CS219934B2 - Fungicide means and method of making the active component - Google Patents

Abstract

Novel sulphonyl- or sulphinylacetanilides of the general formula I <IMAGE> in which R denotes <IMAGE> R1 denotes (C1-C4)-alkyl, halogen, (C1-C4)-alkoxy, (C1-C4)-alkylthio or (C2-C4)-alkenyl, R2 denotes hydrogen, (C1-C4)-alkyl or halogen, R3 denotes (C1-C4)-alkyl or halogen, R4 and R7 denote hydrogen or methyl, R5 denotes hydroxyl, (C1-C4)-alkoxy, (C1-C3)-alkylthio, (C1-C2)-alkoxyethoxy, amino, (C1-C2)-alkylamino, di-(C1-C2)-alkylamino or O-Cat, where Cat represents a cation equivalent of an inorganic or organic base, R6 denotes (C1-C8)-alkyl, (C1-C4)-alkoxy-(C1-C3)-alkyl, (C1-C2)- alkylthio-(C1-C3)-alkyl, (C1-C2)-alkylsulphinyl-(C1-C3)-alkyl, (C1-C2)-alkylsulphonyl-(C1-C3)-alkyl, (C3-C6)-cycloalkyl, (C1-C4)- halogenoalkyl, (C1-C4)-hydroxyalkyl, (C1-C2)-alkoxycarbonyl-(C1-C2)- alkyl, (C3-C4)-alkenyl, (C3-C4)-alkinyl, optionally substituted benzyl or optionally substituted phenyl, n = 0 or 1 and m = 0, 1, or 2, and process for their preparation and their use as pesticidal compositions.

Description

R1 is C1-C4alkyl or halogen,

Ra is hydrogen, C1-C4alkyl, halogen,

R3 is C1-C4alkyl, halogen,

R a and R 7 are hydrogen or methyl,

R represents hydroxyl, alkoxy having 1 to 4 carbon atoms, alkylthio of 1-3 carbon atoms, alkoxyethoxyskupinu having 1-2 carbon atoms in the alkyl part, amiyds ^to u ^{pi nu,} al ^ky lammos ^k u ^p yne with 1-2 carbon atoms dialkylamino having ^{1 and 2} carbon atom of the alk ^ ech SKU ^P inu - ^ - p Kah ^{Acquisition of consumption} FM ^z Kat denotes a cation equivalent of an inorganic or organic base, and preferably ^{N, K, 1/2} Ca, ammonium SKU ^{p-well, the R} 6 means ^p atoll SKU yne with 1-8 atom uMte ^y ^ ^l KDX and ^y and with ^{the plurality of projections} ldddu yne with ^p 1 ^{and 4} of ^Y ulihliu alkoxy No. ^& STI ash. to 3 carbons in said alkyl, cyklo219934 alkyl of 3-6 carbon atoms, haloalkyl sltupinu 1 ^and 4 of ^Y atoms, a hydroxyalkyl group having 1 to 4 carbon atoms, alkoxycarbonylalkyl skuprnu ^{1 and} 2, ^the atom ^Y uhlftu in. and ^o ox ^y Love ^{i of alkylene} moieties of, and ^LK en ^yl verifies a ^to u ^p yne with 3-4 carbon atoms, an alkynyl group is from 3-4 carbon atoms, benzyl which is optionally substituted by 1 or 2 radicals selected from C1-C4alkyl, halogen or nitro; a phenyl group which is ^C o ^or 1 and ^DE substituovža than 2 radicals from the group consisting of alkyl having 1 to 4 carbon atoms or halogen, n is 0 or 1, m is 0, 1 or 2 respectively.

Preferred radicals in formula I are:

R 1 represents an alkyl group having 1 to 2 carbon atoms or halogen;

R 2 is hydrogen, C 1 -C 2 alkyl, halogen,

R3 is chloro or methyl,

R 1 and R 7 are hydrogen or methyl,

R 5 is hydroxy, C 1 -C 2 alkoxy, C 1 -C 2 alkylthio, amino, C 1 -C 2 alkylamino, C 1 -C 2 dialkylamino,

R 6 represents an alkyl group having 1 to 6 carbon atoms, an alkoxyalkyl group having 1 to 2 carbon atoms in the alkoxy moiety of up to about 3 · carbon atoms in the alkyl portion, a cycloalkyl group having 3 to 6 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms , a hydroxyalkyl group having 1 to 4 atoms^y uhRm al^toox^ykarbon^yla^lkylovou slm C 1 -C 2 alkyl, C 3 -C 4 alkenyl, benzyl or benzyl substituted with C 1 -C 4 alkyl, halogen or nitro, n is 0 or 1 am 'means 0, 1.

It is known to use a variety of dithiocarbamates, such as Mancozeb or Maneb, to combat plant rot caused by fungi of the genus Phytophthora, or^Gamck^E tin compounds such as^pMklad Fentmacet^andt^, or a derivative^yperchlor methylmercaptan, such as Capta · fol, can be used to combat Phytophthora strains that attack the spikes and the stems grow above the ground.^soil vegetating^pPhyto leaders^phthora and Pythium, which attack the roots of plants, can not use these. resources to combat. It is further known that acylated derivatives of anilino-. acetic k^ysel^andn^y, eventually^pro^Frionov^E Acids as described in DOS 2,350,944, 2,513,730, 2,513,789, 2,515,091, 2,643,445, and 2,643,447, in addition to herbicidal activity, also have fungicidal activity against Oomycetes fungi.

It has now surprisingly been found that compounds of formula I according to the ^invention have ^the ající Except for their fungtoidrn ťičrneR zejmža against the Oomycetes belonging to the Phycomycetes class, such as Pythium, Phytophthora, Peronospora, Pseudoperonospora, and Plasmopara.

^In zhtodem ^they might said stoučenrn ^y combated: ^C o ^or A ^{de P} otlačovat t ^y that ^h ouby on various crop plants such as maize, rice, cereals, sugar beets, vegetables, cucurbits potatoes Rajs ^to YC ^h jabHčkách tartaric vines, hops, tobacco, and various citrusovnících žuzteh ^paprika, -On -okrasných plants kakaovnících, bananas and kaučukovnících, or ^you may occurrence c ^h a hu ^b to said plants zcete prevented. The compounds of formula (I) also partially act s-ystemically. These compounds can also be used as dressing agents for combating fungi seed borne on the seed or to combat ^{Erasing fy} tópato enních ^g · ^hr · uh · te.ré ^to the ^{- y} in ^y sk thujas -v -. · .Půdě.

. . ^-.-Effect of the compounds of formula ^{1 p d} le the present invention - can - among other things for the mark · - '-proto entirely surprisingly, that the corresponding alkylthioacetanilidy as described in the above Offenlegungsschrift 2,515,091, against fungi are Phytophthora, especially against the ^{hole h} in uM PhytopMžra ^y sk TuJ ^{y s} c ^s m in the soil, and against fungi of the genus Pythium very little fungicidal effect.,

The invention thus provides fungicidal compositions, which are characterized by containing one atespoň sloučesnin ^y · ^b ECN about it ^s formula I. The preparation of the compounds of formula I can be by different methods and can be performed for example according to the following procedures ^marked enýc ^h 1 and ^2.

1. Production sulfonylderivátů formula I ⁱⁿ him n is 1 · ^s town, the Mze ^p Rovai ^ga t c ^y reductive alkylation ^of an aniline derivative of formula IV wherein R, R, R, R 3 · m have the meanings given under the formula I sulfonylacetyl ato ^{h y g} Enid ožcžho formula ^V, wherein

Hal is a halogen atom, preferably chlorine or bromine, and

R 6 is as defined in formula I ·.

2. The preparation of the sulfinyl derivatives of the formula I in which n = 0 ^can be carried out by acylation of the aniline derivatives of the formula IV in which R, R1, R2, R5 and m have the meanings given under the formula I;

4- R ₆ SOCH 2 Ca

(IV) fVH)

\ 0CH2SR where

Hal represents a halogen atom, preferably chlorine or bromine, and

Re has the meaning given in formula I.

The reactions of Processes 1 and 2 are preferably carried out in inert solvents or diluents. Preference is given, for example, to hydrocarbons such as benzene, toluene, xylene, petroleum ether, cyclohexane, halogenated hydrocarbons such as chlorobenzene, carbon tetrachloride, ethers such ^as alkyl ether ^, dioxane of n-tetrahydrofuran ^, nitrile of acetenitrine, dialkylated anudipas such as methyl ester of dimethylformamide; like ^! ethyl acetate.

^R eakční temperatures are kňtickou ^con ditions, ranging preferably between - 20 ° C and 16 ⁰ ° C, especially between ⁰ and ¹⁴⁰ ° C.

Reaction ccording ^{p p p} Ostu of ¹ and ² may be carried out optionally in the presence of an acid acceptor. As acid-binding agents are, for example ^{trialkylamines,} ATO ^{j -} ^ ethylamino ^ inorganic bases such as oxides -hebo metal hydroxides, such as calcium oxide or- sodium hydroxide, or carbonates such as potassium carbonate. If the reaction is carried out in the absence of an acid binding agent, the reaction is preferably carried out at elevated temperature and removal of the hydrogen halide from the reaction mixture must be ensured.

Aniline derivatives of formula IV which are used as starting materials for this preparation can be prepared, for example, according to J. Org. Chem. 30, 4101 (1965), DOS 2 212 268, U.S. Pat. No. 4,012,519, Tetrahedron 1967, 487 and 493.

The acid chlorides of formulas V and VII can be prepared from mercaptoacetic acids or derivatives thereof by oxidation and subsequent conversion to the acid chloride by reaction with thionylchloride. [Cf. Chem. Ber. 29, 1139 (1896)].

When conducting the production of the compounds of the formula I according to any of the processes 1 and ² in the ^on-voltage maiden ^p Oust ^EDL ec ^h, in which one of the reactants is only sparingly soluble, it can accelerate the reaction reaches ut ^p r ^ID Amm the catalyst ^is, for example, crown ethers or quaternary ammonium or phosphonic salts, which are known as phase transfer catalysts.

Compounds of formula I in which R represents a group

CHs * COO o / I *

H

have asymmetric carbon atoms. These compounds are therefore generally occur as racemic mixtures enantiomernfch ^{é f} Orem. Enantiomeric forms have. different biological efficacy. Intentional synthesis of the pure D-isomer can be accomplished, for example, by fractional crystallization of anilinopropionic acid salts of formula VIII with optically active bases

NH-CHCOOH (VIII)

as cinchonine and with no ^{b-phenylethylamine} of tails krystahzarn anihnothiobutyro ^l of butyrolactone ^{A b s} ECN it VIIIa, p. optical active acids such as the D- or L-tartaric acid. In formulas VIII and VIIIa, the general symbols R1, R2, R3 and m have the meanings as in formula I.

It is also possible to deliberately synthesis, from optically active derivatives halopropionic acids, such as from L-2-chloropropionic acid, an optically active tosylate ester of lactic to ^y selrny or optically ^y akttvmch hategenbutyrothiolaktonů and anilines of formula IX in which Ri, R2 R 3 and m have the meanings as in formula I. This reaction is carried out predominantly as a reaction of SN 2 with inversion of configuration. This gives rise to ^{2,6-dimethyl-y} lanolins and L-2-chloropropionic acid or methyl ester of L-2-chloropropionic acid, preferably D-2- ^(2,6-d imethytemiino] propionic acid or its methyl ester.

Laid the ^{p dl} of ev ^y n and ^l Cutting contain the active ingredient of the formula I, generally at about 2 and ^95% H ^ ^ virtuous ^h above about n ^{d of from 5} to ^90% by weight. They can be used in the form of conventional powders, emulsifiable concentrates of sprayable solutions, dusts, mordants, dispersions, granules or microgranules in conventional forms.

íSmáčitetoé^pr^ášky are^exE^dstavov^andn^y water-dispersible preparations which, in addition to the active substance, are present in addition to the active ingredient. the diluents or inert substances also contain wetting agents, for example polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, alkyl- or alkylphenylsulfonates and dispersants, for example sodium lignin sulfonic acid, sodium 2,2'-dinaphthylmethane-6,6'-disulfonic acid, sodium dibutylnaphthalene or. also sodium oleoylmethyltaurine. They are produced in the usual way^, napnkted by grinding and allowed individual components.

Emulsifiable concentrates can be VYR ^ÁB ive out of five najprMad extended ^P U ^S Terni ^ú črnné The women in an inert organic solvent, for example butanol, cyclohexanone, dimethylformam ^{id u} x ^y ene, or ^which just in výševroucmh aromatics or uhlovodímc ^{h surcharge} dose is ^d but not by ^{H b} of někohka emulsifying ^camphor tor ^s. U ^{k H u} apalnýc činnýc ^{h to} tête by addition of a solvent can also be wholly or partly dispensed with. The following may be used as emulsifiers: calcium salts of alkylarylsulfonic acid,. such as calcium dodecylbenzenesulfonate, or neionogenrn emu g ^{Tor l y,} j and ^k of the poly ^glyco oles.ter · ^y fatty acids, alkylaryl polyglycol ethers, fatty alcohol and condensation products of propylene oxide condensates · _ fatty alcohol, propylene oxide and ethylene alkyl ^p ol y ^{YGL to} ole ^{t Hery,} fatty ^alkyl selrn and sorbitol polyoxethylensorbitanestery mast219934 NYCHA acids or polyoxethylenestery 'sorbitol.

After ^p peat obtainable ^t grinding úcrnné IAIK ^y finely · dis ^p ergovaným ^{i, p} evným ^and panicle ^m i, for ^{the example,} talc, ^EXAMPLE ro ^d him ^and yokes such as kaolin, bentonite, pyrophyllite or diatomaceous earth.

Granules may ^Y R ^ABE t nastrkáním active ingredient per granutovaný inert material or · nanesernm toncentr ^ herein effective curing fluid using ^ JldeL najmMad ^p ol ^y vin ^{y alcohol,} with ^{n e} salt of ^p ol ^y and ^k r ^-yl b ^{s ky} selin ^y or. ·. these mine oils are applied to the surface of carriers such as sand, kaolinite or granulated inert material. They may also be granulated VTO · ^d n ^{e s} nn ^EFFECTIVE substances manner BV ^y klým manufacture of fertilizer granules ^p OPŘ ^{IP ga} mixture with fertilizers.

In smáčltelných powders the concentration of active beginnings ^{e l y} · niaptíktad about 10 and ^90% hmotnostrnch ZB · ^y tek 0 to ^10% by weight consists of obv ^y · klých components of these compositions. In emulsifiable concentration camp M ^for the active substance concentration is about 10 to 80% by weight. Práštovité ^p rostrata většrnou ^{thanks to} contain 5 to ^20%. by weight of active substance, sprayable solutions approximately · 2 0 ^{and 2%} toot-nostrnch nn ^é ú ^{or substance.}

In granules, · active substance content depends partly also on whether the active compound is solid or liquid ·, and which auxiliary ranula ^g-border ostřed ^ ^ ak.

is used.

Furthermore, ·· · a ^b sahuj ^s stora said means or conventional adhesives, wetters, dispersants, penetrants, mpouštědla,. plnidtá or carrier ^{é alkyl} methacrylate.

For application, the concentrates are present in a form which is common on the market, or diluted in a customary manner, for example as wettable powders, emulsifiable konccntrátů dispersions, and ^Ca in this partially hedged mitoogranulátů using water. Powdery and granular compositions as well as sprayable solutions are usually no longer diluted with other inert substances prior to application.

If desired, mixtures or mixed formulations with other pesticidally active substances, such as insecticides, acaricides, herbicides, plant growth regulators, plants or fungicides, are also possible. Particularly also in the case of mixtures with fungicides, synergistic enhancements of the effect can be achieved.

The following examples illustrate the invention in greater detail:

A. When ^{y kl} ad Huštrupm ^PU with ^b productions ^would úihnných substances

PMkladl ^M eth ^yl - ² - [N- (mífthylsulf on 1 ^-yl acetate ^yl) -N- ^(2, 6-Dimethyl-butylphenyl ^{y y} l) ámind] propanoate

The procedure is analogous to that described in Example 3:

³ CHCO _of CH 1 ^P - O COC 1 H - S-CH.

^z ii o

O in Example 3:

Te ^p lota tanū 115 ° C to H6.

Example 2

Methyl 2- [N- (ethylsulfonylacetyl) -N- (2,6-dimethylphenyl) amino] propanoate

The procedure is analogous to that described above

CH ₃ / HCO ₃ CH ₃ · COCH 2 SO 4 · C 8 H 8

Melting point: 123-129 ° C.

Example 3

Methyl-2- [N- (n-propylsulfonylacetyl) -N-

- (2,6 ^ 111 ^ 1 ^^ 8 ^ 1 jamino ·] propanoate

To a suspension of 20.7 g (0.1 mol) methyl-4-NH-

- (2,6-Dimethyl-phthyl) -amino] -propanoate and 13.8 g (0.1 mol) of potassium carbonate in 100 ml of absolute acetoniiril are added at room temperature 18.5 g (0.1 mol) of n-propylsulfonylation. After stirring the mixture at room temperature for 12 hours, the potassium bicarbonate precipitate is filtered off, the filter is poured onto 1 liter of ice-water and extracted with methylene chloride, the methylene chloride phase is dried, then dried. methylene chloride was distilled off and the residue was recrystallized from toluene to give ^22.4 g (== ⁶³ % of theory) of methyl-2- [N- (n ^- petroleum sulfonic acid) -N- (2,6-dimethylphthyl) 124.5-125.5 ° C of the following formula

CH.

I ^u

CHCO 3 CH 2

COCH ₂ ~ ^) from ^{C 'f} žCHzcH ₃

12

Examples 4 to 112

Analogously as described in Example 3, the compounds shown in Examples 4 to 112. In summary form are radicals Ri to Re each nama after the last, the column of the table lists the identified physicochemical data, in Table 1 for compounds of the formula ^y Even pnkladech 4-95 and ^b in the ce ^{l 2 y P} ro compounds of formula I in examples 96 to. 112.

СО

о CD iry LO O см о O CM CM CM rH ιη t — 1

ЬО Л th tT it

ГС X К X о о о о о о о о о о о о о

XО X ω о оо оо оо го го о

ΙΚΪΪΪΙΙΙΙΪΙΪΚΙΚ I οοοοοωωωωωωωωωωω о д Д Дя ГС ГС ГС ГС Я X X и ГС я л к

ьо

ГС

formula I. η = 1, m = 0 or 1:

г-Н

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ЬО

toО ЬО дд о о »-! м i — t н ни ни н НЧ НЧ НЧ НЧ НЧ НЧ мч □ υοϋοϋυ cd о

ЬО ЬО

СНз СНз Н СНз —ОСНз. —СНгСНг = СН2 t, 93-93.5 ^О С

см

E

CO CD

Vp 0 <= co cm <& in in in

O

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CD 0 G 0 in CD CD CJ O UD ^ cm O 0 O O TO what ID řN 00 CM CO Ή rT rH 00 CM O F I 1 rH rH 1 AND in 1 1 00 in •AND AND AND OD OO rH rH CO rH τφ 00 rH, -A- _{t t} -AND* AND . -A A AND -AND

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CD

W ⁴ + H А * r <TT Τ 'Τ' + Г

AA Η + Μ Α Α ++ ++ to e ω to

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A A A AA A A A A ggggggggg it

WÍ g

to ooooooooo зсжадлжи

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I + T Α * AW ¹ WT ^ τ ·

А А А А А А А 10 О uo ΙΟ O10 wh wH А А W A * WH

Т A A T T AA

N 'N what eo N N <N o g gg g g o do it do it do it do

A A A A A A A o υ o ό o ϋ o

Ί> 00 CD O rT CM CM CO CO CO CO CO CO

CD it

CH3 C2H5 H - СНз —ОСНз —CHžCH = CH2 ’Φ in ´ φ příklad příklad Example Ri R2 R3 Ri Rs R6 physicochemical data number o

c аз co

tO o o

CD CO L · * t— <CM CM ID 1B

Q 0

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O O O ’Ф O O и тН 0 0 WHAT co what WHAT CM inin r-l rH 00 т-л r-Γ r-T II II 1 00 O CM S Й r4 O 4- » 0 0 Й Й O • 4-j

Д ГС Я ГС ГС ГС Я оооооооЯЯЯХ X ГС я

to Ю to n tb X X X X ж X ГС. о to to о to to О о to to to to to to

HrM ИМ ЦИ ψ Hr - I HrM - MM HrM MM MM MM НМ MMMm

Um. Um Um Um Um U-iUm.Um Um Um Um Um UmU o o o o o-q u o υ.οωω

MM ММ ММ ММ WM ММ Um Um Um Um Um Um

(DtsOSaWHNOWinOSCO ^ OHNaWlDCDISOOaOHNirWinCDNCO example Ri R? R3 Rá ¹ Rs R6 physicochemical data number

ω O O O WHAT LO in O r> vd СП m CM rH

to tototototototototo to H to .to и to ддджддкхддж xxxxxx _: у ucooooyou o ωοουο

XXUoSuyXXXX ® 9 <? Ххх '''· iniocn to ю it to this л нЦ * Λ * _{ooo Q o cQ}

Μ μπ Μ Μ MI 1_4 _ Ц-U-н ^н to to to to

Μ> —I г-I г-Ч> —I t

A _Γ ήϋϋϋϋ

CDOrHNCO ^ inCDSOOO) RH CM СП Tfl ^ t ^ OOOOCQOOOOOQOOOOOOOO Q) Q) O) CD Q5 Q)

Table 2, formula I, n = 1, m = 0 or 1:

example Ri Ra Rs Re R? tysical-chemmto number ¹ data

96 CHs CH5 H CH3 ^H te ^pl OTA point: ⁵⁴ ° C I 97 CHs CH3 H C2H5 H 98 СНз CHs H —N-CsH7 H 99 CH3 CHs H —I-C3H7 H 100 ALIGN! CH3 CHs H —CH2CH = CH2 H 101 CHs CHs H —N-C4Hg H 102 CH3 CHs H —C1-C4H9 H 103 Csme CHs H —C1-C4H9 H 104 CHs CH3 H —T-C4H9 H 105 CHs CH5 H -O H 106 CH3 CH3 H - -CH2CH2OC2H5 H 107 CH3 C2H5 H —CHs H 108 C2H5 C2H5 H —CHs H 109 CH3 CHs 3-CH3 —CHs H 110 Cl CHs H —CHs H 111 CHs CHs H —CHs CH 3 -; 112 CH3 CHs H ~ ^СН Г <2) H Examples 113 - - to 225 ^si C ^{10 H comm of} ice -o ^p cally aktwmmi slou- boron compounds ^- of formula ^I-D series of ^{p or} ad ^of the L-series. By analogy to j e described in These products are from the compounds mentioned in of Example 3, compounds were prepared mentioned in ^ s ^{an example,} a racemic respectable ^- - ^p ro- Tables 3 and 4 as examples 113 to 225. ducts differ adding "AD" or "AL" In summary form up report residues R 1 to R 3 to the example Clearly. ^In tabuto ⁵ these are optically R 6, n and m and . always in the last the ta- asset composite in ^straight íslu le ^{d br} NYCHA su ^b STI ^- Bulk commissioning ^{the y-zpstěná} fyztoálně chemmto tuenta ve formulas I characterize in addition to data, in Table 3 for compounds of the formula him - theirs specific rotation [α] D ° C. Výro- ce in the examples. 113 to 208 a in Table 4 and these compounds - is carried out analogously for compounds of formula I in Examples 209 as in the case of the relevant racemic to 225. ducts. In Table 5 is also shown selection of

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ТГ r4 t — l

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to κ o o I to

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it it it it it ЬО It To It To It To It ДЦХЖХЖ! to π я д я X ΚΪΙΙΙΪΚΙΙϋϋϋϋϋϋϋϋ 1 1 1 1 1 1 1 1 о о о о ω 0 1 X к К X к

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<MOOtJ1UOCD [^ COGDOt-HC \] OO ^ UO CD ^ ’^’ ^ ι ^ ’τττί Φ ^ ιηιηιηιηιο

НгННгННгННННННгНг-IH гЧ

157 СНз С2Н5 Н —СНз —ОСНз —СНгСН ^ СНг

158 СНз С2Н5 Н —СНз ОС2Н5 —СНз

159 СНз С2Н5 Н —СНз ОС2Н5 —С2Н5

160 СНз С2Н5 Н —СНз ОС2Н5 — I-C3H7

161 СНз С2Н5 Н —СНз О-П-С3Н7 —СНз co

P4

CD О CM CM CO LO LQ

II II

CM N CM Q o Д o

about what

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О 00 СО ° О Mi О О М1 СО о 23 оо ю но О Ш 1 Mi rH 1 II II М1 II 4-> со й й Q Q » . Q tí tí * - Й + J

U t

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It It It It 10 It It It it it's that it's that hhh-, ψ, —м-нннннин hL | hm ьи> -M ни ни hh M-t X ωωωωωωωωω 0 uuuuuo oooooooo 0 000000

to k E o o

it to it to hC hC! X qqqq υ coo ^uuuu it to it

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CO ID t> 4 00 $ о о CO CO r-) z CM CM CM CM CM §

Table of formula I, n i

0, m = 0 or 1:

example number

209

210

211

212

213

214

215

216

217

218

219

220

221

222

223

224

225

Table of formula I, Rs

R, i Rž R3 R6 R? physico-chemical data СНз СНз _; Н СНз Н СНз СНз . н С2Н5 н СНз СНз ; н —П-С3Н7 н СНз СНз / н —1-С3Н7 н СНз СНз н —CH2CH = CH2 Н СНз СНз ¹ н —П-С4Н9 Н СНз СНз н —C1-C4H9 н СНз СНз н —S-C4H9 Н СНз СНз н —T-C4H9 н СНз СНз н н СНз СНз ; н —CH2CH2OC2H5 н СНз С2Н5 н —СНз Н С2Н5 С2Н5 no —СНз н СНз СНз 3-СИз —СНз н С1 СНз н —СНз н СНз СНз н —СНз у * \ СНз СНз СНз н -сн ^) СНз 5 R4 '4' - = Н, m = 0, R · = —CHCOR5.R4 = —СНз:

D-form example number

AD

1AL

2AD

3AD

8AD

AD

113 AD

115 AD

120AD

121AD

9AD

122AD

208a AD

95a AD

9¾

Č-H

CHOR _{S 0} \ П ri (O) _tt

COR _S \ and ₂ -sr * II (0) _a

R1 Rz Rs

Re

L-form [а] о ° С specific n rotation

—СНз —СНз —ОСНз —СНз 1 [, ol] _D 22 ^o c = —36.86 ' —СНз -СНз —ОСНз —СНз 1 OJd ²² ° C = = +38.5 ⁰ —СНз -СНз —ОСНз -С2Н5 1 —СНз —СНз —ОСНз П-СЗН7 1 —СНз —СНз —ОСНз I-C3H7 1 —СНз —СНз —SCH3 —СНз 1 —СНз —СНз —ОСНз П-СЗН7 0 —СНз —СНз —ОСНз —СНз 0 [α] ο ²⁰ ° c = = -40.2 ⁰ —СНз —СНз —ОСНз —С2Н5 0 —СНз —СНз —ОСНз I-C3H7 0 —СНз —СНз —ОСНз t-C 4 H 9 1 101 - 102 ° C n _D ²⁰ = —21.9 ⁰ —СНз —СНз —ОСНз t-C 4 H 9 0 n _D i6 = 1,5378 [α] _D ²⁰ = = 19.9 ° —СНз —СНз —ОСНз 1-С8Н17 0 t 106 - - 107 ° C [l «] ²⁰ = = —14 ⁰ —СНз —СНз —ОСНз 1-С8Н17 1 n _D16 = 1.5239

_{[L] D} 20 ₌ -22.16 °

B. Examples illustrating composition and method of preparation of compositions

Example A

The dust is obtained when 10 parts by weight of active ingredient and 90 parts by weight of talc are mixed as inert substances and ground in a hammer mill.

Example 1 a. d · B

The water readily ^di s ^p er ^{g ovatelný,} deadly powder is obtained when 25 parts by weight of active substance, 64 parts by weight of quartz containing kaolin as · inert substance, 10 parts by weight of potassium ligninsulfonate and 1 part by weight of sodium oleylmethyltaurinu as wetting agent and the dispersant are mixed and the mixture is ground in a pin mill.

Example C

A water-dispersible dispersion concentrate is obtained by mixing 20 parts by weight of the active ingredient with 6 parts by weight of nonylphenol polyglycol ether (with 10 ethylene oxide units in the rest of the polyglycol ether), 3 parts by weight of isotridecanol polyglycol ether (with 8 ethylene oxide units in the rest of the polyglycol ether). a paraffinic mineral oil (boiling in the range of about 225 DEG C. to above 377 DEG C.) and grinding the mixture in a friction ball mill to a particle size below 5 .mu.m.

Example D

Emul ^g ovatelný ^to oncentr ^Whether zfeká of ⁵ parts of active substance 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of nonyl (10 ethylene oxide units in the polyglycol ether residue) · as emulsifier.

Example E

For ^Prior .elem production ^yg ranuUtu oiasahujPlio% ^a.i. Inn látl · ^s ^ ^p is oužije successors components:

^{5 D} I ^profiles masses ^{Prior Star} Inn

0.25 parts by weight of epichlorohydrin,

0.25 parts by weight of cetyl polyglycol ether,

3.5 parts by weight of polyethylene glycol, parts by weight of kaolin.

The active ^{material used and} the smfeí with epichlorohydrin ^ drine and the mixture dissolved in 6 parts by weight of acetone, whereupon polyethylene ^{Gly OL} and cetyl. The resulting solution was nastnk ^and on ^to aolrn Otom and ^p is an acetone by ^p in vacuo.

C. Examples illustrating biological activity: Example i

Olinek composites formula ^{1 p} ro ^those PytMum ultimum on pea

a) do ^kp l, o and ^p c ^{and also} to the ^P u ^d y

Hou and ^b is the ^y grown in ^{Pi No} No kuhuře and ^p is Otom smfeí ou with ^soil. The infected soil is filled as a substrate into pots and pea seeds are sown in the soil. After planting, the test applied by watering the fungicidal compound as an aqueous suspension in ^ZDY ovrc ^{HP P} ud ^y. Pntom the ^p ou ^Gd weighing active ingredient concentration of 200 ppm to 12 · (related eno ^F to the ^soil volume). Květmá ^No E was kept for 2-3 weeks in a greenhouse at 20-22 ° C and the soil is kept uniformly moist by lightly. When evaluated on Pythium fungus infestation is determined as the emergence of pea plants and the proportion of healthy and diseased plants compared to corresponding control plants, and the z ^p ^ ovídapcta uso ^b em vypofre efficacies.

The compounds of the formula (i) according to the invention cause a far-reaching ^{spread of} Pythium ultimum at an application rate of 200 ppm (efficiency is on average ^greater than ⁸⁰ %). Many compounds of Formula ¹ is excellently effective even at a substantially lower concentration, as shown by the test results are summarized in the ^b u ^{l i} and CE.

Table Ia

Action against Pythium ultimum after treatment of infected soil and subsequent sowing of healthy seed

Day 1: soil infection with Pythium ultimum and treatment with fungicidal compound, seed sowing

Day 14: Evaluation.

the compound of Example No. degree of effect in% at the concentration of the active compound in soil in ppm

200 ppm 100 ppm 50 ppm

1 100 ALIGN! 100 ALIGN! 100 ALIGN! 9 100 ALIGN! 100 ALIGN! 100 ALIGN! 113 100 ALIGN! 100 ALIGN! 100 ALIGN! 3 100 ALIGN! 100 ALIGN! 100 ALIGN! 2 100 ALIGN! 100 ALIGN! 100 ALIGN! 120 100 ALIGN! 100 ALIGN! 100 ALIGN! 21 100 ALIGN! 100 ALIGN! 100 ALIGN! 115 100 ALIGN! 100 ALIGN! 100 ALIGN! 8 100 ALIGN! 100 ALIGN! 100 ALIGN! 134 100 ALIGN! 100 ALIGN! 100 ALIGN! 121 100 ALIGN! 100 ALIGN! 100 ALIGN! 129 100 ALIGN! 100 ALIGN! 100 ALIGN! 148 100 ALIGN! 100 ALIGN! 100 ALIGN! 86 100 ALIGN! 100 ALIGN! 100 ALIGN! 130 100 ALIGN! 85 14 100 ALIGN! 100 ALIGN! 100 ALIGN! 16 100 ALIGN! 100 ALIGN! 100 ALIGN! 17 100 ALIGN! 100 ALIGN! 100 ALIGN! comparator A * 65 40 0 control: untreated, infected soil 0 (= 100% breakage damage) untreated, uninfected soil 100% emergence

*) Comparative A: methyl 2- [N- (methylthioacetyl) -N- (2,6-dimethylphenyl) amino] propanoate (cf. DOS 2,515,091).

b) Effect after application by pickling

The fungus is cultured as described in Example Ia and mixed with the soil. This soil is then filled into the test pots and pea seeds that have been soaked with the test stain products were sown in the soil. An active compound concentration of 1000 to 250 ppm (based on the weight of the seed) was used. The pots are placed for 2-3 weeks in a greenhouse at 20-22 ° C and the soil is kept evenly moistened slightly. The evaluation is carried out as described in Example Ia.

At a concentration of 1000 ppm, the compounds of formula I exhibit an average degree of action of greater than 80%. Many of the compounds of formula I offer, at an even lower concentration, complete control of fungal attack, as shown in the test results summarized in Table Ib below.

213334

T a b at 1 k and Ib

Action against Pythium ultimum, ^P by treatment (pickling) and pea seeds are sown in soil infected with

Day 1: infestation of test soil and sowing soaked pea seeds, as well as the three non-infested control pea seeds

Day 14: Evaluation.

Compound of Example No. ^P en úmnku growth in% ^p s ^p M ^or nn ^é ú ^Шк у seed weight

1000 ppm 500 ppm

1 100 ALIGN! 100 ALIGN! 9 100 ALIGN! 100 ALIGN! 2 100 ALIGN! 100 ALIGN! 3 100 ALIGN! 100 ALIGN! 115 100 ALIGN! 100 ALIGN! 121 100 ALIGN! 100 ALIGN! 134 100 ALIGN! 100 ALIGN! 8 100 ALIGN! 100 ALIGN! Control: uninfected seed, infected soil 0 [= 100%] O ^SK Oz ^p p ^s vzcMzem)

uninfected seed, uninfected soil ¹⁰ 0% emergence by grate

Example 1 a d. II

Preventive effect of compounds of formula I against Phytophthora capslci - application to soil

The phytoftor rot of the pepper (Phytophthora capsici) is grown in sandy culture and mixed. with soil. Infected soil at ^p m to toětináčů and ^P and ^K into the ^soil · sown the seeds of peppers (Capsicum annuum). After sowing, the compounds of the invention are applied in the form of aqueous suspensions to the soil surface. watering or working into the soil.

An active compound concentration of 200 to 12 ppm (based on ^soil volume) is used. N Kv ^{ng kids and} CE is ^p Otom about 3 ^d b ^y th place in a greenhouse at 22-24 ° C and the soil is kept uniformly moist. When evaluating the phytophthalic rot disease of the paprika, the emergence of the paprika plants as well as the proportion of healthy and sick are determined. of plants compared to the respective control and then the corresponding degree of effect is calculated.

The compounds of formula I are capable of almost completely suppressing the phytophthalic rot activity of the pepper at an application rate of 200 [mu] m. Many compounds of the formula I allows .. · still at a considerably lower amount of active substance applied is also almost completely suppressed at ^p pr ^s ou ^b ho ⁽⁰ to 5% of L j and ^{k p} ATRN from the results of experiments are summarized in Table II.

Table II

Activity against fytoftorové peppers rot (Phytophthora. Capsici) after treatment of infested soil fungicide compounds of Formula ¹ and after sowing a health club, a seed ^{EH p} apri ^alkyl

Day 1: infe tion ^to treat ^soil and fun ^g icidní slotóenrnou, sowing ^of seeds apri ^ky about day 21: evaluation.

compound ^No. Come Enina ^comm ice step ^accounts in ^the UV at ^pp m% ^Active substances in ^soils of usřo

200 ppm 100 ppm 50 ppm

1 100 ALIGN! 100 ALIGN! 9 100 ALIGN! 100 ALIGN! 100 ALIGN! 113 100 ALIGN! 100 ALIGN! 100 ALIGN! 3 100 ALIGN! 100 ALIGN! 2 100 ALIGN! 100 ALIGN! 122 100 ALIGN! 100 ALIGN! 100 ALIGN! 120 100 ALIGN! 100 ALIGN! 21 100 ALIGN! 100 ALIGN! 100 ALIGN! 115 100 ALIGN! 100 ALIGN! 100 ALIGN! 8 100 ALIGN! 100 ALIGN! 100 ALIGN! 23 100 ALIGN! 10Q 100 ALIGN! 139 100 ALIGN! 100 ALIGN! 100 ALIGN! 121 100 ALIGN! 100 ALIGN! 123 100 ALIGN! 100 ALIGN! 148 100 ALIGN! 100 ALIGN! 100 ALIGN! 129 100 ALIGN! 100 ALIGN! 134 100 ALIGN! 100 ALIGN! 100 ALIGN! 14 100 ALIGN! 100 ALIGN! 100 ALIGN! 16 100 ALIGN! 100 ALIGN! 100 ALIGN! 36 100 ALIGN! 100 ALIGN! 100 ALIGN! 68 100 ALIGN! 100 ALIGN! 100 ALIGN! 4 100 ALIGN! 90 28 100 ALIGN! 90 25 100 ALIGN! 100 ALIGN! 27 Mar: 100 ALIGN! 95 86 100 ALIGN! 100 ALIGN! 100 ALIGN! 130 100 ALIGN! 100 ALIGN! 171 100 ALIGN! 95 control: untreated, infected soil C ) (% ^P 1iOO O ^SK marries during germination) untreated, uninfected soil 100% emerging plants

EXAMPLE III ^Úč INEK composites formula I ^No backlash and ptísni ^b ramborové (Phytophthora infestans) on tomato (Solanum lycopersicum)

(a) Preventive effect:

Tomato plants (Solanum lycopersicum) of the species 'Rheinlandsruhm' are sprayed in the 3-leaf stage until the suspensions of the compounds of formula I are drenched using the active compound concentrations of 500, 250 and 125 mg / liter of spray suspension.

After the spray coating had dried after a ^ t ^ IRIKA the plant shade inoculated with ^a suspension zoosporangtí ^p distress potato (Phytophthora infestans) and one day are placed in a moist environmental chamber where the temperature is 16 ° C and relativrn humidity topics ^of R ¹ 0 ⁰ %. ^p Otom the plants are placed in a cold part of the greenhouse at 15 ° C and relative humidity mod ^d ear 90 and ^95%. After 7 days of incubation, they grow from ^being infected ^with the potato pests (Phytophthora infestans). The number and size of the typical spots of late blight on leaves are used as a benchmark for evaluating the effectiveness of test drugs ^{to la} te. Degree ^of infection was ^{characterized} nucleus in% infection ^pl och ^y compared neostřenými, ^and infected control plants (= 100% for ^p Aden).

In this test compounds of formula I ^{at p} ou ^f i th ⁵⁰⁰ mg / HTR-sus ssřikov ^{s p s} t Enzo capable ^{measurable UPL some} preventing fungus infestation. Some výsledtích testiů summarized in the ^b ulcerative lilia ^l shew that many of the compounds of formula ^I leads to the complete prevention of fungus infestation with even ^harder nl ^p odstatně m aphltovarám ^LeVeLs Community.

Table IIIa compound of Example No.% Phytophthora attack at mg active ingredient / liter spray suspension 500 mg 250 mg 125 mg

113 0 0 0 3 0 0 0 2 0 0 0 122 0 0 0 120 0 0 0 21 0 0 0 115 0 0 0 134 0 0 0 148 0 0 0 8 0 0 0 14 0 0 0 16 0 0 0 17 0 0 2 36 0 0 0 81 0 0 0 86 0 0 3 194 0 0 0 4 5 10 25 untreated, infected plants 100 ALIGN!

b) Curative effect

Plants through tomato (Solanum lycopersicum) type "Rheinlandsruhm" in the 3-leaf stage heavily inoculated with a suspension of zoosporangia of late blight (Phytophthora infestans] a. The plants are then kept for 24 hours in a climatic chamber at 15 ° C and a relative humidity of ^{almost 100} '% mkitéace putty.

After the plants have dried, the plants are sprayed with a suspension of the compounds of formula I using an active compound concentration of 500, 250 and 125 mg per liter of spray suspension, the spray suspension being prepared from wettable powder formulations. ^Then: the plants were again placed in a greenhouse kept at a temperature of about 16: about 18 ° C and retetívm atmospheric humidity of about ⁹⁰ and ^95%.

days later, the plants are examined for potato blight (Phytophthora infestans). The number and size of typical spots of Phytophthora on the leaves serve as a measure of the effectiveness of the active substances tested.

The degree of infestation is expressed as a percentage of infested leaf area compared to untreated, infected control plants (= 100% infestation).

Use of compounds of formula I 500 mg / liter of spray liquor almost entirely of ^{beta Tia CIs.} As shown ^{on the} y Equals tests summarized in table IIIb are numerous compounds of formula I in more odstatn ^P and ^{pl of} ntérnm The amplified amount to complete suppression of mold.

Table Illb

the compound of Example no. % ^P and ^{d P} Hout en ^s hyto Phytophthora pn ^p m ^{g EFFECTIVE} variables severe / LTIR ^p ost oic suspension ^RIK 500 mg ²⁵⁰ m ^g 125 mg 113 0 0 0 - 3 3 0 0 0 - 3 2 0 0 0 122 0 0 3 120 0 0 0 21 0 0 0 . 115 0 0 0 untreated, infected plants 100 ALIGN!

c) Preventive systemic effect

The compounds of formula I are applied in the form of an aqueous suspension prepared from a wettable powder at an active compound concentration of 200, 100, 50 and 25 ppm (based on soil volume) to the soil surface in which the "Rheinlandsruhm" tomato plants are planted. about 3 to 4 weeks old. Three days later, the plants are inoculated with a zoosporangia suspension of potato late blight (Phytoiphthora infestans) and then infected as described in Example IIIa. After an incubation period of 6 to 7 days, the plants are examined for infestation with potato late blight (Phytophthora infestans). The number and size of these phytophthora fungus spots formed on the leaves are a measure of the effectiveness of the test compounds.

The degree of infestation is expressed as a percentage of the infected leaf area compared to untreated, infected control plants (= 100% infestation).

With the compounds of the formula I, at an application rate of 200 ppm of active ingredient (based on the volume of the soil), fungal attack is almost completely prevented. As can be seen from the results of the tests summarized in Table IIIc, numerous compounds of formula I lead to complete fungal attack at still substantially lower rates of application.

Example compound% Phytophthora attack at ppm active ingredient in soil

200 ppm 100 ppm 50 ppm

113 0 0 121 0 0 134 0 0 148 0 0 149 0 0 8 0 0 10 0 0 14 0 0 16 0 0 36 0 0 37 0 0 194 0 0 infected plants, untreated soil 100 ALIGN!

0 0 0 0 0 0 0

U O č č

Example IV

Effect of compounds of the formula I on grapevine peronospora (Plasmopara viticola) on vines

Preventive effect

Grapevine plants grown from "Múller-Thurgau" vine shoots infected with peronospora of Plasmopara viticola are sprayed with aqueous suspensions of the test compounds of Formula I at 4-leaf stage until wet. The applied concentrations are 500, 250 and 125 mg. active ingredient / liter of spray suspension.

After the spray coating has dried, the plants are inoculated with a Plasmopara viticola zoosporangia suspension of grapevines (Plasmopara viticola) and in this state are placed in an air-conditioned chamber at a temperature of 20 ° C and a relative air humidity of about 100%. After 24 hours, the infected plants are removed from the air-conditioned chamber and placed in a greenhouse at 23 ° C and a relative air humidity of about 98%. After an incubation period of 7 days, the plants are moistened, placed in an air-conditioned chamber overnight, and allowed to develop disease. The degree of attack is then evaluated. The number and size of infectious spots on the leaves of inoculated and treated plants serve as a measure of the efficacy of the compounds of the invention, the degree of infestation being expressed in% of the infected leaf area compared to untreated, infected control plants (= 100% infestation).

The compounds of the formula I cause an average fungal infestation of more than 80% at an application rate of 500 mg of active ingredient / liter of spray suspension. As can be seen from some of the test results summarized in Table IV, the numerous compounds of formula I can achieve complete control of the fungus at an even lower application rate.

TABLE IV Compound of Example no.% Attack, while the fungus Plasmopara mg of variables ^or latte / liter ^p ost oic suspension ^RIK

500 mg 250 mg 125 mg 113 0 0 0 3 0 0 0 2 0 0 0 122 0 0 0 120 0 0 0 21 0 0 0 115 0 0 0 8 0 0 0 ^; 134 0 0 0 136 0 0 0 171 0 0 0 121 0 0 0 123 0 0 0 116 0 0 0 148 0 0 0 149 0 0 0 185 0 0 0 139 0 0 0 10 0 0 0 14 ..... 0 0 0 36 ..... 0 0 0 37 0 0 54 0 3 5 - 10 171 0 3 0 73 0 0 0 - 3 185 0 0 0 86 0 0 0 unglazed mfikovará plants 100 ALIGN!

SUBJECT OF THE INVENTION

Claims (3)

SUBJECT OF THE INVENTION A fungicidal composition comprising, as an active ingredient, at least one compound of the formula I in which: R is a radical of formula Ri is alkyl having 1 to 4 carbon atom in ^Y to ^HLI halogen or- ^R2 is? Vodfc, aloovou with ^k u ^pi AZ- comprising 1 to 4 carbon atoms, halogen, R3 is C1-C4alkyl, halogen, R a and R 7 are hydrogen or methyl, R represents hydroxyl, alkoxy having 1 to 4 carbon atoms, alkylthio of 1-3 carbon atoms, alkoxyethoxyskupinu having 1-2 carbon atoms in the alkoxy moiety, an amino-Buy-al ^ky lammosku ^p him having ^{1 and} 2 carbon with ^H L ^Cart for ^di al ^{ky p} lammosku him having 1-2 carbon atoms in the alkyl group, -O- -Kat wherein Kat denotes a cation equivalent of an inorganic or organic base, R e represents an alkyl group having 1 to 8 carbon atoms, an alkoxyalkyl group having 1 to 4 carbon atoms in the alkoxy moiety of up to 3 carbon atoms in the alkyl moiety, a cycloalkyl group having 3 to 6 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, hydroxyalkyl group having 1 to 4 carbon atoms, an alkoxycarbonylalkyl group, a 1-2 alkoxycarbonyl and ^alk yl ^é alkenyl having ^{3, and} C 4 alkynyl;⁴ atoms^{, k}te R 6 is optionally substituted with 1 or 2 residues^togroups^ytviořen^E al^kylovou sku^por (C 1 -C 4) halogen, or nitro^toupmou; hairdryer^ylkkunnn^ktthe radical is optionally substituted by 1 or 2 radicals from the group consisting of alkyl having 1 to 4 carbon atoms or halogen, n is the number · 0 or · 1, m is the number 0, 1 or 2. Composition according to Claim 1, characterized in that it contains from 2 to 95% by weight, preferably from 10 to 90% by weight, of the compound of formula I as active ingredient, the remainder up to 100% by weight consisting of auxiliaries such as adhesives, wetting agents, dispersing agents, emulsifying agents, penetrating agents, solvents, fillers or carriers. 3. A process for the preparation of an active ingredient according to claim 1, wherein the aniline derivatives of the formula IV are: R, R 1, R 2, R 3 and m have the meanings given in formula I, either with the sulfonylacetyl halides of the general formula V (V), R 6 -SO a-CH 2 -COHal in which: Hal represents a halogen atom, preferably chlorine or bromine, and R6 is as defined in formula I to form compounds of formula I wherein n = 1 or sulfinylacetyl halides of formula VII Re = SO-CH2-COHal (VII), (IV) wherein Re and Hal have the meanings given in formula V to form compounds of formula I in which n · = 0, optionally in each case with the addition of acid-binding agents, preferably always in inert solvents or diluents and preferably at temperatures between -20 and · 160 ° C.