granules

the)

10%

2%

1%

87%

b)

1%

2%

1%

96% active ingredient Na-IIgln-sulfonate carboxyl methylcellulose kaolin - -

The active ingredient is mixed with the additive,

Grind and moisten with water. This mixture is extruded and subsequently dried in a stream of air.

-501

191 006

(e) Embedded granules 2- -3 very strong effect, active ingredient 3% 4-6 medium effects, poll (ethylene glycol) 3% s 7 -8 low impact, i missed 94% 9 ineffective (as untreated control). The finely ground active ingredient is mixed with polyethylen airborne kaolin evenly Pre-emergence effect applied. This way dust-free embedded granules - we get a vision. The compound is Avena Setaria Slnapis StellarU (f) Suspended concentrate lu "Number .. - a) b) l 4 4 2 -i- active ingredient 40% 5% 2 4 4 2 2 ethylene glycol 10% 10% 75 5 6 2 2 nonyl phenyl polyethylene glycol Otero 76 4 4, 2 2 (15 moles ethylene oxide) 6% 1% 15 77 5 6 2 2 Na-IgGsulphonate 10% 5% 77 5 6 2 2 carboxymethylcellulose 1% 1% 81 3 l 2 2 37% aqueous formaldehyde solution 0.2% 0.2% 83 6 6 2 2 silicone oil 75% aqueous emulsion 90 2 2 2 2 in the form of 0.8 0.8 91 2 2 2 2 water 32% 77% 20 102 6 7 2 2 Finely ground active ingredient with additives I3l 2 3 2 2 mix well together, Dy way so 132 2 3 2 2 pendent concentrate, of which water 195 6 4 2 2 any suspension of the desired concentration can be prepared. 196 4 3 2 2 (The percentages are by weight), 200 6 5 2 2 (g) Saline solution 26 301 6 7 2 2 active ingredient 5% 302 5 4 2 2 Isopropylamine octylphenyl poly 303 5 6 2 2 ethylene glycol ether 312 6 5 2 2 (78 mol ethylene oxide) 3% 316 4 2 2 2 water 91% - 1Λ 329 3 2 2 2 (h) Wettable powder OU 331 4 4 2 2 95% N- [2- (methoxy-ethoxy) -phenylsulfonyl] -N-4-methyl- 333 6 5 2 / 2 toxl-6-methyl-1,3,5-triazine-2-yl) urea 337 2 2 2 2 3% aromatic sulfonic and sulfonic acid-formaldehyde con- 470 2 2 2 2 a mixture of the densate ammonium salts 471 l l 2 2 1% sodium alkyl sulfate 35 479 4 l 2 2 1% Urea Formaldehyde Polymerizate 500 6 3 2 2 522 4 2 2 2 Biological examples 524 3 4 2 2 The biological experiments, that is, the plants, respectively 526 3 2 2 2 treatment of seeds with such dilute aqueous suspensions 527 2 ' 2 2 2 were performed as described in Example 14 in 1% w / w 40 528 3 2 2 2 and 59% by weight of sodium chloride (further 532 5 5 2 3 other additives according to variant c) of the said example; 541 6 3 2 2 suitable wettable powder 551 2 3 2 2 prepared by dilution. 557 8 6 2 2 The active ingredient and the concentrate 587 4 3 2 2 is shown in the examples and in Tables. 45 595 2 2 í 2 THE 9 _ -J ... -1 ,, Example 15 901 2 l 2 1 Demonstration of pre-emergence herbicidal activity 902 6 4 2 2 In a greenhouse, plant seeds 12-15 cm 919 2 l  2 1 diameter flower pots. Immediately thereafter the soil SALT ll6l 6 3 2 2 surface with an aqueous dispersion of the active ingredient or a solution 1202 4 l 2 2 treatment. You have a dispersion of such concentration 1203 3 l 2 2 solution is used to apply per hectare 1212 7 3 2 2 amount of active ingredient 4 kg Ticket. The pots 1223 3 2 2 2 then in the greenhouse 22-25 ° κ> η 50-70% 1242 5 4 2 2 in humid conditions, today in 3 weeks 55 1244 4 2 2 2 we evaluate the results of the experiment. Comparison 1245 3 l 2 2 for the purposes of Art. European Patent Application Example 2 1252 4 2 2 2 of formula (A). 1453 2 l 2 2 Mazu. The effect is denoted by the following measures: 1454 2 l 2 2 1 the plants have not germinated or completely destroyed 1455 4 l 2 1 overstock, 60 1456 2 l 2 2

-511

191 006

1457

1601

1806

1809

1812

1813

1823

1861

1890

1893

1898

2004

2101

2102

2110

2111

2113

2 2, 1 6 3

2 2 1 3 1 3 2

3 5 3 3 2 3 2 2 1 2 1 2 1 2 1 2 1 2 1

As is clear from the data in the Table, the agents containing the active ingredient of the formula I, when used in the pre-emergence process, are significantly more potent in the tested plants than the compounds containing the compound A.

Example 16

Demonstration of selectivity in pre-hatch ι θ applications

In the experimental sequence of Example 15, a large number of plant seeds are treated with formulations containing different amounts of the active ingredient. The results of the experiments are the previous

.. evaluated as in Example g. The results are summarized in the following table.

Experimental results (before hatching)

Effect, application rate kg of active substance / ha The compound number is 60 The compound number is 913 Number of compound 924 Experimental plant 0.25 0.12 0.06 0:03 0.25 0.12 0.06 0.03 0.25 0.12 0.06 0.03 wheat 4 7 9 9 9 tf '1? 9 maize 2 2 2 2 3 3 7 8 9 9 9 9 Avena fatua 2 2 3 4 5 6 6 8 9 9 9 9 9 Alopecurus myos. 2 2 2 2 2 2 2 3 4 9 9 9 Echinochloa c. g 2 2 2 2 2 2 3 3 6 6 9 9 Rottboellia ex. 2 3 3 3 3 3 4 4 7 9 9 9 Cyperus escul 3 3 3 3 2 3 3 5 3 4 9 9 soy 2 2 2 2 2 2 3 3 4 4 8 9 cotton 2 2 2 3 1 2 2 2 2 2 6 6 Abutilon 1 1 2 2 1 1 1 1 1 1 2 2 Xanthium sp. 2 3 3 3 2 2 2 3 2 2 9 9 Chenopodium sp. 1 1 2 2 2 2 2 2 2 2 2 2 Ipomoea 2 2 2 2 2 2 2 2 2 2 4 7 sinapis 2 2 2 2 1 1 1 1 1 2 6 6 Galium aparine 2 2 2 3 2 2 3 3 5 6 6 9 Viola tri colos 2 2 2 2 grounding 1 brake (k. 1 1 1 1 2 2 2 Effect, used quantity kg active substance / ha Experimental plant The compound number is 1161 THE compound number 1601 The compound number is 1812 0.25 0.12 0.06 0, Q3. .0,25 0.12 θ, 06th 0.03 0.25 0.12 0.06 0.03 v ™ wheat 7 8 '9 9 2 "3 6 9 9 9 9 maize 9 9 9 9 1 2 3 5 4 5 5 7 Avena fatua 7 8 8 9 2 2 3 4 6 7 7 8 Alopecurus myos. 4 4 5 7 2 2 2 ' 2 2 2 3 3 Echinochloa c. g 2 3 3 3 2 2 2 2 4 5 6 6 Rottboellia ex. 4 4 7 7 2 3 3 3 3 4 5 5 Cyperus escul 1 2 3 3 3 7 7 7 5 6 6 6 soy 6 9 9 9 2 2 3 3 2 2 3 3 cotton 4 • 4 4 9 2 4 6 7 2 2 3 3 Abutilon 1 2 4 4 3 3 4 4 1 1 1 2 Xanthium sp '. 4 6 6 8 1 1 2 2 3 4 4 5 Chenopodium sp. 2 2 3 3 1 1 2 2 1 1 1 2 Ipomoea 2 2 3 4 2 2 2 3 2 3 3 4 sinapis 1 1 2 3 2 2 2 3 1 1 1 2 Galium aparine 2 3 3 3 2 2 4 6 3 3 4 4 Viola tricolor 2 2 2 2 1 2 2 3 1 Ϊ 2 2

-521

191 006

Effect used

The compound number is 1812 applications, kg active ingredient / ha

Experimental crop of wheat

0,25 maize 2

Avena fatua 2

Alopecurus myos. 2

Echinochloa c. g. 2

Rottboellia ex. 2

Cyperus escul 3 soy 2 cotton 2

Abutilon 1

Xanthium sp. 1

Chenopodium sp. 2

Ipomea 2

Sinapis 2

Viola tricolor 2

0.12 0.06 0.03

Y — y y

3 4

4 5

2 2

2 2

3 4

4 4

2 2

2 3

2 2

2 2

2 4

3 3

3 4

2 3

Effect, application rate, kg active substance / ha Experimental plant The compound number is 1899 0015 0? Number of compound 1901 0:06 0:12 0:06 0.03 025 0:12 barley 5 S 6 7 7 r 9 wheat 6 7 7 8 9 9 9 9 maize 2 2 3 4 2 3 6 7 Sorghum hybr. 2 2 2 2 2 2 3 3 Avena fatua 4 5 6 7 4 5 6 7 Bromus tectorum 3 3 3 4 3 6 8 ' 8 Lolium perenne 1 1 1 1 2 2 2 3 Alopecurus myos. 1 1 1 2 2 2 2 2 Digitaria sang. 2 2 2 3 2 2 3 4 Echinochloa c. g. 2 2 3 3 2 2 3 3 Sorghum halep. 3 3 3 4 5 5 7 Kobbboellia ex. 1 3 j 4 í I 2 Cyperus escul 3 4 4 5 2 2 2 2 soy 2 2 2 2 ..... J ' - 2 "7 cotton 2 2 2 2 1 1 1 1

Effect, application rate, kg active substance / ha Experimental plant 0:12 Number of compound W 0,015 0.5 The compound number is 2113 0.06 0.03 0.25 0.12 0.06 barley 7 8 9 - 9 - - - wheat 9 9 9 9 3 4 7 9 maize 4 6 6 8 2 3 7 9 Sorghum hybr. 4 5 7 8 - - - - Avena fatua 8 9 9 9 2 2 4 9 Brumus tectorum 5 6 6 8th -  - - - Lolium perenne 2 3 4 6 - - - - Alopecurus myos. 2 3 4 4 1 1 2 2 Digitaría sang. 3 5 7 9 - - - - Echinochloa c. g. 4 6 6 7 1 2 2 2 Sorghum halep. 4 6 7 9 - - - - Rottboellia ex. 5 6 7 8 2 3 3 8 Cyperus escul 5 5 6 7 4 6 9 9 soy 2- -2- 3 4 2 2 3 3 cotton 2 2 3 4 2 2 3 6

-531

191 006

Effect, used heats. kg. ai / ha The compound number is 1899 experimental plant 0.12 0.06 0.03 0,015 Abutilon - 2 2 Sidi spinosa 2 2 2 2, Xanthium sp. 3 3 3 3 Amaranthus meadow. 1 1 1 1 Chenopodium sp. 2 2 2 2 Solanum nlgrum 2 2 2 2 Ipomoea 2 2 2 2 sinapis 1 1 1 1 Stellaria 1 1 1 1 Chrysanth. Leuc. 1 1 1 1 Galium aparine 1 1 3 4 Viola tricolor 1 1 1 1 Veronica sp .. 1 1 1 1

· 0.5

Compound number 1901 0.25 0.12 0.06

1 1

1 1

2 2

2 2

2 2

1 2

2 2

2 2

2 2

3 4

2 2

1 1

Effect, used heats. kg. active substance / ha experimental plant_

Abutilon

Sida spinosa

Xanthium sp.

Amaranthus meadow.

Chenopodium sp.

Solanum nlgrum

Ipomoea

sinapis

Stellaria

Chrysanth. Leuc.

Galium aparine

Viola tricolor

Veronica sp.

Compound number 1900 0.25 0.12 0.06

2 ~ 2

2 2

4 4

1 1

2 2

2 3

2 3

2 2

2 2

2 2

2 3

2 2

2 2

The compound number is 2113

2

2

2 1 1

2 1 1

3

2

7

2

7 1 '2

Example 17

Demonstration of a herbicidal effect following post - emergence use (contact effect)

A large number of weeds and crop plants are monocotyledonous and dicotyledonous, after emergence in 4-6 leaf condition. sprayed with an aqueous dispersion of the active ingredient using 4 kg of active ingredient / ha of active ingredient, then the plants are maintained at a temperature of 24 to 26 ° C and a relative humidity of 45 to 60%. The experiment is evaluated 15 days after treatment and the effect achieved, expressed in the values given in Example 15.

for comparison purposes, no. An agent containing the compound of Example 2 of the European Patent Specification (Formula A) is used.

Post-emergence effect

The application rate is 4 kg of active ingredient per hectare

The compound Ave- Walk- Lo- Sola- Slna- Stel- Phasama na riallum num pis lerla seolus

6

7

7

6

7

4 4 8 3 3 8 4 4 8 4 3

4 4

4 3

4 3

3 4

81 83

192

131

132

195

196,200

301

302

303,312,316,329

331

332

333 337 471 497 500 522 524 526

4 5

3 4

7 4

7 2

6 3

5 4

7 5

4 4

5 5

6 5

6 5

6 5

5 5

6 4

6 4

6 6

4 2

6 3

9 6

6 5

4 2

3 3

4 5

4 6

5 4

6 4

2 4

3 3 2 2 2 3 12 3 3

2 3 3

13 3 2 2 2 3 2 2 2 3 2 2 2 3 12 3 3

3 3 4 2 2 4 4 2 3 4 4 2 2 3 3 2 2 3 3 2 2 3 3 2 3 3 4 113 2 113 3

2 4 5 12 2 3 2 2 2 3

3 3 2 3 4 4 2 2 3 4

2 3 12 2 3 2 2 2 3

-541

191 006

527 3

528 4

532 5

541 7

551 6

557 7

587 6

595 5

9

901 2

902 7

919 3

1161 7

1202 3

1203 4

1212 7

1223 3

1242 6

1244 4

1245 5

1252 6

1453 2

1454 2

1455 2

1456 3

1457 4

1601 2

1806 6

1809 4

1815 5th

1823 4th

1861 8th

4 2

5.3

5 2

5 1

4 2

5 2

5 2

3 2

7 3

3 2

3 2

2 2

4.1

3 2

4 3

4 6

4 1

3 3

4 2

3 3

4 3

2 1

2 1

2 2

3 1

3 1

3 2

3 2

2 1

3 2

3 2

3 2

2 4

3 4

3 4

2 3

2 4

3 3

2 3

2 3

3 5

3 3>. 3 3

4 2

3 4

2 3

2 4

7 7

2 3

2 3

2 4

4 5

4 4

2 3

3 3

2 2

2 3

3 4

3 3

2 2

3 3

4 3

2 4

3 4

June 6, 1890

April 4, 1893

April 4, 1893

2/2/2004

2101 2. 3

2102 2 2

2110 2 1

2111 2 1

12 2 3 · 2 2 3 2

1 3 2 2

2 2 2 3

2 2 2 2

2 2 3 2

2 2 1 3

2 2 · 3 3

2 2 2 2

In the post-emergence series of compounds, the compounds of formula (I) showed moderate activity against monocotyledonous plants and strong activity against dicotyledonous plants. In contrast, a comparative experiment with the known compound has shown that the agent containing it has only low activity against monocotyledonous plants and only moderate activity against dicotyledonous plants.

It is clear from the comparative results of the above Tables that the agents containing the known compound (A) are superior to the agents according to the invention in both herbicidal and post-emergence herbicidal activity.

Example 18

Demonstration of selectivity in post-emergence application

The experimental procedure described in Example 17 is followed and a larger number of plants are treated with a composition containing different amounts of the active ingredient. The evaluation was carried out as in Example 15. The results are summarized in the following table.

Effect, rate of application kg active substance / ha _____ Test results (after emergence)

Ά COMPOUNDS ^ Olna Compound No. 924

Pilot plant barley ^- wheat corn dry rice

Avena fatua

Alopecurus nyos.

Echinochloa c. g.

soy cotton

Abutilon

Xanthium sp.

Amaranthus meadow.

Chenopodium sp.

Ipomoea

sinapis

Steilaria

Chrysanth. Leuc. Galium aparine Viola tricolor

0.25 0.12 0.06 0.03

9 9 9

4 7 9

5 8 9

5 8 9

2 2

2 6 6

3 3 3

6 7 9

2 2 2

1 11

2 2

3 3 4

1111

2 2

2.2 2

0.25 0.12 0.06 0.03

V-tf 'T>' - tf—

9 9 9

9 9 9

4 6 9

9 9 9

3 3

7 7 7

1112

2 3 3

3 4 4

3 3 3

3 3 3

4 4 4

3 3 3

The compound number is 1601

0.25 0.12 0.06 0.03

6 2 4 7 7 2 3

3 2 2 4 4 9 9

1

3 2 2 2 2

9 4 8 7 9 4 6 3 3

3 6 6 9 9

3

4 2 2 2 2

-551

191 006

Effect, quantity used kg.

ai / ha

Experimental plant_ barley wheat corn dry rice

Avena fatua

Alopecurus nyos.

Echinochloa c. g.

soy cotton

Abutilon

Xanthium sp.

Amaranthus meadow.

Chenopodium sp.

Solanum nigrum

Ipomoea

sinapis

Stellaria

Crysanthe leuc.

Galium aparine

Viola tricolor

Veronica sp.

The color of the compound is ^- 1599 TCC and number of TCW

0:12

ΤΓ "

Effect, quantity used kg. ai / ha Experimental plant The compound number is 1899 The compound number is 19 0.12 0.06 0.03 0,015 0.5 0.25 0.12 0.06 barley 9 wheat 7 9 9 9 7 9 9 9 maize 2 7 7 8 4 7 7 7 dry rice 4 4 7 7 7 7 8 9 Avena fatua 7 8 8 9 6 9 9 9 Alopecurus myos. 3 3 3 3 4 4 6 6 Echinochloa c. g. 3 3 3 3 6 7 7 9 soy 2 2 2 2 2 2 2 2 cotton 6 6 6 6 6 6 7 7 Abutilon 1 1 3 4 3 4 4 4 Xanthium sp. 2 3 3 3 1 1 1 1 Amaranthus meadow. 1 1 2 2 2 2 2 3 Chenopodium sp. 1 1 1 1 1 1 2 2 Solanum nigrum 2 2 3 3 4 4 4 4 Ipomoea 3 3 3 4 4 4 4 5 sinapis 2 2 2 2 3 3 3 3 Stellaria 2 2 2 2 2 3 4 4 Crysanthe leuc. 1 1 1 1 3 3 3 3 Galium aparine 7 7 7 7 3 4 6 6 Viola tricolor 2 3 3 3 6 6 6 6 Veronica sp. 2 2 2 2 6 6 6 6

-561

191 006

Effect, Amount used kg. Compound number 190ÖA compound number 2113 active ingredient / ha

Experimental plant 0.25 0.12 0.06 0.03 0.25 0.12 0.06 0.03

barley wheat J ' 9 T ~ 9 9 ~ 9 ~ 9 8 9 9 9 maize 3 6 7 8 4 4 9 9 dry rice 4 4 4 4 4 4 • 6 6 Avena fatua 3 6 7 9 3 4 9 9 Alopecurus myos. 3 4 4 5 3 4 4 4 Echinochloa c. g. 3 3 4 4 2 2 2 2 soy 2 2 2 2 3 4 4 4 cotton 3 4 5 6 9 9th 9 9 Abutilon 2 2 3 3 6 7 8 9 Xanthium sp. 2 2 2 3 1 1 1 2 Amaranthus meadow. 2 3 3 3 - - _ Chenopodium sp. 2 2 4 4 3 6 6 7 Solanum nígrum 5 6 6 7 - - - Ipomoea 4 4 4 4 5 6 6 7 sinapis 2 2 2 2 4 4 4 4 Stellaria 2 2 2 2 - __ _ Crysanthe leuc. 2 2 2 2 - - - Galium aparine 1 1 1 1 2 3 4 9 Viola tricolor 2 2 2 2 2 2 2 3 Veronica sp. 2 2 2 2 - - - -

Example 19

Inhibition of germination of stored potatoes

The commercially available 'Ugenta' germ free potatoes are washed and dried. Subsequently, these potatoes are immersed in the various concentrations of active ingredient emulsions listed below for a few minutes, placed on filter paper, and stored at 14 ° C and 21 ° C in the dark at 50% relative humidity. The results of the experiments were determined 34 days after the treatment. The evaluation was performed according to the following measure:

there is no germination (as before treatment) an approximately 50% inhibition of germination 9 equal to that of untreated control potatoes.

At the same time, the weight loss of tubers in% bap and the weight of germs relative to untreated control were determined.

The results are summarized in the following table.

The chemical- Bath let conc.

number (ppm)

Storage temperature 21 C

Germ mass weight mass formation (g) (%) control (%)

germs tubers control 5o 9 10 12.2 1899 1000 3 3.0 5.9 8.4 1900 1000 7 39.4 77.4 11.3

Experimental results: Inhibition of germination of stored potatoes

The chemical bath Storage temperature 14 ° C being number conc. (Ppm) germs tubers Germ- formation Dej crowd (8) crowd % control crowd (%) control 0 9 52.8 100 10.4 1899 1000 1 0 0 5.5 1900 1000 3 4.8 9.1 5.4

Example 20

Inhibition of growth of tropical cover crops

The experimental plants (centrosema plumieri and centrosema pubescens) were grown to adulthood and then cut back to a height of 60 cm. The active ingredient listed below was sprayed onto the plants after 7 days in the form of an aqueous emulsion. The experimental plants were then maintained in a 70% relative humidity and 6000 lux artificial light for 14 hours daily at 27 ° C during the day and 2 ° C at night. The experiment was evaluated 4 weeks after treatment, during which time

a) finding% new growth compared to control,

(b) the percentage increase in weight relative to the control; and (fc) the phytotoxicity according to the following linear scale:

= plants destroyed, 9 = plants not damaged.

The results are summarized in the following table.

-571

191 006

Plant A Compound

Experimental Results: Inhibition of Growth at Cover Crops Used New Growth Ui sú

phytotoxicity

number active ingredient) hectare visually control %-in 8 control -in ^. 'Entrosema T899 10 0 2 --- 1- -1 pubescens 1899 30 10 9 18 8 1899 100 0 2 4 8 1900 10 0 1 2 9 1900 30 0 2 4 9 1900 100 0 0 0 0 Centrosema 1899 10 20 31 50. 9 plumleri 1899 30 0 0 0 8 1899 100 0 4 6 8 1900 10 30 29 47 9 1900 30 10 26 42 9 1900 100 0 6 10 9

EXAMPLE 21 Comparative experiments were performed in accordance with U.S. Pat. as well as compositions known in the art as "B". The latter corresponds to Table 15 of U.S. Patent No. 4,190,432.

Experimental conditions and evaluation were the same as described in Examples 16 and 18. The studies were extended to a few additional plants and were tested at extremely low rates of application (eg 2 g active ingredient per hectare in the pre-emergence test and 8 g active substance in the post-emergence test).

The test results are presented in the following Tables.

Effect

Amount of active substance used g / ha Test plants

Barley

Wheat

Maize

Rice, dry Avena fatua Alopecurus myos. Echinochloa c. g. Rottboellia ex. Cyperus escul.

Soya Cotton Sugar Beet Abutilon Sida spinosa Xanthium sp. Amaranthus meadow. Chenopodium sp. Solanium nigrum Ipomoea Sinapis Stellaria

Chrysanth. Leuc. Galium aparine Viola tricolor Veronica sp.

Compound "B"

No. 1899 compound

5

6

2

1

4

1. 2

3

3

2

2

2

1

2

3

2

2

2

2

2

2

2

1. 2

1

9

9

5

1

8

2

3

4

6

2

2

2

2

2

4

2

2

3

2

2

2

2

4

2

1 .2.

-581

191 006

Post-emergence experiment

TOT ”- Amount of active substance used g / ha Plants tested _

Wheat

Corn Rice, dry Avena fatua Alopecurus myos. Echinochloa c. g. Rottboellia ex. Cyperus escul. Soya Cotton Sugar Beet Abutilon Xanthium sp. Chenopodium sp. ipomea Sinapis

Galium aparine Viola tricolor

500 125g—.

6 7 8 6 8

7 6 8 9 9

8 9 9

8

6 8 9 6 7 8 9 8 9

7 8 9 8 9 ”· 30 8 —9 ... 9 9—

9

9

9

9

9

9

9

9

9

9

9

8

9

9

8

9

9

No. 1899 compound 500 125 30

-7-91 2 6

4 7

7 8

3 3

3 3

6 6

5 6

2 2

6 6

2 2

1 3

2 3

1 1

3 3

2 2

6 6

2 3

4 2 6 2 7 3

In the pre-emergence study, formulations containing Compound B qq show good to moderate herbicidal activity at the highest application rate (500 g active substance / hectare), whereas they are almost completely ineffective at 30 g active substance / hectare. However, selectivity! nor does the domain appear. In contrast, the 1899 The formulations of the present invention containing the compound of the invention have a good to very good herbicidal activity at a rate of application of 500 g active ingredient / hectare and have a good to very good activity against weeds at the application rate of 30 g / ha, g / ha and 2 g / ha. then monocot crops such as barley, wheat and corn will tolerate them well. _n

In the post-hatching study, formulations containing Compound B were virtually ineffective in all of the tested application rates. Formulations containing 500 to 100 g / ha have good to very good herbicidal activity in all tested plants. From 125 kg / ha to 8 g / ha, wheat, maize, rice and cotton show selectivity, with qq and even 8 g / ha herbicidal activity against dicotyledonous weeds.

In summary, it is to be understood that the invention is described in U.S. Pat. Compounds containing the compound of the prior art exhibit significantly improved efficacy as well as tolerance to crop plants, both prior to and after emergence, as compared to the prior art "B" formulations.

Example 22

Dilution with water of one of the emulsifiable edges listed in Example 14 (b) above, from the compounds of formula (I) below, provides the appropriate concentration of the active ingredient in the formulation to be used. The preparation thus prepared is used in the following tests.

Investigation of herbicidal activity before emergence of plants

Plastic containers are filled with expanded vermiculite (specific gravity: 0.135 g / cm ³ , water adsorption capacity: 0.565 liters / liter). The vermiculite is saturated with an aqueous emulsion of the active ingredient in deionized water at a concentration of 70.8 ppm, The seeds of the following plants are then sprayed onto the surface: Nastrurtium offlcinalis, Agrostis tenuls, Stellaria media and Digitaria sangulnalis, and the test vessels are then stored at 20 ° C and 70% relative humidity in a climate chamber and approximately 20 kLux. During the 4-5 day germination phase, the dishes are covered with light-permeable material to increase local air humidity and irrigated with deionized water. 12 days after sowing, the experiment is evaluated and impact is evaluated as follows:

the plants did not germinate or were completely destroyed

2-3 very strong effect

4-6 medium effect

7-8 little effect ineffective (like untreated control)

-591

191 006

Pre-emergence effect

The Digltaris number of the compound is Mastur Stella-Agrosr tium ria tis

- _f '2

102

112

125

195

302

312

317

329

335

342

344

348

350

358

362

368

373

392

399

406

442

445

446,454,468,470

473

474,483,496,501,526,553,595,598,600,601,904,917,924,930,941,976

1211

1214

1217

1227

1246

1249

1279

1296

-3Γ

2

1

1

2

4

2

2

2

2

2

2

1

2

2

2

2

2

3

2

3

2

2

2

2

2

2

2 <2 2 '- • 2 1

1

3

2

2

2

1

1

3

3

2

1

3

2

1

2

2

1

2

1

2

2

3

1

5

4

1

1

2

2

4

1

2

7-ΤΙ 2

1

1

2

4

2

2

2

2

2 · 2

2

1

2

2

2 '4

2

3

2

3

2

4

4

1

2

2

2

3

2

2

3

2

1

2

1

1

3

4

2

1

5

2

1

2

1

1

2

2

5

6

5

4. 7

6

1

1

4

5

2

2

3

1306

1307

1308

1309

1310 1316

1320

1321

1325

1326

1343

1344 1601

1832

1833 1847 1855 1861

1899

1900

1901 2004 2101 2110 2113

1 1 '2 2 2

2 2

1 3

1 1

1 4

1 2

1 2

1 1

2 2

1 2

2 2 .1 2

2 2

1 2

3 2

2 2

3 6

11

1 2

2 2

1 2

1 2

1 2

1 2

It is clear from the data in the Table that the formulations containing the compounds of the general formula (1) have a strong nerbicidal activity, although the selectivity of some of the formulations tested on the basis of the results can be deduced.

Example 23

Diluted gg of water of the emulsifiable agent given in Example 14 (b) above in the salts of the compounds of formula (I) below form an appropriate concentration of the active ingredient in the formulation to be used. The preparation thus prepared is used in the following tests.

Investigation of herbicidal activity before emergence of plants

Plastic containers were filled with expanded vermiculite (species40 weight: 0.135 g / cm ³ , water adsorption capacity: 0.565 lite / liter). The vermiculite is saturated with a deionized aqueous drug emulsion containing the test salt at a concentration of 70.8 ppm, i.e. 0.0007%. Seeds of the following plants are then applied to the surface:

Nasturtium officinalis, Agrostis tenuís, Stellaria media and Digitaria sanguinalis. The test vessels were then placed in a climate chamber at 20 ° C and 70% relative humidity and maintained at ca. Illuminated with 20 kLux. During the 4-5 day germination phase, the pot is covered with two light-permeable materials to increase local humidity and watered with deionized water. After day 5, the solution water fertilizer (Greenzit, manufactured by Ciba-Geigy) is added to the irrigation water. On the 12th day after sowing, the experiment is evaluated and the experimental plants exposed to the plant. as follows:

1: The plants have not germinated or completely died

2-3: very strong effect 4-6 medium effect 7-8: slight effect

9: ineffective (as untreated control)

-601

Pre-emergence effect:

The concentration of the active ingredient is 70.8 ppm The compound Other- Stella- Agrps- · Dlgi number (salt) tur- ria ti8 ria 2 (sodium salt) lITHIUM 1 2 1 2 78 (sodium salt) 1 1 1 1 358 (isopropylamine salt) 2 2 1 1 406 (potassium salt) 1 2 1 2 470 (sodium salt) 1 1 1 1 483 (triethylamine salt) 1 2 > 1 2 496 (sodium salt) 1 1 1 1 595 (potassium salt) 2 2 2 2 600 (potassium salt) 1 1 1 1 601 (sodium salt) 2 2 2 2 1306 (sodium salt) 1 1 1 1 1307 (isopropylamine salt) 1 2 2 2 1847 (sodium salt) 2 2 3 2 1900 (sodium salt) 1 2 1 2

It is clear from the data in the table that the formulations containing the salt of the compound of formula (I) have a strong herbicidal action and the results suggest that some of the formulations tested have a high selectivity.

Claims (5)

PATENT CLAIMS CLAIMS 1. A herbicide and a plant growth regulator, characterized in that 5-99.9% by weight of a carrier and / or other additives, preferably calcium dodexylbenzene sulfonate, castor oil polyethylene glycol ether, cyclohexanone, xylene, ethylene glycol monomethyl ether, polyethylene glycol, N-methyl-2-pyrrolidone, epoxidized coconut oil, kaolin, high dispersion silica gel, attapulgite, talc, sodium lignin sulfonate, sodium lauryl sulfate, diisobutyl naphthalene sulfonate, octylene glycol, at least one of 0.001 to 95% by weight of at least one of N- (phenylsulfonyl) -N-triazinyl or pyrrolidinyl (I) as active ingredient in at least one of cellulose, ethylene glycol, nonylphenyl polyethylene glycol ether, formaldehyde solution, water or isopropylamine. urea, optionally in the form of a basic addition salt, preferably an alkali metal or amine salt, wherein A is 1-5 halogen atoms C 1-5 alkyl optionally substituted with mal or C 1-4 alkoxy, C 1-4 alkylthio, C 1-4 alkylsulfinyl or C 1-4 alkylsulfonyl or optionally substituted with 1 or 2 halogens substituted C2-C6 alkenyl. -E represents a methyl group or a nitrogen atom, X is oxygen, sulfur, sulfinyl or sulfonyl, -Z is oxygen, sulfur, sulfinyl or sulfonyl, -Z is oxygen or sulfur, -m is 1 or 2, -R j is hydrogen, halogen, C 1-5 alkyl or C 1-4 alkoxy, -R a is hydrogen or halogen, R ₃ and R ₃ are independently C 14 alkyl, C 14 alkoxy, C 14 alkylthio, C 14 haloalkyl, or halogen. with the proviso that m is 2 when X is sulfur, sulfinyl or sulfonyl and A is at the same time C 34 alkenyl. 2. An agent according to claim 1, characterized in that it contains an active ingredient of the formula I in which A is a C 14 alkoxy group, a C 14 alkylthio group, a C 14 alkylsulfinyl group or a C 14 alkylsulfonyl group. C 1-5 -alkyl or C 2-6 -alkenyl optionally substituted with 1 or 2 halogens, 3. An agent according to claim 1, characterized in that it contains an active ingredient of the formula (I) in which A represents a C 1-5 haloalkyl group containing 1 to 5 halogens. 4. An agent according to claim 2 wherein the active ingredient is a compound of formula I wherein Z is oxygen. 5. An agent according to claim 2, characterized in that it contains as an active ingredient a compound of formula (I) in which R ₃ and R 1 together represent up to 4 carbon atoms. 6. The agent of claim 2, wherein the agent is a compound of formula (I) wherein Z is oxygen and m is 1. 7. The agent of claim 2, wherein the agent is a compound of formula I wherein Z is oxygen and m is 2. 8. An agent according to claim 6 wherein the active ingredient is a compound of formula (I) wherein the -X-A group is in the 2 or 3 position relative to the sulfonyl group. 9. An agent according to claim 8 wherein the active ingredient is a compound of formula I wherein the -X-A group is in the 2-position relative to the sulfonyl group. 10. An agent according to claim 7 wherein the active ingredient is a compound of formula (I) wherein the two -X-A groups are in the 2 and 5 position relative to the sulfonyl group. 11. An agent according to claim 2 wherein the active ingredient is a compound of formula (I) wherein only one -XA group is in the 2-position relative to the sulfonyl group and R ₃ and R ₄ together are up to 4 contains carbon atoms .. 12. An agent according to claim 2 wherein the active ingredient is a compound of formula (I) wherein two -XA groups are present at the 2- and 5-positions relative to the sulfonyl group, together with the R ₃ and R ₄ groups. And -611 contain up to 4 carbon atoms. 13. An agent according to claim 11 wherein the active ingredient is a compound of formula (I) wherein R 1 is hydrogen and R 1 is in the 5 or 6 position relative to the sulfonyl group. 14. An agent according to claim 13 wherein the active ingredient is a compound of formula I wherein R _{2 is} hydrogen or fluoro, and R ₃ and R 4 are C 14 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, or halogen, with R ₃ and R _{4 taken} together containing up to 4 carbon atoms. An agent according to claim 14; wherein the active ingredient is a compound of formula I wherein R _{2 is} hydrogen, R ₃ and R ₄ are C 14 alkyl, C 14 alkoxy, methylthio, or halogen. 16. An agent according to claim 15, characterized in that it contains as an active ingredient a compound of the formula I in which X represents an oxygen atom or a sulfur atom. 17. An agent according to claim 16, wherein the active ingredient is a compound of formula I wherein A is a C 2 -C 8 alkoxy-aldl group, C 1 -C 2 haloalkenyl, or or C2-C6 alkenyl. 18. An agent according to claim 17, wherein the active ingredient comprises (1) a compound of formula wherein the C2-8 alkoxyalkyl group, R ₃ and R ₄ is methyl or ethyl, chlorine or methoxy, 19. An agent according to claim 17, characterized in that it contains as active substance (I) compound in which the C 2-6 alkenyl group, R ₃ and R ₄ is methyl or ethyl, chloro or methoxy. 20. An agent according to claim 17, wherein the active ingredient is a compound of formula I wherein A 1 or 2 is halogen substituted vinyl and R ₃ and R ₄ are methyl or ethyl, chlorine or methoxy. . 21. An agent according to claim 2, wherein je 1 1 em this ve, that contains the active substance (I) compound wherein Z is sulfur, X is oxygen, R ₃ and R ₄ are independently C 1-3 alkyl, 1 C 3 -C 3 alkoxy or C 1 -C 3 alkylthio having up to 4 carbon atoms in total and A is -CH ₂ -CH = CH ₂ , -CH ₂ -CH = CH-CH ₃ , -CH ₂ -C ( _{CH3> CH2,} methoxyethyl, methoxy-methyl, or CHC1 = CC1 group, while the -X group at the 2-position. 22. The agent of claim 2, wherein the active ingredient is N- [2- (allyloxy) phenylsulfonyl] -N- (4-methoxy-6-methyl-1,3,5-triazin-2-yl). ) contains urea. 23. An agent according to claim 3, wherein the active ingredient is a compound of formula (I) wherein the -X-A substituent is in the 2 or 3 position of the benzene ring. 24. An agent according to claim 3, characterized in that it contains as an active ingredient a compound of formula 0 having only one X-A substituent at the 2-position of the benzene ring. 25. An agent according to claim 3, wherein the active ingredient is a compound of formula 0) wherein the substituents R ₃ and R ₄ each independently have up to 2 carbon atoms. 26. An agent according to claim 3, wherein one em je 1 it is that it comprises a 0) compound as an active ingredient, wherein R represents _a substituent, and R is hydrogen. 27. An agent according to claim 3, wherein the active ingredient is a compound of formula 0) having only one -XA substituent at the 2-position of the benzene ring, the substituents R ₃ and R ₄ and each independently contains up to 2 carbon atoms while F and R _{2 are} hydrogen. 28. An agent according to claim 3, wherein je 1 1 em this ve to an active ingredient comprising (I) a compound of the formula wherein R, and R ₂ is hydrogen, X and Z are oxygen, E is nitrogen, R ₃ methoxy, R ₄ methyl - or the methoxy group, the difluoromethyl group and the -XA group are in the 2-position of the benzene ring, and X may also be a sulfur atom when R _{3 is a} methyl group. 29. The agent of claim 3, wherein the active ingredient is N- [2- (difluoromethoxy) phenylsulfonyl] -N '- (4,6-dimethoxy-1,3,5- triazin-2-yl) urea. 30. The agent of claim 3, wherein the active ingredient is N-9- (difluoromethoxy) phenylsulfonyl] -N- (4-methyl-6-methoxy-1,3,5-triazin-2-yl). contains carbamld. 31. The agent of claim 3, wherein the active ingredient is N- [2- (difluoromethylthio) phenylsulfonyl] -N- (4-methyl-6-methoxy-1,3,5-triazine-2). -yl) urea. 32. The agent of claim 3, wherein the active ingredient is N- [2- (1,1,2,2-tetrafluoroctoxy) phenylsulfonyl] -N (4-methyl-6- containing nethoxy-1,3,5 triazin-2-yl) urea. 33. An agent according to claim 3, wherein the active ingredient is N- [2- (trifluoromethoxy) phenylsulfonyl] -N '- (4-methyl-6-ethoxy-1,3,5-triazine-2-one). il) urea. 34. The agent of claim 3, wherein the active ingredient is N- [6-chloro-2- (difluoromethoxy) phenylsulfonyl] -N '- (4-methyl-6-methoxy). contains 3,5-triazin-2-yl) urea. An agent according to claim 3, wherein the active ingredient is N- [2- (difluoromethoxy) 5-fluorophenylsulfonyl] -N '- (4-methyl-6-methoxy-1, Contains 3,5 triazin-2-yl) urea. 36. The agent of claim 3, wherein the agent is a compound of formula 0) wherein A is C 1 -C 5 haloalkyl, with the proviso that m is 2, if the time is -CHF ₂ -CF _3, -CH _{2 -CF-3j} -CFj CHFj, _-CF2 -CHFC1, -CF, or -CHFBr _-CF2 -CHF-CF _3, R ₃ or -0CH ₃ It represents CH ₃ group R4 -OCHj, -CH _3, or OC ₂ H 5 group and benzolgyű62 -621 is unsubstituted or monosubstituted at the 2, 3, 5 or 6 position with the sulfonyl group at the fluorine, chlorine, or bromine or -CH 3 - groups. The agent of claim 36, wherein the agent is a compound of formula (I) wherein Z is oxygen. 38. The agent of claim 36, wherein the active ingredient is a compound of formula (I) wherein the total number of carbon atoms of the substituents R ₃ and R _{4 is} up to 4. 39. The agent of claim 36, wherein the active ingredient is a compound of formula I wherein Z is oxygen and m is 1, 40. The agent of claim 36, wherein the active ingredient is a compound of formula I wherein Z is oxygen and m is 2. 41. An agent according to claim 39 wherein the active ingredient is a compound of formula (I) wherein the -X-A group is in the 2 or 3 position relative to the sulfonyl group. 41. An agent according to claim 41 wherein the active ingredient is a compound of formula (I) wherein the -X-A group is in the 2-position. 43. An agent according to claim 40 wherein the active ingredient is a compound of formula (I) wherein the two -X-A groups are in the 2 and 5 position relative to the sulfonyl group. 44. An agent according to claim 37, wherein the active ingredient is a compound of formula (I) wherein there is only one -XA group at the 2-position relative to the sulfonyl group at R ₃ and R _4. and the substituents together contain up to 4 carbon atoms. 46.45. The agent of claim 1, wherein the active ingredient is a compound of formula (I) wherein A is -CHF ₂ -CF 3 or -CH ₂ -CH ₂ Cl. 47. The agent of claim 44, wherein the active ingredient is a compound of formula (I) wherein R 1 _is hydrogen and R _{2 is in} the 5 or 6 position relative to the sulfonyl group. 48. The agent of claim 47, wherein the active ingredient is a compound of formula I wherein R _{2 is} hydrogen or fluorine. 49. The agent of claim 48, wherein the active ingredient is a compound of formula (I) wherein X is oxygen or sulfur. 50. An agent according to claim 49, characterized in that it contains as active substance (I) compound wherein R ₂ is hydrogen, R, fluoro or chloro, trifluoromethyl, chloromethyl mctil-, ethoxy, isopropyloxy, ethyl or methoxy; and R _{4 is} methyl, ethyl, methoxy or ethoxy. 51. The agent of claim 50 wherein the active ingredient is a compound of formula I wherein X is O. 52. An agent according to claim 51, wherein the active ingredient comprises (1) a compound of general formula wherein A represents a _-CF2 G radical, where G is hydrogen, fluorine, chlorine or bromine, _-CF3 or -CH ₃ . 53. The agent of claim 52, wherein in CF ₂ G, G is chloro, bromo or CF ₃ . 54. The agent of claim 53, wherein the active ingredient is a compound of formula I wherein A is -CH ₂ F, -CH ₂ -CH ₂ F, or -CH ₂ CH ₂ Cl. 55. The agent of claim 3, wherein the active ingredient is a compound of formula I wherein Z is sulfur, X is oxygen or sulfur, and R ₁ and R ₄ are each independently C 1-3 alkyl, C 103 alkoxy, or C 1-3 alkylthio which together contain up to 4 carbon atoms. A is -CHF _2, -CF _3, -C ₂ F, -CHF ₂ or -CF ₂ group and the group -X is in the 2-position. 56. The agent of claim 36, wherein the active ingredient is N- [2- (difluoromethoxy) phenylsulfonyl] -N- (4-methyl-6-methoxy-1,3,5-triazole, n). -2-yl) urea. 57. The agent of claim 36, wherein the active ingredient is N- [2- (difluoro-T-methoxy) phenylsulfonyl] -N '- (4,6-diethoxy-1,3,5-triazin-2-yl). ) -urea. 58. The agent of claim 36, wherein the active ingredient is N-1,2-difluoromethoxy-phenylsulfonyl] -N '- (4-chloro-6-methyl-pyrimidin-2-yl) -urea. contain. 59. The agent of claim 36, wherein the active ingredient is N- [2- (pentafluoroethoxy) phenylsulfonyl] -N- {4-methoxy-6-methyl-1,3,5-triazin-2-yl. ) -urea. 60. The agent of claim 36, wherein the substance is N- [2- (difluoromethylthio) phenylsulfonyl] -N- (4-chloro-6-methoxypyridin-2-yl) urea. . 61. The agent of claim 36, wherein the active ingredient is N- [2,5-bis (difluoromethoxy) phenylsulfonyl] -N- (4-methoxy-6-methyl-1,3, Contains 5-triazin-2-yl) urea. 62. The agent of claim 36, wherein the active ingredient is N- [2- (difluoromethoxy) phenylsulfonyl] -N- (4-methoxy-6-isopropyl-1,3,5- triazin-2-yl) urea. 63. The agent according to claim 36, wherein said compound is N- [2- (difluoromethyl methylthio> phenylsulfonyl] -N ^'- (4-ethyl-6-methoxy-l, 3,5-triazine -2 l) urea. 64. The agent of claim 36, wherein the active ingredient is N- [2- (difluoromethoxyphenylsulfonyl) -N- (4-chloro-6-methoxypyrimidin-2-yl) urea. 65. The agent of claim 1, wherein the active ingredient is N- [2- (2- (pentafluoroethoxy) phenylsulfonyl] -N- (4,6-dimethoxy-1,4,5-triazin-2-yl). contains urea. -631 66. The agent of claim 1, wherein the active ingredient is N- [2- (2-chloroethoxy) phenylsulfonyl] -N- (4-methoxy-6-methyl-1,3,5- containing triazin-2-yl) urea. 67. The agent of claim 1, wherein the active ingredient is N- [2- (2-chloroethoxy) phenylsulfonyl] -N- (4,6-dimethoxy-1,3,5-triazine-2). -yl) urea. 68. The agent of claim 1, wherein the active ingredient is N- [2- (2,3-dichloropropyloxy) phenylsulfonyl] -N- (4-methoxy-6-methyl-1,3, Contains 5-triazin-2-yl) urea. 69. The agent of claim 1, wherein the active ingredient is N- [2- (difluoromethoxy) phenylsulfonyl] -N- (4-ethyl-6-methoxyl-1,3,5-triazine-2). -yl) -carbanide. 70. The agent of claim 1, wherein the ship substance is N- [2- (allyloxy) -5-methylphenylsulfonyl] -N- (4-methoxy-6-methyl-1,3,5- contains triesin-2-yl) -carbanide. 71. The agent of claim 1, wherein the active ingredient is N- [2- (2-methyloxy) phenylsulfonyl] -N- (4-methoxy-6-methyl-1,3,5-triazine) -2-yl) urea. 72. The agent of claim 1 wherein the active ingredient is N- [2- (2-methyl-oxt) -phenylsulfonyl] -N- (4,6-dimethoxy-1,3,5-triazine-2- il) · urea. 73. An agent according to claim I wherein the active ingredient is N- [2- (2-methyloxy) phenylsulfonyl] -N- (4,6-dimethoxy-1,3,5-triazine-2). -yl) · -urea. 74. The agent of claim 1, wherein the active ingredient is N- [2- (2-butenyloxy) phenylsulfonyl] -N- (4-methoxy-6-methyl-1,3,5-triazine) -2-yl) -carbamide. 75. The agent of claim 1, wherein the active ingredient is N- [2- (2-butenyloxy) phenylsulfonyl] -N- (4,6-dimethoxy-1,3,5-triazine-2). -yl) urea. 76. The agent of claim 1 wherein the active ingredient is N- [2- (1,2-dichloro-vinyloxy) -phenylsulfonyl] -N- (4-methoxy-6-methyl-1,3). , 5-thiazin-2-yl) urea. 77. The agent of claim 1, wherein the active ingredient is N- [2-allyloxy) phenylsulfonyl] -4,6-diethoxy-1,3,5-triazin-2-yl ) -urea. 78. The agent of claim 1, wherein the active ingredient is N- [2- (allyloxy) -phenylsulfonyl] -N- (4-ethoxy-6-methyl-1,3,5-triazine-2- il) urea. 79. The agent of claim 1, wherein the active ingredient is N- [2-allyloxy) phenylsulfonyl] -N (4-methoxy-6-isopropyloxy-1,3,5-triazine-2-one). il) -carbanide. 80. The agent of claim 1, wherein said agent is. containing N- [2-allyloxy) phenylsulfonyl] -N'-4,6-dimethoxy-1,3,5-triazin-2-yl) urea as active ingredient. 81. The agent of claim 1, wherein the active ingredient is N- [2- (1,2-dichloro-vinyloxy) phenylsulfonyl] -N '- (4,6-dimethoxy> 1,3, Contains 5-triazin-2-yl) urea. 82. The agent of claim 1, wherein the active ingredient is N- [2- (1,2-dichlorovinyloxy) phenylsulfonyl] -N- (4-chloro-6-methoxypyrimidine-2-). il) • Contains urea. The agent of claim 1, wherein the active ingredient is N- [2- (methoxy-ethoxy) -phenylsulfonyl-N, (4-methoxy-6-methyl-1,3,5-triazin-2-yl). ) · · Urea. The agent of claim 1, wherein the active ingredient is N- [2-methoxymethoxy-phenylsulfonyl] -N- (4-methoxy-6-methyl-1,3,5-triazin-2-yl). -carbainide. 85. The agent of claim 1, wherein the active ingredient is N- [2- (methoxyethylthio) methylsulfonyl] -N- (4-methoxy-6-methyl-1,3,5-triazine). Contains 2 µl) -urea. 86. The agent of claim 1, wherein the active ingredient is N- [2- (methoxyethoxy) phenylsulfonyl-N- (4-ethoxy-6-methyl-1,3,5-thiazin-2-yl). ) · · Urea. 87. The agent of claim 1 wherein the active ingredient is N- [2- (methoxyethoxy) phenylsulfonyl-N- (4-methoxy-6-methylpyrimidin-2-yl) urea. 88 _; A process for the preparation of N- (phenylsulfonyl) -N-triazinyl or pyrimidinylurea derivatives of formula (I): A is C 1-5 alkyl substituted with 1 to 5 halogens or C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl or C 1 -C 4 alkylsulfonyl or or C2-C6 alkenyl optionally substituted with 2 halogen atoms. E is a methine group or a nitrogen atom, X is oxygen, sulfur, sulfinyl or sulfonyl, Z is oxygen or sulfur, m is 1 or 2. R _x is hydrogen, halogen, C 1 -C 5 alkyl or C 1 -C 4 alkoxy, R ₂ is hydrogen, halo or C 1-4 alkoxy, R ₃ and R ₄ are independently C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkyl, or halogen, with the proviso that m is 2 when X is sulfur, sulfinyl or sulfonyl and A is also a C 3 -C 4 alkenyl group, or a basic addition salt thereof, preferably an alkali metal or amine salt thereof, provided that a) A phenylsulfonamide derivative of formula II wherein A, R 1, R ₂ , X and m are as defined above, in the presence of a base, by reaction with a N-pyrimidinyl or triazinylcarbamate derivative of general formula III wherein E, R ₃ , R ₄ , and Z are as defined above, or b) a phenylsulfonyl isocyanate or isothiocyanate derivative of formula IV wherein A, R 1, R ₃ , m, X and Z are as defined above, optionally in the presence of a base, with an amine derivative of formula V: wherein E, R ₃ and R ₄ are as defined above, or c) a phenylsulfonamide derivative of formula 11 wherein A, R ₁ , R ₃ , X and m are as defined above; -641 191,006, optionally in the presence of a base, with an isoclanate or isothiocyanate derivative of Formula VI wherein E, R ₃ , R ₄ and Z are as defined above, or d) N-phenylsulfonylcarbamate of formula (VII) wherein A, R _{1 (} R ₂ m and, X are as defined above) with an amine of formula (V) wherein E , R ₃ , R ₄ and Z are as defined above, and optionally the resulting sulfonylurea derivative of formula (I) is converted into a basic addition salt in a known manner.