CS243487B2

CS243487B2 - Fungicice and method of effective substance preparation

Info

Publication number: CS243487B2
Application number: CS843473A
Authority: CS
Inventors: Takahashi; Kato; Noguchi; Oguri; Yamamoto; Kamoshita
Original assignee: Sumitomo Chemical Co
Priority date: 1983-05-12
Filing date: 1984-05-11
Publication date: 1986-06-12

Abstract

Fungicidní prostředek vyznačený tím, ie jako aktivní složku obsahuje sloučeninu obecného vzorce I kde obecné symboly mají dále uvedený význam. Dále se popisuje způsob přípravy účinných látek.A fungicidal composition characterized by as the active ingredient contains a compound of formula I wherein the general symbols are as defined below. The method of preparation is described below active substances.

Description

The present invention relates to aniline derivatives with fungicidal activity.

Known benzimidazole and thiophanate fungicides, such as Benoayl (methyl 1- / butylcarbamoyl-benzimidazol-2-ylcarbamate), Fubelldazole (2- / 2-furyl / benzimidazole), Thlabendazole (2- [4-thlazolyl] benzimidazole ), Carbendazlm (methyl benzylimidazol-2-ylcarbamate), Thiophanate-methyl (1,2-bis- (3-methoxycarbonyl-2-thioureido / benzene), Thlophanate (1,2-bis / 3-ethoxycarbonyl-2) -thioureido / benzene), 2- (O, S-dimethylphosphorylaino) -1- (3'-ethoxycarbonyl-2'-thioureadiol / benzene and 2- (0,0-dinethylthiophosphorylamino) -1- (3'-ethoxycarbonyl) -2'-thioureldo) benzene exerts an excellent fungicidal effect on various plant pathogenic fungi and since 1970s widely used as agricultural fungicides. Due to their continuous application over a long period of time, phytopathogenic fungi have created a resistance to them and thus their preventive effect on plant diseases is considerably lower. Further, molds that have formed resistances to certain types of benziaidazole or thiophanate fungicides also exhibit some resistance to some other species of benziaidazole or thiophanate fungicides. So, capable of creating cross-resistance.

Therefore, if a reduction of the plant disease preventive effect is observed for some material, its application should be discontinued. However, it has often been observed that the density of fungicide resistant organisms is not reduced even after the application has been discontinued. While other types of fungicides may be used in these cases, only a few of them are so effective to control various phytopathogenic fungi, such as benzimidazole or thiophanate functionals. Benzimidazole and thiophanate fungicides are hereinafter referred to as "benzimidazole thiophanate fungicides".

Cyclic imide fungicides such as Procynidone (3- (3 ', 5'-dichlorophenyl) -1,2-dimethylcyclopropane-1,2-dicarboxiaid), Iprodlone (3- (3'-5'-dichlorophenyl) -1') -isopropylcarbamoyli-dazolidine-2,4-dione), Vinchlozolin (3- (3 *, 5'- / dichlorophenyl) -5-ethyl-5-vinyloxazolidine-2,4-dione), ethyl (RS / -3 / 3 *, 5'-dichlorophenyl / -5-ethyl-2,4-dioxooxazolidine-5-carboxylate and the like, which are effective against a variety of plant diseases, especially those caused by Botrytis cinerea, have the same drawbacks as explained above herbicides such as Barban (4-chloro-2-butynyl N- (3-chlorophenyl) -) from benziaidazole thiophosphate fungicides have been reported in CR Acad Science Paris 289 series D, pages 691-693 (1979). carbamate), Chlorobufam (1-methyl-2-propynyl N- (3-chlorophenyl) carbamate), Chlorpropham (isopropyl N- (3-chlorophenyl) carbamate) and Propham (isopropyl N-phenylcarbaaate) show fungicidal activity against certain organisms, which exhibit benzimidazole thiophase resistance However, their fungicidal effect on resistant molds is not high enough and therefore cannot be applied in practice as fungicides.

As a result of the study of the search for a new type of fungicide, a fungicidal composition has been found, characterized in that it comprises as active ingredient a compound of the formula X

X

N-C-BIIA

Z (I) wherein n is an amino group, aaino, isothiocyano, 1 and 2 carbonyl alkylano, or -NH-C-R 8,

A 3 243487 MH-CA "-R- or -MH-C-NH-R 1, II, 2 II, 2

AA where A 'and A "are the same or different substituents selected from the group consisting of oxygen or sulfur, R 2 is alkyl of 1 to 3 carbon atoms, alkenyl of 3 carbon atoms, alkynyl of 3 carbon atoms, or haloalkyl of 2 carbon atoms, or 2-methoxyethyl, Y is C 1 -C 3 alkyl, C 2 -C 3 alkenyl, chloroethyl, methoxyethyl, hydroxymethyl, nitro, formyl, hydroxyiminomethyl, alkoxy of 1 to 2 carbon atoms, methoxycarbonyl, atom hydrogen, halogen, or acyl having 2 to 3 carbon atoms, Z is hydrogen, hydroxyl or methyl, R is hydrogen or -OR, where R 1 is alkyl of 1 to 3 carbon atoms, alke C-3-alkynyl, C-3 alkynyl, 2-carbon haloalkyl, methoxymethyl, C 4 -cycloalkylalkyl or cyanoethyl, A is O or S, and B is C 1 -C 4 alkyl, alkenyl with 3 carbon atoms, cycloalkyl having 3 carbon atoms, phenyl or a group of the formula -WR ^, where W is an oxygen atom or sulfur, and R 1 is cycloalkyl of 3 to carbon atoms, fluorophenyl, alkyl of 1 to 4 carbon atoms, alkenyl of 3 to 4 carbon atoms, alkynyl of 3 to 4 carbon atoms, haloalkenyl of 4 carbon atoms, haloalkinyl of 4 carbon atoms, cycloalkyl C 1 -C 3 -alkyl, C 1 -C 3 alkyl substituted by halogen, cyano, methoxy, phenyl, C 3 alkenyloxy, haloalkoxy, phenoxy and / or henzyloxy, wherein R and Y cannot simultaneously be hydrogen it exhibits excellent fungicidal activity of plant pathogenic fungi which are resistant to benzimidazole, thiophane and / or cyclic imide fungicides. It is noteworthy that its fungicidal effect on benzimidazole, thiophanate and / or cyclic imidic fungicides (hereinafter referred to as "resistant molds" or "resistant strains") is considerably higher than for benzenzimidazole, thiophanate and / or cyclic imide fungicides (hereinafter referred to as " sensitive " or " sensitive strains ").

The aniline derivatives of formula I are fungicidally active on a wide variety of pathogenic fungi, such as: Podosphaera Leucotricha, Ventrurla inaequalis, Mycospharella pomi, Marssonina mail and Sclerotinia mail apples; Phyllactinia kakicola and Gloeosporium black-crowned cockatoo, Cladosporium carpophilum and Phomopsiia 8p. graminief. sp. hordei, Cercosporella herpotricholdes and Fusarium nivale in barley, Erysiphe graml-nis f. sp. thitici in the creeper, Sphaerotheca fuliginea and Cladosporium cucumerlnura in cucumbers, Cladosporium fulvum in tomatoes, Corynespora melongenae in Solanum melongena, Sphaerothecahumuli, Fusarium oxysporura f. sp. fragarise in strawberries, Botrytis alli in onion, Cercosporaapii in celery, Phaeoisariopsis griseola in beans, Erysiphe cichoracearum in tobacco, Diplocar-pon rosae in roses, Elsinoe fawcetti, Penicillium italicum, Penicillium digitatum and oranges, Botrytis einerea in cucumbers, Solanum melongena, tomatoes , strawberries, pepper, onion, lettuce, grapes, oranges, cyclamen, roses or hops, Sclerotinia sclerotiniura in cucumbers, Solanum melonge-na, pepper, lettuce, celery, beans, soybean, azuka bean, tomato or sunflower, Sclerotiniaeinerea peach or cherry , Mycosphaerella melonis cucumbers or melons and the like. Namely, the compounds of Formula I are highly effective in controlling resistant strains of these fungi.

The compounds of formula 1 are also fungicidally active on fungi sensitive to known fungicides as well as fungi to which these known fungicides are ineffective. Examples of these fungi are Pyridularis oryzae, Pseudoperonospora cubensls, Plasmopara viticola, Phytophthora infestane and the like.

The compounds of formula I are preferably of low toxicity and have a low adverse effect on mammals, 243487 4 'fish and the like. Also, they can be applied to the agricultural field without causing toxicity to agricultural crops.

The aniline derivatives of the formula I are prepared by one of the following methods, wherein process a) is also an object of the present invention.

Procedure a)

A compound of formula I can be prepared by reacting a compound of general formula XI

NH-Z (XI)

wherein X, Y, Z and R are as defined above, with a compound of formula XXI to R6 - c - β (m)

wherein A and B are as defined above and R 8 is a halogen atom or with a compound of formula IV B'-C-O-C-CIV where A is as defined above and B'is alkyl of 1 to 4 carbon atoms, alkenyl with 3 carbon atoms, cycloalkyl having 3 carbon atoms, or phenyl.

The reaction is conveniently carried out in the presence of an inert solvent (e.g., water, benzene, toluene, xylene, diethyl ether, tetrahydrofuran, dioxane, chloroform, chloroform, carbon tetrachloride, ethyl acetate, piridine, dimethylformamide or mixtures thereof). If desired, the reaction may be carried out in the presence of a base (e.g., pyridine, triethylamine, potassium hydroxide, Ν, β-diethylaniline) to obtain the compound of formula I in high yield. The reaction may be carried out at a temperature of from 0 to 150 ° C for up to 0 hours.

Procedure b) YZ a

The compound of formula (I) wherein Z is hydrogen and B is R '

X

a group of the formula -W5, a compound of the formula V ## STR5 ## wherein

R — f — N = C · A

, Y

wherein X, Y, R and A are as defined above with a compound of formula VI H-W-R 1 (V) (VI) wherein W and R 1 are as defined above.

The reaction is conveniently carried out in the absence or presence of an inert solvent (e.g., benzene, toluene, xylene, diethyl ether, tetrahydrofuran, dioxane, dimethylformamide, chloroform, carbon tetrachloride). If desired, the reaction may be carried out in the presence of a catalyst (e.g., triethylamine, Ν, Ν-diethylaniline, 1,4-diazabicyclo [2.2.2.3 octane]). The compound of formula I is thus prepared in high yield. The reaction may be carried out at 0 to 50 ° C for up to 10 hours. 5 243487 (VII)

The starting compound of formula V can be prepared by reacting a compound of formula VII

X nh2

Y wherein X, Y and R are as defined above and phosgene or thiophosgene.

The reaction is conveniently carried out in the presence of an inert solvent (for example benzene, toluene, xylene, ethyl acetate or mixtures thereof). The reaction may be carried out at a temperature of 50 ° C to the boiling point of the solvent for up to 10 hours.

Commonly used starting materials (II) are prepared, for example, by reduction of nitro-benzene derivatives of general formula (VIII)

X NOj (VIII) wherein X, Y and R are as defined above.

The reduction can be carried out in an inert solvent (e.g., water, methanol, ethanol, or mixtures thereof (by reaction with a reducing agent) such as sodium sulfide, sodium hydrogen sulfide) at 50 ° C to the solvent temperature for up to 12 hours.

The reduction can also be carried out in an aqueous organic or inorganic acid (e.g. acetic acid, hydrochloric acid or sulfuric acid) with a powdered metal (e.g., powdered iron, zinc or tin) at a temperature of from 50 ° C to 100 ° C for up to 12 hours.

The reduction can also be carried out by catalytic hydrogenation, for example with a catalyst (e.g., platinum oxide, palladium on carbon) in an organic solvent (e.g. ethanol, ethyl acetate) at atmospheric or slightly elevated pressure and at 0 to 60 ° C.

The nitrobenzene derivative of the formula VIII can be prepared by reacting the phenol of general formula IX

X

In (IX) wherein X and Y are as defined above with a compound of the formula wherein R is as defined above, and D is a leaving group (e.g., halogen, tosyloxy, mesyloxy).

The reaction may be carried out in a solvent (for example water, Ν, Ν-dimethylformamide, dimethylsulfoxide, tetrahydrofuran, dioxane, toluene, benzene, diethyl ether or mixtures thereof (with base), for example, sodium hydroxide, potassium carbonate, sodium hydride, N, N - diethylaniline, pyridine). For example, tetre-H-butylammonium bromide can be used as a catalyst. The reaction is carried out at 0 to 100 ° C for 12 hours. 243487 6

The phenol of formula IX can be prepared, for example, by reacting a compound of general formula X

Y

wherein Ϊ is as defined above with a compound of formula XI from '-C - RS (XI) II *

A where A 'is as defined above, R 8 is alkyl, alkenyl, haloalkyl, alkoxyalkyl, or a general formula - A "- R 2 wherein A" and R g are as defined above and Z' is a halogen atom.

The reaction can be carried out under the same conditions as described in process a).

The compound of formula X is a known compound and is described in J. Chem. Soe. 1945,663 (Y = -CH 3) and 1,896, 1,321 (Y = -OClty.

Procedure c);

The compound of formula I may also be prepared by reacting a compound of formula XII X, (XII)

wherein X, Y, R, A and B are as defined above with a compound of formula XIII Z "H7 (XIII) wherein Z is as defined above and Ry is a leaving group (for example, halogen, tosyloxysulfanyl, mesyloxy).

The reaction is conveniently carried out in the presence of an inert solvent (e.g., water, benzene, toluene, xylene, dimethylformamide, dimethylsulfoxide, dioxane, chloroform, and mixtures thereof). If desired, the reaction may be carried out in the presence of a base (e.g., triethylamine, sodium hydroxide, sodium hydride) and / or a catalyst (e.g., tetra-n-butylammonium bromide). The reaction is normally carried out at 0 to 150 ° C for up to 12 hours.

Typical examples of the preparation of compounds of formula I are given below: Example 1 Preparation of isopropyl N- (3-chloro-4-ethoxy-5-methoxycarbonylarainophenyl / carbamate / process a /)

Methyl N- (2-ethoxy-3-chloro-5-aminophenyl) carbamate (1.39) and Ν, Κ-diethylaniline ((/, 85 g) was dissolved in toluene (15 mL) and isopropyl chloroformate was added dropwise. The mixture was allowed to stand at room temperature for 12 hours, 7,243,487 was poured into ice water and extracted with ethyl acetate, and the extract was washed with water, magnesium sulfate, and concentrated and reduced pressure. The residue was purified by silica gel chromatography using a mixture of toluene and ethyl acetate as eluent to give iaopropyl N- (3-chloro-4-ethoxy-5-methoxycarbonylaminophenyl) carbamate (Compound No. 1.73). g) Yield 92.0%, mp 140 ° C-142 ° C Example 2 Preparation of 1-methyl-propenyl-N- (3-chloro-4-ethoxy-5-methoxycarbonylaminophenyl) carbaaate (procedure b).

Methyl N- (2-ethoxy-3-chloro-5-aainophenyl) carbanate (2.67 g) in toluene (20 mL) was added dropwise at 10-20 ° C to an ethyl acetate solution containing 10 g of phosgene. The resulting mixture was warmed in succession and, after heating for 30 minutes at reflux, the room temperature was cooled. The solvent was evaporated under reduced pressure to give 1- (2-ethoxy-3-chloro-5-iocyanatophenyl) carbaaate. The crude product thus obtained was added to a toluene solution (50 ml) containing triethylamine (1.0 g) and 3-buten-2-ol (0.79 g). The resulting mixture was not left to stand at room temperature for 12 hours, poured into ice water and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography using toluene / ethyl acetate as the eluent. There was thus obtained 1-ethyl-2-propenyl N- (3-chloro-4-ethoxy-5-methoxycarbonylamino-phenyl) -carbanate (Compound No. 3) (3.57 g). Yield 95.6%. nfj = 1.5383. Example 3 Preparation of isopropyl N-methyl-N- (3-nitro-4,5-diethoxyphenyl) carbaaate (procedure c /):

Isopropyl N- (3-nitro-4,5-diethoxyphenyl) carbamate (3.12 g) and iodomethane (4.30 g) were dissolved in tetrahydrofuran (10 mL). The solution was added dropwise to a tetrahydrofuran solution containing potassium hydroxide (1.68 g) and tetra-n-butylammonium bromide (1.0 g). After standing at room temperature for 12 hours, the reaction mixture was poured into ice water and extracted with toluene. The extract was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by chromatography on silica gel using toluene / ethyl acetate as the eluent. This gave isopropyl N-ethyl-N (nitro-4,5-diethoxyphenyl) carbamate (Compound No. 16) (2.92 g), yield 89.5%, 1.5075.

Further examples of compounds of the formula I according to the invention which can readily be prepared according to procedures aZ, b / or c / are given in Table 1. 243487 8

Compound No. Xi RZAB physical constants o- 7 ΟΊ t- p

P co ΙΛ

CM • - * Ί

IfX

CM 7 P £ ** £ M ·

CMP £

CM 7

CM

P

P ci

CM o σχ om · - σχ

AND

CM on - σχ il xo

CMO £ xo

CM A £ - ~ a

• rl »HO

II f * t * 31a_ and Q ~ and 8 8 8 ”at 8 i * i *

aT aT aT

CM OJ CM 8

I a

CM O- and t-8

I and on a ~ on 8

AND

CM ao

II r- aa

CM a *

CM 8

AND

aT

CM 8

I ΙΛ and he 8

I af

CM 8

I af

CM 8

AND

CM and 8

II a3 8

AND

O

CJ

I he a

I af 8

I a

CM 8

I aa 8 8 oooo on a 8. o a aaao Q 8 O o o o o uoaaaaaa

CM ao

II ao

CM a

OJ

O aia 8 oya '8 g 1 and 8 oo 9 243487

Compound δ. X 1 BZA B phyaical constants

(A σ K0 so

CM irs CM Qβ t as m 8

AND

* »Xj- P ♦ CMQ ·

P β P «ΓΠ

I Ή t-

X cn 8

AND

QO

O 7 0

O σ »trs irs ΙΛ

QO <n σ * os e * irs

KO <n

CM ií 00

CM OM · CM t · · CM - 4Λ |

* CM - t-

vO 00

tfS 00 + j irs • Cjn p β

NQ β

ITS cm aβ <M «β

(MP β lf

CM Q β

aT 8

I b- ®, 8 1

aT 8

I t * - “ín 8

I t * -

X f * Γ *

X m 8

AND

CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM cn m

CM as 8

I 35 8 oo í

ITS

X

CM 8 f ΙΛ

X

CM 8

IfS

X

CM 8

IX o X y X y X yoo * ooooooo ϋ oo

CM

O

X

AND

CM o

X

AND

X 8

CM

X

O

X

X θι o

X o

CM o x X 8 CM 8 | CM O OT | CM X 8 CM X 8 CM X 8 x »xco OOO o ™ 1 ti X oo 8 X 1 1 X t X 1 1 1 X 1 n

CM o

CM

X

CM 8 8

X

I 243487 10

CM »Cd O

Compound No. XY Η ZAB Physical Constants oo co t-

X * * H «k X • H e * Ex w ^ k, <-> XO-»» x x x x x x x x x x x X X X X X X X X X X X X X CM X <-k XXX k_X X k_ ^ vO XX 5 m Vk • k what <0 * cn CM o O Z-> Ό oo * (4 * k e. * CM X • k ^ »Vk m CM Vk>·>« k P * 0 fn Θ V "X") s O O * * * * * * * * * * * * * * * * * * * * * * * * * * k »- 00 xk Vk tr * Ok« k X Ό «k« X Ό r- * Vk Vk cl ΙΛ O CM - «i- CM cn VO« * VO «Vk« k Vk> k CM • k Vk Vk what Vk Γ I * "kk fr- σ Cl vs X- ^ '> n X» km XX 3 Η XX 3 | -1 XXXH cq CM o • kt ** w 2 VO CM o ø * * WO om ω O x-> and δ kao X «Vk v. • HXHO ·, Vk • rl Vk e-« o Vk Vk Vk et o P <r xn • Fk. 0 σ · X0 X — kx ~ k P what B »k-« * - * X s / k— · XX CO * - * kX t © CO v-> ΡΊ CM >> O Φ K0 oo m (¾ O 0 4rf ·· pj cn σ> KO Vk Vk (¾ m ~ σ »a»> o Ό a «ka> Vk >> Ό a * Vk 2 b 2 - cn

• H

• H c- x 1 * 0

• H

m c- 8

CM 8

M

CM ffl

-X

<M 8 ΙΛ

X

CM 8 b- oo. ts

CM CM CM Γ 8

ΡΊH), 7.11 (broad, 1H), 8.14 µl

X

CM 11 243487-333 03

P Λί

What Λ £ 3

• H β Φ

XO §

CO 7.12 (broad, 1H), 7.20 (d, cm 00)

AND

CM 33 j? 33 m 33

O β CO ♦ H 00κο * ί-ο *

-φ ZX-ai 33

p, r - O o M3 p, T CM T— ΓΗ ΓΗ o σ T3 ΓΗ px. ρ-χ with Z ~ X Ό CM CM t rl P. * p. (? 33 33 33 x_z * CM 00 A CO O «- CO o CO n ΓΗ ΓΗ · - P— O z — x A ·» a « -l a 5 5 5 5 5 5 5 5 o o o o 5 5 5 co co co co co co co co co co co z ζ χ XO Ό w> »33 33 33 33 33 ΓΗ 33 33 33 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1------ Honors CM, ζ-χ fti c- CM • H z- “x / —XP 33 O • o P y 3 o * 33 y XQ 33 33 • β PS - · - '3 <- m A '“-s P-» - P M5

A CM Qβ c- 33 m%

AND

A 33

CM 33

CM

About what

AND

A 33

CM 8-

I ΓΗ 33

O 33

O

I 33

O 33

O

II 33 o 3? *

A 33

CM

(A 33

CM

O

I 33

CM 8

AND

A 33

CM aoi

A 33

CM

O

33 33 33 and OQ o OO o OO OO 33 33 33 23 23 CM m -4- γη γη m

X ooo

Q

AND

rH

-F- γη <h 243487 12 í * - »33

(M Μ- Ι

33 m 33

CM and aCM -

AND

• H X0 X)

(O .Μ

O Οι

P

G <0

P 03

G

O ΛΙ

CQ 71

O

W

bO

31 33 31 M3 - - CA «cm σ» <-> * * and 'Φ. t-10

CM sn

Kw »cn 38

HIM

(O

0 CM

* 33 IA — «- · - 0)

<O e * m

I m ΙΛ 38

HO 31 f * 1

CM M>

IA n cn t *--o * t * - * 33 0 »-

CMQ

G aaa CM <M «- p * <í τΓ ΡΊ 1At- ”

(T> IA nc <3?

O • ha »5 - $ 58 co 2 h1 a38"

HO * P to Χ- »

rH

° CM go ni 3? * 8

I 33

A 33

CM 8

AND

øM

OI * 1 33 8

O y

"cm 33 33

OO a 8 ao

and it

aT 8

I and ^ 8 and a1g_o

I 33

A 33

CM

LA 33

CM a

CM 8

I a

CM 8

AND

IA a

CM 8

I ΓΑ cn a ca aaaa 8 8 8 8 OOOO ggggaaaaa a. 13 243487

Compound No. X Ϊ R ZA B physical constant

LO PO Ό a (0 oo what aa "aaaaa Λ4 xz m Xz- and PO aoa - PO O 1 O PO OJ β and O«> what about * ao * «. • kaa • H z — x vt -P e - CM and -P and M · 0) and Ό «- ZX and X0 aa Z *> and MO zx * —z ta and XZ X» x · 1 and XZ r- · 0- PO 1 and x from IA O PO o o o o o o o o o o o • o o o o o o o o o o o o o o o >> zX zx and zx z — xaaaoo · »o o aa Λ} aav aa IA Ό a— aa PO IA * »-» M5 O «- - - Ol Ol PO IA o ti Ι ak · * a • k V0 OO and Ή« k * az — XO PO aa zx zx IA, P0 PO σ · a PO PO PO PO PO PO PO PO PO PO PO PO PO PO PO PO PO PO PO PO PO PO PO PO PO PO PO PO PO PO PO PO O β · - SQ o PO a «.3« aaa HO aaa Ol • lJ 00 HO σ> oaa »- HO a • ka σ 'Ό z — x zx ta xo zx Ό σ4 <O aa Xz r- XZ 0- <om M · a and IA IA PO 1 o IA O o <0 Ol * M · • koaoa lA IA M * σ PO IA and r. 0- zx Ol Zx QJ <0 zx aaa 's and m-o and k oi O * 3 Θ aaaa * 58 aa «t oi? rH o O

κ 33

O

OJ aoo

OJ ao

OJ aoo

AND

OJ ao

OJ aoo

OJ aoa ™ oo

AND

and

Ol and 8

O oaai

CM 8 ia a

Ol ooia

OJ oo

I rl o

pO and 8

O

Q aoooa? aioooomaoooo §

AND

«3 * LA

L > O-CO M- '<vj- 243487 14 th ¢ 0

P

OT o xo * Ffl, and ffl -t and>

*> C-line

MOO rt εχ, w

o M- X 0) o M- 1 o OS XX *> »rl m X — cn X_X * t« k ΓΊ XX x_x with XXI with CM o cn z - «» · «ΙΛ o • goat-k • Z k t- «Ό« μ μ μ μ X X t- μ μ μ μ X X X μ μ μ t- t- B B B B B B B B B f * S • k *. m CM M * • k Ό CM CM a CM ~ ~ ~ O O O O O O k k O O O O O O z z z z z z z CM CM x ^ »* bb 'irs CM o • k« k 00 • kc * s M • • k «o Xk. oo • kc k • k • k • k <0 m B □ * us XX ”to M- n Z — to. χ-k. Om «Ζ * om zk ř 4« «4 4 k om om c c c c c c c c c <- ♦ XX what HXX 1 wo IfS ω om CM • k tfs SO 23Q <* s CM o o o O «k z. a« o X * X k Os aa irs Vk HO oo ^ B • kr * k • k X z - 1 HU «» » - k to k s s <O k_Z I CM o • k 00 k • k <k trs Os k * >> • trs CM xx • k ø * ζ-χ. 00 IfS fi r- / Z ^ M axis P 1¾ OOX σ 3 • k XB t * CM O * s «, XO <MO a> • k * - s * r * s 1 í s * s • M · ♦ - (4 and PXX ™)

CM

X o

aT

tfS

X

CM oo §

I os' X- X 8 CM r4 XOO CM XX 0—0 i

X

CM trs

X

CM aT1 8

About oxoooo O r- trs irs

XXX irs

X

CM

IfS

X

CM 8

X 8

O

AND

CM §

I cm cn

S ITS trs 15 243487

Compound No. X ϊ HZAB Physical Constants »*» »X ir • H x • rt 0X r- v. XO. X z'-. '>»Wj'>> X z — x >>r> X z ~ x '> s CO X CO X Λ1 x—' Λ4 co X 4d r- co X -M -· OJ OJ OJ OJ r r-----------------------r r r r r r r co co co co • X c 'b * o o o Q o o o o o o O O O O O O O O (((((((((((((( X Ό O m ir OJ CO CO OJ OJ Ή Ή Ή Ή Ή Ή Ή CO CO CO CO CO <»T-- X Oc Lf z — X. xo XT— «XX« X r - ox «X r -« X «XXX - from · OJ 01 r? O-r- co 0 cn O CO. O «X <x • X «X r. • rl 0-« X OJ '5 0- ΓΩ _z ~> e CO z — x, -. z ~ x XC X x ZZ ~ XZ — x Ό • x co X Γ — 1 XXX '1 — t XX OJ OJ r4 XXM · P ~ t 0 x WO ΓΊ Ol “X what a ΡΊ T ~ - mw 0« - t OJ ζ '-' χ and a 0 y-xx and Lí · X · · «« X X X X X X X X X X • X X X SX r 0 X X XX OJ J3 <- R 0 • x • X CO <X v X XQ v Ό P & X j j 6 ja P P χ X X X X X X X X X X X X X X X <0 cO m 0 O & cO M * 0 «X '>> 0 OJ 0« X m «. trc c o o «X • X CO p t m 00 S ~ χ zid z * S p ^ xr · 0 z—-,« X! A p <m CO X ~ X 0 «XX pij« X <x X c- OJ Q «X • XXX OJ Q Ό OO X« - 0 Ί 01 fU * ir \ t

X 8

X

OJ

O

AND

O

X

AT

O

I c- xm {"-

X moo

I tr;

OJ

O o

AND

OJ o

X

OJ ooioooo

X

I 243487 β (0

P (0 t ΊΒ ΊΒ 44 • Η Η £ tab β <υ

XJ 3

O r ~ lc / 5 16

£ aa * sa <aa ca aa CM m n- «» o «LA PP ·» 0 t * f σ * «·. . »Ζ B A B · · · ·-----............... M A A tA tA z z z z z z z * * * * * * * * * * * * <a A f- co m z-> S Ό KO m Z ~ 'z — sz—. r — 1 a <A rd aaa Š8 mo,. IA ω QaS A CM · “HO« «CM CA« _ HO · «co sS * a <c lA 1 - O to * “" LA IA n "t o o o p o - o -> o p o o c o o c a c a>> 2 CA β 2» - ^ 1 I a

CM oo

I and ca σΑ «a <0 · κχ> Ο θ a <η ο «ο03 * χ-ζ (Ο

"Σ-C- ο (Α ια ο | 8Η Ο ΙΑ

(M 8

O r- CM

M3 vX) <O a

CM 8 a

CM tn ο * - σ * t - ΙΑ · »· t - <α t * ·

ζ> z *. SQ aa - γα cm σ σα oo <a <α a / η ι - ΙΑ aa aiA η - ο Νΰ 00 νθ (Q CM Q, β

And a

CM

And a

CM

(A

CM ao

II ao

oT

(A o aw oa? 1 o

AND

CM

O ai

CM §

I IA 0

O 17 243487

X

VO

Compound δ. X Ϊ R ZA B physical constant

CM b "> b-as 8

I lf as

CM

O and? 1 o

AND

CM

O as i b- vo • x xx ~>. > X w as sú sú sú sú as as as as as as as as CM as as as CM CM CM CM CM CM CM <~ χ r-— — — — — — — — — — — — — — — s s s s s s s s s s s s M · · · - σ o sO (A m • z ~ «. *>» Ό 00 co σ CM b- co »k Ό · - -« as as CM CM after po as and rH X o A A A A A A A A a a a a a a a a a a a a a a a a a a)) j J3 • k O ♦> b-O o OOO <O '-rb— e-' • O *** O CM «« k * What is CO CO X — k · A A A b b b b b b b b b b b b b b b b b b b b X 5 5 5 5 5 5 5 5 5 5 , 1H), 7.12 (broad b ~ as 8)

AND

lA as

CM 8

AND

aT what δ f trs as

CM 8

I §

aT otb »as 8

I u

CM 8

I r- as 8

I as

and it

S o

aT 8 o ™ ss

I as š ·

CM as cø1 as i 8 co

AND

IA as

CM 8

AND

O\

CM CO b 'b- b- as co 8

AND

lA as

CM 8 § as

AND

CM

O as b- 243487 18 ΙΑ • fr *

SlouSenina δ. X ϊ 8 2 A Β physical constants

IA <4 oo

IA o ø * σ \ t

M> Γ- CM σχ <n CO ΙΑ M> 0 aa | 7 LA A 28 · “ M >>>>>>> * p p p p p p p p p p p p p p p p p IA IA IA IA • OO O. • OOO • o OP r-4 r · 1 r4 PH rH rH σ «P« IA X0 X 44 44 «44 44 44 • a -« * P m (0 «P« 3 (0 CO *) P and CM 6.60 (Wide, 1H), 7.30 (Si ·

aT ΡΊ 8

AND

aT 8

I 2 * ^ 8

I af aT8 8

IA

US

CM 8 I ·

IA

US

CM 8

I a

CM 8

AND

lA a

CM 8

I 8 2 &

About us a

rH H

OO and * o $ 3? * 8

I lil o aT a8 8 aT *

O

S o aT * oo

I a fi? O

CM and 8

I and af 8 and '' o

aT

O

CM and 8

AND

aT

O

íS o

CM and 8

I and O. lil by 3? * 8

I aaaa 8 8 8 8 on OO ooaaoog

P— -

What is what

(AND

WHAT

VO and 19 243487

Compound δ. X ϊ R ZA Β physical constant

* Q Q Q Q Q Q Q Q Q Q Q Q Q Q Q Q Q Q Q Q Q Q * * Q Q Q Q Q CO CM σ CM CM σ ' · Ό Ό • • ·>...... O ΡΊ what OO> · O CM * · «k ·> Sk lA • k O CM σ 'σ' X — κ <·> Sc Sk z * x • * O maa e- o rM am LA CM CM CM rQ CMQQQ * * IA lA LA COQ (4 1 SP *> »1 >> t- ·. 23 • k • k • H o ROP CM PP CM w ~ ** Ao P <4 X0 and Ex o CO • H - H • H and>> IA IA LA. O • OO • • k • k CM Ό • • k d rd P r 1 1 — 1 P σ σ σ 'm t Ό P CM AI and Ai Λί • - P - p «- P * k O 0 • • k 0] P 0) m P C5 ť fi a · - Ό P 3 CM 1 * 1 35 ΙΑ 35

<M 35

CM 8

(AND

35 'CM 8 - 35 - <35> a 8 8 35 · §

CM 35 8 35

CM 8

O

II «

O

3SW 8 35 «·

CM 35 8 35

O

CM 35 8,

LA 35 CM 8

CM 35

Á 35 c 35 35 35 35 35 35 35 35 35

aT 8 ao

aT 8

IA 35

CM ΓΊ 35

° CM

X

O

CM 35 8 1 35

O

I LA LA LA LA LA LA (*> aaaaaaaaa CM CM CM CM CM CM CM CM 8 8 OO 8 8 8 8 OO 8 OOOOOOO o O OO ooooooaaaaaaa 3 3 3 aaa 3 aa

8,535

AND

§ 535

I ί- α) co co σ \ t

CM o mc \ t

φ IA σ c σ c — σ σ> 3.71 (s, 3H), 6.55 (broad 1 H), 7.05 (broad; 1H), 7.15 243487 20 X) ai>&& »

, M

O 0 >> ρ tí ο §

rM K> 0!

P to it

> O 3

O rd cn uf1 8

AND

aP ο

II and ο

aT 8 and ο.

Co cm cm cm cm C C C C C C C · · · · · · · cm cm cm cm 0 0 0 · · · · · · · · · SSΑ σ í - CM SS t- o & E- <M m CM <M 1 cn irs lA lA <A · »« * * * LA 00 LA LA IA P 0 * - A CM A «-A • - A aca P β 0 and · af

AND

I 18

• O ΙΑ “k, 8

LA a

CM 8

AND

lA ° 8a and ff

AND

IA ', 8

AND

aP

LA O aP8 "to $

aT 6 8

I s g g T «á a 7 7 7 7 and 7

aT aT aT

and

wP a

aT σ> o

CM

O <no * - * <* »*» »* Aa - * t -

R CM *

* »O« «» «* - * - * * · · - S- * $ $ m m 4

sa CM yoo lA 9 h * LA • k · P * ►> «k * 2 * MO« k * «* P: '<* »Of c- and P LA t> lA o CM and> o ·> • o o o <* k «k P Ό P and 4 J4 -A • CM * mT what. PZ · k P sz P

lA a

CM - ø * a am m! - 8 ao

aP

O and? 1 8

CM sao

aP 8

AND

aT

O

I a ^ aTV * i

LA U>

OO 21 243487 I t> 1 * 1

Compound No. XY 3 ZAB physical constants o

AAA Η Α X z- *. Z Z * / 'AS Zx / - k zx χο ρ ~ XXX Λ5 XXX PA CM »- o PA CM Α r. CM Z ~ k P and AA • HAAA σ> X what σ1 Ό xo o * CO ω Α Α- X_Z •> -_ of LA0 LA Α CM IA CM CM oo-Ό Ό «« «« «« «CO CO CO CO CO CO - - - - - - - <- r- A “« - pa - # Ρ ~ ο ·· ζ— ο AAAA o CM CM o σ · AA Α Α pa? co p- pa PA »- Z '^ £ £ PA CM CM CM CM CM CM CM r Q Q Q Q Q Q Q Q Q Q Q Q Q Q Q CM 0 Α ΙΑ r. Ň ň A A A A Q A ň ň 0 ň ň ň OA ň OA ň ň ň ň Η Η Η OA OA OA OA OA α α α α α α OA OA OA OA OA Α— <* · ». C0 «5 X 00 0 IAΑ IA o L0 L0 Α ΙΑ CO LA o OAAAAA e- σ0 Α Α 00 CM C - CO O / -s CO L0 LA p- P * pt CM Τ- L0 Α +> σ - QSAAA - X - Q CM P Q Q CM O j * g | A Α Α ο τ) • QG x A- pa ia pa GGGGG x CM Μ- \ t

X nooi

X

1 xoo

I 33 oo

I 33

O o

I 33 8 x

CM ooi

X

CM

O

O 4!

23 XX 23 23 o-23 23 G ΡΑ X <Μ X (Μ XXX ο X X ο ο (Μ Μ II X ((((((((((((((((((CM CM CM CM CM CM CM CM CM CM ο ο ο ο ο ο Article 23

O

23 23 r * 1 23

O

I 23

O 4 23

O

AND

PA ΠΊ

X

O

Pa Ι Ι Ι Ι LA Ι Ι LA LA LA LA XXX XXX XX XX XX XX XX XX XX XX XX XX α α α α α α α α α α α § XX § XX § § § X § X § § §

48 II 48 243 48 >> ρ 48 48 48 48 48 48 48 48 48 48 48 48 48 48 48 48 48 48 48

CO + »

XJ co t; β ω> υ

O ώ 22

* 1 Z— K • H and z_% z— XO he and he · O — Z P P * r. On a * w W Γ. «- ο o ι r> CM AO o Ό ·. CM KO ooooo «-» oooo CM * ± ø-CM O «» OO o A on Ό o- o 00 O ·. A »- r - ·Α · - o IT \ t <M ΟΊ Z — vz. z ~ xt * »A V» On CM o r- r — 1 aaa σ> IA IA IA A ΙΑ wo <0 CM T— «. 1 1 1 1 n M rt «» SA 1 v - τ- t - EH O w - a on CM A o. * O * a on * J- * - r- A to O 'T— r— v> - C OOO »» »» »» »» • • • • • • • • • ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ P · «O O β β β β β r r β β P P P P P

fC • H Ή AA r * c * "o- aaaaaa CM CM on on on o o QOOOOO

IIIIII o- aaoao tl o ni aa ni aoo IA ooo CM CM and CM CM 0 aa CM aaaoo Q ooooooooor ř ti..

I ΟΊ

LA Ά IA LA LA LA aaaaaa OJ CM CM CM CM CMOOOOOOOOOOOO oo O o O o C o o o 3 aaa aaaaaaa co σ 'o

CM

OJ

CM

CM <WO 00 ο a a a a a a a a a a

CM 4.05 (q, 2H), 7.2-5 (broad • H • H • IA * r * c * on aaaaa CM on on o oooo o ooo

I tt II ia a

CM 8 t

LA a

CM

O

AND

A LA LA LA LA CM CM CM CM CM CM o o o o o o o itttt

LA a

CM

O a

CM

O

AND

r — I

O on aooo 8 O on a 8 O w <r> and he and 8 O o Q oiaoo § aagg

Xf- (A kO

CM From OJ

CO CT CM (M CM

Pokr. tab. 23 243487 xo Λ4 «Η s

LTS trs

Lf o σ \ t

ooo

I oop

P oo

<M

CM

AND

CM

P

About what trs trs uo

"řP tr tr • M ·

IM ·

P

PM · O ””

lf I 00 trs trs

«- CM oo \ t

CM

LCX after a

CM 8

AND

II tuft tuft tuft

About CM oo ooo r- cb po

M ro ito <j \ t

£ J moom trs Ό trs trs

what about QH O o <xf

PO as oo

I ♦ rC • H • HH • H UO - - t - trs * * - LfS r- baaa PO aaaaa CM 1 * 0 CO PO and CM co a CM PO PO ϋ o O OOQO oo OOOO what co to OOO co

I a

CM

O o

AND

PO ao

AND

PO o »

PO ao

AND

CM and II o. And nio o

PO aoaoo

I after aoaoo

I aaaaaaaaaaa »'1a i' iaaa 8 U o 8 oo 8 oooooooooo 8 ooooaoooo CO oooooo O oooo o o. ooooooooo 3 aaaaa 3 and £ q 3 aaaaaaa 3 * aaaaaa · aaao after cm after po Μ-

PO trs <ot * · AFTER CO

CM xt PO -Φ xj- 243487 24

Compound No. XYH 2 AB physical constant

• and o o «for C- Ό z - ·. * Ό 1 Z ~ a. d * z — a Za n X r * XX r ~ o IA o IA IA IA IA IA IA IA 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 oo oo oo oo O Ad-am O CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM <* and co »- X • and X r4 X X0 XX σ C9 IA O - WQ« and CM <*> a_x o CM 1 »IA Cm X and δ 3 Cm 1 ♦ H ~ <D * ►> AO oo Ή M5 0) t- xn >> p 01 xn *> t- «« r CM · X vx £ t- • rl o X s_z a, ^ z £ f CT \ t ~ o a-«fr fr fr fr fr fr m m m m m» »» »» »» »» »P P P P P P P P P P P P P ^ PXM • • CM V0 m X 1 ΡΊ CM PPP n

X 8

CM

X

U í x xo

X oo

I ř *

X / *> r- x / n 8

IA

X

CM

O

I x

CM

X

CM

X

CM 8

I os

CM 8

AND

rM

O

X 8

O y

AND

CM

O

X

CM

O

X

I x * "1 w

aT wo

I-SOCH-, -CH-, -OC-H, H-O-O-JUC1) -

o μ-ια IA 25 243407

SiouSenins δ. X Η Η ZA Β physical constants ο ΙΑ

Cl ΡCJ Η Ή Η ρ ρ ρ

X x * x

Cl

O

AND <*>

X ot h-

X ί * Ί 8 h- χ mo

O

I f *

X what

X

CJ 8

AND

X

CJ

X ci

X fy

lA

X cy

X fy 8

X o

CM

X o

AND

X about her

Cl

X o

AND

X

Cl. m

X o

I re

X u

CO \ t

II <yom

Three

X fy o ω i

X cy about it

Q

I 5 cos oi .n

IA

lA:

IA IA lA

WHAT

LA

IA

the

X

Cl 8

AND

X

Cl 8

IA

X

Cl

X

Cl

Cl o

X

I ΓΊ

X oo

Cl

X o

I ΓΊ

X oo

Cl

X o

AND

Cl o

X

AND

Cl o

XO-Cl kO to re <0 164 -NO--CH-OCH, -OC, H, -CH, COOCH, -OC, H "<i) 243467 26

Compound No. XY 8 ZAB physical constant

AND

<M

<P sf * m 8

I - ° 5n 8 • H • «• H * - * Ή><n £ Ϊ “Jn” "- 8 1 8 1 8 1 8 8 1 8 t *« m 8

IA

W

CM 8

AND

IA

W

CM 8 9

IA a

CM 8

AND

iA a

CM 8

AND

I o <* »O co» * σχ. £ λ a λ ř λ λ λ λ λ λ λ λ λ λ λ λ λ λ λ λ λ λ λ λ λ λ λ * - * »and * * - * J <* «- (« -

<A a-g-M «theatrical« «'* O», »O *« and ό · a <o M> * - * (AM <M * - * <n

aT

O

I 3? 8

and it

I a ™ ot

aP

CM ao

I ΓΊ 0

aT

O

AND

CM

9 tg 1 o * tg 9

CM oo tg a

IIL * fev 4

lA in M> M3 σχ in

IA “K. 8

O 8

AND

lA a

CM 8

I * τΓ 8 af

O 1 c * tg

AND

IA a

CM a

CM

IA a

CM 8

AND

IA a

CM 8

AND

IA «« w 8

I af

O

CM

O

IA a

CM

O

About what

I § o

I 9

Ol

CM *><

aT

In the practical use of the compounds of general formula (I) as fungicides, they are to be applied as such or in the form of saccharides, seedstocks, oil-based concentrates, tablets, granules, other granules, aeroaol! or liquid preparations. These compositions and compositions can be formulated to produce at least one compound of general formula I and solid or liquid carriers or carriers or diluents or diluents and / or adherent agents (e.g., surfactant, adhesives, dispersing agents, or stabilizers) that have been abandoned. rosptyl or other active ingredient. Examples of solid worn! or diluents are natural naterlles of vegetable origin (eg nouka, streaked tobacco stalks, soybean strips, walnut sheaths, scrambled sausage, chipped sawdust, bran, streaked Mra, cellulosic strips, extracts extracted by nickel) fibrous naterials (eg paper, corrugated board, old rags) synthetic plastic strips, clays (for example kaolin, bentonlt, fuller's earth), talc, other inorganic naterials (eg pyrophyll, sericlt, pensa, plated sulfur, activated carbon) and chenical fertilizers (for example, anion sulphate, sodium phosphate, anionic nitrate, urea, anionic chloride). Example of liquid carrier! or diluents are water, alcohols (e.g., ethanol, ethanol), ketones (e.g., acetone, non-ethyl ethyl ketone), ethers (e.g., diethyl ether, dioxane, celols, tetrahydrofuran), aromatic hydrocarbons (e.g., bensene, toluene, xylene, ethyl * naphthalene), aliphatic hydrocarbons (e.g., benzene, kerosene), esters, nitriles, alcohols (e.g., dinethylforneside, dinethylacetanide) - halogenated hydrocarbons (e.g., dichloroethane, carbon tetrachloride), and the like. Examples of surfactants are alkyl esters of sulfuric acid, alkylsulfonates, alkylarylsulfonates, polyethylene glycol ethers, esters polyalcohol! and so on. Examples of adhesive compositions include dispersing agents, gelatin, starch, carboxethyl ethylcell, arabic gun, alginic acid, lignin, bentonlt, nelas, polyvinyl alcohol, turpentine agar. As stabilizers, PAP (sis acidic isopropylphosphite), trisulfophosphate (TCP), toluene oil, epoxidized oil, various surfactants, various acid acids and their esters, etc., can be used. 1 to 95% w / w, preferably 2.0 to 80% w / w. When using the compound of formula (I), it is generally applied in amounts of 20 to> 000 g per hectare.

If applied only to the phytopathogenic fungus, which is stent, then the compounds of general formula I can be used sanostatically.

Thereafter, if the sensitive senses are present together with the fountains, then benzinidazole, thiophane and / or cyclic iaide-type fungicides or fungicides of the benzinidazole, thiophane and / or cyclic iaid type are used alternatively. However, in either alternate or combined use, each active ingredient may be used as either or both of the zenides of the medium. In the case of the co-utilized use of the fanatic poair of the formula I compound and the fungicide! a benzinidazole, thiophane and / or cyclic iaid type of from about 1: 0.1 to 1 s 10.0.

Typical fungicide examples! the type of benzinidazole, thiophane and cyclic iaide are shown in Table 2. 243487 28

Table

Sloudeninfi 1 Structure of Mdiev A C 1 -C 4 -haloalkyl-3'-acetyl-1- (butylcarbamoyl) -benzolaldaaol-2-yl * carbaadt CONHC 4 Hg / n B ooo H 2- (4-thlaaolyl) -benaialdaaol C — NHC00CH3 H methyl benzyldecol-2-ylcarbeedt D oxH 2 - (2-furyl) benzaldehyde with 1,2-bi (3-methoxycarbonyl-2-thio-B 5 ® -MeOOOC 8 C 8 HOMHQ000H, 1 s ureldo) bensea T8 ^ xHHCMBQOOC ^ 1,2-bi (3-ethoxycarbonyl-2-thio-Caureuido) benzene Τ 00 * sas 0 ^ x ^ XHCMHCOOCH, 2- (O, S-dimethylphosphoryl inol) -1-oc (3'-nonboxycarbonyl-2'-thioureido) XMHř - S - CH, »OCHjS«, NBOIUCOOCH, benzene H 2- (0,0-diaethylthiofoaforylenino) - ΓΓ-1- (3'-ethoxycarbonyl-2 MBP - 0 - CH, reido) benzene (OCH3 29 243487)

Pokr. tab. 2

Compound

Structure Title

COOC2H £

Cl o CH 3 N- (3 *, 5'-dichlorophenyl) -1,2-dimethylcyclopropane-1,2-dicarboximide 3- (3 ', 5'-dichlorophenyl) -1-isopropylcarbamoylimidazolidine-2,4- 3- (3 ', 5'-dichlorophenyl) -5-methyl-5-vinyloxazolidine-2,4-dione ethyl (RS) -3- (3', 5'-dichlorophenyl) -5-methyl-dione dione 2,4-dioxooxazolidine-5-carboxylate

In addition to the compounds of formula 1, they can also be used with other fungicides, herbicides, insecticides, acavicides and fertilizers, etc.

When the compounds of the formula I are used as fungicides, they can be applied in amounts of 0.02 to 1 kg per hectare. However, this amount may vary depending upon the application form, application time, application method, site of application, disease, and the like, and is therefore not limited to these respective amounts. Some practical embodiments of the fungicidal composition of the invention are set forth in the following examples wherein% and parts are by weight. Example Formulation 1

Two parts of Compound No. 1, 88 parts of clay and 10 parts of talc are sprayed perfectly and mixed together. A dust containing 2% of the active ingredient is obtained. Formulation Example 2 30 parts of Compound # 2, 49 parts of diatomaceous earth, 20 parts of white carbon, 3 parts of sodium lauryl sulfate as wetting agent, and 2 parts of calcium ligninsulfonate as dispersing agent are mixed and sprayed. This gives a wettable powder containing 30% of the active ingredient. Add Formulation 3 50 parts of Compound No. 3, 45 parts of diatomaceous earth, 2.5 parts of alkylbenzene.

Calcium as a wetting agent, and 2.5 parts of calcium lignin sulphonate as a dispersing agent are mixed and sprayed. A wettable composition containing 50% of the active ingredient is obtained. Formulation Example 5 1 part of Compound No. 1.1 part of Compound I, 88 parts of clay and 10 parts of talc were sprayed and mixed. This gives a dust containing 2% of the active ingredient. Formulation Example 6 20 parts of Compound No. 36, 10 parts of Compound J, 45 parts of diatomaceous earth, 20 parts of white carbon, 3 parts of sodium lauryl sulfate as wetting agent, and 2 parts of lignin sulphonate soaked as diepers were mixed and sprayed. A wettable powder containing 30% of the active ingredient is obtained. Formulation Example 7 10 parts of Compound No. 1, 40 parts of Compound A, 45 parts of diatomaceous earth, 2.5 parts of calcium alkylbenzenesulfonate as wetting agent, and 2.5 parts of calcium ligninsulfonate as a disintegrant are mixed and sprayed. Wettable trays containing 50% of the active ingredient are obtained.

Typical assays indicating excellent fungicidal activity of the compounds of formula I are listed below. The compounds used for comparison are as follows:

Compounds

Comment

Swep

Cl

NHCOCH3

Cl commercial available herbicide

Chlorpropham

Cl p- '

NHCOCH CH 3 CH 3 commercially available herbicide

Barban

Cl

O «

commercially available herbicide 31 243487

Compounds

Cepe

O

I NHCCH 2 CH 2 Cl

Cl

Propane

Notes commercially available herbicide

commercially available herbicide

Chlorbufaa

Thiophanate-ethyl commercially available herbicide available commercially

Carbendazin

With NHCNHCOOCH, NHCNHCOOCH-, commercially available fungicide commercially availableFungicide NHCOOCH3 Example

Protective harness test for powdery mildew powdery mildew (Sphaerothea fuliginea).

90-liter pots are filled with written soil and seeded with cucumber seeds (var. Sagaaihanjiro). The cultivation is carried out in a greenhouse for 8 days. Once the first pair of leaves appears, an emulsifiable concentrate or wettable powder diluted with water is applied by spraying in an amount of 10 µl per pot. Then the seedlings are inoculated by spraying a suspensor of a sensitive and resistant strain of Sphaerotheca fuliginea. Further cultivation takes place in the village. After 10 days, the infection stage of the plants is evaluated. The degree of damage is determined as follows and the results are summarized in Table 3.

Evaluated sheets are measured and percentages of the infected area are calculated. The rating is graded as a disease index by 0, 0.5, 1, 2, 4:

Disease index

Percentage of infected area 0 0.5 1 without infection infected area infected area less than 20% 243487 32

Disease index

Percentage of infected area 2 infected area less than 50% 4, infected area greater than 50% The severity of the disease is calculated according to the following equation: Seriousness% * -1 WAafltt QBMaWSffitZ Λ / POfat U. x, 004x / total number of evaluated sheets /

The value of prevention is calculated according to the following equation: prevention value% = »> 00 - / ΧόΖΙΜ, Β ^ VMftg.Saftfti V. ^ * 9tWW« fchm & zigb / -x, 00 / severity of disease in untreated pots / Table 3 Compound No. Active Ingredient Concentration (ppm) Value Prevention Inoculation Re-Slurrying (%) Value Initiation Prevention Sensitized (») 2 200 100 0 5 200 100 0 7 200 100 0 8 200 100 0 11 200 100 0 35 200 100 0 38 200 100 0 Swep 200 0 0 Chlorpropham 200 0 0 Barban 200 25 0 CEPC 200 0 0 Propham 200 0 0 Chlorbufam 200 0 0 Benomyl 200 0 100 Thiophanatemethyl 200 0 100 Carbendazim 200 0 100 From the results summarized in Table 3, the compounds I according to the invention show a preventive effect on the strain resistant but have no preventive effect on the susceptible strain tested. In contrast, commercially available known fungicides such as Benomyl, Thiophanate-methyl and Carbendazim have an effect on the susceptible strain but have no effect on the strain resistant. Other compounds tested structurally similar to Compounds I show no fungicidal effect on the strain-sensitive strain. Example 2

Preventive effect on cercospor. beet (Cerospela beticola).

90 ml pots are filled with sandy soil and seeded with sugar-sugar seeds (var. Detroit dark red). The cultivation is carried out in a greenhouse for 20 days. A water-diluted emulsifiable concentrate or a wettable powder solution of> 0 ml per pot is sprayed onto the seedlings. Then, the seedlings are inoculated by spraying a spore suspension of a resistant sensitive Cercospora beticola strain. The pots are covered with polyvinyl chloride film 33 243487 so as to increase moisture and cultivate for 10 days in a greenhouse. The degree of damage is as described in Example 1. The results are summarized in Table 4.

Table 4

Compound No. Concentration of active ingredient (ppm) Value of prevention by inoculation with an alternative strain (36) Value of vaccination by sensitive name (56) 1 500 100 0 2 500 100 0 3 500 100 0 7 500 100 0 16 500 100 0 30 500 100 0 36 500 100 0 43 500 100 0 44 500 100 0 Swep 200 0 0 Chlorpropham 200 0 0 Barban 200 34 0 CSFC 200 0 0 Propham 200 0 0 Chlorbufam 200 0 0 Benomyl 200 0 100 Thiophanatemethyl 200 0 100 Carbendazim 200 0 100 From the results summarized in It can be seen from Table 4 that the compounds I of the invention exhibit a remarkable preventive effect on the strain resistant, but do not exhibit the preventive effect of the susceptible strain tested. In contrast to the commercially available known fungicides such as Benomyl, Thiophanate-methyl and Carbendazim, they exhibit a noticeable control effect on the strain sensitive, non-responsive to the strain. Other compounds tested, structurally similar to compounds 1, do not challenge the fungicidal effect on susceptible strain and strain. Example 3

Preventive effect on pear scab (Venturia nashicola).

The 90 ml plastic pots are filled with sandy soil and seeded in them (bo. Chojuro). The cultivation is carried out in a greenhouse for 20 days. For the obtained seedlings, they test the test compounds by spraying 10 ml of a dilute aqueous solution of an emulsifiable concentrate or wettable powder on a pot. Inoculation of the spore spray with a resistant and sensitive Venturia nashicola strain is then performed. The plants obtained are placed in high humidity for 3 days at 20 ° C and then irradiated at 20 ° C with a fluorescent lamp for 20 days. The degree of damage is determined in the same manner as in Experiment 1 and the results are summarized in Table 5. 243487 34

Table 5

Compound No.

Value of inoculation by sensitive strain (%)

Active Ingredient Concentration (ppm)

Prevalence value with incrementalresistance (%) 1 500 100 0 2 500, 00 0 7 500 100 0 38 500 100 0 42 500 100 0

Benomyl 200

It can be seen from the results summarized in Table 5 that the compounds (I) of the invention exhibit an effective preventive effect on the resistant strain, but have no prevaent effect on the susceptible strain. In contrast, the commercially available known fungicides such as Benomyl and Thiophana-te-methyl show a marked control effect on the susceptible strain and no strain resistant. Example 4

Preventive effect on peanut spots (Cercospora arachidicola).

90 ml plastic pots are filled with sandy soil and seeded with araaid seeds (var. Chiba hanryusei). The cultivation is carried out in a greenhouse for 14 days. To obtain seedlings, the test compound is applied by spraying an aqueous solution of an emulsifiable concentrate or wettable powder in an amount of 10 ml per pot. Then the seedlings are inoculated by spraying a spore suspension of a resistant and sensitive strain of Cercospora arachidicola. The plants are then covered with polyvinylchloride foil to increase moisture and cultured for 10 days in a greenhouse. The degree of damage is determined in the same manner as described in Example 1. The results are summarized in Table 6.

Table 6

Compound No. Active Ingredient Concentration (ppm) Precautionary Values for Inoculation with Re-Resistant Strain (56) Precautionary Values for Inoculation with Sensitive Strain (56) 2 500, 00 0 Benomyl 200 0 100 Thiophanatemethyl 200 0 100 The results summarized in Table 6 show that whereas the compounds of the formula I according to the invention show an excellent preventive effect on the strain resistant but have no preventive effect on the tested susceptible strain. The difference, commercially available known fungicides such as Benomyl and Thiophanatemethyl, show a noticeable control effect on the susceptible strain, but have no effect on the strain resistant. 35 243487 Example 5

Preventive effect on gray mold cucumber (Botrytis ciaerea).

90 ml plastic pots are filled with sandy soil and seeded with seeds (var. Sagani-hanjiro). The cultivation is carried out in a greenhouse for 8 days by obtaining a seed pot with the first two leaves. The plants are then sprayed with the test compound in the form of an aqueous dilute solution of an emulsifiable concentrate or wettable powder in an amount of 10 ml per pot. After air-drying, the seedlings are inoculated with my-celia discs (5 mm diameter) of the resistant strain or citrate strain Botrytis cinerea so that they are placed on the leaf surface. After infection of the plants, incubation is carried out for 3 days at high humidity and 20 ° C, after which the severity of the disease is evaluated. The degree of damage is determined in the same manner as described in Example 1. The results are summarized in Table 7

Table 7

Compound No. Concentration Active Prevention Value Component Prevention Value (ppm) Inoculation Inoculation with Sensitive Resistant Strain (%) Strain (%) 1,500 100 0 2,500 100 0 3,500 100 0 4,500 100 0 5,500 100 0 6,500,100 0 7 500 100 0 8 500 100 0 9 500 100 0 10 500 100 0 11 500 100 0 12 500 100 0 13 500 100 0 14 500 100 0 15 500 100 0, 6 500 100 0 17 500 100 0 18 500 100 0 19 500 100 0 20 500 100 0 21 500 100 0 22 500 100 0 23 500 100 0 24 500 100 0 25 500 100 0 26 500 100 0 27 500 100 0 28 500 100 0 29 500 100 0 30 500 100 0 31 500 100 0 32 500 100 0 33 500 100 0 34 500 100 0 35 500 100 0 243487 36

The value of prevention The value of prevention when inoculating re-vaccination sensitive · kaenen (54) kaenen (54)

Pokr. tab. 7

Compound No. Active ingredient concentration (ppa). 36 900 100 0 37 900 100 0 38 900 100 0 39 900 100 0 40 900 100 0 41 900 100 0 * 2 900 100 0 43 900 100 0 44 900 100 0 49 900 100 0 46 900 100 0 47 900 100 0 48 900 100 0 49 900 100 0 90 900 100 0 51 900 100 0 92 900 100 0 93 900 100 0 94 900 100 0 99 900 100 0 96 900 100 0 97 900 100 0 98 900 100 0 99 900 100 0 60 900. The results summarized in Table 7 show that the compounds I according to the invention exhibit a remarkable preventive effect on resistant kaen, but do not show the preventive effect of the tested sensitive kaen. Unlike commercially available fungicides such as Benoayl and Thiophanate-ethyl, they exhibit a marked control effect on susceptible kaen but do not effect resistant kaen. Example 6

Preventive effect on cucumber black (Mycosphaerella aelonis).

The plastic quartz objeau 90 al is filled with sand p & d and placed in a seae-na cucumber (var. Sagaai-hanjiro). The cultivation is carried out in a greenhouse for 8 days, when the first two leaves of the seagulls are harvested. A dilute aqueous solution of the test compound in the form of an inhalable concentrate or an aliquot of 10 [mu] l per pot is applied to the plants. After air drying, the seaweed is inoculated with nyoelia discs (9 in diameter) of the resistant strain and mycosphaerella aelonis strain by placing them on the leaf surface. After seeding, the plants are incubated at high humidity for 4 days at 29 ° C, after which the severity of the disease is evaluated. The degree of damage to the Blanc by the procedure of Example 1 and the results are summarized in Table 8. 37 243487

Table 8

Compound No. Active Ingredient Concentration (ppm) Precautionary Values for Inoculation with Re-resistant Strain (X) Precautionary Values for Sensitive Inoculation (%) 2,500 100 0 5,500 100 0 7,500 100 0 9,500 100 0 11,500 100 0 31,500 100 0 34 500 100 0 35 500 100 0 36 500 100 0 Benomyl 200 0 100 Thlophanatemethyl 200 0 100

As can be seen from the results summarized in Table 8, the compounds I according to the invention exhibit a preventive effect on the strain resistant but do not have a preventive effect on the strain. The difference, commercially available known fungicides such as Benomyl and Thiophanate-methyl, show a marked control effect on the resistant strain. Example 7

Preventive effect on green mold orange (penicillium italicum).

The fruits of orange (var. Unshu) are washed with water and air dried. The fruit is immersed for 1 minute in a solution of the test compound prepared by diluting the emulsifiable concentrate containing the test compound with water. After air drying, the fruits are inoculated by spraying a spore of a resistant strain and a sensitive strain of Penicillium italicum and placed in a high humidity room for 14 days. The degree of damage is determined as follows.

Percentage of infected area is measured on the fruit and classified with the corresponding indexes: 0, 1, 2, 3, 4, 5:

Disease Index 0 1 2 3 4 5

Percentage of infected area undefined Infected flat infected flat infected flat infected flat infected area less than 20% less than 40% less than 60% less than 80% is not less than 80% in Table 9. 243487 38

Table 9

Compound No. Active ingredient concentration (ppm) Precautionary values inoculated with re-resistant strain (%) Precautionary values for sensitive inoculation (%) 7 500 100 0 Benomyl 200 0 100 Thiophanate-methyl 200 0 100

As is evident from the results summarized in Table 9, the compounds of the formula I according to the invention excel! a preventive effect on the strain resistant but does not have a preventive effect on the susceptible strain tested. In contrast, commercially available known fungicides such as Banomyl and Thiophanate-methyl show an effect on the sensitive strain but not on the reactive strain. Example 8

Phytotoxicity to crops.

150 ml plastic pots are filled with sandy soil and seeded with seedlings (var. Norin no. 61), apples (varietal Kogyoku) and peanuts (var. Chiba hanryusei). The test compound is applied to the seedlings in the form of a spray prepared by diluting the emulsifiable concentrate or wettable powder with water. After cultivation in the greenhouse, another 10 criteria.

Stage + ++ +++ The results are summarized in the 10th day table and the phytotoxicity was evaluated according to the following

Observation of no phytotoxic abnormality observed in the plant phytotoxic field observed in the majority of plant phytotoxicity causing plant death

Table 10

Compound No. Active Ingredient Concentration (ppm) Wheat Phytotoxicity Apple Peanuts 2 1,000 - - - Barban 1,000 ++ ++ CBPC 1,000 - ++ ++ Swep 1,000 ++ ++ + The results summarized in Table 10 show that the compounds of formula X according to the invention show no toxicity, while commercially available herbicides of similar chemical structure are considerably phytotoxic. 39 243487 Example?

Preventive effect on powdery mildew (Sphaerotheca fuliginea).

90 ml plastic pots are filled with sandy soil and seeded cucumber seeds (var. Sagami-hanjiro). The cultivation is carried out for 8 days in a greenhouse. For the 2-leaf seedlings obtained, a spray of a dilute aqueous solution of an emulsifiable concentrate or wetting powder in an amount of 0 ml per pot is applied. Then the seedlings are inoculated with a mixed spore suspension of the resident and sensitive Sphaerotheca fuliginea strain. The plants are then further cultivated by the greenhouse. On the tenth day after infection, the infectious stage of the plants is evaluated. The degree of damage is determined as described in Experiment 1 and the results are summarized in Table 1.

Table 11

Compound No. Concentration Active Prevention Value (%) Component (ppm) 1 100 42 1 20 0 7 100 40 7 20 0 28 100 38 28 20 0 34 100 36 34 20 0 35 100 42 35 20 0 A 100 45 A 20 12 B 500 42 B 100 10 C 100 42 E 20 10 F 100 43 F 20 8 0 100 42 G 20 8 H 100 40 H 20 5 243487 40

Pokr. tab. 11

Compound No. Active ingredient concentration (ppm) Prevention value (#) 1 + A 20 + 20 100 1 + B 20 + 20 100 1 + E 20 + 20 100 1 + G 20 + 20 too 7 + C 20 + 20 100 7 + D 20 + 20 100 7 + G 20 + 20 100 7 + H 20 + 20 100 28 + A 20 * 20 100 28 + B 20 + 20 100 34 + E 20 + 20 100 34 + F 20 + 20 100 35 + A 20 + 20 100 35 + E 20 + 20 10.0 From the results summarized in Table 11 It can be seen that the compounds of the formula I used according to the invention together with the fungicides benzimidazole, thiophanate and / or cyclic imide exhibit a higher preventive effect than that obtained on separate use. Example 10

Preventive effect on gray mold (Botrytis cinerea).

90 ml plastic pots are filled with sandy soil and seeded with seedlings (var. Fukuju # 2). The cultivation is carried out in a greenhouse for 4 weeks. A diluted aqueous solution of an emulsifiable concentrate or wettable powder is applied to the seedlings at the leaf stage 4 at a rate of 10 ml per pot. The plants are then inoculated by spraying with a mixed suspension of a resistant and sensitive strain of Botrytis cinerea and placed in a high humidity room at 20 ° C for 9 days. The degree of damage is determined as outlined in Example 1 and the results are summarized in Table 12.

Table 12

Compound No. Concentration of active ingredient (ppm) Value of prevention (*) 1 100 38 1 20 0

Claims

41 243487 Pok. tab. 12 Compound No. Active ingredient concentration (ppm) Prevention value (%) 7 100 36 7 20 0 28 100 34 28 20 0 36 100 32 36 20 0 I 100 48 I 20 22 J 500 46 J 100, 8 K 100 42 X 20 15 L 500 42 L • 100 12 X + I 10 + 20 100 I + J, 0 + 20 100 7 + 1 10 + 20 100 7 + K 10 + 20 100 28 + 1 10 + 20 100 28 + L 10 + 20 100 36 + 1 10 + 20 100 36 + J 10 + 20 100 It can be seen from the results summarized in Table 2 that the use of a compound of formula I according to the invention together with benzimidazole, thiophanate and / or cyclic imide has a higher preventive effect than that obtained on separate use. FIELD OF THE INVENTION 1. A fungicidal composition comprising as active ingredient a compound of the formula I N-C-B II Z A (I) wherein X is nitro, amino, isothiocyanato, alkylamino and 2 atoms

2434-7 42 -NH-CA "-R, or -NH-C-NH-R 1, n-2A, A-carbon or a group of the formula -RH-C-Rg, where A'a A" are the same or different substituents , selected from the group consisting of oxygen or atom of sulfur, Rg 3 with 1 to 3 carbon atoms, alkenyl of 3 carbon atoms, 3-carbon alkenyl or haloalkyl having 2 carbon atoms, or 2-methoxyethyl, alkyl of 1 to 3 carbon atoms, alkenyl and 2 to 3 carbon atoms, chloromethyl, methoxymethyl, hydroxymethyl, nitro, formyl, hydroxylminomethyl, alkoxy s, 2-carbon, methoxycarbonyl, hydrogen, halogen or acyl having 2 to 3 carbon atoms, hydrogen, hydroxyl or methyl is a hydrogen atom or a group of formula -ORj, wherein R 1 is alkyl of 1 to 3 carbon atoms, alkenyl of 3 carbon atoms, alkenyl of 3 carbon atoms, haloalkyl of 2 carbon atoms, methoxy-methyl, cycloalkylalkyl of 4 carbon atoms or cyanomethyl, is oxygen or sulfur and B is alkyl of 1 to 4 carbon atoms, alkenyl of 3 carbon atoms, cycloalkyl of 3 carbon atoms, phenyl or a group of the formula -WR 1, where the oxygen or sulfur atom, and R 1 is cycloalkyl of 3 and 4 carbon atoms, fluorophenyl, alkyl of 1 to 4 carbon atoms, alkenyl of 3 to 4 carbon atoms, alkenyl of 3 to 4 carbon atoms, 4 carbon atoms, haloalkenyl of 4 carbon atoms, haloalkinyl of 4 carbon atoms, cyclo-C 1-6 -alkyl-C 8 -alkyl, alkyl of 3 to 3 carbon atoms substituted by halogen, cyano, methoxy, phenyl, alkenyl of 3 carbon atoms carbonyl, haloalkoxy having 2 carbon atoms, phenoxy and / or benzyloxy, wherein R and Y cannot be simultaneously hydrogen atoms.

2. A fungicidal composition according to claim 1, wherein the active ingredient is a compound of formula (I) wherein the C1 -C2 alkylamino group is -NH-CR1 -NH-COH, or II II2 OO -NH. -C-NH-R12, where alkyl of 1 to 3 carbon atoms, alkenyl of 3 carbon atoms, alkenyl of 3 carbon atoms or haloalkyl of 2 carbon atoms, is alkyl of 1 to 3 carbon atoms, alkenyl of 2 to 3 carbon atoms, chloromethyl, methoxymethyl, hydroxylminomethyl, alkoxy of 3 to 2 carbon atoms, methoxycarbonyl, hydrogen, halogen, or alkanoyl of 2 to 5 carbon atoms, is hydrogen, hydroxyl or methyl; wherein R 1 is alkyl of 1 to 3 carbon atoms, alkenyl of 3 carbon atoms, alkenyl of 3 carbon atoms, haloalkyl of 3 carbon atoms, ethoxymethyl or cyanomethyl, is oxygen or sulfur, 5 is alkyl of 1 to 4 carbon atoms , alkenyl having 3 carbon atoms, cycloalkyl having 3 carbon atoms, phenyl or a group of the formula -WR ^, where W is a R 1 is cycloalkyl having 3 carbon atoms, alkyl of 1 to 4 carbon atoms, alkenyl of 3 to 4 carbon atoms, alkenyl of 3 to 4 carbon atoms, haloalkenyl of 4 carbon atoms, haloalkynyl of 4 carbon atoms, cyclic -C 1 -alkyl-C 8 -alkyl, or C 1 -C 3 -alkyl substituted with halogen, cyano, methoxy, phenyl, 3-carbon alkenyloxy, haloalkoxy, 2-carbon, phenoxy and / or benzyloxy.

3. A fungicidal composition according to claim 1, wherein X is a nitro, amino, isothiocyanate, or -NH-CR, A, 43, 243487 or -NH-CA ' Where A 'and A "are the same or different substituents, O or S, R 8 is alkyl of 1 to 3 carbon atoms, alkenyl of 3 carbon atoms, alkynyl of 3 carbon atoms, haloalkyl of 2 carbon atoms or 2-methoxyethyl, Ϊ is alkyl of 1 to 3 carbon atoms, formyl, alkoxy of 1 to 2 carbon atoms, methoxycarbonyl, hydrogen, halogen or ayl of 2 to 3 carbon atoms, Z is hydrogen, R is the formula -ORj, where R 1 is alkyl of 1 to 3 carbon atoms, alkenyl of 3 carbon atoms, 3-carbon alkynyl, haloalkyl of 2 carbon atoms, methoxymethyl, cycloalkylalkyl 3, 4 carbon atoms or cyanomethyl, A is oxygen or sulfur, B is a group of formula -WR1, wherein W is O or S and R8 is cycloalkyl of 3 and t carbon atoms, alkyl of 1 to 4 carbon atoms, alkenyl of 3 to 4 carbon atoms, alkynyl of 3 to 4 carbon atoms, haloalkenyl of 4 carbon atoms, haloalkynyl of 4 carboncyclo-C 1 -alkyl-C 8 -alkyl or alkyl of 1 to 4 carbon atoms 3 carbon atoms substituted by halogen, cyano, methoxy, phenyl, alkenyloxy and 3 carbon atoms, haloalkoxy of 2 carbon atoms, phenoxy and / or benzyloxy.

4. A fungicidal composition according to claim 1, wherein X is a nitro, amino, isothiocyanato or -NH-C-R8 or -NH-CA ' -RO group. A ' and A " are the same or different substituents, namely oxygen or < 2 > A sulfur atom, R2 is alkyl of 1 to 3 carbon atoms, alkenyl of 3 carbon atoms, alkynyl of 3 carbon atoms, haloalkyl of 2 carbon atoms or 2-methoxyethyl, X is alkyl of 1 to 3 carbon atoms, alkoxy of 1 to 2 carbon atoms, methoxycarbonyl, hydrogen, halogen or acyl of 2 to 3 carbon atoms, Z is hydrogen, R is -OR, wherein R 1 is alkyl of 1 to 3 carbon atoms, alkenyl of 3 carbon atoms of 3 carbon atoms, haloalkyl of 2 carbon atoms, methoxymethyl, cycloalkylalkyl of 4 carbon atoms, or cyanomethyl, A is oxygen or sulfur, and B is alkyl C 1 -C 4, C 3 alkenyl, C 3 cycloalkyl, phenyl or C 1 -C 4 alkenyl; the group of formula -WR1, wherein W is O or S, R1 is cycloalkyl having 3 carbon atoms, alkyl of 1 to 4 carbon atoms, alkenyl of 3 to 4 carbon atoms, alkynyl of 3 to 4 carbon atoms, haloalkenyl of 4 atoms carbon, haloalkynyl having 4 carbon-cyclo-C 1-6 -alkyl-C 1-3 -alkyl or C 1 -C 3 -alkyl substituted by halogen, cyano, methoxy, phenyl, 3-carbon alkenyloxy, 2-carbon haloalkoxy, phenoxy and or a benzyloxy group.

5. A process for the preparation of compounds of general formula I effective according to 1, x

YX is a nitro, amino, isothiocyanate, alkylamino group having 1 and 2 carbon atoms, or a group of the formula -NH-CR, -NH-CA "-R 1 ', or -NH-C-NH-R 7, k' * A '243487 44 wherein A * and A " are the same or different substituents selected from the group consisting of oxygen or sulfur, R8 is alkyl of 1-3 carbon atoms, alkenyl of 3 carbon atoms, alkynyl of 3 carbon atoms, or haloalkyl of 2 carbon atoms, or 2-methoxyethyl, Y is alkyl of 1 to 3 carbon atoms, alkenyl of 2 to 3 carbon atoms, chloromethyl, methoxy, methyl, hydroxymethyl, nitro, formyl, hydroxylminomethyl, alkoxy of 1 to 2 carbon, methoxycarbonyl, and hydrogen, a halogen atom, or an acyl group having 2 to 3 carbon atoms, Z is a hydrogen atom, a hydroxyl or a methyl group, R is a hydrogen atom or a group of the formula -ORj, wherein R 1 is an alkyl of up to 3 carbon atoms, an alkoxy β 3 carbon atom , 3-membered alkynyl, 2-carbon haloalkyl, methoxylmethyl, 4-carbon cycloelkylalkyl or cyanomethyl, A is the atom oxygen or sulfur, and B is alkyl of 1 to 4 carbon atoms, alkenyl of 3 carbon atoms, cycloalkyl of 3 carbon atoms, phenyl, or a group of the formula -WR 1, wherein W is oxygen or sulfur, and R 8 is cycloalkyl 3 to C 4 -C 4, C 3 -C 4 alkenyl, C 4 -C 4 alkenyl, C 4 -C 4 alkynyl, C 4 haloalkenyl, C 4 haloalkenyl, C 6 -C 6 -alkyl-C 8 -alkyl , alkyl having 1 to 3 carbon atoms substituted with halogen, cyano, methoxy, phenyl, alkenyl alkoxy having 3 carbon atoms, haloalkoxy having 2 carbon atoms, phenoxy and / or henzyloxy, wherein R and Y cannot be simultaneously hydrogen, except for methyl-N- Phenyl-N- (3-ethoxycarbonylamino-4-methoxyphenyl) carbamate (3-nitro-4-propyloxyphenyl) carbamate, wherein the compound of formula (II) X NH-Z (II) is reacted where X, Y, Z and R are as defined above, with the compound of general formula III (III) kae A and B is as defined above and R 8 is halogen or with the compound of general formula IV AA, II I, BCOCB (IV) wherein A is as defined above and B 'is alkyl of 1 to 4 carbon atoms, alkenyl of 3 carbon atoms, C 3 cycloalkyl or phenyl. Severografia, n. P „MOST Price 2.40 Kcs