UA74839C2 - Tetrazole derivatives, herbicide composition based thereon and an intermediary compound - Google Patents

Abstract

The instant invention relates to novel tetrazole derivatives of the formula (I) wherein R1 represents halogen, methyl, ethyl, halomethyl, methoxy, ethoxy, Ñ1-2 haloalkoxy, methylthio, ethylthio, Ñ1-3 alkylsulfonyl, methylsulfonyloxy, ethylsulfonyloxy, nitro or cyano, R2 represents C1-6 alkyl, Ñ3-6 cycloalkyl which may be optionally substituted with halogen or Ñ1-3 alkyl, C1-4 haloalkyl, C2-6 alkenyl, or phenyl which may be optionally substituted with halogen, Ñ1-3 alkyl, Ñ1-4 haloalkyl, Ñ2-6 alkenyl, or phenyl which may be optionally substituted with halogen, Ñ1-3 alkyl, Ñ1-2 haloalkyl or nitro, m represents 0, 1 or 2, two R1 may be identical or different, in case m represents 2, n represents 1 or 2, Q represents one the cyclic groups which are mentioned in the specification, to intermediates and several processes for their preparation, to their use as herbicides and to novel compositions containing them. (I)

Description

Description of the invention

This invention relates to new tetrazole derivatives, methods of their preparation, their use as 2 herbicides and to new herbicidal compositions containing them, intended for use in rice fields.

It is already known that some types of tetrazole derivatives exhibit herbicidal activity. publication of Japanese patent applications Mo12275/1999, Mo21280/1999, etc.). In addition, it is known that some types of heterocyclic derivatives have herbicidal activity | see US patent Mo5834402, Mo5846906, OE-A-19846792, UMO 99/110327, etc.).

Now new tetrazole derivatives of formula (I) 2 have been discovered. x 2 of them Food 1 M a Z / "tm z | en, 7 Z x c - in re 4 M g chai de

B' means halogen, methyl, ethyl, halomethyl, methoxyl, ethoxyl, C. o-halogenalkoxyl, methyltuyl, ethylthioyl, Si. z-alkylsulfonyl, methylsulfonyloxyl, ethylsulfonyloxyl, nitro- or cyano group,

B2 means C.alkyl or C.sub.6-cycloalkyl, which may optionally contain as substituents halogen or

C, 3-alkyl, or means C 1-haloalkyl, C 6-alkenyl or phenyl, which may optionally contain halogen, C 1-3 alkyl, C 1-0 -haloalkyl or a nitro group as c substituents, or is equal to 0, 1 or 2, and two substituents B! can be the same or different, if t is equal to 2, then n is equal to 1 or 2, o means the following groups (о) со с « and - - с . and? -I sh" (ee) at 50 iChe)

F) name) 60 b5 vi o

Y Kk 2 k o (0-X vk v v! v a v. e ich o (0-2u,

Kk

І е сх о ях я со со 1 Z " : V ich- y xx y "

Kk y o (9-3), - with Kk hu. :» Kk -I 15 so at 50 s

F)

Po) bo 65 -5B-

in o

Y Kk 2 k o (0-X vk v v! v a v. e ich o (0-2u,

Kk

І е сх о ях я со со 1 Z " : V ich- y xx y "

Kk y o (9-3), - with Kk hu. :» Kk -I 15 so at 50 s

F)

Po) because 65 in o

Y Kk 2 k o (0-X vk v v! v a v. e ich o (0-2u,

Kk

І е сх о ях я со со 1 Z " : V ich- y xx y "

Kk y o (9-3), - with Kk hu. :» Kk -I 15 so at 50 s

F)

Po) because 65

"7-5 in in! 5

And and ; o (0-5),

Kk in! in

Kt

XX

With t. cm o and o (0-5, and Ge") k v! p (ee) « di v" ich- 4 v se « i - s KE o

I" where in and Kk (0-56), -I in or so in" c" 7 to (Che)

In " o

F. E! p with gO-7u, 60 b5

"7-5 in in! 5

And and ; o (0-5),

Kk in! in

Kt

XX

With t. cm o and o (0-5, and Ge") k v! p (ee) « di v" ich- 4 v se « i - s KE o

I" where in and Kk (0-56), -I in or so in" c" 7 to (Che)

In " o

F. E! p with gO-7u, 60 b5

"7-5 in in! 5

And and ; o (0-5),

Kk in! in

Kt

XX

With t. cm o and o (0-5, and Ge") k v! p (ee) « di v" ych- 4 v-- ih « y - s KE o

I" where and t (0-56), -I in or so in" s" 7 to (Che)

In " o

F. E! p with gO-7u, 60 or b5

"7-5

With a and

IS

5 points (9-5),

Kk and V

Kk Kk 5 -shzhkh

With her

Kk cm at 5

In o (0-5), b (is) ots in so (ge) «І 1 h- in k 4

Kk -- « i - s Kk o

I» ih, v' Kk (0-5), -I v or so v" (95) 4

Kk (Che) 5

Kk " o v yu od gO-7u, because where

BZ, 7, B", 85 c and 88 are the same or different and each of them means a hydrogen atom or methyl,

VE? means a hydrogen atom, halogen, C. 3-alkyl, halomethyl, methoxy or nitro group,

BO stands for Ci-C alkyl, and B stands for halogen

K is equal to 1 or 2.

Compounds of formula (I) corresponding to this invention can be obtained by a method in which a) in the case of obtaining a compound of formula (I), where O means groups (0-1) or (0-2): compounds of formula (II) and about B ' (Z,

M. t" IM (sndiV-X Y FO 70 t -Y

Where is it?

B, B, t and n are as defined above, and

T means one of the following groups со (22) со с " ч- " ши с ;" -I sh" (ee) at 50 iChe)

Ф) име) 60 b5 c" in where 0

Kk i vd3 c) de - sch do o s. o to v ro F so ne) « pjZ56-- ich- 4

Kk "-s x" in o vo 7 - Kk i" so , or d) te) o

Te (F) tr in-- bo to

EE in" where 0

Kk i vd3 c) de - sch do o s. o to v ro F so ne) « pjZ56-- ich- 4

Kk "-s x" in o vo 7 - Kk i" so , or d) te) o

Te (F) tr in-- bo to

EE в ю В о в? k vd3 (8! de - s to o s. o y se v ro F so (ge) "I pp/-A-- m- 4

Kk "- that 5 th" Kk o v 47 U ev s" nya or (95) so o v

F) who in? oh- because to

EE or with 4; -

Kk r.

Kk v yu ku o

E 7 in pc with 0

Kk and

Kk - with 5 (o) in bto--

B entrance 7 V F

Kk Kk so (ge) "I pyZr.- ich- 4

Kk " - - 5 g" Kk at 8

EE 7 - Kk s» so or o 50 te) o 4 t (F) ko v

At 00-- because V

Kz

Kk where 65 BZ, 7, B, 85 in and 8 are as defined above, are subjected to the rearrangement reaction in the presence of inert solvents and, if appropriate, in the presence of a base and cyanide and, if appropriate, in the presence of an interfacial catalyst, or b) in the case of obtaining a compound of formula (I), where O means groups (0-6) or (0-7) and in the indicated groups B! means chlorine or bromine: compounds of formula (IB) 2

Ha; , e (Kz !

IM ka o i - 4- (sn u 5 ni and SNU m (c)

NOT M - where

B", B, t and n are as defined above, and

Oh means one of the following groups

K wo vy i y y (0-0, with schi s y; o or o (o)

A ' so v s « i k o m- (0-2),

Kn tk or « 31 o shi

Kk s y " Kk y?

Z z 7 y (0-9 ve What and (ee) so " avo iChe) o

Kt and;

Ф) і ko as shchi (0-2), 60 Vo tk where 23, 7, c", Vb, c and 28 are as defined above, are introduced into the reaction with a halogenating reagent in the presence of inert solvents, 65 or c) in the case of obtaining a compound of formula (I), where C) means groups (0-3), (0-4) or (0-5):

compounds of the formula (Is) o ' in ; (with a; n - M (snd,-5-

M -t

Pe) 10 de

B, B, t and n are as defined above, and

Or means one of the following groups 1c and dz k 4

Kk 20 and o v s i 8 v! e (o)

Ge) zo or her s so

Kk "I

Ge ich- « 5 - s Kk o);

And" and;

Kk in! - or c" (ee) o 50 (Che) (F) ko bo 65

- 1s

In and in: and in o in in in in and in: s schi 6) 2

Kk o F eE her in so « de

BZ, 7, B, 85 in and 8 are as defined above - 112 means chlorine or bromine, introduced into the reaction with compounds of the formula (1) in 12-vn (PP) - c where » 272 means the following group (B)

Kk -I sh" (ee) (95)

Ge or in de

VU, VO and K are as defined above in the presence of inert solvents and, if appropriate, in the presence of an acid-binding reagent. o Tetrazole derivatives of formula (I) represented by this invention show more significant herbicidal activity than the compounds described in the above-mentioned documents relating to the prior art.

In the formulas: in "Halogen" means fluorine, chlorine, bromine or iodine, and preferably means fluorine, chlorine or bromine. "Alkyl" can be straight chain or branched and examples include methyl, ethyl, n- and isopropyl, n-, iso-, sec- and tert-butyl, n-, iso-, neo- and tert-pentyl, n- and isohexyl. "Cycloalkyl" includes cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. These cycloalkyls may optionally contain as substituents halogen (for example, fluorine, chlorine, bromine, etc.), C 1-3 -alkyl (for example, methyl, 65 ethyl n- or isopropyl, etc.), and in the case of the presence of several substitutes, they can be the same or different. Specific examples of such substituted cycloalkyls include 1-methylcyclopropyl,

1-ethylcyclopropyl, 1-n-propylcyclopropyl, 1-methyl-2-fluorocyclopropyl, 2-methylcyclopropyl, 2-fluorocyclopropyl, 1-methyl-2,2-difluorocyclopropyl, 1-methyl-2,2-dichlorocyclopropyl, 2,2- difluorocyclopropyl, 2-methylcyclopentyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 2,6-dimethylcyclohexyl and 2,5-dimethylcyclohexyl.

Examples of "alkenyl" include vinyl, allyl, 1-methylallyl, 1,1-dimethylallyl and 2-butenyl. "Haloalkyl" means straight-chain or branched-chain alkyl in which at least one hydrogen atom is replaced by a halogen, and can be specified, for example, C..-alkyl containing 1-6 fluorine and/or chlorine atoms as substituents , more specifically, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, dichloromethyl, 7/0. 2-chloro-1,1,2-trifluoroethyl, 3-fluoropropyl, 3-chloropropyl, 2,2,3,3,3-pentafluoropropyl and 1,2,2,3,3,3-hexafluoropropyl.

The haloalkyl moiety of "haloalkyl" may mean the same as "haloalkyl" above, and "haloalkyl" may include, for example, difluoromethoxy, trifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromomethoxy, 2,2,2 -trifluoroethoxyl and 3-chloropropoxyl. "Alkylsulfonyl" means the group alkyl-5O2-, where the alkyl moiety means the same as above, and in particular 7/5 Includes methylsulfonyl, ethylsulfonyl, n- and isopropylsulfonyl.

Preferable values for formula (I) can be specified:

B' preferably means fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxyl, ethoxyl,

C, o-haloalkyl, methylthioyl, ethylthioyl, methylsulfonyl, ethylsulfonyl, methylsulfonyloxyl, ethylsulfonyloxyl, nitro- or cyano group, 22 preferably means C1-C3-alkyl, cyclopropyl, which may optionally contain fluorine, chlorine, methyl as substituents or ethyl, C..3-haloalkyl, C.sub.1-alkenyl or phenyl, which may optionally contain fluorine, chlorine, methyl, ethyl, trifluoromethyl or a nitro group as substituents, t is preferably equal to 1 or 2, n is preferably equal to 1 or 2, with 2? preferably means a hydrogen atom, fluorine, chlorine, methyl, ethyl or trifluoromethyl, o

WO preferably means methyl or ethyl,

B"! mainly means chlorine or bromine,

K is preferably equal to 1. б» зо As more preferable values of the radicals for formula (I) can be indicated:

IN! more preferably means chlorine, bromine, methyl or methylsulfonyl, co

B2 more preferably means methyl, ethyl, n-propyl, isopropyl or cyclopropyl, so t is more preferably equal to 2 and in this case the two BK substituents are connected respectively in position 2 and in "position 4 of the benzene ring, and these two substituents EE! can be the same or different, n is more preferably equal to 1.

In the most preferred group of compounds corresponding to this invention, the group

IN

М M - ' -(Сн3 5 из 7 М ч is attached in position З (according to formula (I)) of the benzene cycle. -i In the other most preferred group of compounds, the group О means one of the following groups: и» о; (ee) (95) iChe) 5 ime) o 60 b5 o or i 10 o or 15 2 shkh,

Substituents of different degrees of preference can be combined with each other without any restrictions.

However, compounds of the formula (I) in which the substituents 25 have the above-mentioned preferred values can clearly be indicated as a preferred group of compounds, and compounds of the formula (I) in which the substituents have the indicated values can be clearly indicated as a more preferred group of compounds above are more preferable values. at

The above method of obtaining (a) can be illustrated by the following reaction scheme in the case of using as a starting substance, for example, 33-oxo-1-cyclohexenyl-2,4-dichloro-3-(Z(1-methyl-1H-tetrazole-5 -yl)-thio|-methyl)-benzoate. b» » o as sn, p

St M. M so o o "v - I with 35 M M i - 40 | C ; Z - o s M... tcyanide CH m : M 5-X i » more mM nasnova

В. о, СИ ве The above-mentioned method of obtaining (B) can be illustrated by the following reaction scheme in the case

Go! use as a starting material, for example, 2-2,4-dichloro-3-((1-methyl-1H-tetrazol-5-yl)-thio|-methyl)-benzoyl)-cyclohexane-1,3-dione, and as a chlorinating reagent, for example, oxalyl chloride. 3e)

Ф) име) 60 b5 sn, opa her shk

THEM

M tea o si SN, so s

M. and | dream m

The above method of obtaining (c) can be illustrated by the following reaction scheme in the case of using as a starting substance, for example, 3-chloro-2-2,4-dichloro-3-S(1-methyl-1

N-tetrazol-5-yl)-thio|-methyl)-benzoyl)-2-cyclohexen-1-one and thiophenol.

CH, ch with vo | at

M dream M 5 ke And I

I (22) 7 with so o what, so « m. sn, with o V p

M - « cosnova SN, M 4.4 14- . ve h m sho -- ---- - M7 a o si

In addition, it is noted that the group (0-1) indicated as the value for 0 in the above formula (I) can also exist in the following two tautomeric forms Щ» (ee) о 50 3e)

F) name) 60 b5 in on vo

Ia. and where (18) 70 things! in or

Kk; ko v" y y on / (0-13. or s du On o v! is (22)

I a s de (18) « or - o c. h shi s y khz" k on

And yes? to (0-13. ш- It is also noted that the group (0-2) indicated as the value for C) in the above formula (I) can also exist in the following two tautomeric forms (ee) about 50 and Che)

F) ime) 60 b5 and ov

Kk to o still (0-28) 7 k or o 4

Oh no

Kk on 5 e ;

Kk (0-28. or s only (o)

Kk I (22) c

And so on (0-28)

In s k « zh or m o 4 in « shi s i

I Kk on "» 5

Kk t

Kk (0-25). -AND

Thus, the compounds of formula (I) corresponding to this invention include compounds of formula (I) in which t means the above-mentioned tautomeric groups (0-1a), (0-15), (0-2a) or ( 0-25) as groups 0-1 and 0-2, respectively.

Go! However, it should be understood that in the description of this invention, unless otherwise indicated, these tautomeric groups are given to illustrate group (0-1) or group (0-2). o Compounds of formula (II), the starting materials for the above method of preparation (a), are also new

Ge) compounds that have not been described in the literature so far, and they can be obtained in accordance with the methods described in various publications | for example, in the publications of Japanese patent applications Mo222/1990, Mo173/1990,

Mob425/1990, etc. by introducing the compound of the formula (IM) 2 o Hn (F) (83

RA

Pe) M -- t 60 (sna s; xx M

Who is

M where

B, B, t and n are as defined above and 65 M is halogen, in the reaction with compounds of formula (M)

sa-n (M) de

Oda means one of the following groups 13 0

Kk 4

KE their t o (0-)

A and nk or o « k v s

EE o / (0-23 (8)

Kk 7: k or o Ge! vi so in: so « h. v. so (0-)

And that

Kk "shi s or ;" о и к -И и- 2 и о (0-2) (ee) no 7 syu 70 V (Che) where 23, 7, v", Vb, v and 28 are as defined above, in an acceptable solvent, for example, dichloromethane, in the presence of an acceptable condensing reagent, eg, triethylamine. o The compounds of the formula (IM) used in the above reactions are also new compounds that have not been described in the literature so far, and they can be obtained, for example, by the reaction of the compounds of the formula (MI) ime) 2 and their

AND

60 (Z, n E (sna VX 3; le 7 b5 de

B", B, t and n are as defined above with a halogenating reagent, for example, phosphorus oxychloride, phosphorus oxybromide, phosphorus trichloride, phosphorus tribromide, phosgene, oxalyl dichloride, thionyl chloride, thionyl bromide.

The compounds of formula (M) used as starting materials in the preparation of compounds of the above formula (II) are known per se and are commercially available or can be easily prepared according to the methods described in various publications (for example, in the publications of patent applications of Japan Mob425/1990, Mo265415/1998,

Mo265441/19981).

The compounds of the formula (MI) used in the preparation of the compounds of the above formula (IM) are also 70 new compounds that have not been described in the literature so far, and they can be easily obtained, for example, by hydrolysis of the compounds of the formula (MI) "and

Y (8) y t M M (dreams (U

M Hn where

B, B, t and n are as defined above, and t2 is C 1 -C 6 -alkyl, preferably methoxy or ethoxy, in a suitable solvent, for example, in an aqueous solution of dioxane in the presence of a suitable base, for example, sodium hydroxide. Ha

The compounds of the above formula (MI) are also new compounds and can be easily obtained, for example, by the reaction of compounds of the formula (MI) and 9) in?

F m so - and; (She has non-K. 1 h

M IM eat- where

B2 is as defined above with compounds of formula (IX)

B, t and n are as defined above, and t? ! is C 1-6 -alkyl, preferably methyl or ethyl, and (ee) M is halogen, in a suitable solvent, for example, M,M-dimethylformamide, in the presence of a suitable condensing reagent, for example, potassium carbonate.

The compounds of the above formula (MI) are known compounds described, for example, in (Vegispie Moi!.28, iChe) p.74-76 (1895)) and they can be easily obtained in accordance with the methods described in this publication.

On the other hand, compounds of the above-mentioned formula (IX), some of which are new compounds that have not been described in the literature so far, can be easily obtained in accordance with the method described, for example, in (publication of Japanese patent application Mo173/1990)1.

Compounds of the formula (II), the starting materials in the above-mentioned production method (a), can also be easily obtained from the compounds of the above-mentioned formula (MI) in accordance with the method described, for example, in MO no. 93/180311.

As typical examples of compounds of the formula (II), used as starting substances in the above-mentioned production method (a), the following can be indicated: 33-oxo-1-cyclohexenyl-2-7(1-methyl-1H-tetrazole-5- yl)-thio|-methyl)-benzoate, 3Z-oxo-1-cyclohexenyl-2-(1-cyclopropyl-1H-tetrazol-5-yl)-thio|-methyl)-4-fluorobenzoate, 3Z-oxo- 1-cyclohexenyl-4-chloro-2-1(1-methyl-1H-tetrazol-5-yl)-thio|-methyl)-benzoate, 33-oxo-1-cyclohexenyl-4-chloro-2-1(1 -ethyl-1H-tetrazol-5-yl)-thio|-methyl)-benzoate, 65 Z-oxo-1-cyclohexenyl-4-chloro-2-1(1-cyclopropyl-1H-tetrazol-5-yl)- thio|-methyl)-benzoate, 33-oxo-1-cyclohexenyl-2-bromo-4-S(1-methyl-1H-tetrazol-5-yl)-thio|-methyl)-benzoate,

3Z-oxo-1-cyclohexenyl-4-bromo-2-S(1-phenyl-1H-tetrazol-5-yl)-thio|-methyl)-benzoate, 3Z-oxo-1-cyclohexenyl-2-7(1 -methyl-1H-tetrazol-5-yl)-thio[-methyl)-4-trifluoromethylbenzoate,

3-oxo-1-cyclohexenyl-2-4(1-methyl-1H-tetrazol-5-yl)-thio|-methyl)-4-methylbenzoate, 33-oxo-1-cyclohexenyl-2,4-dichloro-3 -((1-methyl-1H-tetrazol-5-yl)-thio|-methyl)-benzoate, 33-oxo-1-cyclohexenyl-2,4-dichloro-3-((1-cyclopropyl-1H-tetrazol- 5-yl)-thio[-methyl)-benzoate,

3-oxo-1-cyclohexenyl-2,4-dichloro-3-1(1-(2-chlorophenyl)-1H-tetrazol-5-yl)-thio|-methyl)-benzoate, 33-oxo-1-cyclohexenyl -2-chloro-3-S1(1-methyl-1H-tetrazol-5-yl)-thio|-methyl)-4-methylsulfonylbenzoate, 33-oxo-1-cyclohexenyl-2-chloro-3-1(1- cyclopropyl-1H-tetrazol-5-yl)-thio|-methyl)-4-methylsulfonylbenzoate, 70 3Z-oxo-1-cyclohexenyl-2-chloro-3-1(1-(n-pentyl)-1H-tetrazole- 5-yl)-thio[-methyl)-4-methylsulfonylbenzoate,

3-oxo-1-cyclohexenyl-2-chloro-3-1(1-(3-difluoromethylphenyl)-IN-tetrazol-5-yl)-thio|-methyl)-4-methylsulfonylbenzoate, 33-oxo-1- cyclohexenyl-4-chloro-3-Sh1(1-methyl-1H-tetrazol-5-yl)-thio|-methyl)-2-methylsulfonylbenzoate, 33-oxo-1-cyclohexenyl-2,4-dimethylsulfonyl-3-Sh (1-Methyl-1H-tetrazol-5-yl)-thio|-methyl)-benzoate, 33-oxo-1-cyclohexenyl-4-chloro-3-H1(1-methyl-1H-tetrazol-5-yl) -thio|-methyl)-2-methylsulfonylbenzoate, 3Z-oxo-1-cyclohexenyl-2-chloro-4-Х1(1-methyl-1H-tetrazol-5-yl)-thio|-methyl)-benzoate, 3Z- oxo-1-cyclohexenyl-4-4(1-methyl-1H-tetrazol-5-yl)-thio|-methyl)-2-methoxybenzoate, 3Z-oxo-1-cyclohexenyl-4-4(1-methyl-1H -tetrazol-5-yl)-thio|-methyl)-2-methylsulfonyloxybenzoate, 33-oxo-1-cyclohexenyl-4-4(1-methyl-1H-tetrazol-5-yl)-thio|-methyl)-2 -nitrobenzoate, 3Z-oxo-1-cyclohexenyl-4-4(1-ethyl-1H-tetrazol-5-yl)-thio|-methyl)-2-nitrobenzoate, 5,5-dimethyl-3-oxo-1- cyclohexenyl-2-1(1-methyl-1H-tetrazol-5-yl)-thio|-methyl)-4-trifluoromethylbenzoate, 4,4-dimethyl-3-oxo-1-cyclohexenyl-2-bromo-4-4 (1-methyl-1H-tetrazole-5- yl)-thio|-methyl)-benzoate, 4,4-dimethyl-3-oxo-1-cyclohexenyl-2,4-dichloro-3-S(1-methyl-1H-tetrazol-5-yl)-thio| -methyl)-benzoate, 4-(4-chloro-2-H1-methyl-1H-tetrazol-5-yl)-thio|-methyl)-benzoyloxy)-bicyclo!/3.2.11-3-octen-2- 4-22,4-dichloro-3-(0(1-cyclopropyl-1H-tetrazol-5-yl)-thio|-methyl)-benzoyloxy)-bicyclo!/3.2.11-3-octene-2 -one, 4-(2-chloro-3-D(1-cyclopropyl-1H-tetrazol-5-yl)-thio|-methyl)-4-methylsulfonylbenzoyloxy)-bicyclo|3.2.11-3-0 i) ktene -2-on.

As typical examples of compounds of the formula (IM), which are used as starting substances in the preparation of the compounds of the above-mentioned formula (II), the following can be indicated: Ge! zo 4-chloro-2-C1(1-methyl-1H-tetrazol-5-yl)-thio|-methyl)-benzoyl chloride, 4-bromo-2-S(1-cyclopropyl-1H-tetrazol-5-yl) -thio|-methyl)-benzoyl chloride, o 2-S(1-methyl-1H-tetrazol-5-yl)-thio|1-methyl)-4-trifluoromethylbenzoyl chloride, so 2,4-dichloro-3-S(1 -methyl-1H-tetrazol-5-yl)-thio|-methyl)-benzoyl chloride, 2,4-dichloro-3-S(1-cyclopropyl-1H-tetrazol-5-yl)-thio|-methyl)-benzoyl chloride , « 2-chloro-3-4(1-methyl-1H-tetrazol-5-yl)-thio|-methyl)-4-methylsulfonylbenzoyl chloride, i- 2-chloro-3-4(1-cyclopropyl-1H-tetrazole -5-yl)-thio|-methyl)-4-methylsulfonylbenzoyl chloride, 2-chloro-4-4(1-methyl-1H-tetrazol-5-yl)-thio|-methyl)-benzoyl chloride, 2-bromo-4 -Ш(1-methyl-1H-tetrazol-5-yl)-thio|-methyl)-benzoyl chloride, 4-Ш((1-methyl-1H-tetrazol-5-yl)-thio|-methyl)-2- nitrobenzoyl chloride, « 2,4-dichloro-3-S(1-methyl-1H-tetrazol-5-yl)-thio|-methyl)-benzoyl bromide, with c 2-chloro-3-4(1-methyl-1H- Tetrazol-5-yl)-thio|-methyl)-4-methylsulfonylbenzoyl bromide, . 2-chloro-3-4(1-cyclopropyl-1H-tetrazol-5-yl)-thio|-methyl)-4-methylsulfonylbenzoyl bromide. and?" As typical examples of compounds of the formula (MI), which are used as starting substances in the preparation of compounds of the above-mentioned formula (IM), it is possible to specify: 4-chloro-2-1(1-methyl-1H-tetrazol-5-yl)-thio| -methyl)-benzoic acid, -I 4-bromo-2-4(1-cyclopropyl-1H-tetrazol-5-yl)-thio|-methyl)-benzoic acid, 2-((1-methyl-1H-tetrazole -5-yl)-thio|-methyl)-4-trifluoromethylbenzoic acid, and 2,4-dichloro-3-S(1-methyl-1H-tetrazol-5-yl)-thio|-methyl)-benzoic acid,

Go! 2,4-dichloro-3-S(1-cyclopropyl-1H-tetrazol-5-yl)-thio|-methyl)-benzoic acid, 2-chloro-3-4(1-methyl-1H-tetrazol-5-yl )-thio|-methyl)-4-methylsulfonylbenzoic acid, o 2-chloro-3-4(1-cyclopropyl-1H-tetrazol-5-yl)-thio|-methyl)-4-methylsulfonylbenzoic acid,

Ge) 2-chloro-4-4(1-methyl-1H-tetrazol-5-yl)-thio|-methyl)-benzoic acid, 2-bromo-4-4(1-methyl-1H-tetrazol-5- yl)-thio|-methyl)-benzoic acid, 4-S((1-methyl-1H-tetrazol-5-yl)-thio|-methyl)-2-nitrobenzoic acid.

As typical examples of compounds of the formula (MI), which are used as starting substances in the preparation of compounds of the above-mentioned formula (MI), the following can be indicated:

F) methyl-4-chloro-2-C(1-methyl-1H-tetrazol-5-yl)-thio|-methyl)-benzoate, ka methyl-4-bromo-2-1(1-cyclopropyl-1H- Tetrazol-5-yl)-thio|-methyl)-benzoate, methyl-2-S(1-methyl-1H-tetrazol-5-yl)-thio|-methyl)-4-trifluoromethylbenzoate, in methyl-2,4 -dichloro-3-1(1-methyl-1H-tetrazol-5-yl)-thio|-methyl)-benzoate, methyl-2,4-dichloro-3-1(1-cyclopropyl-1H-tetrazol-5- yl)-thio|-methyl)-benzoate, methyl-2-chloro-3-S(1-methyl-1H-tetrazol-5-yl)-thio|-methyl)-4-methylsulfonylbenzoate, methyl-2-chloro- 3-S(1-cyclopropyl-1H-tetrazol-5-yl)-thio|-methyl)-4-methylsulfonylbenzaoate, methyl-2-chloro-4-S(1-methyl-1H-tetrazol-5-yl)- thio|-methyl)-benzoate, 65 methyl-2-bromo-4--(1-methyl-1H-tetrazol-5-yl)-thio|-methyl)-benzoate, methyl-4-4(1-methyl- 1H-tetrazol-5-yl)-thio[-methyl)-2-nitrobenzoate,

ethyl-2,4-dichloro-3-S(1-methyl-1H-tetrazol-5-yl)-thio|-methyl)-benzoate, ethyl-2-chloro-3-1(1-methyl-1H-tetrazole -5-yl)-thio|-methyl)-4-methylsulfonylbenzoate, ethyl 2-chloro-3-((1-cyclopropyl-1H-tetrazol-5-yl)-thio|-methyl)-4-methylsulfonylbenzoate.

Compounds of formula (IB), the starting materials for the above-mentioned production method (p), are among the compounds of formula (I) corresponding to this invention, and they can be easily obtained according to the above-mentioned method (a).

As typical examples of compounds of the formula (IB) used as starting substances in the above-mentioned production method (B), the following can be indicated, which are included in the number of compounds of the formula (1): 70 2-(4-chloro-2-(1- methyl-1H-tetrazol-5-yl)-thio|-methyl)-benzoyl)-cyclohexane-1,3-dione, 2-(4-bromo-2-S(1-cyclopropyl-1H-tetrazol-5-yl) )-thio|-methyl)-benzoyl)-cyclohexane-1,3-dione, 2-2-X1(1-methyl-1H-tetrazol-5-yl)-thio|-methyl)-4-trifluoromethylbenzoyl)-cyclohexane -1,3-dione, 2-2,4-dichloro-3-((1-methyl-1H-tetrazol-5-yl)-thio|-methyl)-benzoyl)-cyclohexane-1,3-dione, 2 -2,4-dichloro-3-1(1-cyclopropyl-1H-tetrazol-5-yl)-thio|-methyl)-benzoyl)-cyclohexane-1,3-dione, 2-(2-chloro-3- (1-methyl-1H-tetrazol-5-yl)-thio|-methyl)-4-methylsulfonylbenzoyl)-cyclohexane-1,3-dione, 2-(2-chloro-3-(1-cyclopropyl-1H-tetrazole) -5-yl)-thio|-methyl)-4-methylsulfonylbenzoyl)-cyclohexane-1,3-dione, 2-(2-chloro-4-(1-methyl-1H-tetrazol-5-yl)-thio| -methyl)-benzoyl)-cyclohexane-1,3-dione, 2-(2-bromo-4-S(1-methyl-1H-tetrazol-5-yl)-thio|-methyl)-benzoyl)-cyclohexane- 1,3-dione, 2-A-Sh1 (1-methyl-1H-tetrazol-5-yl)-thio|-methyl)-2-nitrobenzoyl)-cyclohexane-1,3-dione, 3-12-chloro-3-S(1-cyclopropyl-1H-tetrazole -5-yl)-thio|-methyl)-4-methylsulfonylbenzoyl)-bicyclo|3.2.1|octane-2, 4-dione.

As halogenating reagents used in the reaction with compounds of the formula (IB) in the preparation method (B), it is possible to specify, for example, thionyl chloride, thionyl bromide, oxalyl dichloride, oxalyl dibromide, etc.

Compounds of the formula (Ic), the starting materials for the above-mentioned method of preparation (c), are included in the number of compounds of the formula (I) corresponding to this invention, and they can be easily obtained according to the above-mentioned method (b). and)

As typical examples of compounds of the formula (Ic) used as starting substances in the above-mentioned production method (c), the following can be indicated, which are included in the number of compounds of the formula (1):

3-chloro-2-14-chloro-2-((1-methyl-1H-tetrazol-5-yl)-thio|-methyl)-benzoyl)-2-cyclohexen-1-one, Ge! zo 3-chloro-2-(4-bromo-2-1(1-cyclopropyl-1H-tetrazol-5-yl)-thio|-methyl)-benzoyl)-2-cyclohexen-1-one,

3-chloro-2-42-S(1-methyl-1H-tetrazol-5-yl)-thio|-methyl)-4-trifluoromethylbenzoyl)-2-cyclohexen-1-one, o

3-chloro-2-12,4-dichloro-3-S(1-methyl-1H-tetrazol-5-yl)-thio|-methyl)-benzoyl)-2-cyclohexen-1-one, so

3-chloro-2-12,4-dichloro-3-S(1-cyclopropyl-1H-tetrazol-5-yl)-thio|-methyl)-benzoyl)-2-cyclohexen-1-one,

3-chloro-2-12-chloro-3-11(1-methyl-1H-tetrazol-5-yl)-thio|-methyl)-4-methylsulfonylbenzoyl)-2-cyclohexen-1-one, "

3-chloro-2-12-chloro-3-((1-cyclopropyl-1H-tetrazol-5-yl)-thio|-methyl)-4-methylsulfonylbenzoyl)-2-cyclohexen-1-one,

3-chloro-2-12-chloro-4-((1-methyl-1H-tetrazol-5-yl)-thio|-methyl)-benzoyl)-2-cyclohexen-1-one,

3-Chloro-2-yl2-bromo-4-1(1-methyl-1H-tetrazol-5-yl)-thio|-methyl)-benzoyl)-2-cyclohexen-1-one,

3-chloro-2-14-S(1-methyl-1H-tetrazol-5-yl)-thio|-methyl)-2-nitrobenzoyl)-2-cyclohexen-1-one, « 4-chloro-2-2 -chloro-3-S(1-cyclopropyl-1H-tetrazol-5-yl)-thio|-methyl)-4-methylsulfonylbenzoyl)-bicyclo|3.2.11- z c 3-octen-2-one. . Compounds of formula (II), the starting materials for the above-mentioned production method (c), are thiols and compounds well-known in organic chemistry, and as typical examples of compounds of formula (II) the following can be indicated: methyl mercaptan, ethyl mercaptan, -I thiophenol, 4-fluorothiophenol, and 4-chlorothiophenol,

Go! 2-methylthiophenol, 4-ethylthiophenol, o 4-trifluoromethylthiophenol, etc.

Ge) All compounds of formulas (I), (M). (MI) and (MI) used in the above-mentioned methods (a)-(c) as starting substances or intermediate products for obtaining compounds of formula (I) corresponding to this invention are new compounds that have not been described in literature Together, these compounds can be described by the following General structural formula (X) in

F) o and yu (vd vom r -Yasnu,-8-5y

NOT m7 M de

MU means T", hydroxyl or 12, where B", c, t, n, T", T2 and M are as defined above.

The reactions of the above preparation method (a) can be carried out in an acceptable solvent. Examples of such solvents include aliphatic, alicyclic, and aromatic hydrocarbons (which may optionally be chlorinated), for example, toluene, dichloromethane, chloroform, and 1,2-dichloroethane; ethers, for example, ethyl ether, dimethoxyethane (DME) and tetrahydrofuran (THF); ketones, for example, methyl isobutyl ketone (MIBK); nitriles, for example, acetonitrile; esters, for example, ethyl acetate; acid amides, for example, dimethylformamide (DMF).

The method of preparation (a) can be carried out in the presence of cyanide and a base. Examples of cyanide suitable for use in this case include sodium cyanide, potassium cyanide, acetone cyanohydrin, and hydrogen cyanide. As a base, you can specify, for example, as inorganic bases - hydroxides and carbonates of alkali metals and alkaline earth metals, for example, sodium carbonate, potassium carbonate, lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide; and as organic bases - tertiary amines, dialkylaminoanilines and pyridines, for example, triethylamine, pyridine, 4-dimethylaminopyridine (DMAP), 1,4-diazabicyclo|2,2,2)octane (DABCO) and 1,8-diazabicyclo|5, 4, Fundets-7-en (DBU).

The above method of obtaining (a) can also be carried out in the simultaneous presence of an interphase catalyst. Examples of an interfacial catalyst suitable for use in this case include crown ethers such as dibenzo-18-crown-6, 18-crown-6b and 15-crown-5.

The reaction of the above method of preparation (a) can be carried out in a fairly wide range of temperatures

Acceptable temperatures typically range from about -10°C to about 80°C, preferably from about 5°C to about 409°C. The specified reactions are preferably carried out at normal pressure. However, it is not necessary that they can be carried out at elevated or reduced pressure.

When carrying out the preparation method (a) in the case when C) means groups (0-1) or (0-2), the desired compounds of the above formula (I) can be obtained, for example, by reacting 1 mol of the compound of formula (I) with 1-4 mol. triethylamine in a solvent, for example, in acetonitrile, in the presence of 0.01 to 0.5 mol. cyanohydrin of acetone. Ha

When carrying out the method of obtaining (a), compounds of formula (I) can be obtained by carrying out reactions, starting from compounds of the above formula (MI), continuously in one vessel without separating compounds of formulas i) (M) 1 (B.

The reaction of the above preparation method (B) can be carried out in an acceptable solvent. Examples of such solvents include aliphatic, alicyclic, and aromatic hydrocarbons (which may optionally be chlorinated), for example, pentane, hexane, cyclohexane, petroleum ether, naphtha, benzene, toluene, xylene, dichloromethane, chloroform, carbon tetrachloride , 1,2-dichloroethane | chlorobenzene, ethers, for example, ethyl ether, methyl ethyl ether, isopropyl ether, butyl ether, dioxane, dimethoxyethane (DME), sb tetrahydrofuran (THF) and diethylene glycol dimethyl ether (DGM), ketones, for example, acetone, methyl ethyl ketone (MEK), methyl isopropyl ketone and methyl isobutyl ketone (MIBK), nitriles, for example, acetonitrile | propionitrile, with complex esters, for example, ethyl acetate | amyl acetate, acid amides, for example, dimethylformamide (DMF), h-dimethylacetamide (DMA), M-methylpyrrolidone, 1,3-dimethyl-2-imschazolinone and hexamethylphosphoric acid triamide (THMFC).

The reaction of the above method of preparation (B) can be carried out in a fairly wide range of temperatures. Acceptable temperatures usually range from about -20 to about 100°C, 70 preferably from about 0 to about 50°C. These reactions are preferably carried out at normal pressure. - c However, it is not necessary for them to be carried out at increased pressure or at reduced pressure. a When implementing the method of obtaining (p) in the case when O means groups (0-6) or (0-7), and in the above-mentioned group B! means chlorine or bromine, the desired compounds of the above formula (I) can be obtained, for example, by the reaction of tmol. compounds of formula (IB) with 1-bmol. oxalyl dichloride in a solvent, for example, in dichloromethane. and Reactions of the above preparation method (c) can be carried out in an acceptable solvent. Examples of such solvents include aliphatic, alicyclic, and aromatic hydrocarbons (which may optionally be chlorinated), for example, pentane, hexane, cyclohexane, petroleum ether, naphtha, benzene, toluene, xylene, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene | dichlorobenzene, ethers, c 250 e.g. ethyl ether, methyl ethyl ether, isopropyl ether, butyl ether, dioxane, dimethoxyethane (DME), tetrahydrofuran (THF) and diethylene glycol dimethyl ether (DGM), ketones e.g. acetone,

Me; methyl ethyl ketone (MEK), methyl isopropyl ketone | methyl isobutyl ketone (MYBK), nitriles, for example, acetonitrile, propionitrile | acrylonitrile, esters, for example, ethyl acetate and amyl acetate, acid amides, for example, dimethylformamide (DMF), dimethylacetamide (DMA) and M-methylpyrrolidone, sulfones | sulfoxides, for example, dimethyl sulfoxide (DMSO) and sulfolane, bases, for example, pyridine.

GF! The method of preparation (c) can be carried out in the presence of a condensing reagent. As a suitable condensing reagent, it is possible to specify, for example, inorganic bases - hydrides and carbonates of alkaline metals, for example, sodium hydride, lithium hydride, sodium carbonate | potassium carbonate, and as organic bases - tertiary amines, dialkylaminoanilines and pyridines, for example, triethylamine, 60 1,1,4,4-tetramethylethylenediamine (TMEDA), pyridine, 4-dimethylaminopyridine (DMAP), 1,4-diazabicyclo|2.2. 2) octane (DABCO) and 1,8-diazabicyclo|5,4,Fundec-7-ene (DBU).

The reaction of the production method (c) can be carried out in a fairly wide range of temperatures. Acceptable temperatures are usually in the range from about -20 to about 140 oC, preferably from about 0 to about 1002. The indicated reactions are preferably carried out at normal pressure. However, it is not necessary that they can be carried out at increased pressure or at reduced pressure.

When carrying out the production method (c) in the case when 0 means groups (0-3), (0-4) or (0-5), the desired compounds of the above formula (I) can be obtained, for example, by the reaction of tTmol. compounds of formula (Ic) with 1-Bmol. thiophenol in the presence of 1 to 5 mol. triethylamine.

The active compounds of the above formula (I) corresponding to the present invention show, as shown in the biological test examples described below, excellent herbicidal activity against various weeds and can be used as herbicides. In the presented description, weeds mean, in the broadest sense, all plants that grow in places where they are undesirable. The compounds corresponding to this invention, depending on the concentration of the applied agent, act as general-killing herbicides or as selective herbicides. 7/0 Active compounds corresponding to this invention can be applied, for example, to the following weeds and crops.

Dicotyledonous weeds of the genera: Zipariv, I eridisht, Site, 5(eMyapa, Speporodisht, Opisa, Zepesio, Atagapiyivs,

Rogishasa, Hapipisht, Irotoea, Roiudopyt, Atrbgovzia, Sigvisht, Zopspyv, ZoYiapyt, Kogirra, IGatisht, Megopisa,

Bashga, Mioia, SaiIorziz, Rarameg, Sepiatsgea, Saiipzoda, Koiaia, Iipdegpia, etc.

Dicotyledonous cultures of the genera: Sozzurisht, Siusipe, Veia, Juoasiv, RiiazeoYiv5, Rivit, ZoYapit, Igypit, Irotoea,

Misia, Misoiapa, I usoregvisop, Agaspiv, Vgazvisa, I asiisa, Sisytiv, Sysygoia, etc.

Monocotyledonous weeds of the genera: Espippospioa, Zeiagia, Rapisit, Oidinagia, Rpieiit, Roa, Reziisa, Eiezipe,

Yi oisht, Vgotiv, Amepa, Suregiz, Zogupyt, Adgorugop, Mopospogia, Ritrbgiviuiv, Zadiyapa, Eieospapv, Zsigriv,

RazraYisht, Izspaetit, Adgoviv, AIoresygiv, Supodop, etc.

Monocotyledonous crops of genera. Ogula, 7ea, Tpiistst, Nogdetst, Amepa, ZesaIie, Zoguoyit, Rapisit, Zasspagit,

Apapavz, Azragadiv, APit! TP

The use of the compounds corresponding to this invention is not limited to the crops mentioned above, and they can be used in the same way for other plants. Active compounds corresponding to this invention, depending on the concentration used, can indiscriminately destroy weeds and can be used, for example, on areas occupied by industrial enterprises, railway tracks, paths, with areas on which trees are planted or not planted. In addition, the active compounds according to the present invention can be used to kill weeds in plantings of perennial crops and can be used, i) for example, in forest plantations, plantings of ornamental trees, in orchards, in vineyards, in citrus orchards, in nut plantations , banana plantations, coffee and tea plantations, rubber plantations, oil palm plantations, cocoa plantations, berry plantations, hop plantations, etc. and they can also be brought Ge! zo for selective destruction of weeds on plantings of annual crops.

According to the invention, it is possible to process all plants and parts of plants. The term "plants" includes all plants and plant populations, such as useful and harmful wild plants and cultivated plants (including cultivated co-natural varieties). Cultivated plants can be varieties of plants obtained with the help of conventional selection and methods of optimization, or obtained with the help of methods of biotechnology and genetic engineering, or by "

With the help of a combination of such methods and techniques, including transgenic plants and including plant varieties that are impossible or possible to protect with patents on plants or plant varieties. Plant parts are all parts and organs of plants located below or above the soil surface, for example, shoots, leaves, needles, petioles and stems, trunks, flowers, fruits and seeds, as well as roots, tubers, bulbs and rhizomes. The term "plant" also includes harvested crops and planting material, such as petioles, corms, rhizomes, " 470 shoots and seeds. According to the invention, plants and plant parts are processed using conventional methods by applying active components or compositions containing them directly to plants or plant parts, or on their environment (including soil) or storage, for example, by immersion, spraying, dusting, aerosol irrigation, scattering, and in the case of planting material - by application

ONE or more layers. Active compounds corresponding to this invention can be prepared in the form of traditional compositions. Such compositions can be specified, for example, solutions, wettable powders, emulsions, suspensions, powders, granules that are dispersed in water, tablets, granules, concentrates in suspensions-emulsions, microcapsules in polymeric substances, bulk compositions, etc.

Go! These compositions can be prepared using known methods, for example, by mixing the active substance 50p with fillers, namely, with liquid or solid solvents or carriers and, optionally, with o surface-active substances, namely, emulsifiers and/or dispersants , and/or foaming agents.

Ge) As liquid solvents or carriers, you can specify, for example, aromatic hydrocarbons (for example, xylene, toluene, alkylnaphthalene, etc.), chlorinated aromatic and chlorinated aliphatic hydrocarbons (for example, chlorobenzenes, ethylene chlorides, methylene chloride, etc.), aliphatic hydrocarbons (for example, cyclohexane, etc. and paraffin waxes (for example, fractions of mineral oil, etc.)), alcohols (for example, butanol, glycol, etc.) and their ethers, complex esters, etc. .p., ketones (for example, acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone and

F) etc.), highly polar solvents (for example, dimethylformamide, dimethylsulfoxide, etc.) and water. If water is used as a diluent, then organic solvents can be used as auxiliary solvents. As solid diluents or carriers can be specified, for example, ground natural minerals (for example, kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite, diatomaceous earth, etc.), ground synthetic minerals (for example, highly dispersed silicic acid, aluminum oxide, silicates, etc.) etc. As solid carriers for granules, ground and fractionated rocks (for example, calcite, marble, pumice, sepiolite, dolomite, etc.), synthetic granules from inorganic and organic flour, crushed organic materials (for example, sawdust, coconut shell , rods of corn cobs and stalks of tobacco, etc.) etc. p.

As emulsifiers and/or foaming agents, you can specify, for example, nonionic and anionic emulsifiers (for example, esters of polyoxyethylene and fatty acids, ethers of polyoxyethylene and fatty alcohols, (for example, alkylarylpolyglycol ethers, alkyl sulfonates, aryl sulfates, aryl sulfonates, etc. ), albumin hydrolysis products, etc.

Dispersants include, for example, spent lignin sulfite alkali, methyl cellulose, etc.

In compositions (powders, granules, emulsions) you can use substances that add stickiness. As substances that add stickiness, you can specify, for example, carboxymethyl cellulose, natural and synthetic polymers (for example, gum arabic, polyvinyl alcohol, polyvinyl acetate, etc.). 70 Dyes can also be used. As specified dyes, inorganic pigments (for example, iron oxide, titanium oxide, Berlin azure, etc.) and organic dyes, such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and microfertilizers such as metal salts such as iron, manganese, boron, copper, cobalt, molybdenum, zinc, etc.

These compositions can contain an active compound of formula (I) usually in the range from 0.1 to 85 wt.v, preferably from 0.5 to 30 wt.v.

For weed control, active compounds of formula (I) corresponding to this invention can be used alone or in compositions. they can also be used as a reagent mixed with known herbicides. Such a miscible reagent can be pre-prepared as a ready-made composition or can be prepared as a tank mix for the case of use. As herbicides suitable for use in combination with compounds of formula (I) corresponding to this invention, as a mixing reagent, the following herbicides, for which the common names are given, can be particularly indicated.

Acetamide-type herbicides, for example, pretilachlor, butachlor, tenichlor, alachlor, etc.; amide-type herbicides, for example, clomeprop, etobenzanid, etc.; herbicides of the benzofuran type, for example, benfuresate, etc.; herbicides of the indandun type, for example, indanophan, etc.; (8) pyrazole-type herbicides, for example, pyrazolate, benzofenap, pyrazoxifene, etc.; oxazinone-type herbicides, for example, oxacyclomefon, etc.; herbicides of the sulfonylurea type, for example, bensulfuron-methyl, azimsulfuron, imazosulfuron, Ge! zo Pyrazosulfuron-ethyl, cyclosulfamron, ethoxysulfuron, halosulfuron (-methyl), etc.; herbicides of the thiocarbamate type, for example, thiobencarb, molinate, pyributycarb, etc.; o triazine-type herbicides, for example, dimethamethrin, symethrin, etc.; with herbicides of the triazole type, for example, cafenestrol, etc.; herbicides of the quinoline type, for example, quinclorac, etc.; « herbicides of the isoxazole type, for example, isoxaflutol, etc.; i- herbicides of the dithiophosphate type, for example, anilophos, etc.; herbicides of the oxyacetamide type, for example, mefenacet, flufenacet, etc.; herbicides of the tetrazolinone type, for example, fentrazamide, etc.; herbicides of the dicarboxyimide type, for example, pentoxazone, etc.; "trion-type herbicides, for example, sulcotrion, benzobicyclone, etc.; in c herbicides of the phenoxypropinate type, for example, cigalofop-butyl, etc.; herbicides of the benzoic acid type, for example, pyriminobac-methyl, etc.; ;" herbicides of the diphenyl ether type, for example, chlomethoxyfen, oxyfluorfen, etc.; herbicides of the pyridine dicarbotisate type, for example, dithiopyr, etc.; herbicides of the phenoxyl type, for example, MSRA, MURV, etc.; - And urea-type herbicides, for example, dimron, cumyluron, etc.; herbicides of the naphthalenedione type, for example, quinoclamine, etc.; pi herbicides of the isoxalidinone type, for example, clomazone, etc.;

Go! herbicides of the diphenyl ether type, for example, chlomethoxyfen, oxyfluorfen, etc.; herbicides of the pyridine dicarbotisate type, for example, dithiopyr, etc.; and herbicides of the phenoxyl type, for example, MSRA, MURV, etc.;

He herbicides of the urea type, for example, dimron, cumyluron, etc.;

In addition to the above herbicides, the following herbicides are used, for which common names are given, for example, acetochlor, acifluorfen (-sodium), aclonifen, alloxidim (-sodium), ov ametryn, amicarbazone, amidochlor, amidosulfuron, amitrole, azulam, atrazine, azafenidine , beflubutamide, benzaolin (-ethyl), bentazone, benzphendisone, benzoylprop (-ethyl), bialaphos, bifenox, bispyribac (-sodium),

F) bromacil, bromobutide, bromophenoxime, bromoxynil, butaphenacyl (-allyl), butenachlor, butralin, kabutroxidim, butylate, carbetamide, carfentrazone (-ethyl), chloramben, chloridazone, chlorimuron (-ethyl), chlornitrophen, chlorsulfuron, chlorthiamide, chlortoluron . desmedifam, diallate, dicamba, dichlobenil, dichlorprop (-P), diclofop (-methyl), diclosulam, diethyl (-ethyl), difenopenten (-ethyl), difenzoquat, diflufenican, diflufenzopyr, dikegulak (-sodium), dimefuron, dimepiperate, dimetachlor, dimethenamid (-P), dimexiflam, dinitramine, difenamide, diquat (-dibromide), diuron, epropodan, ERTS, esprocarb, etalfluralin, ethametsulfuron (-methyl), 65 ethiosin, etofumesate, ethoxyfen, fenoxaprop (-P-ethyl) , flamprop (-M-isopropyl, -M-methyl), fluzasulfuron, florazulam, fluazifop (-P-butyl), fluazolate, flucarbazone (-sodium), fluchl oralin, flumetsulam,

flumiclorac (-pentyl), flumioxazin, flumipropin, fluometuron, fluochloridone, fluoglycofen (-ethyl), flupoxam, flupropacil, flurpyrsulfuron (-methyl, -sodium), fluorenol (-butyl), fluridone, fluroxypyr (-butcosyprolyl, -meptyl), flurprimidol, flurtamone, fluthiacet (-methyl), fomezafen, foramsulfuron, glufosinate (-ammonium), glyphosate (-ammonium, -isopropylammonium), halosafen, haloxyfop (-ethoxyethyl, -P-methyl), hexazinone, imazametabenz (-methyl), imazametapyr, imazamox, imazapic, imazapyr, imazaquin, imazetapyr, iodosulfuron (-methyl, -sodium), ioxynil, isopropalin, isoproturon, isouron, isoxaben, isoxachlortol, isoxadifen (-ethyl), isoxapyrifop, ketospiradox, lactofen, lenacil, linuron, mecoprop (-P), mesotrione, metamiron, metazachlor, metabenzthiazuron, methyldimron, metobenzuron, metobromuron, (5-) metolachlor, 7/0 metosulam, metoxuron, metribuzin, metsulfuron (-methyl), monolinuron, naproanilide, napropamide, neburon, nicosulfuron, norflurazon, orbenkarb, oryzalin, oxadiargil, oxadiazo n, oxasulfuron, paraquat, pelargonic acid, pendimethalin, pendralin, pentoxamide, phenmedipham, picolinafen, piperofos, primisulfuron (-methyl), profluazol, profoxidim, promethrin, propachlor, propanil, propaquizafop, propisochlor, propoxycarbazone (-sodium), propizamide, prosulfocarb , prosulfuron, pyraflufen (-ethyl), 7/5 Pyrazogyl, pyribenzoxime, pyridafol, pyridate, pyridatol, pyrifthalide, pyrithiobac (-sodium), quinmerac, quizalofop (-P-ethyl, -P-tefuryl), rimsulfuron, cetoxydim, simazine , sulfentrazone, sulfometuron (-methyl), sulfosate, sulfosulfuron, tebutam, tebuthiuron, tepraloxidim, terbuthylazine, terbutrin, thiazopyr, thidiazimin, thifensulfuron (-methyl), thiocarbazil, tralcoxidim, triallate, triasulfuron, tribenuron (-methyl), triclopyr, tridiphan , trifloxysulfuron, trifluralin, triflusulfuron /(-methyl), 2o tritosulfuron.

The herbicides listed above are well-known herbicides given in the work |"Reziiside Mapia!" 2000, which was published by the University of Warsaw.

Mass ratios of groups of active substances in mixed compositions can vary within relatively wide limits. with

For example, on mass. h. (1) compounds of formula (I) are used from 0.2 to 14 wt. parts of herbicides of the acetamide type, (8) preferably - from 0.66 to 5 wt. h., from 2 to 4 Omas. h. herbicides of the amide type, preferably - from 3.96 to 1 bmas. h., Hey! from 0.2 to 2Omas. parts of herbicides of the benzofuran type, preferably - from 1.00 to bmas. h., and from 0.2 to mass. parts of herbicides of the indandione type, preferably from 0.49 to 2 wt. h., from 0.06 to 4 mass. part of herbicides of the oxazinone type, "preferably - from 0.20 to 0.wt. h., i- from 0.02 to 4 mass. h. herbicides of the sulfonylurea type, preferably - from 0.07 to 1.2 wt. h. from 1 to 10 Omas. parts of herbicides of the thiocarbamate type, preferably from 2.47 to 4 Omas. h., "from 0.6 to 12 mass. parts of herbicides of the triazine type, with c preferably - from 1.32 to 4.5 wt. h., from 0.1 to wt. parts of herbicides of the triazole type, with mostly - from 0.33 to Zmas. h., from 0.2 to 1 Omas. parts of herbicides of the dithiophosphate type, preferably - from 1.00 to 4 wt. h., -And from 0.2 to 5 Omas. h. herbicides of the oxyacetamide type, preferably - from 1.00 to 12 mass. h., pi from 0.02 to 1 Omas. parts of herbicides of the tetrazolinone type,

Go! mostly - from 0.17 to Zmas. h., from 0.1 to 12 mass. h. herbicides of the dicarboxyimide type, and preferably - from 0.33 to 4.5 wt. h.,

He) from 0.2 to 12 mass. parts of herbicides of the phenoxypropinate type, preferably - from 0.4 to 1, by weight. h., from 0.6 to 2 Omas. parts of herbicides of the diphenyl ether type, preferably - from 1.65 to 7.5 wt. h., from 0.02 to 14 mass. parts of herbicides of the pyridine dicarbothioate type, (F) preferably - from 0.20 to 5 wt. h.; ka from 0.2 to 1Omas. part of herbicides of the phenoxyl type, preferably - from 0.66 to 4 mass. h.; from 2 to 8 Omas. parts of urea-type herbicides, preferably from 4.95 to 25 wt. h

In addition, the active compounds of formula (I) according to the present invention can also be mixed with a detoxifier, and their use as selective herbicides can be expanded by reducing phytotoxicity and expanding the range of weeds to be destroyed by such mixing. 65 As an example of a detoxifier, the following detoxifiers can be indicated:

АО-67, ВА5-145138, benoxacor, cloquintocet (-mexyl), cyometrinil, 2,4-О0, OKA-24, dichlormid, dimron,

fenclorim, fenchlorazole (-ethyl), flurazole, fluxofenim, furilazole, isoxadifen (-ethyl), MSRA, mecoprop (-P), mefenpyr (-diethyl), MO-191, naphthoic anhydride, oxabetrinil, PPO-1292, K- 29148.

The above detoxifiers are well-known detoxifiers given in the work "Revziiside Mapia!" 2000, which was published by the University of Warsaw.

Mass ratios of groups of active substances in mixed compositions can vary within relatively wide limits.

For example, on mass. h. (1) compounds of formula (I) are used from 0.05 to 5Omas. parts of dichlormid, 70 preferably - from 0.1 to 1 Omas. h.;

Zb from 0.05 to 5Omas. h. dimron, preferably - from 0.1 to 1 Omas. h.; from 0.05 to 5Omas. part of fenclorim, preferably - from 0.1 to 1 Omas. h.; from 0.05 to 5Omas. parts of mefenpyr (-diethyl), preferably - from 0.1 to 1Omas. h.; from 0.05 to 5Omas. parts of naphthalene carboxylic acid anhydride, preferably from 0.1 to 1 mass. h

In addition, the combinations of the compounds of formula (I) corresponding to the present invention and the herbicides specified above can also be mixed with the detoxifiers specified above and their use as selective herbicides can be expanded by reducing phytotoxicity and expanding the spectrum of weeds to be destroyed. by adding a detoxifier and/or other selective herbicides.

Unexpectedly, it was found that for some mixed compositions corresponding to this invention, synergistic effects are found. high school

In the case of using active compounds of formula (I) and mixed compositions containing these compounds corresponding to this invention, they can be directly used as such or used in the form of constituent forms, such as ready-to-use solutions, emulsions, tablets, suspensions, powders, pastes, granules, or use in the form of forms prepared by further dilution. Active compounds corresponding to this invention can be applied, for example, by watering, sprinkling, spraying, by applying granules, etc.

Active compounds of formula (I) mixed compositions containing these compounds corresponding to this invention can be used at any stage before and after the start of plant growth, they can also be applied to the soil before sowing.

The introduced amount of active compounds of formula (I) and mixed compositions containing these compounds corresponding to this invention can vary in a fairly wide range and they fundamentally differ depending on the nature of the required effect. In the case of use as herbicides, the amount applied can be, for example, ranges from about 0.01 to about 3 kg, preferably from about 0.05 to about kg of active compounds per hectare.

The preparation and use of compounds and mixed compositions containing these compounds according to the present invention will be described in more detail with the help of the following examples. However, the present invention is not intended to be limited in any way to these examples. with" Synthesis example 1 p

WITH

Я5.Ф0.9 es Te za t Z - ! so - o 50 M o o o,sn, 33-oxo-1-cyclohexenyl-2-chloro-3-Sh1(1-ethyl-1H-tetrazol-5-yl)-thio|-methyl)-4-methylsulfonylbenzoate ( 0.83 g) is dissolved in acetonitrile (200 ml) and triethylamine (0.35 g) and acetone cyanohydrin (1 g) are added to it and the mixture 22 Bg is stirred at room temperature. After distilling off the solvent, the mixture is acidified by addition

HF) of dilute hydrochloric acid and extracted with dichloromethane (1500 ml). The organic layer is washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. Dichloromethane is distilled off and 2-(2-chloro-3-(1-ethyl-1H-tetrazol-5-yl)-thio|-methyl)-4-methylsulfonylbenzoyl)-cyclohexane-1,3-dione (0.75 g ). 60 Melting point (m.p.): 67-71.

An example of the synthesis of 2 b5 c o c siz sia M z 2 M h 8-X mi G" zhii m i o З0.СсН gi З

To a solution of 2-(2-chloro-4-methylsulfonyl-3-S(1-methyl-1H-tetrazol-5-yl)-thio|-methyl)-benzoyl)-cyclohexane-1,3-dione (1.0 g ). oxalyl chloride (0.91 g) and 2 drops of M,M-dimethylformamide are added dropwise in dichloromethane (10 Oml) and the mixture of Zg 79 is boiled under reflux. The residue obtained by distilling off the solvent after completion of the reaction is purified by chromatography on a column with silica gel (eluent: ethyl acetate:hexane - 7:3) and obtain

3-chloro-2-(2-chloro-4-methylsulfonyl-3-((1-methyl-1H-tetrazol-5-yl)-thio|-methyl)-benzoyl)-2-cyclohexen-1-one (0 ,71g). IR spectrum (MaSi): 1662, 1310, 1279, 1150 cm7.

An example of synthesis Z

Phi sn, 5 o s and sch

M (8) sn, M ikh I ek sh- gi o (22) zo Osn, y

3-chloro-2-(2-chloro-4-methylsulfonyl-3-((1-methyl-1H-tetrazol-5-yl)-thio|-methyl)-benzoyl)-2-cyclohexen-1-one co ( 0.75g) and thiophenol (0.19g) are dissolved in tetrahydrofuran (7ml) and a solution of triethylamine (0.19g) in tetrahydrofuran (3ml) is added dropwise at 59 and the mixture is stirred for 4 hours at room temperature. After completion of the reaction, cold water was added to the mixture, extracted with ethyl acetate (50 ml) and dried over anhydrous magnesium sulfate. The residue obtained by distillation of ethyl acetate is purified by chromatography on a column with silica gel (eluent: ethyl acetate:hexane 7:3) and 2-(2-chloro-4-methylsulfonyl-3-S(1-methyl-1H-tetrazole-5 -yl)-thio[-methyl)-benzoyl)-3-phenylthio-2-cyclohexen-1-one (0.61 g). T. pl.: 76-8796. "

The compounds obtained in the same way as in the synthesis examples 1-3 above, together with the compounds synthesized in the synthesis examples 1-3, are presented in Tables 1-3 below. . Examples of compounds in the case of compounds of formula (I), which correspond to this invention and which are represented by formula a

KE

I ve 5 -k 1E so i - oo 50 8. (СН M t 3e) and ra o are given in Table 1, we) examples of compounds in the case when they are represented by the following formula 60 b5

Kk o Xh ich. M o (СНИ З -Хх цм мы are given in table 2, and examples of compounds in the case when they are represented by the following formula in ох а 7 and М "М

M Manure and are given in table 3.

In tables 1, 2 and C (8)

O1a means group

Ge) so (ee) "I h- " - s z -I t" (ee) o 50 (Che) (F. ko bo b5

It means a group

Fe o) 0156 means group 8) p

I So Y p.s and o n.s F so so

O01c means group - h-

Go) ns them - with n.s a go. -I ' t 02 means the group so o 50 so o

F,

Po) (o) because

ОЗа stands for group and ОБ means group

This means a group of

Fe about 0156 means group 8) sch

I C and n.s and o n.s F so so

O01c means group - h-

Go) ns their shi s n.s a go. -I' t 02 means the group со о 50 с о (Ф, о о 60

ОЗа means a group, and О1с means a group

It means a group

Fe o) 0156 means group 8) p

I So Y p.s and o n.s F so so

O01c means group - h-

Who are they - with n.s y?" o -I ' t 02 means the group so o 50 so o

F,

Po) (o) because

ОЗа means a group of shchi 092 means a group

This means a group of

Fe about 0156 means group 8) sch

I C and n.s and o n.s F so so

O01c means group - h-

Go) ns their shi s n.s a go. -I' t 02 means the group со о 50 с о (Ф, о о 60

ОЗа means a group оЗа means a group

5 5

And 035 means the group "c

WITH

| , o c 5)

ОЗс means the group (22) с со ив з

And "

Su і- o « 7 934 means group З с щ сн, -И 1» 5 (ee) с 50 со о ря ОЗе means group

F) yu sn, : B tA bo Z o 65 OZ means the group -DO-

at 5

And 035 means group "b

WITH

| and so on

ОЗс means group (о) с со

TX and

With "

Su і- o « 7 934 means the group З с с сн, -I them 5 (ee) o 50 te) o rya ОЗе means the group (Ф. хо) сн, : se p" because З o 65 oЗс means the group -Д1-

5 5

And 035 means the group "c

WITH

| , o c 5)

ОЗс means the group (22) с со ив з

And "

Su і- o « 7 934 means group З с щ сн, -И 1» 5 (ee) с 50 со о ря ОЗе means group

F) yu sn, : B tA bo Z o 65 oza means the group -dD2-

5 5

And 035 means the group "c

WITH

| , o c 5)

ОЗс means the group (22) с со ив з

And "

Su і- o « 7 934 means group З с щ сн, -И 1» 5 (ee) с 50 со о ря ОЗе means group

F) yu sn, : B tA bo Z o 65 OZe means group -A3-

From 5 and 035 means group "b

WITH

| and so on

ОЗс means group (о) с со

TX and

With "

Su і- o « 7 934 means group З с с сн, -I их З (ее) о 50 te) o rya OZE means group (F. хо) сн, : se p" бо З o 65 OZ means group -DA-

ОЗ means group и и з и Со о 75 039 means group те 20 4 5

Sh, p 25 o

OZ means group (22) 30 E so

С with « 35 o i - и « 03 means group o) с ;"

SI

V. 5 of them (ee) c) 0 o iChe)

OZi means a group (F. Vg » S

From vo i) 65 oZa means group -DB-

ОЗ means group и и з и Со о 75 039 means group те 20 4 5

Sh, p 25 o

OZ means group (22) 30 E so

С with « 35 o i - и « 03 means group o) с ;"

SI

V. 5 of them (ee) c) 0 o iChe)

OZi means a group (F. Vg » S

From vo i) 65 OZP means group -Dv-

ОЗ means the group и и з и со о 75 039 means the group те 20 4 5

So with 25 o

OZ means group (o) 30 E so

Fe z " 35 o i- i " 03 means the group o) c z

SI t 5 of them (og) s» 70 o 3e)

OZi means group (F) Vg with c

WITH

60 i) 65 OZi means group -D7-

ОЗ means group и и з и Со о 75 039 means group те 20 4 5

Sh, p 25 o

OZ means group (22) 30 E so

С with « 35 o i - и « 03 means group o) с ;"

SI

V. 5 of them (ee) c) 0 o iChe)

OZi means a group (F. Vg » S

From vo i) 65 OZ) means group -AB-

ОЗ means group и и з и Со о 75 039 means group те 20 4 5

Sh, p 25 o

OZ means group (22) 30 E so

С with « 35 o i - и « 03 means group o) с ;"

SI

V. 5 of them (ee) c) 0 o iChe)

OZi means a group (F. Vg » S

From vo i) 65 OZK means group -To-

OZK means the group and Й

With y and iv)

OZ stands for group

SS p 5) o (o) p

ОЗт means the group со - и В Шш - 5 "- с ;" , about; - And that Zp means group (ог) с 50 с С

WITH

F) ko 60 (6)

OZo means group 65 OZI means group

OZK means the group and Й

From iv)

OZ stands for group

SS with o o (o) so

ОЗт means the group со - и Ри-п -

С « - с ;з» , o -I that Zp means group (ог) с 50

WITH

F) when it's 60th!

ОЗо means group 65 ОЗт means group

OZK means the group and Й

From iv)

OZ stands for group

SS p 5) o (o) p

ОЗт means group со - и В ШЧ - 5 "- с;з" , о; - And that Zp means group (ог) с 50 с С

WITH

F) ko 60 (6)

ОЗо means group 65 ОЗп means group

OZK means the group and Й

From iv)

OZ stands for group

SS p 5) o (o) p

ОЗт means group со - и В ШЧ - 5 "- с;з" , о; - And that Zp means group (ог) с 50 с С

WITH

F) ko 60 (6)

OZo means group 65 OZo means group

You

And -. at; 75 OZr means a group

MO, ke c 5) o (o) 034 means group so d) "

С и- « - с ;» at; ' -I iz OZg means group (ог) с 50 Е 3е) 5

F) ko 60 (9) 035 means group 65 OZr means group

You

And -. at; 75 OZr means a group

MO, ke c 5) o (o) 034 means group so d) "

С и- « - с ;» at; ' -I iz OZg means group (ог) с 50 Е 3е) 5

F) ko 60 (9) 035 means group 65 oZa means group

You and about o 75 OZr means a group

MO,

With s o o o (22)

Za means the group about s "

S i- « shi s z o; ' -I i» OZg means the group (ee) syu 70 E iChe) 5

Ф) име) 60 о 035 means group 65 оЗг means group

You

And -. at; 75 OZr means a group

MO,

From c 5) o (o)

Oza means group o d) "

С и- « - с ;» in); ' -I iz OZg means group (ог) с 50 Е 3е) 5

F) ko 60 (9) 035 means group 65 oZ5 means group

Si a (o) u75 ChZi means a group

God

SYA. with su o (o; (o) so

OZy means grulu so « и-

Me « - with 5 of 45. 7 about them (ee) s» 70 OZmh means group iChe)

EY

(F) co

WITH

60 (in) 65

OZ stands for group

Si

With у75 ChZi means a group

Hg

SYA, s su o (0) (o) so

OZy means grulu so « m-

Me " t s Z z ee , - o ikh (og) s" 70 OZmkh means group 3e)

EI

(F, ko

WITH

60 o'clock b5

OZy means group

Si

With у75 ChZi means a group

Hg

SYA, s su o (0) (o) so

OZy means grulu so « m-

Me " t s Z z ee , - o ikh (og) s" 70 OZmkh means group 3e)

EI

(F, ko

WITH

60 o'clock b5

OZm means group

Si

With у75 ChZi means a group

Hg

SYA, s su o (0) (o) so

OZy means grulu so « m-

Me " t s Z z ee , - o ikh (og) s" 70 OZmkh means group 3e)

EI

(F, ko

WITH

60 o'clock b5

OZm means group

Зм means group se, 5 o th Хx means group

The school is at 8 o'clock

Sh-

F so so so «

OZu means group Kk

Me "shi s;" with -I i» | at

Ge) o 50 s 032 means a group of months about them

WITH

And So 60 o

ОЖха means group b5 оЖхХ means group

Зм means group se, 5 o th Хx means group

The school is at 8 o'clock

Sh-

F so so so «

OZu means group Kk

Me "shi s;" with -I i» | at

Ge) o 50 s 032 means a group of months about them

WITH

And So 60 o

OZkha means group b5

OZu means group

Зм means group se, 5 o th Хx means group

The school is at 8 o'clock

Sh-

F so so so «

OZu means group Kk

Me "shi s;" with -I i» | at

Ge) o 50 s 032 means a group of months about them

WITH

And So 60 o

OZkha means group b5 9327 means group

Zm means group

SE, 5 o'clock; h Х means a group

The school is at 8 o'clock

Sh-

Ф со со со « zv OZu means the Kk group

Me "shi p

I" with -I i" | о со о 50 с 032 means a group of мес о их

WITH

And So 60 o

OZkha means group b5 o32a means group sk. AND

Z ve o 0320 means a group

In and and

Me Fe 9) s o 322 means group (22) 7 si F : « : . m.

SI

« o shi s o 0329 means a group

In all » THEM

Me si 5 at 50: so o

O4a means group

F) about zones,

Fe o b5 9326 means group see I

Z ve o 0320 means a group

In and and

Me Fe o s o 322 means a group

Ge) 7 si F : « : Z h-

SI

« o shi s o 0329 means a group

I'm all THEM

Me si 5 at 50: so o

O4a means group

F) about zones,

Фе о б5 О32с means group sk. AND

Z ve o 0320 means a group

In and and

Me Fe 9) s o 322 means group (22) 7 si F : « : . m.

SI

« o shi s o 0329 means a group

In all » THEM

Me si 5 at 50: so o

O4a means group

F) about zones,

Fe o b5 o932a means group s-m. AND

WITH

So o 0326 means group

In and and

Me Fe o) c o 322 means a group

F

7 si s : « : With h-

SI

« ос - осо 0329 means the group им с я ИХ со си 5 о 50 : со о

O4a means group (F) of zones,

Fe o; b5 Oda means a group of sk. AND

WITH

So o 0326 means group

In and and

Me Fe o; si o 322 means group (o) 7 si s : « : . m.

SI

« о - о о 0329 means a group of them

I IH so si 5 at 50: so ge)

O4a means group (F) of zones,

Fe o b5 O4B means group

045 means group

ZSON

Fe 70 o

O4c means group

ZONE

And wed o sch 04th means group o)

F from ZSeN. in sa so "I o M

O5a means the group "-s" C still 't -I their (o) o o 50 (Te)

O5r means the group o E with c or Z

Зх, б5 О4с means a group

045 means group

ZSON

Fe 70 o

O4c means group

ЗСЗНуп

Y sr o s 04y means the group o) (o) zo ZSeN. in sa (ee) "I o M

O5a means the group "-s" C still 't -I them (o) o o 50 iChe)

O5r means the group o E with c or Z

Жх, b5 Oda means a group

045 means group

ZSON

Fe 70 o

O4c means group

ZONE

And wed o sch 04th means group o)

F from ZSeN. in sa so "I o M

O5a means the group "-s" C still 't -I their (o) o o 50 (Te)

O5r means the group o E with c or Z

Жх, б5 О5Ба means a group

045 means group

ZSON

Fe 70 o

O4c means group

ЗСЗНуп

Y sr o s 04y means the group o) (o) zo ZSeN. in sa (ee) "I o M

O5a means the group "-s" C still 't -I them (o) o o 50 iChe)

O5r means the group o E with c or Z

Х, б5 О5б means a group

045 means group

ZSON

Fe 70 o

O4c means group

ZONE

And wed o sch 04th means group o)

F from ZSeN. in sa so "I o M

O5a means the group "-s" C still 't -I their (o) o o 50 (Te)

O5r means the group o E with c or Z

Зх, б5 О5с means a group

O5c means group 95 si and. o 75 dra means a group of saints,

With s o o

O5e means group (с; со с

S, "I

S, y-

С, ч ши с хз» СЯ means group -и "а и с» И

Min (ee) s» 70 so o ba means group (F) o s

And a (o; 65 o5a means a group

O5c means group 95 si and. o 75 dra means a group of saints,

With s o o

O5e means group (с; со с

S, "I

S, y-

С, ч ши с хз» СЯ means group -и "а и с» И

Min (ee) s» 70 so o ba means group (F) o s

And a (o; 65 O5e means a group

O5c means group 95 si and. o 75 dra means a group of saints,

With s o o

O5e means group (с; со с

S, "I

S, y-

С, ч ши с хз» СЯ means group -и "а и с» И

Min (ee) s» 70 so o ba means group (F) o s

And a (o; 65 OBG means a group

O5c means group 95 si and. o 75 dra means a group of saints,

With s o o

O5e means group (с; со с

S, "I

S, y-

С, ч ши с хз» СЯ means group -и "а и с» И

Min (ee) s» 70 so o ba means group (F) o s

And a (o; 65 Oba means a group

O5c means group 95 si and. o 75 dra means a group of saints,

With s o o

O5e means group (с; со с

S, "I

S, y-

С, ч ши с хз» СЯ means group -и "а и с» И

Min (ee) s» 70 so o ba means group (F) o s

And a (o; 65 obr means a group

Ob means group

VG o 07 means group c o

WITH

(o) so d) « h- o; 97 means the group « ts with -I

ChK" (og) o 50 3e) o ko 60 b5

Ob means group 07 means group se o

Ge) so (ee) "I m.

Me means methyl, Ei means ethyl, n-Pg means n-propyl, i-Pg means isopropyl, n-Vy means n-butyl, "

I1-Vy means tert-butyl, p-Hex means n-hexyl, OMe means methoxyl, OEI means ethoxyl, ZMe means methylthioyl, ZEI means ethylthioyl, ZO»oMe means methylsulfonyl, BO2EEI means ethylsulfonyl, ZO»op-Rg o) c means n-propylsulfonyl, О5ОоМе means methylsulfonyloxyl, О5О2ЕЙ means ethylsulfonyloxyl and РЙ"» means phenyl.

Table 1 in m tm 5-Х y o (sn ih soSs her 2 Compounds Me u u V p o Melting point or pr pyati td judge sh-- I y ts - shen. v sononoya Me shlya a shov bo shi - -- and 14 me НО000мМе001 ota her and sh o - - shoyu int vetotnyati is sht wat spe no stoyak shyo shiya yaniya

I-6 Me N Me 1 Ota so br yar st tvid t work h zv dv tt td trutni k

I a Nv Me,0100 b bBd S v « s 40 - - PE -- --k tu shvmnamenyayu yun E - z - 4 ---- mes ---- tii tova pazh sia yav - shen tyu nya ant shsh - syada t sor ET Wu frotodd tia

Venom ots t str dutya -o3 -1 . them on Na Me 0000 ma 0 so shk on poter ma sota dd t 422 I su 2 I pnia OO LO o a o o o o o o r shi

I-16 n si Me! sleep!

Ge) and more and more. 0 sh

I17 Nn s Me 1 ОЗа я Ве ме вва о | I-49 n S Me 1 07

Po) : he car in | I-21 n si 4 1 Sta

I-22 | N ve Me 1 bla zvi 65 I J

Compounds Me m i ' i A. 00:0 Temperature ! | "melting or pr y po zh yn ny ny khny en t 0 V Me 0110 bza000 va НВ Me 04 bBai000000000 to fall Matte scabbard write n pys nyshi write "I ba ' Y y ' pan Me 1 sna, du ON Me01100aa00 tn Me001 za va NT Me 004 BVA

I-34 | n And ! 7 1 Sa

I1-35 n Me Me |. Sta so tv NO s Me 17 bta so lavu Zb MEZ n t z tav 000 ns Me 4171083 z. en Sv Me 00100 bBa,000000000s 1-40 nin nn i nyshe « 2-7 tyny nyny ny shiny write Z z Ii-42 "pn shi: 1 0a. sleep pn nn. oh ote i ! -53| : !

V. | ' » pad t tomMe 1 Me o tota shki pa Z Z oMe. 7 Me 71100 se 70 nt don dor vo 06 ev i47 n s OMe | 0 Me 10011001 O5a) 1-48 ' N OoMe Me 1 Both 74-76 o I-49 and I with OMe | in ' And! Ota: m | | -shhhh| ШИ ств 7 loBome: Me 4 aa: pa 0333 TOVOMei Me 15353051 b5 va

GSpolukimeiu ( 06400001000и0000000000п0000016001100 Temperature of melting or po?

ОН о8ОМе, 0 Ме 010000 0bta.id 00000000 pan nn nn now why is it

Y V NO OO Me, 00 Me Ob3za000 th (800 OoBOMe 0 Me 01000005. brova tn teomMe me 00 lova ZO- tvo 77 o8OMe. EE Her bid 00000007 education t t sya work i action and submitted bu dryty and songs nn nn nn na nia and s

I-84 n MO» Me 1 OoZa ! from ts to; MET ut dvdT t t y nn nn nn ny nn nn iy pdv tn there td tia and her 4 | « z p nn nn nn wn nn nn nn shchi eeda td teme tav series dya " - poisons dk t rode tt - chi 72 N sk E 1 sa

I-73 nn CM 1 la 45. - 4 ry a NO osn 00 Me 0001 00bta and Y SELO VEDE, KMT yes

I-77 M OSNE; Me 1 Oba

CLEARLY SLEEPING 000 Me 001000бба0000000с о | 79 --. -- H 4. Osn, -sh--- ES millet I belat - bod still | vi p no nn nn in vo av ob Me 000410 0b1as sho y van n bos Me 000000i0002 shi Y b5 vv.

Compounds Me, in . 2 | with that 9 7 Temperature. melting or melting of those Os Me 1 pava 3

KN Ob3 01 a and ab Ob 000 and 1 a t

M Table 2

Iv poh M. sch a F sch o 2 (is) so (2,0)

Compounds of Me. x ' 7 in poi 00000 Temperature Z | fusion or about pt Me. 0012 baht 0033331 47 I-Z ni nin shi shi shi ni Z » I-4 s ОМе . n Me 1 spa. Fri. бмМе00НО 100000 Ме 00110008, I will divide the NO. Me 00011 baht 33

Fo MN Me dat 00300 sha, o pe ON, Me tag tia i ZY i ol Me 1 oa, 66-72 i PS TE 16 me ha

F) y r kb Me 4 1bzai 000 bo a 00 a - she bo -v6-

Compounds Me, in . 2 | with that 9 7 Temperature. melting or melting of those Os Me 1 pava 3

KN Ob3 01 a and ab Ob 000 and 1 a t

M Table 2

Iv poh M. sch a F sch o 2 (is) so (2,0)

Compounds of Me. x ' 7 in poi 00000 Temperature Z | fusion or about pt Me. 0012 baht 0033331 47 I-Z ni nin shi shi shi ni Z » I-4 s ОМе . n Me 1 spa. Fri. бмМе00НО 100000 Ме 00110008, I will divide the NO. Me 00011 baht 33

Fo MN Me dat 00300 sha, o pe ON, Me tag tia i ZY i ol Me 1 oa, 66-72 i PS TE 16 me ha

F) y r kb Me 4 1bzai 000 bo a 00 a - she bo "Tuesday.

Compounds of Me X 2 | I ate 00000 Temperature! what ; melt or pore? gate 33 -shfsh with tya TE tot ov -4Ox3 iv | | - sh shi

Ne ab Mme 0031 Ota: 1.6010 pi nn: nin: niny and pit oi yo bat me Z 17biv sla eta. me au 7 p zhi pish pn i pish sch z y o Meta o bra Zam tov p Z real met i az F board ato Mme to 3 o tra; 073 tet met lad Fo p-eZ S SI | Me 1.05 str; tota met ba « liu yi-z1 si b Me 1.07, with s di writes p E: aa: write: shi: nim: now know shi sums in pi: nim: nim pi i i shen; pi and adeo 067311 syu yiv 00360077 Eva. s pd: nyny: nm ny y: galo ste 0060671 Gov y: shi shi shi ny z ik Kp o ve at SE I Gb 00030033 ope v b v rai v da v b ES 11 1o6 gu mn ye PI I s E 110977 ny nin shimi: write in yete 65; vv.

Compounds Me | Xh 'uh | In p O 000 Temperature ! melting or by? same and pn a py ro u In te at t ryaba p nn them now mn p t aa board, Two 00000 a aa avta and drank below nyshsh write shi im niky now now write shi write pa3 tata ro-3-f | ! : 20 | ' :

Ba 0Sa «y kish write and ' | s 7 and -T a (6) with 00006 I so nn - nn and sixth 2 so y-B7 si b. 1 177 oza « 35 | M. pi: write om o Y 1 OZe g - s I-5o9 S : s I 17048: ;» ' : 4 n-6o si "p SHE She: y z | | -y42e4y r, z. nn, so y o b Ya ova: o she / ; NI o ti nivy s p ШЯ 1 Ova - channya o p-e3 si v 7 yu ! ! | : zna p pi VV zn bo P-54 . C s s, N, | 1 | sla ' | 4 ! I ' y b5

Compounds Me, x 7 in! by 00 300 Temperature ; melting or etc. ; avta a yuitEO 0067 aliArana ate? 3707 и-,ООбТ ne SD ивв 006776 sbnEsN, 700001 write with them shiniks steki kikh lk. pyv vyg: nin PI hundred pov pn. along the pi line pi z post stv pi PI s 25 p-72 SI SI b -bneSNn, 1 oOZa o iz 5000 Со ОНneSN, 00 Oda, blashe bab sov, Fyu stav 0076 obnesn, 1 b s slov bl b ssnesn, With bba, so bl 07670300 bi sstbnesn, ota; h (|v 33670610 ssnnesn; 05 t p-79 | s s s SbnoNasSnN: 1 s ОZA tob sstsvsn.bva 1 dov 007077 aa 7 "z p-v2 ' SI ' Si ! 2-0I-Rp shE Sta: ate 533716 Amer | ba. 3 I gvai tela svv TYA bat 77773 to |v r 6 ev I ba

FV OB 61 bNDNA slave

H-88; SI 's snNiSNnye 1 Ba dv VU SS 1 SNSNK 1 1 Ova) SHY (F) p-90 | WITH! ! si | SsnNeNnos! | 1 h sa zo 66 sv i 00810000 60 p-92 : o s 0 sne 1 s Oza sing white bno 6 73 b5 o.

Me compounds: X 2 in spo Ob 0 00 Temperature: melting or po? |v bo NOV I ov vyt write nin p s o ih p t I b ortdv 76703761 svv 141 b words 003603 bno OB gde Z 6 6 sne tab Z sto b bo both

NNYA 00sSssi So snyuRR; , 1; But the lines are only available: DESTROY

N-107! SI with SNONoNE. 1 ! Both: writes: pi PI PI ik tote koh pe sho PI her 1-110 C! with | СсНсСНСНЕ 1 soza. co

NYA 0Ss SI SsNoSNesNYE 10, Ba « z | iryaa 767 5ME 0000 Me 07708000 m PVCh Sha 8Mme 00 Me 00770003

Chia 77 el 7 6Me 7 TEO « ilshchi5 bi 8Me - po ni v s -a.7 shi ;" ' ' Y : ro ti; water temperature is 78-84 °C yav i00b00 0 5bMe 0 Me | there! so 19 10000100: VO Me | Me Prav,

FG a» o rvomei Me 4 Go i» 61 vomit Me 11 10885530076-8773 o p-123 ' S and 80Me ! Me | 1 | Wasp! 2g1i1a-211 z paye 11) BOMe Me |, and I si I ZOgMe : Me |z | Oh yeah; 79-82 and plavu C 1 5bMe Me r o5. Sh

P-127 SI; zO.Me | Me 1 | ObBa b5 c.

Compounds Me x u p p 0 00 Melting temperature or po ! a 00000600 8bMe 0 Me 01 OB deya o VomMe Me 1 two, - p-130 What si "ZO2Me Y Me more 07: m Te EI NN in POT and Z NN o x RON u Du VI aa S 8OMe01O V ota 0 ik: nimi pr Z p pok x x p | sf VI VOM YOU I Taya chic now tire and now about nn

M nik nin them o nn - a ek NN

I-137 SI 5OMe E sho Ozo! Теадяв тв в род рн ек н н н н з, н НН п s п о тя яры ВОДИ p-142 si OMe shchi dva Y so (000-143 si zoMe EE | 07 so ynyayea 0000000 50Me 0000-0010 0bla 000 142-145 ШЧI « | had S VOMe 00000002 ШІ йяяЯяВ 000 8ОМe000eР00011Ю8a | NniaaH S 5biMe 00001 bta 000000 68-73.. | that khz» P-149 SI ZO2Me i-Rg 1 02 ztyavb tel tvozhe tv u vdshi sh zho et rdESH tor vv EL howling tbvdt m she nyny shk nyn ny nn 0001400 shi s P-153 SI zOoMe and 1 Ot1 | p s po En, p p skh .

Y -e573 p-155 SI zOgMe 1 02 6o | -eOkh3 sht nn yn yn nn be

Spontaneous Me X 2 : v a: o Temperature ! : melting or po? ram KO 000 8ОМе 00000011 for 4 she ie sly so, ma ah o: YOU 70 ' yani | : :

MB 000 Si 8bMe - f« 1 11 Oda : : and And papy write: ni p; VE Ya t yav 30373 BOZHMe -zh 3 java. it is 0000000

I-161 SI 5OoMe 1 Both schools ro-- | o at 00 s 50Me s 170

Pl o s (ze) і- 63 fs 5oMme NO she: so -3 still her n V t

I-i164 si 80Me sv 1. og o-3y " nn i i a a i i a a NN sho s 465 s ZOMe 0 oot-СН, s Ota,

And" | - zv vv 0000 8ОМе, pelvis: with | | | -k r v so i-67 0000 bi 8OMe: go o | | | - shi s: ylve i00s7001 85bime | sbNeSN, 11 | she is in | ве 1000С10001 0 8б6Ме; SSN-SN, pt viv

Ф тя 0300671 5ОбМе 0 СОНяСН. 1 constellation 10061000 5bMe ssneoi (11r 02 -O pn povy da SHA MOH po vo y?72 0.006100 8bMe 00 SONSN 1 | 03 y-73 01000010 505Me , -SNeSN, | 1 | la, la 00010001 8b.Me 00 -sNASN 1 ee b5

The temptations of Me: X and 7 | At 00, 00 Temperature: ! ; melting or by?

Goliav would have lost sleep, ba. 77773 и ия 00 b 7 8ОЖМе СбБСНеСН, 1 sa) 63 -68

Snu 777670 BO Me sonyunyas, 10300000 i and 701; 8b,Me /СНСНеСН; 1 | O5a java 00001071 8bMe 00001101 ota java 000000 8bMe 0 ЖEO ba. m | her b BO obi 010 ota 84786 i-8v4 s vome ZEBRA 119, nav in 5bome / 4MOURA | ota: Y c 2 | In 300s100080Me sSNSNHE 4 sa. o (-і87 so 8biMme СНюНЖ 100. td er 8bme sne 41333 o 3o P-189 Ш С8ОМе сСНСНЕ 1 Оба: р йлео 0000000 bOMmmMe her DREAM 11 ba so siav 7 671 8oMe snod | 057 - in Goth 7 0 8bme sisne 188: t ee b oVole snene oba, roma 710108bMe SNO 1 se, 82-87 Z s n-t95 si 5OaMe | 0 SNSvz 10005. » yleb 300670 VbmMe OSNOV 34100000 im Pa498 0.000000; 5OMe 000 SNoSRz o; 1) OZa0 t700 10 000 БбМе | SNSV 1 rbat about 77000 BoMe| sat 11651000 so iFbi 00000010 80Me | SN 101 1 both yo 00067000 БбМе 00сНЕБО 04бб41000 loz 100011 18О,Ме | SN | 1, 07

ОО 000 rotyaom)000С100015ОМе her SNSRSV» | 1 | That's because she b2o6 10001007 850b5Me | SNISRAStz 1 ОЗа илиеое 100001 Б5биМе | TOLERABLE | 1 | that's because in

Compound me ; Xh | 2 ' in bpoi 0000 Temperature is "melting or po? | 08 ni o li in ni z p

But Со ЗОЖМе сSNниСнСнНяК 11 ОЗа set 00000100 БбжМе | sSNNeNyaE 1 ba; "Ha b 80Ж 00 Me 0000 aa. 70-74 yeei3 1000 bi 8OE Me 2 8 I ob met ОЗа

P-215 and SI ZO | Me (and Both: yShei6 30С1000008bMe Me 1 two; yu U 06 VoMe. 0 Me 01110753 her with bbMe in ba: 220 00С100. B5ОMe and tota about her 6 oo | | -fa.1 so goes bi tvo 6 7 loa. 77 : | -41 shi t | : : i ! і- і223. b GOD SSNesN Ota, 224 00100000 GOD'S SSNESNIOS 01000200 " sho Gteov lasovba "and sat: shchi g" with us sh shi i Me Satana: 72-78 m te: YOU and me

I and you now write and write p o i-230 shi shi Write OZa 23 VVS. And Me 1 ros.

P-232 W | Vg Me | 1 OZ mine i i Me 1195 vo az 0000000 Vb Me 011 rova; ev 10 VV, Me 1 1 o5e! m: Me two bo

B

Compounds Me x u ' in po. 0 7000 Temperature ' | : melting or pre? once 0000000 V Me0 7107 t I: shi: ota, not po: writes E 102. sho 7 y2Yai 0000 Ve Vo Eii t bah va 100000

U nshi: ii I Z: 11 OBA, lLtuit bortakh 77 VO V R Goa shi, now, now, now, now, now, three times, i-Rg 617 ota saw, now, im, on, mm, sn: write kny p o sh ' sc: o tannin ayu si av mn | Ф p-250 'Ve Vg: that's what so av You 1 "even now! ! " " in

Sho m -252 o -hya write: now sho: Z - p ni and also Yagoda: tt ? | | | -fe5| shi beer and an i : : ped - iga 7BVO 4 to. 2 | | | shi nn V p so yo55 1000 VO VOS.u 1 GOBa, I shi she

Fo nnnnnnniazhyanNnyanzhyaIFya pnya UN and IN

Ine5v o; Vg and 100Vg | | 1 and ba zv | o shi she o BEER KANA PON ON POKONO Kitsya KO yuyu 257 ' Vg ! Ve and -bnH-СНе | 1 Stanina according to I N

Seam | Vb Vb sSNnebNa | 1102 7 iv 1000 ВгО01 00 Во ОнеСН 0/1 For

P-2b0 0 1000OVg I Vb; SNeSN 100 O5a and 1000 Vgo 0500 Vgo 0 сSNeSN, | 1 | That's it! And 65 : : : :

Compounds of Me X ' y : in op. b 00 Melting point or pr?

Played VO VO 1 SSNNASN. C 00020000 fu. VVR rya bat pi: tire nyny ie ton o t in

Played VO Vbo as 01 70ba 0003303 p nn i nn nn to:

Crushed stone 3000Vb 0000 Vo SSS both

I-269 VG | Vg SNnsSNnoSI 1. 02 shi: write that zi pi write shi niny: nin oko NE es NI z | ve VO VO00 SBS 0041 bvat 0000000 o

P-274 Vg! Vg; DREAMS; with 1 Ota.

Stev at 00 8Vb 0000 V OsNovSNE b sh 30 -278 Vg OoMe Me 1 ov, 87 - 80 so and V 8bZhe. Me b 05 so liu n-28o Vg 5OMe | si a | 1 Spa, - | SHY "z | , ' | : 1-281 V . 50.Me -bNa-SN. 1 o sta z Gayu obme 11061000 Me 001100 ba 000163 g Pifv3 100OMe 00020100 Me 01710 B:

VA 30 Ohme 500000 Me 0140 y she 10 obme 100 Me 0014180 lav 0 bMe 0000700 Me 011000 v | av? bMe 00100 Me 0115 bv) about Ii-288 btome 6 me 00000 mo hav 1 oMe 10610 Me 0017301 both; yu | and 1 bMe 7 Me | mega ra

P-292 00 ОМе ге | g | 1 | 02. wY 65 vt.

Compounds of Me X 2 in opo; 0 0:00 Temperature ' ! ; and melting or about once 1 Ω 0 both. 0 ObMe 61 two 0 ng OMe 000: E a "7 | rgov OMe 070001 ota; SHHI 7000000 OMe 0000 p-Rt 1021

In ОМе 0 С, i-Рг 1. ' ши и ши p1Й299 0 ОМе s. Rg 189, о 000 ОМе с бла | SHI SHE

II-301 OMe S. and 1 ov, And more

I ' : ! ! with 'I corkscrew 02 L.O 2 5 2 20 2 5 90 ( 25 ю6 5 ( « 2 (Z 5 5 X s | yog OMe s, be o shk. sh- 803 Me b ry F» her-304 Me b tova so -joK1 še «

AI | I and i- p-oB5 0.0 ОМе 0 сс 1 Oda. tn « 306 0000 ОМе 500001: ови 2

T-307 ОМе 0/0: 11 OvBa, I - | ' ! | | ! i» yo 10 OMe 000 00 ne p oat t ; With | : co | | | - what?

Pho! shi so 1-09, OMe her s |i ST ota; ; -(5 shi 55 Sho: SHE and I o ZO 10 ОМе 700сС101 -СНеСН. 1 sa; юня 0000 ОМе 06100100 -СНеSNХ 1 08 z Za 0. Me 100Си1 001 СсНеСН, 11 Oza), ше

НЯ 0 ОМе 100010) -snASN, y r o5a; Shchi Chh 1-34 obme 00001000 ssNSNnesn, 1 I 1 ota:

Y Y : Y y b5

Compounds Mo | x 2 ' in opo; about 00 Melting temperature or 6,000 Ωe 00 s. RA r sta tay obme bi ab 14 bla 3 a |i: 0 bme 000677 sSneNE 4 biv wa 7 ObMe 0 SS ryaba

She has 30060 bNDNYU of her Z

Right of way 1067 veni 6 shins y: Pt ie t OM i yishchaez /0ОМе 00100, 0 Сов 001005 й-324 ОО Me b bНV 040 О8а

SVB tome 0300010 bo 004 ba 327 0 OMe b SBsNSNE 1, a: ate OS 0077 Me 71 bid zo ate Osn 00007330 Me 341105 her

From 000 OSNE: 00: Me 1 Ozai so-3rd 000 OSN; "000 E lota " zv PVve 3 Mon 00000041 ota: I mon "NI

Svaa3 0 OSNE; 00010010 СбНеСН. 0, sa h z iZa5 0 OSNyuR. 0: Me pal 01836 s ostst, b. E uva - 337 0 ZMe her s 1 Me 1 Goa

I» 38 00 5Me |. Me 11021 so shaza oi 8Me 10 rana, 0

Fo hola VMa To pt aa y | | - high | | ШЯ vv |Z 000 8Me 07006101 sne, 01 ota

F) yZda VMe 1 O5Me 7 Me r ba? 000 dk y-zaz 8 5Me Me | Me 17021 bo 344 | 5Me | Me | EE 1 | with i8a5 00 8Me 00 8Me Ghana,

ON because

Compounds Mo, X 7 in | on! 0 5000 Temperature ' ' | melting or pr? ШЩ Shchi chinny ia 00 805Me 00010000 СнеСНЙ sna: ю vva 7 8ОбМе ВбЖе: Me

Sava 0 8oMe VbMel 00 point 33

Sl 8 bbMe 1 8bMe her 00000011 bat - -4« | . | sm t nyu shk i o pub 00 50.Me 5OMe SNASN 1 oa,

I-357., Me and ZOMe Me 1 hundred 69-71 F

I-358 0.000 Me 5 5bMe | Me sa ba s stvzva,. 0000 Me 1 8bZhMe 00 Me 0331 0IB0013030131030131030131 o tab 000 Me Z 8bMeYIT Me 1 bis: - zve 1 Me «8ome Me 10833333

Slrzyez 300 Me 0 bbMe 00 Me 00413055 3333333333300 47 364 000000 Me 8 8bMe sttme 245 b. that xz» ab 100 Me 5ZbMe. File: 0001011 0 | vev ptme Vb Zheyi Me OB - I-367 | Me her 5zOmMe: Me 1 g O5a with ii-368 me 1 8bMe |) Me 05405600

I 50 1I-369 Me ZOoMe What Me Shi s Oba! at 01370 | Me 0 580Me What Me 1597 her 000 Me | 5Ω E Goa) zv P-372 | Me | 8 OhMe | E 15, o z ro Me 8OMe| OB fr 1bzai s yu N-374 Me | 8 OhMe | EC (1 ov in 8750500 Me 8bMe 0004 fb5a| 00000001 376.) Me oi 5bMe yav bota; 377,000 Me 0 80 Me| pR 102 b5

Compounds Me. X! 2 E in I yai o. 000000 Temperature and ' . ; melting or po" 780000 Me 1 8bMe 00 RR 00741 bla 0001

P-379 Me 80 Me, St. Fr. i-z80 0000 Me 0 50bMe ota: Sho to ' ; 181 070000 Me 00 5bMe : y a go, ШЧ ШЧЧI ; ' !

I-382 Me 5OMe 1 Os, shchi that H-383. Me ZOMe 17021 4 38407000 Me ZOMe 1 For what see | nya | ' o) t-ZVe Me o Me 1 oda tt | | and ' ! co

P-za6 Me : ZOME SCHE She so she she - sht do du poshu dn plan ptn ttyni yati tn ptn tn pni ono i - bortlavu 0000 Me Z 5biMe 4 Sava: ' : ! : ' yu P-388 70000 Me ZOMe S,N, 1 ota o! with m

I" zh nnnnnnnINENI NIVA NV A a pan pa ekson Na a a a in p-Sh89 00000 Me 00 5bMe: E vo ra z | 4 shY » | More

So 1-390 'Me and ZOMe, 11 ota s - she

F and | | shi

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An example of the synthesis of 4 o cS,n, o o I -.

SN M about Z: in- and! and mM 2 von 5 g of 2-chloro-3-4(1-ethyl-1H-tetrazol-5-yl)-thio|-methyl)-4-methylsulfonylbenzoic acid (0.77g) and thionyl chloride (0.49g ) is added to 1,2-dichloromethane (30ml) and after adding 2 drops of M,M-dimethylformamide, the mixture is refluxed. After cooling, the residue obtained by distilling off the solvent (8) is dissolved in dichloromethane (10 ml) and the mixture is added dropwise to a solution of 1,3-cyclohexanedione (0.28 g) and triethylamine (0.28 g) in dichloromethane (1 ml) at 59C and BG is stirred at room temperature. Then the reaction mixture is extracted with dichloromethane (100 ml), washed with dilute hydrochloric acid and Ge! with an aqueous solution of sodium bicarbonate and dried over anhydrous magnesium sulfate. The residue obtained by distilling off dichloromethane is purified by chromatography on a column with silica gel (eluent: ethyl acetate:hexane by volume 3:7) and obtains (oz

3-oxo-1-cyclohexenyl-2-chloro-3-1(1-ethyl-1H-tetrazol-5-yl)-thio|-methyl)-4-methylsulfonylbenzoate (0.83G). t. pl.: 122-123S. in

An example of the synthesis of the 5th- o.s. Thesis

M -- h

Sn Y shi s no ak M

Henny 2" her 50,CH, -1 that To the solution / methyl-2-chloro-3-(1-ethyl-1H-tetrazol-5-yl)-thio|-methyl)-4-methylsulfonylbenzoate (0.83g ) in dioxane (15ml) add 1N aqueous solution of sodium hydroxide (1.0ml) and water (2ml) and the mixture is stirred at room temperature. Add water (ZOml). Then, after concentration under reduced pressure, a 10N aqueous solution of sodium hydroxide (1.00 mol) is added to the sodium concentrate and the concentrate is washed with ethyl acetate (100 ml). The aqueous layer is acidified with hydrochloric acid and extracted with ethyl acetate. The organic layer is washed with saturated (95) aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. Ethyl acetate is distilled off and 2-chloro-3-1(1-ethyl-1H-tetrazol-5-yl)-thio|-methyl)-4-methylsulfonylbenzoic acid (0.80 g) is obtained. T. pl.: 193-19526.

Synthesis example 6

S.A., o o o o M. r MO Z-X M

Mch

OH, 1-ethyl-5-mercaptotetrazole (0.31g) and methyl-3-bromomethyl-2-chloro-4-methylsulfonylbenzoate (0.80g) were suspended in acetonitrile (2O0ml) and after adding potassium carbonate (0.32g) the Zg suspension is boiled under reflux. After addition of cold water after completion of the reaction, the mixture was extracted with ethyl acetate (1000 ml) and dried over anhydrous magnesium sulfate. The residue obtained by distillation of ethyl acetate is subjected to recrystallization from a dichloromethane-hexane mixture to obtain 2-chloro-3-4(1-ethyl-1H-tetrazol-5-yl)-thio|-methyl)-4-methylsulfonylbenzoate (0.88 g ). T. pl.: 109-110960.

Study example 1: Study of herbicide effect on rice field weeds.

Preparation of the composition of the active compound.

Carrier: Acetone, 5 wt. h

Emulsifier: Benzyloxypolyglycol ether, wt. h. 70 The composition of the active substance is obtained in the form of an emulsion by mixing wt. part of the active compound with the above-mentioned amounts of carrier and emulsifier. The proposed amount of the composition is diluted with water.

Research method

In the greenhouse, seedlings of paddy rice (variety: Mirroprage) at the stage of 2.5 leaves (height 15 cm) are planted in a pot with an area of 500 cm2, filled with soil from a flooded rice field. Then they plant seeds or tubers of 75 small-flowered, reed, monochory, broad-leaved weeds (Iipdegpia rugidagia, Indian rotala,

EIayipe igiapaga, YuOoraighisht |psesht Natiiy, etc.) and khdharapeze hirrop mara and pour a layer of water approximately 2-3 cm deep.

5 days after planting rice, a composition of each active compound, prepared according to the above method of preparation, is applied to the surface of the water. The herbicidal effect is studied 3 weeks after treatment, and during this period the water depth is maintained at 3 cm. The herbicidal effect is considered equal to 10095 in the case of complete disappearance and 0 95 in the case of no herbicidal effect.

It was found that MoMo compounds 1I-18, 111-117, 1I-122, 1I-131, 1I-194, 111-212 and PI-71, when applied in the amount of 0.25 kg/ha, have a herbicidal effect on rice-paddy weeds an effect of more than 9095 and are safe for rice-paddy seedlings. Ge

Study example 2: Pre-emergence soil treatment against field weeds. at

Research method

In the greenhouse, the surface layer of the pot with an area of 120 cm2 is filled with field soil, and then seeds of chicken millet, foxtail, common amaranth and sedge are sown in it and covered with soil. On the surface layer of the soil of each pot, the proposed amount of chemicals, made (o) in the same way as in the above example of study 1, is evenly applied. The herbicidal effect is studied 4 weeks after treatment.

Results: (ee)

It was found that MoMo compounds 1I-117, 1I-122 and 1I-194, when applied in the amount of 2.Okg/la, have a herbicidal effect of more than 9095 in relation to the studied weeds (chicken millet, foxtail, amaranth and sedge). and -

Study example 3: post-emergence foliar treatment against field weeds.

Research method.

In the greenhouse, seeds of chicken millet, foxtail, common amaranth and sedge are sown in pots with an area of 120 cm2 filled with field soil and covered with soil. 10 days after sowing and covering with soil (weeds are in the stage of 2 leaves on average), the leaves of the plants under study in each test pot are uniformly applied the proposed amount of chemicals, prepared in the same way as in "" the above example study 1. The herbicidal effect is studied 3 weeks after treatment. It was found that MoMo compounds 1-18, 1I-117, 111-122, 111-131, 1I-194, 1I-212 and 1-276 when applied in the amount of 2 ,O0kg/ha have a herbicidal effect of more than 9095 in relation to AIoresigiz (chicken millet), Espipospioa sgivz-daiii (foxtail), amaranth and sedge. - Study example 4: Study of synergistic effect when applied by spraying leaves. their Preparation of the studied solution

Carrier: Acetone, 5 wt. h. bo Emulsifier: Benzyloxypolyglycol simple ether, wt. h. so 20 One part of the active compound and the above amounts of the carrier and emulsifier are mixed to obtain the composition of the active substance in the form of an emulsion. To obtain the investigated solutions, the proposed amount of this composition is diluted with water.

Research method.

In the greenhouse, the soil of the flooded rice field is placed in pots (250 cm 2 ) and in the surface layer of the soil, 29 which is in the pot in a wet state, weed seeds (chicken millet, reed, monochoria and (FI Ipaegpia rugidagia) are sown and covered with their soil . All types of weeds are sown in each pot separately. All pots are filled with a layer of water 2 cm deep. After the weeds grow to the stage of 1.5-2.2 leaves (or about two leaves), after releasing the water from the pots the weeds in the pots are sprayed onto the leaves with a predetermined amount of the compound in the form of a test solution prepared as described above 60. One day after application, the pots are re-flooded with a layer of water 2 cm deep.

The herbicidal effect is studied 4 weeks after application on a scale from 0 (absence of activity) to 100 (complete disappearance).

The results of research for study example 4 are shown in Table 4.

Study example 5: Study of the synergistic effect when applied to the surface of water. because Method of research.

In the greenhouse, the soil of the flooded rice field is placed in pots (250 cm?), and weed seeds (chicken millet, reed, monochoria,

IPpaegpia rugidaga, rotala Indian, Eiaipe igiapaga and siti) and cover them with soil. All types of weeds are sown in each pot separately. All pots are filled with a layer of water 2 cm deep and this depth is maintained throughout the study period. After the weeds grow to the stage of 1.5-2.2 leaves (or two leaves), a predetermined amount of the compound in the form of a test solution, prepared as indicated in the above research example, is introduced into the pots by means of water surface treatment 4.

The herbicidal effect is studied 4 weeks after application on the same scale as in the study method 70 described in study example 4.

The results of research for study example 5 are shown in Table 5.

The synergistic effect for Case Study 4 and Case Study 5 is estimated using Eq

Colby.

Colby: E-Xx-GuX(100-X)/1O00

E: expected herbicidal activity at (ra) g/ha,

X: herbicidal activity at 9o at r g/ha,

In: herbicidal activity at 9o at 4 g/ha.

The following abbreviations are used in Table 4 and Table 5:

SURBE means Suregiz zegoiipiz (stringer)

ЭСН5ЗЗ5З means Espipospisa srr. (chicken millet)

EGTRRR means EiPIipe giapaga

PORU means and ipdegpia rugidagia

MOOMUR means Mopospgogia madipaiiz (vaginal monochoria)

KOTIM means Koiaia ipaiisa (Rotala Indian) Ge

Compounds (1) in Table 4 and Table 5 are designated by compound numbers previously used in Tables 1,213. at

In Table 4 and Table 5, other known herbicides are marked with capital letters according to the list below:

A: 4-(2-chlorophent)-M-cyclohexyl-M-ethyl-4,5-dipdro-5-oxo-1H-tetrazole-1-carboxamide (phentrazamide), Ge)

In: 34-dichloropropionanilide (propanil),

C: MM-diethyl-3-mesitylsulfonyl-1H-1,2,4-triazole-1-carboxamide (cafenstrol), o 0: 3-(1-(3,5-dichlorophenyl)-1-methylethyl/) -2,3-dihydro-6-methyl-5-phenyl-D4H-1,3-oxazin-4-one (oxacyclomefon), (ee)

E: 2-chloro-2',6'-diethyl-N-(2-propoxyethyl)-acetamide (pretylchlor),

E: 2-(1,3-benzothiazol-2-yloxy)-M-methylacetanilide (mefenacet), that is: (RB5)-2-(2-(3-chlorophenyl)-2,3-epoxypropyl|-2- ethylenedione-1,3-dione (indanophan).

The expected activity of the OPO Paul by Gav'iau is known eroicide (g AB "TV) compounds (with herbicide (Avt), from the village of BB in 00010101 ME 00170016 in 01511815 O1000

FEV 0000101011011010110110110110111111111111111111111111111111 (154,100)

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Ron Xz Inn Posson Post Pos Pan P ve 0000100100100yu010111111111111111111111

Fu Yuyu 98800118 vom 177711tyu117111111vo11111111111hev1111111111111vv

Study example 6: Study of the detoxifying effect on rice when applied to the surface of water

Research method

In the greenhouse, the soil of the flooded rice field is placed in pots (1000 cm?), and in the surface layer of the soil, with what is in the pot in a wet state, rice seeds (Mirroprage variety) are sown. 7 days after sowing at the one-leaf stage of rice seedlings, the pots are filled with a layer water with a depth of Ccm | this depth is maintained throughout the study period. When, on the 9th day after sowing, the rice seedlings grow to the stage of 1.5 leaves, a predetermined amount of the compound in the form of a test solution, prepared as indicated in the above research example 4, is introduced into the pots using the method of water surface treatment. b" Phytotoxicity in relation to rice seedlings are evaluated three weeks after application on a scale from 0 (no damage) to 100 (complete destruction).

The results of research for study example 6 are given in Table 6. (ee)

The detoxifying effect for Example Study 6 is estimated using the Colby equation “

Colby E-HN(Uh(100-HD/100

Zo E: expected phytotoxicity at (ra) g/ha, in

X: expected phytotoxicity at r g/ha,

In: expected phytotoxicity at a g/ha.

Compounds (1) in Table 6 are designated by compound numbers previously used in Tables 1, 2, and 3.

In Table 6, known detoxifiers are marked with lowercase letters according to the list below: a: M,M-diallyl-2,2-dichloroacetamide (dichlormid), o, c p: 4,6-dichloro-2-phenylpyrimidine (phenchlorin), " » c: diethyl-(«K5)-1-(2,4-dichlorophenyl)-5-methyl-2-pyrazoline-3,5-dicarboxylate (mefenpyr-diethyl), " a: M-(4-methylphent)- M'-(1-methyl-1-phenylethyl)-urea (dimron), e: 2-(dichloroacetyl)-2,2,5-trimethyloxazolidine (K-29148), t. 1H,ZH-naphtho/|1, 8-sa|pyran-1,3-dione (naphthoic anhydride). -I m (Fe) (g AV/ha) (U) AV/ha) (U) detoxifier (g AV/ha) (95) (E) according to Kolb (95) this battle 0000 ab 10000000000yutvta 00005000 yuyu 1 s vu 19110001 War 1111 OB War 00 Snake Oy 0090001 Mania 0100060 WIK 000 YUYU OUSUUU1B111111111111111111111111 101 nyakh 151 voi 11 o 101 miakhi 160186 voi 111 yu mito, zu 1911 ataya 01060100 voi 11 ayu 1100 yttta 14016 voi 1111111

NEO OGP TYNY NO NNYA PO voy 11 tuo 30afoy 11000 tha1061080 voy 111 voy 000 voy 11 voy 100 miviat 130156 voy 11 yuyu 1o1meyayuya 120156 cm 2 11 lm 1111111 o

Example of composition 1 (granules)

Water (254) is added to the mixture of MoII-18 compound corresponding to this invention (2.5h), bentonite (montmorillonite) (30h), talc (65.54) and lignyl sulfonate salt (24). The mixture is thoroughly mixed and with the help of a /-F3 extrusion granulator, granules of 10-40 mesh size are formed and dried at 40-5096. co

Example of composition 2 (pellets)

Crushed clay with a particle size of 0.2-2mm (95h) is placed in a rotary mixer. During its operation, the compound MOoIII-117 corresponding to this invention (5 h) is sprayed into the mixer together with a liquid diluent, providing uniform wetting, and dried at 40-5026 to obtain granules. 3o Example of composition C (emulsifiable concentrate) -

Compounds MoIII-122 corresponding to this invention (30h), xylene (54), polyoxyethylene alkylphenyl simple ether (8-4) and calcium alkylbenzenesulfonate (7h) are mixed and stirred to form an emulsion.

Example of composition 4 (wettable powder) "

Compounds MoiII-194, which corresponds to this invention (15h), a mixture of "white carbon black" (finely ground powdered aqueous amorphous silicon oxide) and powdered clay (1:5) (804), sodium alkylbenzenesulfonate (24) and 3c copolymer of sodium alkylnaphthalene sulfonate with formalin (34) is mixed in powder form and "» converted into a wettable powder. " Example of composition 5 (granules dispersible in water).

The MoiI-144 compound corresponding to this invention (20h), sodium lignin sulfonate (30h), bentonite (154) and calcined powdered diatomaceous earth (354) are thoroughly mixed, water is added, extruded using a sieve with a mesh size of 0.3 mm and dried , obtaining water-dispersible granules. what

Claims (1)

The formula of the invention o 50 s 1. Derivatives of tetrazole of the general formula (1): 9 (vt t o I y Su vas "m o Y M--M in which ko 1 . . . Н . K' independently means halogen, methyl, Si . c-alkylsulfonyl, methoxy, nitro- or cyano group, in B2 means C. c-alkyl, C. c-cycloalkyl, C. "-haloalkyl or C. c-alkenyl, t is equal to 0, 1 or 2, while two substituents VK can be the same or different, if t is 2, n is 1 or 2, O means one of the following groups b5 (8) (0-1) Е в эх шчи о в z where ВЗ, в7, В, 5 в and 8 mean hydrogen; ,(0-2 ю в Я (2 ех шчи (v. and where В7, В?, ВЗ 87 mean hydrogen; -- в ; (0-3) "7 not ez EE Re o s voev o de В", B", 85, B and BZ mean hydrogen, and 2? means hydrogen, halogen or C 4-alkyl; or вы; (0-6) E (22) called E: o ve o so schi З " where VZ, 87, 25, Kv and 8 are hydrogen, and B! means halogen. m. 2. Tetrazole derivatives of the general formula (I) according to claim 1, which differ in that B! means fluorine, chlorine, bromine, methyl, methylsulfonyl, ethylsulfonyl, methoxy, nitro- or cyano group, B2 means C. alkyl, cyclopropyl, C.sub.3-haloalkyl or C.sub.-alkenyl, "t is 1 or 2, while two substituents B! can be the same or different, if t is equal to 2, - n is equal to 1 or 2, с О means one of the following groups Из» in о; (0-1) in r - and ve a t» in Z (og) where VZ, 87, 25, 9. in and 8 mean hydrogen; so to (o) iChe) eh shchi (v. v (F; where 7, V?, E9 1 V mean hydrogen; ime) 60 b5 С Ш No ez EE Ee and Е Z where B", B, 859, B and 28 mean hydrogen, and Z means hydrogen, fluorine, chlorine, methyl or ethyl; or в! ; (0-6) Ee 5. V eE: ve o v z where Z, 7, 25, 5 v iv is hydrogen, V"! means chlorine or bromine. C. Tetrazole derivatives of the general formula (I) according to claim 1, which differ in that B! means chlorine, bromine, methyl or methylsulfonyl, c B2 means methyl, ethyl, n-propyl, isopropyl or cyclopropyl, o t equals 2 and in this case two substituents B attached respectively in position 2 and in position 4 of the benzene ring and two substituents 2! can be the same or different, n is equal to 1, the group o v2 co -(sna-8-K..1 its 5th "And 3o is attached in position C of the benzene cycle, and 0) means one of the following groups v i or a . Fe se - with Ge) ;" 4. Herbicidal composition, which is characterized by the fact that it contains at least one compound according to claim 1. 5. The herbicidal composition according to claim 4, which is characterized by the fact that it additionally contains at least one herbicidally active component selected from the group that includes fentrazamide, propanil, cafenstrol, -I oxacyclomefon, pretilachlor, mefenacet and indanophan. 6. The herbicidal composition according to claim 4, which is characterized by the fact that it additionally contains at least one antidote selected from the group consisting of dichlormid, dimron, fenchlorin, mefenpyr-diethyl and K-29148. Go! 7. The compound of the formula (X) (c), 0) se 70 (vi her s mi M. sno MA- where about B, B2, t and p are as defined in claim 1, M means hydroxyl, Si./ -Alkoxyl or group o o a-- b5