SU736857A3 - Insectoacaricidonematocidic agent - Google Patents

Description

The invention relates to chemical plant protection products, insecticide acaciacemic acid based on oxime carbamates. A pesticide is known, the active ingredient of which is derived from oxime carbamates 1. The closest in chemical structure to the proposed compound is insecto-acaricone nematode. Based on 1-cyanbutanaldoxime-N-methylcarbamate 2. However, these insectoacaride nematocides have a short-term activity at low concentrations. The aim of the invention is to find new insecticide-acaric nematocidal agents, possessing high biological activity. To achieve this goal, it is proposed to use as a derivative of oxime carbamates compounds of the general formula / O m E R-C: C-0-C-W; methyl, isopropyl, t-butyl; hydrogen or methyl; methyl, methoxymethyl or the group —S — R 4. or - (S) -R5-, in which R is trichloromethyl, fluorodichloromethyl, trifluoromethyl, methoxycarbonyl, phenyl, unsubstituted or substituted by chlorine, or trifluoromethyl, or radical, of the formula -Y {CH) -5O "- -CHj; R5TOT radical, with which the group is associated - (8) gi-Re; m-numbers 1 or 2; imidozolyl, 1,2, 3-triazolyl-2 pyrazol; unsubstituted or substituted by chlorine with a nitro group, methyl, ethyl or methyl mercapto, 1,2, 3-triazolyl-1, unsubstituted or substituted with chlorine, methyl, ethyl or methyl mercapto group, 1,2, 4-triazolyl-1, unsubstituted or substituted by chlorine, ethyl, nitro or methyl mercapto group; direct bond or methylene,

. ...- ..--- ....

or THEIR SALTS WITH TWO-CHLOROUS ZINC

hydrochloric or naphthalene disulfonic acid, in the amount of

  0.1-95 wt.%, Preferably 0.590 wt.%, And compounds of the general formula 1 can be used as individual isomers or as a mixture

: isomers. The compounds of formula 1 can be obtained by the interaction of the oxime of the general formula

KOH R-C

(g)

Guise

with isocyanates of the general formula

(3)

R, -N - Ct: 0

in the presence of a diluent, if necessary, in the presence of a catalyst (A),

or with carbamoyl chlorides of the general formula

, -RI

CI-CO-K;

2: (

in the presence of a diluent and an acid binding agent, or in the presence of a diluent and nati hydride or phosgene and then with an amine and a common formula

 (5) (5)

in the presence of a diluent and an acid binding agent, or in the presence of a diluent and nati hydride, or with sulfenylated carbamoyl halides of the general formula

L1

-and/

And 01-SO-ME

(6)

- (..)

In the presence of a diluent and an acid binding agent or oximecarbamates of the general formula

R.-O-CI,

(7)

ks

n (7)

ZH,

exposed to sulfenyl chlorides of the general formula

a-CS) - “g (8)

in at (rutting of a diluent and a bond with an acid of an acid. In formulas 2-8 R, R, R j, R,}. ™ have. -the indicated values, HAE - fluorine Or chlorine. - All inert organic solvents are suitable as a diluent; nitriles , alcohols, ethers, forms and halogenated hydrocarbons.

Tertiary bases and organic tin compounds can be used as a catalyst for SPC A).

The temperature of the reactions can be varied, usually it is equal to O-lOO c.

Inorganic and organic acid acceptors such as alkali metal carbonates, lower tertiary alkylamines, cycloalkylamines or arylalkylamines, as well as pyridine and diazabicycloooctane are suitable as a binder for kiagute.

Compounds of general use are of formula 1: solutions, emulsions, wettable powders, suspensions, powdered preparations, foams, pastes, soluble powders, granules, aerosols, suspension and emulsion concentrates, powders for seed, impregnated with an active principle, natural and synthetic substances, microcapsules in polymeric substances and membranes for inoculum, in addition, preparations with a combustible composition, as well as preparations for hot and cold methods of mist formation.

These preparations are prepared by known methods, for example, by mixing the active principles with diluents, i.e. liquid solvents, pressurized liquefied gases and / or solid carriers, if necessary, when using surfactants, i.e. emulsifiers and / or dispersants and / or blowing agents. If water is used as a diluent, auxiliary organic solvents can also be used. Suitable liquid solvents are aromatic hydrocarbons, chlorinated aromatic or aliphatic hydrocarbons, aliphatic hydrocarbons, as well as their ethers and esters, ketones, highly polar solvents such as dimethylformamide and dimethyl sulfoxide, as well as water. By liquefied gaseous diluent 1 or carrier, it should be understood that such liquids are. Normal conditions are gaseous, such as halohydrocarbons, as well as butane, propane, nitrogen and carbon dioxide, under solid carriers - natural stone meal, such as kaolin, alumina, talc, chalk, quartz, attapulgite or diatomaceous earth, and synthetic, stone flour, such as highly dispersed silicic acid, alumina and silicates, under solid carriers for. granules - crushed and fractionated natural stones, such as calcite, marble, pumice, sepiolite, as well as synthetic granules of inorganic and organic flour, as well as granules of organic material, such as sawdust, coconut powder. , maize noats and tobacco stems, under emulsifiers and / or frothers - non-ionic and anionic emulsifiers, such as polyoxy (fatty) acid esters, polyoxyethylene (fatty) alcohol ethers, alkyl sulfonates, alkyl sulfates, arylsulfonates, and also protein s hydrolysates under dispersants - lignin from the treated sulfite liquors and methylcellulose,

Adhesives such as carboxymethylcellulose, natural and synthetic powdered, granular or latex-like polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, may be contained in the preparations.

Example 1. A preparation containing active nalgalo, carefully

Experiments with nematodes MeColdogyne incoghita

Active principle

mixed with soil strongly affected by experimental nematodes. The pots are filled with the treated soil, the lettuce is sown and the pots are left to stand at a greenhouse temperature of 27 ° C.

At the end of 4 weeks, lettuce roots are examined for nematode damage (root galls) and an op.

the beginning. The degree of efficiency is 100%, if by agiae is completely prevented, and is 0%, if the lesion corresponds to a pore-control plants in the untreated,

but equally affected soil. Actual principles, applied concentrations and results of the experiments are given in Table. 1.Table

The degree of killing,%

Concentration of onset 10 ppm

C} H7-C

N-0-OO-IN-SNZ

(HiSecmHOe)

noo, ck

nn

CHj Н-0-СО-КН-СНз

(C} western)

N-0-OO-NH-CHj (CH3)

"Ftz-n

N-O-PO-HH-CHj

(SNS) zs-S

N-O-CO-NH-CHj

CH2-H (I CzHs

N

r

N N-Q-CO NH -СНз

 v

mo

100

100

100 N

100

100

NH-CH3

100

i-co-in-snde

With SNZ-y K.

CH7 - N /.

CIS-IOG N-0-CO-CN-CHCxC.sxis. (ns) 1/2 OP CH7-Htg | 1SOjH

The concentration of active start is 5 ppm. (shlh c -o-co-nim-N (H "Concentration of CH}. N - 0-CC N-Str. C k. .. 11 II CH, I N-0-CO-NS. Tre / P-

Concentration of onset is 20 h, ppm.

9 "W

I К-0-СО-ННСКз СН2-С-С

n

SNS

(fair)

736857-8

Continued table. j

I S03H ° C. d.p. 100 starting start 10 ppm. CH N-S02- / O) -CH3NuO - /. CH I N-S024OV H3 00 -. O-CO-N-SCClj

N-0-

(SNS) zs-S

l

N-0-CO-N

(SNE)

L "

Jl

0-Ce-N-J-S2 o -CO-N-S.

O-CO-H-S-CO-OSYAZ

N-O-CO-H

(CH) 5С-С

L:

736857

10 Continued table. one

"

100

100

100

sn, l

100

CH, CPH

100

100

100

CH}

N-0-CO-N-S-CO-OCH3

1СНз) ЗС-С N

Q

sn,

N-0-CO-N-SCCl3

(sns) es

6

SNS

N-0-co-N-SCClgF

(SNS) zs-S

cis

i

to - N-01SNz) eS-S

cis

6

NN-0-CO-N

ins) ss-sn

3

N

one-

with",

, N-0-CO-N -

1СНз) ЗС-С

cis

/

N-jj

Continued table. one

iiziii: iii

100

100

100

100

100

CALL

96

100

CALL

sns

I

0-CO-W-SСНз

.k-0-co-N-s - (() bC1

(SS, C-C

sn,

N

 G

N-0-CO-NH-CHg -OCHN

Tresh-C;, H9 -c I N

K-O-CO-N-SCFj

Tjpem-C / jHg-C I K

. f

N-0-CO-N-STpem-C / jHg-C B

N-0-CO-N-SCCl3

Trell-C / jHg-C N

N

CI

Continued table. one

100

100

100

100

100

100

- CH,

100

N-0 -CO-NH-CH3 Tpem-c / tHg-C

SI g

N

N02

Q

Y

-N

7ret-ad-s - - - "-" 3

P T

, N-0-SO-IN-SNE

Gret - CijHg-С

BUT

SNS $

N-O-CO-IN-SNZ-CifHg-C

-N.

but

Nog

Continued table. l)

I 2

100

100

iOO

100

SNTSSTz

-sn -s- - - - rpem-c Hg

100

N-O-CO-H

-CjjHg-C

L

I I

Gresh-S.Ne-S- - - - - W

H

Cl

-s, Ne - s - ° - ° - "" - "e

h

SI,

OH3100

100

100 i-o-so-nn-$ -soosnz

-C / fH9 9

to

to

N

C1 N-0-CO-S-S-SOOSIZ

-SOS; H9-CA

BUT

K-0-SO-Ya -S -COOCH}

C) 1, H9 - C

-: N

n, with K-0-CO-N-S-COOCH3

c / jHg with d

| R

to

H5S2

in-6-co-ga-si} hot. - c iHg-s

g

, N-0-CO-NH-CHj

tert- CifHg- C

CH2 N.

ng,

C1

..k-o-co-ga-snz

tert - - C

cis

N

iTti

Continued table. J

.one

100

R,

100

SNE

100

SNS

100

100

100

100

.N-O-CO-NH-CH3 Tpeni-Cj Hg-C

sig kg%

"SC"

C,

ong

L and

N02 c,

B

"Lg

CHjS

sn,

., I-0-CO-K-S-COOCHj gret-CifHg-C

Ln 1

K02

SNS

ret-.4ne-c - - n

Gf

.to-

R-O-CO-NH-CH3

p ffi-Ci, H9-s

j-v

-L

CzHs

N-O-CO-NH-CH3 pem CijHg-С

s; n,

To and SCH3

 K-0-CO-NH-SNE

"

ret-CijHg-С

CH2 K

about

and-y

H-O-CO-NH-CH3 tert-CijH9 -

he,

BUT.

Continued table. one

100

100

100

100

100

100

100

X HC1

100

X znol2

100

Example 2. The drug containing the active principle, thoroughly mixed with the soil. The treated soil is placed in pots and cabbage is planted in them. The active principle is absorbed by the roots of the plants from the soil and enters the leaves. In order to assess the corneal effect, after expiration of 7 days, experimental insects are planted on a sheet. Rocksystem Effects, Phaedon Experience

The concentration of active start is 10 ppm.

V-O-CO-NH-CH3

CjH7-C

CR

(known;

H-O-co-NH-CH3

-P

: sn-s

: CN

(known)

H-O-CO-HH-CH3 ()

CIS-N

M-O-CO-NH-CH3

WITH

 / cs-x

-N

to - 0-CO-NH- СНзSOjH

WITH

oH, -KQ

(CHj) with - C N-0N

g

II 1

and-

1СНз) ЗС -C N-o-CO-NH-CHj

SLJ

(N-0-CO-NH-CH2-OCHs

l

I-j

After another two days, the coronary action of the active principle is determined, which is 100% if BC0. The experimental insects are euthanized, and 0% if they still live.

There are as many HaceiKO # ix as in the control experiment, Acting, the applied concentrations and the results of the experiments are given in Table. 2

95

100

100

§ОЗН

100

100

100 Table cochleariae (forge)

Concentration of active start 20 ppm,

With “s

,,. # NHO-CH -C-C H

SNS

(known)

sn,)

 L II II

) ZS -S

m

K

SSNZS- with

I

N

R

11-j

 9 "W

CO-H-5- (O /

Chr

, N-0-CO - K

SNE) 5C-C N

N-0 -co - N-S-CO-OCHj

(SNS) eS-S

N

sn,

and-o-so-and

with

I

N

Continued table. 2 2

100

100

100

100

100

100

100

f "3 CF,

0-CO-N-S4O .. N-0-CO-ll-S-CO (CHjljC-C II n-

SNS

.. and-0-co-u-scci T

- (СН5) ЗС-СCHz

N-and

N-0-CO-K-SCClj

(СНз) 5С-с

CIS AN

 if to-and

N (СНз) ЗС- €

CNG

R

to-

N o -CQ-K

with

cis

L

II II

 II

N-l

N-0-CO-K-S-CO-OCHNz

with

her,

city-Continued table, 2

100 ,

tea

. 100

100

100

CH3

S03tt

100

h

2 OZN

100 SNS

"V - l

O-CO-N-S / O -I (SNe) sC-C

cis

Experiments with Myzus persicae

Active starting concentration 10 ppm -O-CO-NH-CH,

WITH

sko

 known)

«« 3-CH-С ° СНз CN

(known

., N-0 - CO - NH (cps) es-e cis-nQJ

S-O-CO-NH-CHj СНз) ЗС-С- / К п

CH2-H (I

N-O-CO-KN Siz

,

 CIS- / Dt / 2 (OlQ

Mr. C I

Concentration of active starting 20 ppm

SNE

, CH, -t-c but-cis

I to

SI,

(known)

SNS

° - - Continued table. 2

100

100

about

95

100

$ OZN

90

ozi

100

0-CO-N

0-CO-K O-CO-N-SH (Q)

, G-0-CO-to

 -

U N-0-CO-N-S-CO-OCH3

-with

(SNZ) s with - with

0-CO-N-SCC13

, .N-0-CO-W -

(SNS) ZS-with N

 ABOUT

Continued table. 2

100

100

sns,

100

sns o

I ii.

100

100

Jh3

100

.

100

100

31

736857

.H-O-CO-W-SCCl T

(SNS) zs-S

N

SI, Tz

; N-o-co-i r-s- / Q /

WITH

n

to

. R

,} So-co-N-SCC13

 with

CH2 N

G

™ ,.

to-o-so-s

(, SNS) ZS-S

CH2

L

SNS

sn,

I

K-0-CO-K-S-N S02

 I n - ciiio - yy

G

Example 3. The preparation of the active principle is thoroughly mixed with the ground. The pots are filled with earth and left to stand at room temperature. After 24 hours, the experimental larvae are planted in the treated one, and after a expiry of 2-7 days, the degree of effectiveness is determined.

Experiments with Phorbia antigua (larvae in the earth

Concentration 20 ppm

Nz

.jK-O-CO-NHCH,

no-cng-c -c tK,

(, out of 8)

SI,

j)

sn

N

rj

NLCI

32

Continued table. 2

300

100

100

100

100

acting rocking by counting the dead and living larvae. Efficiency is 100% if everything is experimental. . larvae are euthanized, and equal to 0%, if as many larvae survived as in the control experiment. The effective rocking, concentrations and results of the experiments are listed in Table 3,

Table 3

100

N

1СНз) ЗС-С

to

with

to-

CO-N-S-CO-QCH,

co-N-S-co-NCO

1sn,)

N

. Ny-o -CO-N-S -N - SOg ter -CijHg- with

N

| R

Have

 N-о-со-W-S -к-S02 - (rjV-CHj

tert - CijHg- with

. SNG

N

rjN-J

; M-O-CO-NNz zS-C

Chz

to

g

S-0-co N -S-co-osnz

(SNS) W CC

Continued table. 3

100

100

100

100

SN} SNZ

-CHj

100

SNtSNg

I j 5

100

fH3 $ OCH

100

X pp

Mr. S03H

SNS

100

SNS

f-0-CO-N-S-O)

-about

(СНз)} С-С

cis

th

; N- O-CO-N-SXO /

WITH

cis

I

N

 .

Example 4. Before the formation of droplets, the preparation containing the active principle sprinkles the plants with cabbage strongly affected by peach aphids, or sprinkles the 7th leaves; the larvae of the stale leaf are put on them. :. .20 After the specified time

Experiments with insect pests Myzus Active principle

from the beginning,

(SNS) 3 ° 3

-TO

Of,

1СНз1зС.-С Н-0-СО-NH-CHg-ОСИз

N

rCH3) 3C- N-0-CO-NH-CHj N

N

1CTN3) 0-CO - NH-CH3

BUT

Continued table. 3

100

100

%%

After 1 day

uh

0.1

99 98

oh oh 1

100 100

0.1

100 9L 0.01

0.1

100 99 0.0i Concentration deist - The degree of killing. Determine the degree of killing. At the same time, 100% means that all aphids or larvae were euthanized,, 0% means that not a single tl or. Actual principles, their concentration, evaluation time and the results of the experiments are given. 3 tab. four . T a b l and c a 4

"W

Continued table. four

Siz

I N-O-C-NH-CHi C-cC.,

cn

I

SNS

. W / X HOI

STZ

SNS

I g

 to - about - with -W- S 4Q

CzjHg-C N

Continued table. four

0.1

99 80 y, 01

0.1

100 98 0.01

0.1 ...

.100 90 0.01

K-Q-CO-H

but

JTpem-CjfHg СI N

And-0 -CO - HH-CH3

ff-CijHg-C

and

Experiments with horseradish leaf beetles

., VLo-expiration 3 days

N-0-COcjHy-cc;

; .....:.

(On the day)

N-Oine) 2sn;

si

(known)

 .M

Ho-cH-c-cC

SNS (zveshot /

100 95

0.1 0.01

100 98

0.1 0.01

100

0.1

about 0.01

100

about

80

about

Continued tavl. four,

Example 5. A preparation of the active principle sprinkles cotton leaves to dew moisture.

(nirsutum and caterpillars are planted on them (Lapb-i ma exicyua). After a specified time, the degree of killing is determined.

Experiments with insect pests Laphygma

CjH7 C N-O-CO -CN-CH3 CN

(known)

1СНз) s C-C-N-0-CO-IN-SNE

n

(CH3) cc-C K-0 -co-NH-CH

 l

Jlj

C1

Uhj; s-s-n-0-so-kng

 KJ

about si 11

1, M-0-C-NN-SNCh

.

 wy.

Before the formation of droplets, the preparation is sprayed with spraying plants strongly affected by the pest (Tetvat chus and lsaee 1.).

After the specified time -,., ".::, Determine the degree of killing. With

100% means that all the caterpillars were killed, 0% means that not a single caterpillar was killed. Actual beginnings, their concentrations, the time of assessment and the results of the experiments are given in table. five.

Table3

100

0.1

about

0.01

100

0.1 80 0.01

100

0.1 100 0.0i

100

t, 1 100

0.01

1.00

0.1 100

0.01

this 100% means that all pests have been killed, 0% means that no pest has been killed. The current values, their concentrations, the time of assessment and the results of the experiments are given in Table. b. Experiments with harmful plants

; N-0-CO-NH-CH}

SzNt-with:

CN

(known)

: K-0-CO-HH-CH3

(sns) gsn-s

CN

(Known)

sns

NNO-CH2-C-s

n

"W

(favorite)

sn.

n-0 -co-c-S - co-base

WITH

n

7

N

. ".

CO-N-S-CO-OCH3

SNZ, N-0-CO-N-SCCl3

1СНз) ЗС-СN

M

.IT-O -CO-NI-CH J

tert - Ci Hg-С

H

SNS

SVS °

I H-0-C-YAN-CH3

After 2 days

0.1

0.1

0.1

0.1

100

0.1

99

85

0.1

0.1

100

98

0.1 Tablib Tetranychus

About SNLII

cH, -i-ct-- in,

N-O-CO-SH-CHj

Ytor SzV; -C

H

K-U

CHj CH3 fH-O-CO-U-S-H-S02iso-C} H 7-c N

oh-so-so-n-sng-osnz

tert -Ci, H9-С S

about

to

R

.n-oo-n- $ stz

Cj, H9 - C

about

about

 5-0-C-UN-CH3

CHj-c-cc;

and,

5 K-O-C-NH-CH

X 2пС1г

t,

™, ss.

sn,

H-0- co-to-S-- COOCH3

C jttq-c

t -i I and

-N

| R

Continued tab.

80

0.1

0.1

100

0.1

100

-Snz

0.1

100

/

100

0.1

98

0.1

0.1

80

0.1

100 N-0-CO-N-SCCl3

rpem-cz hg-c

N

f H .K-O-CO-NH-CH

.C- iK

fT il 11

N-L.

C2H5

N-0-CO-K-SCCii

-CzfHg-C

I n

nf

KCl

CHj

.K-O-CO-N-SCClgT (CH3) 3C-C

, .N-0-CO-il (СНз) ЗС-С

to w

H H- (СНз) ЗС-С

N

 f

N-u

SzN7-C H-0-CO-CN-CH3

CN

(known)

CH ,.

CH-C :: N-0-CO-NH- CH

"" 3CN

. (known)

Continued table. 6

CHj

100

0.1

0.1

100

0.1

100

0.1

98

80

0.1

100

0.1

0.1

0.1

51

(with n-o-so-in-ske

%

pu-u

SNS

, K-o-co - "- s- (Ol

tert-CifHg-C

736857

52

Continued tabl, b

99

0.1

After 3 days

0.1

100 0.01. 100

H-0-co-HH-CH3

, -f

sn,

n

(f

and I

nr-sn

X Zn Cl2

Cj, H9-s

scg

and-

C-O-CO-H-SCC13

to

one

 f 1

, H-Q-CQ-H-CC1h

Ci Hg-s

n

-one

N

C1

To-about-co-in-SNZ

C (, tt5-С

R

CZ 5

Y

-K N-0-CO-HH-CH3

 -with

cis

/-V.NO,

IL

100

0.1 100 0.01

100 80

0.1 0.01

100

0.1 100 0.01

100

0.1 100 0.01

Yui

0.1

100 0.01

100

0.1 100 0.01

.-jN-o-co-jra-snt

Tjjem

cis

T.em-c, H9-C ° ° ™ - "3

n

N02

SNS

, N-Q-CQ-N-S- / O

Gret - c / jHg-C V - //

N N

SNZ N-0-CO-l -S -СООСНз

rpem-c / fHg -C

 N N

Jl

NbSg

Continued table. 6

0.1

100 0.01 100

0.1

100 0.01 100

0.1

100 0.01. 100

100

0.1 100 0.01

CHj

..K-0-CO-NN-CH3

CijHg-C

CHg

I

well

to, to

L

Cl. H-O-CO-PN-CH3

- -Sung

tr XtT Ijt

Ck

H-0 -CO-JAN-SNE

-C / jHg-s

cis

n to /.

A-li

Hscz

K-0-CO-HH-CHi - -C

Sig kak

in

, -N-0-CO-N - $ - / O

mpem-c ho-c

CHj s

K-o-co-N - $ - / o)

"R LJ

Continued, fi

100

0.1 100 0.01

0.1

100 0.01

100

100

0.1 100 0.01

100

0.1

100 0.01

100

0.1

100

0.1

g

CH-C ° ° -XO) C,

yy i ii

and NO-CO-IJH-CH, mpem-c Hg-C, CH,;; „-C 5 mpem-c Hg

N

about

I-vi

N

Tf-0-CO-7QH-CHj

mpeifl-C, Hg-C h at I

Continued Table. b

0.1

100 X HCl

100

0.1

-o-coiCHj) jC-C

ir-O (CHjljC-C

: N-U

Cl

TJ-0-CO - N- $ CCii, r

CF,

CH,

o-it-s- / o

SNSS,

do- i "-p- j

0-CO-BN- (1H.

N

,

CH,

I-0-CO-Tl-5-COOCH,

rapem-c.

,

K-0-co-K-ecci j

c Hg-c I

L

II II

N

N-O-CO-T H-CHropem-c, Hq-c

"Uh,.

 V. , Continued table. 6

100 90

0.1 0.01

100

0.1 100 0.01

100

0.1 100 0.01

0.1

100 0.01 100

0.1

100 0.01 100

0.1

100 100 0.01

100

0.1 0.01 100

0.1

100 0.01 100

0.1

00 0.01 1 0 0

SI. CH,

1I

: M-O CO - N -S -c- $ 0, - (

V

SYZ CHI I I

B-o-so-mz-i-o, - (

 V w /

-1I

Sn, Sn, II

 IT-O-CO-U-S-N-SO - O

hv

Thus, compounds that have been proposed have high biological activity at low concentrations.

Claims (1)

Invention Formula Insecticide acaric nematocidal agent containing an active, chalo; Based on oxime carbamate derivatives and an additive selected from the group of solid and liquid carriers, in order to increase the biological activity, it contains a compound of the general formula as an oxime carbamate derivative ABOUT I Ri 5-С-К-0-С-К I g Z I R. de R is methyl, i-propyl, t-butyl; R, i is hydrogen or methyl; Rj is methyl, methoxymethyl or —Z-Cd or -li group - (B), „- K5 - where R4- tgi.chloromethyl, fluoride chloromethyl, trifluoromethyl, methoxycarbonyl, phenyl, unsubstituted or substituted by chlorine or trifluoromethyl, or a radical Formulas -N {CH ,,) - 50.- -CH ,, -, Rj i the same radical with which linked group - () - Rj m - integers 1 or 2; RA - imidazolyl, 1,2, 3-triazo-LIL - 2, pyrazolyl, unspecified. Continuation of table. WITH 100 0.1 90 0.01 0.1 100 0.01 100 0.1 100 100 0.01 chlorine, nitro, methyl, ethyl or methyl mercapto, 1,2,3-triazolyl-1, unsubstituted or 0 substituted by chlorine, methyl, ethyl or methyl mercapto group 1,2,4-triazolyl-1, unsubstituted or substituted by chlorine, ethyl, nitro methyl methyl mercapto group, Z is a direct bond or methylene, or its salt with zinc dichloride, hydrochloride or naphthalene di-sulphonic acid, and containing. The effect of the active principle in the medium is 0.1-95% by weight. Priority on the prize to the m: 03/27/76 at R-methyl, isopropyl, t-bu / thyl; Hj is hydrogen or methyl; Rz methyl, methoxymethyl; 0 imidazolyl, 1,2,3-triazoR lil-2., Pyrazolyl, unsubstituted or substituted by chlorine, nitro, methyl, ethyl or methyl mercapto group 5, 1,2,3-triazolyl-1, unsubstituted or substituted by chlorine, methyl, ethyl or methyl mercapto group, 1,2,4-triazolyl-1, unsubstituted or substituted by chlorine, with this metal, nitro or methyl mercapto group, Z is directly connected with methyne, 10.08.76 with 5 R -Н СНз1- -Вог- Ou-Iz2. -kl. C 63 73685764 groups 5-Cd- and - (5) -K ,, whereSources of information P "° P" "F ° Rda - ° Fm-taken into account in the examination of teal, trifluoromethyl, methoxycarbo- or za-, labeled with chlorine or trifluorome- ":. 483196, tilom silt radical of the formula, publish., 13.02.70 German patent No. 1567142, 07 C 131/00, off. 12.12.74.