CS224000B2 - Herbicide means and means for suppressing the growth of plants and method of making the active substance - Google Patents

Description

The present invention relates to a herbicidal composition and a plant growth inhibiting composition which contains as active ingredient the novel N-phenylsulfonyl-N'-pyrimidinyl- and -triazinylureas. The invention further relates to a process for the production of these novel herbicidally active and plant-regulating compounds, as well as their use for controlling weeds, in particular selective weed control in crops of useful plants or for regulating and controlling plant growth. In addition, the invention relates to novel phenylsulfonamides which are obtained as intermediates.

N-phenylsulfonyl-N'-pyrimidinyl- and -triazinylureas correspond to the general formula I ^{R 1} SO.-NH-C-NH-Z% · ft / V, i _(i) in which:

A is halogen, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkoxy, C 1 -C 4 haloalkylthio (C 4 -C 4), (C 1 -C 4) haloalkylsulfinyl or (C 1 -C 4) haloalkylsulfonyl, substituted (C 1 -C 6) alkyl or optionally substituted (C 2 -C 6) alkenyl by the above substituents,

E represents a methine group or nitrogen,

224900 2

X is oxygen, sulfur, sulfinyl or sulfonyl,

Z is oxygen or sulfur, m is 1 or 2,

R ₁ represents hydrogen, halogen, C 1 -C 5 alkyl, C 2 -C 5 alkenyl or the radical -YR 6,

R 1 is hydrogen, halogen, C 1 -C 5 alkyl, C 2 -C 5 alkenyl, C 1 -C 4 haloalkyl, or -Y-R 8, -COOR 9, -NOg or -CO-NR ? -Rg,

R ^ and R ^ are each independently hydrogen, (C 4-C alky) alkyl, (C,-C alko) alkoxy, (C až-Cth) alkylthio, (C a-C halogen) haloalkyl, halogen or (C a-C a) alkoxyalkyl; not more than 4 carbon atoms,

R 8 and R 8 are C 1 -C 5 alkyl, C 2 -C 5 alkenyl or C 2 -C 6 alkynyl,

R? and R 8 are independently hydrogen, C 1 -C 5 alkyl, C 2 -C 5 alkenyl or C 2 -C 6 alkynyl and

Y represents oxygen, sulfur, a sulfinyl or sulfonyl bridge, and also includes salts thereof.

Urea, triazine and pyrimidine derivatives having a herbicidal action are generally known.

Recently, arylsulfamoylheterocyclylaminocarbamoyl derivatives having a herbicidal activity and the ability to control plant growth have been described, for example, in European Patent Publication No. 1514, 1515, U.S. Patent No. 4,127,405, DOS 2,715,786 or French Patent 6,168,747 .

In the definitions, alkyl means straight or branched alkyl such as methyl, ethyl, n-propyl, isopropyl, four isomers of butyl, n-amyl, isoamyl, 2-amyl, 3-amyl, n-hexyl or isohexyl.

Alkoxy means: methoxy, ethoxy, n-propyloxy, isopropyloxy and the four isomers of butyloxy, in particular methoxy, ethoxy or even sopropoxy.

Examples of alkylthio include methylthio, ethylthio, n-propylthio, isopropylthio and n-butylthio, but especially methylthio and ethylthio.

Examples of alkenyl groups include vinyl, allyl, isopropenyl, 1-propenyl,

1-butenyl, 2-butenyl, 3-butenyl, 1-isobutenyl, 2-isobutenyl, 1-pentenyl, 2-pentenyl, 3- ... pentenyl and 4-pentenyl, in particular vinyl, allyl and 4-pentenyl .

Examples of alkylsulfinyl groups include methylsulfinyl, ethylsulfinyl, n-propylsulfinyl and n-butylsulfinyl, but especially methylsulfinyl and ethylsulfinyl.

Examples of alkylsulfonyl groups include methylsulfonyl, ethylsulfonyl, n-propylsulfonyl and n-butylsulfonyl groups, in particular methylsulfonyl and ethylsulfonyl groups.

Halogen means A, R ^ to R ^ as well as haloalkyl, haloalkoxy, haloalkylsulfinyl, haloalkylsulfonyl and haloalkylthio groups, but preferably fluoro and chloro.

For the purposes of A, substituted alkyl or alkenyl radicals are those which contain one or more of said substituents, preferably one substituent. In the substitution of halogen atoms, preferably more hydrogen atoms or even all hydrogen atoms of the alkyl or alkenyl radicals are replaced by halogen atoms.

The invention also includes salts which may form compounds of formula I with amines, alkali metals or alkaline earth metals or quaternary ammonium bases.

Alkali metal hydroxides and alkaline earth metal hydroxides as salt-forming components are preferably hydroxides of lithium, sodium, potassium, magnesium or calcium, in particular sodium or potassium.

Examples of amines suitable for salt formation include primary, secondary and tertiary aliphatic and aromatic amines such as methylamine, ethylamine, propylamine, isopropylamine, four isomeric butylamines, dimethylamine, diethylamine, diethanolamine, dipropylamine, diisopropylamine, di-n- butylamine, pyrrolidine, piperidine, morpholine, trimethylamine, triethylamine, tripropylamine, quinuclidine, pyridine, quinoline and isoquinoline, in particular ethylamine, propylamine, diethylamine or triethylamine, in particular isopropylamine and diethanolamine.

Examples of quaternary ammonium bases are, in general, cations of halogenammonium salts, for example tetramethylammonium, trimethylbenzylammonium, triethylbenzylammonium, tetraethylammonium, trimethylethylammonium, but also ammonium.

The compounds of formula I can be divided into two larger subgroups. These groups consist of compounds of formula (1), in which A stands for

AND

1. C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, al (C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkoxy, C 1 -C 4 haloalkylthio (C-C halogen) alkyl, (C až-C 1) haloalkylsulphinyl or (C až-C halogen) haloalkylsulphinyl, substituted (C až-C alky) alkyl group, optionally substituted by C, až-C alk alk alkenyl group or (C 2-C halogen) haloalkenyl; up to 6 carbon atoms;

AND

2. C 1 -C 6 haloalkyl;

Within the group,. are preferred compounds in which

a) Z is oxygen

b) the radicals R 1 ^{and R} 4 together do not contain more than 4 carbon atoms.

’I

Group 1a) may be subdivided into two further subgroups consisting of compounds in which aa) m is the number 1 and ab) and is the number 2, i

Among the group 1aa), those compounds in which the -X-A residue is in the 2-position or the 3-position to the sulfonyl radical are preferred.

Among the group Iab), a preferred group consists of compounds in which both the -X-A radicals are in the 2-position and in the 5-position to the sulfonyl group.

A greater advantage of the compounds of the above-mentioned subgroups of groups 1aa) and 1b) is that the radicals R @ 1 and R @ 4 together contain at most 4 carbon atoms. Accordingly, there are particularly advantageous groups of compounds in that only one -X-A radical in the 2-position of the sulfonyl radical is present in the compounds of formula I • and b),

Z ¹ represents oxygen and the radicals R and R together contain no more than 4 carbon atoms, AI

a and b) two -X-A residues are present at the 2-position and at the 5-position to the sulfonyl residue;

Z is oxygen and the radicals R @ 1 and R @ 2 together contain no more than 4 carbon atoms.

Among the groups a and b), compounds in which R 1 is preferred is hydrogen and the radical R ₂ is in position 5 or 6 sulfonyl group.

Among these groups, those in which R @ ₂ is hydrogen, halogen, C1 -C4 alkoxy, nitro or COOR @ 8 are again preferred.

Further preferences within the latter group are those wherein R ₂ is hydrogen, fluoro, nitro or C 1 -C 4 alkoxy and R 1 and R 2 are hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkyl. C 1 -C 4 alkylthio, C 1 -C 4 alkylthio, halogen or alkoxyalkyl, wherein R 4 and R 4 together contain at most 4 carbon atoms.

Of these compounds, those in which R @ ₂ is hydrogen and R @ ₄ and R @ ₄ are C1 -C4 alkyl, C1 -C4 alkoxy, methylthio, halogen or alkoxyalkyl are again preferred.

Further preferences within the latter group are those in which X is oxygen or sulfur.

Of these, particularly preferred are those in which A is C 2 -C 8 alkoxyalkyl, C 2 -C 4 haloalkenyl or C 2 -C 6 alkenyl.

Three other of the last group of preferred subgroups are groups of compounds in which

(a) A represents a (C 2 -C 8) alkoxyalkyl group and and R 6 represents a methyl group, an ethyl group, a chlorine or a methoxy group,

β) A represents a (C 2 -C 6) alkenyl group and R 2 and R 2 are methyl, ethyl, chlorine or methoxy; and

v) A is a vinyl group substituted with one to three halogen atoms and R 1 and R 2 are methyl, ethyl, chlorine or methoxy.

Among the compounds of formula I in which Z is sulfur, those in which X is oxygen or are preferred. sulfur, R ^ and R ^ are each independently an alkyl group having 1-3 carbon atoms, alkoxy having 1 to 3 carbon atoms or alkylthio of 1 to 3 carbon atoms, together with a maximum of 4 carbon atoms and A represents -CH ₂ - CH = CH ₂ , -CH ₃ -CH ₂ = CH-CH ₃ , -CH ₂ -CH (CH ₃ ) = CH ₂ , methoxyethyl, methoxymethyl or -CCl = CHCl and -XA occupies the position 2 and m represents a number 1.

Preferred individual compounds include:

N- (2-allyloxyphenylsulfonyl) -N '- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) urea.

Within Group 2, those compounds in which

a) the -X-A substituent is in the 2- or 3-position of the phenyl ring,

b) only one -X-A substituent is present at the 2-position of the phenyl core,

δ) R 1 and R ₂ are hydrogen and

d) the radicals R @ 1 and R @ 4 each independently contain at most 2 carbon atoms.

Particular preference is given to compounds of the group 2v which contain only one substituent -XA which is in the 2-position of the phenyl core and in which the radicals 8-4 each independently contain at most 2 carbon atoms and R 1 and R ₂ are hydrogen.

However, particularly preferred of the latter are those in which the radicals R1 and R1 are independently methyl or methoxy.

Such a group is a compound of formula I wherein R, e and R ₂ are hydrogen, X and Z are oxygen, E is nitrogen, R 1 is methoxy, R 1 is methyl or methoxy and A is difluoromethyl and the radical -XA occupies the position 2 on the phenyl ring, wherein X may also be sulfur when R 1 is methyl.

Such individual compounds are:

N- (2-Difluoromethoxyphenylsulfonyl) -N (4,6-dimethoxy-1,3,5-triazin-2-yl) urea

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

N- (2-difluoromethylthiophenylsulfonyl) -N (4-methyl-6-methoxy-1,3,5-triazin-2-yl) urea,

N- [2,2- (1,1,2,2-tetrafluoroethoxy) fenylsulfonylj-N ^/ - (4-methyl-6-methoxy-1,3,5-triazin-2-yl) -urea,

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

N- (2-Trifluoromethoxyphenylsulfonyl) -N '- (4-methyl-6-methoxypyrirtidin-2-yl) urea,

N- (6-chloro-2-difluoromethoxyphenylsulfonyl) -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.

Another sub-group of Group 2 consists of compounds of formula I wherein A is a haloalkyl group having 1 to 6 carbon atoms and m is 2 when A is -CHF ₂ , -CF _3> -CH ₂ -CF ₃ , -CF ₂ CHF _2, CHFCl--cfg, -CFgCHFBr or -cfg-CHF-CFjj R ₃ represents -OCH ₃ or CH _3> R is OCH, -CH _3, -OCgH ^,-CH₂-O- CH or _-CH2- -CHgOCHj and the phenyl ring is unsubstituted or substituted in position 2, 3, 5 or 6 sulfonyl group, only one long substituent from the group consisting of fluorine, chlorine, bromine or methyl.

Of the compounds of this subgroup 2.1, those in which

(a) Z represents oxygen; and

b) both R ₃ and R 6 together do not contain more than 4 carbon atoms.

Group 2.1a) may be divided into two further subgroups consisting of compounds in which aa) m is one and b) m is two.

Among the group 2.1aa), those compounds in which the -X-A radical is in the 2-position or the 3-position to the sulfonyl group are preferred, among which those in which zyty -X-A is in the 2-position are further preferred.

Among group 2.1ab), a preferred group is that in which both the -X-A radicals are in the 2-position and in the 5-position to the sulfonyl group.

A further advantage of the compounds of the above-mentioned subgroups of groups 2.1aa) and 2.1ab) is that the radicals R ₃ and R 6 together contain at most 4 carbon atoms. Thereby, there are particularly advantageous groups of compounds in that only one -XA radical in the 2-position of the sulfonyl group and the radicals R @ 1 and R @ 2 are present in the compounds of formula I and b).

H 2 together contain no more than 4 carbon atoms and abb) two -X-A residues are present at the 2-position and at the 5-position to the sulfonyl residue and the residues

B 3 and R 6 contain no more than 4 carbon atoms.

Group 2 1abb _T) are further preferred are those compounds in which A represents a group -CH1 * _2, or -CF -CHgCHgCl.

From the group 2.1aab) are preferred those compounds in which _R1 is hydrogen, and the rest of Hg is in the 5-position or 6-position to the sulfonyl group.

Of these compounds, preferred are in turn those compounds in which R ₂ represents hydrogen, fluoro, nitro or-COOR.

Further preferences within the latter group are compounds wherein X is oxygen or sulfur.

Of these, particularly preferred are those in which both R 1 and R 8 are hydrogen, R 6 is chloro, fluoro, methyl, chloromethyl, alkoxy, isopropyloxy, ethyl, or methoxy, and R 6 is methyl, ethyl, methoxy or ethoxy.

Two other preferred subgroups of the last group are the groups of compounds in which

a), the bridging member X is oxygen; and f) the radical A is represented by -CFgG in which O is hydrogen, fluoro, chloro, bromo, trifluoromethyl or methyl.

Within group f1), those compounds in which G is fluoro, bromo or trifluoromethyl are preferred.

Equally preferred positions as in groups (e) and (i) are those in which A is -CHgF, -CHgCHgCl or -CHgCHgF.

Among the compounds of formula I in which Z is sulfur, those in which X is oxygen or sulfur and R @ 1 and R @ 4 are each independently C1 -C4 alkyl, C1 -C4 alkoxy are preferred. or C1-C4alkylthio together with not more than 4 carbon atoms and A is -CHFg, -CF4, -CgF4 or -CFg-CHFg, and -XA occupies position 2.

Preferred individual compounds include:

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

N- (2-difluoromethoxyphenylsulfonyl) -N '- (4,6-diethoxy-1,3,5-triazin-2-yl) urea,

N- 2-difluoromethoxyphenylsulfonyl-N '- (4-chloro-6-methylpyrimidin-2-yl) urea,

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

N- (2-difluoromethylthiophenylsulfonyl-N '- (4-chloro-6-methoxypyrimidin-2-yl) urea),

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

N- (2-difluoromethoxyphenylsulfonyl) -N '- (4-methoxy-6-isopropyloxy-1,3,5-triazin-2-yl) urea,

N- (2-difluoromethylthiophenylsulfonyl) -N '- (4-ethyl-6-methoxy-1,3,5-triezin-2-yl) urea; and

N- (2-difluoromethoxyphenylsulfonyl) -N '- (4-chloro-6-methoxypyrimidin-2-yl) urea.

The preparation of the compounds of formula I is carried out in an inert, organic solvent.

According to a first process, compounds of formula I are obtained by reacting a phenylsulfonamide of formula II (II) (X-A) wherein:

A, R ₁ , R ₂ and X and m have the meanings given in formula I, in the presence of a base with an N-pyrimidinyl or -triazinylcarhamate of the formula III

(III) in which:

E, Ry, and Z are as defined in Formula I.

According to a second process of the present invention, the compounds of the formula I are obtained by reacting the phenylsulfonyl isocyanate or the isothiocyanate of the formula IV '(IX-A),

SO 4 N = C = Z (IV) in which

A, R 1, R g, m, X, and Z have the meanings given in formula I, optionally in the presence of a base, react with an amine of the formula V ^H from ^N = <(n

N— <

in which E, R1 and R1 have the meanings given in formula I, at temperatures between -20 and +120 [deg.] C. and the compound obtained is converted, if appropriate, by treatment with an amine, alkali metal or alkaline earth metal hydroxide or quaternary ammonium base .

In another process, compounds of formula I are prepared by reacting a sulfonamide of the above formula II, optionally in the presence of a base, with an isocyanate or isothiocyanate of formula VI

N- (R = C = N- ⁾

(VI)

E, R1, R1 and Z are as defined in formula I.

Finally, the compounds of formula I can also be obtained by providing the carbonate of formula VII ₀

-SO 2 NH is reacted with N-phenylsulfonyl (VII) wherein

A, R 1, R g, m and X are as defined in formula I, with the amine of the above formula V,

The resulting ureas of the formula I can optionally be converted into basic editing salts by treatment with amines, alkali metal hydroxides or alkaline earth metal hydroxides or quaternary ammonium bases. This is accomplished, for example, by reaction with an equimolar amount of the base and evaporation of the solvent.

The starting materials of formulas II, IV and VII are partly new and can be prepared according to the following methods:

The novel sulfonamides of the formula II which are used as intermediates are obtained from the corresponding anilines by diazotization and exchange of the diazo group with sulfur dioxide in the presence of a catalyst such as cuprous chloride in hydrochloric acid or acetic acid and reaction of the resulting phenylsulfonyl chloride with ammonium hydroxide solution.

The compounds of formula II can also be obtained by O-alkylation or S-alkylation respectively. by alkenylation of hydroxy- or thiophenylsulfonamides with the corresponding halides and resp. esters of sulfuric acid or by reaction of ortho-halo-phenylsulfonamides with metal alkoxides resp. with mercaptides and, optionally, oxidation thereof, e.g. peracids to form the corresponding sulfoxides and sulfones.

Ortho-substituted hydroxyphenylsulfonamides resp. substituted ortho-hydroxyphenylsulfonamides of the general formula (VIII) with ₂ nw ₂

VIII-Η (VIII) in which

R 1 and R g have the meanings given in formula I a

X 'is oxygen or sulfur as starting materials of certain sulfonamides of formula II, with the exception of ortho-hydroxyphenylsulfonamide. They can be obtained by cleavage of the ether of the corresponding C 1 -C 4 alkoxyphenylsulfonamides. boron halides (such reactions are described in U.S. Pat. No. 3,904,680 and in J. Am. Chem. Soc. 64. 1 128 (1942)) or by hydrogenolysis of the corresponding benzyloxyphenylsulfonamides as described in J. Chem. Soc. 1958. 2 903.

The alkoxyphenylsulfonamides can then be recovered from the corresponding alkoxyanilides, as mentioned above, or by chlorosulfonation of the alkoxybenzenes and reaction of the obtained phenylsulfonyl chlorides with an ammonium hydroxide solution. Such reactions are known from 0. Am. Chem. Soc. € 2. 603 (1940).

The compounds of formulas II and VIII which are used as intermediates are novel and novel compounds, respectively. They are in part new and specially developed for the synthesis of compounds of formula I. These intermediates constitute a further object of the present invention.

The phenylsulfonyl isocyanates of the formula IV can be obtained by reacting the sulfonamides of the formula II with phosgene in the presence of butyl isocyanate in a chlorinated hydrocarbon solvent at reflux temperature. Similar methods of preparation are described in Newer Methods of Preparative Organic Chemistry, Vol. VI, 223-241, Academic Press New York and London.

The isothiocyanates of formula IV are obtained by reacting the sulfonamides of formula II with carbon disulfide and potassium hydroxide followed by the reaction of the dipotassium salt with phosgene. Such procedures are described in Arch. Pharm. 299. 174 (1966).

The N-phenylsulfonylcarbamates of formula VII are obtained by reacting the sulfonamides of formula II with diphenylcarbamate in the presence of a base. Similar procedures are disclosed in Japanese Patent Specification No. 61,169.

The starting materials of formulas III, V and VI are known or can be prepared according to known methods.

By reacting the amines of formula V with oxalyl chloride in chlorinated hydrocarbons as a solvent, isocyanates of formula VI can be prepared. The amines of formula V are known and in part can be obtained commercially or can be prepared by known methods. See The Chemistry of Heterocylic Compounds, Vol. XIV, Interscience Publishers, New York, London.

These reactions leading to the compounds of formula I are carried out preferably in aprotic, inert, organic solvents such as methylene chloride, tetrahydrofuran, acetonitrile, dioxane and toluene.

The reaction temperatures are preferably between -20 ° and +120 ° C. These reactions generally proceed slightly exothermally and can be carried out at room temperature. In order to shorten the reaction time or also to start the reaction, the reaction mixture is expediently heated to the boiling point for a short time. The reaction times can also be reduced by adding a few drops of base or isocyanate as reaction catalyst.

The final products can be isolated by concentration and / or evaporation of the solvent and purified by recrystallization or trituration of the solid residue in solvents in which the reaction products do not dissolve well, such as ether, aromatic hydrocarbons or chlorinated hydrocarbons.

The active compounds of the formula I are stable compounds. Handling them does not require any special measures.

The compounds of the formula I have a considerable ability to control the growth of plants, in particular they have the ability to inhibit (limit) the growth of plants. These compounds inhibit the growth of both monocotyledonous and dicotyledonous plants.

Thus, for example, leguminous crops often grown as cover crops in the field of tropical landscaping can be selectively suppressed by the action of the compounds of formula (I) in order to prevent soil erosion between the crop plants, but Soil (cover crops) did not compete with the growth of cultural plants.

Furthermore, the compounds of the formula I are suitable for preventing the germination of stored potatoes. Potatoes often develop germs during storage during winter, resulting in shrinkage, weight loss and rot.

At higher rates of application, all test plants are damaged in their development to the extent that they die.

At low rates of application, the compounds of formula I exhibit good selective growth inhibition properties and good selective herbicidal properties which make them ideally suited for use in crop plants, particularly cereals, cotton, soybean, corn and rice. This also partially damages the weeds, which until then could only be destroyed with total herbicides.

224000 10

The type of action of these active substances is unusual. Numerous of them are translocable, i. they are taken by the plant and transported to other places where their effect is then applied. It is unusual for the active substances to reach the leaves not only through the bundles of blood vessels in the wood part, from the roots, but can also be transported through the tissue in the bast part from the leaves back to the roots. Thus, for example, surface treatment can damage perennial weeds up to the roots. The new compounds of formula I already act - in comparison with other herbicides and growth regulators - at very low rates of application.

The invention also relates to herbicidal and plant growth regulating compositions containing at least one active compound of the formula I as well as to a method for controlling weeds in pre-emergence and post-emergence application, and to a method of controlling the growth of monocotyledonous and dicotyledonous plants, especially grasses, tropical intercultures. for covering soil and tobacco shoots.

The compounds of formula I are used in unchanged formulations together with the usual excipients which are used in formulating such formulations and are therefore processed, for example, into emulsion concentrates, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granules, also encapsulated in, for example, polymeric substances in a known manner. The methods of application, such as spraying, fogging, sprinkling or potting, are selected accordingly, as well as the type of composition, according to the intended objectives and proportions.

Compositions containing the active compound of the formula I and optionally a solid or liquid additive and concentrates or other preparations of this type are prepared in a known manner, for example by thoroughly mixing and / or grinding the active compounds with fillers, such as solvents, solid carriers and optionally surface active compounds (surfactants).

Suitable solvents are: aromatic hydrocarbons, preferably C8-C12 fractions, such as mixtures of xylenes or substituted naphthalenes, phthalic acid esters such as dibutyl phthalate or dioctyl phthalate, aliphatic hydrocarbons such as cyclohexane or paraffinic hydrocarbons, alcohols and glycols, and their ethers and esters, such as ethanol, ethylene glycol, ethylene glycol monomethyl ether, or ethylene glycol monoethyl ether, ketones such as cyclohexanone, strongly polar solvents such as N-methyl-2-pyrrolidone, dimethylsulfoxide or dimethylformamide, as well as optionally epoxidized vegetable oils such as epoxidized coconut oil or soybean oil, or water

As solid carriers, for example for dusts and dispersible powders, natural stone flours such as limestone, talc, kaolin, montmorillonite or attapulgite are generally used. Highly disperse silicic acid or highly disperse absorbent polymers may be added to improve physical properties. Suitable granular adsorptive carriers for the granulates are porous types, such as pumice, brick ground, sepiolite or bentonite, and non-sorptive carrier materials, for example limestone or sand. In addition, a large number of pre-granulated materials of inorganic or organic origin, such as in particular dolomite or comminuted plant residues, may be used.

Suitable surfactants are nonionic, cationic and / or anionic surfactants with good emulsifying properties, dispersing properties and wetting properties. Surfactants are also understood as meaning mixtures of surfactants.

Suitable anionic surfactants can be both water-soluble soaps and water-soluble synthetic surfactants.

Soaps include alkali metal, alkaline earth metal, or the corresponding optionally substituted ammonium salts of higher fatty acids (C 10 -C 22), such as sodium or potassium salts of oleic acid or stearic acid, or mixtures of natural fatty acids which are obtained, for example, from coconut oil or tallow oil. The fatty acid salts of methyl taurine must also be mentioned.

However, so-called synthetic surfactants are used more frequently, especially fatty sulfonates, fatty sulfates, sulfonated benzimidazole derivatives or alkylarylsulfonates.

Fatty sulfonates or fatty sulfates generally exist as alkali metal, alkaline earth metal or optionally substituted ammonium salts and contain an alkyl radical of 8 to 22 carbon atoms, the alkyl also including an alkyl portion of acylated radicals such as sodium or potassium salt ligninsulfonic acids, dodecylsulfuric acid ester or a mixture of sulfated fatty alcohols made from natural fatty acids. Also included are salts of sulfuric acid esters and sulfonic acids of fatty alcohol adducts with ethylene oxide. The sulfonated benziimidazole derivatives preferably contain 2 sulfo groups and a fatty acid radical of 8 to 22 carbon atoms. Alkylarylsulfonates are, for example, the sodium, calcium or triethanolammonium salts of dodecylbenzenesulfonic acid, dibutylnaphthalenesulfonic acid or the naphthalenesulfonic acid-formaldehyde condensation product.

suitable phosphates, such as, for example, the phosphoric acid ester salts of the p-nonylphenol adduct with ethylene oxide (4 to 14) are also suitable.

Suitable nonionic surfactants are derivatives of polyglycol ether of aliphatic or cycloaliphatic alcohols, saturated or unsaturated fatty acids and alkylphenols, which may contain 3 to 30 glycol ether groups and 8 to 20 carbon atoms in the (aliphatic) hydrocarbon radical and 6 to 18 carbon atoms in the alkyl the remainder of the alkylphenols.

Other suitable nonionic surfactants are the water-soluble adducts of polyethylene oxide with polypropylene glycol, ethylenediaminopropylpropylene glycol and an alkylpolypropylene glycol of 1 to 10 carbon atoms in the alkyl chain containing 20 to 250 ethylene glycol ether groups and 10 to 100 propylene glycol ether groups. These compounds usually contain from 1 to 5 units of ethylene glycol per propylene glycol unit.

Examples of non-ionic surfactants include nonylphenol polyethoxyethanols, castor oil polyglycol ethers, polypropylene adducts with polyethylene oxide, tributylphenoxypolyethoxyethanol, polyethylene glycol and octylphenoxypolyethoxyethanol.

Also suitable are fatty acid esters derived from polyoxyethylene sorbitan, such as polyoxyethylene sorbitan trioleate.

The cationic surfactants are in particular quaternary ammonium salts which contain, as a substituent on the nitrogen atom, at least one alkyl radical of 8 to 22 carbon atoms and which contain, as further substituents, lower or halogenated alkyl radicals, benzyl radicals or lower hydroxyalkyl radicals. These salts are preferably in the form of halides, methylsulfates or ethylsulfates, for example, stearyltrimethylammonium chloride or benzyl-di- (2-chloroethyl) ethylemonium bromide.

Surfactants useful in the manufacture of the compositions of the present invention are described, inter alia, in the following publications:

Mc Cutcheon &apos; s Detergents and Emulsifiers Annual MC Publishing Corp., Ringwood, New Jersey, 1979.

Sisaly and Vood, Encyclopedia of Surface Active Agents, Chemical Publishing Co., Inc.

Kew York, 1964.

The active substance content of commercially available pesticidal compositions is between 0.1 and 95% (by weight, preferably between 1 and 80% by weight). Furthermore, they contain 1 to 99.9% of a solid or liquid additive and 0 to 25%, in particular 0, 1 to 25% of a surfactant.

Preferred compositions are formulated, in particular, in the following composition (percentages with a minimum weight percent):

Solutions:

active ingredient: solvent: surfactant

Emulsifiable concentrates:

active ingredient: surfactant liquid carrier:

to 30 56, 99 to 0, 6 to 0 to 56, preferably 5 to 20%, preferably 95 to 0%, preferably 0 to 95% to 20%, preferably 5 to 10% to 30 56, preferably 10 to 20% 50 to 94 preferably 70 to 85%.

Dust:

active ingredient: solid carrier:

0.1 to 10 56, preferably 0.1 to 15 56 99.9 to 90 56, preferably 99.9 to 99 56. ·

Suspension concentrates:

active ingredient: water:

surfactant:

Wettable powder:

active active flight: coated active substance: solid carrier:

up to 75%, preferably 10 to 50 56 94 to 25%, preferably 90 to 30 56 1 to 40%, preferably 2 to 30 56.

0.5 to 90 56, preferably 1 to 80% and 0.5 to 20 56, preferably 1 to 15 * to 95, preferably 15 to 90 56.

Granulates:

active ingredient: solid carrier:

0.5 to 30 56, preferably 3 to 15% 99.5 to 70 56, preferably 97 to 85%.

While commercially available formulations are preferably concentrated formulations, generally dilute formulations are used for the final use. The dosage forms can be diluted to a concentration of 0.001% of active ingredient. The application rates are generally 0.01 to 10 kg / ha, preferably 0.025 to 5 kg / ha.

These compositions may also contain other additives such as stabilizers, anti-foaming agents, viscosity regulators, binders, adhesives, as well as fertilizers or other active substances to achieve particular effects.

In the following examples, temperatures are given in degrees Celsius and pressures in Pa.

Examples illustrating the method of production of active ingredients:

Example 1

2-hydroxyphenylsulfonamide

To a suspension of 2-methoxyphenylsulfonamide (39 g) in absolute methylene chloride (210 ml) was added dropwise boron tribromide (22.2 ml) under nitrogen at room temperature over 15 minutes. The reaction mixture was then stirred at room temperature for 1 hour. Then, to the reaction mixture cooled to 0 ° C, 200 ml of ethanol are added over 15 minutes and the clear solution is evaporated. The oily residue is taken up in ethyl acetate, washed twice with water, dried over sodium sulphate and evaporated. Trituration of the residue with petroleum ether gave 25.1 g of 2-hydroxyphenylsulfonamide, m.p. 136-138 ° C.

The hydroxyphenylsulfonamides of the formula IIIa are obtained in an analogous manner and are summarized in the following Table 1:

Table

OH

^R , ^R 2 Position -OH Physical data / ^CH 3 5-CH = CH • ₃ H 2 mp 90-91 ° _2-CH3 H 5 2-C1 H 5 5-F H 2 t 141 to 142 ° 5-Br H 2 T. 169 to 170 ° 5-NO ₂ H 2 t. t 180 to 185 ° 3-CH ₃ H • 2 133 to 134 ° 2-CH, H 3 3-C1 H 2 _6-CH3 H 2 3-0CH ₃ H 2 2-XH ₃ H 3 3-CH ₃ 5-C ₄ H ₉ 2 134 to 137 ° 6-OCH ₃ H 2 6-OH H 2 5-OCH ₃ H 2 J19 to 120 ° 2-0CH ₃ H 5 T. 213 to 215 ° 5-CH ₃ 6- C1 H H 2 2 T. 155 T. 190 to 156 ° to 191 ° 3-NO ₂ H 2 3-cooch ₂ 5-cooch ₂ H H 2 2 t 171 to 172 ° 5-C1 H 2 T. 176 to 179 ° 5-NO ₂ 3-CF, 2 5-NOg 3-C1 2 5-CF ₃ 3-no ₂ 2 5-CH, 3-CH ₃ 2 5-C1 3-NO ₂ 2

Table 1 - continued «1 r ₂ Position -OH Physical data

5-01 3-01 2 t. t. 156 8Ž 158 ' 5-Br 2-0CH ₃ 2 5-Br 2-OCH ₃ 3 t. t. 194 to 197 ' 3-OCH ₃ 5-cooch ₄ 2 2-0CH ₃ 5-COOCH ₃ 3 _5-CH3 3-Br 2 5-Br 3-NO ₂ 2 5-Br 3-COOCH 2 5-COOCH ₃ 3-NO ₂ 2 5-01 3-Br 2 t. t. 247 to 249 ' 3 -NH ₂ H 2 _5-NH2 H 2 s-cooC (H) .d) 3-NO ₂ 2 5-CO 2 (CH ₂ ) ₂ H 2 6-HOg H 2 e-C00CH ₃ H 2

Example 2

2-Allyloxyphenylsulfonamide

A mixture of 3.5 g of 2-hydroxyphenylsulfonamide, 5.5 g of potassium carbonate and 1.7 ml of allyl bromide was stirred in 100 ml of methyl ethyl ketone under nitrogen at reflux for 1 hour. The reaction mixture was cooled to room temperature, filtered ee and the filtrate ee evaporated. Single recrystallization from ethyl acetate gave 3.27 g of 2-ellyloxyphenylsulfonamide, m.p. 104-105 ° C.

Analogously, the sulfonamides of the formula II can be prepared as shown in the following table:

Table 2 so, -nw _£

* 1 r ₂ X AND Position X-A Physical data H H O -CCl = CHCl 2 mp 147-149 ° H H Sat -Cl = CHCl 2 H H Sat -CCl = CHCl 2 H H SO ₂ - <3 Cl = CHCl 2 H H 0 -ch = cci ₂ 2 H H with -ch = cci ₂ 2 H H Sat -ch = cci ₂ 2 H H SO ₂ -ch = cci ₂ 2 H H 0 -ch ₂ ch = ch ₂ 2 mp 104-105 °

Position of the data

X-A

Table 2 - continued r ₂ xa

H H WITH -ch _? ch = ch ₂ 2 H H 0 CH 13 -CH ₂ -C =CH ₂ 2 mp 104-105 ° CH, ¹³ H H with -CH ₂ -C = CH ₂ 2 H H 0 - (CH ₂ ) ₂ -CH = CH ₂ 2 H H 0 - (CH _{2) 3} -CH = CH ₂ C ^H -CH 3, -CH = C 2 H H 0 2 and: H with ^CH 3 -ch ₂ -ch = c 2 H H 0 ' -CH ₂ -CH = CH-CH ₃ 2 mp 113-114 ° H H with -ch ₂ -ch = ch-ch. 2 H H 0 oh ₃ -CH 2 CH = CH ₂ 2 H H with X ^CH 3 -CH 1 ^x -ch = ch ₂ 2 H H 0 -CH ₂ -OCH ₃ 2 decomposition from 121 ° H H 0 -CH ₂ -0C ₂ H _5, -CH ₂ -S-CH ₃ -0Η 0Η _{2 2 3} -00Η 2 H, H H H 0 0 2 2 mp 110-112 ° H H with -CH ₂ CH ₂ -OCH ₃ 2 H H 0 -CH ₂ CH ₂ -OC ₂ H ₅ 2 H 6-C1 H H 0 0 -CH ₂ CH ₂ -SCH ₃ -ch ₂ ch = ch ₂ 2 2 mp 127-128 ° CH, ¹³ 6-C1 H 0 -CH ₂ -C = CH ₂ 2 6-C1 H 0 ch ₃ -ch ₂ -ch = c ^{X 5} CH ₃ 2 6-C1 6-01 H H 0 0 -CH ₂ OCH ₃ - (CH ₂ ) ₂ OCH ₃ 2 2 6-C1 H 0 -CH ₂ SCH ₃ 2 6-C1 AT 0 - (CH ₂ ) ₂ SCH 3 2 6-C1 H 0 -CH ₂ -CH = CH-CH ₃ 2 6-OCH-j H 0 -ch ₂ -ch = ch ₂ 2

Position of physical data

X-A

Table 2 - continued

R ₂ X A '

CH,

6-OCHj

6-OCH,

-ch ₂ -c = ch ₂

- (ch ₂ ) ₂ -oc ₂ h ₅

6-OCH,

-ch ₂ -ch = c.

X ^CH 3 • CH,

6-QCH ₃

6-CH,

- (ch ₂ ) ₂ -ch = ch ₂

-CH ₂ -CH = CH ₂

CH,

6-CH,

-ch ₂ -c = ch ₂

_6-CH3

_6-CH3

H

6-NO ₂

6-NO ₂

6-NO ₂

6-KO,

6-NO ₂

6-cooch ₂

5-C1

- (ch ₂ ) ₂ -och ₃

-ch ₂ sch ₃

-ch ₂ ch ₂ -och ₂ ch = ch ₂

-ch ₂ -ch = ch ₂

-CH ₂ -CH = CH-CH ₃

-CH ₂ -OCH ₃

-CH ₂ -CH ₂ -OC ₂ H ₅

CH,

I ³

-CH ₂ -C = CH ₂

-ch ₂ -ch = ch ₂

-ch ₂ -ch = ch ₂

t 122

5-C1 '3

-CH ₂ -C = CH ₂

CH,

5-Br

-ch ₂ -c = ch ₂

5-Br

5-Br

5-F

-ch ₂ -ch = ch ₂

-ch ₂ -och ₃

-ch ₂ -ch = ch ₂

t10 to 1

113-1 .CH,

5-F

-ch ₂ -ch = c

CH,

CH, .CH,

5-CH • CH,

-ch ₂ -ch = c

CH,

-CH,

5-CH

-ch ₂ -ch = ch ₂ oil

ΌΗ,

Table 2 - continued

^S 1 r ₂ X @ 1 ^CH3 5-CH H 0 _5-CH3 H 0 _5-CH3 H 0 _5-CH3 H 0 5-NO ₂ H 0 5-NO ₂ H 0 5-NO ₂ H. 0 5-OCH ₃ H 0

A Location

X-A physical data

5-OCH ₃ H 0 5-OCH ₃ H 0 5-OCH ₃ H 0 5-OCH ₃ H 0 CH ₃ 5-CON H 0

5-CON H O

5-COOCH ₃ H 0 5-COOCH ₃ H 0 5-COOCH ₃ H 0 5-NO ₂ 3-CF ₃ 0 5-NO ₂ 3-Cl 0

5-NO ₂ 3-Cl 0 5-CF ₃ 3-NO ₂ 0 5-CH 5-CH3 3-CH ₃ 3-CH ₃ 0 0 5-C1 3-NO ₂ 0 5-C1 3-Cl 0 5-C1 3-Cl 0 5-C1 3-Cl 0 5-Br 3-OCH ₃ 0 5-Br 2-0CH ₃ 0 3-OCH ₃ 5-COOCH ₃ 0

-CH ₂ CH ₂ OCH ₃ 2

-CH ₂ CH ₂ OCH ₃ 2

-CH ₂ -CH = CH ₂ 2

-CH ₂ -CH = CH-CH ₃ 2

-CH ₂ -CH = CH-CH ₃ 2

-CH ₂ -S-CH ₃ 2

-CH ₂ CH ₂ CH 2

-CH ₂ CH ₂ CH 2

-CH ₂ -C = CH ₂ 2

-CH ₂ CH = CH-CH ₃ 2

-CH ₂ OCH ₃ '2

-CH ₂ CH ₂ -SCH ₃ 2

-CH ₂ -CH = CH ₂ 2 ^H 3

-CH ₂ -C _»2 CH 2

-CH ₂ -CH = CH ₂ 2? ^H 3

-CH ₂ -C = CH ₂ 2

-CH ₂ -OC ₂ H ₅ 2

-CH ₂ -CH = CH ₂ 2

-CH ₂ -CH = CH ₂ 2

CH, · 3

-CH ₂ -C = CH ₂ 2

-CH ₂ -CH = CH ₂ 2

-CH ₂ -CH = CH ₂ 2

-CH ₂ -CH = CH-CH ₃ 2

-CH ₂ -CH = CH-CH ₃ 2

-CH ₂ -CH = CH ₂ 2

-CH ₂ -CH ₂ -OCH ₃ 2

-CH ₂ -OCH ₃ 2

-CH ₂ -CH = CH ₂ . 2

-CH ₂ -CH = CH ₂ 3

-CH ₂ CH ₂ CH 2

m.p. 139-140 °

138 DEG-141 DEG, 88 DEG-89 DEG

161 DEG-162 DEG

Location Physical data

X-A

Table 2- continued

R ₂ XA

CH,

2-OCH ₃

5-CH 3

5-Br

5-C1

5-COOCH ₃

3-Br

3-NOg

3-Br

-CH₂-C = CH ₃

-CHg-OCH 3

-CHgCH = CHg

-CHgCH = CHg

mp 179 °

5-C1

5-C1

H

H

H

H

H

H

H

H

3-Br

3-Br

H

H

H

H

H

H

H

H ch ₃ ,

O-CHg-C = CHg

O-CHg-CHg-OCH3

SO-CHg-CH = CHg

SOg -CHg-CH = CHg

SO-CH₂-CH = _CH-CH3

SOg-CH₂-CH = _CH-CH3

_{O-CH₂-SO-CH3}

O-CHg-SOg-CH3

_{O-CH₂-CH₂-SO-CH3}

O-CHg-CHg-SOg-CH3

Cl

AND

-CHg-C = CHg

Cl

AND

-CHg-C = CH-Cl

Cl

AND

-CH 2 -CH = C-CH ₃

Cl

-CHg-CH = C

Cl

_5-CH3

5-NOg

Cl

AND

-CHg-C = CHg

Cl

AND

-CH 2 -C 1 CH-Cl

5-Br

Cl t

-CHg-C-CHg

5-C1

-CHg-CH = C

Cl

Cl

5-CH _(CH3) g

Cl

AND

-CH 2 -CH = C-CH ₃

Cl

AND

-CHg-C = CHg

Cl

-CHg-C-CHg

Table 2 - continued ^H 1 r ₂ X AND Position X-A Physical data Cl J 6-OCH ₃ H 0 -CH ₂ -C =CH-Cl 2 Cl 5-OCH ₃ AT 0 | -CH, -CH = C ^ Cl 2 Cl 6-C1 H 0 -CH ₂ -C = CH ₂ 2 Cl | 3-NOg H 0 -CH ₂ -CH = C-CH ₃ 2 3-CH ₃ 3-NO, H 0 -CH ₂ -CH = CH ₃ 2 t. 114 to 116 ° H 0 -CH ₂ -CH = CH ₃ 2 3-C1 H 0 -CH ₂ -CH = CH ₃ 2 3-C1 H 0 -CH ₂ -CH = CH-CH ₃ 2 CH, I ³ 3-C1 H 0 -CH-C = CH ₂ 2 CH, | ³ 3-OCH ₃ H 0 -ch-c = ch ₂ 2 3-0CH ₃ H 0 -ch ₂ -ch = ch ₂ 2 2-OCH ₃ H 0 -ch ₂ -ch = ch ₂ 5 t 113 to 114 °

Example 1 and d 3

a) 2-difluoromethoxyphenylsulfonyl chloride

To a solution of 6.4 g of copper sulfate in 276 ml of 36% hydrochloric acid and 72 ml of water, 101.2 g of 40% sodium bisulfite solution was added dropwise while cooling at 0 ° C. 101.2 g of a 40% sodium bisulfite solution and a solution of the diazonium salt cooled to -10 ° C are added dropwise to the solution obtained by dropwise addition of 28.8 g of sodium nitrite in 44 ml of water while cooling to a solution of 39 ml of water. ml of 36% hydrochloric acid and 63.7 g of 2-difluoromethoxyaniline. The reaction mixture is heated to 30 [deg.] C. with evolution of gases. The reaction mixture was stirred for 18 hours, whereupon a brown oil precipitated. After separation of the organic phase, the aqueous phase is extracted with methylene chloride. The combined organic phases and evaporation gave 80.3 g of 2-difluoromethoxyphenylsulfonyl chloride as a brown oil as a crude product.

b) 2-difluoromethoxyphenylsulfonamide

To a mixture of 250 ml of methylene chloride, 250 ml of water and 250 ml of 30% ammonia solution was slowly added a solution of 80.3 g of crude 2-difluoromethoxyphenylsulfonyl chloride in 50 ml of methylene chloride. After the exothermic reaction subsided, the reaction mixture was refluxed for 2 hours. After washing the organic phase with water, drying over sodium sulfate, evaporating and recrystallizing from methanol, 40.5 g of 2-difluoromethoxyphenylsulfonamide, m.p. 128 DEG-130 DEG C., are obtained.

Example 4

(a) 2-pentafluoroethoxysulfonyl chloride

To a solution of 6.4 g of copper sulphate in 276 ml of 36% hydrochloric acid and 72 ml of water, 101.2 g of a 40% sodium bisulfite solution was added dropwise while cooling at 0 ° C. 101.2 g of a 40% sodium bisulfite solution and a cooled solution of the diazonium salt, which was obtained by dropwise addition of 28.8 g of sodium nitrite in 44 ml of water, were added dropwise while cooling to a solution of 39 ml of water. ml of 36% hydrochloric acid and 90.8 g of 2-pentafluoroethoxyaniline. The reaction mixture is heated to 30 [deg.] C. with evolution of gases. After stirring the reaction mixture for 18 hours, a brown oil precipitated. After separation of the organic phase, the aqueous phase is extracted with methylene chloride. Combine and evaporate the organic phases to give 2-pentafluoroethoxyphenylsulfonyl chloride as a brown oil.

b) 2-pentafluoroethoxyphenylsulfonamide

To a mixture of 250 ml of methylene chloride, 250 ml of water and 250 ml of 30% ammonia solution is added a solution of the crude 2-pentafluoroethoxyphenylsulfonyl chloride obtained according to Example 2a), in 50 ml of methylene chloride. After the exothermic reaction subsided, the reaction mixture was refluxed for 2 hours. The organic phase was washed with water, dried over sodium sulfate, evaporated and recrystallized from methanol to give 65.0 g of 2-pentafluoroethoxyphenylsulfonamide, m.p. 145-146 ° C.

The following new intermediates, especially for the synthesis of compounds of formula I, are prepared in an analogous manner:

Table 3

IX-AL ·

^R 1 h ₂ X AND m Position X-A Physical data H H 0 -c ₂ F ₅ 1 2 mp 1 ° 5 to 146 ° 6-COOCH _p CH 2 H 0 -chf ₂ 1 2 6-C00CH _? CH 2 H WITH -chf ₂ 1 2 6-COOCH H SO -chf ₂ 1 2 6-COOCH _? CH 2 H Sat ₂ -chf ₂ 1 2 6-C1 5-C1 O -chf ₂ 1 2 6-C1 5-C1 with -ghf ₂ 1 2 6-C1 5-C1 Sat -chf ₂ 1 2 6-C1 5-C1 S0 ₂ -chf ₂ 1 2 H 5-CF ₃ 0 -chf ₂ 1 2 H 5-CP ₃ with -chf ₂ 1 2 H 5-CF ₃ Sat -chf ₂ 1 2 H 5-CF ₃ S0 ₂ -chf ₂ 1 2 H H 0 -chf ₂ 2 2.5 H H with -c ^ f ₂ 2 2.5 H H Sat -chf ₂ 2 2.5 H H SOg -chf ₂ 2 2.5 H 6-NOg 0 -chf ₂ 1 3 6-C00CH _? CH 2 H 0 -CF ₃ 1 2 6-cooch ₂ ch ₂ H with -CF ₃ 1 2

.224000.

Table 3 - continued

^fi 1 «2 X AND m Position X-A Physical data 6-COOCH _? CH 2 H SO -CF ₃ 1 2 6-C00CH _? CH 2 H Sat ₂ -CF ₃ 1 2 D-COOCH3CH3 H 0 -CF, CIff ₂ 1 2 _6-3 COOCHCH H with -CF ₂ -CHF ₂ 1 2 6-GOOCH _? CH _? H Sat -cf ₂ -chf ₂ 1 2 6-C00CH _? CH 2 H Sat ₂ -CF ₂ -CHF ₂ 1 2 3-P H 0 ch ₂ f 1 2 3-Br H 0 ch ₂ f 1 2 5-C1 H 0 ch ₂ f 1 2 H 6-OCH ₃ 0 CHgF 1 2 5-SCH H 0 CHgF 1 2 _5-CH3 H 0 CH ₂ F 1 2 5-Br H 0 chf ₂ 1 2 H 6-F 0 gh ₂ f 1 2. 5-NO ₂ H 0 chf ₂ 1 2 t. t. 176 to 178 ° 5-so _? ch ₃ H 0 CH ₂ F . 1 2 H H with c ₂ f ₅ 1 2 H H Sat ^C 2 ^H 5 1 2 H H S0 ₂ ^C 2 ^F 5 1 2 H 5-F 0 ch ₂ 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 ₃ 1 3 H 6-COOCH ₂ CH ₃ with CF ₃ 1 3 H 6-COOCH ₂ CH ₃ SO CF ₃ 1 3 H δ-COOCH 8 Cl 2 S0 ₂ CF ₃ 1 1 ' 3 H H 0 -cf ₉ -cf ₉ ci 2 H H 0 -CFg-CFgBr 1 2 H H 0 -CH ₂ -CH ₂ F 1 2 H H with -CH 1 -CH 2 F 1 2 H H with -cf ₂ -cf ₂ ci 1 2 H H 0 -CH ₂ -CCl ₃ 1 2 H H 0 -CF ₂ -CH ₃ 1 2 H H with -ch ₂ -cci. 1 2 H H 0 -CFgCl 1 2 H H Sat -CF ₂ Cl 1 2 H H SO ₂ -cf ₂ ci 1 2 H H 0 _{-CH2 -CH2} C1 1 2 t. t. 1 io ‘ H H with -ch ₉ -ch ₉ ci 1 2 6-COOCH ₃ H 0 chf ₂ 1 2 6-NO ₂ H 0 chf ₂ 1 2 H H 0 -CF ₃ 1 2 t. t. 176 to 178 ° H H with -CF ₃ 1 2 H H Sat -CF ₃ 1 2 H H H H SO ₂ 0 -CF ₃ -CHF 8 1 1 2 2 t. t. 128 to 130 ° H H with -CHF ₂ 1 2 t. t. 14, to 142 ° H H Sat -chf ₂ 1 2 t. t. 158 to 160 ° H H Sat ₂ -chf ₂ 1 2 H H 0 -cf ₂ -chcif 1 2 t. t. 110 to 112 °

Table 3 - continued

»1 »2 X AND m Position X-A Physical data H H WITH -CPg-CHCIP  1 2 H H Sat -CFgCHCIF 1 2 H H SO ₂ -CP ₂ -CHClP 1 2 H H 0 -CF _? -CHF _? 1 2 mp 116-118 ° H H with -CPj-CHFj 1 2 mp 106-108 ° H H Sat -cp ₂ -chp ₂ 1 2 H H SO ₂ -cf ₂ -chp ₂ 1 2 H H 0 -CPg-CHBrP 1 2 H H with -CP ₂ -CHBrP 1 2 H H Sat -CPg-CHBrF 1 2 H H S0 ₂ -CPg-CHBrF 1 2 6-C1 H 0 -chp ₂ 1 2 mp 90-95 ° 6-C1 H with -chf ₂ 1 2 6-C1 H Sat -chf ₂ 1 2 6-C1 H SO ₂ -chp ₂ T 2 H 5-C1 0 -chf ₂ 1 2 mp 129-131 ° H 5-C1 C -cp ₂ -chcif . 2 H 5-C1 Sat -cp ₂ -chcip 1 2 H 5-C1 S0 ₂ -cf ₂ -chcip 1 2 H 5-C1 0 -CFg 1 2 H 5-C1 with -CFg 1 2 H 5-F with -chp ₂ 1 2 H 5-P 0 -chf ₂ 1 2 mp 138-120 ° H 5-F Sat -CHFg 1 2 H 5-P Sat ₂ -chp ₂ 1 2 H 5-C1 Sat -OFg 1 2 H 5-C1 S0 ₂ -CFg 1 2 H H with -CHFg 1 3 H H Sat -chp ₂ 1 3 H H Sat ₂ -chp ₂ 1 3 6-F H 0 -chp ₂ 1. 2 6-F H with -CHFg 1 2 6-F H Sat ₂ -chf ₂ 1 2 H 6-CHg 0 -chf ₂ 1 . 3 H 6-CHg with -chp ₂ 1 3 H 6-CHg Sat -chf ₂ 1 3 H 6-CHg S0 ₂ -chp ₂ 1 3 H 6-C1 0 -chf ₂ 1 3 H 6-C1 WITH -chp ₂ 1 3 H 6-C1 SO -chf ₂ 1 3 H 6-C1 SO ₂ -chp ₂ 1 3 H 6-C1 0 -CPg 1 3 H 6-C1 with -CPg 1 3 H 6-C1 Sat -CFg 1 3 H 6-C1 SO ₂ -CPg 1 3

. 224000

Example 5

a) N- (2-allyloxyphenylsulfonyl) phenylcarbamate

To a suspension of 0.56 g of sodium hydride (55%) in 5 ml of absolute dimethylformamide was added dropwise over 5 minutes at a temperature of not more than 20 ° C under a nitrogen atmosphere in 2.66 g of 2-allyloxyphenylsulfonamide in 20 ml of dimethylformamide. 2.91 g of diphenylcarbamate in 20 ml of dimethylformamide are then added dropwise. The reaction mixture was further stirred for 30 minutes and then extracted with a mixture of 80 ml of ethyl acetate, 80 g of ice and 12.3 ml of 2N hydrochloric acid solution. The organic phase is washed twice with ice water, dried over sodium sulphate and evaporated. Crystallization from ether / petroleum ether (1: 1) gave 3.5 g of N- (2-allyloxyphenylsulfonyl-5-phenylcarbamate), m.p. 140-141 ° C.

b) N- (2-allyloxyphenylsulfonyl) -N '- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) urea

A mixture of 3-33 g of N- (2-allyloxyphenylsulfonylphenylcarbamate) and 1.4 g of 2-amino-4-methoxy-6-methyl-1,3,5-triazine in 30 ml of absolute dioxane is heated at reflux for 30 minutes. condenser, then cooled to 20 ° C, filtered, the filtrate was evaporated and the residue was crystallized from ether and recrystallized from ethyl acetate / petroleum ether (1: 1) to give 2.0 g of N- (2-allyloxyphenylsulfonyl) -N 146 DEG-147 DEG C. 1- (4-Methoxy-6-methyl-1,3,5-triazin-2-yl) urea.

The compounds of the formula I shown in the following table are prepared in an analogous manner:

Table

O

II

X-A

fiíslo AND ^R 1 ^R 3 ^R 4 X E Physical data 1 2 -CH ₂ -CH = CH ₂ -ch ₂ -ch = ch ₂ 6-C1 6-C1 ch ₃ ch ₃ OCH ₃ OCH ₃ 0 0 N CH mp 142-145 ° mp 163-164 ° 3 -ch ₂ -ch = ch ₂ 6-C1 c ₂ h ₅ OCH ₃ 0 N 4 -ch ₂ -ch = ch ₂ 6-C1 och ₃ och ₃ 0 CH 5 -ch ₂ -ch = ch ₂ 6-C1 OCH ₃ OCH ₃ 0 N CH, I ³ 6 -CH ₂ -C = CH ₂ 6-C1 ch ₃ 0CH ₃ 0 N CH I ³ 7 -CH ₂ -C = CH ₂ 6-C1. ch ₃ OCH ₃ 0 CH CH 1 ³ 8 -CH ₂ -C = CH ₂ 6-C1 ^C 2 ^H 5 och ₃ 0 N ° ^Η 3 9 -ch ₂ -c = ch ₂ 6-C1 och ₃ och ₃ 0 N 10 ^CH 3 -ch ₂ -c = ch ₂ 6-C1 OCH ₃ OCH ₃ 0 CH 11 -ch ₂ -ch = ch-ch ₃ 6-C1 OCH ₃ 0CH ₃ 0 CH 12 -ch ₂ -ch = ch-ch ₃ 6-C1 OCH ₃ 0CH ₃ 0 N 13 -CH ₂ -CH = CH-CH ₃ 6-C1 OCH ₃ CH ₃ 0 N

Table 4 - continued

CíbIo A

R ₁ R ₃ . R ₄ XE Physical Data ·

14 -CH ₂ -CH = CH-CH ₃ . 6-C1 ° ch ₃ CH ₃ 0 CH 15 Dec CH3 ^ CH, CH ² = C \ CH ₃ 6-C1 CH ₃ OCH ₃ 0 N 16 ( ^CH 3 -CH, -CH = C) 6-C1 CH, OCH, 0 CH

17 -CH ₂ -CCH ₃ 6-C1 ch ₃ ch ₃ OCH ₃ OCH ₃ 0 CH 18 -CH ₂ -OCH ₃ 6-C1 0 N 19 Dec -CH ₂ -OCH ₃ 6-C1 c ₂ h ₅ ch ₃ OCH ₃ 0 N 20 May - (ch ₂ ) ₂ -och ₃ 6-C1 OCH ₃ 0 N 21 - (CH ₂ ) ₂ -OCH ₃ 6-C1 ch ₃ och ₃ 0 CH 22nd -ch ₂ -sch ₂ 6-C1 ch ₃ och ₃ 0 CH 23 -CH ₂ -SCH ₂ 6-C1 CH ₃ 0CH ₃ 0 N 24 - (CH ₂ ) ₂ -SCH ₃ 6-C1 CH ₃ OCH ₃  0 N 25 - (CH ₂ ) ₂ -SCH ₃ 6-C1 ^OBJECTIVE 3 OCH ₃ and ₃ 0 CH 26 -ch ₂ ch = ch ₂ 6-OCH ₃ ch ₃ 0 CH 27 Mar: -CH ₂ CH = CH ₂ 6-OCH ₃ ch _{3 OCH3 OCH3 OCH3} 0 N 28 -CH ₂ CH = CH ₂ 6-OCH ₃ C ₂ «5 OCH ₃ 0 N 29 -CH ₂ CH = CH ₂ 6-OCH ₃ 0 N 30 -CH ₂ CH = CH ₂ ° ^Η 3 6-OCH ₃ OCH ₃ OCH ₃ 0 CH 31 -ch ₂ -c = ch ₂ f ^H 3 6-0CH ₃ 0CH ₃ 0CH ₃ 0 CH 32 -CH ₂ -C = CH ₂ Γ ³ 6-OCH ₃ ch ₃ OCH ₃ 0 N 33 -CH-C = CH, 2 ² 6-OCH ₃ CH ₃ 0CH ₃ 0 CH 34 - (CH ₂ ) ₂ -OC ₂ H ₅ 6-0CH ₃ CH ₃ OCH ₃ 0 CH 35 - (ch ₂ ) ₂ -oc ₂ h ₅ ch ₃ 6-OCH ₃ ^CH 3 OCH ₃ 0 N 36 -CH 2 -CH = C ^/ 6-C1 CH, OCH, 0 N

37 _z ch ₃ CH ₃ OCH ₃ 0 CH -ch, -ch = c \ c ' ₃ Cl I 6-ci 38 -ch-c = ch ₂ f ¹ 6-OCH ₃ CH ₃ OCH ₃ 0 N 39 -ch-c = ch ₂ 6-OCH ₃ CH ₃ 0CH ₃ 0 CH

Table 4 - continued l

number AND ^R , ^R 3 ^R 4 X E Physical data Cl | 40 -CH-C = CH ₂ 6-C1 ^CH 3 och ₃ 0 CH mp 163-164 ° 41 f ¹ -CH-C = CH ₂ 6-C1 CH ₃ och ₃ 0 N mp 142-145 ° 42 -ch ₂ -ch = ch _{2 6-CH3} CH ₃ och ₃ 0 M 43 -ch ₂ -ch = ch _{2 6-CH3} CH ₃ och ₃ 0 CH 44 -ch ₂ -gh = ch _{2 6-CH3} OCH ₃ 0CH ₃ 0 CH 45 -ch ₂ -ch = ch _{2 6-CH3} och ₃ och ₃ 0 N CH, | 3 46 -CH ₂ -C = CH _{2 6-CH3} CH ₃ OCH ₃ 0 N CH, | 3 47 -CH ₂ -C = CH _{2 6-CH3} CH ₃ OCH ₃ 0 CH f ^H 3  ' 48 -ch ₂ -c = ch ₂ 6-CH 3 OCH ₃ OCH ₃ 0 N CH, | 3 49 -CH ₂ -C = CH _{2 6-CH3} . och ₃ OCH ₃ 0 CH 50 -CH ₂ -OCH _{3 6-CH3} OCH ₃ och ₃ 0 CH 51 -CH ₂ -OCH _{3 6-CH3} OCH ₃ ^CH 3 0 CH 52 -CH ₂ -OCH _{3 6-CH3} och ₃ CH ₃ 0 N 53 - (CH _? ), - CH = CH _? 6-OCH ₃ och ₃ ' ch ₃ 0 N 54 - (CH _? ) _? -CH = CH _? 6-OCH ₃ OCH ₃ ch ₃ 0 CH 55 -CH _? -SCH _{3 6-CH3} OCH ₃ CH ₃ 0 CH 56 -CH ₂ -SCH _{3 6-CH3} OCH ₃ CH ₃ 0 N 57 -ch ₂ -ch = ch ₂ 6-NO ₂ ch ₃ och ₃ 0 N 58 -ch ₂ -ch = ch ₂ 6-NO ₂ CH ₃ OCH ₃ 0 CH 59 -CH ₂ -CH = CH ₂ 6-NO ₂ OCH ₃ OCH ₃ 0 CH 60 -ch ₂ -ch = ch ₂ 6-NO ₂ OCH ₃ och ₃ 0 N 61 -ch ₂ -ch = ch-ch ₃ 6-NO ₂ 0CH ₃ 0CH ₃ 0 N 62 -CH ₂ -CH = CH-CH ₃ 6-NO ₂ OCH ₃ OCH ₃ 0 CH 63 -ch ₂ -ch = ch-ch ₃ 6-NO ₂ OCH ₃ CH ₃ 0 CH 64 -CH ₂ -CH = CH-CH ₃ 6-NO ₂ och ₃ CH ₃ 0 N 65 -ch ₂ -och ₃ 6-NO ₂ och ₃ CH ₃ 0 N 66 -CH ₂ -OCH ₃ 6-NO ₂ 0CH ₃ CH, 0 CH 67 -CH ₃ -CH ₃ -OC _? H ₅ 6-NO ₂ OCH ₃ ^CH 3 0 CH 68 -CH ₂ -CH ₂ -OC ₂ H ₅ 6-NO ₂ OCH ₃ CH ₃ 0 N f ^H 3 j 69 -CH ₂ -C = CH ₂ 6-NO ₂ OCH ₃ CH ₃ 0 N CH, 13 70 -CH ₂ -C = CH ₂ 6-NO ₂ och ₃ CH ₃ 0 CH 71 -CH ₂ -CH = CH ₂ 6-COOCH ₃ OCH ₃ ch ₃ . 0 CH 72 -CH ₂ -CH = CH ₂ 6-COOCH ₃ OCH ₃ CH, 0 N 73 -CH ₂ -CH = CH ₂ 6-COOCH ₃ OCH ₃ ^CH 3 0 N 74 -CH ₂ -CH = CH ₂ 6-COOCH ₃ OCH ₃ OCH ₃ 0 CH

Table 4 - continued

fiíslo AND ^R 1 ^R 3 ^R 4 X E Physical data 75 -ch ₂ ch = ch ₂ 5-ci CH ₃ 0CH ₃ 0 N mp, 64-166 ° 76 -CH ₂ CH = CH ₂ 5-C1 CH ₃ OCH, 0 CH mp 197-198 ° 77 -CH ₂ CH = CH ₂ 5-C1 och ₃ 0CH ₃ 0 N mp 173 ° 78 -ch ₂ ch = ch ₂ 5-C1 och ₃ 0CH ₃ 0 N 79 -ch ₂ ch = ch ₂ 5-C1 ^C 2 ^H 5 0CH ₃ 0 N Γ ³ of 80 -CH ₂ -C = CH ₂ 5-C1 CH ₃ OCH ₃ 0 N mp 167 ° f ^H 3 81 -ch ₂ -c = ch ₂ 5-C1 CH ₃ 0CH ₃ 0 CH mp, 55 ° 82 -ch ₂ ch = ch ₂ 5-Br ch ₃ 0CH ₃ 0 CH 83, -ch ₂ ch = ch ₂ 5-Br CH ₃ 0CH ₃ . 0 N mp 190-191 ° 84 -CH ₂ CH = CH ₂ 5-Br c ₂ h ₅ CHy 0 N ? ^h 3 85 -ch-c = ch ₂ 5-Br CH ₃ 0CH ₃ 0 N CH, í 3 86 -ch-c = ch ₂ 5-Br OCH ₃ OCH ₃ 0 N f ^H 3 87 -ch-c = ch ₂ 5-Br CH ₃ 0CH ₃ 0 CH 88 -CH ₂ -OCH ₃ 5-Br CH ₃ 0CH ₃ 0 CH 89 -CH ₂ -0CH ₃ 5-Br CH ₃ OCH ₃ 0 N 90 -ch ₂ -ch = ch ₂ 5-F CH ₃ 0CH ₃ 0 N mp 159-161 ° 91 -ch ₂ -0h = ch ₂ 5-F CH ₃ 0CH ₃ 0 CH 200 DEG-201 DEG 92 -ch ₂ -ch = ch ₂ 5-F OCH ₃ ^C 2 ^H 5 0 N 93 -ch ₂ -ch = ch ₂ 5-F OCH ₃ 0CH ₃ 0 CH mp 162-164 ° ch, / 3 94 -CH, -CH = C 5-F CH, OCH, 0 N 3 3 qh ₃ • ^ ^GH 3 95 -ch ₂ -ch = c 5-F CH ₃ 0CH ₃ 0 CH ^ 0Η ₃ ^GH 3 96 -ch ₂ -c = ch ₂ 5-F CH ₃ OCH ₃ 0 CH mp 197 ° J ^H 3 97 -ch ₂ -c = ch ₂ 5-F CH ₃ OCH ₃ 0 N mp 155 ° | ^H 3 / 5 98 -CH ₂ -C = CH ₂ 5-CH CH ₃ 0CH ₃ 0 N ^ ch ₃ f ^H 3 / ^H 3 99 -CH ₂ C = CH ₂ 5-CH CH ₃ och ₃ 0 CH

Table 4 - continued number A ^R 1

Rj R ^ X E Physical data

_From ^CH 3 _z ch ₃ 100 ALIGN! -CH, -CH = C 5-CH CH, OCH, O CH '' CHj. 3 3 X ^CH 3 ° ^h 3 101 -CH, -CH = C 5-CH CH, OCH, 0 N ³ \ ch ₃ \ _C h ₃ 3 3

102 -ch ₂ -ch = ch ₂ 5-CH ^ CHj CHj OCHj 0 N t. t. 259 to 260 ° _From ^CH 3 103 -ch ₂ -ch = ch ₂ 5-CH ^ CHj CHj OCHj 0 CH t. t. 139 to 140 ° _{/ C} h ₃ 104 -CH, -CH = CH, 5-CH ^C 2 ^H 5 OCH, 0 N 2 2 ^ CHj 3 CH, _of 3 105 -CH ₂ -CH = CH ₂ 5-CH ' ^ CHj OCHj OCHj 0 N, t. t. 219 to 220 ° , CH, _of 3 106 j -CH ₂ -CH ₂ -OCH ₃ 5-CH ^ CHj CHj och ₃ 0 N CH, of ³ 107 -CH ₂ -CH ₂ -OCH ₃ 5-CH ^ CHj CHj OCHj 0 CH 108 -CH ₂ -CH ₂ -OCH ₃ 5-CH 3 CHj OCHj 0 CH 109 -CH ₂ -CH ₂ -OCH ₃ ' 5-CH 3 CHj och ₃ 0 N 110 -CH ₂ -CH ₂ -OCH ₃ 5-CH 3 CHj Cl 0 CH 1 11 -CH ₂ -CH ₂ -OCH ₃ 5-CH 3 OCHj Cl 0 CH ^1,2 -ch ₂ -ch = ch ₂ 5-CH 3 CHj OCHj 0 N t. t. 158 to 162 ° 113 -ch ₂ -ch = ch _{2 5-CH3} CHj OCHj 0 - N H4 -ch ₂ -ch = ch ₂ 5-CH 3 c ₂ h ₅ OCHj 0 N 115 -ch ₂ -ch = ch _{2 5-CH3} OCHj OCHj 0 N t. t. 160 to 165 ° 116 -ch ₂ -ch = ch ₂ 5-CH 3 CHj OCHj 0 CH t. t. 200 to 202 ° 117 -ch ₂ -ch = ch-ch ₃ 5-CH 3 OCHj OCHj 0 CH 118 -CH ₂ -CH = CH-CH ₃ 5-CH 3 CHj OCHj 0 CH t. t. 179 to 182 ° 119 -ch ₂ -ch = ch-ch ₃ 5-CH 3 CHj OCHj 0 N 120 -CH ₂ -CH = CH-CH ₃ 5-NO ₂ ch ₃ OCH, 0 N 12, -CH ₂ -CH = CH-CH ₃ -CH ₂ -CH = CH-CH ₃ 5-NO ₂ CHj OCHj 0 'CH , 22 5-NO ₂ ^C 2 ^H 5 OCHj 0 N 123 -CH ₂ -CH = CH-CH ₃ 5-NO ₂ OCHj OCHj 0 N , 24 _-CH2 -CHxCH ₂ 5-NO ₂ OCHj OCHj 0 N. , 25 -ch ₂ -ch = ch ₂ 5-NO ₂ CHj OCHj 0 N 126 -ch ₂ -ch = ch ₂ 5-NO ₂ ch ₃ OCHj 0 CH

Table 4 - continued

number AND ^R 1 ^R 3 ^R 4 X ' E Physical data 127 -CH ₂ -SCH ₃ 5-NO ₂ CH ₃ OCH ₃ 0 CH 128 -CH ₂ -SCH ₃ 5-NO ₂ CH ₃ OCH ₃ 0 N 129 -CH ₂ -SCH ₃ S-no ₂ OCH ₃ OCH ₃ 0 N 130 -CH ₂ -SCH ₃ 5-NO ₂ OCH ₃ 0CH ₃ 0 CH 131 -ch ₂ -ch = ch ₂ 5-OCH ₃ CH, OCH, 0 N t. t 142 to 143 ° 132 -ch ₂ -ch = ch ₂ 5-OCH ₃ CH ³ 0CH ₃ 0 CH 138 to 139 ° 133 -ch ₂ -ch = ch ₂ 5-OCH ₃ 0CH ₃ 0CH ₃ 0 CH 134 -ch ₂ -ch = ch ₂ 5-OCH ₃ 0CH ₃ 0CH ₃ 0 N 135 -ch ₂ -ch = ch ₂ 5-OCH ₃ 0CH ₃ ^C 2 ^H 5 0 N CH, | 3 136 -CH ₂ -C = CH ₂ 5-OCH ₃ 0CH ₃ CH ₃ 0 N ° ^H 137 -ch ₂ -c = ch ₂ 5-OCH ₃ OCH ₃ CH ₃ 0 CH Γ ³ 138 -ch ₂ -c = ch ₂ 5-OCH ₃ och ₃ OCH,  0 N t 139 -CH ₂ -CH = CH-CH ₃ 5-OCH ₃ OCH ₃ ch ₃ ³ 0 N 140 -CH ₂ -CH =; CH-CH ₃ 5-OCH ₃ OCH ₃ CH ₃ 0 CH 141 -CH ₂ -CH = CH-CH ₃ 5-OCH ₃ OCH ₃ OCH ₃ 0 CH 142 -CH ₂ -CH = CH-CH ₃ 5-OCH ₃ OCH ₃ och ₃ 0 N 143 -CH ₂ -OCH ₃ 5-OCH ₃ och ₃ OCH ₃ 0 N 144 -CH ₂ -OCH ₃ 5-OCH ₃ CH, OCH ₃ 0 N 145 -CH ₂ -0CH ₃ 5-OCH ₃ . CH ³ OCH ₃ 0 CH 146 -CH ₂ -OCH ₃ 5-OCH ₃ ^C 2 ^H 5 OCH ₃ 0 N 147 -ch ₉ -ch _? -sch, 5-0CH ₃ CH, 0CH ₃ 0 N 148 -CHp-CHp-SCH2 5-OCH ₃ CH ³ OCH ₃ 0 CH 149 -CH ₂ -CH ₂ -SCH ₃ 5-OCH ₃ OCH ₃ . 0CH ₃ 0 N

150 -ch ₂ -ch = ch ₂

151 -ch ₂ -ch = ch ₂

F ³

152 -CH ₂ -C =CH ₂ f ^H 3

153 -CH ₂ -C =CH ₂

Γ ³

154 -CH ₂ -C =CH ₂ ' ³

155 -CH ₂ -C =CH ₂

5-CON / ^CH3

5-CON

5-CON

CH, 'CH,' CH, 'CH,

X ° ^H 3 [

^ CH,

5-CON

CH,

CH,

From “ ³ j '·· CH,' CH,

_{5-COOCH3 CH3}

_{5-COOCH3 CH3}

OCH ₃ on

OCH ₃ o CH

OCH ₃ on

OCH ₃ o CH

OCH ₃ o CH

OCH ₃ on

Table 4 - continued

Number AND ^R 1 ^R 3 ^R 4 X E Physical data 156 -CH- ₂ -CH = CH ₂ 5-COOCH ₃ CH, 0CH ₃ 0 N 157 -CH ₂ -CH = CH ₂ 5-COOCH ₃ ^CH 3 0CH ₃ 0 CH 158 -CH ₂ -CH = CH ₂ 5-cooch ₄ och ₃ 0CH ₃ 0 N 159 -ch ₂ -ch = ch ₂ 5-COOCH ₃ och ₃ OCH ₃ 0 CH 160 -CHp-OCpHpj 5-COOCH ₃ 0CH ₃ CH ₃ 0 N 161 -ch ₉ -oc _? h ₅ 5-COOCH ₃ 0CH ₃ CH ₃ 0 N 162 -ch ₀ -c = ch ₉ 2 1 2 _5-CH3 0CH ₃ CH ₃ 0 N Cl 163 -ch ₉ -c = ch _{9 5-CH3} 0CH ₃ CH ₃ 0 CH th 164 -CH ₂ -C =CH-Cl 5-NO ₂ 0CH ₃ CH ₃ 0 CH Cl 165 -CH ₂ -C =CH-Cl 5-NO ₂ 0CH ₃ ^CH 3 0 N Cl 166 -CH--C = CH-Cl 5-Br OCH ₃ CH ₃ 0 N clay 167 -CH _? -C = CH-Cl 5-Br 0CH ₃ CH ₃ 0 CH Cl 168 -CH, -C =CH-Cl 5-C1 0CH ₃ ^CH 3 0 N Cl Cl 169 -CH ₂ -C = CH ₂ 5-C1 CH ₃ OCH ₃ 0 CH 170 > ^C1 -CH, -CH ² CH ₃ C 5-C1 CH ₃ 0CH ₃ 0 N 171 x ^G1 -ch ₂ -ch = c 5-C1 CH ₃ OCH ₃ 0 CH ^ CH ₃ 172 X Cl, -CH ² -CH = C \ ^ C1 X ^CH 3 5-CH Xh ₃ CH ₃ OCH ₃ 0 CH 173 X ^{C 1} -CH ₂ -CH = C 1-01 5-CH = CH ₃ CH ₃ 0CH ₃ 0 N Cl 174 -CH ₂ -C = CH ₂ 3-CH ₃ CH ₃ 0CH ₃ 0 H

Table 4 - continued

Number A

X E Physical data

Cl

AND

175 -CH ₂ -C = CH ₂ Cl 3-CK ₃ ^CH 3 OCH ₃ 0 CH 176 | -CH ₂ -C = CH _{2 6-CH3} ^CH 3 0CH ₃ 0 N 177 -CH ₂ -C = CH _{2 6-CH3} ch ₃ 0CH ₃ 0 CH I ¹ 178 -CH ₂ -C =CH-Cl 6-OCH ₃ CH ₃ OCH ₃ 0 CH Cl, j 179 -CH ₂ -C-CH-Cl 6-OCHj ch ₃ OCH ₃ 0 N 180 z ⁰¹ -ch ₂ -ch = c ^ Cl 5-OCH ₃ ch ₃ och ₃ 0 N 181 z ^ci -CH _? -CH = C 5-OCH ₃ ^CH 3 OCH ₃ 0 CH > 31 Cl | 182 -ch ₂ -c = ch ₂ 6-C1 ch ₃ OCH ₃ 0 N Cl 183 | -CH ₂ -C = CH ₂ 6-C1 ch ₃ 0CH ₃ 0 CH 184 -ch ₂ -ch = ch ₂ 3-NO ₂ ch ₃ och ₃ 0 CH 185 -ch ₂ -ch = ch ₂ 3-NO ₂ CH ₃ OCH ₃ 0 N 186 -ch ₂ -ch = ch ₂ 3-NO ₂ ^C 2 ^H 5 OCH ₃ 0 N 187 -ch ₂ -ch = ch ₂ 3-NO ₂ OCH ₃ OCH ₃ 0 N 188 _O-CH = CH-C ~ ² 1 ² 3-NO ₂ CH ₃ 0CH ₃ 0 N CH ₃ 189 -ch ₂ -c = ch ₂ 3-NO ₂ CH ₃ 0CH ₃ 0 CH CH ₃ 190 -ch ₂ -c = ch ₂ 3-NO ₂ 0CH ₃ och ₃ 0 N ch ₃ 191 -ch ₂ -c = ch ₂ 3-N ° ₂ och ₃ och ₃ 0 CH CH ₃ Cl 192 | -CH ₂ -CH = C-CH ₃ 3-NO ₂ . och ₃ OCH ₃ 0 CH Cl 193 | -CH ₂ -CH = C-CH ₃ 3-NO ₂ och ₃ CH ₃ 0 CH

Table 4 - continued

Number AND ^R , ^R 3 ^R 4 X E Physical data Cl 194 -CH ₂ -CH = C-CH ₃ 3-NO ₂ OCH ₃ CH ₃ 0 N 195 -ch ₂ -ch = ch ₂ 3-CH ₃ och ₃ CH ₃ 0 N mp 255-256 ° 196 -CH ₂ -CH = CH ₂ 3-CH ₃ OCH ₃ CH, 0 CH mp 163-164 ° 197 -CH ₂ -CH = CH ₂ 3-CH ₃ c ₂ h ₅ ch ₃ 0 , N , 98 -ch ₂ -ch = ch ₂ 3-CH ₃ OCH ₃ ch ₃ 0 N mp 183-184 ° , 99 -ch ₂ -ch = ch ₂ 3-CH ₃ 0CH ₃ ch ₃ 0 CH 200 -ch ₂ -ch = ch ₂ 3-C1 0CH ₃ ^CH 3 0 N mp 183-187 ° 20, -CH ₂ CH = CH ₂ 3-C1 OCH ₃ CH ₃ 0 N 202 -ch ₂ -ch = ch ₂ 3-C1 och ₃ och ₃ 0 N 203 -CH ₂ -CH = CH ₂ 3-C1 OCH ₃ ° CH ₃ 0 CH ch, 13 204 -CH ₂ -C = CH ₂ 3-C1 OCH ₃ OCH ₃ 0. N ? ^H 3 205 -CH ₂ -C = CH ₂ 3-C1 0CH ₃ CH ₃ 0 N CH, | 3 206 -CH ₂ -C = CH ₂ 3-C1 0CH ₃ CH ₃ 0 CH 207 -CH ₂ -CH = CH-CH ₃ 3-C1 CH ₃ OCH ₃ 0 N 208 -ch ₂ -ch = ch-ch ₃ 3-C1 CH ₃ OCH ₃ 0 CH CH, (3 209 -ch ₂ -c = ch ₂ 3-OCH ₃ CH ₃ 0CH ₃ 0 CH CH, 13 210 -ch ₂ -c = ch ₂ 3-0CH ₃ CH ₃ 0CH ₃ 0 N 211 -ch ₂ -ch = ch ₂ 3-OCH ₃ CH ₃ OCH ₃ 0 N 2.2 -ch ₂ -ch = ch ₂ 3-OCH ₃ CH ₃ OCH ₃ 0 CH 2.3 -ch ₂ -ch = ch ₃ 3-OCH ₃ 0CH ₃ OCH ₃ 0 CH 2.4 -ch ₂ -ch = ch ₂ 3-0CH ₃ c ₂ h ₅ och ₃ 0 N 2.5 -ch ₂ -ch = ch ₂ 3-0CH ₃ 0CH ₃ OCH ₃ 0 N Taboo 1 k and 5 0 SO 2 NH-C-NH R, / y at ~ X ~ A

Number AND ^R 3 ^R 4 X E Physical data 301 ? ^H 3 '-CH ₂ -C =CH ₂ CH ₃ ch ₃ 0 N mp 95-103 ° 3021 f ^H 3 -ch ₂ -c = ch ₂ ch ₃ och ₃ 0 N t. 142-143 '

'224000

Number A

Table 5 - continued

303

304

305

306

307

308

309

310

31.1

312

313

314

315

316

317

318

319

-CH ₂ -C = CH ₂ f ^H 3

-CH ₂ -C = CH ₂ f ^H 3

-ch ₂ -c = ch ₂

-ch ₂ -c = ch ₂

CH ₃

-ch ₂ - £ = ch ₂ | ^H 3

-ch ₂ -c = ch ₂

CH,

I ³

-ch ₂ -c = ch ₂ ? ^H 3

-ch ₂ -c = ch ₂

CH,

-CH ₂ -C = CH ₂ f ^H 3

-CH ₂ -C = CH ₂ f ^d 3

-CH ₂ -C = CH ₂

CH ₃

-CH ₂ -I = CH ₂

Γ ³

-CH ₂ -C = CH ₂

CH,

-CH ₂ -C = CH ₂

CH,

-CH, - (II = CH) 2 CH,

-ch ₂ -c = ch ₂

CH,

-ch ₂ -c = ch ₂

OCH,

OCH, ch ₂ -ch ₃

OOH, OC ₂ H ₅

OCH, ch ₂ -ch ₃ ch ₃

Cl

OCH,

-OCH (CH ₃ ) ₂ OCH ₃

-OCH (CH ₃ ) ₂ OCH ₃

-OCH (CH _{3) 2} CH ₃

OCH,

SCH _{OC2 H5 OC2 H5}

OCH,

CH ₂ Cl ₂ f

CH,

OCH,

CH, c ₂ h ₅

-CH ₂ OCH ₃

OCH,

OCH,

OCH,

OCH,

CH,

OCH,

X E Physical give

O N mp 145-153 °

O N

O N mp 150-152 °

O N mp 129-130 °

O N

O N

O N

O N

HE

O N mp 118-120 °

O N

O N

O N

Mp 172-177 °

O CH

O CH

O CH

Table 5 - continued

Physical data.

number AND ^R 3 ^R 4 X £ f ^H 3 320 -CH ₂ -C = CH ₂ OCH ₃ Cl 0 CH CH, | ³ 321 -CH ₂ -C = CH ₂ CH ₃ Cl 0. CH ° ^Η 3 322 -ch ₂ -c = ch ₂ CF ₃ OCH ₃ 0 CH f «3 323 -ch ₂ -c = ch ₂ -CH ₂ -0CH ₃ och ₃ 0 CH ? ^H 3 324 -ch ₂ -c = ch ₂ Br OCH ₃ 0 CH 325 -CH ₂ -C = CH ₂ Br CH ₃ 0 CH ° ^Η 3 » 326 -CH ₂ -C = CH ₂ OCH ₃ sch ₃ 0 CH f ^H 3 327 -CH ₂ -C = CH ₂ ch ₃ SCH ₃ 0 CH J ^H 3 och ' ₃ 328 -CH ₂ -C = CH ₂ C ₂ H ₅ 0 CH 329 -CH ₂ -CH = CH-CH ₃ ch ₃ OCH ₃ 0 H 330 -CH ₂ -CH = CH-CH ₃ ch ₃ CH ₃ 0 N 331 -CH ₂ -CH = CH-CH ₃ ^C 2 ^H 5 OCH ₃ 0 N 332 -CH ₂ -CH = CH-CH ₃ ^C 2 ^H 5 CH ₃ 0 N 333 -CH ₂ -CH = CH-CH ₃ 0CH ₃ 0CH ₃ 0 N 334 -CH ₂ -CH = CH-CH ₃ 0CH ₃ oc ₂ h ₅ 0 N 335 -CH ₂ -CH = CH-CH ₃ oc ₂ h ₅ oc _? h ₅ 0 N 336 -CH ₂ -CH = CH-CH ₃ -CH ₂ -OCH ₃ OCH ₃ 0 H 337 -CH ₂ -CH = CH-CH ₃ CH ₃ 0CH ₃ 0 CH 338 -CH ₂ -CH = CH-CH ₃ OCH ₃ OCH ₃ 0 CH 339 -CH ₂ -CH = CH-CH ₃ CH ₃ CH ₃ 0 CH 340 -CH ₂ -CH = CH-CH ₃ -CH ₂ -0CH- OCH, 0 CH 341 -CH ₂ -CH = CH-CH ₃ CH ₃ Cl 0 CH 342 -CH ₂ -CH = CH-CH ₃ -CH ₂ -CH = CH-CH ₃ OCH ₃ Cl 0 CH 343 0CH ₃ oc ₂ h ₅ 0 CH 344 _X ^CII -CH 3, -CH = C = CH ₃ CH ₃ OCH ₃ 0 N · 345 Z ' ³ -CH, -CH = CH 2 CH ₃ CH ₃ ch ₃ 0 N

mp 179-180 °

mp 163-164 °

mp 139-140 ° mp 148-151 ° mp 148-149 °

185 DEG-186 DEG

X E Physical data

Table 5 - continued

346

-ch ₂ -ch = c ₂ ^ch 3 'CH, c ₂ h ₅

CH,

347

-CH ₂ -CH = C ^CH 3 _Z 'CH, ^C 2 ^H 5

OCH,

348

-ch ₂ -ch = c

349

-CH ₂ -CH = C ^CH 3 _{Z 'Z} XcHj ^{CH3 Χχ} € ^Η-,

OCH, OCH,

350

-ch ₂ -ch = c _{/ C} h ₃

351 -CH ₂ -CH = C

352

-ch ₂ -ch = c ch _{3 From} ^C «3 \ η _{3 of} ^ch 3

CH,

OCH, OC ₂ H ₅

353 -CH ₂ -CH = C / ^CH 3

X-CH,

354

-ch ₂ -ch = c _{/ C} h ₃ 'CH,

355 -CH ₂ -CH = c:

_From ^CH 3 'CH,

356

-CH ₂ -CH = C _x CH ₃ 'CH,

357 -CH ₂ -CH = c ' _Z ^CH 3' CH,

358

Cl

AND

-ch ₂ -c = ch _? oc ₂ H ₅ oc ₂ H ₅

-CH ₂ -0CH ₃

OCH,

CH,

OCH,

OCH, OCH,

CH,

CH,

OCH, Cl

CH,

Cl

OCH,

CH,

O CH

O CH

CH

O CH

O CH oc ₂ h ₅

OCH,

O CH

Table 5 - continued

Physical data

Number AND ^and 3 ^R 4 X E 359 Cl 1 -CH ₂ -C =CH ₂ CH ₃ ch ₃ 0 N 360 Cl 1 -CH ₂ -C =CH ₂ ^C 2 ^H 5 ck ₃ 0 N 361 Cl 1 -CH ₂ -C =CH ₂ ^C 2 ^H 5 0CH ₃ 0 N 362 Cl 1 -CH ₂ -C =CH ₂ OCH ₃ och ₃ 0 N 363 Cl 1 -CH ₂ -C =CH ₂ OCH ₃ oc ₂ h ₅ 0 N 364 Cl 1 -CH ₂ -C =CH ₂ oc ₂ h ₅ oc ₂ ^h 5 0 N 365 Cl 1 -CH ₂ -C =CH ₂ , -CH ₂ -OCH ₃ och ₃ 0 H 366 Cl 1 -CH ₂ -C =CH ₂ ch ₃ OCHj 0 CH 367 Cl 1 -CH ₂ -C =CH ₂ OCH ₃ 0CH ₃ 0 CH . » 368 Cl 1 -CH ₂ -C =CH ₂ CH ₃ ch ₃ 0 CH 369 Cl 1 -CH ₂ -C =CH ₂ OCH ₃ Cl 0 CH 370 Cl 1 -CH ₂ -C =CH ₂ CH ₃ Cl 0 CH 371 Cl, -CH ₂ - (! = CH ₂ oc ₂ h ₅ OCH ₃ 0 CH 372 Cl-CH ₂ -? = CH ₂ -ch ₂ -och. OCH ₃ 0 CH 373 -OH ₂ -0CH ₃ CH ₃ 0CH ₃ 0 N 374 -CH ₂ -OCH ₃ 0CH ₃ 0CH ₃ 0 N 375 -CH ₂ -0CH ₃ ^C 2 ^H 5 OCHj 0 H 376 -CH ₂ -OCH ₃ C ₂ ^h 5 CH ₃ 0 N 377 -CH ₂ -0CH ₃ <5CH ₃ OCH ₃ 0 N 378 -CH ₂ -OCH ₃ OCH ₃ oc ₂ H ₅ 0 N 379 _-CH2 -OCM ₃ oc ₂ h ₅ oc ₂ h ₅ 0 N 380 -CH ₂ -0CH ₃ -CH ₂ -0CH ₃ och ₃ 0 N 381 -ch ₂ -och ₃ OCH ₃ SCH ₃ 0 N 382 -CH ₂ -OCH ₃ OCH ₃ CH ₃ 0 N

mp 155-157 °

mp 168-175 °

Table 5 - continued

number'' AND ^R 3 ^R 4 X E Physical data 383 -ch ₂ -och ₃ OCH ₃ OCH ₃ 0 CH 384 -CH ₂ -OCH ₃ CH ₃ CH, 0 CH 385 -ch ₂ -och ₃ CH ₃ Cl 0 CH t. t. 137 to 143 386 -ch ₂ -och ₃ och ₃ Cl 0 CH 387 -CH ₂ -OCH ₃ ^C 2 ^H 5 OCH ₃ 0 CH 388 -CH ₂ -OCH ₃ oc ₂ h ₅ och ₃ 0 CH Cl 389 | -CH ₂ -C = CH ₂ ^C 2 ^H 5 OCH ₃ 0 CH CH, / ³ 390 -CH ² -CH = C \ ^ CH ^C 2 ^H 5 OCH ₃ 0 CH 391 -ch ₂ -ch = ch-ch ₃ ^C 2 ^H 5 OCH ₃ 0 CH 392 -ch ₂ -s-ch ch ₃ OCH, 0 N 393 -CH ₂ -S-CH ₃ CH ₃ ch ₃ 0 N 394 -ch ₂ -s ~ ch ₃ c ₂ h ₅ CH ₃ 0 N 395 -ch ₂ -s-ch ₃ ^C 2 ^H 5 OCH ₃ 0 N 396 -CH ₂ -S-CH ₃ 0CH ₃ OCH ₃ 0 N 397 -CH ₂ -S-CH ₃ OCH ₃ oc ₂ h ₅ 0 N 398 -CH ₂ -S-CH ₃ -ch, -och. OCH ₃ 0 N 399 -CH ₂ -S-CH ₃ ch ₃ OCH ₃ 0 CH 400 -ch ₂ -s-ch ₃ OCH, OCH, 0 CH 40! -CH ₂ -S-CH ₃ CH ₃ ^CH 3 0 CH 402 -CH ₂ -S-CH ₃ ^C 2 ^H 5 OCH, 0 CH 403 -CH ₂ -S-CH ₃ OCH, Cl 0 CH 404 -CH ₂ -S-CH ₃ CH ₃ Cl 0 CH 405 -CH ₂ -S-CH ₃ OCH ₃ oc ₂ h ₅ 0 CH 406 -ch ₉ -ch ₉ -oc ₉ h _r ch ₃ OCH ₃ 0 N 407 -ch _? -ch _? -oc _? h ₅ CH ₃ CH ₃ 0 N 408 -CH ₂ -CH ₂ -OC ₂ H ₅ ^C 2 ^H 5 CH ₃ 0 H 409 -CH3-CH3-OC3H4 ^C 2 ^H 5 OCH ₃ 0 N 410 -CH 3 -CH 2 -OCpH 4 och ₃ OCH ₃ 0 N 41 1 -ΟΗ, -ΟΗρ-ΟΟ, Ης CH ₃ OCH ₃ 0 CH 412 -ch ₉ -ch _? -oc _? h ₅ OCH ₃ OCH, 0 CH t. t 163 to 164 ' 413 -CH _? -CH _? -0CH., OCH ₃ Cl 0 CH t. t. 166 to 168 ' 414 -ch _? -ch _? -och ₇ . ch ₃ Cl 0 CH 415 -ch ₂ -ch = ch ₂ . ch ₃ c ₂ h ₅ with N 416 -ch ₂ -ch = ch ₂ OCH ₃ c ₂ H ₅ with N 417 -ch ₂ -ch = ch ₂ ch ₃ OCH ₃ with CH 418 -CH ₂ -CH = CH ₂ och ₃ OCH ₃ with CH 419 -CH ₂ -CH = CH ₂ , ^CH 3 OCH ₃ Sat N 420 -CH ₂ -CH = CH ₂ och ₃ OCH ₃ Sat N 421 -CH ₂ -CH = CH ₂ OCH ₃ ^C 2 ^H 5 Sat N 422 -CH ₂ -CH = CH ₂ OCH ₃ och ₃ Sat CH 423 -CH ₂ -CH = CH ₂ CH, OCH ₃ Sat CH 424 -CH ₂ -CH = CH ₂ CH < OCH ₃ Sat N 425 -CH ₂ -CH = CH ₂ OCH ₃ OCH ₃ SO ₂ N 426 -CH ₂ -CH ₂ CH ₂ OCH ₃ OCH ₃ SOg N 427 -CH ₂ -C 1 = CH ₂ CH ₃ OCH ₃ SO ₂ CH

Table 5 - continued

Number AND ^R 3 ^R 4 X E Physical data 428 -CH ₂ -QH = CH-CH ₃ CHg OCHg SO ₂ N 429 -CH ₂ -CH = CH-CH ₃ CHg OCHg S0 ₂ CH 430 -CH ₂ -CH = CH-CH ₃ ch ₃ och ₃ Sat CH 431 -CH ₂ -CH = CH-CH ₃ CHg OCHg Sat N 432 -CH ₂ -SO-CH ₃ CHg OCHg 0 N 433 -CH ₂ -SO-CH ₃ CHg OCHg 0 CH 434 -CHg-SO-CHg OCHg OCHg 0 N 435 -CH ₂ -SO-CH ₃ OCHg OCHg 0 CH 436 -ch ₂ -so _? -ch, OCHg OCHg 0 CH 437 -CH ₂ -SO ₂ -CH ₃ CH, ° ch ₃ 0 CH 438 -ch ₃ -so _? -ch, ch ₃ CHg 0 CH 439 -CH _? -SO _? -CH, ^CH3 OCHg OCHg 0 N 440 -CH _? -SO _? -CH, OCH 0 N 441 -CH _? -CH _? -SO-CH OCHg OCH, 0 N 442 -CHp-CHp-SO-CH3 och ₃ ch ₃ 0 N 443 -CH _? -CH _? -SO-CH OCHg ch ₃ 0 CH 444 -CH _? -CH _? -SO _? -CH ₃ OCHg CHg 0 CH 445 -CH _? -CH _? -SO _? -CH, OCHg CHg '0 N 446 -CH ₂ -CH ₂ -SO ₂ -CH ₃ ΐ ^Η 3 ch ₃ OCHg 0 N 447 -CH ₂ -C =CH ₂ ; ^h 3 CH, OCHg with N 448 -CH ₂ -C = CH _{2 from} ^CH 3 ch ₃ OCHg with CH 449 -ch ₂ -ch = c ^ ^Goal 3 / ^CH 3 CHg OCHg with CH 450 -CH ₂ -CH = CH-C ch ₃ OCHg with N 451 -CH ₂ -CH = CH ₂ -CH ₃ CHg OCHg with N ' 452 -CH ₂ -CH = CH ₂ -CH ₃ CHg ocrtg with CH 453 -CH ₂ -CH ₂ -OCH ₃ CHg OCHg with CH 454 -CH _? -CH _? -OCH, CHg OCHg with N 455 - _(CH?) P -CH = CHP CHg OCHg 0 N 456 - (ch ₂ ) ₂ -ch = ch ₂ CHg OCHg 0 CH 457 - (CU,) - CH = CH, CHg CHg 0 N 458 - (CH p) p-CH = CH p CHg CHg 0 CH 459 -CCH _? ) ₃ -CH = CH _? CHg OCH, 0 N 460 - (CH ₂ ) ₃ -CH = CH ₂ X ^CH 3 CHg OCHg 0 CH 461 -CH 2 CH = CH ₂ CHg OCHg 0 N

"CH,

462

-CH

CHg OCHg

O CH

CH = CH,

224000 38

Sabulka 5 - sequel

number AND ^R 3 ^R 4 X E Physical data 463 -ch ₂ -oc ₂ h ₅ ch ₃ och ₃ 0 CH 464 -ch ₂ -oc ₂ h ₅ CH ₃ 0CH ₃ 0 N 465 - ° h ₂ -oc ₂ H5 c ₂ h ₅ och ₃ 0 N 466 -ch ₂ -oc ₂ h ₅ ch ₃ ch ₃ 0 N 467 -CH ₂ -OC ₂ H ₅ CH, CH, 0 CH 468 -CH ₂ -CH ₂ -OCH ₃ CH ₃ ch ₃ 0 CH t 179 to 180 ° 469 -CH ₂ -CH ₂ -OCH ₃ OCH, OCP ₃ 0 N t 141 to 142 ° 470 -CH ₂ -CH _{2 in} OCH ₃ ch ₃ 0CH ₃ 0 H 134 to 138 ° 471 -CH ₂ -CH ₂ -OCH ₃ ch ₃ 0CH ₃ 0 CH 160 to 162 ° 472 -CH ₂ -CH ₂ -SCH ₃ ch ₃ 0CH ₃ 0 CH 473 -CH ₂ -CH ₂ -SCH ₃ CH ₃ 0CH ₃ 0 N Cl | 474 ·· _-CH2-C 1 --C CH ₃ 0CH ₃ 0 N Cl 475 -CH ₂ -C =CH-Cl ch ₃ 0CH ₃ 0 CH Cl | 476 CH-CH = C-CH 2 ³ CH ₃ 0CH ₃ 0 CH Cl 477 | -CH ₂ -CH = C-CH ₃ ch ₃ 0CH ₃ 0 N Cl / 478 -CH, -CH = C CH, OCH, 0 N ² \ 3 3 Cl > 01 / 479 -CH 2 -CH = C CH, OCH, 0 CH ^ ci 3 3 480 ₉ -CH _{-CH) 5} -0-CH-CH = CH ₂ CH ₃ 0CH ₃ 0 CH 481 -CH, -CH 2, -O-CH 2 _-; -CH = CH ₂ CH ₃ OCH ₃ 0 N 482 -cci = cci ₂ ch ₃ OCH ₃ 0 N 483 -CCl = CHCl och ₃ och ₃ 0 CH t 244 to 246 ° 484 -CCl = CC1 ₂ och ₃ och ₃ 0 H 485 -CCl = CC1 ₂ CH ₃ OCH ₃ 0 CH 486 -CCl = CC1 ₂ OCH ₃ OCH, 0 CH 487 -CC1 = OC1 ₂ ch ₃ Cl 0 CH 488 ' -CCl = CC1 ₂ och ₃ Cl 0 N 489 -cf = cf ₂ OCH, Cl 0 N 490 -cf = cf ₂ ^CH 3 Cl 0 CH 491 -ch = cci ₂ OCH, • 0CH ₃ 0 N 492 -ch = cci ₂ ^CH 3 OCH ₃ 0 CH 493 -ch = cci ₂ 0CH ₃ 0CH ₃ 0 CH 494 -ch = cci ₂ ^C 2 ^H 5 0CH ₃ 0 N 495 -cf = cf ₂ ° 2 ^H 6 0CH ₃ 0 N 496 -cci = I want 0CH ₃ OCH ₃ with N 497 -CCl = CHCl CH ₃ OCH ₃ 0 N T. 169 to 172 ° 498 -CCl = CHCl c ₂ h ₅ OCH, 0 N 499 -CCl = CHCl ch ₃ ch ₃ ³ 0 N

Table 5 - continued

Number AND ^R 3 ^R 4 X E Physical data 500 -CCl = CHCl och ₃ Cl 0 CH mp 196-198 ° 501 -CCl = CHCl 0CH ₃ °° 2 ^Η 5 0 N 502 -CCl = CHCl 0CH ₃ OCH ₃ 0 CH - 503 -CCl = CHCl c ₂ h ₅ och ₃ 0 CH 504 -CCl = CHCl ch ₃ Cl 0 CH 505 -CCl = CHCl ch ₃ OCH ₃ with CH 506 -C01 = CHCl OCH, OCH ₃ with CH 507 -cf = cf ₂ ^CH 3 0CH ₃ 0 N 508 -cf = cf ₂ och ₃ 0CH ₃ 0 N 509 -CFS = CF ₂ ^CH 3 och ₃ 0 CH 510 -cf = cf ₂ 0CH ₃ och ₃ 0 CH 511 -ch ₂ -ch = ch ₂ -ch (ch,) ₂ OCH ₃ 0 CH 512 -ch ₂ -ch = ch ₂ OCH ₃ sc ₂ h ₅ 0 CH 513 -CH ₂ -CH = CH ₂ och ₃ sc ₂ h ₅ 0 M 514 -CH ₂ -CH = CH ₂ ^0CH 3 -SCH _{(CH3) 2} 0 N 515 -ch ₂ -ch = ch ₂ Cl CH, 0 N mp 128-130 ° 516 -ch ₂ -ch = ch ₂ CH ₃ Br 0 N 517 -ch ₂ -ch = ch ₂ chf ₂ 0CH ₃ 0 N 518 -ch ₂ -ch = ch ₂ chf ₂ CH, 0 N 519 -CH ₂ -CH = CH ₂ -CH ₂ CF ₃ Cl 0 N 520 -ch ₂ -ch = ch ₂ -CH ₂ CF ₃ OCH ₃ 0 N 521 -ch ₂ -ch = ch ₂ -CH ₂ CF ₃ CH ₃ 0 N 522 -ch ₂ -ch = ch ₂ oc ₂ h ₅ oc ₂ h ₅ 0 N mp 138-142 ° 523 -ch ₂ -ch = ch ₂ oc ₂ h ₅ oc ₂ h ₅ 0 CH 524 -ch ₂ -ch = ch ₂ ^C 2 ^H 5 0CH ₃ 0 N mp 206 ° 525 -ch ₂ -ch = ch ₂ c ₂ h ₅ oc ₂ h ₅ 0 N 526 -ch ₂ -ch = ch ₂ ch ₃ oc ₂ h ₅ 0 N mp 129-131 ° 527 -ch ₂ -ch ₂ ch ₃ ch ₃ 0 CH mp 180-182 ° 528 -ch ₂ -ch = ch ₂ CH ₃ och ₃ 0 CH m.p. 98-100 ° 529 -ch ₂ -ch = ch ₂ CH ₃ Br 0 N 530 -ch ₂ -ch = ch ₂ ch ₂ H 0 N 531 -CH ₂ -CH = CH ₂ ^C 2 ^H 5 Cl 0 CH 532 -ch ₂ -ch = ch ₂ CKj Cl 0 CH mp, 53-154 ° 533 -ch ₂ -ch = ch ₂ CH ₃ SCH, 0 CH 534 -ch ₂ -ch = ch ₂ CH ₃ F 0 CH 535 -ch ₂ -ch = ch ₂ CH ₃ Br 0 CH 536 -CH ₂ -CH = CH ₂ c ₂ h ₅ oc ₂ h ₅ 0 CH 537. -ch ₂ -ch = ch ₂ C ₂ ^h 5 SCH ₃ 0 CH 538 -ch ₂ -ch = ch ₂ CF ₃ ch ₃ 0 CH 539 -ch ₂ -ch = ch ₂ CH ₂ C1 CH ₃ 0 CH 540 -ch ₂ -ch = ch ₂ CH ₂ C1 och ₃ 0 CH 541 -ch ₂ -ch = ch ₂ . QCH, Cl 0 CH mp 173-179 ° 542 -ch ₂ -ch = ch ₂ Cl Cl 0 CH 553 -ch ₂ -ch = ch ₂ 0CH ₃ SCH ₃ 0 CH 544 -ch ₂ -ch = ch ₂ 0CH ₃ -OCH (CH) 0 CH 545 -ch ₂ -ch = ch ₂ ch ₂ f OCH ₃ 0 CH 546 -ch ₂ -ch = ch ₂ ch ₂ f CH ₃ 0 CH 547 -ch ₂ -ch «ch ₂ CF ₃ 0CH ₃ 0 CH 548 -ch ₂ -ch = ch ₂ ^C 2 ^H 5 -OCH _{(CH3) 2} 0 'N 549 -ch ₂ -ch = ch ₂ ^C 2 ^H 5 Cl 0 N 550 -ch ₂ -ch = ch ₂ ^C 2 ^H 5 • sch ₃ 0 N

Table 5 - continued

number AND ^R 3 ^R 4 X E Physical data 551 -CH ₂ -CH = CH ₂ ^C 2 ^H 5 ^CH 3 0 N t. t. 128 to 131 ° 552 -ch ₂ -ch = ch ₂ c ₂ h ₅ ^C 2 ^H 5 0 N 553 -ch ₂ -ch = ch ₂ 0CH ₃ -0CH _{(CH3) 2} 0 N t. t 119 to 120 * 554 -ch ₂ -ch = ch ₂ och ₃ -0CH (CH ₃₎ -CH ₂ CH ₃ 0 N 555 -CH ₂ -CH = CH ₂ CH ₃ -CH (CH _{3) 2} 0 N t. 96-98 556 -ch ₂ -ch = ch ₂ -CH (CH _{3) 2} Cl 0 N. 557 -ch ₂ -ch = ch ₂ -CH _{(CH3) 2} oca ₃ 0 N t. t 124 to 128 ° 558 -ch ₂ -ch = ch ₂ -CH (CH _{3) 2} C ₂ H ₅ 0 N 559 -ch ₂ -ch = ch ₂ -CH _{(CH3) 2} SCH ₃ 0 N 560 -CH ₂ -CH = CH ₂ CH ₂ C1 ch ₃ 0 N 561 -ch ₂ -ch = ch ₂ CH ₂ Cl · OCH, 0 N 562 -ch ₂ -ch = ch ₂ CH ₂ F % 0 TO 563 -ch ₂ -ch = ch ₂ ch ₂ f 0CH ₃ 0 N 564 -ch ₂ -ch = ch ₂ ch ₂ f oc, h ₅ 0 N 565 -CH ₂ -CH = CH ₂ -CH ₂ -0CH ₃ ^C 2 ^H 5 0 N 566 -ch ₂ -ch = ch ₂ -CH ₂ -SCH ₃ 0CH ₃ 0 N 567 -ch ₂ -ch = ch ₂ -CH ₂ -SCH ₃ ^CH 3 0 N 568 -ch ₂ -ch = ch ₂ -CH ₂ -SCH ₃ SCH, 0 M 569 -ch ₂ -ch = ch ₂ -CH ₂ -SCH ₃ Cl 0 N 570 -ch ₂ -ch = ch ₂ -CH ₂ -SCH ₃ C ₂ H ₅ 0 N 571 -ch ₂ -ch = ch ₂ SCH ₃ Cl 0 N 572 -CH ₂ -CH = CH ₂ SCH ₃ OCH ₃ 0 H 573 -ch ₂ -ch = ch ₂ sch ₃ oc ₂ h ₅ 0 N CH, / 3 574 -ch ₂ -ch = ch ₂ SCH ₃ -OCH \ ch ₃ 0 * N 575 -ch ₂ -ch = ch ₂ -OCH (CH3) ₂ Cl 0 N 576 -ch ₂ -ch = ch ₂ cf ₃ OCiíj 0 N 577 -ch ₂ -ch = ch ₂ CF ₃ CH ₃ 0 N 578 -CH ₂ -CH = CH ₂ CF ₃ oc ₂ h ₅ 0 N 579 -CH ₂ -CH = CH ₂ CC1, och ₃ 0 N 580 -ch ₂ -ch = ch ₂ CC1 ₃ SCH ₃ 0 N 581 -CH ₂ -CH = CH ₂ ^CiI 3 Cl 0 N t. t., 28 to 130 ° 582 -CH ₂ -CH = CH ₂ OCH ₃ Cl 0 N 583 -ch ₂ -ch = ch ₂ och ₃ F 0 N 584 -ch ₂ -ch = ch ₂ och ₃ Br 0 N 585 -CH ₂ -CH = CH ₂ CH ₃ P 0 N 586 -CH ₂ -CH = CH ₂ OCH ₃ OCH, 0 CH t. t 184 to , 86 ° 587 -ch ₂ -ch = ch ₂ CH ₃ ^CH 3 0 N t. t 139 to 141 ° 588 -ch ₂ -ch = ch ₂ 0CH ₃ qc ₂ h ₅ E N 589 -ch ₂ -ch = ch ₂ och ₃ OC ₂ ^H 5 0 CH 590 -CH ₂ -CH = CH ₂ CH ₂ OCH ₃ CH, OCH, OCH ₃ OCH ₃ 0 CH 591 -ch ₂ -ch = ch ₂ 0 N 592 -ch ₂ -ch = ch ₂ ^C 2 ^H 5 OCH ₃ 0 CH 593 -ch ₂ ch = ch ₂ ch ₂ and ₃ ch ₃ 0 N 594 -CH ₂ -CH = CH ₂ ^CH 3 OCH ₃ with N 595 -ch ₂ -ch = ch ₂ och ₃ OCH ₃ 0 N t. t. 148 to 149 ° 496 -CH = CHCl CH ₃ och ₃ 0 N 597 -CH = CHCL CH ₃ OCH ₃ with N

Table 5 - continued

Number AND ^R 3 ^R 4 X E Physical data 598 -OCIfCHCI ch ₃ OCH ₃ 0 CH mp 208-209 ° 599 -ch = cci ₂ CH ₃ OCH ₃ 0 N 600 -CCl = CHCl och ₃ OCH ₃ 0 N 601 -CH ₂ -CH = CH ₂ CH ₃ ^0CH 3 . 0 N mp 146-147 ° 602 -CH ₂ -CH = CH ₂ OCH ₃ 0CH ₃ with N

Table 5a

SO.-NH-C-NH

R.

³ y / \ V

X-A

Number AND ^R 3 ^R 4 X E 650 -ch ₂ -ch = ch ₂ CH ₃ OCH ₃ 0 N 651 -ch ₂ -ch ₂ -och ₃ ch ₃ och ₃ 0 N 652 -CCl = CHCl CH ₃ OCH ₃ 0 N 653 -CH ₂ -OCH ₃ CH ₃ och ₃ 0 N 654 -CH ₂ -CH = CH-CH ₃ OCH ₃ OCH ₃ 0 N 655 -CH ₂ - (CH ₃ ) = CH ₂ CH ₃ OCH ₃ 0 N

Table 6

2.,

X-A

O ¹¹ N CH.

SO 2 NH-C-NH-f · γ ³ Νγ £ OCH.

Number AND Position X-A ^R 1 ^R 2 X E Physical data 701 -CH ₂ -CH = CH ₂ 5 _2-CH3 H 0 N 702 -ch ₂ -ch = ch ₂ 5 _2-CH3 H O CH * 703 -CH ₃ -C = CH ₂ CH ¹¹ 5 _2-CH3 H O CH 704 -CH ₂ -C = CH ₂ 5 _2-CH3 H 0 N 705 -CH ₂ -CH = CH-CH ₂ 5 2-0 ^ H O N 706 -CH ₂ -CH = CH-CH ₂ Cl 1 5 _2-CH3 H 0 CH 707 -CH ₂ -C = CH ₂ Cl 5 _2-CH3 H 0 CH 708 | -CH ₂ -C = CH ₂ - _? 5 _2-CH3 H 0 H 709 -ch ₂ -ch = ch ₂ 5 2-C1 H 0 N

Table 6 continued

Number AND Position X-A ^R 1 ^R 2 X E Physical data 710 -ch ₂ -ch = ch ₂ Cl 1 5 2-C1 H O CH 711 -CH ₂ -C = CH ₂ ^; 5 2-C1 H 0 CH 712 -CH ₂ -C »CH ₂ P ³ 5 2-C1 H 0 N 713 -CH ₂ -C = CH _{2 1} ^H 3 · 5 2-CI H 0 N 714 -CH ₂ -O = CH ₂ 5 2-C1 H ' 0 CH 715 -CH ₂ -O-CH ₃ 5 2-C1 H 0 CH 716 -CH ₂ -O-CH ₃ 5 2-C1 H 0 N 717 -CH ₂ -S-CH ₃ 5 2-C1 H 0 N 718 -CH ₂ -S-CH ₃ 5 2-C1 H 0 CH 719 -CH ₂ -CH = CH-CH ₃ 5 2-C1 H 0 CH 720 -ch ₂ -ch = ch-ch ₃ 5 2-C1 H 0 N 721 -CH _? -CH _? -0CH, 5 2-C1 H 0 N 722 -CHp-CHp-OCH3 5 2-C1 H 0 CH 723 -ch ₉ -oc ₂ h _b 5 2-C1 H 0 N 724 -CH _? -OC ,, H, j 5 2-C1 H 0 CH 725 -CHp-CHp-SCH2 5 2-C1 H 0 CH 726 -CH _? -CH 2 - SCH 2 5 2-C1 H 0 N 727 -ch ₂ -ch = ch ₂ 3 _2-CH3 H 0 N 728 -ch ₂ -ch = ch ₂ f ^H 3 3 2-CH 3 H 0 CH ¢ 29 -ch ₂ -c = ch ₂ ° ^H 3 3 _2-CH3 H 0 CH 730 -ch ₂ -c = ch ₂ 3 2-CH ₃ 2-OCH ₃ H 0 N 731 -ch ₂ -ch = ch ₂ 3 H 0 N 732 -ch ₂ -ch = ch ₂ Γ ³ 3 2-OCH ₃ H 0 CH 732 -CH ₂ -C = CH ₂ P ³ 3 2-OCH ₃ H 0 CH 734 -CH ₂ -C = CH ₂ Cl 1 3 2-0CH ₃ H 0 N 735 -CH ₂ -C = CH ₂ Cl 3 2-0CH ₃ H 0 N 736 | -CH ₂ -C = CH ₂ 3 2-OCH ₃ H 0 CH 737 -ch ₂ -ch = ch-ch ₃ 3 2-0CH ₃ H 0 CH 738 -CH ₂ -CH = CH-CH ₃ 3 2-OCH ₃ H 0 N 739 -CH ₂ -CH = CH ₂ 5 2-OCH ₃ H 0 N

Table 6 - continued

Number AND Position X-A ^R 1 r ₂ X E Physical data 740 -ch ₂ -ch = ch ₂ 5 2-OCH ₃ H O CH f ^H 3 74, -CH ₂ -O = CH ₂ 5 2-OCH ₃ H O CH f * 3 742 -CH ₂ -C = CH ₂ 5 2-0CH ₃ H O N 743 -CH ₂ -CH = CH-CH ₃ 5 2-OCH ₃ H O N 744 -CH ₂ -CH = CH-CH ₃ 5 2-OCH ₃ H O CH Cl 745 | -CH ₂ -C = CH ₂ 5 2-OCH ₃ H 0 CH Cl | 746 -CH ₂ -C = CH ₂ 5 2-OCH ₃ H 0 N 747 748 -CH ₂ -CH = CH ₂ -ch ₂ -ch = ch ₂ 3 3 5-Br 5-Br ₃ 2-0CH _2-OCH3 0 0 N CH t 258 156 to to 259 ° 157 ° ^GH 3 749 -ch ₂ -c = ch ₂ 3 5-Br 2-OCH ₃ 0 CH CH, | ³ 750 -CH ₂ -C = CH ₂ 3 5-Br 2-OCH ₃ 0 N 751 -CH ₂ -CH = CH ₂ 3 5-cooch ₄ 2-0CH ₃ 0 N 752 -CH ₂ -CH = CH ₂ 3 5-COOCH ₃ 2-OCH ₃ 0 CH ^GH 3 753 -ch ₂ -c = ch ₂ 3 5-COOCH ₃ 2-OCH ₃ 0 CH CH, I ³ 754 -CH ₂ -C = CH ₂ 3 5-COOCH ₃ 2-OCH ₃ 0 N 755 -CH ₂ -CH = CH-CH ₃ 3 5-COOCH ₃ 2-OCH ₃ 0 N 756 -CH ₂ -CH = CH-CH ₃ 3 5-COOCH ₃ 2-OCH ₃ 0 CH 757 -CH ₂ -CH = CH ₂ 2 5-NO ₂ 3-CF ₃ 0 N 758 -CH ₂ -CH = CH ₂ 2 5-NO ₂ 3-CF, 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 Γ ³ 761 -CH-C = CH ₂ 2 5-NO ₂ 3-C1 0 N Γ ³ 762 -CH-C = CH ₂ 2 5-NO ₂ 3-C1 0 CH 763 -ch ₂ -ch = ch ₂ 2 5-CF ₃ 3-NOg 0 CH 764 -ch ₂ -ch = ch ₂ 2 5-CF ₃ 3-NO ₂ 0 N 765 -ch ₂ -ch = ch ₂ 2 _5-CH3 3-CH ₃ 0 N 766 -ch ₂ -ch = ch ₂ 2 _5-CH3 3-CH ₃ 0 CH 767 -ch ₂ -ch = ch-ch ₃ 2 _5-CH3 3-CH ₃ 0 CH 768 -ch ₂ -ch = ch-ch ₃ 2 5-CH 3-CH, 0 N 769 -CH ₂ -CH = CH-CH ₃ 2 5-C1 3-NO ₂ 0 N

Table 6 - continued

Number A

Location R, X-A

R ₂ XE Physical Days

770 -CH ₂ -CH = CH-CH ₃ 2 5-C1 3-NO ₂ 0 CH 771 -ch ₂ -ch = ch ₂ 2 5-C1 3-NO ₂ O CH 772 -ch ₂ -ch = ch ₂ 2 5-C1 3-NO ₂ O N 773 -ch ₂ -ch = ch ₂ 2 5-C1 3-C1 0 N 774 -CH ₂ -CH = CH ₂ 2 5-C1 3-C1 O CH 775 -ch ₂ -ch ₂ -och ₃ 2 5-C1 3-C1 0 CH 776 -CH ₂ -CH ₂ -OCH ₃ 2 5-C1 3-C1 O N 777 ' -CH _? -0CH ₃ 2 5-C1 3-C1 0 N 778 -CH ₂ -OCH ₃ ^ 3 2 5-C1 3-C1 0 CH 779 -CH ₂ -C = CH ₂ 2 5-C1 3-C1 0 CH 780 -CH ₂ -C = CH ₂ 2 5-C1 3-C1 O N 781 -CH ₂ CH = CH _of 2 5-Br ₃ O 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 _? -ch = ch ₂ 3 5-Br 2-OCH ₃ 0 N 785 -ch ₂ -ch = ch ₂ 2 5-cooch ₄ 3-0CH ₃ 0 N 786 -ch ₂ -ch = ch ₂ 2 5-COOCH ₃ 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 ch ₃ 3 5-COOCH ₃ 2-OCH ₃ 0 H 739 -ch ₂ -c = ch ₂ ? ^H 3 3 5-cooch ₄ 2-0CH ₃ 0 N 790 -ch ₂ -c = ch ₂ 3 5-COOCH ₃ 2-OCH, 0 CH 791 -ch ₂ -ch = ch ₂ 2 _5-CH3 3-Br 0 CH 792 -ch ₂ -ch = ch ₂ 2 _5-CH3 3-Br 0 N 793 -CH ₂ -OCH ₃ 2 _5-CH3 3-Br 0 N 794 -CH ₂ -OCH ₃ 2 _5-CH3 3-Br 0 CH 795 -ch ₂ -ch = ch ₂ 2 5-Br 3-NO ₂ 0 N 796 -ch ₂ -ch = ch ₂ 2 5-Br 3-NO ₂ 0 CH 797 -ch ₂ -ch = ch ₂ 2 5-C1 3-Br 0 CH 798 -ch ₂ -ch = ch ₂ Γ ³ 2 5-C1 3-Br 0 N 799 -ch ₂ -c = ch ₂ CH, ¹³ 2 5-C1 3-Br 0 TO 800 -ch ₂ -c = ch ₂ 2 5-C1 3-Br 0 CH 801 -CH ₂ -CH ₂ -O-CH ₃ 2 5-C1 3-Br 0 CH 802 -CH ₂ -CH ₂ -O-CH ₃ 2 5-C1 3-Br 0 M 803 -CH ₂ -O-CH ₃ 5 2-NO ₂ H 0 CH 804 -CH ₂ -O-CH ₃ 3 H H with CH 805 -CH ₂ -CH ₂ -OCH ₃ 2 5-OC ₂ H ₄ -OCH ₃ H 0 N 806 -ch ₂ -ch = ch ₂ 2 5- and _2- ch = ch ₂ H 0 N 807 -CH ₂ -OCH ₃ 2 5-0CH ₂ -0CH ₃ H 0 N

/

Table 6 - continued

Number AND Position X-A ^R 1 r ₂ X E Physical data 808 -CHp-CHp-OCH3 2 5-S-CpH 2 -OCH 3 H WITH N 809 . -ch ₂ -sch ₃ 2 5-S-CH ₂ -SCH ₃ H WITH N 810 -ch ₂ so-ch ₃ 2 _5-S-CH2 -SOCH ₃ H WITH M 81 1 -CH ₂ -SO ₂ -CH ₃ 2 5-CH ₂ -SO ₂ -CH ₃ H with N

Example 6

a) N- (2-difluoromethoxyphenylsulfonyl) phenylcarbamate

A solution of 4.5 g of 2-difluoromethoxyphenylsulfonamide in 5 ml of absolute dimethylformamide is added dropwise to a suspension of 0.84 g of a 57.5% sodium hydride dispersion in 5 ml of absolute dimethylformamide, cooled to 0-10 ° C. To complete the evolution of hydrogen, the reaction mixture was heated to 25 ° C with stirring. After the evolution of hydrogen had ceased and the reaction mixture was cooled to -30 ° C, a solution of 4.7 g of diphenyl carbonate in 5 ml of absolute dimethylformamide was added, and then the reaction mixture was stirred for 18 hours while warming to 25 ° C. After pouring the reaction solution into a mixture consisting of 11 ml of 2N hydrochloric acid and 100 g of ice, the precipitated product is taken up in ethyl acetate. Drying and evaporation of the ethyl acetate phase and recrystallization from methanol gave 5.6 g of N- (2-difluoromethoxyphenylsulfonyl) phenylcarbamate as colorless crystals, m.p. 115-117 ° C.

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

A solution of 5.4 g of N- (2-difluoromethoxyphenylsulfonyl) phenylcarbamate and 2.42 g of 2-amino-4-ethyl-6-methoxy-1,3,5-triazine in 60 ml of absolute dioxane is refluxed for 5 hours and then pour into 600 ml of ice water. The precipitated product is taken up in ethyl acetate.

The oil obtained after washing with water, drying and evaporation of the ethyl acetate phase is redissolved in ethyl acetate and washed five times with saturated sodium bicarbonate solution. The combined aqueous phases were acidified with dilute hydrochloric acid and extracted with ethyl acetate.

After drying and evaporating the ethyl acetate phase and recrystallizing from methanol, 5.1 g of N- (2-difluoromethoxyphenylsulfonyl) -N '- (4-ethyl-6-methoxy-1,3,5-triazin-2-yl) urea is obtained. mp 114-116 ° C.

Example 7

N- (2-Difluoromethoxyphenylsulfonyl) -N '- (4-chloro-6-methylpyrimidin-2-yl) urea

In analogy to Example 9c), N- (2-difluoromethoxyphenylsulfonyl) -N3 (4-chloro-6-methylpyrimidin-2-yl) is obtained from N- (2-difluoromethoxyphenylsulfonyl) isocyanate by treatment with 2-amino-4-chloro-6-methylpyrimidine. 190 DEG-191 DEG.

Example 8

a) N- (2-Difluoromethoxyphenylsulfonyl) -N- (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 was added 4.5 g of 2-difluoromethoxyphenylsulfonamide. After refluxing for 5 hours, the resulting clear solution is poured into 500 ml of ice water. The precipitated product was extracted with ethyl acetate. Drying and concentration of the organic phase yields a crystallizate, m.p. 105 DEG-107 DEG C., which is 8.5 g of dioxane adduct and N- (2-difluoromethoxyphenylsulfonyl) -N- (4,6-dichloro-1,3,5-triazine) -2-yl) urea in a 1: 1 ratio.

b) N- (2-difluoromethoxyphenylsulfonyl) -N '- (4,6-ethoxy-1,3,5-triazin-2-yl) urea

To a solution of 5.5 g of the N- (2-difluoromethoxyphenylsulfonyl) -N '- (4,6-dichloro-1,3,5-triezin-2-yl) urea and dioxane adduct obtained according to Example 8a) in 10 ml of absolute ethanol A solution of 1.9 g of sodium ethoxide in 10 ml of absolute ethanol is added dropwise over 15 minutes. After two hours under reflux, the reaction mixture was evaporated and the residue was dissolved in 200 ml of ice water. Acidification of the solution with dilute hydrochloric acid gave 3.2 g of N- (2-difluoromethoxyphenylsulfonyl) -N '- (4,6-diethoxy-1,3,5-triazin-2-yl) urea as colorless crystals, m.p. to 118 ° C.

Example 9

a) N- (2-pentafluoroethoxyphenylsulfonyl) -N'-methylurea

The 2-pentafluoroethoxyphenylsulfonamide obtained according to Example 4b) is suspended in 400 ml of methylene chloride. Methyl isocyanate (16.3 g) was added and triethylamine (28.2 g) was added dropwise over 15 minutes. A clear solution is formed. Complete evaporation, dissolution of the residue in 5% sodium carbonate solution and re-acidification with 10% hydrochloric acid gave 74.6 g of N- (2-pentafluoroethoxyphenylsulfonyl) -N'-methylurea, m.p. 177-179 ° C.

b) 2-pentafluoroethoxyphenylsulfonyl isocyanate

74.6 g of N- (2-pentafluoroethoxyphenylsulfonyl) -N'-methylurea are suspended in 1300 ml of chlorobenzene and the solvents are dried by azeotropic distillation of about 100 ml of solvent. 48 g of phosgene are then introduced at 120 DEG-130 DEG C. over a period of 3 hours. Completely distilling off the chorbenzene gave 65 g of 2-pentafluoroethoxyphenylsulfonyl isocyanate as an almost colorless oil.

c) N- (2-pentafluoroethoxyphenylsulfonyl) -N '- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) urea

3.2 g of 2-pentafluoroethoxyphenylsulfonylisocyanate and 1.4 g of 2-amino-4-methoxy-6-methyl-1,3,5-triazine are stirred together with 40 ml of absolute dioxane for 3 hours at a temperature of 90-100 °. C. The solution was then cooled to 20 ° C, filtered and the filtrate evaporated to about 1/4 of the original volume. 3.3 g of N- (2-pentafluoroethoxyphenylsulfonyl) -N '- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) urea crystallize out of the residue with 50 ml of ether, m.p. 159 [deg.] C.

He did

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

A solution of 5.4 g of N- (2-difluoromethoxyphenylsulfonyl) phenylcarbamate and 2.2 g of 2-amino-4-methoxy-6-methyl-1,3,5-trlazine in 60 ml of absolute dioxane is refluxed for 5 hours and then pour into 600 ml of ice water. The precipitated product is taken up in ethyl acetate.

After washing with water, drying and evaporating the ethyl acetate phase, an oil is obtained which is redissolved in ethyl acetate and this solution is washed five times with a saturated sodium bicarbonate solution. The combined aqueous phase was acidified with dilute hydrochloric acid and extracted with ethyl acetate. After drying and evaporating the ethyl acetate phase and recrystallizing the residue from methanol, 5.0 g of N- (2-difluoromethoxyphenylsulfonyl) -1 '- (4-mothoxy-6-methyl-1,3,5-triazin-2-yl) urea is obtained. mp 132-134 ° C.

Example 11

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

In an analogous manner to that described in Examples 3a to b), 2-difluoromethylthiophenylsulfonamide is obtained from 2-difluoromethylthioaniline via sulfonyl chloride, m.p. 141-142 ° C. This sulfonamide is converted to the corresponding N- (2-difluoromethylthiophenylsulfonyl) phenyl carbamate and reacted with 2-amino-4-methoxy-6-methyl-1,3,5-triazine to give N- (2-difluoromethylthiophenylsulfonyl) -N'- 169 DEG-172 DEG C. (4-methoxy-6-methyl-1,3,5-triazin-2-yl) urea.

Example 1 a d, 2

N- (2-difluoromethoxyphenylsulfonyl) -N '- (4,6-dimethoxy-1,3,5-triazin-2-yl) urea

To a solution of 5.5 g of the N- (3-difluoromethoxyphenylsulfonyl) -N- (4,6-dichloro-1,3,5-triazin-2-yl) urea / dioxane adduct obtained according to Example 7a), A solution of 1.5 g of sodium methoxide in 10 ml of absolute methanol was added dropwise over 5 minutes to 0 ml of absolute methanol. After refluxing for 2 hours, the reaction mixture was evaporated and the residue was dissolved in 200 ml of ice water. Acidification of the solution with dilute hydrochloric acid gave 3.2 g of N- (2-difluoromethoxyphenylsulfonyl) -N * - (4,6-dimethoxy-1,3,5-triazin-2-yl) urea as colorless crystals, m.p. 37 C.

The compounds of formula (I) shown in the following table are prepared in an analogous manner:

Table 7 ¹¹

SO3-NH-C-NH-phi · ³

ΝγΕ

Number AND E ^R 3 ^R 4 X Physical data 901 chf ₂ N oc ₂ h ₅ °° 2 ^Η 5 0 t 117 to 118 ° 902 chf ₂ CH oc ₂ h ₅ oc ₂ h ₅ 0 146 152 ° 903 chf ₂ N CH ₃ NOC ₄ H ₉ 0 south of 110 ° 904 CP ₃ N oc ₂ h ₅ oc ₂ h ₅ 0 905 CF, CH OČ JL oc ₂ h ₅ 0 ' 906 cf ₃ TO CH ₃ η °° 4 ^Η 9 0 907 -cf ₂ -chf ₂ N 0¾ oc ₂ h ₅ 0 103 to 106 ° 908 -cf ₂ -chf ₂ CH 0¾ oc ₂ h ₅ 0 909 -cf ₂ -chf ₂ N CH ₃ ^C 2 ^H 5 0 147 to 148 ° 910 -cf _{2 I} want N 0¾ OC ₂ ^H 5 0 t 129 to 131 ° 91, -cf ₂ -chfci CH oc ₂ h ₅ oc ₂ h ₅ 0 9.2 -cf ₂ -chfci N CH ₃ °° 4 ^Η 9 0 913 -CF ₂ -CHFBi » N OC oc ₂ h ₅ 0 914 -CFg-CKEBr CH oc ₂ H ₅ oc ₂ h ₅ 0 915 -CFgCHFBr N CH ₃ ° 0 ₄ ^Η 10 0 9.6 chf ₂ N CC1 ₃ CC1 ₃ 0 137 to 145 ° 917 - ° 2 ^H 6 N OCH ₃ ° ch ₃ 0 t 185 to 187 ° 9.8 -ck ₂ -ccif ₂ N OCH ₃ OCH ₃ 0 919 -chf ₂ N ^C 2 ^H 5 OCH ₃ 0 t. 114 to 16 ° 920 shf ₂ H ^C 2 ^H 5 oc ₂ h ₅ 0

Table 7 - continued

Islo AND E «3 ^R 4 X Physical data 921 chf ₂ N ^C 2 ^H 5 n-OC-jH? 0 922 CHFj TO c ₂ h ₅ n-OC ₄ H _g 0 923 ^C 2 ^H 5 N c ₂ h ₅ och ₃ 0 t. 153 to 154 ° 924 ^C 2 ^F 5 N CH ₃ och ₃ 0 145 to 149 ° 925 ^g 2 ^f 5 M CH ₃ oc _? h ₅ 0 926 ^g 2 ^F 5 N oc ₂ h ₅ OC _q H, 25.5 0 927 ^G 2 ^F 5 CH ch ₃ ' ch ₃ 0 T. 173 to 175 ° 928 ^G 2 ^F 5 CH c ₂ h ₅ 0CH ₃ 0 929 c ₂ f ₅ CH cH ₃ OCH ₃ 0 T. 165 up to 170 ^u 930 ^C 2 ^F 5 CH 0CH ₃ och ₃ 0 93 ’ ^G 2 ^F 5 N ch ₃ CH ₃ 0 932 ^GHF 2 N Cl Cl 0 105 to 107 ° 933 -CFg-CHFBr N CH ₃ n-OC ₄ H ₉ with with 1 mol of dioxane 934 -CF _o -CF ₂ Cl N OCH ₃ och ₃ with 935 -CF ₂ -CBrF ₂ N och ₃ och ₃ with 936 chf ₂ N CC1 ₃ CC1 ₃ with 937 chf ₂ N ^C 2 ^H 5 OCH ₃ with 146 to 147 ° 938 chf ₂ N ^C 2 ^H 5 OCH ₃ with 939 chf ₂ Ν ' ^C 2 ^H 5 och ₃ SO ₂ 940 ^C 2 ^F 5 N OCH ₃ OCH ₃ with 941 chf ₂ N oc h ₅ oc ₂ h ₅ with 942 chf ₂ N ch ₃ n-OC ₄ H ₉ with 943 chf ₂ CH oc ₂ h ₅ oc ₂ h ₅ with 944 ^OBJECTIVE 2 N oc ₂ h ₅ oc ₂ h ₅ Sat 945 chf ₂ CH oc ₂ h ₅ oc ₂ h ₅ Sat 946 chf ₂ N oc ₂ h ₅ Sat ₂ 947 chf ₂ CH °° 2 ^Η 5 oc ₂ h ₅ ^S0 2 948 chf ₂ N CH ₃ n-OC ₄ H ₉ SO ₂ 949 CF ₃ N oc ₂ h ₅ ^OC 2 ^H 5 WITH 950 CF ₃ CH oc ₂ h ₅ oc ₂ h ₅ WITH 951 cf ₃ N ch ₃ ° c ₃ h ₉ WITH 952 -cf ₂ -chf ₂ N oc ₂ h ₅ oc ₂ h ₅ with 953 -cf ₂ -chf ₂ CH C ₂ H ₅ oc ₂ h ₅ with 954 -cf ₂ -chf ₂ N CH ₃ n-OC2H3 with 955 -cf ₂ -chfci N °° 2 ^Η 5 oc ₂ h ₅ with 956 -cf ₂ -chfci CH oc ₂ h ₅ oc ₂ h ₅ with 957 -cf ₂ -chfci N ch ₃ NOC ₄ H ₉ with 958 -CFg-CHFBr N och ₂ ch ₇ OCH ₂ CH 2 with 959 -CF ₂ -CHFBr CH oc ₂ h ₅ OC-jHg with 960 ^G 2 ^F 5 CH ch ₃ Cl 0 961 ^C 2 ^F 5 N OCH ₃ Cl 0 t. 153 to 155 ° 962 in', CH CH ₃ F 0 963 ^C 2 ^F 5 N OCH ₃ OCH ₃ 0 t 185 to 187 ° 964 “Λ N och ₃ oc ₂ h ₅ 0 965 ^G 2 ^F 5 N ch ₂ ci OCH ₃ 0 966 ^C 2 ^F 5 N -chcch,) _? OCH, 0 967 c ₂ f H ^G 2 ^H 5 Cl 0 968 ^G 2 ^F 5 N c ₂ ^h 5 CH ₃ 0 969 ^G 2 ^F 5 ít -CHpOCH2 0CH ₃ 0 970 ^G 2 ^F 5 CH -ch ₂ och _? och ₃ 0 971 ^C 2 ^F 5 H 0CH ₃ -OCH _{(CH3) 2} 0

Table 7 - continued

Number A E í * 4 X Physical data

972 c ₂ f ₅ N och ₃ SCH ₃ 0 973 ^C 2 ^F 5 N ch ₃ 0CH ₃ with 974 ^C 2 ^F 5 CH CH ₃ 0CH ₃ with 975 C ₂ ^P 5 M OCH ₃ OCH ₃ with 976 CFgBr N CH ₃ och ₃ with 977 CF ₂ Br N OCH ₃ ^0Object 3 with 978 CF ₂ Br CH CH ₃ och ₃ with 979 CFgBr CH och ₃ 0CH ₃ with 980 CF ₂ Br CH CH ₃ GH ₃ with 981 CF ₂ Br N ^C 2 ^H 5 OCH ₃ with 982 CFgBr N CH ₃ 0CH ₃ 0 983 CFjBr N 0CH ₃ 0CH ₃ 0 984 CFgBn N ^C 2 ^H 5 OCH ₃ 0 985 CFgBr CH ch ₃ OCH ₃ 0 986 CFgBr CH 0CH ₃ och ₃ 0 987 cf ₃ CH CH ₃ Cl 0 988 CF, H och ₃ -OCH (CH) 0 989 cf ₃ N Cl 0CH ₃ 0 990 cf ₃ N ^C 2 ^H 5 0CH ₃ 0 991 cf ₃ N -CH (CH _{3) 2} OCH ₃ 0 992 CF ₃ N -0CH _{(CH3) 2} OCH, 0 993 -ch ₂ -cf ₃ CH CH ₃ Cl 0 994 -ch ₂ -cf. N 0CH ₃ Cl 0 995 CF ₂ C1 CH -CH (CH _{3) 2} 0CH ₃ 0 996 CF ₂ C1 CH 0CH ₃ -sc ₂ h ₅ . 0 997 CF ₂ C1 N OCH ₃ -sc ₂ h ₅ 0 998 cf ₂ ci N 0CH ₃ -SCH _{(CH3) 2} 0 999 CF ₂ C1 N CC1 ₃ ch ₃ 0 1 000 CF ₂ C1 N CH ₃ Br 0 1 001 CFgCl N chf ₂ 0CH ₃ 0 1 002 CF ₂ C1 N chf ₂ CH- 0 1 003 cf ₂ Ci M CH ₂ CF ₃ Cl 0 1 004 cf ₂ ci N CH ₂ CF ₃ ° ch ₃ 0 1 005 cf ₂ ci N CH ₂ CF ₃ ch ₃ 0 1 006 cf ₂ ci N oc ₂ h ₅ oc ₂ h ₅ 0 1 007 CF ₂ C1 CH oc ₂ h ₅ oc ₂ h ₅ 0 1 008 CF ₂ C1 N c ₂ H OCH ₃ 0 1 009 cf ₂ ci N ^C 2 ^H 5 oc ₂ h ₅ 0 1 010 cf ₂ ci N CH ₃ 0CH ₃ 0 1 01 1 cf ₂ ci CH CH ₃ CH ₃ 0 1 013 CF ₉ C1 CH CH ₃ OCH, 0 1 014 CFgCl N CH ₃ Br 0 1 015 CFgCl N CH ₃ H 0 1 0,6 CF ₂ C1 CH c ₂ h ₅ Cl 0 1 017 cf ₂ ci CH CH ₃ Cl 0 1 018 cf ₂ ci CH CH ₃ SCH, 0 I 019 CF, C1 CH CH ₃ F 0 1 020 CFgCl CH CH ₃ Br 0 1 02, CF ₂ C1 CH ^C 2 ^H 5 oc ₂ h ₅ 0 1 022 CFgCl CH ^G 2 ^H 5 SCH ₃ 0 1 023 CF ₂ .C1 CH CF ₃ ch ₃ . 0

224000 50

Table 7 - continued issue AE ^K 3 ^R 4 ^x Physical data

1 024 ca ₂ gi CH ch ₂ ci CH ₃ 0 1 025 cf ₂ ci CH ch ₂ ci och ₃ 0 1 026 cf ₂ ci CH och. Cl 0 1 027 cf ₂ ci CH Cl Cl 0 1 028 CF ₂ C1 CH OCHy SCH ₃ 0 1 029 cf ₂ ci CH OCH ₃ -OCH _{(CH3) 2} 0 1 030 CFgCl CH ch ₂ f OCH ₃ 0 1 031 CF ₂ C1 CH ch ₂ f ch ₃ . 0 1 032 cf ₂ ci CH cf ₃ OCH ₃ 0 1 033 cf ₂ ci N ^C 2 ^S 5 OCH _{(CH3) 2} 0 .1 034 čf ₂ ci N ^G 2 ^H 5 Cl 0 1 035 cf ₂ ci M ^C 2 ^H 5 SCH, 0 1 036 cf ₂ ci N ^G 2 «5 ch ₃ . 0 1 037 ’ cf ₂ ci N ° 2 ^H 6 ^C 2 ^H 5 0 1 038 cf ₂ ci N och ₃ -OCHCCH ₃ ) ₂ 0 1 039 cf ₂ ci N ° ch ₃ -OCH-CH ³ CH ₂ CH ₃ 0 1 040 cf ₂ ci. H ch ₃ -CH _{(CH3) 2} 0 1 041 CF ₂ C1 N -CH (CH _{3) 2} Cl 0 1 042 ca ₂ ci ' N -CH (CH _{3) 2} OCH ₃ 0 1 043 CF ₂ C1 N -CH (CH _{3) 2} oc _j h ₅ 0 1 044 cf ₂ ci N -CH (CH _{3) 2} SCH ₃ 0 1 045 cf ₂ ci H CH ₂ C! CH ₃ 0 1 046 cf ₂ ci N CHgCl och ₃ 0 1 047 CFgCl N CH ₂ F ch ₃ 0 1 048 CF ₂ C1 N ch ₂ f OCH ₃ 0 1 049 cf ₂ ci N ch ₂ f oc ₂ h ₅ 0 1 050 CF ₂ C1 N -CH ₂ OCH ₃ ^C 2 ^H 5 0 1 051 cf ₂ ci N -CH ₂ SCH ₃ OCH, 0 1 052 CFgCl N . -CH ₂ SCH ₃ CH ₃ 0 1 053 CF ₂ C1 N -CH ₂ SCH ₃ SCH, 0 1 054. cf ₂ ci H -CH ₂ SCH ₃ Cl 0 1 055 cf ₂ ci TO -ch ₂ sch ₃ oc ₂ h ₅ ' 0 1 056 . CF ₂ C'l N sch ₃ Cl 0 1 057 cf ₂ ci N sch ₃ och ₃ 0 1 058 CFgCl N sch ₃ oc ₂ h ₅ 0 1 059 cf ₂ ci N SCH ₃ -OCH _{(CH3) 2} 0 1 060 CFgCl. N -OCH _{(CH3) 2} Cl 0 1 061 CF ₂ C1 N CF ₃ 0CH ₃ 0 1 062 CFgCl N CF ₃ CH ₃ 0 1 063 CF ₂ Cl ' N CF ₃ oc ₂ h ₅ 0 1 064 OFgCl N CC1 ₃ OCH ₃ 0 1 065. CF ₂ C1 N CC1 ₃ SCH ₃ · 0 1 066 cf ₂ ci N CH ₃ Cl 0 1 067 CF ₂ C1 N OCH ₃ Cl 0 1 068 CFgCl N OCH ₃ F 0 1 069 CF ₂ C1 N och ₃ Br ’ 0 1 070 cf ₂ ci N ch ₃ F 0 1 071 cf ₂ ci CH och ₃ 0CH ₃ with 1 072 cf ₂ ci N ch ₃ CH ₃ with

Table 7 - continued

Number AND E ^R 3 ^R 4 ' X Physical data i 073 CFgCl N OCH ₃ OC ₂ H WITH 1 074 CFgCl CH -CH _? 0CH ₃ OCH ₃ WITH 1 075 cf ₂ ci N och ₃ 0CH ₃ WITH 1 076 cf ₂ ci CH ^C 2 ^H 5 OCH ₃ with 1 077 cf ₂ ci N c ₂ h ₅ CH ₃ with 1 058 cf ₂ ci N ch ₃ 0CH ₃ Sat 1 079 CF ₂ C1 N 0CH ₃ OCH ₃ Sat 1 080 cf ₂ ci CH ch ₃ OCH ₃ Sat 1 081 cf ₂ ci CH och ₃ 0CH ₃ Sat i 082 CFgCl N ch ₃ OCH ^S0 2 1 083 CFgCl N ^CH 3 CH ₃ SOg 1 084 cf ₂ objectives N och ₃ OCH ₃ SO ₂ 1 085 CFgCl CH CH ₃ OCH ₃ SO ₂ 1 086 CFgCl CH CH ₃ CH ₃ SO ₂ 1 087 CF ₂ C1 CH OCH ₃ OCH ₃ SO ₂ 1 088 -CF ₂ -CF ₃ N OCH ₃ -OCH _{(CH3) 2} 0 1 089 -CF ₂ -CF ₃ N Cl -OCH _{(CH3) 2} 0 1 090 cf ₂ ci N SCH ₃ OCH ₃ with 1 091 CFgCl N CF ₃ OCH ₃ with 1 092 CFgCl Ň ch ₃ Cl s' ·. 1 093 CF ₂ C1 N OCH ₃ Cl with 1 094 cf ₂ ci TO ^C 2 ^H 5 CH ₃ with 1 095 cf ₂ ci N och ₃ -OCH _{(CH3) 2} with 1 096 CF ₂ C1 N -CH (CH _? > _? OCH ₃ with 1 097 CF ₂ Cl N CHgCl OCH ₃ with 1 098 CFgCl N CHgF OCH, with 1 099 CF ₂ C1 CH c ₂ h ₅ Cl with 1 100 cf ₂ ci CH CH, Cl with 1 101 CFgCl CH CH ₃ F with 1 102 CF ₂ C1 CH OCH ₃ Cl with 1 103 CFgCl N oc ₂ h ₅ oc ₂ h ₅ p. . 1 104 CF ₂ C1 N c ₂ h ₅ 0CH ₃ with 1 105 CFgCl N ch ₃ oca ₃ with 1 106 CF ₂ C1 N _ CH, OC ₂ ^H 5 with 1 107 CF ₂ C1 CH CH 3 CH ₃ with 1 108 CFgCl CH CH ₃ OCH, with 1 109 CFgCl CH och ₃ OCH,. 0 1 110 CF ₂ C1 N CH ₃ ch ₃ 0 11.1 CF ₂ C1 N och ₃ oc ₂ h ₅ 0 ', 1 112 CFgCl CH 0CH ₃ OC ₂ ^H 5 0 1 113 CF ₂ C1 CH -ch ₂ and ₃ 0CH ₃ 0 1 114 CF ₂ C1 N -ΟΗ ,, ΟΟΗγ 0CH ₃ 0 1 1,5 cf ₂ ci N OCH ₃ OCH ₃ 0 1 116 cf ₂ ci CH C ₂ H ₅ OCH ₃ 0 11.7 • CF ₂ C1 N -CHgOCH3 CH ₃ 0 1 1,8 chf ₂ CH -CHÍCH ^ ' och ₃ with 1 11-9 CHFg CH och ₃ ^SC 2 ^H 5 with 1 120 CHFg N och ₃ sc ₂ h ₅ with 1 121 CHF ₂ N och ₃ -SCH _(CH3)? with , 122 CHFg N CC1 ₃ CH, with 1, 23 CHFg N CH ₃ Br with

Table 7 - continued

Number AND E «3 ^R 4 X Physical data 1 124 chp ₃ N chf ₂ 0CH ₃ with 1 125 CHFg N chf ₂ CH, with 1 126 chf ₂ N -CH _? CF, Cl with 1 127 CHF ₂ N -CH _? -CF, 0CH ₃ with 1 128 chf ₂ N -CH _? -CF, CH, with 1 129 chf ₂ N -CH-OCH, ^CR 3 with 1 130 chf ₂ N -ch ₂ -sch CH ₃ with 1 131 chf ₂ N -CHp-SCH, sch ₃ with 1 132 CHF ₂ H -CH ₃ -SCH Cl with 1 133 chf ₂ N -ch ₂ -sch ₃ QC ^, with 1 134 chf ₂ N sch ₃ Cl with t 162 to 163 ° 1 135 chf ₂ N sch ₃ 0CH ₃ with T. 159 to 161 ° 1 136 chf ₂ N sch ₃ oc ₂ h ₅ 1 137 chf ₂ N sch ₃ -OCH (CH3) ij with 1 138 chf ₂ N -OCH (CH 2) _? whose with 147 to 149 ° 1 139 chf ₂ N CF, och ₃ with 1 140 chf ₂ N CF ₃ ch ₃ with 1 141 chf ₂ . N CF ₃ C ₂ H 5 with 1 142 chf ₂ N CC1 ₃ och ₃ with 1 143 chf ₂ H CC1 ₃ sch ₃ with 1 144 chf ₂ Η CH ₃ Cl with 1 145 chf ₂ N 0CH ₃ Cl with 151 to 153 ° 1 146 chf ₂ N OCH ₃ F with 1 147 chf ₂ N 0Cií ₃ Br with 1 148 chf ₂ N ch ₃ F with 1 149 chf ₂ N CH ₃ Br with 1 150 chf ₂ N ch ₃ H with 1 151 CHF ₂ CH c ₂ h ₅ Cl with 1 152 chf ₂ ch CH ₃ Cl with t 194 to 196 ° 1 153 chf ₂ CH ch ₃ sch ₃ with 1 154 chf ₂ CH, CH ₃ F with 186 to 187 ° 1 155 chf ₂ CH CHy Br with 1 156 chf ₂ CH c ₂ H ₅ cc ₂ h ₅ with 1 157 chf ₂ CH ^C 2 «5 sch ₃ with 1 158 chf ₂ ch ₂ CF ₃ ^CH 3 with 1 159 chf ₂ CH ch ₂ c'i ch ₃ with 1 160 chf ₂ CH ch ₂ ci och ₃ with 1 161 chf ₂ CH och ₃ Cl with T. 159 to 164 ° 1 162 chf ₂ CH Cl Cl with t 201 to 202 ° 1 163 chf ₂ CH 0CH ₃ SCH ₃ with 1 164 chf ₂ CH 0CH ₃ -0CH (CH3). ' with 1 165 chf ₂ CH CH ₂ F OCH, with 1 166 chf ₂ CH ch ₂ f ^CH 3 with 1 167 chf ₂ CH CF ₃ OCHy with 1 168 chf ₂ N c ₂ h ₅ -OCH _{(CH3) 2} with 1 169 chf ₂ N ^C 2 ^H 5 01 with T. 163 to 164 ° 1 170 chf ₂ N ^C 2 ^H 5 SCH ₃ with 1 171 chf ₂ H c ₂ h ₅ ch ₃ with T. 166 to 167 ° 1 172 chf ₂ N ®2 «5 C ^ with 1 173 chf ₂ N och ₃ -OCH (CH _T>? with 120 to 122 ° 1 174 chf ₂ H 0CH _{3 -0CH-CH3} with CH ₂ CH ₃

Table 7 - continued

Number AND E «3 «4 X physical data 1 175 chf ₂ N CH ₃ -CH (CH3) _? with 1 176 chf ₂ N -CHÍCH ^ Cl with T. 169 to 70 ° 1 177 chf ₂ N -CHtCH3 OCH ₃ with 148 to 150 ° 1 178 chf ₂ N -CH (CH 2) _? OC ₂ ^H 5 with 1 179 chf ₂ N -CH (CH-,) _? SCH ₃ with 1 180 chf ₂ N CHgCl CH ₃ with 1 181 chf ₂ N ch ₂ ci 0CH ₃ with 1 182 chf ₂ N ch ₂ f ch ₃ with 1 183 chf ₂ N ch ₂ f OCH ₃ with 1 184 chf ₂ N ch ₂ f och ₂ h with 1 185 chf ₂ N -CH _? -OCH _? ^C 2 ^H 5 with 1 186 chf ₂ N -ch ₂ -sch ₃ och ₃ with 1 187 chf ₂ CH -ch (ch,) ₂ OCH ₃ 0 t., 41 to 143 ° 1 188 CHFg CH och ₃ SCgHj 0 1 189 chf ₂ N och ₃ SC ^ Hj 0 1 190 chk ₂ N OCH ₃ -SCH _{(CH3) second} 0 1 191 chf ₂ N Cd ₃ CH ₃ 0 1 192 chf ₂ N ca ₃ Br 0 1 193 chf ₂ N CHF ₂ och ₃ 0 1 194 chf ₂ N chf ₂ ch ₃ 0 1 195 chf ₂ N -ch ₂ -cf ₃ Cl 0 1 196 chf ₂ H -ch ₂ -cf OCHy 0 1 197 chf ₂ N -CHp-CF3 ch ₃ 0 1 198 chf ₂ N -CHpOCH2 ch ₃ 0 1 199 chf ₂ N CH ₃ Br 0 1 200 chf ₂ N ch ₃ H 0 1 201 chf ₂ CH ^C 2 ^H 5 Cl 0 t., 58 to 159 ° 1 202 chf ₂ CH CH ₃ Cl 0 t., 90 to 191 ° 1 203 chf ₂ CH CH ₃ sch ₃ 0 t., 71 to 172 ° 1 204 chf ₂ CH CH ₃ F 0 t., 74 to 176 ° 1 205 CHF ₂ CH ch ₃ Br 0 1 206 CHF ₂ CH ^C 2 ^H 5 0C ₂ ^H 5 0 1 207 chf ₂ CH ^C 2 ^H 5 sch ₃ 0 1 208 chf ₂ ch ₂ CF ₃ CH- 0 1 209 chf ₂ CH CHgCl ^CH 3 0 1 210 chf ₂ CH CHgCl och ₃ 0 t., 67 to 168 ° 1 211 chf ₂ OH och ₃ Cl 0 T. 165 to 167 ° 1 212 chf ₂ CH Cl Cl 0 183 to 188 ° 1 213 chf ₂ CH och ₃ SCH ₃ 0 1 214 chf ₂ CH OCH ₃ -OCH _{(CH3) 2} 0 1 215 chf ₂ CH 0CH ₃ -0CH _{(CH3) 2} 0 T. 175 to 176 ° 1 216 chf ₂ CH ch ₂ f ch ₃ 0 1 217 chf ₂ CH CF ₃ OCH ₃ 0 1 218 chf ₂ N ^C 2 ^H 5 0CH _{(CH3) 2} 0 1 219 chf ₂ N ^C 2 ^H 5 Cl 0 135 to 37 ° 1 220 chf ₂ WITH ^C 2 ^H 5 SCH ₃ 0 1 221 chf ₂ N c ₂ h ₅ CH ₃  0 t 136 to 138 ° 1 222 chf ₂ N c ₂ «; ^C 2 ^H 5 0 1 223 chf ₂ N och ₃ -OCH (CH3) ₃ 0 t 113 to 115 ° 1 224 chf ₂ N och ₃ -OCH-CH 13 0

^CH 2 ^CH 3

Table 7 - continued

fiíelo AND E ^R 3 ^R 4 X Physical data 1 225 chf ₂ N ch ₃ -CH (CH _3)? 0 mp 137-140 ° , 226 chf ₂ N -ΟΗ (ΟΗ,) Cl . 0 m.p., 60-62 ° 1 227 CHř ₂ H -CHCCH3 0CH ₃ 0 1 228 CHF ₂ N -CH (CH-,) _? oc ₂ h ₅ 0 1 229 chf ₂ Η -CH (CH _3)? SCH ₃ 0 1 230 chf ₂ N ch ₂ ci ch ₃ 0 mp 1.3-1.15 ° 1,231 · chf ₂ N CHgCl och ₃ 0 mp 94-96 ° 1 232 chf ₂ N ch ₂ f CH ₃ 0 1 233 chf ₂ N ch ₂ f OCH ₃ 0 1 234 chf ₂ N ch ₂ f oc ₂ H ₅ 0 1 235 chf ₂ N ' -CH ₂ OCH ₃ ^C 2 ^H 5 0 1 236 chf ₂ N -ch ₂ sch ₃ OCH ₃ 0 1 237 chf ₂ N -CH _? SCH, CH ₃ 0 1 238 chf ₂ H -CHpSCH, sch ₃ 0 , 239 , chf ₂ N -CH _? SCH, Cl 0 1 240 chf ₂ N -ch ₂ sch ₃ oc ₂ h ₅ 0 1 24, chf ₂ N sch ₃ Cl 0 mp 147-149 ° 1 242 chf ₂ N sch ₃ . OCH ₃ 0 mp 161-162 ° 1 243 chf ₂ H sch ₃ oc ₂ h ₅ 0 1 244 chf ₂ N SCH ₃ 0CH (CH _3)? 0 mp 163-164 ° 1 245 chf ₂ N -con (ch,) ₂ Cl 0 mp, 03-104 ° 1 246 CHřg N CF ₃ OCH, 0 1 247 chf ₂ N cf ₃ CH ₃ 0 1 248 chf ₂ N cf ₃ oc ₂ ^h 5 0 1 249 chf ₂ N CC1 ₃ 0CH ₃ 0 1 250 chf ₂ N CC1 ₃ sch ₃ 0 1 251 chf ₂ N CH ₃ Cl 0 mp 160-161 ° 1 252 chf ₂ Η och ₃ Cl 0 mp, 67-168 ° 1 253 chf ₂ M OCH ₃ F 0 1 254 chf ₂ N och ₃ Br 0 1 255 chf ₂ N ch ₃ F 0 1 256 ch ₂ f N ch ₃ 0CH ₃ 0 1 257 ch ₂ f N och ₃ OCH ₃ 0 1 258 ch ₂ f N ch ₃ CH ₃ 0 1 259 ch ₂ f N ^C 2 ^H 5 OCH ₃ 0 1 260 ch ₂ f CH ch ₃ 0CH ₃ with 1 26, ch ₂ f CH OCH, OCH ₃ with 1 262 ch ₂ f CH CH ₃ gh ₃ with 1 263 ch ₂ f TO CH, och ₃ 0 1 264 ch ₂ f CH CH ₃ 0CH ₃ 0 1 265 ch ₂ f CH 0CH ₃ OCH ₃ 0 1 266 ch ₂ f N ^C 2 ^H 5 OCH ₃ 0 1 267 ch ₂ f N CH, ch ₃ 0 1 268 -CF ₂ -CF ₂ Br N ch ₃ 0CH ₃ 0 1 269 -CF ₂ -Cr ₂ Br CH CH ₃ 0CH ₃ 0 1 270 -CFg-CFgBr ca OCH ₃ OCH ₃ 0 1 271 -cf ₂ -cf ₂ ci N ch ₃ 0CH ₃ with 1 272 -ch ₂ -ch ₂ p N CH ₃ OCH, 0 1 273 -ch ₂ -ch ₂ f N ch ₃ ch ₃ 0 1 274 -ch ₂ -ch ₂ f N och ₃ OCH ₃ 0 1 275 -ch ₂ -ch ₂ f H c ₂ H ₅ OCH ₃ 0

Table 7 - continued

number Α E ^R 3 ^R 4 X Physical data 1 276 -ch ₂ -ch ₂ f CH ch ₃ 0CH ₃ 0 1 277 -CHg-CHgř CH OCH ₃ och ₃ 0 1 278 -CH ₂ -CH ₂ F CH ch ₃ ch ₃ 0 1 279 -ch ₂ -ch ₂ f N CH ₃ och ₃ with 1 280 -ch ₂ -ch ₂ f N OCH ₃ och ₃ with 1 281 -CH ₂ -CCl ₃ N CH ₃ och ₃ 0 1 282 -CH ₂ -CCl ₃ N OCH ₃ OCH ₃ 0 , 283 -CH ₂ -CCl ₃ CH CH ₃ OCH ₃ 0 1 284 -CH ₂ -CCl ₃ CH OCH ₃ OCH ₃ 0 1 285 -CH ₂ -CCl ₃ N c ₂ H ₅ och ₃ 0 1 286 -CF ₂ -CH ₃ N OCH, OCH ₃ 0 , 287 -CF ₂ -CH ₃ N ^CH 3 OCH ₃ 0 1 288 -CH ₂ -CH ₃ N CH, ch ₃ 0 1 289 -CF ₂ -CH ₃ CH ^CH 3 0CH ₃ 0 1 290 -CF ₂ -CH ₃ CH 0CH ₃ OCH ₃ 0 1 291 -ch ₂ -ch ₂ ci N CH ₃ OCH ₃ with 1 292 -ch ₂ -ch ₂ ci N och ₃ OCH ₃ with 1 293 -ch ₂ -ch ₂ ci N c ₂ h ₅ 0CH ₃ with 1 294 -ch ₂ -ch ₂ ci H ch ₃ oc ₂ h ₅ with 1 295 _{-CH2 -CH2} C1 CH c ₂ h ₅ OCH ₃ with 1 296 _{-CH2 -CH2} C1 N CH ₃ oc ₂ h ₅ 0 1 297 _{-CH2 -CH2} C1 N ch ₃ oc ₂ h ₅ with 1 298 -ch ₂ -ch ₂ ci CH OCH ₃ OCH ₃ with , 299 _{-CH2 -CH2} C1 CH ch. OCH ₃ with 1 300 _{-CH2 -CH2} C1 N cf ₃ 0CH ₃ 0 1 301 _{-CH2 -CH2} C1 N ch ₂ f OCH, 0 1 302 -ch ₂ -ch ₂ ci CH CHjCH ,, Cl 0 1 303 -ch ₂ -ch ₂ ci CH och ₃ Cl 0 1 304 _{-CH2 -CH2} C1 CH -CH 2 OCH 3 0CH ₃ 0 1 305 -ch ₂ -ch ₂ ci N -CHpOCH2 OCH ₃ 0 1 306 -ch ₂ -ch ₂ ci N 0CH ₃ 0CH ₃ 0 174-175 1 307 _{-CH2 -CH2} C1 N och ₃ OCH, 0 1 308 -ch ₂ -ch ₂ ci N ch ₃ CH ₃ 0 1 309 _{-CH2 -CH2} C1 N ^C 2 ^H 5 OCH ₃ 0 1 310 _{-CH2 -CH2} C1 N c ₂ H ₅ CH, 0 1 311 _{-CH2 -CH2} C1 N CH ₃ ⁰¹ 0 Ί 312 _{-CH2 -CH2} C1 N CH ₂ C1 OCH ₃ 0 1 313 -ch ₂ -ch ₂ ci N OCH ₃ -OCH (CH 2) _? 0 1 314 _{-CH2 -CH2} C1 N OCH ₃ SCH ₃ 0 1 315 _{-CH2 -CH2} C1 N -ch (ch,) ₂ 0CH ₃ 0 1 316 _{-CH2 -CH2} C1. N 0¾ OCH ₃ 0 , 317 _{-CH2 -CH2} C1 N oc ₂ h ₅ oc ₂ h ₅ 0 1 318 _{-CH2 -CH2} C1 N 0CH ₃ Cl 0 1 319 _{-CH2 -CH2} C1 CH CH ₃ OCH ₃ 0 208-209 1 320 _{-CH2 -CH2} C1 CH 0CH ₃ 0CH ₃ 0 1 321 -ch ₂ -ch ₂ ci CH ch ₃ CH, 0 181-183 ° 1 322 -ch ₂ -ch ₂ ci CH CH ₃ Cl 0 1 323 -ch ₂ -ch ₂ ci CH ch ₃ F 0 1 324 -ch ₂ -ch ₂ ci CH c ₂ h ₅ OCH ₃ 0 1 325 -OCHg-CHCl-CHgCl N CH ₃ OCH ₃ 0 1 326 -OCH ₂ -CaCl-CH ₂ Cl N och ₃ OCH ₃ 0

Table 7 - continued

Number AND £ ®3 X— Fjřzikélní data 1 327 -OCH ₂ -CHCl-CH ₂ Cl N ch ₃ ^CH 3 0 1 328 -OCH ₂ -CHCl-CH ₂ Cl H ^C A 0CH ₃ 0 1 329 -OCH ₂ -CHCl-CH ₂ Cl CH CH ₃ 0CH ₃ 0 1 330 -OCH ₂ -CHCl-CH ₂ Cl CH och ₃ OCH ₃ 0 1 331 -OCH ₂ -CHCl-CH ₂ Cl CH CH ₃ CH ₃ 0 1 332 -OCH ₂ -CHCl-CH ₂ Cl M ch ₃ 0CH ₃ with 1 333 -OCH ₂ -CHCl-CH ₂ Cl N OCH ₃ 0CH ₃ with 1 334 -OCH ₂ -CHCl-CH ₂ Cl CH CH ₃ 0CH ₃ with 1 335 -OCH ₂ -CHCl-CH ₂ Cl CH OCH ₃ 0CH ₃ with 1 336 -OCH ₂ -CHCl-CH ₂ Cl N c ₂ h ₅ CH, 0 1 337 -OCH ₂ -CHCl-CH ₂ Cl N OCHj Cl 0 1 338 -OCH ₂ -CHCl-CH ₂ Cl CH CH ₃ Cl 0 1 339 ch ₂ f N CH ₃ 0¾ 0 1 340 ch ₂ f CH CH ₃ Cl 0 1 341 ch ₂ f M OCH ₃ Cl 0 1 342 -CH ₂ -CHCl-CH ₂ Cl CH ^C 2 ^H 5 Cl 0 1 343 -CH ₂ -CHBr-CH ₂ Br N CH ₃ OCH ₃ 0 1 344 -ch ₂ -chci-chci N CH ₃ och ₃ 0 ch ₃ 1 345 -CH ₀ -CHCl-CHCl 2 i N 0CH ₃ 0CH ₃ 0 1 ca ₃ 1 346 -CH ₀ -CHCl-CHCl 2 i N CH ₃ CH ₃ 0 CH ₃ 1 347 -CH2CHCl-CHCl 2 i CH ch ₃ och ₃ 0 CH ₃ 1 348 -CH 2 -CHCl -CHCl CH CH ₃ Cl 0 | CH ₃ 1 349 -CH ₀ -CHCl-CHCl 2 i CH OCH ₃ 0CH ₃ 0 CH ₃ 1 350 -CH _O -CHCl-CHCl * I N ^C 2 ^H 5 0CH ₃ 0 CH ₃ 1 351 -CF ₂ -CHF ₂ N ^C 2 ^H 5 OCH, 0 t. 158 to 160 ° 1 352 -cf ₂ -chf ₂ CH ch ₃ Cl ^J 0 1 353 -cf ₂ -chf ₂ CH OCH ₃ Cl 0 T. 164 to 165 ° 1 354 -cf ₂ -chfci N c ₂ h ₅ OCH, 0 144 to 146 ° 1 355 -cp ₂ -chfci CH CH ₃ Cl 0 T. 177 to 179 ° 1 356 -cf ₂ -chpci CH 0CH ₃ Cl 0 T. 164 to 165 ° 1 357 -cf ₂ -chfci N -CH (CH _{3) 2} OCH ₃ 0 t 128 to 130 °

Table 8

Νγ’ΐ

X-A

Number AND Position X-A ^R ! Λ ^R 4 X E 1 401 chf ₂ 2 5-F ^C 2 ^H 5 och ₃ 0 if 1 402 chf ₂ 2 5-F ch ₃ Cl 0 CH 1 403 chf ₂ 2 5-F 0CH ₃ SCH ₃ 0 N 1 404 chf ₂ 2 5-F OCH ₃ -OCH (CH 2) _? 0 N 1 405 chf ₂ 2 5-F OCH ₃ Cl 0 N 1 406 chf ₂ 2 5-F ° 2 ^H 6 OCH, with Ν ' 1 407 chf ₂ 2 5-F CH ₃ Cl with N 1 408 chf ₂ 2 5-F ch ₃ Cl with CH 1 409 chf ₂ 2 5-F ^C 2 ^H 5 ch ₃ 0 N 1 410 chf ₂ 2 5-F ^C 2 ^H 5 ch ₃ 0 CH 1 411 CHFg 2 5-F och ₃ Cl 0 CH 1 412 chf ₂ 2 5-F oc-A Cl 0 N 1 413 chf ₂ 2 5-F CH ₃ F 0 N 1 414 chf ₂ 2 5-F ch ₃ Br 0 N 1 415 chf ₂ 2 5-F ch ₃ Br 0 CH 1 416 chf ₂ 2 5-F CH ₃ F 0 CH 1 417 chf ₂ 2 5-F ^C 2 ^H 5 Cl 0 CH 1 418 chf ₂ 2 5-F ch ₂ f OCH ₃ 0 N 1 419 Cgik 2 5-F CH, OCH ₃ 0 N 1 420 ^C 2 ^F 5 2 5-F ch ₃ och ₃ 0 N 1 421 ^c 2 ^f 5 2 5-F ch ₃ och ₃ 0 CH 1 422 c ₂ f; 2 5-F och ₃ och. 0 CH 1 423 ^C 2 ^F 5 2 5-F ch ₃ Cl 0 CH 1 424 ^C 2 ^F 5 2 6-F ch ₃ OCH ₃ 0 , tt 1 425 ^C 2 ^F 5 2 6-F ch ₃ OCH ₃ 0 ’CH 1 426 C ₂ ^f 2 6-F ^C 2 ^H 5 OCH ₃ 0 N 1 427 c ₂ h 2 6-F CH ₃ BCH ₃ with N 1 428 c ₂ f ₅ ⁵ 2 6-F ch ₃ och ₃ with CH 1 429 CA 2 6-F ° 2 ^H 6 och ₃ with N 1 430 ^C 2 ^F 5 2 6-COOCH ₃ CH ₃ OCH, 0 N 1 431 c ₂ ^p 2 6-COOCH ₃ 0CH ₃ 0ch ₃ 0 N 1 432 ° ^F 5 2 6-COOCH CH ₃ OCH ₃ 0 CH 1 433 ^C 2 ^F 5 2 6-F c ₂ h ₅ OCH ₃ 0 N 1 434 chf ₂ 2 6-F c ₂ h ₅ och ₃ 0 N 1 435 chf ₂ 2 6-F CH ₃ Cl 0 CH 1 436 chf ₂ 2 6-F CH. Br 0 CH 1 437 chf ₂ 2 6-F 0ÉH ₃ -ΟΟΗ (ΟΗ _ί ) ₂ 0 N 1 438 chf ₂ 2 6-F 0CH ₃ Cl 0 N 1 439 chk ₂ 2 6-F -ch (ch,) ₂ OCH ₃ 0 N 1 440 chf ₂ 2 6-F e ₂ ^H 5 OCH, 0 CH 1 441 chf ₂ 2 6-F ^C 2 ^H 5 Cl 0 CH 1 442 chf ₂ 2 6-F CH ₃ SCH ₃ 0 N 1 443 chf ₂ 2 6-5 0CH ₃ SCH, 0 N 1 444 chf ₂ 2 6-F -OCH (CH 2) _? Cl 0 N 1 445 chf ₂ 2 6-F ^C 2 ^H 5 CH ₃ 0 N 1 446 chf ₂ 2 6-F -CH (CH _{3) 2} CH ₃ 0 N

Physical data

mp 140-141 °

mp 160-161 °

Table 8 - continued number A Position R, R ^

X-A

X E Physical data

1 447 CHF ₂ 2 6-F ch ₂ f och ₃ O N 1 448 chf ₂ 4 6-F c ₂ h ₅ OCH, with N 1 449 chf ₂ 2 6-F CH ₃ Cl with CH 1 45a CHF ₂ 2 6-F ch ₃ Br with CH 1 451 chf ₂ 2 6-F och ₃ Cl with CH 1 452 chf ₂ 2 6-F ^C 2 ^H 5 CH ₃ with CH 1 453 chf ₂ 2 5-F och ₃ OCH ₃ 0 N t. t 150 to 151 ° 1 454 chf ₂ 2 6-C1 och ₃ 0CH ₃ 0 N t 162 to , 65 ° 1 455 chf ₂ 2 6-C1 och ₃ 0CH ₃ 0 CH t., 48 to 154 ° 1 456 chf ₂ 2 6-C1 CH ₃ CH ₃ 0 CH t 189 to , 91 ° 1 457 CHF 2 2 5-C1 °° ^Η 3 OCH ₃ 0 N t., 64 to 166 ° 1 458 chf ₂ 4 _2-CH3 ch ₃ 0CH ₃ 0 N 147 to 150 ° 1 459 chf ₂ 2 5-C1 ^C 2 ^H 5 OCH ₃ 0 N 130 to , 32 ° 1 460 chf ₂ 2 5-C1 -CH (CH _{3) 2} 0CH ₃ 0 N t 149 to 151 ° 1 46, chf ₂ 2 5-C1 ch ₃ Cl 0 CH t. 182 (decomposition) 1 462 chf ₂ 2 5-C1 och ₃ Cl 0 CH t. 170 to 172 ° 1 463 chf ₂ 2 5-C1 -och (ch,) ₂ ^0Cií 3 0 N t., 28 to , 35 ° 1 464 chf ₂ 2 5-C1 och ₃ SCH ₃ 0 CH

Table 9

SO 4 -NH-C-NH-T> ^N Y ^{CH 3} 1 | Ν £ γΕ

A-A

004 $

Number AND AND Position X-A R, r ₂ X E 1 501 chf ₂ 3 6-NOg 3-Br with N 1 502 CF ₃ 3 6-COOC ₂ H ₅ 3-Br 0 N 1 503 CF, 3 6-COOC ₂ H ₅ 3-Br with N 1 504 CP ₃ 3 _6-CH3 2-C1 SO ₂ CH 1 505 chf ₂ 3 _6-CH3 2-C1 S0 ₂ CH 1 506 chf ₂ 3 2-NO ₂ 2-C1 0 N 1 507 chf ₂ 3 2-NO ₂ 2-C1 0 CH 1 508 chf ₂ 3 2-COOC ₂ H ₅ 2-C1 0 H 1 509 chf ₂ 3 2-C00C ₂ H ₅ 2-C1 with N 1 510 chf ₂ 3 6-C1 2-C1 0 CH 1 511 chf ₂ 3 6-C1 2-C1 with CH 1 512 chf ₂ 3 6-C1 2-C1 Sat N 1 513 chf ₂ 3 6-C1 2-C1 SO ₂ N 1 514 chf ₂ 3 2-CF ₃ 2-C1 0 N 1 515 chf ₂ 3 5-NO ₂ 2-C1 0 N 1 516 chf ₂ 3 6-0CH ₃ 2-C1  Ό CH 1 517 chf ₂ 3 6-OCH ₃ 2-C1 0 N 1 518 chf ₂ 3 6-SCH ₃ 2-C1 0 CH 1 519 chf ₂ 3 6-SCH ₃ 2-C1 0 N

Physical data

mp 170-172 °

Table 9 - continued

Number A Position X-A ^R 1 ^R 2 X E Physical data 1,520 CHF ₂ 3 2-SO _? CH 2 2-C1 0 CH 1,521 CHF ₂ 3 2-SO ₂ CH ₃ 2-C1 0 N Table 10 φ-50 _£ ΝΗ- O C-NH- (-) * 4

number AND X m Positions X-A E «3 ^R 4 Physical data 1 601 chf ₂ 0 2 2.5 N ch ₃ 0CH ₃ mp 1.3 ° 1 602 chf ₂ with 2 2.5 N ch ₃ 0CH ₃ 1 603 chf ₂ 0 2 2.6 N ch ₃ 0CH ₃ 1 604 chf ₂ 0 2 2.5 CH ch ₃ 0CH ₃ 1 605 chf ₂ 0 2 2.5 CH Cl CH ₃ 1 606 chf ₂ 0 2 2.5 CH Cl och ₃ 1 607 chf ₂ 0 2 2.5 N c ₂ h ₅ och ₃ 1 608 chf ₂ 0 2 2.5 N 0CH ₃ OCH ₃ 1 609 tFCF, -CF ₉ H 0 2 2.5 N CH ₃ OCH ₃ 1 610 -CF ₂ -CF ₂ H 0 2 2.5 N ch ₃ OCH ₃ 1 61, cf ₃ 0 2 2.5 N ch ₃ OCH ₃

WITH

II

Table 11

CC

SO 2 NH-C-NH

Νγε

number AND E ^R 3 ^R 4 X 1 701 chf ₂ N c ₂ H ₅ 0CH ₃ 0 1 702 chf ₂ CH ^C 2 ^H 5 0CH ₃ 0 1 703 chf ₂ N OCH ₃ -0CH _{(CH3) 2} 0 1 704 chf ₂ N -ch (ch,) ₂ OCH ₃ 0 1 705 chf ₂ N ^C 2 ^H 5 OCH ₃ with 1 706 chf ₂ CH c ₂ h ₅ OCH ₃ with 1 707 chf ₂ N ^C 2 ^H 5 -0CH (CH3) _? with 1 708 chf ₂ N -ch (ch,) ₂ OCH ₃ with 1 709 c ₂ f ₅ N ch ₃ 0CH ₃ 0 1 710 ^C 2 ^P 5 N ch ₃ OCH ₃ with 1 711 CF ₂ CHF ₂ N ^C 2 «5 0CH ₃ 0 , 7.2 cf ₂ chf ₂ N -OCH _{(CH3) 2} och ₃ 0

Table 12

V ^with OrNH-C-NH-R 1 -A

N ~ \

Number AND E ^R 3 ^R 4 X of Physical data 1 801 CHK ₂ N ch ₃ OCH ₃ O 0 mp 132-134 ° 1 802 chf ₂ N ch ₃ oc ₂ h ₅ 0 0 mp 121-122 ° 1 803 chf ₂ CH CH ₃ CH ₃ O 0 mp 199-201 ° 1 804 chf ₂ CH ch ₃ OCH ₃ 0 0 mp 189-191 ° 1 805 chf ₂ CH och ₃ OCH ₃ 0 0 mp 152-154 ° 1 806 chf ₂ N CH ₃ OCH ₃ 0 with mp 148-150 ° 1 807 chf ₂ N CH ₃ CH ₃ with 0 1 808 chf ₂ N CH ₃ OCH ₃ with 0 mp 169-172 ° 1 809 chf ₂ N CH ₃ OCgHj with 0 mp 154-155 ° 1 810 chf ₂ N CH ₃ OCH ₃ with with 1 811 chf ₂ CH ch ₃ CH ₃ with 0 mp 176-178 ° 1 812 chf ₂ CH ch ₃ OCH ₃ with 0 mp 172-174 ° 1 813 chf ₂ CH 0CH ₃ OCH ₃ with 0 mp 155-162 ° 1 814 CaF ₂ N ch ₃ CH ₃ 0 0 1 815 CF, N ch ₃ 0CH ₃ Sat 0 1 816 CF ₃ CH CH, OCH ₃ Sat 0 1 817 CF ₃ N CH ₃ 0CH ₃ Sat ₂ 0 1 818 CF ₃ CH CH ₃ OCH ₃ SO ₂ 0 1 819 chf ₂ N CH ₃ OCH ₃ Sat 0 mp 165-167 ° 1 820 CHF, ti N ch ₃ CH ₃ Sat 0 1 821 CHF ₂ N ch ₃ OC 2 ^ 5 Sat 0 mp 156-158 ° 1 822 chf ₂ CH Honors ₃ CH ₃ Sat 0 1 823 chf ₂ CH CH ₃ och ₃ Sat 0 mp 195-197 ° 1 324. chf ₂ CH OCH ₃ och ₃ Sat 0 1 825 chf ₂ N CH ₃ OCH ₃ Sat with 1 826 chf ₂ N CH ₃ ch ₃ Sat ₂ 0 1 827 chf ₂ N ch ₃ och ₃ SO ₂ 0 1 828 chf ₂ N CH, 0¾ SO ₂ 0 1 829 chf ₂ N CH ₃ OCH ₃ SO ₂ with 1 830 chf ₂ CH CH ₃ OCH ₃ SO ₂ 0 1 831 chf ₂ CH ch ₃ OCH ₃ SO ₂ 0 1 832 chf ₂ CH OCH ₃ OCH ₃ SO ₂ 0 1 833 cf ₃ M CH ₃ OCH, O 0 mp 160-162 ° 1 834 cf ₃ N CH ₃ CH ₃ 0 0 1 835 CF ₃ N CH ₃ OCpHg 0 0 1 836 cf ₃ CH CH ₃ CH ₃ 0 0 1 837 cf ₃ CH CH ₃ OCH ₃ 0 0 mp, 48-152 ° 1 838 cf ₃ CH och ₃ och ₃ 0 0 1 839 CF ₃ N CH ₃ OCH ₃ 0 with 1 840 cf ₃ N CH ₃ CH ₃ WITH 0 1 841 cf ₃ N ch ₃ och ₃ with 0 1 842 CF ₃ N CH ₃ OCgHj with 0 1 843 CF ₃ N ch ₃ 0CH ₃ with with 1 844 cf ₃ CH ch ₃ CH ₃ with 0 1 845 cf ₃ CH ch ₃ och ₃ with 0 1 846 CF ₃ CH OCH ₃ OCH ₃ with 0 1 847 -CF ₂ -CHF ₂ N CH ₃ OCH ₃ 0 0 mp 170-174 °

Table 12 - continued

Number AND E ^K 3 ^R 4 X of Fyziki ílní 1 848 -CF ₂ -CHF ₂ N ch ₃ ch ₃ 0 0 1 849 -cf ₂ -chf ₂ N ch ₃ OCA 0 0 s. 136 1 850 -cf ₂ -chf ₂ CH ch ₂ CH ₃ 0 0 1 851 -cf ₂ -chf ₂ CH ch ₃ OCH ₃ 0 0 t. t. 178 1 852 -cf ₂ -chf ₂ CH och ₃ 0CH ₃ 0 0 1 853 -cf ₂ -chf ₂ N ch ₃ 0CH ₃ 0 with 1 854 -CFp-CHF N ch ₃ CH ₃ with 0 1 855 -CF ₂ -CHF ₂ N CH, OCH ₃ with 0 t. t. 156 1 856 -cf ₂ -chf ₂ N CH ₃ oc ₂ h ₅ with 0 1 857 -cf ₂ -chf ₂ N CH ₃ OCH ₃ with with 1 858 -cf ₂ -chf ₂ CH CH ₃ CH ₃ with 0 1 859 -cf ₂ -chf ₂ CH CH ₃ och ₃ with 0 1 860 -CF ₂ -CHF ₂ CH OCH ₃ 0CH ₃ with 0 1 861 -cf ₂ -chcif N CH, 0CH ₃ 0 0 t. t. 148 1 862 -cf ₂ -chcif N CH ₃ CH ₃ 0 0 1 863 -cf ₂ -chcif H CH ₃ OC-jH 0 0 1 864 -CF ₂ -CHClF CH CH ₃ CH ₃ 0 0 t. t. 178 1 865 -cf ₂ -chcif CH CH ₃ 0CH ₃ 0 0 1 866 -cf ₂ -chcif CH OCH ₃ 0CH ₃ 0 0 1 867 -cf ₂ -chcif N ch ₃ och ₃ 0 with 1 868 -cf ₂ -chcif N ch ₃ ch ₃ with 0 1 869 -cf ₂ -chcif N CH ₃ 0CH ₃ with 0 1 870 -cf ₂ -chcif N ch ₃ 0¾ with 0 1 871 -cf ₂ -chcif N CH ₃ OCH ₃ with with 1 872 -cf ₂ -chcif CH ch ₃ CH ₃ with 0 1 873 -cf ₂ -chcif CH ch ₃ OCH ₃ with 0 1 874 -cf ₂ -chcif CH och ₃ 0CH ₃ with 0 1 875 -CF ₂ -CHBrF N ch ₃ OCH, 0 0 1 876 -CFg-CHBrF N CH ₃ ^OBJECTIVE 3 0 0 1 877 -CFg-CHBrF M CH ₃ 0¾ 0 0 1 878 -CFg-CHBrF CH CH ₃ ^CH 3 0 0 1 879 -CF ₂ -CHBrF CH ch ₃ och ₃ 0 0 1 880 -CF ₂ -CHBrF CH 0CH ₃ OCH ₃ 0 0 1 881 -CFg-CHBrF M CH ₃ 0CH ₃ 0 with 1 882 -CFg-CHBrF N CH ₃ CH ₃ with 0 1 883 -CFg-CHBrF N CH, OCH ₃ with 0 1 884 -CF ₂ -CHBrF N ^CH 3 0¾ with 0 1 885 -CFg-CHBrF N CH ₃ OCH ₃ with with 1 886 -CFg-CHBrF CH CH ₃ CH ₃ with 0 1 887 -CF ₂ -CHBrF CH CH ₃ OCH ₃ with 0 1 888 -CF ₂ -CHBrF CH 0CH ₃ och ₃ with 0 1 889 CHF ₂ N 0CH ₃ 0CH ₃ 0 0 t. t. 135 1 890 chf ₂ N OCH ₃ OCH ₃ with 0 t. t. 145 1 891 chf ₂ N OCH ₃ OCHj S0 ₂ 0 1 892 chf ₂ N 0CH ₃ 0CH ₃ SO ₂ 0 1 893 CF ₃ N 0CH ₃ och ₃ 0 0 t. t. 174 ' 1 894 cf ₃ N och ₃ och ₃ with 0 1 895 -cf ₂ -chf ₂ N OCH ₃ OCHý 0 0 t. t. 179 1 896 -CF ₂ -CHF ₂ N 0CH ₃ OCH ₃ with 0 1 897 -cf ₂ ccif ₂ N . OCH ₃ OCH ₃ 0 0 1 898 chf ₂ N och ₃ oc ₂ H ₅ 0 0 t. t. 114

Table 12 - continued

Number AND E * 3 ^R 4 X of Physical data 1 899 chf ₂ N ch ₃ 0CH ₃ 0 0 mp, 32-134 ° 1 900 chf ₂ N och ₃ och ₃ 0 0 mp, 35-137 ° 1 901 CHF ₂ N ch ₃ och ₃ with 0 mp, 69-172 °

Table ^R i

OCH,

number AND E Rg ^R , X Physical data 2 00, CHFg N CH, H 0 2 002 CHF N Cl H 0 2 003 CF, N Cl H 0 2 004 CHFg N H H 0 mp 153-154 ° 2 005 CHFg CH H H 0 2 006 CHFg N F H 0 2 007 CHFg CH F H 0

Table 14

No. AND E ^R , r ₂ X Physical data 2 10, CHFg N H Cl 0 mp, 54-157 ° 2 102 CHFg CH H Cl 0 mp 168-70 ° 2 103 CHFg CH H Cl with 2, 04 CHFg N H Cl with 2 105 -CFg-CHCIF N Cl H 0 2 106 cf ₃ N Cl H 0 2 107 \ CHFg N Cl H with 2, 08 CHFg N H F 0 2 109 chf ₂ CH H F 0 2 110 chf ₂ N F H 0 mp 1.6-118 ° 2, 11 chf ₂ CH F H 0 mp 152-154 ° 2 112 chf ₂ CH Cl H 0 2, 13 chf ₂ N Cl H 0 mp 139-143 ° 2 114 chf ₂ CH ch ₃ H 0 2 1,5 CHFg N CH, H 0 2, 46 CHFg CH Br H 0 2 117 chf ₂ N Br H 0

Examples illustrating the composition and preparation of formulations:

Example 13

Examples of compositions for liquid active substances of formula I (% =% by weight)

Emulsion concentrates and) (b) C) active substance 20% 10% 50 calcium dodecylbenzenesulfonic acid acid 5% 4% 5 castor oil polyethylene glycol ether 5% 4% (36 moles of ethylene oxide) cyclohexanone 30% 20% mixture of xylenes 40% 62 93

Emulsions of any desired concentration of active ingredient can be prepared from such concentrates by dilution with water.

(b) Solutions and) (b) C) (d) active substance 20% 10% 5% 1% ethylene glycol monoethyl ether 30% - 50% 50% polyethylene glycol molecular weight 400 - 70% - 20% H-methyl-2-pyrrolidone 50% 20% 44% 28% epoxidized coconut oil - - 1% 1% Such solutions are suitable for: use in in the form of small drops • E) Granules and) (b) active substance 5% 10% kaolin 94% . - highly dispersed silicic acid 1% attapulgit - 90% The active substance is dissolved in methylene chloride and sprayed on the carrier and the solvent are added tom Evaporate in vacuo. (d) Dust and) (b) active substance 0.1% 1%

high-grade silicic acid 1% 5% aastek 98,9% kaolin - 94%

By thoroughly mixing the carrier substances with the active ingredient, a directly usable dust is obtained

Example

Examples of compositions for solid active substances of formula I (% =% by weight)

a) Wettable powder a) b) c) Active substance hatriualignin sulphonate% 60% 0,5%% 5% 5%

sodium lauryl sulfate 3 56 - - sodium diisobutylnaphthalenesulfonate - 6 % 6% octylphenolpolyethylene glycol ether (7 to 8 moles of ethylene oxide) - 2 % 2 56 highly dispersed silicic acid 5% 27 Mar: % 27% kaolin 67 56 - - sodium chloride - - 59.5% The active ingredient is well mixed with the ingredients and mix well ground in suitable mill. Gets is a wettable powder which is diluted with water to suspension of each desired concentration.

b) Emulsion concentrate a) b) effective flux 10% 1 56 octylphenolpolyethylene glycol ether (4 to 5 moles of ethylene oxide) 3% 3% dodecylbenzenesulphonic acid calcium salt 3% 3 56 Castor oil polyglycol ether (36 moles of ethylene oxide) 4 56 4 56 cyclohexanone 30% 10 Mixture of xylenes 50%

Emulsions of any desired concentration can be prepared from this concentrate by dilution with water.

c) Dusting

and)

(b) the active substance talc kaolin

0.1% 1,556 99.9 56

56

Directly usable dust is obtained by mixing the active ingredient with a carrier and grinding the mixture in a suitable mill.

(d) Extruded granules (a) (b) Active ingredient 10% 1 56 Sodium lignin sulphonate 2 56 2 56 Carboxymethylcellulose 1 56 .1 56 Kaolin 87 56 96%

The active ingredient is mixed with the ingredients, ground and moistened with water. This mixture is extruded on an extruder and then the granulate is dried in an air stream.

e) Coated granulate active substance polyethylene glycol (molecular weight 200) kaolin

56

The finely divided active ingredient is applied evenly to the kaolin moistened with polyethylene glycol in a stirrer. In this way a dust-free coated granulate is obtained.

f) Suspension concentrate a) b)

Active ingredient ethylene glycol 10% nonylphenolpolyethylene glycol ether (15 moles ethylene oxide) 6% sodium lignin sulphonate 10% carboxymethylcellulose 1% yj% aqueous formaldehyde solution 0.2% silicone oil in the form of a 75% aqueous emulsion 0.8% water 32%%

%%

% 0.2% 0.8% n%

The finely divided active ingredient is intimately mixed with the ingredients. This gives a suspension concentrate from which suspensions of any desired concentration can be prepared by dilution with water.

g) Salt solution active substance 5% isopropylamine 1% octylphenolpolyethylene glycol ether (78 mol ethylene oxide) 3% water 91%

Examples illustrating biological activity:

Example 15

Evidence of herbicidal activity before emergence of plants

Plant seeds are planted in pots with a diameter of 12 to 15 cm in a greenhouse. Immediately thereafter, the soil surfaces are treated with an aqueous dispersion or solution of active ingredients. A concentration of 4 kg of active substances per ha is used. The pots are then kept in a greenhouse at 22-25 ° C and 50-70% relative humidity. After 3 weeks, the experiment is evaluated and the effect is assessed according to the following scale:

plants do not germinate or are completely dead up to 3 very strong effect up to 6 medium effect up to 8 slight effect no effect (as in the case of untreated control plants)

Compounds of formula A were used at the same concentration as the comparator in this experiment

OCH3-J2-SO2NH-CO-NH

Cl

OCH, (A) known from Example 2 of European Patent Application No. 1485.

Preemergence effect:

application rate of 4 kg of effective flight / ha

Compound C. Avena Setaria Sinapis Stellaria 1 4 4 2 2 2 4 4 2 2 ' 75 5 6 2 2 76 4 4 2 2 77 5 6 2 2 81 3 1 2 2 83 6 6 2 2 90 2 2 2 2 91 2 2 2 2 ' 102 6 7 2 2 131 2 3 2 2 132 2 3 2 2 195 6 4 2 2 196 4 3 2 2 200 6 5 2 2 301 6 7 2 2 302 5 4 2 2 303 5 6 2 2 312 6 5 2 2 316 4 2 2 2 329 3 2 2 2 331 4 4 2 2 333 6 5 2 2 337 2 2 2 2 470 2. 2 2 2 471 1 1 2 2 497 4 1 2 2 500 6 3 2 2 522 4 2 2 2 524 3 4 2 2 526 3 2 2 2 527 2 2 2 2 528 3 2 2 2 532 5 5 2 3 541 6 3 2 2 551 2 3 2 2 557 8 6 2 2 587 4 3 2 2 595 2 2 1 2

Preemergence effect:

application rate: 4 kg of active substance / ha

Compound C. Avena Setaria Sinapis Stellaria 901 2 1 2 1 902 6 4 2 2 919 2 1 2 1 1 161 6 3 2 2 1 202 4 1 2 2 1 203 3 1 2 2 1 212 7 3 2 2 1 223 3 2 2 2 1 242 5 4 2 2 1 244 4 2 2 2 1 245 3 1 2 2 1 252 4 2 2 2 1 453 2 1 2 2 1 454 2 1 2 2 1 455 4 1 2 1 1 456 2 1 2 2 1 457 3 2 2 2 1 601 2 1 2 1 1 806 6 3 2 2 ' 1 809 5 2 2 1 1 812. 2 1 2 2 1 813 3 1 2 1 1 823 3 2 2 2 1 861 6 3 2 2 1 890 5 3 2 1 1 893 3 2 2 2 1 898 3 2 2 2 2 004 2 1 2 2 2 101 2 1 2 2 2 102 2 1 2 1 2 110 2 1 2 2; 2 111 2 1 2 2 2 113 2 1 2 2 comparative substance A 9 6 3 6 ^J Test ns and the herbicidal action of the preemergent application compounds of formula I

markedly stronger effect on test plants than comparative compound A.

Example 16

Evidence of selectivity in pre-emergence treatment

In the same experimental set-up as in Example 15, a plurality of plant seeds were treated with different amounts of active ingredient. The evaluation is carried out on the same scale.

Test results (pre-emergence treatment):

í5ij sil ¢ -. and

Effect Amount used kg active ingredient / ha test plant 0.25 Compound No. 60, Compound No. 913 0.12 O, 06 / 0.03 0.25 0.12 0.06 0.03 wheat 4 7 9 9 5 6 7 9 maize 2 2 2 2 3 3 7 8 Avena fatua 2 2 3 4 5 6 6 8 Alopecurus myosuroides 2 2 2 2 2 2 2 3 Echinochloa crus galii 2 2 2 2 2 2 3 3 ' Rottboellia exaltata 2 3 3 3 3 3 4 4 Cyperus esculentus 3 3 3 3 2 3 3 5 soya 2 2 2 2 2 2 3 3 cotton 2 2 2 3 1 2 2 2 ebutilon 1 1 2 2 1 1 1 1 Beetle (Xanthium sp.) 2 3 3 3 2 2 2 3 Chenopodium sp. 1 1 2 2 2 2 2 2. Ipomoea 2 2 2 2 2 2 2 2 Sinapis 2 2 2 2 1 1 1 1 Galium aparine 2 2 2 3 2 2 3 , 3 Viola tricolor 2 2 2 2 '1 1 1 1

Effect Compound No. 924 Compound No. 16, Quantity used kg active ingredient / ha 0.25 0.12 0.06 0.03 0.25 0.12 0.06 0.03 Tested plant wheat 9 9 9 9 7 8 9 9 maize 9 9 9 9 9 9 9 9 Avena fatua 9 9 9 9 7 8 8 9 Alopecurus myosuroides 4 9 9 9 4 4 5 7 Echinochloa crus galii 6 6 9 9 2 3 3 3 Rottboellia exaltata 7 9 9 9 4 4 7 7 Cyperus esculentus 3 4 9 9 1 2 3 3 soya 4 4 8 9 6 9 9 9 cotton 2 2 6 6 4 4 4 9 ebutilon 1 1 2 2 1 2 4 4 Beetle (Xanthium sp.) 2 2 9 9 4 6 6 8 Chenopodium sp. 2 2 2 2 2 2 3 3 Ipomoea 2 2 4 7 2 2 3 4 Sinapis 1 2 6 6 1 1 2 3 Galium aparine 5 6 6 9 2 3 3 3 Viola tricolor 2 2 2 2 2 2 2 2

Effect Amount used kg active substance / ha Test plant 0.25 Compound No. 1 601 0.03 0.25 Compound No. 1 806 06 0,03 0.12 0.06 0.12 O. wheat 2 3 6 9 9 9 9 9 maize 1 2 3 5 4 5 5 7 Avena fatua 2 2 3 4 6 7 7 8 Alopecurus myosuroides 2 2 2 2 2 2 3 3 Echinochloa crus galii 2 2 2 2 4 5 6 6 Rottboellia exaltata 2 3 3 3 3 4 5 5 Cyperus esculentus 3 7 7 7 5 6 6 6 soya 2 2 3 3 2 2 3 3 cotton 2 4 6 7 2 2 3 3 abutilon 3 3 4 4 1 1 1 2 Beetle (Xanthium sp.) 1 1 2 2 3 4 4 5 Chenopodium sp » 1 1 2. 2 1 1 1 -2 Ipomoea 2 2 2 3 2 3 3 - 4 Sinapis 2 2 2 3 1 1 1 2 Galium aparine 2 2 4 6 3 3 4 4 Viola tricolor 1 2 2 3 1 1 2 2

Effect Amount used kg active substance / ha Test plant Compound No. 1,812 0.25 0.12 0.06 0.03 wheat 2 2 3 7 maize 2 2 3 4 Avena fatua 2 3 4 5 Alopecurus myosuroides 2 2 2 2 Echinochloa crus galii 2 2 2 2 Rottboellia exaltata 2 2 3 4 Cyperus esculentus 3 3 4 4 soya 2 2 2 2 cotton 2 2 2 3 abutilon 1 2 2 2 Beetle (Xanthium sp.) 1 1 2 2 Chenopodium sp. 2 2 2 4 Ipomoea 2 2 3 3 Sinapis 1 1 > 1 2 Galium aparine 2 2 3 4 Viola tricolor 2 2 2 3

Effect of Compound No. 1,899 Compound No. 1,901

Quantity used

kg active substance / ha Test plant 0.12 0.06 0.03 0.015 0.5 0.25 0.12 0.06 barley 5 6 6 7 7 8 8 8 páenice 6 7 7 8 9 9 9 9 maize 2 2 3 4 2 3 6 7 Sorghum (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 myosuroides 1 1 1 2 2 2 2 2 Digitaria sanguinalis 2 2 2 3 2 2 3 4 Echinochloa crus-galli 2 2 3 3 2 2 3 3 Sorghum halepense 3 3 3 3 4 5 5 7 Rottboellia exeltata 3 3 3 4 1 1 1 2 Cyperus esculentus 3 4 4 5 2 2 2 2 soya 2 2 2 2 2 2 2 2 cotton 2 2 2 2 1 1 1 1

Effect Amount used kg active substance / ha Test plant 0.25 Compound No. 1,900 Compound No. 2 113 0.12 0.06 0.03 0.25 0.12 0.06 0.03 barley 7 8 9 9 - - - wheat 9 9 9 9 4 4 7 9 maize 4 6 6 8 2 3 7 9 Sorghum (Sorghum hybr.) 4 5 7 8 - - - - Avena fatua 8 9 9 9 2 2 4 9 Bromus tectorum 5 6 6 8 - - - - Lolium perenne 2 3 4 6 - - - - Alopecurus myosuroides 2 3 4 4 1 1 2 2 Digitaria sanguinalis 3 5 7 9 - - - - Echinochloa crus-galli 4 6 6 7 1 2 2 2 Sorghum halepense 4 6 7 9 - - • - Rottboellia exaltata 5 6 7 8 2 3 3 8 Cyperus ^ esculantus 5 5 6 7 4 6 9 9 soya 2 2 3 4 2 2 3 3 cotton 2 2 3 4 2 2 3 6

Effect Compound No. 1899 Compound No. 1901 Quantity used kg of active substance / ha 0.12 0.06 0.03 0.015 0.5 0.25 0.12 0.06 Tea plant

abutilon Sida spinosa Xanthium sp. Amaranthus retroflexus Chenopodium sp. 1 2 3 1 2 2 2 3 1 2 2 2 3 1 2 2 2 3 1 2 1 1 1 1 1 1 1 1 2 1 1 1 1 2 2 1 1 1 2 2 Solanum nigrum 2 2 2 2 1 1 2 2 Ipomoea 2 2 2 2 1 1 1 2 Sinapis 1 1 1 2 2 2 2 Stellaria 1 1 1 1 2 2 2 2 Chrysanthemum leucotr. 1 1 1 1 2 2 2 2 Galium aparine 1 1 3 4 2 2 3 4 Viola tricolor 1 1 1 1 2 2 2 2 Veronicé sp. 1 1 1 1 1 1 1 1

ÚSinek

Amounts used kg active substance / ha Test plant

Compound No. 1,900 Compound No. 2,113

0.25 0.12 0.06 0.03 0.25 0.12 0.06 0.03 abutilone

Xanthium sp. Amaranthus retr. Chenopodium sp. Solanum nigrum Ipomoea Sinapis Stellaria

Chrysanthemum leuc. Galium Aparine Viola tricolor Veronica sp.

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

2 3

3 3

2 2

2 7

2.2

3 7

12

Example 17

Evidence of herbicidal effect after emergence of plants (contact effect)

A number of weeds and crop plants, both monocotyledon and dicotyledonous, are sprayed after emergence, at the 4-6 leaf stage, with an aqueous dispersion of the active ingredient at a rate of 4 kg of active ingredient per hectare and then kept at 24-26 ° C. and at 45 to 60% relative humidity. 15 days after treatment, the experiment is evaluated and the effect is scored according to the same scale as in Example 15.

Compounds of formula A were used at the same concentration as the comparator in this experiment

OCH.

77 ^SO and ^NH ' ^CO - ^NH

Ct

U 'Kl

OCHj known from Example 2 of the European Patent Application δ. 1485.

Post-allergenic effect Amount used: 4 kg of active substance / ha

Compound C. Avena Setaria Lolium Solanum Sinapis Stellaria Phaseolus 1 6 9 3 2 2 3 4 2 7 8 4 4 2 4 4 75 7 8 3 3 3 4 3 76 6 8 4 4 3 4 3 77 7 8 4 3 3 3 4 80 8 4 5 1 3 3 3 81 4 3 4 2 2 2 3 83 9 7 4 1 2 3 3 90 2 7 2 2 2 3 3 91 4 6 3 3 1 3 3 102 9 7 5 3 2 4 4 131 5 5 4 2 2 2 3 132 5 4 4 2 2 2 3 195 9 5 5 1 2 3 3 196 6 6 5 4 3 3 4 200 9 6 5 2 2 4 4 301 9 6 5 2 3 4 4 302 8 5 5 2 2 3 3 303 6 6 4 2 2 3 3 312 8 6 6 2 3 3 4 316 6 3 5 2 2 3 4 329 5 4 2 1 1 3 2 331 6 6 3 1 1 3 3 332 9 9 6 5 2 4 5 333 7 6 5 1 2 2 3 337 4 4 2 2 2 2 3 470 4 3 2 1 2 3 3 471 3 3 3 1 2 3 3 497 6 4 5 2 3 4 4 500 8 4 6 2 2 3 4 522 6 5 4 1 3 2 3 524 7 6 4 1 2 2 3 526 5 2 4 2 2 2 3 527 3 2 4 2 2 2 4 528 4 4 5 3 3 3 4 532 5 4 5 2 2 3 4 541 7 4 5 1 2 2 3 551 6 5 4 2 2 2 4 557 7 9 5 2 2 3 3 587 6 • 5 5 2 2 2 3 595 5 3 3 2 2 2 3

Post-emergence effect amount used: 4 kg of active substance / ha

Compound C. Avena Setaria Lolium Solanum Sinapis Stellaria Phaseolus 901 2 4 3 2 2 3 3 902 7 7 3 2 2 3 3 919 3 4 2 2 2 4 2 1 161 7. 6 4 1 2 • 3 4 1 202 3 3 3 2 3 4 3 1 203 4 2 4 3 2 2 4 1 212 7 6 4 6 3 7 7 1 223 3 4 4 1 2 2 3 1 242 6 5 3 3 1 2 3 1 244 4 4 4 2 2 2 4 1 245 5 4 3 3 2 4 5 1 252 6 5 4 3 2 4 4 1 453 • 2 1 2 1 2 2 3 1 454 2 3 2 1 2 3 3 1 455 2 3 2 2 2 3 2 1 456 3 5 3 1 2 2 3 1 457 4 4 3 1 2 3 4 1 60, 2 3 3 2 2 3 3 1 806 6 2 3 2 3 2 2 i 809 4 6 3 2 2 2 2 1 8,2 4 5 2 1 3 3 3 1 813 5 4 3 2 2 4 3 1 823 4 4 3 2 2 2 4 1 86, 8 8 '3 2 2 3 4 1 890 6 6 '4 1 2 2 3 1 893 4 4 2 2 2 3 2 1 898 4 4 3 1 2 2 2 2 004 2 2 3 2 2 2 3 2 101 2 3 2 2 2 2 2 2 102 2 2 3 2 2 3 2 2,10 ' 2 1 2 2 2 1 3 2 1,1 2 1 3 2 2 2 3 2 1.3 3 2 2 2 2 2 2 ‘ comparative substance A 9 7 7 3 3 3 5

In the test for herbicidal activity in post-emergence application, the compounds of formula I show a moderate activity against monocotyledons and a strong activity against dicotyledons. The comparative substance A known from the prior art, on the other hand, shows a slight action against monocotyledons and only a moderate action against dicotyledons.

The active compounds of the formula I therefore exceed the herbicidal activity, both in the case of the preemer. gentle as well as in the post-emergence application of the active ingredient known from the prior art, which are represented by the comparative substance A.

Fig. 1 a d 18

Proof of selectivity in post-emergence application

In the same experiment set-up as described in Example 17, a plurality of plants are treated with different rates of application. The results are evaluated according to the scale given in Example 15.

Test results (post-emergence effect)

Effect Amount used kg active substance / ha Test plant Compound No. 601 0.25 Compound No. 924 0.03 0.25 0.12 0.06 0.03 0.12 0.06 barley - - - - 9 9 9 ' 9 wheat 7 9 9 9 9 9 9 9 maize 3 4 7 9 . 9 9 9 9 rice (dry cultivated) 4 5 8 9 4 4 6 9 Avena fatua 4 5 8 9 - - - - Alopecurus myosuroides 1 2 2 2 7 9 9 9 Echinochloa C. g. 2 2 6 6 - - - - soya 2 3 3 3 1 2 3 3 bavlnlk 4 6 7 9 7 7 7 7 Abutilon 2 2 2 2 - · - - - Xanthium sp. 1 1 1 1 1 1 1 2 Amaranthus retroflexus - - - - 2 2 3 3 Chenopodium sp. 1 2 2 2 3 3. 4 4 Ipomoea 2 3 3 4 3 3 3 3 Sinapis - - - - 3 3 3 3 Stellaria 1 1 1 1 4 4 4 4 Chrysanthemum leuc. - - - - 3 3 3 3 Galium aparine 1 2 2 2 - - - - Viola tricolor 2 2 2 2 - -

Effect

Amount used kg active substance / ha Test plant

Compound No. 1 601

0,25 0,12 0,06 0,03 wheat barley 4 6 maize 2 4 rice (dry) 7 7

Avena fatua

Alopecurus myos. 2 3

Echinochloa c.g. 2 2 soya 4 4 cotton 9 9

Abotilon

Xenthium sp. 1 1

Amaranthus sp.

Chenopodium sp. 3 3

Effect Quantity used Compound No. 25 0,12 1 601 kg active substance / ha Test plant 0, 0.06 0.03 Ipomoea 2 2 2 2 Sinapis 2 2 2 2 Stellaria - - - - Chrysanthemum leuc. - - - - Galium aparine 2 2 4 4 Viola tricolor 2 2 2 2

Effect

Amount used kg effective flight / ha Test plant

Compound No. 1,899 Compound No. 1,901

0.12 0.06 0.03 0.015 0.5 0.25 0.12 0.06 barley 6 7 wheat 7 9 maize 2 7 dry rice 4 4

9 7 9 9 7 7

9

9

7

9

Avena fatua - Alopecurus myos. Echinochloa c. G soybean cotton

Abutilon

Xanthium sp. Amaeanthus retr. Solanum nigrum Ipomoea Sinapis Stellaria

Chrysanthemum leuc Galium Aparine Viola tricolor Veron! Ca sp.

4 3

3 1

11

3 4

4 4

2 3

2 2

13

7 3

3 6

2 6

4 4 1 1 1 1 2 2 4 4 4 4 4 5 3 3 3 3 4 4

3 3

6 6 6 6 6

Effect Compound No. 1,900 Compound No. Quantity used kg of active substance / ha 0.25 0.12 0.06 0.03 0.25 0.12 0 Tested plant

barley 89 wheat 9 9 maize 3 6 dry pistached rice 4 4

9 9 '

9 9

6 6 '

Effect Amount used kg active substance / ha Test plant 0.25 Compound No. 1 900 06 0,03 Compound No. 2 113 0.12 O, O, , 25 0.12 0.06 0.03 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 ά 2 2 2 2 soya 2 2 2 1 2 3 4 4 4 cotton 3 4 5 6 9 9 9 9 Abutilon 2 2 3 3 6 7 8 9 Xanthium sp. 2 2 2 3 1 1 1 2 Amaranthus retr. 2 3 3 3 - - - Ghanopodium sp. 2 2 4 4 3 6 6 7 Solanum nigrum 5 6 6 7 - - - Ipomoea and 4 4 4 5 6 6 7 Sinapis 2 2 2 2 4 4 4 4 Stellaria 2 2 2 2 - Chrysanthemum leuc. 2 2 2 2 - - - Galium aparine 1 1 _ 1 1 2 3 Viola tricoloř 2 2 2 2 2 2 2 3 Veronica sp. 2 2 2 2 - - -

Example 19 V ·

Evidence of germination inhibition in stored potatoes

The germ-free Urgenta potatoes obtained on the market are washed and allowed to dry. Thereafter, these potatoes are each immersed in the active substance emulsion at different concentrations for 1 minute, placed in plastic dishes on filter paper and kept at 14 ° C and 21 ° C in the dark at 50% relative humidity. Evaluation was performed 34 days after application. The evaluation shall be carried out on the following scale:

| , no sprouts (as in the application) about 50% of the sprout suppression is formed as in the untreated control

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

Test results: germination inhibition in stored potatoes

>> (4 Ή i — 1 Λ (0 Ρ χο C. Ρ tS3 weight («) Μ Μ- ΡΊ <\ ι WHAT 1 ο O Ρ ti σ \ Μ · 0 Μ Ρ · » Μ Ο β ~ Ο ΙΛ t- ti ο> » IN- t- CJ Ρ X Ο • rl £ «4 CL X ti * 3 > > 5 Ρ O ω • Ό > O ο σ \ Ο 03 / X ti <~ χ λ · » Μ rH X Ρ it ο (* Ί σ \ -Μ ο ΙΛ m ω 1 X ti • Ο φ Μ > ti »Ο σ \ Γ> fr- ο X fc> X X ΛΙ • Η Ρ >, W N 0 Ο Μ- ΙΛ X Ρ ti * » »» Μ X • Λ Ρ Ο ΙΛ ιλ 2 ti Q «- Ρ Ν 2 1 ο Ρ ti 10 Ρ »- O ο ti ·. O ti ο Ο Ο σ \ Ρ X> » ο ο X w- 1 • H * 4 and Ή «Μ * 5 Ρ > O & Μ Ο 00 oo Ό > ο ti ζ-χ · » Μ £ 0 X Ρ 00 (Μ Ο X ο ΙΓ \ 8 Μ 3 X ti • 3 φ ΛΙ > ti > ϋ σ \ - ο X > X Η -Μ Φ Φ 1 Ν ω Φ ti Whose Φ χρ X> 5 P CL ti · Ti3 ti ti (0 φ 3 Ο ο ο ο ω ti ρ > ti Χ3 ο ο O ω ο a a ο ο ti β Φ ο, O φ ο CL ti CL ~ - «- M ο Ό Λ X) - φ 1 • Η φ χυ Ο XD Η σ \ ο ti ω Ρ σ \ ο O ti ti οο σ> X Ρ Ο W > 4 Μ , -

Example 20

Evidence of growth suppression of legumes used in tropical crops as cover crops

The test plants (Centrosema plumieri and Centrosema pubescens) are grown to the final growth stage and then cut to a height of 60 cm. After 7 days, the active ingredient is sprayed in the form of an aqueous emulsion. The test plants are maintained at 70% relative humidity and under artificial lighting at 6000 lux per day for 14 hours, at 27 ° C during the day and at 21 ° C at night. The experiment is evaluated 4 weeks after application.

When evaluating with

(a) estimate the new growth in% of control

(b) a new% increment for control shall be considered; and

(c) the phytotoxicity shall be evaluated according to the following linear scale: dead plants,: undamaged plants.

Test results: inhibition of leguminous crops used in tropical areas as cover crops

Plant Compound number Used amount g / ha A new addition by visual assessment % control New addition weight Phytotoxicity & % control Centrosema pubescens 1 899 10 0 2 4 8 1 899 30 10 9 18 8 1 899 '00 0 2 4 8 1 900 10 0 1 2 9 1 900 30 0 2 4 9 1 900 100 ALIGN! 0 0 0 9 Centrosema plumieri , 899 10 20 May 31 50 9 1 899 30 0 0 0 8 1 899 , 00 0 4 6 8 1 900 , 0 30 29 47 9 1 900 30 10 26 42 9 1 900 100 ALIGN! 0 6 10 9

SUBJECT OF THE INVENTION

Claims (24)

A herbicidal and plant growth inhibiting agent comprising at least one N-phenylsulfonyl-N'-triazinyl- or pyrimidinyl-urea derivative of the formula I as active ingredient. Τ) Z 3> M ^{x in} SO-NH-C-NH-X ^/ V N = < (I) <X ~ A> “in which A is halogen, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkoxy, C 1 -C 4 haloalkylthio (C 4 -C 4), (C 1 -C 4) haloalkylsulfinyl or (C 1 -C 4) haloalkylsulfonyl, substituted (C 1 -C 6) alkyl or optionally substituted (C 2 -C 6) alkenyl by the foregoing substituents, Έ means a methine group or nitrogen, X is oxygen, sulfur, sulfinyl or sulfonyl, Z represents oxygen or sulfur, means Number 1 or 2, R 1 is hydrogen, halogen, C 1 -C 5 alkyl, C 2 -C 5 alkenyl or -ϊ-R 3 R ₂ is hydrogen, halogen, C 1 -C 5 alkyl, C 2 -C 5 alkenyl, C 1 -C 4 haloalkyl, or -YR 4, -COOR 9, -NOg or -CO-NR y. -Rg, R ₃ and R ^ are independently hydrogen, alkyl of 1-4 carbon atoms, alkoxy having 1 to 4 carbons, alkylthio having 1 to 4 carbon atoms, hslogenalkylovou group having 1 to 4 carbon atoms, halogen or alkoxyalkyl having not more than 4 carbon atoms, ^R 5 ^R 6 are alkyl of 1 to 5 carbon atoms, alkenyl of 2 to 5 carbon atoms, or alkynyl of 2 to 6 carbon atoms, R? and R 8 are independently hydrogen, C 1 -C 5 alkyl, C 2 -C 5 alkenyl or C 2 -C 6 alkynyl and Y represents oxygen, sulfur, a sulfinyl or sulfonyl bridge, or a salt thereof. 2. A composition according to claim 1, wherein the active ingredient comprises at least one compound of formula (I) wherein: A modified haloalkyl radical having 1 to 6 carbon atoms, E represents a methine group or nitrogen, X is oxygen, sulfur, sulfinyl or sulfonyl, Z 3 is oxygen or sulfur, m is 1 or 2, R 1 is hydrogen, halogen, C 1 -C 5 alkyl, C 2 -C 5 alkenyl or -Y-R 6; R ₂ is hydrogen, halogen, C 1 -C 5 alkyl, C 2 -C 5 alkenyl, C 1 -C 4 haloalkyl, or -Y-R 1, -COOR 8, -NO _2, or -CO- NR ^ -Rg, R1 and R2 are independently hydrogen, C1-C4alkyl, C1-C4alkoxy, C1-C4alkylthio, C1-C4haloalkyl, halogen or alkoxyalkyl of at most 4 carbon atoms, R 8 and R 8 are independently C 1 -C 5 alkyl, C 2 -C 5 alkenyl or C 2 -C 6 alkynyl, R y and R g are each independently hydrogen, (C 1 -C 5) alkyl, (C 2 -C 5) alkenyl or (C 2 -C 6) alkynyl, and Y is oxygen, sulfur, sulfinyl or sulfonyl. 3. A composition according to claim 1, characterized in that it contains at least one compound of the formula I in which Z is sulfur, X is oxygen or sulfur, R1 and R1 are independently C1 -C3 alkyl. C 1 -C 3 alkoxy or C 1 -C 3 alkylthio and together contain up to 4 carbon atoms and A is -CH ₂ -CH = CH ₂ , -CH ₂ -CH = CH-CH ₃ , -CH ₂ -C (CH ₃ ) = CH ₂ , methoxyethyl, methoxymethyl or -CCl = CHCl and the radical -XA occupies position 2, and the remaining symbols are as defined in 1. 4. A composition according to claim 1, characterized in that it contains at least one compound of the formula I in which R @ 1 and R @ ₂ are hydrogen, X and Z are oxygen, E is nitrogen, R @ 1 is methoxy, R @ 3 is methyl or methoxy and A is difluoromethyl, with the -XA residue at the 2-position on the phenyl ring, where X can also be sulfur when R 1 is methyl. 5. A composition according to claim 1, wherein the active ingredient is N- (2-allyloxyphenylsulfonyl) -N'-C4-methoxy-6-methyl-1,3,5-triezin-2-yl) urea. 6. A composition according to claim 1, wherein the active ingredient is N- (2-difluoromethoxyphenylsulfonyl) -N (4,6-dimethoxy-1,3,5-triazin-2-yl) urea. 7. A composition according to claim 1, wherein the active ingredient is N- (2-difluoromethoxyphenylsulfonyl) -N '- (4-methyl-6-methoxy-1,3,5-triazin-2-yl) urea. 8. A composition according to claim 1, wherein the active ingredient is N- (2-difluoromethylthiophenylsulfonyl) -N '- (4-methyl-6-methoxy-1,3,5-triazin-2-yl) urea. 9. A composition according to claim 1, wherein the active ingredient is N- [2- (1,1,2,2-tetrafluoroethoxy) phenyl sulfonyl] -N '- (4-methyl-6-methoxy). -1,3,5-triazin-2-yl) urea. 10. A composition according to claim 1, wherein the active ingredient is N- (2-trifluoromethoxyphenylsulfonyl) -N '- (4-methyl-6-methoxy-1,3,5-triazin-2-yl) urea. 11. The composition of claim 1, wherein the active ingredient is N- (2-trifluoromethoxyphenylsulfonyl) -N '- (4-methyl-6-methoxypyrimidin-2-yl) urea. 12. A composition according to claim 1, wherein the active ingredient is N- (6-chloro-2-difluoromethoxyphenylsulfonyl) -N (4-methyl-6-methoxy-1,3,5-triazin-2-yl) urea. p 13. A composition according to claim 1 which comprises as an active ingredient N- (2-difluoromethoxy-5-fluorophenylsulfonyl) -N '- (4-methyl-6-methoxy-1,3,5-triazin-2-yl) urea. 14. A composition according to claim 1, wherein the active ingredient is N- (2-difluoromethoxyphenylsulfonyl) -N '- (4-ethyl-6-methoxy-1,3,5-triazin-2-yl) urea. 15. A composition according to claim 1, wherein the active ingredient is N- (2-difluoromethoxyphenylsulfonyl) -N (4,6-diethoxy-1,3,5-triazin-2-yl) urea. 16. A composition according to claim 1, wherein the active ingredient is N- (2-difluoroethoxyphenylsulphonyl) -N ' - (4-chloro-6-methylpyrimidin-2-yl) urea. 17. A composition according to claim 1, wherein the active ingredient is N- (2-pentafluoroethoxyphenylsulfonyl) -N '- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) urea. 18. The composition of claim 1, wherein the active ingredient is N- (2-difluoromethylthiophenylsulfonyl) -H'- (4-chloro-6-methoxypyrimidin-2-yl) urea. AND 19. A composition according to claim 1, wherein the active ingredient is N- [2,5-bis- (difluoromethoxy) phenylsulfonyl] -N '- (4-methoxy-6-methyl-1,3,5-triazine). -2-yl) urea. 20. A composition according to claim 1, wherein the active ingredient is N- (2-difluoromethoxyphenylsulfonyl) -1 '- (4-methoxy-6-isopropyloxy-1,3,5-triazin-2-yl) urea. . 21. A composition according to claim 1, wherein the active ingredient is N- (2-difluoromethylthiophenylsulfonyl) -N '- (4-ethyl-6-methoxy-1,3,5-triazin-2-yl) urea. 22. A composition according to claim 1, wherein the active ingredient is N- (2-difluoromethoxyphenylsulfonyl) -N ' - (4-chloro-6-methoxypyrimidin-2-yl) urea. 23. A composition according to claim 1, wherein the active ingredient is N- (2-pentafluoroethoxyphenylsulfonyl) -N '- (4,6-dimethoxy-1,3,5-triazin-2-yl) urea. 24. A process for the preparation of an active ingredient according to claim 1, wherein the phenylsulfonyl isocyanate or isothiocyanate of the formula XV (IV) wherein A, R @ ₁ , R @ 8, m, X and Z are as defined below. I, optionally in the presence of an amine-acting base of the formula ^R 1 N-T «Κ'Λ NH. _(v) ^R wherein E, R1 and R1 have the meanings given in item 1 at temperatures between -20 and +120 ° C and the compound obtained is optionally treated with an amine, an alkali metal hydroxide or an alkaline earth metal hydroxide or a quaternary ammonium base converts to a base addition salt.