DE1812206C - N- (3,5-dichlorophenyl> imide, process for their preparation and their use as antimicrobial agents - Google Patents

Description

and tlas
mel I h

Those obtainable by the process of fruulung 2o imides of the general formula I hestl / en antimicrobial Akiivilät towards the most diverse palhogenic Bacteria and fungi such as Piricularia ory / ae, Cochlioholus iniyabeanus. Pelliculari;.! sasakii. Sphaerotheca fiiliuinea. Botryiis cinerea. Alternaria kiku-25 chiana, Alternaria muli. (ilonierella cingulata. Pythium aphanidermatum. Pellicularia lilamentosa. Fusarium, Cortieuni rolfsii. Sclerotinia sderoliorum. A.spergillus niger and Xanthoinonas ory / ae. Finige the test results confirm this activity N-O.S-dichlorophenyl succinimide of Form 30 are given below.

Cl

r egg

I!

C CII

C CH

(la)

Cl

Cl

I!

C ClI,

I.
C CH,

Il

Practice

A number of compounds having an N-l'henylmaleimide or N-phenylsuccinimide structure are known. Some of these compounds have a fungicidal effect against planar / enpathogenic fungi, but their effect is very weak. (Surprisingly, it was found that you 1.1 the N- (3,5-l) chlorophenyl) -imides of the general formula I have a very high antimicrobial activity against the most diverse plant-palhogenic hackleries \ ni \ fungi and / or parasites of Intluslrieproihikten. These high and wide antiniikrobielle activity animal compounds of general formula I is therefore unexpected and surprising because chemically structurally related compounds have no or only weak activity. Furthermore, the compounds of the general formula I have the important property that they do not cause any damage to plants when used for combating liana diseases.

The invention also relates to a process for the preparation of the N- (. 1,5-DiehlorpbenylHmide of the general formula I, characterized in that 3,5-Diehloranilin with maleic or succinic anhydride to 170 b ;, 2 (X) C is heated . no I osungs- "of diluent is required for this I Imsct / iing.

Di ·· Mcisniclc explain the discovery.

Attempt I.

The test compounds are applied as dusts in a dose of 1 (K) mg per 1 pot to ice plums which have been grown in pots ^{1 1} cm in diameter to the three-leaved stage. In later days the rice plants are infected with a spore suspension of Piricularia ory / ae. The number of digits initiated is calculated 5 days later. The results are shown in Table I /

table

KotuL'iii r.iihin /.1I1I the Vi-rbiniliint! iiili / icrlci SilHcm | H 10 lll.illcr N- (3.5-dichloiphenyl) - 3.0 succinitr.id η N- (3.5-dichlorophenyl) - 3.0 maleiinmid .1.0 0 N-l'henylmaleimide ... K) H N- (2,4-l) dichlorophenyl) - .1.0 succinimide 0.2 «) 65 l'henyl mercury acetal 3 untreated 117

^f) 5 attempt 2

The test compounds are diluted in the form of a benel / baren powder with water in a

ί 812

ML-ntic of 7 ml per peacock rice plants were applied, which were grown in dots with a diameter of 4 cm. Inen I was flush valves feed the plants with a Sporciisiispcnsioii of (iiL'hlioholus iniyaheaiuis infected. 4 position later sMiil the / aiii of infected sites per sheet calculated. Pa · l-rgehnisse are zusammengesiclll in I ahelle 11th

labile 11

V ulniuliini!

-'- i> ichlorpheiiyl) -

ι;. ^; -i iichlorphenyl) -tnaleinmiid

I nheluiidelt

K iMl / t'lllr.lllol

ppm

5 M)

5 (X)
5 (K)

Aihl animal
Make pm HI, St.

Ο, Κ
0

12.5
19.4

Attempt 3

DiL- \ ersuclisverbindungen are applied as aqueous l-nicion in an amount of! ') Ml per pot on rdspllaiizen, which up to a height of 6 (IlIH in KK) ml cup-sized glass jars were drawn, lines, later the lilall sheaths are in one Mycel-Veheibeniiioculuin with a Diirchiue.s-.er from 5 now inoculated. 5 layer washer, the / aiii tier infi / icrteii BlaUschekien is calculated. The results are in Table JIi. compiled.

\O

label III

\ 1.1 h ι η 111 μ ι μ

N- (3,5-dichlorophenyl | -
succinhnid

N- (3,5-dichlorophenyl) -inaleinimide

N- (2, i) -Dic!;! Orphenyl) -succininiid

ChIi) I melhansulfon-3,5-dichloroanilide. . .

I treated !!

KlMI / l'llll.lllllll

I ¹ I ¹ "'

KMK)
KKM)
KKK)
KMKI

ieiu

111.lli ^ lli UkTl

0
0

5 (.. 2

37.7
K) O

Attempt 4

7 healthy fruits from strawberries in the first stage of ripeness are put into a different dispersion the trial connection. that as wettable The powder was present, immersed for K) minutes and then air-dried. Then the 1 rüchle in l'etri dishes and kept in a humid atmosphere. The fruits are made with a spore suspension sprayed by liotrytis cinerea and hot IS C incubated. 10 days later he was able to trade The formation of numerous spores is rumored to be observed, and the same will also be observed examined the treated fruits. The results are compiled in table IV. The degree of damage is calculated according to the following calibration:

Degree of damage -

_ (Infeklionsiiulex χ number of fruits)
(iesanit / ahl of the tested fruits * 3

KK).

The InfektioiiKiiulex is defined as follows:

Inletion index

D = no infected areas or spores ilen I rumor,

I --- infected Ciebiet less than 30 "».
1 --- included (iebiet 30 to SU ",,.
3 - infected (iebiet more than SO ", ..

1"

I; Vi'rhiinllltl)! ibelle IV V (3 vDichlorphenvl) -.uccinimide N- (3.5-dichlorophenyl) - maleiiiiniid N-1'lieiiylmalcinimid .. N- (2,6-dichlorophenyl) - succinimide (liloriiielhansulfon- 3.5-dichloriinili (l kttn / en- triilini) ppm KK) KM) KX) KX) KX)

I zeroth

I 1.3

28, f »
KM) O

SME)
87.7

• J.S.

KK) .O

KLO 60

or- Conc ■ - ■ -
(iifi / icrie Sihäili- connection tration fruit efficiency .. _. —_ - _ _.PR ^ln - Ό -. 2,4-dichloro-6- (2-ch anilino) -S-triazip ... KKK) 100.0 ^l '5.2 \ nhairy ... . . . . ! 100.0 10 (1.0 Attempt 5

The experiments are diluted as wettable powders with water and applied in an amount of 7 ml per pot to pumpkin plants that have been grown in pots up to the 3 to 1-leaf stage in pots with a diameter of 111 cm the lilies are sprayed with a Sphaerotheea fuligiuea Spoiensiispension. IU lage rinser, the outcome of the infection is determined on the upper four leaves. The damage is determined according to an evaluation scale divided into six classes: 0 = no disease spots or colonies on the ulcers to 5 = over the entire skin patches of disease or colonies. The results are compiled in label V. The degree of disability is calculated using the following equation:

Degree of injury - ■

Infection index / ahl der hliilter)
(iesaiitz number of sheets tested χ 5

KX).

8i2206

\ ChIIHlUIlP V 1000
5 (K) Si-Iiaclipu
μΠιι! S. N- (3,5-diclilorphenyl) -
succinimide kllM / L'lllMIIIIII
ppm K) (K)
5 (K) 0
2.6 table N- | 3,5-Dic!) Lorpheny!) -
maleinimid KKK)
500 0
3.5 N-plienyl maleimide 1000
5 (K) 46.0
54.7 N- (2,4-Diehlophenyl | -
succinimide KKK)
500 33.9 (chloromethanesulfone-
3,5-dichloroanilide 25 (K) 21.3
34.1 sulfur 3.2 Untreated 6th 53.1 attempt

I / 1

Minimum inhibitor con / rniralion of vaccination on the 5th day after million Parts r Toslorgaiiisniüs N- (3.51) .chlor N-I.i.ü-Diclilor- plicnyD-succin phcnv l) -ma lcin- imid imid Piricularia oryzac 2 (K) Cochliobolus 2 (K) miyabcanus 200 8th Allernarit kikuehiana 200 40 Alternaria mali l'vthium aphanidcrmatum .... 40 8th Pcllicularia sasakii .... 40 Pcllicularia fiiamcntosa 8th Helminlhosporium 200 sigmoidium - Fusariuni oxysporuin 200 f. niveum 200 (ortiuum rollsii 200 K Hotrylis cinerea 2 (K) (ilomerclla cingulata .. 200 Xanlhomonas ory '.ac. . 2 (K) Aspcrgillus niger 2 (K) X Sclcroliniii sclcroiiorum

It became the toxicity of the fulfillment Compounds compared to similar compounds on mice and rabbits imlersuchi. the Results are given in Table VII below.

Table VII

N- (3.5-dichlorophenyl) malcinimide and N- (3,5-dichlorophenyl) succinimide have been tested for their antimicrobial effects against various harmful Microorganisms tested by the dilution method as follows. A solution of the connections in dioxane is mixed with a warm, sterilized potato agar medium in a proportion mixed with 1 ml of the solution per 10 ml of agar medium. The (icmisch is poured into Petri dishes and froze. Thereafter, each medium is mixed with a suspension of the test Microorganism inoculated. The concentration of the test compound in the agar medium is KKK), 2 (X), 40 or 8 parts / million. The results are shown in Table VI as the minimum concentration of the compound specified.

Table Vl

IO N- (3.5-dichlorophenyl) - I iac .-Unk- I liilLiMiL'hiL 'Vcrbindim; -' iTi'iIciniiTiid. . lii \: / il; ii I I) N- (3.5-dichlorophenyl) - (ηιμ Κμ. lira ¹⁵ siiccinimic! Mice N-phenyl maleimide KI (K) N- (3,5-dichlorophenyI) - Mice succinimide Mice 1000 20 phenyl mercury acetate. . 200 Rats Rats 1500 25 to 40

The N- (3,5-dichlorophenyl) -imides of the general l'ormcl I can be found in Torrn von Släubemilteln, wett- Arcn powders, emulsifiable concentrates or Granules are used. These agents contain at least one imide of the general formula I, optionally together with one or more solid or liquid diluents. Besides that can this middle! one or more known ones Fungicides such as ßlasticidin S, kasugamycin. Polyoxine, C'ellocidin, chloramphenicol, O, O-diethyl-S-benzylthiophosphoric acid, O-ethyl-S.S-diphenyldithiophosphoric acid, O - η - butyl - S - ethyl

5 - benzyldithiophosphoric acid ester, (), () - diisopropyl-S-benzyl thiophosphoric acid ester, O-ethyl-S-benzylphenylthiophosphonic acid ester,! 'Cntachlorbene / aldoxime, pentachlorobenzyl alcohol. Pentachloromandic acid, pentachlorophyllacelate, ice methyl arsonate, iron ammonium methyl arsonate. ; ■ -1,2.3.4,5, 6-hexachlorocyclohexane, 1,1,1 - trichloro - 2.2 - bis (p-chloropheriyl) ethane. O, O-dimethyl-O- (p-nitrophenyl) -thiophosphoric acid estjr. S- [l, 2-bis (ethoxycarbonyl-ethyl-O-O-dimethyldithiophosphoric acid ester, (), () - dimethyl-S- (N-methylcarbamoylmethyl) -dilhiophosphoric acid ester, O-ethyl-Op-nilrophenylphcnyllhiophosphonic acid ester, u - Methyl carbamate, O. O-dimethyl -O- (p-nitro- m- met hy I-phenyl) -thiophosphoric acid ester, 3,4,5,6-tetrahydrophthalimidomethylchrysanthemate, 3,4-dimethylphenyl-N-methylcarbamate. (), O -Diethyl - () - (2-isoprop> l-

6 - methyl - 4 - pyrimidinyl) thiophosphorus. O.O - Dimethyl-2,2-dichlorovinylphosphaL 1,1 -Bis- (p-chlorophenyl) - 2,2.2 - trichloroethanol, 1,2 - dibiomethane. l, 2-l) ib »nm-3-chloropropane, zinc-ethylene-bis- (dilhiocarbamiit * Manganese ethyl bis (dithocarbamate). 2,3-dichloro-1,4-naphthoquinone, N- (Trichbrmethylthio) -4-cyclohexene-1,2-dicarboximide, N- (1,1,2,2-Te-irachloroethylthio) -4-cyclohexene 1,2-dicarboximide, 6-methyl-2,3-quinoxalinedithiol carbonate, tetrachloroisoplithalic acid nitrile, Sodium p-dimethylaminobenzene diazosuli'onate, 2,4-dichloro-6- (2-chloroanilino) -s-triazine, 2,4-dichlorophynoxyacetic acid, 4-chloro-2-methylphenoxyacetic acid, 3,4 - dichloropropionanilide, 2,4 - dichlorophenyl - 4 '- nitrophenyl ether. 2 - (hlor-4.fi - bis - (ätiiylamiiio) - s - iriazine and sodium N- (l-naphlhyl) -phthalamate. These antimicrobial agents can also contain one or more compounds mil insecli / idcr. namali / ider. acarixider

or herbicidal effect, as well as fertilizers. Soil treatment agents, Contains soil disinfectants or plant growth regulators. Examples of typical are antimicrobial agents

a) Dusts. by dispersing at least one cyclic imide of the general formula I as an active ingredient in a concentration of 0.1 to 30 percent by weight in an inert carrier. like talk. Dialomcencrde. Wood flour or lon. will be obtained:

b) wettable powder, which by dispersing at least of an imide of the general formula I as an active ingredient in a concentration of 0.1 up to 80 percent by weight in an inert, adsorbent carrier. like Diatomccncrdc. together with a wetting agent and / or dispersant, e.g. B. an alkali salt Alkyl sulfate. a partially neutralized sulfuric acid derivative of a petroleum or a naturally occurring glyceride or a condensation product of an alkylene oxide with an organic acid;

c) emulsifiable concentrates, which by dispersing at least one imide of the general Formula I as an active ingredient in a concentration of 0.1 to 50 percent by weight in an organic Solvents such as dimethyl sulfoxide. and an emulsifier named under b) Type to be produced:

d) granules. Dusts and aerosols that contain the imides of general formula I and

be prepared in the usual way.
Specific examples of antimicrobial agents are:

B e i s ρ i c 1 A ^

Parts by weight of N- (3.5-dichlorophenyI) succinimide and 97 parts by weight of clay are thoroughly mixed with one another mixed. A dust with percent by weight active ingredient is obtained, which is used as such can be.

Example B.

Ciew parts of N- (3.5-dichlorophenyl) malcinimide and 5 parts by weight of an alkylbenzenesulfonate as Wetting agents and 45 parts by weight of diatomaceous earth become thoroughly wettable with one another PuKer mixed with 50 percent by weight of active substance. For use, the preparation is diluted with water.

Example C

5 parts by weight of N- (3.5-Dichlorophcny!) - maleinimide. 5 parts by weight of a Polyoxyäthylcnalkylphenoläthers as an emulsifier and 90 parts by weight of Diniethvlsulfoxyd are combined to form an emulsifiable concentrate with 5 percent by weight of active substance mixed. For application, the disposable Concentrate diluted with water.

Example D

2 parts by weight of N- (3.5-dichlorophynyl) succinimide.

2 parts by weight of O-n-butyl-S-ethyl-S-benzyldilhiophosphoric acid ester and 96 parts by weight of clay are thoroughly mixed together to form a piece of material, which contains 4 percent by weight of the active ingredients. The dust can be used as such.

Example E.

2 parts by weight of N- (3.5-dichlorophenyl) maleimide.

3 parts by weight of pentachlorobenzaldoxime and 95 parts by weight Clays are thoroughly mixed together to form a dust that is 5 percent by weight contains active ingredients. The dust can be used as such.

Claims (3)

Patent claims: I N- (3.5-dichlorophenyl) -iniide of the general 1 ormel Il Cl I! ο CH = CH or the A the group
Is CH ₂ -CH ₂ -. 2. Process for the preparation of the N- (3.5-dichlorophenyl) imides according to claim 1, characterized in that that one 3.5-dichloroaniline with maleic or Succinic anhydride at 170 to 200 C erb it 7t. 3. Use of the Ni- (3.5-dichlorophenyl) -imidc according to claim I as an antimicrobial agent.