UA74566C2 - Herbicidal composition - Google Patents

Abstract

A herbicidal composition that, in addition to comprising customary inert formulation adjuvants, comprises: a) a compound of formula (I), wherein the substituents are as defined in claim 1; and b) a synergistically effective amount of one or more compounds of formulae (2.1 to 2.51). The compositions according to the invention may also comprise a safener. (I),

Description

Description of the invention

The present invention relates to a new herbicidal composition, which contains a combination of 2 herbicidally active ingredients and is suitable for selective control of weeds in crops of useful plants, for example corn. The invention also relates to a method of combating weed plants in crops of useful plants, as well as the use of the indicated new composition for these purposes. Compounds of the formula (0), item 6) in which the substituents have the following values, have herbicidal activity.

During the creation of the invention, it was unexpectedly established that the combination of active ingredients used in different amounts, that is, the combination of the active ingredient of formula I with one or more of the following active ingredients of formulas 2.1-2.51, which are known compounds and some of which are also commercially available products , reveals a synergistic effect, which allows using such a combination for effective control of most weeds, which are found primarily in crops of beneficial plants, both at the pre-germination stage and at the post-germination stage. oh

In accordance with this, the invention proposes a new composition that has a synergistic effect for selective weed control, which, in addition to the commonly used in the technology of preparation of preparative forms of inorganic auxiliary substances (adjuvants), contains as an active ingredient a mixture of cha a) herbicidal of the effective amount of the compound of the formula - и? 75 (I), -i i 1 zo M 42) t in which

K In each case independently means hydrogen, C1-Salkyl, C1-Swalkenyl, C10-Swhaloalkenyl, o C0-Swalkynyl, C0-Swhaloalkynyl, C3-Swcycloalkyl, C1-Swallowoxy, C1-Swhaloalkyl,

C-Swalkylthio group, C.i-Swalkylsulfinyl, C.--Swalkylsulfonyl, C.i-Swhaloalkyl, C.i-Swhaloalkylthio group, where C.i-Swhaloalkylsulfinyl, C.-Swhaloalkylsulfonyl, S.i-Swallowoxycarbonyl, C.-Swalkylcarbonyl ,

Si-Salkylamino group, di(Si-Salkyl)amino group, C4-Salkylaminosulfonyl, di(Si-Salkyl)aminosulfonyl, 60 0 -М(К1)-5-К», -М(К3)-5О-Ку/, -М (K5)-502-Ke, nitro group, cyano group, halogen, hydroxy group, amino group, benzylthio group, benzylsulfinyl, benzylsulfonyl, phenyl, phenoxy group, phenylthio group, phenylsulfinyl or phenylsulfonyl, while the phenyl group can in turn be mono-, di- or tri-substituted S.-Svalkilom,

C.i-Swhaloalkyl, C3z-Swalkenyl, C3-Swhaloalkenyl, C3-Swalkynyl, C3-Swhaloalkynyl,

C-Svaloxy group, C-Svhaloalkyl group, C3-Svalkenyloxy group, C3-Svalkynyloxy group, 65 mercapto group, C.i-Svalkylthio group, C.-Svhaloalkylthio group, C3-Svalkenylthio group,

C3-Shaloalkenylthio group, C3-Svalkynylthio group, C3-Svaloxyalkylthio group, C3-Cracetylalkylthio group,

C3-Salkyloxycarbonylalkylthio group, Co-C.cyanoalkylthio group, C.-Salkylsulfinyl,

C-Svhaloalkylsulfinyl, S.-Svalkylsulfonyl, C.-Svhaloalkylsulfonyl, aminosulfonyl,

C1-Soalkylaminosulfonyl, Co-C.dialkylaminosulfonyl, C.--Salkylene-Cl5 group, MEdeCad? group, Halogen, cyano group, nitro group, phenyl or benzylthio group, and the last two groups, which are phenyl group and benzylthio group, in turn can be substituted in the phenyl ring by C-Szalkyl, C-Szhaloalkyl,

C.-C-Alkoxy group, C.-C.-Ghalo-Alkoxy group, halogen, cyano group or nitro group, or

K in each case independently means a 5-10 membered monocyclic or fused bicyclic ring system, which may be aromatic or partially saturated and may contain from 1 to 4 heteroatoms selected from nitrogen, oxygen, and sulfur, wherein such ring system or directly attached to the pyridine ring, or attached to the pyridine ring through a C 1-C alkylene group, each ring system cannot contain more than two oxygen atoms and cannot contain more than two sulfur atoms, and the specified ring system can be mono- , di- or trisubstituted by C.-Svalkyl, C.-Svhaloalkyl, C3-Svalkenyl,

C3-Svhaloalkenyl, C3-Svalkynyl, C3-Svhaloalkynyl, C.i-Svaloxy group, C.-Svhaloalkyloxy group, 75 C3-Svalkenyloxy group, C3-Svalkynyloxy group, mercapto group, C.-Svalkylthio group,

C.i-Svhaloalkylthio group, C3-Svalkenylthio group, C3-Svhaloalkenylthio group, C3-Svalkynylthio group,

Co-Svaloxyalkylthio group, C3-Svaacetylalkylthio group, C3-Svaloxycarbonylalkylthio group,

Co-C.cyanoalkylthio group, C.-Salkylsulfinyl, C.-C.haloalkylsulfinyl, C.-Salkylsulfonyl,

Ci-Cshaloalkylsulfonyl, aminosulfonyl, C.i-Soalkylaminosulfonyl, Co-C.dialkylaminosulfonyl, 2o Ci-Csalkylene-K7 group, MKaCo»o group, halogen, cyano group, nitro group, phenyl or benzylthio group, and the phenyl and benzylthio group in turn can be substituted in the phenyl ring by S.--Szalkyl,

C.-Shaloalkyl, C.-Shaloalkyl, C.-Shaloalkyl, halogen, cyano group or nitro group, while the substituents near the nitrogen atom in the heterocyclic ring are different from halogen, or

Kk in each case independently means C.-Slalkoxy-C.--C;alkyl or sch

C1-C1-Alkoxy-C1-C,Alkoxy-C1-Alkyl, t means 1, 2, C or 4, (8)

Ku, Kz and K5 each independently of each other mean hydrogen or S.-Svalkil,

Ko means MK/oKi, C1-C1-Swallowoxy, C1-Swhaloalkyl, C1-Swalkyl, C4-Swhaloalkyl,

C3-Swhaloalkenyl, C3-Swhaloalkenyl, C3-Swalkynyl, C3-Swhaloalkynyl, C3-Swcycloalkyl or phenyl, while phenyl («Od zo Can in turn be substituted by C.i-Szalkyl, /C.-Swhaloalkyl, S.- szalkoxy group,

C-C3haloalkyl group, halogen, cyano group or nitro group, ise)

Ki stands for MK.2K.iz, C.sub.4-Cvhaloalkyl, C.i.Svhaloalkyl, C.4-Svhaloalkyl,

C3-Swalkenyl, C3-Swhaloalkenyl, C3-Swalkynyl, C3-Swhaloalkynyl, C3-Swcycloalkyl or phenyl, while the phenyl can in turn be substituted by C.i-Swalkyl, C.swhaloalkyl, C.sw.-Salkoxy group, "

C.-Shaloalkyl group, halogen, cyano group or nitro group, i-

Square; means | MK.AKiv, Ci-Svalkoxy group, C.i-Svhaloalkyl, C.i-Svalkyl, C.4-Svhaloalkyl,

C3-Swalkenyl, C3-Swhaloalkenyl, C3-Swalkynyl, C3-Swhaloalkynyl, C3-Swcycloalkyl or phenyl, while phenyl can in turn be substituted by C.i-Swalkyl, C.swhaloalkyl, C.sw.-Alkoxy group,

C.-Shaloalkyl group, halogen, cyano group or nitro group, "

K; and Kab each independently means a C.sub.1-Salkoxy group, a C.sub.-Slalkoxycarbonyl, a C.sub.-S.alkylthio group, a C.sub.-S.alkylsulfinyl, a C.sub.-S.alkylsulfonyl or phenyl, while phenyl may in turn be substituted by C. C-Salkyl, C-Shaloalkyl, C-Salkoxy group, C-Shaloalkyl group, halogen, ;" cyano group or nitro group,

Kv, Ko, Kch12, Ku44 and Kb each independently of each other means hydrogen or C.4-Svalkil,

Ko, K41, Kis, Ki5 and Ku7 each independently of each other means Si-Svalkyl or Si-Svalkoxy group, -and O means group 4 ih o p Kk 16 (22) and (01

Kk 20 vi o 19 18 o - in which vo Kiv, Ki7, Kiv and Klio each independently of each other means hydrogen, hydroxy group, C-i-Su; alkyl,

Co-Svalkenyl, Co-Svalkinyl, S.-C.Alkoxycarbonyl, S.-Svalkylthiogroup, S.i-Svalkylsulfinyl,

Si-Salylsulfonyl, group C--Slalkyl-MNV(O)", /C.4-Suhaloalkyl, -MH-S.i-Slalkyl, /-M(S.--Salalkyl)",

S.-Svaloxy group, cyano group, nitro group, halogen or phenyl, which can be substituted in turn

C.-Slalkyl, C.i-Slhaloalkyl, C.--Slalkoxy group, C.-Slhaloalukoxy group, /C.i-C;alkylcarbonyl, 65 C.-C.lalkoxycarbonyl, amino group, C.-C.alkylamino group, di( C1-Sulalkyl) amino group,

C.i-Svalkylthio group, C.-Svalkylsulfinyl, C1-Svalkylsulfonyl, C.-Slalkyl-5(0)20 group,

C.1-Chaloalkylthio group, C.-C.haloalkylsulfinyl, C.-Chaloalkylsulfonyl, group

C1-Shaloalkyl-5(0)20, C4-Slalkyl-Z(0)2MH, C4-Slalkyl-5(0)2M(C1-Sulfalkyl), halogen, nitro group, COOH group or cyano group, or two adjacent substituents with numbers Kv, Ki7, Kv and Ko form

So-Svalkylen bridge,

Kor means oshydroxy group, OM", halogen, C.-Sioalkyloxy group, /C4-Sioalkylcarbonyloxy group,

C.-C, alkenylcarbonyloxy group, C3-Seccycloalkylcarbonyloxy group, cC.-Ci»alkoxycarbonyloxy group,

C.-Sig2alkylcarbonyloxy group, K2g1Ko2i-SHO)0, C.-Sioalkylthio group, C.-Sioalkylsulfinyl,

C.1-C2alkylsulfonyl, C.-Chaloalkylthio group, C.1-C/haloalkylsulfinyl, C.-Suhaloalkylsulfonyl, 70. C0-C10alkenylthio group, C0-C10alkenylsulfinyl, C0-C10alkenylsulfonyl, C0-C10alkenylthio group,

Co-C.ohaloalkenylsulfinyl, Co-C-ohaloalkenylsulfonyl, Co-C-oalkynylthio group, Co-Ci2alkynylsulfinyl,

Co-Si2alkynylsulfonyl, C.-Slalkyl-5(0)20, phenyl-5(0)20, (C41-Salkoxy)2P(FOO,

C.i-Slalkyl(C1-Salkoxy)P(000, H(C.--Slalkoxy)P(0)0, C.-C15-alkyl-B(CO)O, benzyloxy group, phenoxy group, phenylthio group, phenylsulfinyl or phenylsulfonyl , while the phenyl group can in turn be substituted by 75 C.i.-Slalkyl, C.i.-Slalkyl, C.i.-Slalkoxy group, C.--Subhaloalukoxy group, /C.i-C;alkylcarbonyl,

C.-C.alkoxycarbonyl, C.i-C.alkylamino group, di(C1-Sulalkyl)amino group, C.i-Salkylthio group,

C.i-C.alkylsulfinyl, C4-C;alkylsulfonyl, C.i-Sualkyl-Z(0)2O0 group, / C.i-Suhaloalkylthio group,

C.1-C.haloalkylsulfinyl, C.-Chaloalkylsulfonyl, group C1-Chaloalkyl-5(0)20, group

C1-Slalkyl-5(0)2MH, Si-Slalkyl-5(0)2M(C41-Slalkyl), halogen, nitro group or cyano group, and

Co and Co" each independently of each other means hydrogen or S.-Sualkil or group 02

K 23 s (05), o o Te 7 in which x,

Koz means a hydroxy group, OM", a halogen, a C.-Sioalkyloxy group, a /C4-Sioalkylcarbonyloxy group,

C.-C, alkenylcarbonyloxy group, C3-Seccycloalkylcarbonyloxy group, cC.-Ci»alkoxycarbonyloxy group,

S.-Sig2alkylcarbonyloxy group, Co. KovIM-SO)O, S.-Sioalkylthio group, S.-Sioalkylsulfinyl, h

C1-C12alkylsulfonyl, C.-Shaloalkylthio group, C.1-C/haloalkylsulfinyl, C.-Subhaloalkylsulfonyl, -

Co-Si2alkenylthio group, Co-Si2-alkenylsulfinyl, Co-Si2alkenylsulfonyl, Co-Siohaloalkenylthio group,

Co-C.ohaloalkenylsulfinyl, Co-C10-haloalkenylsulfonyl, Co-C-oalkynylthio group, C»-C-2alkynylsulfinyl,

Co-Si2alkynylsulfonyl, C.-Slalkyl-5(0)20, phenyl-5(0)20, (C41-Salkoxy)2P(FOO, "

C.i-Slalkyl(C1-Salkoxy)P(000, H(C.--Slalkoxy)P(0)0, C.-C15-alkyl-B(CO)O, benzyloxy group, phenoxy group, phenylthio group, phenylsulfinyl or phenylsulfonyl , while the phenyl group can in turn be substituted - with C.-Slalkyl, C.-Sl-haloalkyl, C.--Slalkoxy group, C.-Slhaloalukoxy group, /C.i-C;alkylcarbonyl, and C.-S. lalkoxycarbonyl, C.i-C.alkylamino group, di(C1-Sulalkyl)amino group, C.i-Salkylthio group, "» C.i-C.alkylsulfinyl, C4-C;alkylsulfonyl, C.i-Sulalkyl-Z(0 )2O0, / C.i-Suhaloalkylthio group,

C.1-C.haloalkylsulfinyl, C.-Chaloalkylsulfonyl, C1-Chaloalkyl-5(0)20 group, C-Slalkyl-5(O)2MH group, C4-Slalkyl-5(0)2M (C1-Sulalkyl), a halogen, a nitro group, or a cyano group, -and Code and Kv each independently of each other means hydrogen or C.-Alkyl and 1»U means oxygen, sulfur, a chemical bond or a C.-C; alkylene bridge, or an Oz group 1 b ) Ko Re 44 42) r

Kc with (05),

ID or name)

Aza Kv because in which one

Kal, Ka, Kzv and Kzo each independently of each other means hydrogen, C-Salkyl, C.4-Svhaloalkyl,

Co-Svalkenyl, Co-Svalkinyl, S.i-Svaloxycarbonyl, S.-Svalkylthiogroup, S.i-Svalkylsulfinyl,

Si-Svalkylsulfonyl, Si-Svalkyl-MNOZ(O)", Si-Svalkylamino group, di(Si-Svalkyl)amino group, hydroxy group,

C.i-Svaloxy group, C3-Svalkenyloxy group, C3z-Svalkynyloxy group, hydroxy-C.4-Svalkyl, because C.-C.alkylsulfonyloxy-C /-Svalkyl, tosyloxy-C.i-Svalkyl, halogen, cyano group, nitro group, phenyl or phenyl,

substituted by C.-C.alkyl, C.-Sulfaloalkyl, C.i.-Salkoxy group, C.i.-Shaloalkyl group,

C.-Slalkylcarbonyl, C.-C. alkoxycarbonyl, amino group, C1-Salkylamino group, di(C.i-C.alkyl)amino group, C.i-Sdalkylthio group, C.i-Salkylsulfinyl, C.i-Salkylsulfonyl, group 50 C1-Salkyl-5(O0)20, C1-C1-haloalkylthio group, C1-C1-haloalkylsulfinyl, C-C1-haloalkylsulfonyl, C1-C1-haloalkyl-C(0)20 group, C1-C1-haloalkyl-5(0)2MH group , C.-Svalkylthio-(C.4-Su;alkyl),

C-Salkylsulfinyl-M(C 4-Slalkyl), C-Salkylsulfonyl-M(C .-Slalkyl), halogen, nitro group, group

COOH or a cyano group or adjacent Ku substituents; and Kz" or Kzv and Kzo jointly represent themselves

C3-Svalkylene, 70 M means oxygen, sulfur, sulfinyl, sulfonyl, -СКу4Клд»-, -С(0)- or -МЕДз-,

Ky stands for hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy-C1-C6 alkyl, C1-C6 alkylthio-C1-C6 alkyl,

C.-C.alkylcarbonyloxy-C 1-Su;alkyl, C.-Slalkylsulfonyloxy-C -Su;alkyl, tosyloxy-C1-Sulalkyl, di(C1-Salkoxyalkyl)methyl, di(Ci-Salkylthioalkyl)methyl, (C41- Szalkoxyalkyl)-(C -Szalkylthioalkyl)methyl,

C3-Svoxacycloalkyl, C3-Sthiacycloalkyl, C3-Sldioxacycloalkyl, C3-C.dithiacycloalkyl, 75. C3-Soxathiacycloalkyl, formyl, C--Slalkoxycarbonyl or phenyl, which may in turn be substituted

C.-Slalalkyl, C.i-Ci-haloalkyl, C.--Slalkyoxy group, C.-Silhaloalukoxy group, /C.i-C;alkylcarbonyl,

C.-C.alkoxycarbonyl, amino group, C.-C.alkylamino group, di(C1-Sulalkyl)amino group,

C.i-Salkylthio group, C.-Salkylsulfinyl, C1-Salkylsulfonyl, C.-Salkyl-5(0)20 group,

C.1-Chaloalkylthio group, C.-C.haloalkylsulfinyl, C.-Chaloalkylsulfonyl, group 20. C1-Chaloalkyl-3(0)20, group C.-Clalkyl-5(0)2MH, C.-Calalkylthio-(C .4-Cu;alkyl),

C-Salkylsulfinyl-M(C 4-Slalkyl), C-Salkylsulfonyl-M(C .-Slalkyl), halogen, nitro group, group

COOH or a cyano group, or Ku" together with Kzo form S.-Svalkilen,

Ka" means hydrogen, C41-Su;alkyl or C.-Su/haloalkyl,

Kalo means a hydroxy group, OM", a halogen, a C.-Sioalkyloxy group, a /C4-Sioalkylcarbonyloxy group, a C.-C.alkenylcarbonyloxy group, a C.3-Seccycloalkylcarbonyloxy group, a C.-Ci»alkylcarbonyloxy group, o

C.-Sig2alkylcarbonyloxy group, KovCo;M-C(O)0, C.-Sioalkylthio group, C.-Sioalkylsulfinyl,

C.1-C2alkylsulfonyl, C.-Shaloalkylthio group, C.1-C/haloalkylsulfinyl, C.-Subhaloalkylsulfonyl,

Co-Si2alkenylthio group, Co-Sioalkenylsulfinyl, Co-Si2alkenylsulfonyl, Co-Siohaloalkenylthio group,

Co-C.ohaloalkenylsulfinyl, Co-C-ohaloalkenylsulfonyl, Co-C-oalkynylthio group, Co-Sioalkynylsulfinyl, "0

Co-C12alkynylsulfonyl, C.-Slalkyl-5(0)20, phenyl-5(0)20, (C4-Slalkoxy)2P (00,

C.i-Slalkyl(C,-Sdalkoxy)P(0)0, H(C.-Slalkoxy)P(0)0, C.-Sioalkyl-B(CO)O, benzyloxy group, phenoxy group, n-o phenylthio group, phenylsulfinyl or phenylsulfonyl, while the phenyl group may in turn be substituted by M

C.-Slalalkyl, C.i-Ci-haloalkyl, C.--Slalkyoxy group, C.-Silhaloalukoxy group, /C.i-C;alkylcarbonyl,

C.-C.alkoxycarbonyl, C.i-C.alkylamino group, di(C1-Sulalkyl)amino group, C.i-Salkylthio group, C

C1-Slalkylsulfinyl, S.--Slalkylsulfonyl, C.i-Sulalkyl-Z(0)2O0 group, / C.i-Suhaloalkylthio group, i-

C.1-C.haloalkylsulfinyl, C.i-Slaloalkylsulfonyl, group C.-Subhaloalkyl-Z(O)20, group

C.i-Slalkyl-B(O)2MH, C--Slalkyl-5(0)2M (C1-Sualalkyl), halogen, nitro group or cyano group,

Kov and Ko7 each independently of each other mean hydrogen or S.-Sualkil, "

C is hydrogen, C 1 -C 1 alkyl, C 1 -C 1 alkyl oxycarbonyl or phenyl, which may in turn be substituted with C 1 -C 1 alkyl, C 1 -C 1 haloalkyl, C 1 -C 6 alkyl, C 1 -C 1 haloalkyl, /C.--C;alkylcarbonyl, - with C.-C.lalkoxycarbonyl, C.i-C.alkylamino group, di(C1-Sulalkyl)amino group, C.i-Salkylthio group, and C.i-C.alkylsulfinyl, C4 -C;alkylsulfonyl, C.i-Sualkyl-Z(0)2O0 group, / C.i-Suhaloalkylthio group, "» C.1-C.haloalkylsulfinyl, C.-Chaloalkylsulfonyl, C1-Chaloalkyl-5(0)20 group , a group

S.i-Slalkyl-B(O)2MH, C--Slalkyl-5(0)2M (C1-Sualalkyl), halogen, nitro group or cyano group, or the group Od t v iz Ko) sl Kk 33

FO 50 and in o M'

F) Kk 35 name) in which

Kzo means an oshydroxy group, OM", a halogen, a C-Ci-Ci-Ci-Alkoxy group, a C4-CiO-alkylcarbonyloxy group, a C-Ci-Alkenylcarbonyloxy group, a C-Ci-Seccycloalkylcarbonyloxy group, a C-Ci-Ci-Ci-Alkoxycarbonyloxy group,

C.-Sig2alkylcarbonyloxy group, Kz31K321ch-(O)0, C.-Sioalkylthio group, C.-Sioalkylsulfinyl,

C.1-C2alkylsulfonyl, C.-Shaloalkylthio group, C.1-C/haloalkylsulfinyl, C.-Subhaloalkylsulfonyl,

C2-C12alkenylthio group, Co-Ci»alkenylsulfinyl, Co-Ci»alkenylsulfonyl, Co-Ci»haloalkenylthio group,

Co-C.ohaloalkenylsulfinyl, C.-C-ohaloalkenylsulfonyl, C.-C-oalkynylthio group, C.4-Ci2alkynylsulfinyl, because C.-Sioalkynylsulfonyl, C.-Slalkyl-5(0)20, phenyl-5(0)20 , (C41-Salkoxy)2P(FOO,

C.-Slalkyl(C1-C;Alkoxy)P(00, H(C--Slalkoxy)P(O0)0, C1-Sioalkyl-B(CO)O, benzyloxy group, phenoxy group, phenylthio group, phenylsulfinyl or phenylsulfonyl, while the phenyl group may in turn be substituted

C.-Slalalkyl, C.i-Ci-haloalkyl, C.--Slalkyoxy group, C.-Silhaloalukoxy group, /C.i-C;alkylcarbonyl,

C.-C.alkoxycarbonyl, C.i-C.alkylamino group, di(C1-Sulalkyl)amino group, C.i-Salkylthio group,

C.i-C.alkylsulfinyl, C4-C;alkylsulfonyl, C.i-Sualkyl-Z(0)2O0 group, / C.i-Suhaloalkylthio group,

C.1-C.haloalkylsulfinyl, C.i-C.haloalkylsulfonyl, group C.-C.haloalkyl-5(0)20, group

C.i-Slalkyl-B(O)2MH, C--Slalkyl-5(0)2M (C.1-Svalkylom), halogen, nitro group or cyano group,

Kz and Kz" each independently of each other means hydrogen or C-Salalkyl, 70 Kz3z3 and K3z4 each independently of each other means hydrogen, a hydroxy group, C--Slalkyl, Co-Swalkenyl,

Co-Svalkynyl, S.-S.Alkoxycarbonyl, S.-Svalkylthiogroup, S.-Svalkylsulfinyl, S.-Svalkylsulfonyl,

Ci-Slalkyl-MNOZ(O)», Ci-Suhaloalkyl, -MH-Si-Sulfalkyl, -M(S.i-Sulalkyl)», C--Sulfoxy group, cyano group, nitro group, halogen or phenyl, which can be alternately substituted with C 4-Alalkyl, C.--C/haloalkyl,

C1-Slalkyloxy group, C1-C1-haloalkyl group, C1-Slalkylcarbonyl, C-Slalkoxycarbonyl, amino group, 75. C1-Slalkylamino group, di(C1-Sulalkyl)amino group, C1-Salkylthio group, C1-Salkylsulfinyl,

C1-Salkylsulfonyl, C.i-C;alkyl-Z(0)2O group, C.-Subhaloalkylthio group, C.i-C/haloalkylsulfinyl,

C.1-C.haloalkylsulfonyl, C.-Suhaloalkyl-Z(O)20 group, C.-Slalkyl-5(0)2MH group,

C.-Slalkyl-5(0)2M (C1-C alkyl), halogen, nitro group, COOH group or cyano group, or Kz3zz and Kz/ jointly form a Co-Salkylene bridge, and

Cz5 represents hydrogen, C-Slalkyl, C-Slalkoxycarbonyl or phenyl, which may in turn be substituted

C-C alkyl, C-C alkyl, C-C alkyl, C-C/halo-alkyl, C-C alkylcarbonyl,

C.-C.alkoxycarbonyl, amino group, C.-C.alkylamino group, di(C1-Sulalkyl)amino group,

C.i-Salkylthio group, C.-Salkylsulfinyl, C1-Salkylsulfonyl, C.-Salkyl-5(0)20 group,

C.1-Chaloalkylthio group, C.-C.haloalkylsulfinyl, C.-Chaloalkylsulfonyl, C1-Chaloalkyl-C(0)20 group, C4-Calalkyl-5(0)2MH group, C-Calalkyl-5(0) group 2M(C1-Slalkyl), a halogen, a nitro group, a COOH group or a cyano group, and) or a group OB "-K o "so

LEK (05 o'clock

Wow! and

Kk z o v. in which 7 stands for sulphur, BO or 50", "

KO1 means hydrogen, C-Salkyl or C-Salkyl substituted by halogen, C-C-Alkoxy group, C-C-Alkylthio group, C-C-Alkylsulfonyl, C-Alkylsulfinyl, hydroxy group, cyano group, C with nitro group , the group -CHO, the group -СО2Ко», the group -СОКоз, the group -СО5Кой, the group -МКоБКой, the group "» СОМКОозеКоз or a phenyl, which can be substituted in turn by С--Slalkyl, C.4-Svhaloalkyl, " Si- C.alkoxy group, C.i-Suhaloalkyloxy group, Co-Svalkenyl, C3-Svalkynyl, C3-Svalkenyloxy group,

C3-Alkynyloxy group, halogen, nitro group, cyano group, -COOH group, СООС.1-C.alkyl, COOphenyl, C.-C.Alkoxy group, phenoxy group, (C41-Slalkoxy)-C.--Slalkyl, (C4-Salalkylthio) -C4-C; alkyl, - (C4-C.alkylsulfinyl)-C 4-Slalkyl, (C41-Slalkylsulfonyl)-C 4-C/alkyl, MNZO»-C1-C;alkyl, their MNZO»-phenyl, M (C1-Salkyl)5O25-Si-C;alkyl, M(C1-C8)alkyl)3O»-phenyl,

M(C-Svalkenyl)305-C.-Sualalkyl, M(Co-Svalkenyl)5O"-phenyl, M(C3-Svalkynyl)3O5-C.4-Su;alkyl, o M(C3-Svalkynyl)5O"- phenyl, M(C3-C6cycloalkyl)ZO2-C.4-C; alkyl, M(C3-Ccycloalkyl)ZO»-phenyl,

Ge" 20 M(phenyl)5O"-C.4-Sudalkyl, M(phenyl)5O"-phenyl, O5O5-C4-Slalkyl, group СОМКоО25КОз2в,

Oo5O2-C1-Shaloalkyl, O5O»-phenyl, C.i-C; alkylthio group, C.i-Sugaloalkylthio group, phenylthio group, m.

C.-C/lhaloalkylsulfinyl, phenylsulfinyl, C-C;alkylenephenyl or the group -МКой15С2О5Ко27, or

Co means Co-Salkenyl or Co-Salkenyl substituted by halogen, C.-Sallkoxy group, 5o C.-Salalkylthio group, C1-Salylsulfonyl, C.i-Sallkylsulfinyl, -SOMCO32Bozz group, cyano group,

HF) nitro group, -CHO group, -СО2Козв group, -СОКозо group, -СО5-С4-С; alkyl, -МКосаКозв group or phenyl, which in turn can be replaced by С 4-С; alkyl, С--Свhaloalkyl, C.--C;Alkoxy group, o C1-Suhaloalkyloxy group, Co-Svalkenyl, C3-Svalkynyl, C3-Svalkenyloxy group, C3-Svalkynyloxy group, halogen, nitro group, cyano group, group -СООН, СООС.-Slalkyl, COOphenyl, С.-- Slalkoxy group, 60 phenoxy group, (C4-Salkoxy)-C1-C; alkyl, (C4-Salalkylthio)-C4-C; alkyl, (C4-C.alkylsulfinyl)-C 4-Slalkyl, (C41-Slalkylsulfonyl)-C 4 -C/alkyl, МНЗО»-С1-С;alkyl,

МНЗО»-phenyl, M(С4-Svalkyl)5О»-С.4-Sulalkyl, M(С1-Svalkyl)5О»-phenyl,

M(C»-Svalkenyl)5O25-C14-Sulalkyl, M(C»-Svalkenyl)5O»-phenyl, M(C3-Svalkynyl)u5O»-C1-C; alkyl,

M(C3-Svalkynyl)5O"-phenyl, M(C3-Cscycloalkyl)ZO2-C.4-C; alkyl, M(C3-Ccycloalkyl)ZO"-phenyl, because M(phenyl)5O2-C4-Sulfalkyl, M (phenyl)5O»-phenyl, OoBO-C.1-Sualkyl, the SOMColoColi group,

Oo5O-Ci-Suhaloalkyl, O5O»-phenyl, C.i-C; alkylthio group, C.i.-Suhaloalkylthio group, phenylthio group,

C-Alkylsulfonyl, C-Sulfaloalkylsulfonyl, phenyl sulfonyl, C-C,-alkylsulfinyl,

C.-C.haloalkylsulfinyl, phenylsulfinyl, C.-C.alkylenephenyl or the group -MKol"3ССО»Cod»o, or

Which means C3-Svalkynyl or C3-Svalkynyl substituted with halogen, C1-C4haloalkyl, cyano group, -CO», or phenyl, which may in turn be substituted with C1-C4alkyl, C1-C4haloalkyl, Si -Slalkoxy group,

C1-Suhaloalkyloxy group, Co-Svalkenyl, C3-Svalkynyl, C3-Svalkenyloxy group, C3-Svalkynyloxy group, halogen, nitro group, cyano group, -СООН group, СООС.-Slalkyl, COOphenyl, C--Slalkoxy group, phenoxy group, (C4-Salkoxy) -C1-C; alkyl, (C4-Salalkylthio)-C4-C; alkyl, 70. "C1-Slalkylsulfinyl)-C 1-Slalkyl, (C41-Slalkylsulfonyl)-C 4-C/alkyl, M5O"-C4- Slalkill,

МНЗО»-phenyl, M(С4-Svalkyl)5О»-С.4-Sulalkyl, M(С1-Svalkyl)5О»-phenyl,

M(C-Svalkenyl)305-C.-Sulfalkyl, M(Co-Svalkenyl)5O»-phenyl, M(C3-Svalkynyl)3O5-C.4-Sulfalkyl,

M(C3-Svalkynyl)5O"-phenyl, M(C3-Ccycloalkyl)ZO2-C.4-C;alkyl, M(C3-Ccycloalkyl)ZO"-phenyl,

M(phenyl)5O025-C14-Slalkyl, M(phenyl)5O»-phenyl, O505-C4-Slalkyl, SOMCoO2vCogo group, 7/5 05O2-Si-Slhaloalkyl, O5O»-phenyl, S.i-Sulalkylthio group, S. i-Subhaloalkylthio group, phenylthio group,

C-Alkylsulfonyl, C-C-haloalkylsulfonyl, phenylsulfonyl, C-C,-alkylsulfinyl,

C.-C.haloalkylsulfinyl, phenylsulfinyl, C.-C.alkylenephenyl or the group -Mkoz1CO»Cozo, or

Which means C53-C5-C6 cycloalkyl or C3-C6-C6 cycloalkyl substituted by C1-C6 alkyl, C1-C6 alkyl,

C.-Slalkylthio group, C.-Slalkylsulfinyl, C--Slalkylsulfonyl or phenyl, which can in turn be substituted by halogen, nitro group, cyano group, C.-Slalkoxy group, C.-Slalkyloxy group,

C.-Salalkylthio group, C.i-Shaloalkylthio group, C.--C.alkyl or C.-C.sub.haloalkyl, or

Which means C1-C6 alkylene-C3-C6 cycloalkyl, phenyl or phenyl substituted with C1-C6 alkyl, C1-C6 haloalkyl,

C-C-Alkoxy group, C-C-Alkyloxy group, Co-Svalkenyl, C3-Svalkynyl, C3-Svalkenyloxy group,

C3-Salkynyloxy group, halogen, nitro group, cyano group, -СООН group, СООС.1-C.alkyl, COOphenyl, sch dv C1-Slalkoxy group, phenoxy group, (C41-Slalkoxy)-C.--Slalkyl, (C4-Slalkylthio)- C4-C alkyl, (C4-C alkylsulfinyl)-C 4-C alkyl, (C41-C alkylsulfonyl)-C 4-C alkyl, MNZO»-C 1-C alkyl, and)

MNBZO»-phenyl, M(C1-Svalkyl)5O2-С14-Slalkyl, M(С4-Svalkyl)5O»-phenyl,

M(C-Svalkenyl)305-C.-Sulfalkyl, M(Co-Svalkenyl)5O»-phenyl, M(C3-Svalkynyl)3O5-C.4-Sulfalkyl,

M(C3-Svalkynyl)5O"-phenyl, M(C3-Ccycloalkyl)ZO2-C.4-C;alkyl, M(C3-C7cycloalkyl)5O-phenyl, "o zo M(phenyl)5O2-C4-Slalkyl, M(phenyl)5O»-phenyl, OoBO-S.1-Sualkyl, the group SOMKOol5KOdv,

Oo505-C41-Alhaloalkyl, O5O»-phenyl, C-Alalalkylthio group, C.--Sulfaloalkylthio group, phenylthio group, etc.)

C-Alkylsulfonyl, C-C-haloalkylsulfonyl, phenylsulfonyl, C-C,-alkylsulfinyl,

C.-C/haloalkylsulfinyl, phenylsulfinyl or the group -МКолвСО»од7, or

Koi means C.-C.alkylenephenyl, SOKO7 or 4-6-ene heterocyclyl, -

Co", Cosv, Col4 and Covv each independently of one another means hydrogen, C4-C6 alkyl, phenyl or phenyl, substituted with C1-C1 alkyl, C1-C1-haloalkyl, C1-C1-C6 alkyl, C1-C1-C /haloalkyl group, Co-Svalkenyl,

C3-Svalkynyl, C3-Svalkenyloxy group, C3-Svalkynyloxy group, halogen, nitro group, cyano group, group -СОоон, СООС1-С,alkyl, СООphenyl, С.и-С;alkoxy group, phenoxy group, (С-4-С;alkoxy)- C.i-C;alkyl, (C4-C.alkylthio)-C4-C;alkyl, (C.4-C.alkylsulfinyl)-C.4-Slalkyl, (C.41-C.alkylsulfonyl)-C.1-C;alkyl, "

МНЗО2-С1-Sуалкілом, МНЗО»-phenyl, M(С1-Svalkyl)5О025-С.4-Slalkylom, M(Si-Svalkyl)ZO»o-phenyl, st») with M(С-Svalkenyl)305-С .-Sualalkyl, M(Co-Svalkenyl)5O»-phenyl, M(C3-Svalkynyl)3O5-C.4-Su;alkyl, . M(C3-Svalkynyl)5O"-phenyl, M(C3-Ccycloalkyl)ZO2-C.4-C; alkyl, M(C3-Ccycloalkyl)ZO"-phenyl, and M(phenyl)5O025-C.4-Sulalkyl , M(phenyl)5O»-phenyl, OoBO-C1-Svalkyl, by the SOMKoloKovo group;

Oo505-C41-Salhaloalkyl, O5O»-phenyl, C-Sallkylthio group, C.--Suhaloalkylthio group, phenylthio group, 45. C1-Salkylsulfonyl, C.1-C/haloalkylsulfonyl, phenylsulfonyl, C1-Salkylsulfinyl, -I C.-S/ haloalkylsulfinyl, phenylsulfinyl, -С--С; alkylphenyl or the group -МКов2СО»Ковз,

Koz, Kozo and Kovu each independently means C1-C6 alkyl, phenyl or phenyl substituted with C1-C6 alkyl, C1-C8haloalkyl, C1-C1-Salkoxy group, C1-C1-C1-Alkoxy group, Co - Svalkenyl, with C3-Svalkynyl, C3-Svalkenyloxy group, C3-Svalkynyloxy group, halogen, nitro group, cyano group, 5o СООН group, СООС. ,

Me. (C4-Salkylthio)-C4-C;alkyl, (C4-C.alkylsulfinyl)-C 4-Salalkyl, (C41-C.alkylsulfonyl)-C 1-C;alkyl,

Ф МНЗО»-С.-Sulalkyl, МНЗО»-phenyl, M(C1-Svalkyl)5О025-С.4-Slalkyl, M(С1-Svalkyl)5О»-phenyl,

M(C-Svalkenyl)305-C.-Sulfalkyl, M(Co-Svalkenyl)5O»-phenyl, M(C3-Svalkynyl)3O5-C.4-Sulfalkyl,

M(C3-Svalkynyl)5O»-phenyl, M(C3-Ccycloalkyl)ZO2-C.4-C;alkyl, M(C3-Ccycloalkyl)ZO»-phenyl, two M(phenyl)5O2-C4-Slalkyl, M (phenyl)5O»-phenyl, OoBO-C.1-Sualkyl, by the group of SOMKOovaKova,

Oo5O-Ci-Suhaloalkyl, O5O»-phenyl, C.i-C; alkylthio group, C.i.-Suhaloalkylthio group, phenylthio group,

Ф) C-Clalalkylsulfonyl, C1-C1-haloalkylsulfonyl, phenylsulfonyl, C1-C1-alkylsulfinyl, and C.-C/lhaloalkylsulfinyl, phenylsulfinyl, -""СНо)-phenyl, where Iy has a value from 1 to b or the group -МКовеСО" Kovv, vo Kol means S. Sualkil,

Cob means hydrogen, C 1 -C 1 alkyl, C 3 -Salkylenyl, C 3 -Salkylenyl, C 3 -C cycloalkyl, phenyl or substituted phenyl

C.i-C; alkyl, C.-Ci-haloalkyl, C.i-Salkoxy group, C.i-Ci-haloalkyl group, Co-Svalkenyl,

C3-Svalkynyl, C3-Svalkenyloxy group, C3-Svalkynyloxy group, halogen, nitro group, cyano group, group -СОоон, СООС1-С,alkyl, СООphenyl, С.и-С;alkoxy group, phenoxy group, (С-4-С;alkoxy)- C.i-C;alkyl, 65 "C1-Cdylalkylthio)-Ci1-Sulalkyl, (C1-Cdylalkylsulfinyl)-C 1-C;alkyl, (C4-C.alkylsulfonyl)-C 1-C;alkyl,

MNZO»-S.-Sulalkyl, MNZO»-phenyl, M(С1-Svalkyl)5О025-С.4-Slalkyl, M(С1-Svalkyl)5О»-phenyl,

M(C-Svalkenyl)305-S.-Sualkyl, M(C»-Svalkenyl)ZO»-phenyl, group M(Sz-Svalkenyl)ZO2H,

M(C3-Svalkynyl)5O»5-C14-Sualalkyl, M(C3-Svalkynyl)u3O»-phenyl, the group M(C3-Sucycloalkyl)ZO2H,

M(C3-Ccycloalkyl)5O5-C14-Sualkyl, M(C3-Ccycloalkyl)ZO»-phenyl, M(phenyl)5O5-C4-C; alkyl,

M(phenyl)5Oo-phenyl, O5O2-C1-Slalalkyl, SOMKov7Kovv group, O5O2-C4-Slhaloalkyl, 8OzO»-phenyl,

C.i-Salkylthio group, C.-C.haloalkylthio group, phenylthio group, C.-Slalkylsulfonyl,

C.1-C.haloalkylsulfonyl, phenylsulfonyl, C.1-Alkylsulfinyl, C.-Slhaloalkylsulfinyl, phenylsulfinyl, C.1-Salkylenephenyl or -MKovoSO»Kovo group,

Kov means hydrogen, C 1 -C 1 alkyl, C 3 -Salkylenyl, C 3 -Salkylenyl, C 3 -C cycloalkyl, phenyl or 7/O-substituted phenyl. C1-Cdalkyl, C-C6haloalkyl, C1-Salkoxy group, C1-C1-Alkyloxy group, Co-Svalkenyl,

C3-Svalkynyl, C3-Svalkenyloxy group, C3-Svalkynyloxy group, halogen, nitro group, cyano group, group -СОоон, СООС1-С,alkyl, СООphenyl, С.и-С;alkoxy group, phenoxy group, (С-4-С;alkoxy)- C.i-C;alkyl, (C4-C.alkylthio)-C4-C;alkyl, (C.4-C.alkylsulfinyl)-C.4-C.alkyl, (C.41-C.alkylsulfonyl)-C.1-C;alkyl,

МНЗО»-С1-Sulalkyl, МНБЗО»-phenyl, M(С4-Svalkyl)3О»-С1-Salalkyl, M(С4-Svalkyl)5О»-phenyl, 75. MSH(С2-Svalkenyl)5О2-С4-Svalkyl, M(Co-Svalkenyl)5O»-phenyl, M(C3-Svalkynyl)3O5-C.4-Su;alkyl,

M(C3-Svalkynyl)5O"-phenyl, M(C3-Ccycloalkyl)ZO2-C.4-C;alkyl, M(C3-Ccycloalkyl)ZO"-phenyl,

M(phenyl)5O025-C.4-Sulalkyl, M(phenyl)5O»-phenyl, OoBO-C.1-Sulalkyl, by the SOMKOv1Kovo group,

Oo5O-Ci-Suhaloalkyl, O5O»-phenyl, C.i-C; alkylthio group, C.i.-Suhaloalkylthio group, phenylthio group,

C-Alkylsulfonyl, C.1-C/haloalkylsulfonyl, phenylsulfonyl, C1-Alkylsulfinyl,

C1-Slhaloalkylsulfinyl, phenylsulfinyl, C--Slalkylenephenyl or the -MKovaSO»Rovz group,

Co means phenyl, C41-C; alkyl, C--C; alkoxy group or -MKovCoo,

Kov and Coo each independently represent C1-C6 alkyl, phenyl, or phenyl substituted with halogen, nitro, cyano, C1-C6 alkyl, C1-C6 alkoxy, C1-Sthioalkyl, -СО2Ков, by the group -бОКов7, C-Slalkylsulfonyl, C.--Slalkylsulfinyl, or C.-Svlhaloalkyl, or Kov and Koo together form a 5- or b-membered ring, which can be interrupted by oxygen, the MKovv5 group or atom 5,

Cat, Goz1, Col3; Kav, Kovo, Kovv; Covo and Covi each independently of each other mean hydrogen, C4-Sualkyl, and)

Co-Svalkenyl, C3-Svalkynyl or C3-SUcycloalkyl,

Kogv, Kogv; Kog7t; Kogv» Kogo, Kozo, Koz2» Kozz» Koza, Kozv, Kozv; Kozt" Circle; Kol1; Number 2; Codv, Codv, Col» Colo,

Koko, Kovz, Kova, Kovv, Kov?, Kovv, Kovo, Kovi, Kovo, Kovz, Kov5 and Kovv each independently of each other mean Ge) of hydrogen, S.-Slalkil, So-Swalkenil, Sz-Swalkinil, Sz- C7cycloalkyl, phenyl or phenyl substituted with a halogen, nitro group, cyano group, C1-Slalkoxy group, C1-Shaloalkyl group, C1-Slalkylthio group, etc.)

C.-Cihaloalkylthio group, C.i.-C.alkyl or C.-Cihaloalkyl, and

Kzv stands for C1-C6alkyl, C1-C6haloalkyl, C3-Swhaloalkyl, C3-Swhaloalkenyl, C3-Swhalkynyl, C3-Swhaloalkynyl,

C3-Svcycloalkyl or C3-Svcycloalkyl substituted by halogen, C4-C;alkyl, C1-C1haloalkyl, C3-Svalkenyl, -

Зз5 C3-Swhaloalkenyl, C3-Swalkynyl, C3-Swhaloalkynyl, C.-S.Alkoxycarbonyl, S.--Swalkylthio group, y-

C.i-C.alkylsulfinyl, C.-C.3alkylsulfonyl, C.-Subhaloalkylthio group, C.-C.haloalkylsulfinyl,

C.1-C.haloalkylsulfonyl, C.-Alkylcarbonyl, di(C1-Sulalkyl)amino group, C.i-Salkoxy group,

C.-Cihaloalkyl group, C.i-C;alkyl-Z(0)20 group, C.-Cihaloalkyl-5(O)2O group or phenyl, which can be replaced by halogen, C--Cialkyl, C- 4-C/lhaloalkyl, C3-Svalkenyl, C3-Svalkenyl, "Cyano group, nitro group or COOH group, with c or an agronomically acceptable salt of such a compound and . b) a synergistically effective amount of one or more compounds selected from the group consisting of the compound of formula 2.1 - ех х | e t - M in 2 Rg IR - (2.1)

Me with 4) we -5 about Me

F) in which K5i means CHO-OMe, ethyl or hydrogen, and Ko» means hydrogen or Kb. and Ko" together mean the group ka -Сн-сн-сн-сн., the compound of formula 2.2 60 b5

Kz

M:

M (2.2), then u- Ssn.s! "what; in which Kz means ethyl, Cod means methyl or ethyl, and Co5 means -"CH(Me)-CHNOMe, "55-CH(Me)-CHNOMe, 75 snoOMe or СНоО-СНоCH", a compound of formula 2.3

Me

Re (2.3), d

Me 9

What (Ce) zo in which Kob means CH(Me)-SNNOMe or "55CH(Me)-SNNOMe, a compound of formula 2.4 ise)

IS)

Kk, -

XX century

MOhm (2.4), "

Kk r Kk 2 al sh- Ba s M M M . » - and in which K57 means chlorine, a methoxy group or a methylthio group, Kov means ethyl, and Kevo means ethyl, isopropyl, -Ф«СМХ(СН»)-СН» or tert-butyl, sh» a compound of the formula 2.5 ий ох b 50 42 )

Ko 00 (2.5), (F, with Kv; o; 60 in which Ko means ethyl or n-propyl, Kv4 means СОО 1/2сСа", -СН.-СН(Me)5-СНоСН» or group с " and

X means oxygen, М-О-СНСН» or М-О-СНСН-СН-СИ, the compound of the formula 2.6 b5 g v x // y ti p

M (2 b) with o Ot va

R is

Co in which Co" means hydrogen, methoxy or ethoxy, Kvz means hydrogen, methyl, methoxy or fluorine,

Kwa4 means COOMEe, fluorine or chlorine, Keo5 means hydrogen or methyl, U means methine, C-E or nitrogen, 7 means methine or nitrogen, and Cob means fluorine or chlorine, the compound of formula 2.7 ra Kv, i. t o o

She (2 7), "I | with you

M. la

M SI « h- in which Ke7 means hydrogen or -С(0)-5-n-octyl, the compound of formula 2.8 « du vin. - с :» Kv Rv from (2.8), -I t» 1 bu 20 sim 4) in which Kov means bromine or iodine, the compound of formula 2.9 (F) ko bo b5 o Ko Vo o 8. // "Me 8; t in which Kvo means chlorine or a nitro group, a compound of formula 2.10

Ko o » In a dream,

M

SI M also (2.19), y

M Me o)

Ky in which K7o means fluorine or chlorine, and K71 means -СНО-СН(СИ)-СООСНОСН" or -"МН-5О»Me, ix, the compound of formula 2.11 "со

Me v ho " 5 ko i m. oo o v (2.11), 5 t2 s :" Oh y, - o -I sh" not in which K/7" means trifluoromethyl or chlorine, 1 compound of formula 2.12 b 50 o

R SOoon r 5 Me" I" (2.12), 2; about t K 13

MN. 60 4 in which K7z means МН" or "52МН", the compound of the formula 2.13 b5 u o u 4 7 lo Z o

MK OO78 yu l s o MO,

Н Н т in which ХУ means nitrogen, methine, МН-СНО or М-Ме, Mo means nitrogen, methine or С-Й, 3 means methine, Ху means methine or Uz and M; together means sulfur or C-CI, M5 means nitrogen or methine, M means methyl, difluoromethoxy group, trifluoromethyl or methoxy group, 7 means methoxy group or difluoromethoxy group, and K74 means СОММе», СООМе, СООС»ОНв, trifluoromethyl, СНо-СНоСЕ3З or 505СНоСН3, or its sodium salt ("Me" in each case means a methyl group), a compound of the formula 2.13.c o sn, and

SI o sh x - SN o o Z

Mrya tsi te 7 tp- - od 2. - » m Mn m " (2.13.0), F o | H (se)

СН, A. Ж шт СН, ю о и Мо « m. compound of formula 2.14

Me m-m Me / U Ye ikh zo Me 5 2 s o m-n '

V. N t compound of formula 2.15 1 c) N.M SI 42)

О.Мо) 2 with (2.15, (Ф, име) 60 compound of formula 2.16 b5 re av ; НоОс ч РО(ОН), (2.16), d compound of formula 2.17

Yi Kh

IR Me io (2.17), still mm | at

H compound of the formula 2.18 is also used

Me M-o0 » LA to her

Me M (2.15), y « /7 y- r y

Mo Me "shchi Me shi s compound of formula 2.19 g" SI sh 45 m soon (2.19), 1 b 50

Ф с ОоМе compound of formula 2.20 о ю Me АХ E! where) va M v7 o (2.20),

Me Me b5 Me compound of formula 2.21 o

SI where SE,

M

/ h o o Me me, / (2.21),

Ho

Me 8; with o

Н, Ф with the compound of formula 2.22

With " m. "

Y chi 022 5 s g a Me sh 45 Me their compound of formula 2.23 and (i b 50 42) o M obon ko compound of formula 2.24

EE oyu o o o (2.24), no (8; 20 ra n-pentyl compound of formula 2.25 with E o

SI M Te)

U-k (2.25), y

Z M - y; t i - meros o "du compound of the formula 2.26 with - /Me 7 se, Nm sh 45 o sh"

UA (226), b 50 42) o.

F) the compound of formula 2.27

E O yu ; m; (2.27), o; in not

M compound of formula 2.28

And Mem and Khume (2.28), with the compound of formula 2.29 o

SI in |se)

IC o)

M "

S M Z c. " 2.29 o ( i ), " t s ;" / nn -I 1" compound of formula 2.30 and 50 me

Shy M-M

M (2.30),

A ra ovo E o o o compound of formula 2.31

SI

SA

M M 2.31), kh "U 3 y m--:M S

Me 715 compound of formula 2.32

E Vg

SE,

mine

SI "4

M m "m s » 732), o o o Te

Me--5 th

Me « h- compound of formula 2.33

Her nose is HER 5

Fo in Mme--8:-Me (2.33, "from on

I Me compound of the formula 2.34 -I sh» to NM U o MnSO,сН, (2.34), b 50

F compound of formula 2.35

SE, - M o sn Ya (2.35), name) bo Si o compound of formula 2.36 n

AND

SNU M.O lx (2-36),

And its 70 o o C(СНу). the compound of the formula 2.37 with («78 сн,Н(сН)) is the compound of the formula 2.38 sch de / M. i СНЕ, о with снвос Л- совсн, (2.38, it сн,сН(СН.), compound of the formula 2.39 and sn, (SNU,M M o « " My 2.39 7 s M. M (2.39),

I» and o -I t. the compound of formula 2.40

FS chnsomsn,) b 50 2 iy (2.40),

SI compound of formula 2.41

F) "with Osn,so,N zo 2772 (241),

CH, the compound of the formula 2.42 sn,

And with U OSNO (242) '

CH, compound of formula 2.43 iz 8 (сНуо-К З in MсOMНеН, my (2.43), compound of formula 2.44 ns. CH, 7 o o -

SN.SI » ; (2.44), F

IS) « with base.sn, m compound of formula 2.45 « o o o o -

Гв) and вв MD

And" not M m-- CH,

I in not (2.45), in CHI 1 sn, (o) 20 compound of formula 2.46 yy o o "zopropyl o Na M with M 2.46

And their p (2.46), p

SE; and Bg is a compound of formula 2.47 o ; osn.sn, o -- si (2.47), so» o compound of formula 2.48 i they KO (2.48)

IS . z y s o us AH ise) o sn, yu o - the compound of the formula 2.49 i-

IS

Sleep, oh, "

Z s IR -m-M-AI m ;z» | ee Н H (2.49), ato E

Her still but (about)

Ф compound of formula 2.50 I sn, neck

F) yu sn oo Y well o

CH, X-CH. 9 mn,

and the compound of formula 2.51 about Sn; WITH

IS

S M H E x y M- E o (2.51. o; Sn

With Fr. -

In the above formulas, "Me" means a methyl group. The alkyl groups indicated above in the values of the substituents may be branched or straight chain and are, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl , octyl, nonyl, decyl, c ob undecyl and dodecyl, as well as their branched isomers. Alkoxy, alkenyl, and alkynyl radicals are derivatives of the above-mentioned alkyl radicals. Alkenyl and alkynyl groups can be singly or multiply i) unsaturated.

The alkylene group can be replaced by one or more methyl groups, and such alkylene groups are preferably unsaturated in each case. The same applies to all C 3-Svcycloalkyl-, Ge

C3-Svoxacycloalkyl-, C3-Sthiacycloalkyl-, C3-C.dioxacycloalkyl-, C3-C/dithiacycloalkyl-,

C3-Sloxathiacycloalkyl- and MSH(CH")-containing groups. ise)

Halogen usually means fluorine, chlorine, bromine or iodine. The same is correspondingly true for halogen, which is part of various groups, such as haloalkyl or halophenyl.

Haloalkyl groups that have a chain length of 1 to b carbon atoms are, for example, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, n-2-chloroethyl, pentafluoroethyl , 1,1-difluoro-2,2,2-trichloroethyl, 2,2,3,3-t-etrafluoroethyl and 2,2,2-trichloroethyl, pentafluoroethyl, heptafluoro-n-propyl, perfluoro-n-hexyl, at the preferred haloalkyl groups indicated in the values of the substituents K o, Kz and first of all (Ko, are trichloromethyl, dichlorofluoromethyl, difluorochloromethyl, difluoromethyl, trifluoromethyl, pentafluoroethyl or heptafluoro-n-propyl. "

Suitable haloalkenyl radicals are alkenyl groups, singly or multiply substituted with a halogen, which is fluorine, chlorine, bromine or iodine and primarily fluorine or chlorine, for example 2,2-difluoro-1-methylvinyl. Z-fluoropropenyl, Z-chloropropenyl, Z-bromopropenyl, 2,3,3-trifluoropropenyl, 2,3,3-trichloropropenyl and others? 4,4,4-trifluorobut-2-en-1-yl. Preferable Co-Si»alkenyl radicals, mono-, di- or tri-substituted by halogen, have a chain length of 2 to 5 carbon atoms. Suitable haloalkynyl radicals are alkynyl groups mono- or multiply substituted by halogen, which is bromine or iodine and -I is primarily fluorine or chlorine, for example 3-fluoropropynyl, 3-chloropropynyl, 3-bromopropynyl, 3,3,3-trifluoropropynyl and 4 ,4,4-trifluorobut-2-yn-1-yl. Preferred alkynyl groups, mono- or multiply substituted by halogen, have a pi chain with a length of 2 to 5 carbon atoms. c Alkoxy groups preferably have a chain length of 1 to b carbon atoms. As an example of an alkoxy group, methoxy-, ethoxy-, propoxy-, isopropoxy-, n-butoxy-, isobutoxy-, sec-butoxy- or

Me. tert-butoxy group or pentyloxy or hexyloxy isomer, with methoxy and ethoxy groups being preferred.

F Alkylcarbonyl is preferably acetyl or propionyl. Examples of methoxycarbonyl are methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl, or tert-butoxycarbonyl, with methoxycarbonyl, ethoxycarbonyl, or tert-butoxycarbonyl being preferred.

Haloalkoxy groups preferably have a chain length of 1 to 8 carbon atoms. As examples (F, haloalkoxy groups can be called fluoromethoxy group, difluoromethoxy group, trifluoromethoxy group, ka 2,2,2-trifluoroethoxy group, 1,1,2,2-tetrafluoroethoxy group, 2-fluoroethoxy group, 2-chloroethoxy group, 2,2-difluoroethoxy group or 2,2 ,2-trichloroethoxy group, while the difluoromethoxy group is preferred, because the 2-xporethoxy group or the trifluoromethoxy group.

Alkylthio groups preferably have a chain length of 1 to 8 carbon atoms. Examples of the alkylthio group are methylthio, ethylthio, propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio or tert-butylthio, with methylthio or ethylthio being preferred.

Alkylsulfinyl is, for example, methylsulfinyl, ethylsulfinyl, propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, isobutylsulfinyl, sec-butylsulfinyl or tert-butylsulfinyl, preferably methylsulfinyl or ethylsulfinyl.

Alkylsulfonyl is, for example, methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl or tert-butylsulfonyl, preferably methylsulfonyl or ethylsulfonyl.

An alkylamino group is, for example, a methylamino group, an ethylamino group, an n-propylamino group, an isopropylamino group, or an isomer of butylamine. The dialkylamino group is, for example, a dimethylamino group, a methylethylamino group, a diethylamino group, an n-propylmethylamino group, a dibutylamino group, or an isopropylamino group. Alkyl amino groups with a chain length of 1 to 4 carbon atoms are preferred.

Alkoxyalkyl groups preferably have from 1 to 6 carbon atoms. Examples of alkoxyalkyl include 7/0 Mmethoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, n-propoxymethyl, n-propoxyethyl, isopropoxymethyl or isopropoxyethyl.

Alkylthioalkyl groups preferably have from 1 to b carbon atoms. Examples of alkylthialkyl include methylthiomethyl, methylthioethyl, ethylthiomethyl, ethylthioethyl, n-propylthiomethyl, n-propylthioethyl, isopropylthiomethyl, isopropylthioethyl, butylthiomethyl, butylthioethyl or butylthiobutyl.

Cycloalkyl groups preferably have from 3 to 6 ring carbon atoms and may be substituted by one or more methyl groups, but unsubstituted cycloalkyl groups, such as cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, are preferred.

Phenyl, including as a structural fragment of one or another substituent, such as a phenoxy group, benzyl, benzyloxy group, benzoyl, phenylthio group, phenylalkyl, phenoxyalkyl or tosyl, can be present in mono- or polysubstituted form, while the substituents, depending on specific requirements, can be in ortho-, meta- and/or para-position(s).

The scope of this invention also includes salts of compounds of formula I, which these compounds can form with amines, alkali and alkaline earth metal bases, or quaternary ammonium bases. Among the hydroxides of alkali and alkaline earth metals used as salt-forming agents, the hydroxides of lithium, sodium, potassium, magnesium and calcium, primarily sodium and potassium hydroxides, should be singled out.

As an example of amines suitable for the formation of ammonium salts, we can mention ammonia, as well as primary, (8) secondary and tertiary C4-C-valkylamines, C.4-Suhydroxyalkylamines and Co-C;alkoxyalkylamines, such as methylamine, ethylamine, n- propylamine, isopropylamine, four isomers of butylamine, n-amylamine, isoamylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, heso methylethylamine, methylisopropylamine, methylhexylamine, methylhexylamine, methylpentadecylamine, ethyloctylamine, ethyloctylamine ethyloctylamine, hexylheptylamine, hexyloctylamine, ix, dimethylamine, diethylamine, di-n-propylamine, diisopropylamine, di-n-butylamine, di-n-amylamine, diisoamylamine, dihexylamine, digeptylamine, dioctylamine, ethanolamine, n-propanolamine, isopropanolamine, M ,M-diethanolamine,

M-ethylpropanolamine, M-butylethanolamine, allylamine, n-butenyl-2-amine, n-pentenyl-2-amine, « 2,3-dimethylbutenyl-2-amine, dibutenyl-2-amine, n-hexenyl-2-amine , propylenediamine, trimethylamine, triethylamine, n-tri-n-propylamine, triisopropylamine, tri-n-butylamine, triisobutylamine, tri-tert-butylamine, tri-n-amylamine, methoxyethylamine and ethoxyethylamine, heterocyclic amines such as pyridine, quinoline, isoquinoline, morpholine, piperidine, pyrrolidine, indoline, quinuclidine and azepine, primary arylamines such as anilines, methoxyanilines, ethoxyanilines, o0-, m- and p-toluidines, phenylenediamines, benzidines, naphthylamines and o-, m- and p-chloroanilines , but "primarily triethylamine, isopropylamine and diisopropylamine. with с During the creation of the invention, it was unexpectedly established that the effect of using a combination of the active ingredient of the formula | with one or more active ingredients from among the compounds of formulas 2.1-2.51;" exceeds in the fight against weeds the total effect, which in principle should be expected from the use of such active ingredients separately, thanks to which the spectrum of action of each of these individual active ingredients is expanded, first of all, taking into account the following two aspects. The first of them consists in reducing -I consumption rates of individual compounds of formulas I and 2.1-2.51 while simultaneously maintaining their action at a fairly high level, and the second consists in the fact that the composition proposed in the invention makes it possible to carry out the fight against weeds with high efficiency even in those cases when the use of individual compounds in small doses is impractical and ineffective from an agronomic point of view. As a result, it is possible to significantly expand the spectrum of weedy plants with which it is necessary to fight, and to additionally increase the selectivity in

Me. the ratio of crops of useful plants, which is a necessary condition for accidental overdose of the active ingredient

F ingredient. The composition proposed in the invention not only ensures highly effective destruction of weeds in crops of useful plants, but also provides great freedom in the choice of crops that are expected to be cultivated in the next crop on the same sown areas. 5B The composition proposed in the invention can be used to control a wide range of agronomically important weed plants, such as Zieliiagia, Maziipit, Aadgoviiz, Oidnagia, Amepa, Zeigia, (F) Zipariv, Iot, Zoiapit, Razeoii5, Espipospioa, Zsigriv, Mopospogia .

Spgyzapipetit, Saiisht, Mioia | Megopis The composition according to the invention allows its use by all methods commonly used in agriculture, and is, in particular, suitable for pre-germination treatment, post-germination treatment and seed treatment. The composition proposed in the invention is suitable for weed control primarily in crops of such useful plants as grain crops, rapeseed, sugar beet, sugar cane, plantation crops, rice, corn and cultivated soybeans, as well as for non-selective control of weed plants . 65 "Crops" in the context of this invention also mean crops in which, as a result of traditional breeding methods or genetic engineering, tolerance to herbicides or their entire classes has been produced.

Preferred compositions according to the invention contain compounds of formula I, in which

K In each case independently means hydrogen, C.i-Svalkyl, Co-Svalkenyl, C»o-Svhaloalkenyl,

Co-Svlkynyl, Co-Svhaloalkynyl, C3-Svcycloalkyl, C.i-Svlkoxy group, C.-Svhaloalkyl group, O C-Svalkylthio group, C--Svalkylsulfinyl, C.--Svalkylsulfonyl, C.-Svhaloalkyl, /C.-Svhaloalkylthio group,

C.i-Cvhaloalkylsulfinyl, C.-Cvhaloalkylsulfonyl, C.i-Cvalkyloxycarbonyl, C.-Cvalkylcarbonyl,

C-Salkylamino group, di(C-Salkyl)amino group, C.--Salkylaminosulfonyl, di(C.--Salkyl)aminosulfonyl, -M(K4)-5-K2, -M(K3)-50-K;, - M(K5)-5O02-Ke, nitro group, cyano group, halogen, hydroxy group, amino group, benzylthio group, benzylsulfinyl, benzylsulfonyl, phenyl, phenoxy group, phenylthio group, phenylsulfinyl or 7/0 phenylsulfonyl, while the phenyl group can in turn be mono-, di- or trisubstituted by S.-Svalkil,

C.i-Swhaloalkyl, C3z-Swalkenyl, C3-Swhaloalkenyl, C3-Swalkynyl, C3-Swhaloalkynyl,

C-Svaloxy group, C-Svhaloalkyloxy group, C3-Cv-alkenyloxy group, C3-Svalkynyloxy group, mercapto group, C.i-Svalkylthio group, C.-Svhaloalkylthio group, C3-Svalkenylthio group,

C3-Svhaloalkenylthio group, C3-Svalkynylthio group, C3-Svaloxyalkylthio group, C3-Svacetylalkylthio group,

C3-Cv-Alkoxycarbonylalkylthio group, Co-C.cyanoalkylthio group, C.-Salkylsulfinyl,

C-Svhaloalkylsulfinyl, S.-Svalkylsulfonyl, C.-Svhaloalkylsulfonyl, aminosulfonyl,

C1-Soalkylaminosulfonyl, Co-C.dialkylaminosulfonyl, C.--Salkylene-Cl5 group, MEdeCad? group, halogen, cyano group, nitro group, phenyl or benzylthio group, and the last two groups, which are phenyl and benzylthio, in turn, can be substituted in the phenyl ring by C-Salkyl, C.4-Shaloalkyl,

a C1-C3-alkyloxy group, a C1-C3-haloalkyl group, a halogen, a cyano group or a nitro group, or

K in each case independently means a 5-10 membered monocyclic or fused bicyclic ring system which may be aromatic or partially saturated and may contain from 1 to 4 heteroatoms selected from nitrogen, oxygen and sulfur, wherein such ring system is either directly attached to the pyridine ring, or attached to the pyridine ring through a C 1-C alkylene group, each ring system cannot contain more than two oxygen atoms and cannot contain more than two sulfur atoms, and the indicated ring system can be mono-, di- or trisubstituted by C.-Svalkyl, C.-Svhaloalkyl, C3-Svalkenyl, and)

C3-Swhaloalkenyl, C3-Swhalkynyl, C3-Swhaloalkynyl, C.i-Swhaloxy group, C.-Swhaloalkyl group,

C3-Svalkenyloxy group, C3-Svalkynyloxy group, mercapto group, C.-Svalkylthio group,

C.i-Cvhaloalkylthio group, C3-Svlkenylthio group, C3-Svhaloalkenylthio group, Cz-Svlkynylthio group, "o

Co-Svaloxyalkylthio group, C3-Svaacetylalkylthio group, C3-Svaloxycarbonylalkylthio group,

Co-C.cyanoalkylthio group, C1-Salkylsulfinyl, C1-Shaloalkylsulfinyl, C1-Salkylsulfonyl, ise)

C-Svhaloalkylsulfonyl, aminosulfonyl, C.i-Soalkylaminosulfonyl, Co-C.dialkylaminosulfonyl, C.-S.alkylene-K7 group, MKaCo group, halogen, cyano group, nitro group, phenyl or benzylthio group, and phenyl and benzylthio group in turn can be substituted in the phenyl ring by S.--Szalkyl, "

C.-Shaloalkyl, C.sub.-Shaloalkyl, C.-Shaloalkyl, halogen, cyano group or nitro group, while Ku, Ko, Kz, Ku, Kv, Kv, K7, Kv, Ko, Kv, Kv and Kl7 have the above value, and the substituents near the nitrogen atom in the heterocyclic ring are different from halogen.

Another group of preferred compositions according to the invention includes compositions which, as a compound of formula I! contain a compound of the formula IIa "o - c;" e 49 chЦШЩ 0 (Ia), - their rai is Kv M Ve b 50 in which schi Klv means C.i-Salkyl, Co-Salkylenyl, Co-Swhaloalkenyl, Co-Swalkynyl, Co-Swhaloalkynyl, C3-Swcycloalkyl,

C.-Alhaloalkyl or a 5-10 membered monocyclic or fused bicyclic ring system which may be aromatic or partially saturated and may contain from 1 to 4 heteroatoms selected from nitrogen, oxygen and sulphur, 252 such ring system being either directly attached to pyridine ring, or attached to

HF) of a pyridine ring through a C.1-C alkylene group, each ring system cannot contain more than two oxygen atoms and cannot contain more than two sulfur atoms, and the specified ring system can in turn be mono-, di- or tri-substituted C .i-Svalkyl, C.i-Svhaloalkyl, C.i-Svalkenyl, Cz-Svhaloalkenyl, Cz-Svalkynyl,

C3-Cvhaloalkynyl, C-Cvalkyloxy group, C3-Cvhaloalkyloxy group, C3-Cvhaloalkyloxy group, 60 Cv-Cvhalokynyloxy group, mercapto group, C-Cvalkylthio group, C-Cvhaloalkylthio group,

C3z-Svalkenylthio group, C3-Shaloalkenylthio group, C3-Svalkynylthio group, Co-Svaloxyalkylthio group,

C3-Svacetylalkylthio group, C3-Svaloxycarbonylalkylthio group, Co-C.cyanoalkylthio group,

C-Cvalkylsulfinyl, C.i-Cvhaloalkylsulfinyl, C-Cv-alkylsulfonyl, C4-Cvhaloalkylsulfonyl, aminosulfonyl, C.--Soalkylaminosulfonyl, Co-C/dialkylaminosulfonyl, the C.-Cvalkylene-K»7 group, because the MEvKo group, halogen, a cyano group, a nitro group, a phenyl or a benzylthio group, while the phenyl and benzylthio group, in turn, can be substituted in the phenyl ring by C-C alkyl, C-C alkyl,

C.-S-Alkoxy group, C.--Shalo-Alkoxy group, halogen, cyano group or nitro group, and the substituents near the nitrogen atom in the heterocyclic ring are different from halogen,

C 10 means hydrogen, C 1-6 alkyl, C 1-6 haloalkyl, halogen, or phenyl, which may be substituted

C.-S-alkyl, C-C-haloalkyl, C-C-salkoxy group, C.--Cs-haloalkyl group, halogen, cyano group or nitro group,

Keo means S.-Svhaloalkyl and

K», Kv, K»e and O have the above values. 70 Among this group of compounds, compounds in which CC 48 stands for Si-Svalkyl, Co-Svalkenyl,

Co-Swhaloalkenyl, Co-Swalkynyl, Co-Swhaloalkynyl, C3-Socycloalkyl or C1-Swhaloalkyl.

Compositions in which |. in the formula are also preferred C) means the group OO" or Oz, where primarily in the group 0" Koz means a hydroxy group, and in the Oz group Ko also means a hydroxy group. Among this group, compounds in which t is equal to 2, and one substituent K is Co 4-Slalkoxy-C--Slalkyl or 75. C1-Slalkoxy-C--Slalkoxy-C.i-Sualkyl should be singled out.

Other preferred mixtures according to the invention, which have a synergistic effect, contain as active ingredients the compound of formula I and or the compound of formula 2.2.

Mi (2.2.a, ak 5 5(-UM-(1'-methyl-2-x, methoxyethyl)-M-chloroacetyl-2-sch in not CH»OOCH. ethyl-b-methylaniline), o.n. , CH, or a compound of formula 2.2.0 (Ce)

SN "co

With you

СО)СН. SI « / Czech (2.2.0), | 2 C si c or a compound of the formula 2.2, in which Kz means ethyl, Ku means methyl, and K5 means ethoxymethyl, or a compound of the formula 2.2, in which Kz means ethyl, Ku means ethyl, and B5 means methoxymethyl, or a compound of the formula 2.3, or w- a compound of formula 2.30, or a compound of formula 2.4, or a compound of formula 2.13, or a compound of formula 2.14, or their compound of formula 2.6, in which Ko means hydrogen, 7 means methine, Kis means methyl, U means nitrogen, K14 means fluorine, o Cub means hydrogen and K/b means or fluorine K./o” means methoxy group, 7 means methine, Kis means b 20 methoxy group, U means methine, K.4 means chlorine, K/5 means methyl and K/6 means chlorine, or a compound of the formula 2.1, in which K 47 means -C(0)-5-n-octyl, or a compound of the formula 2.12, or a compound of the formula 2.18, or a compound of the formula 2.19, or a compound of the formula 2.21, or a compound of the formula 2.25 , or a compound of formula 2.33, or a compound of formula 2.45, or a compound of formula 2.1.

Particularly preferred mixtures according to the invention, which have a synergistic effect, contain as active ingredients 29 the compound of formula I and or the compound of formula 2.2.4

С(О)-СН.СИ 2 ' ' и / (2.2.a, aqv5.1'5(-)M-(1'-methyl-

E Zh and 2'-methoxyethyl)-M- sh- - cha (already noC--CHuosn, Chloroacetyl 2-ethyl-b methylaniline), b5 s,n. CH,

or a compound of the formula 2.2.0 sn, /co)sn,c 70 x ( ish. U, non--snoOs n. and sn. CH, or a compound of the formula 2.2, in which Kz means ethyl, Ku means methyl, and K5 means ethoxymethyl, or a compound of formula 2.2, in which Kz is ethyl, Ku is ethyl, and K5 is methoxymethyl, or a compound of formula 2.3, or a compound of formula 2.30.

The most effective, as it was found, are combinations of compounds of formula I with a compound of formula 2.2a sn,

С(0)-СН.СИ / 7 1 ' ' s in M (2.2a, ak5, 1 5(-)M-(1-methyl-2"- o

M, methoxyethyl)-M-chloroacetyl-2-pettenoosH, ethyl-b-methylaniline) (Ce)

СОН, сн, (Се) at the same time as a compound of the formula | it is most preferable to use compound 1.001, indicated below in Table 1.

Compounds of the formula | can be obtained similarly to the method described in MO 97/46530, "a) by the interaction of compounds of the formula II-" with X. » p (I), z sh» s M c

FO ( ) t 42) in which K and t have the values indicated above for formula I! value, and X means a group that is removed, for example halogen, in an inert organic solvent in the presence of a base with a compound of the formula II, IM, M or MI o o A in A with the name) in (PP), (M),

And also vi o e p 17 v5 19 18

Kk 40 Y V z d K z3

In (UT 70 o 0 M 7

Kz K zv ' in Z5 where K»2o, Koz, Kzo and Kdo mean a hydroxy group, and the other substituents have the values indicated above for the formula I, to obtain a compound of the formula MII, MIP, YX or X

U she 2 I/ Z Yup "she s eE 46 o) (UP) F with (c) V. F

K 18 Kk 18 her

M - i in (Kp zh « t so oto (UP), it -I t» slob o b 50 4) (F, ko 60 b5

That " ah)

Ka IX), and in 37 o U

Ko zv (Kp sht s o

K zz (C), oyu and s om her o M z | -

K 35 and subsequent isomerization of this compound, for example, in the presence of a base and a catalytic amount of "dimethylaminopyridine (DMAP) or in the presence of a cyanide source, or b) by the interaction of a compound of the formula XI with 5 o;"

In ON sh»

F (XI), b 50 m.

M (K o t ime) su y . . in which K and t have the values indicated above for the formula I! value, with a compound of the formula I, IM, M or MI in an inert organic solvent in the presence of a base and a coupling agent to obtain a compound of the formula MIII, MP, IIX or X and subsequent isomerization of this compound, for example, according to the method described above for option a) .

Compounds of formula I, in which O represents the group Ov b5

2nd floor " X / M (05,

K ze o where 7 means sulfur, and Kzv and Koch have the values specified above for formula I, can be obtained analogously to known methods (described, for example, in UUO 97/43270), or a) by converting the compound of formula XI (Kt

Kk ze (ХП), o o M in which Kzv, K and t have the above values, in the presence of a base, carbon disulfide and an alkylating agent of the formula ХЙЙ с о

Ki-Hi (XII), in which Koi has the values specified above for formula 1, and X.; means a withdrawing group, such as a halogen or sulfonate, in a compound of the formula ХМ (в)т о о й

IS) « | Co. (KHIM), ich-

M

Kue 01 With c in which 7 is sulfur, and K, Ko, Kzv and t have the above values, and then cyclization of this compound :z" with hydroxylamine hydrochloride, optionally in a solvent, in the presence of a base to obtain a compound of the formula Ie o Yak - And their she ( in khm Ie), and (Kut ische

FU 5 o

M

42)

Kz in which 2 means sulfur, and K, Kzv, Koi and t have the values indicated above, followed by oxidation of this compound with a suitable oxidant, for example, zetia-chloroperbenzoic acid (m-KPBK).

GF) The method of obtaining compounds of the formula | illustrated in more detail in the 7 reaction schemes 1 and 2 below. 60 b5

Reaction scheme 1

Option a): (8) and x base, e.g. (S.Ne)ziM, I I SHIM, M or MI - "E R I I I I L R RO MY, MIP, IH, or x is a solvent, e.g. SN.SI, then M o-1102s

AND

: . 8) isomerization: a base, e.g. (С.Н)ЬМ, и и т. cat. M

WITH

Variant would be: o c base, e.g. (S.N). M, agent o t on Sh, IM, M or M KASH MI, MIH, or X (v)itt | - connection, ex

M e.g. paradise

ХИ Г no s o sn, ise) solvent, e.g. SN»SI. ю 0-110-С « isomerization: о m- base, e.g. (SON), dr (6; -.-- (Kt cha

KOM cat. M « | shi s. . yes, yes, yes. According to the above reaction scheme, it is possible to obtain, first of all, compounds of the formula |, which contain groups С, ФО, Оз and Оу, in which Коо, К2з, К2о and Клдо mean a hydroxy group.

Reaction scheme 2 8) -I o r koso, Vosh, that o v t- - i, Not a solvent, e.g. DMF, or | 26

KR/АЗа КИ X still 50 tm and SHIELD m 5 A and solvent, e.g. SN.SM, or

Mekhi Mman/sv5,, in, X,, with KHIM

HA! that the solvent, e.g. DMSO (9) 7 91 (V)t 9) z--V re ts

ГФ) МН., ОН . Her, the basis, e.g. І A (ОІ, e.g. m-ХИПБК (К)т - I M ---- - -НШНШФІВНЦНЧТЧТХТЮТЯТОЯ M o ko mabAses,n,On em in a solvent, e.g. SN.SI, shchen ze Ie 60 if 2 means ZSk or 50, if 7 means 5

To obtain compounds of formula I, in which OO is one of the groups C) 4-0, and K»2o, Koz, Kzo and Klo mean a hydroxy group, as starting materials are used according to reaction scheme 1, option a), derivatives of carboxylic acids of the formula II, in which X is a leaving group, for example a halogen, such as iodine, bromine or above all chlorine, M-oxyphthalimide or M,O-dimethylhydroxylamino, or a residue in the form of an activated ester, for example (obtained from

He; o-dicyclohexylcarbodiimide (Dddyu and an acceptable carboxylic acid) or (obtained from M-ethyl-M'-(3-dimethylaminopropyl)carbodiimide o- (EDK) and an acceptable carboxylic acid). These compounds in an inert organic solvent such as a halogenated hydrocarbon such as dichloromethane, a nitrile such as acetonitrile, or an aromatic hydrocarbon such as toluene and in the presence of a base such as an alkylamine such as triethylamine, an aromatic amine such as pyridine or 4-dimethylaminopyridine (DMAP), are subjected to interaction with dione derivatives of the formulas Ш, IM, М or MI to obtain isomeric enol ethers of the formulas MI, МШ, ХХ and Хх, respectively. Esterification occurs at a temperature from 0 to 11026.

Isomerization of ester derivatives of formulas МИЙ, MI, ИЙХ and Х to obtain dione derivatives of formula I (in which K»2or, Koz, Kzo and Kdo mean a hydroxy group) can be carried out, for example, similarly to the method described in EP 0369803 in the presence of a base, for example alkylamine , such as triethylamine, a carbonate such as potassium carbonate, and a catalytic amount of DMAP or in the presence of a cyanide source such as acetone cyanohydrin or potassium cyanide.

According to the reaction scheme 1, option b), the necessary diones of the formula I (in which K»o, Koz, Kzo and Kdo mean a hydroxy group) can be obtained, for example, analogously to the method described in |Spet. Gay. 1045 (1975))|, by esterification of carboxylic acids of formula XI with dione derivatives of formula I, IM, M or MI in an inert solvent such as a halogenated hydrocarbon such as dichloromethane, a nitrile such as acetonitrile, or an aromatic hydrocarbon such as toluene , in the presence of a base such as an alkylamine such as triethylamine and a coupling agent such as 2-chloro-1-methylpyridinium iodide. Depending on the solvent used (He) 3o, esterification is carried out at a temperature from 0 to 11022 with the formation initially, as described for option a), an isomeric complex ester of formula I, which can be subjected to isomerization, as indicated for option a), and, for example, in in the presence of a base and a catalytic amount of DMAP or in the presence of a cyanide source to obtain the necessary dione derivatives of the formula I! (in which K»o, Koz, Kzbo and K4o mean a hydroxy group).

Compounds of formula I, in which O represents the group O5, can be obtained according to the reaction scheme C 2 by the method described, for example, in IZupipevziz 301 (1991), page 4. 793 (1988) or in Temgapeidgop 32, 3055 r- (1976)), by the interaction of the p-diketone derivative of formula XI! with carbon disulfide in the presence of a base such as a carbonate such as potassium carbonate, a metal hydride such as sodium hydride or potassium fluoride on aluminium, and an alkylating agent of formula XI wherein X4 is a leaving group such as a halogen such as iodine, " bromine or primarily chlorine, K"50O5050-, SNUZO"O- or - This reaction - - sn; 50, o- and? preferably carried out in a solvent, for example in an amide such as M,M-dimethylformamide (DMF), a sulfoxide such as dimethyl sulfoxide (DMSO), or a nitrile such as acetonitrile. The ketenethioacetal of the formula CHM, which is formed in this process, is cyclized using hydroxylamine hydrochloride in the presence of a base, for example, sodium acetate, in a solvent, for example, in an alcohol, such as ethanol, or in an ether, such as tetrahydrofuran, to give a compound of the formula Ie, in which 7 means 5-. The cyclization reaction is carried out at a temperature of about 50 °C to 100 °C. The compound of formula Ie (7 means 5) can, if necessary, be oxidized in accordance with standard methods using, for example, peracids such as meta-chloroperbenzoic acid II; (m-HPEK) or peracetic acid, obtaining the corresponding sulfones and sulfoxides of the formula Ie (7 means 5O- or 5O2-), while the degree of oxidation of the sulfur atom (7 means 50- or 505-) can be adjusted using an oxidizing agent in the appropriate amount.

Oxidation to the compound of the formula Ie (7 means 5О- or 5О05-) is carried out according to the method described, for example, in

GF! IN.O. New, "Modet 5Bupipeiiys Keasiyope", edition of MU. A. Vepiatipp, Ips., Mapio Ragk, Saiyogpia, 1972, p. 334-335 and 353-354). o Activated derivatives of carboxylic acids of the formula II, which is presented in the reaction scheme 1 (variant a)) and in which X represents a leaving group, for example a halogen, such as bromine, iodine or above all chlorine, can be obtained according to known standard methods, for example, according to the method described in |S Regiti, "Keakiopep deg ogdapizspep Zupipeze", ed. beogu Tpiete Megiad, Bishchodag, 1978, p. 461 et seq.), and presented in the following reaction scheme 3. b5

Reaction scheme 3 o o (K)t (Angle x

ON flies, DM rat, x U Uh, DMF 70 nya -- 2 2 x B; ShK Mr. M

M 20-1502С "

XI

According to reaction scheme C, a compound of formula II, in which X is a leaving group, or of formula PI, in which X is halogen, is prepared, for example, using a halogenating agent, for example, a thionyl halide, such as thionyl chloride or -bromide, phosphorus halide or a phosphorus oxyhalide, such as phosphorus pentachloride or phosphorus oxychloride or phosphorus pentabromide or phosphoryl bromide, or an oxalyl halide such as oxalyl chloride, or using a reagent designed to form an activated complex ester, for example M,M'-dicyclohexylcarbodiimide (DCU or

M-ethyl-M'-(3-dimethylaminopropyl)carbodiimide (EDC) of formula X. In a compound of formula X used as a halogenating agent, X represents, for example, a leaving group such as a halogen such as fluorine, bromine or iodine and primarily chlorine, and M/; means, for example, RSI", OSI, BOVg or SISOSO.

The reaction is optionally carried out in an inert organic solvent, for example in an aliphatic, halogenated aliphatic, aromatic or halogenated aromatic hydrocarbon, such as n-hexane, tribenzene, toluene, xylenes, dichloromethane, 1,2-dichloroethane or chlorobenzene, at a temperature of - 209C to Ge) of the distillation temperature of the reaction mixture, preferably at a temperature from 40 to 1509C, and in the presence of a catalytic amount of M,M-dimethylformamide. In principle, similar reactions are known and described in the literature for different values of the extractable X group. "so z Compounds of formulas I, IM, M and MI are known and can be obtained analogously to the methods described, for example, in

MO 92/07837, OE 3818958, ER 0338992 and OE 3902818. ise)

Compounds of the formula XIiY shown in reaction scheme 2 can be obtained by standard methods, for example, from the corresponding compounds of the formula II « z5 o; so on

X shi s (I), . and

In M and (K) and t b 50 in which K and t have the values specified for formula I! value, and X means a group that can be removed, such as a halogen, 4) for example, by Claisen condensation, or from compounds of the formula II by interaction with a salt of a ketocarboxylic acid of the formula XM -cl

СбО0 M

Gee! and wax, in which KE 36 has the values specified for formula I, and M " means an alkali metal ion | see, for example, UUO 96/261921.

Compounds of formulas II and XI are known and can be obtained analogously to the methods described, for example, in (MO bo 97/46530, in Neyegosusiev, 48, 779 (1998), in Neyegosusiev, 46, 129 (1997) or in Teiganeagop I eChegv , 1749 (19983).

All other compounds of formula I, functionalized according to the definition of group (K) t, can be obtained by various known standard methods, for example, alkylation, halogenation, acylation, amidation, oximation, oxidation and reduction, while the choice of one or another method of preparation is determined by the properties (reaction ability) of substituents in the corresponding intermediate compounds. Examples of similar reactions are given in (MO 97/463531.

All other compounds that fall under the general formula I can be obtained by simple methods taking into account the chemical properties of pyridyl and residues c).

Final products of the formula | can be isolated by conventional methods by concentration or 7/0 evaporation of the solvent and purified by recrystallization or trituration of the solid residue in solvents in which it is practically insoluble, such as ethers, aromatic hydrocarbons or chlorinated hydrocarbons, by distillation or by column chromatography using an acceptable eluent.

In addition, a specialist in this field can easily establish the optimal sequence of some reactions to avoid possible additional reactions.

If the synthesis is not aimed at obtaining and isolating pure isomers directly, the final product may be presented as a mixture of two or more isomers. Such isomers can be separated by methods known per se.

Examples of receipt

Example RI: Preparation of 4-hydroxy-3-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)bicyclo!|3.2.1|oct-3-en-2-one 6b,b8g (0.0305 mol) methyl ether 2 -methyl-b6-trifluoromethylnicotinic acid (obtained by the method described in Negegosusiez, 46, 129 (1997)) is dissolved in 250 ml of methanol/water (in a 3:1 mixture) and 1.92 g (0.04 bmol) of hydrate is added in 222 portions After standing for 4 hours at 22 C, the reaction mixture is added to ethyl acetate and 2N hydrochloric acid, the organic phase is washed three times with water, dried over sodium sulfate and concentrated by evaporation, after which the residue is triturated with a small amount of hexane.

After filtration, 5.69 g (90905 from theory) of the target 2-methyl-b6-trifluoromethylnicotinic acid with a melting point of 147-14996 are obtained,

This obtained 2-methyl-b-trifluoromethylnicotinic acid (2.0 g, 0.0098 mol) is dissolved in 20 Oml of oxalyl chloride. Then add three drops of dimethylformamide and mix for an hour. boil with a reverse (Se) refrigerator. Then the mixture is concentrated on a rotary evaporator and the residue (ie 2-methyl-β6-trifluoromethylnicotinoyl chloride) is dissolved in ZOml of methylene chloride. After that, at 0 °C, 2.7 ml (0.019 bmol) of triethylamine and 0.12 g (0.00098 mol) of dimethylaminopyridine are added, and then 1.49 g (0.0108 mol) of bicycloyl 3.2 are added dropwise. Zoct-2,4-dione dissolved in 20 ml of methylene chloride. After standing for "

According to at 229C, the reaction mixture is extracted with 2n by shaking. hydrochloric acid. The separated methylene chloride phase is washed with water and then extracted by shaking with a 10956 aqueous solution of sodium bicarbonate, dried over sodium sulfate and concentrated by evaporation. As a result, 3.18 g (10095 from theory) of 4-oxo-bicyclo/3.2.1|oct-2-en-2-yl ester of 2-methyl-6-trifluoromethylnicotinic acid are obtained. in the form of oil, which can be used in the next reaction without further purification. 3.02 g (0.009 mol) of 4-oxobicyclo/|3.2.1|oct-2-en-2-yl ether of methyl-b-trifluoromethylnicotinic acid and 1.9 ml (0.013 bmol) of triethylamine are dissolved in 45 bml of acetonitrile. Then, at 22 9C, add 0.01 ml of acetone cyanohydrin. After standing for 18 hours. at 22 "C, the reaction mixture is poured into a mixture of water with 2N. "» with hydrochloric acid and extracted with ethyl acetate by shaking. The ethyl acetate phase is washed with water, and " then with brine, dried over sodium sulfate and concentrated by evaporation, after which the residue is dissolved in a small amount of warm acetone. The target product crystallizes from the reaction mixture during its standing.

After filtration, 0.99 g (3390 from theory) of the required 4-hydroxy-3-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)bicyclo|3.2.1|oct-Z-en-2-one are obtained in the form of white of their crystals (dl 75-7790).

Example P2: (5-cyclopropyl-3-methylsulfanilisoxazol-4-yl)-(2-methyl-6-fluoromethylpyridin-3-yl)umethanone and 14.8 g (0.08 mol) of 3-cyclopropyl tert-butyl ether -Z-oxopropionic acid is dissolved in 25 ml of MeOnH and

Gee! 20 add 1.93 g (0.080 mol) of magnesium. Further, during cooling in an ice bath, 7 ml of carbon tetrachloride is added dropwise, and to complete the reaction, the reaction mixture is stirred at 22 C for an hour. c After concentration by evaporation, the residue is suspended in 100 ml of acetonitrile and at 22 2C, 16.31 g (0.07 mol) of 2-methyl-b-trifluoromethylnicotinoyl chloride (obtained according to example PI) dissolved in 50 ml of acetonitrile is added dropwise. After standing for two hours. the reaction mixture is dissolved in ethyl acetate and washed with saturated sodium bicarbonate solution. The separated ethyl acetate phase is washed with water and dried

HF) over sodium sulfate and concentrated by evaporation. The residue is dissolved in 1 bOml of methylene chloride and at 22260

1 Oml of trifluoroacetic acid is added dropwise. After standing for 18 hours. the reaction mixture is poured into water and extracted with methylene chloride. The methylene chloride phase is washed with water and then with brine, dried over sodium sulfate and concentrated by evaporation. As a result, 17.3 g (8890 from theory) of 1-cyclopropyl-3-(2-methyl-6-trifluoromethylpyridin-3-yl)upropane-1,3-dione are obtained in the form of oil, which can be used in the next reaction without additional purification .

This obtained 1-cyclopropyl-3-(2-methyl-b-trifluoromethylpyridin-3-yl)upropane-1,3-dione (15.0 g, 0.055 mol) is dissolved in 150 ml of dimethylformamide and at 092C, 5 g of potassium fluoride on oxide is added in portions aluminum 65 (alox) as a carrier (0.0055 mol/g, 0.27 bmol). Through the former add 6.7/g (0.088 mol) of carbon disulfide. After standing for 2 hours. 23.6 bg (0.16 bmol) of methyl iodide is added dropwise and the reaction mixture is kept with heating at 2220. After 2 hours. alox is filtered off, the filtrate is poured into water and extracted with ethyl acetate by shaking. The ethyl acetate phase is washed with water and then with brine, dried over sodium sulfate and concentrated by evaporation. The residue is chromatographed on silica gel (eluent: ethyl acetate/hexane in a ratio of 15:1). In this way, 12.0 g (6090 from theory) of 2-(bismethylsulfanylmethylene)-1-cyclopropyl-3-(2-methyl-6-trifluoromethylpyridin-3-yl)/propane-1,3-dione are obtained as a solid. 12.0 g (0.03 mol) of this obtained product together with 5.4 g (0.0 bb mol) of anhydrous sodium acetate are suspended in 120 ml of ethanol. Next, 4.6 g (0.06 bmol) of hydroxylamine hydrochloride are added and the mixture is kept at 222 for 5 h for the reaction to proceed. After that, add another 2.7 g of anhydrous sodium acetate and 2.3 g of hydroxylamine hydrochloride. After standing for 18 hours. the reaction mixture is diluted with water and extracted with ethyl acetate. The ethyl acetate phase is washed with water and then with brine, dried over sodium sulfate and concentrated by evaporation. Trituration with a small amount of ethyl acetate gives 9.0 g (79.5965) of the target product in the form of white crystals ((l 1003-1042).

Example of RZ: (5-cyclopropyl-3-methylsulfinylisoxazol-4-yl)-(2-methyl-b6-trifluoromethylpyridin-3-yl)umethanone 1.50g (0.004Zmol) (5-cyclopropyl-3-methylsulfonylisoxazol-4-yl )-(2-methyl-β6-trifluoromethylpyridin-3Z-ylumethanone is dissolved in

3 ml of acetone/water (in a 2:1 mixture) and at 222C, add 1.02 g (0.0048 mol) of sodium metaperiodate in portions. After standing for 5 hours. the reaction mixture is concentrated by evaporation on a rotary evaporator. The residue is dissolved in water and ethyl acetate. The ethyl acetate phase is dried over sodium sulfate and concentrated by evaporation.

The residue is chromatographed on silica gel (eluent: ethyl acetate/hexane in a ratio of 3:1). In this way, 0.8 g (5195) of the target product was obtained in the form of white crystals (dl 96-972C).

Example Ra: Obtaining

3-hydroxy-4,4-dimethyl-2-(2-methyl-b6-trifluoromethylpyridine-3-carbonyl)cyclohex-2-enone (A2-824) with 6b,b8g (0.0305 mol) methyl ether of 2-methyl- 6-trifluoromethylnicotinic acid (obtained according to the method described in Neijegosusieev, 46, 129 (1997)) is dissolved in 250 ml of methanol/water (in a 3:1 mixture) and at a temperature of 2226 portions, 1.92 g (0.04 bmol) of hydroxide hydrate is added lithium. After standing for 4 hours at 22 PS, the reaction mixture is added to ethyl acetate and 2N hydrochloric acid, the organic phase is washed three times with water, dried over sodium sulfate and concentrated by evaporation, after which the residue is triturated with a small amount of K, hexane. After filtration, 5 .69g (9095 from theory) target 2-methyl-6-trifluoromethylnicotinic acid Ge) with a melting point of 1147-1496.

This obtained 2-methyl-b-trifluoromethylnicotinic acid (1.02 bg, 0.00 bmol) is dissolved in 20 ml of oxalyl chloride. Then add three drops of dimethylformamide and mix for an hour. boil with reverse "And refrigerator. Then the mixture is concentrated by evaporation on a rotary evaporator and the residue (i.e. 3o 2-methyl-b6-trifluoromethylnicotinoyl chloride) is dissolved in 100 ml of methylene chloride. After that, at a temperature of 02Сb, 1.bml (0.0115mol) of triethylamine and 0.7g (0.005mol) of 4,4-dimethylcyclohexane-1,3-dione are added. After standing for 2 hours. at a temperature of 2223, the solvent is removed on a vacuum rotary evaporator, the resulting residue is dissolved in 55 ml of acetonitrile, and to rearrange the intermediate product, 0.15 ml « 20 (0.001 bmol) of acetone cyanohydrin and 0.79 ml (0.0057 mol) of triethylamine are added. After stirring for four hours at room temperature, the reaction solution is concentrated by evaporation. The resulting syrup is chromatographed on silica gel. Light yellow viscous oil obtained as a result of elution with a mixture of toluene, ethyl alcohol, dioxane, triethylamine and water (in the ratio of 100:40:20:20:5 parts by volume) (K-0.39 at using the indicated mixture as a mobile phase), dissolve in dichloromethane and successively wash with 75 ml of 5% hydrochloric acid and 7/bml of water. After drying the organic solution over Ma 2550, and concentrating -1 by evaporation, 1.05 g (6390) of the pure compound specified in the title is obtained. 7TH-NMR (d5-DMSO, 5 ppm): 1.342, 8, 6H; 2.088, i, 9-9HZ, 2H; 2,685, 8, ZN; 2.982, i, 9U-9HCts, 2H; t- 8.030, a, U-8.1Hz, 1H; 8.094, a, U-81Hz, 1N. «сl Example RB5: Preparation of 5-methyl-5-trifluoromethylcyclohexane-1,3-dione (example B1066)

0.64 g of sodium is placed in 40 ml of ethanol, after which 3.23 ml of acetic acid methyl ether and 4.9 g

Me. isopropyl ether of 4,4,4-trifluoro-3-methylbut-2-enoic acid and the mixture is kept at boiling temperature

F within 18 hours. After extraction with dilute hydrochloric acid in countercurrent ethyl acetate, the mixture is concentrated by evaporation. The resulting residue in the form of crude methyl ether of 2-methyl-4,6-dioxo-2-fluoromethylcyclohexanecarboxylic acid is esterified at boiling temperature in the presence of 9.1 g of sodium hydroxide in a mixture of methanol and water. After that, the mixture is acidified with hydrochloric acid and extracted with fresh ethyl acetate. After recrystallization (from ethyl acetate), pure (F, 5-methyl-5-trifluoromethylcyclohexane-1,3-dione with a melting point of 150-15290) is obtained. Example Pb: Preparation of methyl ether 2-hydroxy-1-methoxy-5-methyl- 4-oxocyclohex-2-encarboxylic acid (B 1069) in Prepare a Z095 solution of Z35.8g of sodium methanolate in bbml of dimethylsulfoxide and treat for 20 minutes at a temperature of 30-359C with a mixture of 16.7g of Z-methyl-Z-butene-2- of it and 32.4 g of the dimethyl ether of methoxymalonic acid. Then the mixture is stirred for an hour at a temperature of 35923, acidified with hydrochloric acid and then extracted several times with dichloromethane. The organic phases are washed with water, dried and concentrated. By crystallization from hot ethyl acetate and hexane, pure methyl ether is obtained 65 2-hydroxy-1-methoxy-5-methyl-4-oxocyclohex-2-encarboxylic acid with a melting point of 117-117.596.

Example P7: Preparation of methyl ether

2-hydroxy-1-methoxy-5-methyl-3-(2-methyl-b-trifluoromethylpyridine-3-carbonyl)-4-oxocyclohex-2-encarboxylic acid (A2-81069) 2.23g of fresh 2-methyl-b6 --rifluoromethylnicotinoyl chloride is added to a mixture of 2.14 g of 2-hydroxy-1-methoxy-5-methyl-4-oxocyclohex-2-encarboxylic acid methyl ether and 2.02 g of triethylamine in ZOml of acetonitrile.

Approximately through ЗОхв. add 0.06b5g of potassium cyanide and stir the mixture for 18 hours. Then the mixture is extracted at pH 2 with water in a countercurrent with ethyl acetate, dried over magnesium sulfate and concentrated by evaporation. As a result of filtration through silica gel (mobile phase: ethyl acetate/methanol/triethylamine in the ratio 85:10:5) pure methyl ether 70 2-hydroxy-1-methoxy-5-methyl-3-(2-methyl-b-trifluoromethylpyridine- 3-carbonyl)-4-oxocyclohex-2-encarboxylic acid in the form of a viscous oil.

Example of RV: Obtaining

3-hydroxy-4-methoxy-6-methyl-2-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)cyclohex-2-enone (A2-81070) 0.586 g of potassium hydroxide is added to 1.4 g of methyl ether 2- of hydroxy-1-methoxy-5-methyl-3-(2-methyl-b-trifluoromethylpyridine-3-carbonyl)-4-oxocyclohex-2-enecarboxylic acid in dioxane/water (5:3) and the mixture is stirred for Then the mixture is acidified (pH 3) and extracted with fresh ethyl acetate. The crude product is purified by chromatography similarly to example P7. In this way //3-hydroxy-4-methoxy-6-methyl-2-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)ycyclohex-2-enone is obtained in the form of a viscous oil (in the form of a mixture of C tautomeric forms according to H-NMR data).

By the method described above, it is also possible to obtain the compounds presented in the following tables using for this purpose the methods described in the explanations to the general reaction schemes 1 and 2 and in the literature sources mentioned in this description. In the tables below, Ri represents a phenyl group and SS represents an ethyne group. with o (Se) "co

IS) « and - - p. and? -I sh» 1 b 50 42)

F) name) 60 b5

Table 1

Compounds of formulas I

Table I: Compounds of formula IB: ю Kv OO o

Kk 7 - -

Kk In 76 o

Kk | Compound | -( Yazh | Bzhsh | B | Bzh- | more

T001 757 002 сНасн svo 1003 снасН 111-112 1004 снисН св | nn Her sch zv to05 1006 sv Her sv | noi noi o) 1007 sshOosn 124-126 t pov сН5Ме 1 pa СНоВОоМе 55-65 as

TO 8s 111 St | noi noi

T011 BOSN svo | nn Ge) 012 Osn sv | noi! but

T013 5 11111 St | noi noi and

T014 BOR svo | nn « to15 OR sv | noi! but

Tov SEZSE to sew -

Т017 сНнсН СЕзСЕ shih shi shih I to18 сНниІССН СЕЖСЕ sht sew 1019 сн(сн СЕгзСЕ vyti shi shih " t020 СЕЗСЭ shih shih shih ШИ 1021 SEZSE non o, s 1022 snOosN SEZSE vy it i . 1023 СсNoeMe SEzSE shih shih shih 1 SHY02 4," SNoOoMe SEZSE sew it 1025 SEZSE sew sew: I 15 T026 Osn SEZSE tires: SHY PO -1 1027 "osn SEZSE sht sew t028 SEZSE vy sew -e to2a BOR SEzSE shih shih shih I sl 1030 5OzvN SEZSE nn Her ngrya T031 sni 1 bed room

F t032 snasN sn noi no

Ф 1033 сНхШсН sne HER noi note 1034 stsn sne | noi noi

T035 shimi: write PI st TI PI KhVO PO NOYA PO

F) t 60 65

1036 St sleep n | n | (Kv 21037 | сшосв 1/0 сн 1 NOI noi SS loz | ssheme | sn; | n noi 7777777

I. 1039 | snvoome | sleep n | n'Y ( tyu 1041 zOosn SNE N NN 1042 | vOosvy | sn | n. 1 nn / Her vine | 7 5R 177 sv | noi noi 77 1044 | vo | sne | nn noi 77777777 eto 1771 voti 111111 sn | noi noi. 1046 | St. | sat | sf noi! 777777 1052 | sostv | se | ssh no lov | ssheme | se | sn | nn | B 1054 | sbOome | Sat | sn noi 7777 20. | l1o5B. 1 8sv | s | sf noi lob | os 1/7 se st | nose 1057. | sun | se |snsh n/ HER ( 10586 171111 5 HER st | st noi 7. lov | BOR 17771 s | se | nosu sch | LOB 11171111 5ORN 0 | С | svi NOI | o 1061/1777 sni | sesb | sv no | 7777771 10862 | snasn. | ses. | sv no | 7777 lov | (snyasno | sesg, | sn.) n | (B 1064 | snisnsh | seS | Sv no Y 7777 | Te) zo Z 10656. | (Р 1 svСЬ | sv| nn D ( s lovv | sv | ses. | sne! no | Bo | і-o 1057 | sshosni | ses | sn no ІІ | oyu 1068 | syubeme | ses" | sleep no Y S.) o lovya | dream;me, 0/0 seSE, | se | NN | (B | - zv MBA - 020 («| all with, |svv| n | m 1071 | axes | session St n i ( 111072, | 8bbsn. 1/0 ses, | s | nn i SS 22010731 50 | ses. | svv noi 1074 | voRy | sesg» | st3 no | 7777771 | « 2010756. | vo seSE. | sne, NSS - lov | st 1771 сн | сшв| no s 1077. sne | sne! noi 7777777 45. | lovi | svv 177 sne | sv | nos

Mo Gooolova 0 | sosnv | sn |sv| n | ( them 1083 | ssheme | sleep | sleep no Her 1084 | syubome | sleep | sten

Fi lovb | 8s 17711 sn se | noi vh 0 1 3З51086... | AXIS 1/0 sn) with | But 1087. | v80os3y | svo |svtv no

FO 017771 lo88 1111 51111111 sn sne noi su lov8 1777 BORY | dream | sleep noa! 777777

Ot pi ZON i pis NE i shchi Na piy nin nnya 52 iF) ime) 60 b5 tp 92-94 t092 snesN svv | n | St | 7. t093 снзЬсНн св | noi st 1 to094 stisn sv noi! St. 1095 in 11 st. 1096 USA | its | but | 777 1097 снОосН св | noi st 1098 steme sv HER no І st 1099 SNIVOzMe st | but st that background 5s 1 1 s | Noi St. Her

PET Osn St | but | Article 1102 "Foundation of St New St | 77777. 1103 BR 111sg3 | NOI St. Her 0.

Tl104 ORE stv Her noi s 17105 5O2RN ev ne sch o o; z0 "o

IS

«t i - « o, s z -I ih s b 50

F

(F; at 60 65

Table 2

Compounds of formula IB

Table 2: Compounds of the formula Is: 70 K v o o s n k Z 77 h-- y

SN r. o Z (Is) district

Kk M o M

KE in 2 SNz 2.00 107-109 2.002 sne oil 2.003 sne oil cm 2.004 snisN o 2.006 SNOVI SE N H 2.007 spOosn 2.p08 sNIMe Ge) zo 2.009 SNIVO»Me so 2.010 2t asn yu 2.012 OH 2.015 Z NORA 5 SE 2.015 2.016 SEZE 2.017 SS SS SS SE SE SE SE SE SE SEZE 2.018 STOCKSE "Yu 2.019 SNUSN SUNSN SESCE SOSCE SOSCE EU 2.030 5ORA SEzSE 2.03. i) 2.032 снсН 2.033 снИсН 2.034 снсн

F) t bo 65

2 oz s nn V S NE: nn nn 77777171717171710101010102938 011 s nn 215M. .Ю.ЮЮ323232323424040.01й7.....31313111с nn 1.....юЮ0303203732330Й1.... н...... 1 юЮюжщЖД Дн Б И 2 о 41 BO сн СН eЕ- нн n

Г-А- 3 62 - 2 « « I L.A A -- 5 255 5 5 - ( -23ИМ- 25 ЙМВИД2Ш2ЗК-5Б5МШБШБ4Ш0 Ш02Ш2ЗК--5-- 9 2 o 46 сн гом ха сн нн 2 o 51 с нн :V SE sn nn with 1iIR----2 532:3- -- - А 5 5 5 6 2 ЗB 52 2БВБ2Б-- 2 20З1-2 2 2 55 (Р Я LZ OA 2 o B 5 R p gom she onshchi ne SN n ta 07 to ok to E NE E i o Nisha 2 o 76 sn S HER sn nn 2 o v1 s nn V S NE: sn nn 2 ovi s N.O :M ee S NE: sn nn 20. |Г--555А- 5 232 1 " « l5 З5 т Ж- 5 Х""З (5 Р 2 жШШЖ; 2 5 "lzhh ( А "ШЖ (А 2 o vo 5 o rn Toh x NI ZY sen n s what about (Se) (Se)

IF) - otv Bor « yu 2.091 z s 2.092 sn 2.093 syЬsn

Iz» 2.094 snasn p 2.095 1 2.096 Sniv 2.097 stosn - oto oNoemee i» 2.099 SNIBO»Me 2100 i-y 2101 Mon

Фо 2102 5О; СН 2103 (42) 2104 ОРИ 2105 что кобо b5 -d1-

Table C

Compounds of formula si

Table 3: Formula Ia:

Kk te o; he

In SN

7th century p (4)

E M

There are 76!

K zv sleep sleep

WITH

3001 stv with HER noi no 3.002 snsno svv HER noi no! 3.003 сНнаН св | non s 3004 snaIsNn st |! non o 3006 SNOVI SE N N 3.007 stOosN st Hn zpo8 sNnooMe sv | non Ge) from 3.009 SNoVO»Me sv | noi no so 3010 all s Her noi noi 301 asn sv | non yu 3012 Osn sv | non 3.013 вн 1111s HER noi noi Z 3015 5ORA SE NN 3016 SEZSE thread ME I 3017 ss SEZSE nn 3.018 snUsN SEZSE thread sew « lyu 3019 snysn SEZSE proud shih shih Z7Z s 3020 SEZSE 3021 SEZSO osnSE sew with st202» шиши: ши п 3023 СсНеМе SEZSE non 3.024 СНО» Me SEZSE shih shiti - 45 3.025 SEZSE shih shih 3026 "osn SEZSE sht shi shshshsh y" 3.027 Osn SEzSE shih shiti PI 3.028 SEZSE nih shi shih o 3029 "OR SEZSE nn c) 3.030 ORE ses. | n Her well 3031 stv 1 sn | noi no! (42).

F) t 60 65

8035 177777 RN | dream noi noi 77 8036 | sun 1711 sun 1 NOI noi su 803 1771 soni | dream | n | n/ | (KB

I. 3038 | snbeme | Sat | n | n Her ( cart | sveOmMe | sn | N | n | (KB

Zm 177777 5СН. | sleep n | n/ Her

Vb 17777 8-axis | dream n | noi 38042 | 80Os | sleep nH | n | (.Й 8043/1715 | sne | noi noi 77777) eGv8oya 1,771 vot 1711 sn | noi noi Su zob | vOR 1777 Sn 1 Nov| noi 77 8046 177777 st | se | US | noi 3047 | sshsv | its | US | n | (passed | (Sun 1 Sep | Sat | Nov 777 5 | Sat 17 Sat | Sat | Sun 1 Nov 77777.

Vb 1777771 RN | se | St | n/Y 80610771 sm 111 s 1 sv | noy SS 80 | pine trees | Sat | US | nn. | (KB vVb53 177 snaMme | se | ssh | n/ | BC 20.| vol. 1 ssh5omMe | se | ssh | NN Her (B

Z055 17777 5SI | se | Article | but HER

Vb 1777 8osvI | with | US | but HER 38057 | 80oOs6 | Sat | US | nn | (K(B 8058/1775 | s | st! noi 7777.) sch | Vb 17771 85oORI | s | st 1 noi | o zov | vOR 1777 s 1 s | n/oY 77 801 177771111svv | ses | ssh | nn. | (B 38062 | sshsvn | seSE | S | NNN | ( zov3 | (snrseno 01 ses | sv | nn | Б | se zo | 3838054 | sSnissh 1 seS | sv | nN HER ( 8/7 RN | sesS6 | ssh | N |

Zb 7777 snaMme | ses | US | n | Щ4(ЛК | h зв M З0БЯ 00 | 0 SNiBOIMe 0000 SES. | Svv. | N | (M | M

Vb at 177777 5СН. | seS | Article | n | (KB shk SHE ZHNE ZHII YAN NN 3.072 zOSN SEZSE sn H 80317718 | sesS. | s | n | ShshchB | « and ab7ya4 17111 85ORI | sesS | ssh | no Her | Z r oovFb5 17111 8BORI | ss | sv | ng ( ( s 8076 1771111svv | sn | ssh | noi "from 38077 | sshsv | sb | sv | n | (

And sb | slept 17 days; | US | but 777 8079 17 demolish | sleep with Her no Her i | call Ri 177 sn | St | n | (

MO goooooz | 777 sia | sleep st but them" 38082 | pine trees | Sat | St | n | ( zov3 | Same 0 сн | с | no i-y 80ВЯ 171 с5ООМе | сн | St. Her no Her vu 201 vla 1777711 5сSNU 17711 sne) | US | N | (B vo | 8osnU. 1110 sn | sv | noi S

Fo vVbvya 1 5OSt | dream | US | n | (KBb

Z OVO t nt ZRA T a ty pis NE t ts Hiring 52 iF) name) 60 b5

3089 ОР sne Her sv Her n Her 3.090 shOoRA sne | St | n.s 3091 svv | St | But | with |. 3092 sten se | N | sv 3.093 sna svv no st 1 3.094 sNSsN sv HER no! Article 3.095 RN of HER saint | N | Article 3.095 of St today st 17. 3.097 сносон св | ns 70 3098 sneMe sv no st 11111111 3.099 SNIBOMe sv no st 111111 3100 I 5СН3 | with | But | own! 3101 Osn with | N | St. 3102 Basic St. St. 1 3103 R 1 1st/ 1st st.

IS

"I і- " - s :z" -I і" s b 50

F

(F;

Go) 60 65 -AA-

Table 4

Compounds of the formula in

Table 4: Compounds of formula Ie: 70 CH and

Kk 78 o

K t Shk i: M Y i i (e) pcs, o 2o A same i in 75

Spol chUka Mo Eh Ezv No» Ege i Yilp s 4 001 103-704 sch 25 4002 sNnasNn svo 1 noi noi 5 17777777 | o 4 004 sniaasn SE N N in 4 005 in SG st 1 noi noi 17777111 4 006 sv | svo Her noi noi 58 17777777 | Ge) from 4,007 stOosn sv | nn Her n/Y 5 | so 4 POV SNoYAMe svo 1 noi noi 5 17777777 4 poa svebOome | se | nn Her n/ Her 8 | Yu 4010 8Sun 11 St | noi noi 5177 «

REK Osn se | noi noi 51777771 35 4012 Osn se | n Her n/ Her im- 4013 R 11 St | noi noi 5 17. 4014 BOR se | noi noi 51777771 4015 ОР se ІИ no Her no Her 5 | « 4016 ss | nn | nn | 585 4017 snsn sges | NN HER nn | 5 2 s 4 018 sNAasN sesSe | nN Her nn Her 8 Her and 4019 snasn ss | n | n | 85 BC "U("

From" 4020 sesEe | NN HER nn | 5 4021 svesEb | NN | nn Her 85 15 4022 stTtOosn ss | No. 85177777 - 4023 SNIZMe ss | nn yin; 8 шгщДщДюЦ( 4024 sno" Me sese | nN Her noi 5 sl 4026 "Osn SESE N N in 4027 5OSN ss. | NN ІІ nn ІІ 5

F 4028 ss | No. 85177777

F 4 029 BOR SES. | NN HER nn | 5 4 030 that sesee | nN Her n/ Her 5 HER 4032 sn SNE N N p3

F) t bo 65

4033 | (snvShisn | sv | n | n | 5 2 КГК 4034 | snisnls | sne | n | n | 5 4036 | Р | сн noi noi 5177 | 4036 | sv | sne | n | n | 5 4.37 SsnOsnz SNE; N N no lead | seme | so 80 no) 517 4033 | cSspebme | sNE | nH | N | 5 |! 4040 | 85sv 1 sn 1 no no 51 yu | manifest | East | dream | n n | 5 4042 | in a dream | dreams | nn | nn 5 4043 | R | dreams | noi no Her 5 1777 4044 | WORNY | sleep n | n | 5 4045 | BOR | mon 1 noi noi 51711111 tv 06 | St St St n 1 5 Sh 4047 | sshsny | se | St | n | 85 408 | (snesn | s | hundred noi 5 1 7 щДЩщ RKr(Ke«s apa | snestn | se | se | n | 5 |! 4050 | Ri | sv | sv | n | 85 |! dobi | sv; | s | s o | noi 5 1 7 777 217 4055 | stosnya. | svo | st | n | 5 405638 | ssheme | sv | so | n | 5 | ( a0564 | stebome | se | s | no | 8 1 777 4055 | BOS | St | stvyn /ОЙ 5 1 forehead | 8osv | sv | so | no | 5 | (| cm 2 | 8057 | vosv o s | Syo| n 1 5! | o 4056 | R | se ssh o noi 85 1 g shDsh dova | BOR | se | sne | n | 5 |! 4060 | BOR | se | sv | n | 85 |! g yaovi | sni | ss | s o | no Y 5 1 shDHshsh shGK( | i-o zo | 40b2 | snsn. 5 85 ДЩДЩщ M K(: | stebme | ses, | sv | n | 5 | ( 4070 | es. | ss, | St. | n | 5! | « 40 | 85ost | ss | st | no | 5 . D 7 zo | 4072 | v8osn. | ss. | St | n | 5 | | Z s 4053 | R | sesE, | St. | n | 5 |! 4074 | 8BoOR | ss | hundred | but Y 5 . D 4055 | 80 | ss | Sn | N | 5 |! 4076 | St. Sn | so o| but | 5 | Щ ( 45.1...2..4077 | снсн. | сн | sto | no | 85 1 7 - 4078 | сншШсн | сне 1 st 1 noi 85 17 4079 | снесв | сн | сё | н | 5 | ( д | RI | sne | Sto | n Her 5 |! 2 sh:( in 408 | sv | sne | st | no Y 85 . DschDsch zo | 4082 | snyuosn | sne | s | n | 5

F 4083 | Seme | sNE | Saint, | nH | 5

F 40864 | sshvOome | snv | Article | but | 5. Sh KK GKZhK 4086 | v8sy | sleep St | n | 5,086 | 5OoSt | sn st o noi 5 17 vv stitch 0 5OsNi sne sn Nv (F, ko 60 bo lov | BR | sne | st | n | 5 Y m 4083 | v8voRY | sn | sv | n | 85 ovo | BORNI | sn | sto | no Y 5 DSHD FR BR 8 | 40ei | snu | sv | n | ssh | 5 4.92 SsNIN» SEz N SNz not lova | se | sat 1 nos) 51 4094 | tackle | St | n | Article | 5 | 4 ZeF( 4096 | R 17 Sv 1 no| Sun | 5 | щЩщДщ( ( yu | java | ssh | s | n st | 5 | Ж Ж 'Z 4097 | sosni | svo | nn | sv 5 lev | sshbme | se | no sne | 5 DK Zh 4099 | sshvome | sv | n | se | 85 loyu | 5sni | s 1 no s Her 511 tv 1 7 vost | svv | n | st | 5 4lo. | vBosyu6 | se | n | s | 8 loz | VL HER se 1 no sv | 5 177771 4104 | voORN | svo | no | st | 5 | (B ali | BORY | se | n | s | 85 1 am | ss | svo | no | n | 501 SS 4lov | (snvsno 1 svo 1 no| no voi yala | snhsyu | se no no|Ї vo 17777771 alo R І sv 1 noi noi Bo 11111111 s 4lm | 7 svo 17 svo 1 no | new| vo | 77 cm 2 | 82 | sshosnza se | no n 150 her o 43 | ssheme | se | nn /o| 80177771 414 | sshebme | sv | n | n | 50 | 2 Sh 4 | o vst | sv | n | n | vo | ( left | v8ost | s | noi no 50177771 i-o za | 4 | vosti | svv | n | n | vo І || о 4liv | 8R 171 sv 1 no no! voi ali | vo | s 1 no no|І 50177771 yuyu 4120 | in | sv | no | noi 5017 | « 4l | sv 41 ss. | no | no| voi 77 z5 | ali | snsn. | ss | nN | n | vo І | t- 4423 | snshsn | ss | no but 501777 4l24 | v | sys. | but | n | in | KD(Щ ( 435 | R | seSB | nn | n 150171 | « lov | sv | ss | noi no | Bo 17777771 zo | 4127 | snyuosn. | ses. | вn | н | vo Her bU0 | З с 4428 | Sneme ss ...2..4139 | sun. , | no | n 1 501 71 at 4436 | sv | sne | noi no|

F 4138 | (snesn | sun | nn | n | 50 | 2 years BC

F al3ya | snusnt | dreams | noi no | Because 17777771 4 liyu | 7 RN | sleep n | but | in |! 77 ali stv | sb 1 noi noi Bo 11111111 vv yo Her stos sn NN vo (F, ko 60 bo

4m3z | sscheme | sleep n | n | 50 | (RKbV al | snvome | snE, | n | n | go | MKM MKJ( 4m5 | vs | sn | n | n | 850 | (b | am | v8ost | sn | n | n | 80 ІИ ( rat 4148 ZRy SNE Нн Н вО 4 ма | воРы | сн | н | н | 850 | ШщщШшщуК(б s 4лвю | 85ОРИ | sne | н | н | 80 | Б 41 | sne | s | Se. | н | 850 | 77 е|7yalva 1 st. se | ssh | n | 50 |! ( 4156 | ssh | se | sna | n | 850 | (fvb 51 4lv, | snyuosne | se | ssh | n | go | Su 458 | svebme | se | Se | n | 850 | (vro 4l5a | snyaome | se | sleep

Yalta | sun | St dream | n | 850 | шЩщЬ(m/ 20.| vo | 8bisn. | svv | sv | n 50 S. yalv3 | R | sv | ssh | no | о | (BK 4 lvya | voRy | se | Snai | n | 850 | Щщ (лК o 4lvv | BORY | se | Se | n | 50 HER BM yav | sn. | ss; | ssh | no | vo, | (F | sch 25. | alu | snasn; | sSesg, | Sn. | n | 50 Her (BM | o 488 | (snlsno | seasg. | svya | n | 50 | RZ(fBK alla | snysnya. | svasg. | sna. | n | 850 | (sKbve 4lyayu | R | sess. | sa | n | 80, | n | vo | (KG UZ ch zv M | 8vbsb. | SES. | sv | NN | 50177771 cha 48 | BR | sesE. | ssh | NN | 50 |! ( s yalya | voRy | sesg, | ssh | n | in | X(x 4 | BORY | sSesg, | Snze | n | 50 ІІІ B МЖ s 4lvi | sni | sne | snzhe.i | n | 850 | R (Kfbhb | « java | sshsn, | sНnE | ssh | no in on. | n | 850 | (urbve khz 418 | R | sne | sne | n | 50 | Su " al | sshvb | sn | ssh | no | o | (MG 47 | svyuosna. | snE | sne. | n | 850 | Sh (KbVYub 45! av | ssheme | sn | ssh | n | 50 Y (BBY.oKMK(

MO Gooyamlva | snvOme | Sun, Sun | n 850 | Щ (КБ их с 4ляю | вс | сн, | Сн | н | 850 HER щЩщБ M al | ost | снE | сш | n | во | Р(КвКБ: Ж (

F001711yaleg | v5FsNI | snE, | US | but | in | (: ( entry 2 15493. | 8Ry | sn | ssh | nNo| o Her 7777771 484 | voRy | sNE | ssh | n | 850 | sh(Kfv

Fo yaleb | 8bti | sleep, | US | but | about HER al | 7 sleep | Article | vn | sleep | in | (ХЖ а тс На СН пит на пт п s Н ЗО на ня 52 иФ) име) 60 b5

4 | (снсн | se | n | сш | 50 | РКхвеС алея | свысвю | se | n | с | во | :К ( 480 | R | se | n | сш | во | б(

And 421 | St se | n | sleep in | ЛБК et 4203 SNIioMe Se Нн сн воО 454 | dream | St | n | sy | 50 | (сКбхб 425 | sun | st | n | sun | 80 | (KB KZ 425 | 5ost | sv | n | ssh | 50 | (NKREV e|7ya27 1 sun. | svv | n | st | go | (B M S« av | BR | sv | n | ssh | 50 | (Ko me | v8oRy | se | n | ssh | vo | X(K 4mo0 | BOR | s | n | St | 50 |! ( 51 4m2 | sshsn. 85 427 sv | n | n | 55 | w 480 | 85 | sv | n | n | 55 D K 421 | vost | s | n | n | 85 | GB | sch | 4222 | 8bsnv | svo | n | n 155 (MK ((B| o 4893 | BR | sv | n | n | 855 | KyUK 424 | voRy | sv | n | n | 855 425 | Ot | se | n | n | 55 | KB op Ko 425 | sn | Ses. | n | n | 55 | | Te) zo / 4227 | snasn; | sevs | n | n | 855 4228 | (snsn | sesE. | n | n | 5 | (KBF. | i-o 459 | Snysne | Ssesg .| SS | nH | n | 855 sh B (Ж | m 4233 | ssheme | sesSE. | NN | n | 55 4234 | snvome | sesg, | n | n | 8. | b(Kh 4835 | Sv | sSses. | nH | n | 55 | shD К(КС(КВи 48356 | в8осн. | сес) | н | н | 55 | КИ Кжз| « 4237 | 805сН. | sesg. | н | но | 85 | Б | - 488 | РИ 1 сес; | н | н | 855 s 4239 | voRy | ses. | n | n | 855 khz 40 | 5ORI | sesg | nN | n | 55 | K(Bvbi " pits | ssh | sn | n | no | 5 | KB 42 | pines | sn | n | n | 55 | sh KY | 4mza | (sshsn | sn | n | n (855 DK

MOG pit | snaisei | sn 1 no no 855| 485 of them R | Sat | n | n | 55 sh shD M(KvB 4mB | ssh | sn | n | n | 55 | KyuyK(Yab

Fo yamt | snvyuosnu | sleep n | but | 85 | BM ( entrance 22 1 am | us

Pho 14250 | 8sSv | sleep n | but | 85| Щ КК(БВФЙ 481 | восн | сн | н | н | 85 | РКиеБ 252 nt ОС ни С NE py pi пн я Зо ня 52 иФ) име) 60 b5

4 Fe same her

And with her|Ff her 4" BI B N FI yuYU 2 tv her gi I B her 2 yav B NOYUU s with o (Se) te yuyu " - - s . i" -I c" 1

FU at 42) ko 60 65

Table 5

Compounds of the formula KhM

Table 5: Compounds of formula ХУ:

Kk in o;

Kk vi

M: ON (HU) b

Kk 82 M k 7 snasN snavsN

AV 117717 sleeps 7 | no. 177777 no./17717171 st sch o snasN

And | snosN sleep e) zo i

I eat FISH

RyBO h sno ich- ss " I snesN with s snaASNSN snaivOmsN ;" snaM5O 15 siSN - stBsN sneOOoSsN - sNaBO:sN sl

F

F SEZSE

SEZSE snasN SEZSE

SEzSE (F) ko) 60 65 i dz Re N N sgzseE o y 2 sch 25 o

F

» yu yu to her with 5 - " o - - and g" - with sl yu

F

F zv iF) ime) 60 bo

AV? SN N N SES u

ALOZ RO N N SES

18 sch (5) o

A122 12 4|triazol-1-ylmethyl НН СЕ»СИ 7) « и-

A128 сНлЬсСН Н Н СНЕ « sho s . -» - t s b

Frya (F. ko bo b5

ID pisnnvyky and 7170 c o (Co) z0 "co

IS

"I - « - s:z" -I s" 1 b 50 4)

F. ko 60 65

A sNnUVsn N sn SE yu

АРИ иклопропил Н сн SBS 18 сх о о

Ag SNazvO, MSN H sn SEZSE 7) « i-

AgAV SNzeOesn N SN SES « sho p. -» - te s b

Frya (F. ko bo b5

HELL

And 7170 t ZE

AN with o (Co) z0 "co

IS

"I - " - s :z" -I s" 1 b 50 4) (F ko 60 65

Azy SnyasNn N Ri SE yu

AZAZ SNiZSN N Rp SE 18 that cm z o i-o da SE N ry SEZSE yuyu ch ze i-

AAPV SNO Tsen N Ri SE « yav s a - 5; oh

F

F dv iF) ime) 60 b5

HELL

A N and 7170 t of beer

ANA

Ge o

AC

- what

BA Eya "co

IS

"I - " - - ee g" lush leftovers -I s" (9) b 50 4)

F. ko 60 65

AB? N dreams H SN o

AVEZ N snUvsN N SNE and 2 sc 2 p

F

Ar N sn N SO yu her zv - rea N SNarvim N SS " o z ne i i" z - z s yu

F

F zv

F) name) 60 because you are writing, you are writing nowadays 7170 5

AND

Ge o (Se) z0 "co

IS

« m- « - s :z" -I s" (9) b 50 4) (F; ko 60 65

AN24 N SNU» sn SNE yu

AAZO N yclopropyl sn SS 18 sch (5) o

ANAZ N SNIvOMISN sn ss t) « i-

AVZO N sn Ri SE « sho s. -» - t s b

Frya (F. ko bo b5

AVVO N snzaasNn Ri SE yu

AvaB N sna Rp SEzSg 18 that cm with o

Fo

AZOB N SNZM o Ri SE yuyu « ze yi-

A N iclopropyl Ri SgZSESE « 2 s. a - 5; oh

F

F zv iF) ime) 60 b5

AaZB N sn Re SES yu 942 N snOosn Re SES 18 sch (5) o dob N snazasn Re SES 7) « i-

AB N yclopropyl Ri SNE « sho p. -» - e s b

Frya (F. ko bo b5

Aza N SNIV Ri s yu

Ua N Ri Rp SS 18 that cm with o o

AT E N N SE yu ch ze yi-

А1023 сниюНнз НН СЕ « no, s a - 5; oh

F

F vv A ASHMT 17777111 s 111111 ІИ 77on 11111 NS 11sv iF) ime) 60 b5

1043 N SE

A1044 N CE

A1045 N SE and A1046 N SE 1047 N SE

ATO48 N SE dtocha N SE

ATOBO N SE

A1052 n ovo-sn n SE

A1053 Oo8O-sE N SE

ATO5A sisNne N SE 1055 N SE iv ATOBB N SE

A1057 SN. N SE

ATOBV SE.SNA N SE

TOB N SE

ATOBO sSne»sne N SE

ATOVI siSNeSN H SE 20 ATOV2 si-s-SN N SE

A1OB6Z SEZSNESN N SE diovB n sno n SE

ATOBB N SE s 25 A1OV7 Osn N SE o

ATObV 802se N SE dlova N SE d1071 sn N E SE so zo A1072 si SE so

ATO73 Vi SE d1О74 cm SE yu d1075 SNU N sn SEz « d1o076 sne n snu SEZ 35 A1077 sn v sno SE і-

ATOTV. SE

In the following table, 6 O represents the group Oz "40 Ko o) s Ka ;" and in (05),

In i. o sh i s Ka Zv

Me, while Cz represents the following radicals B: 4)

F) about 65

Table b

Radicals B in | 77777lsnyai/ | noi noi no he hundred in HER sshsni | n | n HER n | onY («sto v | snsnsn | n | n | n on | ost v' | snsn | n | n | n | on -( os6-6474 v | иисшшшс | n | n Her n HERI on sto 86 | /sshe | n | n | n on | o sto t5 sch 5) d) zo i-o yu h z5 M « y z s

Of 18 - their sl

FO in (F) ko bo b5

V5y sno H sn H OH sn t

VEZ Ro N SN N ON sn sch o

That) :

Вв2 СЕ СН СН Н ОН sno yuch svcha

Va RyZOa СНа СНа Н On СНе « - to с хз» " их их 5, b)

Fo iF) ime) 60 b5

112 SNniIsSn» SNzenN; N N On SN

B119 Re SNnIsn Н N ОН СН " 2 cm 2 o ino

В1з38 СНззс Н Н Н ОН snen yu " zv t 144 СсНнисОо Н Н Н ОН snen " no s. g" - p. go

F

F dv iF) ime) 60 b5

ВИБз несен сн Н N ОН снет вВ175 riza сн Н Н ОН сне сх o

Te) : vB154 S NaaM N SN N ON snen ke, oyu - zv k

В1Зз СМ Н СНа Н On Сснен» «

There are 5 of them, b)

Fo iF) ime) 60 b5

В225 СсНнЗБсНн сн сн сн ОН снен t

B231 СНО сн СН сн ОН снен сч о

That) :

В250 СНО снЗсНн Н N ОН snen ke, oyu - zv k

B255 snASNeN» SnasSne» N N On Ssnen; "

There are 5 of them, b)

Fo iF) ime) 60 b5

B281 SNaza mo N N N ON SeO t

B287 СМ Н Н Н ОН СеО шко о

That) :

VZoB Riz SN N N ON S8O ke, oyu - k

AND

В312 сс Н СН Н ОН Се «

WITH

70 s khz" " ate 5 of them, b)

Fo iF) ime) 60 b5

8337 СНнзе сн сн Н ОН SeО t

B343 снснео сн СН Н ОН СеО сч о

That) :

В3Ba Ri СН СН СН С8О ke, oyu - zv k

V3B nesSene SN SN SN On S-eo «

There are 5 of them, b)

Fo iF) ime) 60 b5

333 Riz snsN N N ON SeO t

В339 снен Н Н Н ОН M-сН sch o

Te) : v418 Rpza N N N ON M-sN ke, oyu - zv k

B423 (снНаБсНн СНа Н Н Он М-СНа «

There are 5 of them, b)

Fo iF) ime) 60 b5

443 СНзва Н сн Н ОН М-сН t 8В455 несен Н СН Н ОН М-сН счо

Te) : в474 СНО СН СН Н ОН M-сН ke, ою - звк вВ47з (СНа»MeО» СН СНа Н On M-СНа «

There are 5 of them, b)

Fo iF) ime) 60 b5 y

BOB RyBO сн сн сн ОН m-сН then you сНязс сНесНн Н N ОН M-сН сх o s »| vv | here nn b o vV5ZO sn N N N ON re) yours! 1 St | nH | nn Her n ono 71 oyu visa" | sniyunsn | N | n HER non os. vase | (snasSN | n | n | n (| on 77770 | "I

And IIA | (svv | But ІІ nn Her non 0071 k p ee 115 vo snavo Н Н Н ОН and вшя | sniaО. | Н | nn Her n ono and вшя 1 R ІІ noi noi non 0 | « louse | sto І n ІІ n | n (on os | Z t 1 vshcho | stSb, | n | n Her n (ono s vi | stssou | nN | n ІІ n on os "z vm | snia-sSNSN.Ї | n | n | n | on o . NN | nn HER n ono ih i ovya | R HER no HER n/ Her non os vav | - RB | n | n | n (| on 77770 s I university | RNVO | nN HER nn HER n ono b) vo | royu Her nN HER nn HER n Her on! os vi! | cm І noi noi no on 70.

F I vBbae | St | sv I no Her n ono

And vBa | ss | with | n | n it

And inBya | snansn. | with | nH | n ono zv 1 VBB | (snshsn | ssh | n | n | on | oo

F) ko) bo 65 vBB | (svyus | ssh | n | n | on 77 o vBU | se | sv n | n | on o g Fzh KKMZHSK(( vBV | svo | ssh | nn | on 777071 | VBBYAO | sno | sv | n | n | ono

SHE NN ANNA YAN NN NN Zh

В5Б1 Сн сн Н N ОН vB. | ssSo; | with. | n 1 n | he is 70. va | sshstso | dream | n | n | he o0os in 0 sneSNSN. | Dreams n 1 no | he 0 e | vshb | nsssyu | sleep n | non 170 s she 1

V5By S Na» MZO sn N N ON

EV | (German s | n | n | on 770 va | RYU | ssh | nn | on 7707171 5 | vo | R | snvn| n | n on 0 g gj KK

TU 177777 FISH | US | n 1 no | on 777071 va 1 RAVoi | with. | nn on 77071. va | cm | dream | but | n | he o0os

I 177 dream | But svt no | on 777701 | vv | snsn | n | Article | but | he chose | all | n | here n | he - ZRBoo vVB7 177 snshsn | but | sv no | he Her 77770171.

KILLED | (svvs | no | st no! he osSsS u va | sne | N | s | n | he 0 zh JUK sch | VO | svo | n | sv | no | he Her 770 g o in 17 snyas. | n | st n | on 777071 vva | Ri | n | c |

Vo5ab snAsnNen H SN N ON ke,

BV 177 nsssn. | n | ssh but | he 77770. oyu

BB 17770 s | NOI st no! he os in vve | (snshmvo; | n | sv | n | on (rhOo (Ky | cha zv 8880 | (sym | nN | s | N | on; KO | m v591 RO N SNa N On

Ш НН МНШИНЕ an НЕ Ш вБе3 1000 RBO // | But | St no | he Her 777770. in 0 RAVOH | n | st no | on 7777071 | « ve | cm | n | with | n | he 0 g Fzh "KM - t | wav | hundred | Article | US | n | oni777 o s vu 17 snsni | US | ssh but | he Her o17171 u» 1 VBaV | snstsn, | sleep | with. | n | he o0sS " ve | snaSsno | sn | St | no | on Her 7777071 in 177 isvas 7 | ssh | ssh no | ono i-5. 1 Vii | svv | sne. | sv | n | on | (o zh R« (( their v» 17 so | ssh | Sv | no | he Her 7777071 their VZ 1 sno» | shh | st no | he Her osSsS u voi | R | ssh | s | n | on .(u/o0 C 5 , at 17 so | sun | sSsh0 | no | on Her 7777701. entry 2 1 Vb | stso; | sv | ssh | n | on Her 0 g f (in voi | ststso; | sn | sv | n | on ( rpvRo (BbC

Fo VV 0000 sneSNSNe | dream | Svsh in no | he Her 77770. vya / nossn. | shn | ssh but | on 77071 in 177 s | shn | ssh but | ono zv 1 VT | o (snm5o, | sna. | sv | n | on | 0 g iF) ime) 60 b5 in GT sshzh Is IsfI it viz 1 in 1 sv | sv non 0 va 17 yati 77531 st | with i background, 0-

Spvye | RIO 1 st. st, but at 0-- you | bai |i vno

ВБ1y СМ сн сн H On vyv 17 5 3 s 1 ss s on 9 va | sleep 1 st | svi svi on 0 svo 1 snsvsni 1 s | svi svi on, 77 0--- e Govei | snasn o 1 sna 1. sleep; St | on07 | 0

SHE MN SHE YAE JAK I NI NN

VB23 SNizz sn sn sn va 177 sno 1 s 1 sv sno

His firstness; 3731 se | with | Article | he, 0----- in Povyoe 1 in 1 dream. Saints, Saints he | 0 vu 17 sleep 77171 s | sf sf on, 77 0- vv | stso; 31 s US | St | he, 0--- vve | ststso; 1 s St | St | he 90 svo 1 sndsnsni 1 sn | svi svi on, 77 0--- 2 ovi 1 nsssv Z 1 sv | US | svi | he 17 0---- va | 3737320 sv 1 ssh | US | sf on | 0

Ssvvzya 100 ispayyaou 31 sleep. | svi svi | on, 7 9-- va 1 7 sleep 95 51 se | so | St | he 0 sv | 33308 7011 s | with | sf on | 0 credits for SOVE56O 1-9 22 RI 5 31 dreams | svi svi | he 170 o you 1 RIO 531 st | owl | with | he 1-0 sv 100 Fish 3031 sv | St | svi | he | 0 va. 175 sc 7777 1 s | sv sv on 0 at 17 I stand in my own way, 7 0--- F "vo | shuye (ve i 8 vno wba2 snzveN snzsna| N N ON ova 17 sshos 1 sen no i- 1 on, 7 0-- - yu va | 7 svv 3 sovi NO - 1 o, 7 0---- svv | svo 00 sshend noi no, on | 0 - vve 1 stvo; seni no i- 1 on, 9--- ts "Pi 5 151505

VB48 SNzo snzsn N N an vva 17 sto, svv no ja- 1 on, 0-- svo 1 ststsb; spsvi n-| i- 1 o, 7 0---- «

SsvBI | snesnsn svi noi | on 2277370 Z t ov; | Nosovu sen noi no o 77790 so stva 1 s own! n- | I oh, 0--- that Owl | erase sen noi noi on | 32373720 toovv5 | sne o svend no noi o 7779 vie | 5 53 8 7 stitches n-| i- 1 o, 0-- w Owls | 85 3 sen noi no he 73390 zo sov6 15 Rvo 3 (ssheni NO i- | o, 0-- in Sova 1 Rovou svi NO I he he 0 his | 3 cm 11 his no no no he | 0 s o

F with o name) 60 bo

Y vByZ stsneso N N N ON 5 th

VByZ Ro N N N on Ziv sch zv o

F

»

VBUV SE sn N N On Z ke, yu - z cv/oz RO SNa N N ON Z «

Z o s g ' z - v s 0»

Ф зв о име) 60 bo vV/23 snen sn Н ОН Z t

B735 СНзза сн СН СН НОН С сч о

Te) : вВ754 СН СН СН СН СН ОН Z ke, oyu ch k

AND

В7БО СсНИСО СН СН СН СН ОН З « - то с хз» " и и и 5, b)

Fo iF) ime) 60 b5

785 SE снсН Н N ОН Z t v/v Rpza сНнзсН Н Н ОН Z scho

That) :

Va S NaaM N N N ON re) ee, yu ch zv m

Ва15 СМ Н Н Н Он -50 « - to с хз» " и и и 5, b)

Fo iF) ime) 60 b5

B841 СсНнЗБсНн Н сн Н ОН re) t

Ва47 СНО Н СНН НОН according to sch o

That) :

VaBB СНззО СН СН Н ОН re) ke, yu - zv cha

You SnIstsSO» СН СНа Н On -50 « - to с хз» " и и и 5, b)

Fo iF) ime) 60 b5

BaUb SEz SNz SNz SNz On zZO02

WHO SM SN SN SN ON zi " 2 cm 2 o ino 22 Riza snzen n N ON za yu " zv t vz2gv sNasneNn N N N ON sneO2snsn " no s. z - і p. go

F

F dv iF) ime) 60 b5 vU53 SNnze sn N N ON sneOozsnIsn t university snsneo sn N N ON sneozhnen sch o te) : taught Ri N SN N ON snesOonInke, oyu - zvk zasSene N SNa N On SnN(SO "SnNoSNn"yai "

There are 5 of them, b)

Fo iF) ime) 60 b5 in Ro sn sn N OH sneOozsnIsnt t 1015 snen sn SN sn OH sneojnen scho te) : 81034 Rpza SN SN SN OH snesOonIn ke, oyu - zv k

WHO

There are 5 of them, b)

Fo iF) ime) 60 b5

ViOvo sniststsn

TOBI sNiSsNisN v'Ov2 сН(с(сН

CART

WTO SN (SE

VITOB5 sposo S(SNZKSE

VIV SISNASE

VIOB7 stoso v'OvV 70 vovya | hundred 0 Ssnoso no | sleep | he | 7777 sno vTO?O vii 81072

WTO? сн(ОосН 81074 снИи5СШСН

VI075 vI0?B siSNsN

VI027 nOo (sn

IOV MON vi? nosnesnasn ovo мМ8Оосн(сНсН vovi сНнасН виОВ82 nssesn

WTO83 Ns-sen sch o

In the following table, 7 O represents the group Ov

Kk 83 e (se) with () v4 so and v 85 o "I o Uu (Ov), v. (СНо)р « 20 Kk ve sh s "with this Ob represents the following C radicals: - And their o b 50 4!

F) co) bo 65

Table and

Radicals С сч (о) со

Zo o) in "I - " in c. - e 5. th

F

F rya (F) ko bo b5

Sy snasa N Nn On 4 SN t

SseZ SN N Sh on v. SN sch o

That) :

Sag nesen СН Нн ОН 4 СН ke, oyu ch zv m

Sai Riz SNa Nn OH 4 SN; "

There are 5 of them, b)

Fo 5v iF) ime) 60 b5 y s116 snasnasNn sn N an Z sn to t5 sch o s zo o o s what i- « - " s c149 Н Н в! ОН 5 сн "з " -1 45 In the following table 8 O represents the group Ov 1 Kv ( )

F Kk vo

Ф (Ов), о Ки (СН)о о А with име) while Од represents the following radicals 0: бо б5

Table C

Radicals 0 of 2 2 and 70 2 7 o5 7 Her ysnas | n | n Her n | he | 2 2 08 | hundred | n | n | n | dream | 2 ra 777777 own. | nn | n Her n | he | 2 2 2 2 2 2 2 from 2 2 2 sch 2 2 i) 2 2 2 so 2

Zo 2 Ge) 2 2 yu 2 « 2 2 - 2 2 2 « 2

З З З З . Z nya Z

WITH

WITH

- Z

З З s З го З

F Z

F Z

WITH

Z rya Z (F) ko bo b5 z

Z a y Z rey snzzN sn N N On Z a a vo svo 21111 sv | BUT | n- 1 on 1 3 and a

Z rez СНзО сн N N on Z

WITH

From Sat 317 Sun 1 Sun 1 Sun He | 3 a

From an owl 717 RO 231 sv nn on 13 a go A and p

A i sh z z o l i i l F raz snASNSN N N N ON 4 o i yu

A and - with p y rai RAB N N N ON 4: i vo 717 own 1 st | n | non | la « і Z o V s l g» і ' і rev 73177 se 31 s n- | n- 1 on 1 a i - i in Svv 1 pine 1 sy 1 nn 1 noi on i sl p still A i

F i l l zv Z

F) name) 60 bo pov 1 rt 1 ri1to sposo 1 r snsnOoso 1 113 СНае сн Н N ОН 1 ri14 sneVO 1 0115 сНабО» 1 riv сНасН 1 to 2117 stosa stsn 1 pr119 СНос СнасНн Н N ОН 1 0120 stsn 1 ri sto STSN 1 0122 SNNBO STAN 1 0123 Sniss 1 p124 Flashes 1 0125 SNZSN; VO 1 0126 Snan Stan 1 0127 Snabsno Stan 1 0128 Growing Stan 1 P129 1 P13O 1 0131 1 so zo 0137 1 0138 1 se) r139 1 oyu r14p snsnOosO 4 " m. " - s:z"

-I s" (9) b 50 4)

(F; ko 60 65

Table U

Compounds of the formula Her

Ka o and 84 t oz (1) -

Kk av M Kk z

Spol. Mo Ra Na Rada Ra p

AB 1 sshschos | 7 nn | se | vm scho o 14 RO N N SE V24 so so o oyu - zv m « : 70 to snsn N N SE vo s "z " - their s b)

F

(F. ko 60 65

AD SNiz5 N N SEzSE 24 t

ABZ snAsn NN SEgZSE В24 sch o te) :

A Ri N N SEzZSESE В24 ke, oyu - zv k

AI SNaz N N SRaSgSE" v24 "

There are 5 of them, b)

Fo iF) ime) 60 b5

OZ RO N N SES 24 t

OZ SE N N SRS B24 account) :

A128 SNісНн Н Н СНЕ В24 ke, oyu - k

AND

A134 RizZ N N SNE B24 «

There are 5 of them, b)

Fo iF) ime) 60 b5

159 СсНнисН Н Н сс 24 t

A1B5 Rpza N N ss B24 scho te) : 184 sn N SN SE B24 ke, oyu - zv k 189 SnNiISNI" schi Sne CEa v24 "

There are 5 of them, b)

Fo iF) ime) 60 b5

215 iclopropyl H CH SEzSE 24 t

Aga Ri N SN SEgZSE B24 sch o te) :

Ag SNizOSN H SN SEZSE B24 ke, oyu - zv k

Ag45 (SNavs N Sne SRaSgSE" v24 "

There are 5 of them, b)

Fo iF) ime) 60 b5 da sn H SN SES 24 t

A snzaosn H SN SRS B24 sch o

That) :

Ag SsnizeNn N SN SE V24 ke, south - zv cha do Ssnisn; shchi Sne SNE" v24 " - to s khz" " their 5, b)

Fo iF) eat) 60 b5 and

Aa СНО сн Н Сн СНЕ 824 to dz33 iclopropyl Н сн СС 824 сч о с!

Aza sNU'MO N sn Shaw 824 re) oyu « zv k

Aa N N Ri CEa 824 «

WITH

70 s h» " - their s b)

F

(F. ko bo b5 y

AzZaZ SsNzsNn N Re CE 824 to dz iclopropyl N Ri SgaSE 824 sch o so :

Ada SsNzvOZMOSN N RE SEZSE 824 re) oyu « zv k

AD13 sneasNn" N Ri SEBACE" 824 "

WITH

70 s "from " - their s b)

F

(F. ko bo b5

AdAZ СНзЗмМ 5 N Ri SEzSgSE 24 t

Ad4A5 sn H Ri SRS B24 sch o te) :

AABA snAsn N Ri SES B24 ke, oyu - zv k

AABZ STeSn» N Ri SES! in24 "

WITH

70 s khz» " ие их» 5, b)

Fo iF) ime) 60 b5

AAU SsNnzO Men N Ri SNE 24 t

OR SNizzO sn N Ri SNE B24 sch o te) :

Ba nes N Riss B24 ke, oyu - zv k

AB25 (SNavMm shchi Ri Sov v24 "

There are 5 of them, b)

Fo iF) ime) 60 b5

AB H snsnNeN H Se 24 t

ABY N SNzZOHsN N SE B24 sch o o:

ABY N sne N SEZSE V24 ke, oyu - zv k

Aa N (SN MO" N StaSt"e v24 "

There are 5 of them, b)

Fo iF) ime) 60 b5

OR N SNI N SEzSgSE 24 t

AB13 H snen H SRS B24 sch o te) :

ABZ N SNeESNeN N SE В24 ke, oyu - zv k

ABZ N SsnaOsSNn" N SE v24 "

There are 5 of them, b)

Fo iF) ime) 60 b5

ABZ N SSNIEN N SNE 24 t

ABBZ N SNzvs N ss B24 account) : dra N SNI N ss B24 ke, oyu - zvk

ABZ N SNa Sne SEa v24 «

WITH

70 s khz" " there are 5 of them, b)

Fo iF) ime) 60 b5 y d"19 H sNnaUvBOSN sn SE В24 tho

ATB N snsn sn sSEaCE 824 сх о со !

At N snesn sn SEZSE B24 re) oyu « zv k

AgAZ N cyclopropyl SNa SgaSvoCE" 824 "

WITH

70 s "from " - their s b)

F

(F. ko bo b5

AKB N snen SN SES 24 t dev N snuafen SN SRS B24 sch o te) :

AVOO N SNzZOHSN SN SE B24 ke, oyu - zv k

АВЙ5 Н (снНИЬsН Сне СНЕ» v24 «

There are 5 of them, b)

Fo iF) ime) 60 b5

AVZ1 N SNzvo SN ss 24 t

AZY N Ra SN ss B24 sch o o:

АВББ N snen Ri SE В24 ke, oyu - zv k

AVB1 N SnazOoSsno Ri CEa v24 "

There are 5 of them, b)

Fo iF) ime) 60 b5

Aa N SsNnisN Ri SEzSE 24 t

AVUZ N ryza Ri SEgZSE B24 sch o

That) :

A12 N SNzve Ri SEzZSESE В24 ke, south - zv k

A N Ry Ri SRaSgSE" v24 "

There are 5 of them, b)

Fo iF) ime) 60 b5

Az H snzfgsNn Ri SES 24 t

Az H SN Ri SRS B24 sch o

That) :

AB N SsNnisN Ri SNE V24 ke, oyu - zv k

LOW N Riz Ri SNE" v24 "

WITH

70 s khz" " ate 5 of them, b)

Fo iF) ime) 60 b5

Aa N ro Ri ss 24 t

ATO N SE Ri ss B24 sch o

Te) : 1024 spsnesSNOo N N SE V24 ke, oyu h zv m

ATO VgsSn" N N CEa v24 "- to c khz" " their 5, b)

Fo iF) ime) 60 b5 and that

A1072 sn N SI SE B24 sch:

А1075 сн Н СНО СЕ Б24 i)

Ф со ю « о - и о, (Iv) « | - s t z» SE; M sn, - killed; vovi vv vbo/ vo vv ve vo took to the village

F

Photo 229 08230 8231 8232 8233 8234 8235 8236 8237 | 8238 | B239 | 8240 o iv sch 2 o

Ф зо Ф ю з t " b з е г" в - з зо

F

F zv o u vo

Vot VLOTa VIT VLOTe WTO WTO LOT Lov Lovy IOV Vovz 65

; o ns with (IP) 10 s

Se; М сн, и5 в/в вва Вб вв в) вв) ве | where are you? 20 sc o o zo F her - shcha 7 " zo Z s g" - t sl zo

F

F o where; because b5 VB577 |vB578 | 85798580 8581 8582) 8583 8584 8585 8586 | B587 | B588 I and 2 sch o

F

» F and her /v'otz vlot4 Vi075 B1076|B1077|B1078 Vi0te V'OVO|VIOV1 Vo Vo - « o - s with m, (Kk) and Z x hiz - sl SE; SbMm7 cTesnen, bu 0

Fo vi va | vv vv vbo c) vv vve v v vv) v v o vv vbo 8157 8158 /8159)/8160 8161 8162 8163/8164 8165 B166 B167 | B168 o iv sch 2 o

Ф зо Ф ю з t " b з е г" в - з зо

F

Ф z o u v o 65 v-L1531o4z 81049 81050 81051 81052/81053/81054|81055 81056 81057 ИВ81058/Щ81059 81060

/vio73 в1074 В1075|В1076 В1077|В1078 В1079 ВИОВО|В'О81 ВИ082)В1083). in) in) in | in | do you have 2 sch 25 o o zo i yu

M

35 them « 40 Z s "z " 45 them their t

Pho and

F. Yuyu at 65 8553 8554 | 8555 | 8556 | 8557 8558 8559 | 8560 | 8561 | 8562 8563 | VB564

' i5 sch 2 o

Ф з Ф вы « » M vlotz|v'ota|v'o75 Vio76 VI077 VI078 Viote V'ovo|Vovi|VlOv2 V'oVI them 0 Z s :» 9 - -5 OO. (Iv) h sl -y b) v.SIS M sn,

F vva in/v | Vb vbo/ vo vo ve vo vi) v? o t bo bo B145 | B146 | B147 | B148 | B149 | B150 | B151 | 8152 | B153 | 8154 | B155 | B156 o iv sch 2 o

Ф зо Ф ю з t " b з е г" в - з зо

F

F z o yu vo 65

Vtoov VIov BIO VTO Tue Tue 1037 v1038 81039 81040 81041 81042 81043 81044 81045 81046 81047 | B1048

(вло7з влота |в1от75|В1076 В077 В1078|В1079 В'ОВО ВИОви|ВИо82|В'OV3S 70 о и | о, (То) -- сСЕСЕ; мМ" sen, о в'|в2 |в | ви во) vbo / в? ве ве во в | vyg) sch o

Ф with Ф ю " with t "

Y Z s :» in - 2 s zo

F

Ф z o u v o b5 8529 8530/8531 8532 8533 8534 8535) 85368537 8538 8539 8540

; about me, sch o

Ф з ю ой ч з з /в1о73 |в'074 В1075|В1076 В1077 |В1078 В1079|В'ОВО ЛОВИ В'ОВ2 ВЛОВ3| « - s i o; -AND

M 7 Oz (Ir) sl c) -

Fu SE.SEOSE. М СН, в в2 | with | in | vBo/ web) in | вв) ве | vlo v vis o o v b5

B133 8134 | 8135 8136 | 8137 | 8138 8139 | 8140 ) 8141 | B142 | B143 | B144 o iv sch 2 o

Ф зо Ф ю з t " b з е г" в - з зо

F

F z o yu vo 65

Vtotz VLota Tu Vot VTOTT W121-1019 of that WTO (VTO vtoo VOo v1025/81026 81027 81028 81029 81030 81031 81032 | 81033) 81034 | 81035 | 81036

(V'ota Vot Vot VIOTe VIOTT V'OTv Vot Vovo ViovI VIoveVova oh and oh, 1 ate | (id) -

SE. M vb| in" wav | вв вв вво ве |в выв? school

F zo

Fu ch i- « 8 p. 4 z - g p

Fo and 5 o yu » b5

VB517 | 85188519 8520 8521 8522 8523 | 8524 | 8525 | 8526 | B527 | B528

, i5 sch o

Ф з Ф во « » M « ю Iv'otzvl1ot4 В1075 В1076|В1077 |В1078|В1079 В'ОВО В'О81|В'082 В1083) | З7З s; t 8! -I g" i i Ov (Iv)

Pho -

F SE. SMm' sen, with o still o 65

С121С1221С123 Сс124 С125 С1261С127 1С1281С1291С130|С213112132 stz3|с134|с135|с136|с137 |С138 |с139|с140|С141|С142|с143|с144 status ostavistat status 18 status 2 Tabviso

Compounds of formula i5 10 o i SE men a veTveTvv TveTvvi v Tvt ov Tov voTeitvh, 2 he vyuoT ovi ovo ovzT ovi vvvTovv BT yav ov oo. ovi Tovo oz ovi vv ev tv ev pyuv tot t. sch tv /pev tu pev vvi vot rot vo pyuz voe/ pov vv. o (09? | 098. 089 (0100 0101/0102|0103 0104 |0105|0106|0107|0108 p109|0110|0111/0112 01130114 |0115|0116 0117 0118 |0119|0120 2212120120121201212012015 |0127|0128 0129 0130 |0131|0132 so zo riz3ziri34 0135 ri36 ri37 ri3Viri3900140000001 (Se)

Table 19 o

Compounds of the formula m chE o: if M (IM) - .

I" e o SE - Z r" 1 20-n-propyl

ФЕЗ sno i (снг)зосн име) skzkoyat bo (СНг)о r bo Е15 (СсНнг)гО(СНг)гОсНЗ о счо дв 10azalzv 0 caught the darkness roar | 0000000 sq lovlyu 00 lav o 0000omyuyu 01000010 Ф зовв /0озввавт 0lavvo000osmya 1000 Ф vtovv o kvyetalyanortya | lab 0000osmlya 0100001 (vo! | fristalichnrna As | 000omale//|11 in vva 0 bistalnyta | lava? 000osmeyayu 100 « vev have 0 layumo /000omyuyu 17111011 zv web 000zvolv; 0 loviovt smorna rezhyu | 0000 t vvvvmyu1010001010001010101010 vv 00 lava 00omey 010000

Ovoto | crystal black | IMPORTS | 000lmaolo//|1 «

Compounds of formulas 2.1 and 2.3-2.13.c are known under the names imazamox, imazethapyr, imazaquin, imazapyr, ne) c dimethenamid, atrazine, terbuthylazine, simazine, terbutrin, cyanazine, ametrine, terbumeton, prohexadione-calcium, c» sethoxidim, clethodim, tepraloxidim , flumetsulam, methosulam, pyridate, bromoxynil, ioxynil, sulcotrione, carfentrazone, sulfentrazone, isoxafluton, glufosinate, primisulfuron, prosulfuron, rimsulfuron, halosulfuron, nicosulfuron, ethoxysulfuron, flasasulfuron and thifensulfuron and are described in (Reziiside

Mapia!Y, 11th ed., ed., Vol. , 146, 49, 339, 495, 626, 88, 425, 664, 112, 665, 436, 382, 589, 613, i» 644, 389, 519, 287, 325 and 704). A compound of the formula 2.13, in which M 4, XM3 and Mu mean methine, Xo means C-1, K74 means COOMe, U5 means nitrogen, U means methyl, and U; means the methoxy group known as iodosulfuron (primarily in the form of the sodium salt) with | ASCOM Mo296, January 16, 1998, p.22). The compound of the formula b 20 2.13, in which U 1, Mo, Mu and Mu mean methine, K7/ means trifluoromethyl, U5 means nitrogen, M means trifluoromethyl, and U means a methoxy group, known under the name tritosulfuron and described in OB-A that 4038430. The compound of formula 2.13, in which M 4 means MH-CHO, M», M3 and Mu mean methine, K74 means

COoMMe", U5 means methine, and U and U7 mean a methoxy group, described, for example, in (MO 95/29899).

The C-enantiomer of the compound of formula 2.12 is registered in the SAB under reg. MoI35597-44-5). Compound 29 of the general formula 2.2, i.e. akzv,15(-)M-(1-methyl-2'-methoxyethyl)-M-chloroacetyl-2-ethyl-b-methylaniline, and compound (FI of the general formula 2.3, i.e. (15, ac5)-2-chloro-N-(2,4-dimethyl-3-thienyl)-N-(2-methoxy-1-methylethyl)acetamide, described, for example, in MO 97/34485). The compound of formula 2.9, in which Kvo stands for MO", is known under the name of mesotrione and is described, for example, in (05 5006158). A compound of formula 2.6 in which K is ethoxy, K is fluorine, U is methine, K is methoxycarbonyl, K is hydrogen, and K is chlorine is known 60 as cloransulam, for example, with |! ASCOM Mo261, August 2, 1996, p.21). The compound of formula 2.6, in which

Kv" means methoxy group, Kvz means hydrogen, U means C-E, Kol means fluorine, Ke5 means hydrogen, and Kev means fluorine, known as florasulam and described in (05 5163995).

In addition, the following compounds, which can be part of the composition proposed in the invention, are described in (Reziiside Mapiai, 11th ed., ed-vo Vgiyizy Stor Rgogesiop Soipsii, 1997: b5

The compound of the formula (name) Me in Reviiside Mapiai, 11th ed.

wound 000018 o and cm 5 o o

The compound of formula 2.7, in which Kv7 means hydrogen and the method of its preparation are described in (05 3790571), and the compound of formula 2.6, in which Koso means an ethoxy group, 7 means nitrogen, Kz means fluorine, Kvi means chlorine, Ke5 means hydrogen, and Kev means chlorine, described in (05 5498773). The compound of formula 2.21 and the method of its preparation are described in (005 Shcheo, 5183492), and the compound of formula 2.22 is known under the name isoxachlorotol and is described in | BUT TO WHOM Mo296 dated January 16, 1998, p. 22)1. The compound of formula 2.31 is known under the name fentrazamide and is described in |materials

From the conference on the protection of agricultural crops "Te 1997 Viiiivy Stor Rgoiesiop Sopiehepse - M/eeadv", v. vol.1, 2-8, pp.67-72), and the compound of formula 2.32 is known under the name UM 485 (isoxapropazole) and is described in the materials of the conference on the protection of agricultural crops "Pe 1997 Vgyivy Stor Rgoiesiop Sopiegepse - Meedzv", vol.1 , ZA-2, pp. 93-98). The compound of formula 2.44 is known under the name pentaxamide and is described, for example, in (EP-A 0206251). The compound of formula 2.45 is known under the name procarbazone and is described, for example, in (EP-A 0507171), and the compound of formula 2.46 is known under the name fluazolate and is described, o) c, for example, in (5 5530126). The compound of formula 2.47 is known under the name cinodon-ethyl and is described, for example, in (OE-A 4037840Y. The compound of formula 2.48 is known under the name benzphendisone and is described, for example, in (MO 97/08953)Y. The compound of formula 2.49 is known under under the name diflufenzopyr and is described, for example, in (EP-A 0646315). The compound of formula 2.50 (amicarbazone) and the method of its preparation are described in |(0О 298393 and in 05 5194085). The compound of formula 2.51 (flufenpyr-ethyl) is described in |(Abzvigasiv) oi Raregv Ategisap Spetisai! - zosieiu, 2000, vol. 220, part 1, p. ASKO 174) ih During the creation of the invention, it was unexpectedly established that the effect of using a combination of the active ingredient of the formula | with one or more active ingredients from among the compounds of the formulas 2.1-2.51 1 exceeds the total effect in the fight against weeds, which in principle should be expected from the use of 20 such active ingredients separately, thanks to which the spectrum of action of each of these individual active ingredients is expanded, primarily due to yam of the two following aspects. The first of them consists in reducing the rate of consumption of individual compounds of formulas I and 2.1-2.51 while simultaneously maintaining their action at a fairly high level, and the second is that the composition proposed in the invention allows to fight weeds with high efficiency even in in those cases when the use of individual compounds in small doses is impractical and ineffective from an agronomic point of view. As a result, it is possible to significantly expand

GF! spectrum of weedy plants with which it is necessary to fight, and to additionally increase the selectivity in relation to cultures of useful plants, which is a necessary condition in case of accidental overdose of the active ingredient. o The composition proposed in the invention not only ensures highly effective destruction of weeds in crops of useful plants, but also provides great freedom in the choice of crops that are expected to be cultivated next on the same 60 sown areas.

The composition proposed in the invention can be used to control a wide range of agronomically important weed plants, such as Zielyiagia, Maziipit, Aadgoviiz, Oidnagia, Amepa, Zeyiagia,

Zipariv, And ot, Zoiapit, Razeoii5, Espipospioa, Zsigriv, Mopospogia, Zadiniagia, Vgotiv, APoresiigiv,

Zogopyt Ppaierepze, KoiroeiPa, Suregiz, AbBshyop, bida, Hapiyisht, Atagapipy5, SPpeporodisht, Irotoea, bo Spgyzapiyetit, Saiisht, Mioia | Megopis The composition according to the invention allows its use by all methods usually used in agriculture, and in particular is suitable for processing before germination,

processing after germination and seed treatment. The composition proposed in the invention is suitable for weed control primarily in crops of such useful plants as grain crops, rapeseed, sugar beet, sugar cane, plantation crops, rice, corn and cultivated soybeans, as well as for non-selective control of weed plants . "Crops" in the context of this invention also mean crops in which, as a result of traditional methods of selection or genetic engineering, tolerance to herbicides or their entire classes has been developed. The present invention also offers a method of combating the growth of unwanted plants in crops of useful plants, which consists in treating the cultivated plant or its growing area with a herbicidally effective amount of the composition according to the invention. 70 The composition proposed in the invention contains in the mixture the active ingredient of the formula I and the active ingredients of the formulas 2.1-2.51 in any ratio between such components, but usually one of these components is present in excess relative to the other components. In general, the ratio in the mixture (by weight) between the active ingredient of formula I and other components of the mixture, which are compounds of formulas 2.1-2.51, is from 1:2000 to 2000:1, preferably from 200:11 to 1:200. The consumption rate can vary widely and depends on /5 the nature and properties of the soil, the treatment method (treatment before or after germination, seed treatment, application to the seed furrow, treatment of uncultivated land, etc.), cultivated plants, weeds , with which they are fighting, climatic conditions prevailing in one or another area, and other factors caused by a specific method of processing, time of processing and the target cultivated plant. The rate of consumption of the mixture of active ingredients proposed in the invention can usually be from 1 to 5000 g of the mixture of active ingredients per 2 hectares. Mixtures of compounds of formula I! with compounds of formulas 2.1-2.51 can be used in an unmodified form, that is, in the form in which they are formed as a result of synthesis. More preferably, however, they are processed by conventional methods together with excipients commonly used in formulation technology, such as solvents, solid carriers or surface-active substances, to obtain, for example, emulsifying concentrates, directly sprayed solutions or solutions that of dilutable, diluted emulsions, wettable powders, soluble powders, dusts, granules or microcapsules.

Processing methods, such as spraying, misting (fine-droplet spraying), i) dusting, etching, spreading or watering, as well as the type of preparation, are chosen according to the objectives and the prevailing circumstances.

Preparative forms, i.e. compositions, compositions or mixtures, which contain compounds (active ingredients) of the formulas Hezo II 2.1-2.561 and usually one or more solid or liquid auxiliary substances (adjuvants) used in the technology of preparation of preparative forms, are obtained according to known method, for example x, by homogeneous mixing and/or grinding of active ingredients with adjuvants, for example solvents or solid carriers. In addition, surface-active substances (surfactants) can also be used in the preparation of preparative forms. "

Examples of solvents and solid carriers are described, for example, in (MO 97/34485 on p. bi. i-

Nonionic, cationic and/or anionic surfactants and mixtures of surfactants with high emulsifying, dispersing and wetting properties are used as surface-active substances, depending on the active ingredient included in the preparation form, formulas I.

Examples of anionic, nonionic and cationic surfactants suitable for this purpose are described, in particular, in (MO "

Z1/34485 on p. 7 and 8). In addition, for the preparation of the herbicidal compositions proposed in the invention, surfactants commonly used in the technology of preparation of preparative forms are also suitable, which are described, in particular, in | MS Scispeopye of Oegegdepiv apa EtyiviNegv Appia!", ed. MS Rybiizpipud Sogr., Kiddezhmooy Mem/ degvzeu, 1981, in ebYaspe N., "Tepvid-Tazspeprisi", ed. Sagi Napseg Megiad, Mypisp/Mieppa, 1981 , and in M. ii 9. Av, "Epsusioredia oi zipasiapiv", vol. 1-II, ed-vo Spetis! Rybiizpipd So., Mem Hogk, 1980-8111. -i Usually herbicidal compositions contain from 0.1 to 9Omas .95, primarily from 0.1 to 95wt.9o, a mixture of active ingredients that contains a compound of formula I and compounds of formulas 2.1-2.51, from 1 to 99.9wt.9o of a solid or liquid excipient included in the preparation form , and from O to 25mas.9o, primarily from 0.1 "sl to 25mas.9o, South Africa.

If as products that are supplied for sale, of course, compositions or compositions in the form are preferred

Me. concentrates, then the end user, as a rule, uses diluted preparations. Such drugs can

F also contain other additives such as stabilizers, such as vegetable oils or epoxidized vegetable oils (epoxidized coconut oil, rapeseed oil, or soybean oil), antifoams, such as silicone oil, preservatives, viscosity regulators, binders, adhesives, and fertilizers or other active substances. Preferable ov preparative forms have the following composition (U6-wt.9o). o Emulsifying concentrates: a mixture of active ingredients: 1-9095, preferably 5-2095

Surfactant: 1-3095, preferably 10-2095 in a liquid carrier: 5-9495, preferably 70-8595

Powders: mixture of active ingredients: 0.1-1095, preferably 0.1-595 solid carrier: 99.9-9095, preferably 99.9-9995 b5

Suspension concentrates:

mixture of active ingredients: 5-7595, preferably 10-5095 water: 94-2495, preferably 88-3095

South Africa: 1-4095, mostly 2-3095

Wettable powders, a mixture of active ingredients: 0.5-9095, preferably 1-8095

Surfactant: 0.5-2095, preferably 1-1595 solid carrier: 5-9595, preferably 15-9095

Granule: mixture of active ingredients: 0.1-3095, preferably 0.1-1595 solid carrier: 99.5-7095, preferably 97-8595

Below, the invention is illustrated by non-limiting examples.

E1. Emulsifying concentrates a; b) c) mixture of active ingredients Buyu 1095 2595 5095 calcium dodecylbenzenesulfonate byu 895 695 8905 polyglycol ether of castor oil 495-495 495 (36 mols of ethylene oxide) polyglycol ether of octylphenol - Azh - 25 Ge (7-8 mols of ethylene oxide) o cyclohexanone - - 1095 2095 mixture of aromas. of Se-C12 hydrocarbons 85 7895 5595 1690

Emulsions of any required concentration can be obtained from such concentrates by dilution with water. (That)

E2. Solutions a) 6) c) ise) a mixture of active ingredients Buyu 1095 5095 9095 and 1-methoxy-3-(3-methoxypropoxy)propane - 20952095. - polyethylene glycol, MM 400 20961095 - - «

M-methyl-2-pyrrolidone - - ZO 1095 - a mixture of aromas. hydrocarbons Со-С12 TB bo - -

Such solutions are suitable for use in the form of microdrops. "

E3. Wettable powders a; b) c) - o c mixture of active ingredients Bob 2595 5095 8090 sodium lignosulfonate 4U 0-39 - :z» sodium lauryl sulfate 290 ZU - 495 sodium isobutyl naphthalene sulfonate - bUb 5BUb 695 polyglycol ether of octylphenol - 19 29 - -I (7-8 moles ethylene oxide) highly dispersed silicic acid 195 395 595 1095 o kaolin 88956295 3590 - 1 0. | | | | and

The Active Ingredient is mixed to homogeneity with excipients and the resulting mixture is thoroughly (2) ground in a mill suitable for this purpose, obtaining wettable powders that can be diluted with water from

F by obtaining suspensions of any required concentration.

E4. Coated granules a) b) c) a mixture of active ingredients О 19 B 1595 highly dispersed silicic acid b 29 290

HF) inorganic carrier (2 0.1-1 mm), for example, CaSoOz or 5iOo 99.095 9395 8390 ko in . more

The active ingredient is dissolved in methylene chloride and sprayed onto the carrier, after which the solvent is evaporated in a vacuum. 60

E5. Coated granules a) b) c) a mixture of active ingredients О 19 Б 1595 polyethylene glycol, MM 200 1.095 295 Зо highly dispersed silicic acid b 195 295 бо inorganic carrier (2 0.1-1 mm), for example CaSoOz or 5iОо 98.095 9295 8095

The finely divided active ingredient is evenly applied in a mixer on a carrier moistened with polyethylene glycol. In this way, dust-free granules with a coating are obtained.

Eb. Extruded granulate a) b) c) a mixture of active ingredients 0.195 ZU 5BUyu 1595 sodium lignosulfonate 1.595 295 Z95 495 carboxymethyl cellulose 1495 2956 295 295 kaolin 97.095 9395 9095 7995

The active ingredient is mixed and ground with auxiliary substances and the resulting mixture is moistened with water. This mixture is then extruded and then dried in a stream of air.

Eh? 7. Powders a) b) c) mixture of active ingredients 0.195 195 595 talc 39.95 4995 3595 kaolin 60095 BO 6096

Ready-to-use duets are obtained by mixing the active ingredient with carriers and grinding the resulting mixture in a mill suitable for this purpose.

E8. Suspension concentrates a) b) c) d) a mixture of active ingredients Zo 1095 2595 5090 ethylene glycol Buyu BUyu 5 590 sem polyglycol ether of nonylphenol - 196295 - o (15 moles of ethylene oxide) sodium lignosulfonate 395 ZU 495 590 carboxymethyl cellulose 195 195 195 195

C790 aqueous formaldehyde solution 0.295 0.295 0.295 0.295 (Ce) silicone oil emulsion 0.895 0.895 0.895 0.895 so water 8796 7995 6295 3895

Io)

The finely divided active ingredient is mixed to homogeneity with auxiliary substances, obtaining a suspension concentrate, from which, by diluting with water, suspensions of any required concentration can be obtained. what-

In practice, it is often more expedient to separately prepare compositions based on the compound of formula I and the component or components of the mixture of formulas 2.1-2.51 and then, shortly before use, combine these compositions in water in a suitable processing device in the required quantitative ratio to obtain the so-called "tank" mixtures".

Biological examples - c A synergistic effect occurs when the effect of a combination of active ingredients, i.e. compounds from formulas I and 2.1-2.51, exceeds the total effect achieved when using each of the active ingredients separately.

The expected herbicidal effect of U/e for a given combination of two herbicides can be calculated using the following Colby formula | see SOI VM 5.K., "SaIsciainpo zupegadizviis and apiadopiziis gezropze oi Pegriside sotrbipaiiopv", -I UUEedvs 15, pp. 20-22, 1967):

MMe-x -(m.(100-X)/10901,

ЧК" where 1 X is expressed as a percentage of the herbicidal effect when treated with the compound of formula I! at the consumption rate of r kg per hectare

Fu 50 compared to untreated control (-090),

In percent, the herbicidal effect when treated with the compound of formula 2.1-2.51 at the rate of consumption of 4 kg per 42) hectare in comparison with the untreated control,

Me expected herbicidal activity (herbicidal activity as a percentage of the untreated control) as a result of treatment with compounds of formulas | and 2.1-2.51 at the consumption rate of rad kg of active ingredient per hectare.

When the action actually observed exceeds the expected value of U/e, a synergistic effect occurs. o The presence of a synergistic effect when using the compound of the formula | in combination with compounds of formulas 2.1-2.51 is confirmed by the following examples. eat) Description of the experiment: action before germination

Monocotyledonous and dicotyledonous experimental plants are sown in plastic pots with standard greenhouse soil mixture. Immediately after sowing, treatment with tested compounds in the form of a water suspension (500 liters of water/ha) is carried out by spraying. Consumption rates depend on optimal dosages determined separately for field conditions and greenhouse conditions. After that, experimental plants are grown in a greenhouse under optimal conditions. The effect of herbicides on experimental plants is evaluated after 36 days (action at 95, 10095 corresponds to the complete death of the plant, 095 corresponds to the absence of phytotoxic action). Examples that confirm the presence of a 65 synergistic effect when using the compositions proposed in the invention are presented in the following tables B1-8B6.

Mixture A contains as active ingredients the compound of formula 2.2a in the amount of 915 g/l and the compound of formula 3.1 in the amount of 45 g/l. and

Watt 00003611

Speloroyut 1110101011110000000 vva 01111111001ю11111111611т

W 0100000ю1ю0001ю

Spelorvyut 11010096 9 vva at 011011to111111e6111

W 01000600ю1ю001ю

Spelorvyut 11010095 vva o 011011to111111e6111 with more breporeyut 00016160

Zbeteya 13901110 vva 11111101 1111110 o "so yu breporeyut (00000010 - zv zfeteya 00009000 a vva 10161610 "

Y - breporeyut (00000010 s et 11110100

I" vva 10161610

Description of the experiment: action after germination

Experimental plants are grown in plastic pots in greenhouse conditions until the stage of 2-3 leaves. For cultivation, standard greenhouse-greenhouse soil mixture is used as a substrate. At the stage of 2-3 leaves, experimental plants are treated with herbicide individually and in the form of a mixture. For processing, an aqueous suspension of the tested compounds in 500 liters of water/ha is used. Consumption rates depend on optimal dosages, which are determined separately for field conditions and greenhouse conditions. The effect of herbicides on experimental plants is evaluated through

Ge") 250 ZZ days (action in 95, 10095 corresponds to the complete death of the plant, 095 corresponds to the absence of phytotoxic action).

Examples that confirm the presence of a synergistic effect when using the compositions proposed in the invention are presented in the following tables B7-B10.

Mixture A contains as active ingredients the compound of formula 2.2a in the amount of 915 g/l and the compound of formula 3.1 in the amount of 45 g/l. about t feya 01000001 in Rowvyutit 10110190091000000000100ю0

Haliut 18016161 b5

Research plant | 1.001 (12.5g/ha| Mixture A ISOOOg/ha)| Spol. 1.001 (12.5g/ha| - mixture A ISOOOg/ha| Me according to Colby tele 17711930, 9, 815

Rowvyutii 01909015

Hapnsht 17777810 1gvv11vo feteya 00000101 and voudutt 11000010

Khamisht 17777770 110 111vo1 and fairy 01000001

Rowvyutii 01909015

House number 17771111

The data in the following tables correspond to the data obtained when evaluating the herbicidal effect after 14 days. school

Rowdolt 17775017 80|777777111ге6|1vo

F zo

F

Road inquiry 17775017 BO17777777777711gvo11tv yu « z k

Roadopyut 17713018 " o 2 s "" means methyl. voudopyt 17777710 |77771vo 17777716 -I 2 sl i.

F Roadopyut 177 v0177 30 171v1v6 4) 8 o ko v b5

Sveloroyaut 00080000 viaasht 18601008 bure 17777ho11ho1view1 11 th

Sreporyut (08600101 iv vvaet 010000015600001000060010001010100080000000000100050 burashe 17777761 111vo »

Sveloroyaut at 00006600 sch in storm 17777010 Я11111ю11o o

F

7 o

Vaalit o 17776161 oyu « zv M burem 177771 177771go1111111111vo1lyu

The data in the following tables correspond to the data obtained when evaluating the herbicidal effect after 31 days. h - s d"

Road survey 17777012 - And what's going on?

F o Roadopyt o 17777о01о1гмю1 11 o yuyu

Fairy 01016161 bo Khapisht 17778118 c

Research plant | Spol. 1.001 (25g/ha| Spol. 2.4.a (25Og/ha| /Spol. 1.001 (25g/ha| their Spol. 2.4.4 (25Og/ha| | UMe according to Colby

NNYA PI LYN AMBASSADOR NO NN

Khapisht 17771801 1111111111gv11111111va eteia 0000000000100000000000000000860000000000001000

17778012 means nitrogen, 7 means methine, and Keb means fluorine.

Bowdopot 16130101

The data in the following tables correspond to the data obtained when evaluating the herbicidal effect after 21 days. School phone number 01036101 o

Review 00000750000100000000001000000000968

Khapycht o /17777vo1yu 11111111 (Se) zo

Fyu rotova ///1777783011vo1111e611t " z ye " yu Roadopyt 17777 76171o1vo1vya Z s "z ' 75 Boudopot o 177801o018o111111130 -I g"

F

FU in Rotova 17730121 ov o yu eto 00000030

Road survey 17777300 11711 bo vv

Table B36b 2 The compound Me2.1.65 corresponds to the compound of the formula 2.1, in which К51 means СНоОМе, and Кб2 means hydrogen.

Research plant Spol. 1.001 (25 g/ha)|Spol. 2.1.5 (ЗОгига)|Spol. 1.001 (25g/ha| x spol. 2.1.5 Izogiga| Me according to Colby

Roadoliot at 1711175180111111186011111111va

The data in the following tables correspond to the data obtained when evaluating the herbicidal effect after 23 days.

Table B37

Action before germination

Compound 2.13.65 corresponds to the compound of formula 2.13, in which K74 means -"COOMe, each of U1, U2, uz and U4 means methine, U5 means methine, and

Mv and Z7 mean a difluoromethoxy group.

Spol. 1.001 (bg/ha) | Spol. 2.13.5 (Bg/ha) | Spol 1.001 (bg/ha) x spol. 2.13.5 (15 g/ha)

Speropodiyt

Table VZ8

Action before germination

Research plant | 1.001 (bg/ha)|Spol. 2.13.s (bOg/ha)|Spol. 1.001 (bg/ha) « spol. 2.13.s (bOg/ha | Me according to Colby. speporodimt tab vz9 s avlytsia 2 and o

Action before germination

Compound 2.13.a4 corresponds to the compound of formula 2.13, in which M, Mo, Uz and M4 mean methine, K74 means trifluoromethyl, U5 means nitrogen, b means trifluoromethyl, and U7 means a methoxy group.

Research plant Spol. 1.001 (bg/ha| Spol. 2.13a (7.5g/ha) Spol. 1.001 (bg/ha)| - spol. 2.13.a. Me according to Colby "so (7.Bg/ha) 300 dAtavnnye 7 | 77771711ju1711111vo1711111111111hev111111va Ge

When creating the invention, it was unexpectedly established that special antidotes are suitable for use in a mixture with the composition proposed in the invention, which has a synergistic effect. Therefore, this invention also relates to a composition of selective herbicidal action for combating cereal grasses and weeds in

From cultures of useful plants, primarily in crops of corn, which contains a compound of the formula I, one or more of them - compounds from the number of compounds of the formulas 2.1-2.51 and antidotes (antidotes) and protects useful plants, but not weeds, from the phytotoxic action of the herbicide, and as well as the use of such a composition for weed control in crops of useful plants. "

In accordance with the invention, it thus offers a composition of selective herbicidal action, the composition of which, along with the usual inert auxiliary substances used in technology c) c for the preparation of preparative forms, such as carriers, solvents and wetting agents, as an active ingredient "" includes a mixture of "a) a herbicidally-synergistically effective amount of a compound of formula I and one or more compounds from the number of compounds of formulas 2.1-2.51 and b) a herbicidally-antagonistically effective amount of a compound selected from the group that includes - a compound of formula 3.1 t o 1 (o ) 4) (3.1), and C name) 60 compound of formula 3.2 b5

WITH

- M

M

SI compound of formula 3.3 18 SI vai (3.3), sh

M счо о-сн,с(0)-0о-сСН(СН)СНН en o compound of formula 3.4 "со

IS)

Sime soosnsn, ch ch- si M (84

Mo zhnn « co M teoosnsn, z c » the compound of formula 3.5 c; ш ш ш» 1 шч M me si (3.5), o p 42) and A / o Me o the compound of formula 3.6 ime)

СсОон " СсоОоНн (3.6), about 18 the compound of formula 3.7

SI about

SI about

Me

M (3.7), sch 7 Me o

M

Me F o "co

IS o) the compound of formula 3.8 « z5 СИ и- « i (3.5), З - Шко, г» se, o щ 45 the compound of formula 3.9 k СССНСОМ(СТеСН-СНИ» (3.9), and 50 the compound of formula 3.10 ( o) oe-ou I was the S

SI sho 67 7 Zo--sn; (3.10), about M her SE, 70 compound of formula 3.11

С с ж (3411), the compound of formula 3.12

UNO i c o (3.12) c o i thi ethyl ether, (Ce) compound of formula 3.13 c o snsn, her c i -

Where o " z SI M (3 . IZ), shi s st IM z s - 45 SI " S o b compound of formula 3.14 (o)

F SN, o o

N N o M-e N

OGO, sv 6o o X-th b sn, 7 compound of formula 3.15 th o (15 r zho

Z o and the compound of formula 3.16 -- m. sh-y M

You m-- (3.16).

M sch z m" To o (Se)

Not about

The present invention also relates to a composition of selective herbicidal action, the composition of which, along with the usual inert auxiliary substances used in the technology of preparation of preparative forms, such as carriers, solvents and wetting agents, as an active ingredient includes a mixture of "a) a herbicidally effective amount of the compound of the formula | and b) a herbicide-antagonistically effective amount of a compound selected from the compounds of formulas 3.1, 3.2, 3.3, 3.4, 3.5, 3.6, 3.7, 3.8, 3.9, 3.10, 3.11, 3.12, 3.13, 3.14, 3.15 13.16.

Preferred compositions according to the invention contain as an antidote a compound from among the compounds of formulas 3.1, 3.3 and 3.8.

Such antidotes are most suitable for use as part of the compositions proposed in the invention, which "contain the above preferred compounds of formula I and optionally compounds of formulas 2.1-2.51.

The most effective compositions are, as it was established, combinations of compounds of formula I! with the compound - c of the formula 3.1, with the most preferred being the compound of the formula | is a compound Mo1.001. Such a composition "z is preferably used together with the compound of the formula 2.2a p sn, shchi Ф(0)-СН,СИ ' ' / (2.2a, ak5,1 sh(-)M-(1'-methyl-e M 2- methoxystyl)-M- t ne---sn.,osn, chloroacetyl-2-ethyl-6-"ia

FI methylaniline)

F s.n. CH,

This invention also relates to a method of selective control of weeds in cultures of useful plants, which consists in the fact that useful plants, their seeds or petioles or their cultivation areas are treated with a herbicidally effective amount of the herbicide of formula I, if necessary, with one or more herbicides from among compounds of formulas 2.1-2.51 and an antagonistically effective amount of the antidote of formulas 3.1-3.16. име) Compounds of formulas 3.1-3.16 are known and described, for example, in (Reziiside Mapia), 11th ed., Vgyiizy Sgor

Rgoiesiop Soipsii, 1997, under numbers 61 (formula 3.1, benoxacor), 304 (formula 3.2, fenclorim), 154 60 "(formula 3.3, clochintocet), 462 (formula 3.4, mefenpyr-diethyl), 377 (formula 3.5, furilazole) , 363 (formula 3.8, fluxofenim), 213 (formula 3.9, dichlormid) and 350 (formula 3.10, flurazole)). The compound of formula 3.11 is known under the name MOM-4660 (Mopzapis company) and is described, for example, in (ER-A 04364831.

The compound of formula 3.6 (AC 304 415) is described, for example, in (EP-A 0613618), and the compound of formula 3.7 is described in

IOE-A 2948535). The compounds of formula 3.12 are described in |OE-A 4331448), and the compound of formula 3.13 is described in (|OB-A 65 3525205)|. The compound of formula 3.14 is known, for example, from (05 5215570), and the compound of formula 3.15 is known from (EP-A 0929543). The compound of formula 3.16 is described in vv (|MO 99/00020). In addition to the compound of formula 3.16, others

3-(5-tetrazolylcarbonyl)-2-quinolones are described in (MO 99/00020), while the most suitable for protecting cultivated plants from the phytotoxic effect of compounds of the formula | there are primarily compounds listed mainly in tables 1 and 2 on pages 21-29.

Cultivated plants, the antidotes of formulas 3.1-3.16 can provide protection from the unwanted effects of the above-mentioned herbicides, are mainly grain crops, cotton, soy, sugar beet, sugar cane, crops cultivated on plantations, rapeseed, corn and rice, primarily corn. "Cultivated plants" also include plants in which, as a result of traditional breeding methods or genetic engineering, tolerance to herbicides has been developed, according to different classes of herbicides. 70 Weeds with which they are fighting can be both monocotyledonous and dicotyledonous weedy plants, for example Z(eiPagia, Adgoviiv, Oidnaga, Amepa, Arega, Vgaspiagia, RnNaiagiv, Zeigia, Zipariv,

Ioiysht, BZoiapit, EsPpipospioa, Zsigriv, Mopospogia, Zaditsagiia, Rapisit, Vhotiv, APIoressygiv, Bohuapyt

NaiIerepze, Zoguopyt bBisoiog, Koibroea, Suregiz, Arshiyop, bida, Hapipisht, Atagapiyiv, Speporoditst, Irotoea,

Sphyzapipetitis, Saiisht, Mioia and Megopisa.

Cultivation areas include land plots with already sprouted or grown cultivated plants or land plots already sown with the seeds of these cultivated plants, as well as soils allocated for the cultivation of these cultivated plants on them.

The antidote of the formula 3.1-3.16, depending on the purpose of application, can be used for pre-treatment of seed or planting material of a cultivated plant (treatment of seeds or petioles) either before or after 2o wrapping the seeds in the soil. However, treatment with an antidote can be carried out individually or together with a herbicide and after the emergence of plant seedlings. Thus, treatment of plants or sowing material with an antidote can in principle be carried out regardless of the time of herbicide treatment. At the same time, plants can be treated simultaneously with both means - a herbicide and an antidote (for example, when using them in the form of a tank mixture).

The ratio between antidote and herbicide consumption rates largely depends on the processing method. So, for example, when processing fields, which may consist in the application of a tank mixture containing a herbicide in combination with an antidote, or in the separate application of an antidote and herbicide, the ratio between the amount (8) of herbicide and the amount of antidote is usually from 100:1 to 1:10, preferably from 20:1 to 1:1. When processing fields, the consumption rate of the antidote, as a rule, is from 0.001 to 1.0 kg/ha, preferably from 0.001 to 0.25 kg/ha.

The rate of consumption of herbicides is usually from 0.001 to Bkg/ha, preferably, however, from 0.005 to 0.5 kg/ha. Hezo Treatment with the compositions proposed in the invention can be carried out by all the usual agricultural methods, such as, for example, pre-germination treatment, post-germination treatment and x, seed treatment. When treating seeds, the consumption rate of the antidote is usually from 0.001 to 10 g per kg of seeds, preferably from 0.05 to 2 g per kg of seeds. If antidote treatment is carried out in liquid form shortly before sowing when the seeds are swollen, then it is advisable to use antidote solutions with a concentration of

With the active ingredient from 1 to 10,000, preferably from 100 to 100 parts/million. uh-

For processing antidotes of the formulas 3.1-3.16 or such antidotes in combination with the herbicide of the formula | and, if necessary, with one or more herbicides from the number of compounds 2.1-2.51, it is advisable to process together with auxiliary substances usually used in the technology of preparation of preparative forms to obtain appropriate preparations, for example, emulsifying concentrates, coating pastes, directly "sprayed solutions or diluted solutions, diluted emulsions, wettable powders, water-soluble powders, duets, granules or microcapsules.

Similar preparative forms are described, for example, in (MO 97/34485 on pages 9-13). Such preparatory forms;" obtained by a known method, for example, by homogeneous mixing and/or grinding of active ingredients with liquid or solid excipients used in the composition of preparative forms, for example, solvents or solid carriers. In addition, surface-active substances (surfactants) can be additionally used when preparing preparative forms -I. Examples of solvents and solid carriers suitable for this purpose are described, for example, in MO 97/34485 on page b). As surface-active substances, depending on the compounds of the formulas included in the composition of the preparative form, I, 2.1-2.51 and 3.1-3.16, nonionic, cationic and/or anionic surfactants and mixtures of surfactants with

High emulsifying, dispersing and wetting properties. Examples suitable for this

Me, the purposes of anionic, nonionic and cationic surfactants are described, in particular, in (MUO 97/34485 on pages 7 and 8). Except

In addition, for obtaining the herbicidal compositions proposed in the invention, commonly used in the technology of preparing preparative forms of surfactants, which are described, in particular, in "Meoscispeop'z YuOefegdepiv apa

EtyiviNegz Appiai!", ed. MS Rybiizpipd Sogr., Kiddezhshooi Mem/Oegveu, 1981, in 5iaspe NN. "Tepvid-Tazspeprisi", ed. Sagi Napseg Megpiad, Mypspep/l//ep, 1981, and in M. and 9. Av, "Epsusioredia oi zipasiapiv", vol. 1-II, vid-vo Spetis! Rybiizpipd So., Mem Hogk, 1980-8111. (F) Herbicidal compositions usually contain from 0.1 to 9Omas.9o, primarily from 0.1 to OBbws.U5, active ingredients in the form of a mixture of compounds of formula I, compounds from among compounds of formulas 2.1-2.51 and compounds of formulas 3.1-3.16, from 1 to 99.9Uws.95 of a solid or liquid auxiliary substance used in composition of the preparative form 60, and from 0 to 25wt.9o, first of all from 0.1 to 25wt.9o, surfactant. If as products that are supplied for sale, compositions in the form of concentrates are preferred, then the end consumer usually uses diluted preparations.

Such compositions may also contain other additives such as stabilizers such as vegetable oils or epoxidized vegetable oils (epoxidized coconut oil, rapeseed oil or soybean oil), antifoams such as silicone oil, preservatives, viscosity regulators, binders, adhesives, as well as fertilizers or other 65 active ingredients. Various methods and technologies are suitable for the use of antidotes of formulas 3.1-3.16 or compositions that contain them, in order to protect cultivated plants from the unwanted effects of herbicides of formulas I and 2.1-2.51, for example, described below.

I) Seed treatment a) Seed treatment is carried out using the compound of formula 3.1-3.16 prepared in the form of a wettable powder by shaking in a suitable vessel until the drug is evenly distributed over the surface of the seed (dry treatment). At the same time, approximately 1 to 500 g of compounds of formula 3.1-3.16 are used (from 4 g to 2 kg of wettable powder per 100 kg of seed material. b) Seed treatment with an emulsifying concentrate of compounds of formula 3.1-3.16 is carried out according to the above-described method a) (wet treatment). 70 c) Etching of seed material is carried out by immersing it for 1-72 hours in a working solution that contains from 100 to 1000 parts per million of compounds of the formula 3.1-3.16, and then the seeds are dried if necessary (wet etching by immersion).

Seed treatment or sprouted seed treatment are obviously the preferred treatment methods, as with such treatment the active ingredients fully interact with the target crop. The rate of consumption /5 of the antidote is usually from 1 to 1000g, preferably from 5 to 250g per 100kg of seed material, while the rate of consumption depending on the method, which also allows the addition of other active ingredients or microelements, may differ from the specified limit values as much as as well as the smaller side (repeated etching).

I) Processing in the form of a tank mixture

In this case, a mixture of antidote and herbicide is used, which is brought to a liquid state (with a mutual quantitative ratio of components from 10:11 to 1:100), while the herbicide consumption rate is from 0.005 to 5.Okg per hectare. Processing with similar tank mixtures is carried out before or after sowing.

I) Insertion into the seed furrow

Compounds of formulas 3.1-3.16 in the form of an emulsifying concentrate, wettable powder or granules are introduced into the open sown seed furrow. After closing the seed furrow, pre-germination treatment with a herbicide is carried out in the usual way. and)

IM) Controlled release of the active substance

Compounds of formulas 3.1-3.16 are applied from a solution to a mineral granular carrier or to polymer granules (urea/formaldehyde) and dried. Then, if necessary, you can apply an additional coating (granules in a Hezo shell), which allows the active ingredient to be released in dosed amounts over a certain period of time.

The compounds of the most preferred compositions according to the invention (95 - 90 wt.) are presented below. X,

Emulsifying concentrates: a mixture of active ingredients: 1-9095, preferably 5-2095

Surfactant: 1-3095, mostly 10-2095; liquid carrier: 5-9495, mostly 70-8595

Powders: "mixture of active ingredients: 0.1-1095, preferably 0.1-595 c 40 solid carrier: 99.9-9095, preferably 99.9-9995 C "» Suspension concentrates: n mixture of active ingredients: 5-7595 , preferably 10-5095 water: 94-2495, preferably 88-3095 - and surfactants: 1-4096, preferably 2-3095 t Wettable powders 1 mixture of active ingredients: 0.5-9095, preferably 1-8095

Me, South Africa: 0.5-2095, mostly 1-1595

I") solid carrier: 5-9595, preferably 15-9095

Granules: mixture of active ingredients: 0.1-3095, preferably 0.1-1595

GF) solid carrier: 99.5-7095, preferably 97-8595 o Below, the invention is illustrated by examples that do not limit its scope.

Examples of compositions in the form of mixtures of herbicides of formula I!, optionally herbicides of formulas 2.1-2.51 and 60 antidotes of formulas 3.1-3.16 (905 - wt. 9o)

E1. Emulsifying concentrates a; b) c) mixture of active ingredients Buyu 1095 2595 5095 calcium dodecylbenzene sulfonate buyu 895 695 8905 bo polyglycol ether of castor oil 495-495 495

(36 moles of ethylene oxide) polyglycol ether of octylphenol - Up to - 25 (7-8 moles of ethylene oxide) cyclohexanone - - 1095 2095 mixture of aromas. hydrocarbons C9-C12 8595 7895 5595 1695

Emulsions of any required concentration can be obtained from such concentrates by dilution with water.

E2. Solutions a) 6) c) then a mixture of active ingredients Buyu 1095 5095 9095 1-methoxy-3-(3-methoxypropoxy)propane - 20952095. - polyethylene glycol, MM 400 20961095 - -

M-methyl-2-pyrrolidone - - ZO 1095 mixture of aromas. hydrocarbons Со-С12 TB bo - -

Such solutions are suitable for use in the form of microdrops.

E3. Wettable powders a; b) c) mixture of active ingredients Bob 2595 5095 8090 sodium lignosulfonate 4U 0-39 - sodium lauryl sulfate 290 ZU - 495 diisobutylnaphthalene sulfonate sodium - bUb 5BUb 695 polyglycol ether of octylphenol - 19 29 - s (7-8 moles of ethylene oxide) o highly dispersed silicic acid 195 395 595 1095 kaolin 88956295 3595 -

The active ingredient is mixed to homogeneity with auxiliary substances and the resulting mixture is thoroughly ground in a mill suitable for this purpose, obtaining wettable powders that can be diluted with water to obtain suspensions of any required concentration. (Se)

E4. Coated granules a) b) c) o mixture of active ingredients O 19 B 1595 hI highly dispersed silicic acid b 29 290 inorganic carrier (2 0.1-1 mm), for example CaSoOz or 5iOo 99.095 9395 8390 t

The active ingredient is dissolved in methylene chloride and sprayed onto the carrier, after which the solvent is evaporated in a vacuum. "

E5. Coated granules a) b) c) o, c mixture of active ingredients O 19 B 1595

Iz» polyethylene glycol, MM 200 109 295 390 highly dispersed silicic acid b 195 295 inorganic carrier (2 0.1-1 mm), for example CaSoOz or 5iCo 98.095 9295 8095 sh- The finely divided active ingredient is evenly applied in the mixer to the carrier moistened with polyethylene glycol. In this way, dust-free granules with a coating are obtained. 1 Eb. Extruded granulate a) b) c) d)

FO 50 mixture of active ingredients 0.195 395 BU 1595 sodium lignosulfonate 1.595 295 Z95 495 42) carboxymethyl cellulose 1495 2956 295 295 kaolin 97.095 9395 9095 7996

The active ingredient is mixed and ground with auxiliary substances and the resulting mixture is moistened with water. This mixture is then extruded and then dried in a stream of air. to E7. Powders a) b) c) mixture of active ingredients 0.195 195 595 in talc 39.995 4995 3590 kaolin 60095 BO 6096

Ready-to-use duets are obtained by mixing the active ingredient with carriers and grinding the resulting mixture in a mill suitable for this purpose. b5 sho

E8. Suspension concentrates a) b) c) d)

mixture of active ingredients Зо 1095 2595 5090 ethylene glycol Buyu BUyu 5 590 polyglycol ether of nonylphenol - 196295 - (15 moles of ethylene oxide) sodium lignosulfonate 395 ZU 495 590 carboxymethyl cellulose 195 195 195 195

C790 aqueous formaldehyde solution 0.295 0.295 0.295 0.295 silicone oil emulsion 0.85 0.895 0.895 0.890 water 8796 7995 6295 3895

The finely divided active ingredient is mixed to homogeneity with auxiliary substances, obtaining a suspension concentrate, from which, by diluting with water, suspensions of any required concentration can be obtained.

In practice, it is often more expedient to separately prepare compounds based on compounds of formulas I, 2.1-2.51 and 3.1-3.16 and then, shortly before use, combine these compounds in water in a suitable device for processing in the required quantitative ratio to obtain a so-called "tank mixture" .

The ability of antidotes of formulas 3.1-3.16 to protect cultivated plants from the phytotoxic effect of herbicides of the formula is illustrated in the following examples.

Biological example: Protective action as an antidote

Experimental plants are grown in plastic pots in greenhouse conditions until the stage of 4 leaves. At this stage, experimental plants are treated with herbicides only, as well as mixtures of herbicides with tested compounds, which are studied for their effect as antidotes. The treatment is carried out with an aqueous suspension of the tested compounds, obtained from the 2590th wettable powder (example EZ, b)), with a consumption of 500 l of water/ha. 4 weeks after treatment, the phytotoxic effect of herbicides on cultivated plants, such as corn and cereals, is evaluated in the medium as a percentage.

At the same time, 10095 corresponds to the complete death of the experimental plant, and 095 corresponds to the complete absence of phytotoxic effect.

The results obtained in this study indicate that the use of compounds of formulas 3.1-3.16 allows to significantly reduce the damage to cultivated plants by the herbicide of formula I, used in combination with one or more herbicides from among the compounds of formulas 2.1-2.51. In the table B40 below as an example, some of the results of the study of the protective effect of antidotes obtained in this experiment are presented

Table B40: plant |/(BOg/ha) (BoOg/ha|

The same results are obtained when using mixtures of compounds indicated in examples E1, E2 and G4-E8. their village

The formula was invented from rum. du 1. A composition of selective herbicidal action, which, in addition to the commonly used in the technology of preparation of preparative forms of inert auxiliary substances, contains as an active ingredient a mixture of and a) a herbicidally effective amount of the compound of the formula i" o "I c) 5. C (22) Sh- 4 ») (The mouth in which

K In each case independently means hydrogen, C.i-Svalkyl, Co-Svalkenyl, C»o-Svhaloalkenyl,

Co-Svalkynyl, Co-Cvhaloalkynyl, C3-Cvcycloalkyl, C.-Cvalkyloxy, C.-Cvhaloalkyl, o C-Cvalkylthio, C.i-Cvalkylsulfinyl, C.--Cvalkylsulfonyl, C.i-Cvhaloalkyl, C.i-Cvhaloalkylthio ,

C.i-Svhaloalkylsulfinyl, C.-Svhaloalkylsulfonyl, C.i-Svaloxycarbonyl, C.-Svalkylcarbonyl, imo) Si-Svalkylamino group, di(Ci-Svalkyl)damino group, S.i-Svalkylaminosulfonyl, di(C--Svalkyl)aminosulfonyl . , phenoxy group, phenylthio group, phenylsulfinyl or phenylsulfonyl, while the phenyl group can in turn be mono-, di- or tri-substituted by S.-Svalkyl,

C.i-Swhaloalkyl, C3z-Swalkenyl, C3-Swhaloalkenyl, C3-Swalkynyl, C3-Swhaloalkynyl,

C-Svalkoxy group, C.-Svhaloalkyl group, C3-Svalkenyloxy group, C3-Svalkynyloxy group, mercapto group, C.i-Svalkylthio group, C.-Svhaloalkylthio group, C3-Svalkenylthio group, 65 Cz-Svhaloalkenylthio group, C3-Svalkynylthio group, Svalkynylthio group, Cs-Svalkylthio group, Salkylthio group ,

C3-Salkyloxycarbonylalkylthio group, Co-C.cyanoalkylthio group, C.-Salkylsulfinyl,

Claims (1)

C-C-S-haloalkylsulfinyl, C-S-alkylsulfonyl, C-S-haloalkylsulfonyl, aminosulfonyl, C1-Soalkylaminosulfonyl, Co-C.dialkylaminosulfonyl, C.--S.alkylene-Cl5 group, MEdeCad? group, halogen, cyano group, nitro group, phenyl or benzylthio group, and the last two groups, which are the phenyl and benzylthio groups, in turn, can be substituted in the phenyl ring by C-Szalkyl, C.-Szhaloalkyl, C.-S-Alkoxy group, C.--C.Shalo-Alkoxy group, halogen, cyano group or nitro group, or K in each case independently means a monocyclic or fused bicyclic ring system with 5-10 members, which may be aromatic or partially saturated and may contain from 1 to 4 heteroatoms selected from nitrogen, oxygen and sulfur, while such a ring system is either directly attached to the pyridine ring, 70 or attached to the pyridine ring through a C 1-C;, alkylene group, each ring system cannot contain more than two oxygen atoms and not may contain more than two sulfur atoms and the indicated ring system may be mono-, di-, or tri-substituted in turn with C.-Swalkyl, C.-Swhaloalkyl, C3-Swalkenyl, C3-Swhaloalkenyl, C3-Swalkynyl, C3-Swhaloalkynyl, C. --Svaloxy group, C.--Shaloalkyl group, C3-Svalkenyloxy group, C3-Svalkynyloxy group, mercapto group, C1-Svalkylthio group, 75. C1-Cvhaloalkylthio group, C3-Cvhaloalkylthio group, C3-Cvhaloalkenylthio group, C3-Cvlkynylthio group, Co-Cvalkyloxyalkylthio group, C3-Cvacetylalkylthio group, C3-Cvoxycarbonylalkylthio group, Co-C.cyanoalkylthio group, C.-Cvalkylsulfinyl, C.-Cvalkylsulfonyl, C.-Cvalkylsulfonyl , C-Svhaloalkylsulfonyl, aminosulfonyl, C.i-Soalkylaminosulfonyl, Co-C.dialkylaminosulfonyl, C.-S.alkylene-K7 group, MKaCo group, halogen, cyano group, nitro group, phenyl or benzylthio group, 2o and phenyl and benzylthio group in turn can be substituted in the phenyl ring by S.--Szalkyl, C.-Shaloalkyl, C.sub.-C.sub.alkoxy group, C.--C.sub.haloalkyl group, halogen, cyano group or nitro group, while the substituents near the nitrogen atom in the heterocyclic ring are different from halogen, or K in each case independently means C.i.d.-C; alkoxy-Si -C;alkyl or C1-C;alkoxy-C1-C;alkoxy-C.-Alkyl, t means 1, 2, C or 4, c Ku, E»z and K5 each independently of each other means hydrogen or C. -Svalkyl, Ko means MK/oKi, C-Svaloxy group, C.i-Svhaloalkyl, C.i-Svalkyl, C.4-Svhaloalkyl, i) C3z-Svalkenyl, C3-Svhaloalkenyl, C3-Svalkynyl, C3-Svhaloalkynyl, C3 -Cicycloalkyl or phenyl, while phenyl can in turn be substituted by C.i-C alkyl, C.-C haloalkyl, C.-C alkyloxy group, C-Cshaloalkyl, halogen, cyano group or nitro group, He or Ki means MK.2K.iz, C-Csalkyloxy, C.i-Cshaloalkyl, C.i-Salkyl, C.4-Chaloalkyl, C3z-Salkylenyl, C3-Cshaloalkenyl . S.-Shaloalkyl group, halogen, cyano group or nitro group, Kv; means | MK.AKiv, Ci-Swhaloxy group, C.i-Swhaloalkyl, C.i-Swalkyl, C.4-Swhaloalkyl, - Cz5 Cz-Swalkenyl, Cz-Swhaloalkenyl, Cz-Swalkynyl, Cz-Swhaloalkynyl, Su-Seccycloalkyl or phenyl, at the same time, phenyl y- can in turn be substituted by S.i-Szalkyl, S.-Szhaloalkyl, S.-Szalkoxy group, C.-Shaloalkyl group, halogen, cyano group or nitro group, K; and Kyav each, independently of each other, means a C.sub.-C.alpha. C-Salkylthio group, C-Salkylsulfinyl, C-Salkylsulfonyl or phenyl, while phenyl can in turn be substituted by C-Salkyl, C-Shaloalkyl, C-Salkoxy group, C-Shaloalkyl group, halogen, - by a cyano group or a nitro group, Kv, Ko, Ki", K44 and Kab each independently of each other means hydrogen or S.-Svalkil, ;" Co, K41, Kis, Ki5, and Ku7 each independently represent a C.i-Svalkyl or a C-Svaloxy group, O represents a CO group. o (90, and Kv sh» o el P; vu and Kv 4") in which Kiv, Ki, Kiv and Kio each independently of each other means hydrogen, a hydroxy group, C.4-C; alkyl, Co-Svalkenyl, Co -Svalkynyl, C.-S.Alkoxycarbonyl, C.-Svalkylthio group, S.i-Svalkylsulfinyl, C1-Svalkylsulfonyl, C4-Slalkyl-MH(O)", C1-Shaloalkyl, -MH-C.-Sulfyl, -Щ( C.i-Sualkyl)", C-Sualkyloxy group, cyano group, nitro group, halogen or phenyl, which in turn can be substituted by C 4-C alkyl, o C.1-Chaloalkyl, C.i-Salkoxy group, C.-C.alkyloxy group, C.-C.alkylcarbonyl, c.-C.alkoxycarbonyl, amino group, C1-Alkylamino group, di(Ci-C.alkyl)amino group, C.i-Svalkylthio group, C.-Svalkylsulfinyl, C1-Svalkylsulfonyl, C.-Slalkyl-5(0)20 group, because C.-Salhaloalkylthio group, C.-C.haloalkylsulfinyl, C.-Shaloalkylsulfonyl, C1-Shaloalkyl-5 group (0)20, C4-Slalkyl-Z(0)2MH, C4-Slalkyl-5(0)2M(C1-Salalkyl), halogen, nitro group, COOH group or cyano group, or two adjacent substituents from Kv, Ki7, Kv and Co form a Co-C alkylene bridge, Cor means a hydroxy group, OM' (where M' is an alkali metal ion), a halogen, a C.4-C.ioalkyloxy group, b5 a C.-C.oalkylcarbonyloxy group, a Co-C.alkenylcarbonyloxy group, C3 -Seccycloalkylcarbonyloxy group, C.-Ci2alkylcarbonyloxy group, C.-Ci2alkylcarbonyloxy group, Kg1Ko24M-Щ(О0, C.-Cioalkylthio group, C.1-C/2alkylsulfinyl, C.-Ci2alkylsulfonyl, C.1-C/haloalkylthio group, C.1-C/haloalkylsulfinyl, C.1-C.haloalkylsulfonyl, Co-Ci2alkenylthio group, Co-Ci2alkenylsulfinyl, Co-Ci2alkenylsulfonyl, Co-Cihaloalkenylthio group, Co-C1ohaloalkenylsulfinyl, Co-C1ohaloalkenylsulfonyl, Co-C.2oalkynylthio group, 500 C2-Ci2alkynylsulfinyl, Scl2-Cil. .i-Slalkyl-5(0)20O, phenyl-5(0)20, (C1-Slalkoxy)2P(O0, C.i-Slalkyl(C1-Salkoxy)P(000, H(C.--Slalkoxy)P(0)0, C.-C15-alkyl-B(CO)O, benzyloxy group, phenoxy group, phenylthio group, phenylsulfinyl or phenylsulfonyl , while the phenyl group can in turn be substituted C.-Slalalkyl, C.i-Ci-haloalkyl, C.--Slalkyoxy group, C.-Silhaloalukoxy group, /C.i-C;alkylcarbonyl, C.-C.lalkoxycarbonyl, C.-Clalkylamino group, di(C4i-Clalkyl)amino group, C.i-Salkylthio group, 7/0. C1-Slalkylsulfinyl, /C1-Slalkylsulfonyl, C.i-Sulalkyl-Z(0)2O0 group, / C.i-Suhaloalkylthio group, C.1-C.haloalkylsulfinyl, C.-Chaloalkylsulfonyl, group C1-Chaloalkyl-5(0)20, group C.i-Slalkyl-(O)2MH, C--Slalkyl-5(0)2M(C.1-Sualalkyl), a halogen, a nitro group, or a cyano group, and Co and Co" each independently of the other means hydrogen or C. - Sualalkyl, or the 02 Ka group (5) in which Koz means a hydroxy group, OM' (where M' is an alkali metal ion), a halogen, a C.4-C.ioalkyl group, C.-C.oalkylcarbonyloxy group, C.-C.alkenylcarbonyloxy group, C3-Secycloalkylcarbonyloxy group, C.-Si2alkylcarbonyloxy group, C.-Si2alkylcarbonyloxy group, CoaKovM-C(O0, C.-Sioalkylthio group, Ga. C1-C12alkylsulfinyl, C.-Si2alkylsulfonyl, C.1-C/haloalkylthio group, C.1-C/haloalkylsulfinyl, C.1-C.haloalkylsulfonyl, Co-Ci2alkenylthio group, Co-Ci5-alkenylsulfinyl, Co-Ci2alkenylsulfonyl, and) Co-C.ohaloalkenylthio group, Co-Ciohaloalkenylsulfinyl, Co-C45-haloalkenylsulfonyl, Co-C.-»alkynylthio group, Co- Si2alkynylsulfinyl, Co-Sioalkynylsulfonyl, C.--C;alkyl-Z(0)2O, phenyl-5(0)20, (C1-Sualkoxy)»P(FOO, C.-Slalkyl(Ci-Slalkoxy)P(00, H(C.i-Slalkoxy)P(0)0, C.4-C42-alkyl-(CO)O, benzyloxy group, phenoxy group, "o phenylthio group, phenylsulfinyl or phenylsulfonyl, while the phenyl group may in turn be substituted C.-Slalkyl, C.i-Slhaloalkyl, C.--Slalkoxy group, C.-Slhaloalukoxy group, /C.i-C;alkylcarbonyl, and C.-C.lalkoxycarbonyl, C.-Clalkylamino group, di(C4i-Clalkyl)amino group, C.i-Salkylthio group, C.i-C.alkylsulfinyl, C4-C;alkylsulfonyl, C.i-Sualkyl-Z(0)2O0 group, / C.i-Suhaloalkylthio group, C.1-C.haloalkylsulfinyl, C.-Chaloalkylsulfonyl, group C1-Chaloalkyl-5(0)20, group M C1-Clalkyl-5(0)2MH, C4-Clalkyl-5(0)2M (C.-Sulalkyl ), a halogen, a nitro group or a cyano group, - Coa and Cob each independently of each other means hydrogen or C.-Sualalkyl and U means oxygen, sulfur, a chemical bond or a C.-C; alkylene bridge, or a group Oz No (Oz ) "well - so am I;" ud o shov -i in which 1» Kal, Ka, Kzv and Kzo each independently of each other means hydrogen, C-Svalkyl, C.4-Svhaloalkyl, Co-Svalkenyl, Co-Svalkynyl, S.i-Svalkoxycarbonyl, S. - Svalkylthio group, C.i-Svalkylsulfinyl, 1 C-Svalkylsulfonyl, C.i-Svalkyl-MNOZ(O), C.i-Svalkylamino group, di(Ci-Svalkyl)amino group, hydroxy group, b 50 C1-Svalkoxy group, C3- Svalkenyloxy group, C3z-Svalkynyloxy group, hydroxy-C.4-Svalkyl, C.-C.alkylsulfonyloxy-C/-Salkyl, tosyloxy-C.i-Salkyl, halogen, cyano group, nitro group, phenyl or phenyl, 42) substituted by C.i-Slalkyl, C.i-Suhaloalkyl, C.-Slalkoxy group, C.i-Shaloalkyloxy group, C.-Slalkylcarbonyl, C.-C. alkoxycarbonyl, amino group, C1-Salkylamino group, di(Ci-Slalkyl)uamino group, C.--Salkylthio group, C.--Salkylsulfinyl, C.i-Salkylsulfonyl, C1-Slalkyl-5 group (02)0, C.1-Swhaloalkylthio group, C.-Swhaloalkylsulfinyl, C.-Swhaloalkylsulfonyl, o C.i-Swhaloalkyl-Z(0)20 group, C.-Slalkyl-5(0)2MH group, C.-Swalkylthio -(C.4-Sulalkyl), C-Salkylsulfinyl-M(C 4-Slalkyl), C-Salkylsulfonyl-M(C .-Slalkyl), halogen, nitro group, ime group) COOH or cyano group, or adjacent substituents Kda and K37 or Kzv and Kzo together represent C3-Svalkylene, M means oxygen, sulfur, sulfinyl, sulfonyl, -SKu4Kld»-, -С(0)- or -MEdz-, 60 Ki means hydrogen, S.--Slalkyl, Ci-C/haloalkyl, C.i-C, alkoxy-Ci-C; alkyl, C.i-C; alkylthio-C--C; alkyl, C.-C.alkylcarbonyloxy-C 1-C 1 -C 1 alkyl, C 1-C 1 alkylsulfonyloxy-C -C 6 alkyl, tosyloxy-C 1 -C 1-C alkyl, di(C 4-C 1 -C 1 -C 1 -C 1 -C 1 -C 1 -C 1 -C 1 -C 1 -C 1 -C 1 -C 1 alkyl)methyl, di(C 1 -C 1 -C 1 -C 1 -C alkylthioalkyl)methyl, ( C4-Salkoxyalkyl)-(C4-Csalkylthiosalkyl)methyl, C3-Svoxacycloalkyl, C3-Sthiacycloalkyl, C3-C.dioxacycloalkyl, C3-C/dithiacycloalkyl, C3-Sloxathiacycloalkyl, formyl, C--C, alkoxycarbonyl or phenyl, which may be in turn, substituted by 65 C-Slalkyl, C1-C1-haloalkyl, C1-Slalkoxy group, C1-C1haloalkyl group, /C1-C6 alkylcarbonyl, C.-C.alkoxycarbonyl, amino group, C.-C.alkylamino group, di(C1-Sulalkyl)amino group, C.i-Salkylthio group, C.-Salkylsulfinyl, C1-Salkylsulfonyl, C.-Salkyl-5(0)20 group, C.1-Chaloalkylthio group, C.-C.haloalkylsulfinyl, C.-Chaloalkylsulfonyl, C1-Chaloalkyl-3(0)20 group, C.-Slalkyl-5(0)2MH group, C.-Salkylthio-(C.4 -Su;alkyl), C-Salkylsulfinyl-M(C 4-Slalkyl), C-Salkylsulfonyl-M(C .-Slalkyl), halogen, nitro group, COOH group or cyano group, or Ku» together with Kzo represents S.- Svalkylene, Ka" means hydrogen, C41-Su;alkyl or C.-Su/haloalkyl, Klao means a hydroxy group, OM' (where M' is an alkali metal ion), halogen, C.4-C.ioalkyl group, C.-C.oalkylcarbonyloxy group, C.-C.alkenylcarbonyloxy group, C3-Secycloalkylcarbonyloxy group, 70. C1-Ci2-Alkoxycarbonyloxy group, C.-Ci2-Alkylcarbonyloxy group, KovKo7 M-C(O)O, C.-Sioalkylthio group, C.1-C/2alkylsulfinyl, C.-Ci2alkylsulfonyl, C.1-C/haloalkylthio group, C.1-C/haloalkylsulfinyl, C.1-C.haloalkylsulfonyl, Co-Ci2alkenylthio group, Co-Ci2alkenylsulfinyl, Co-Ci2alkenylsulfonyl, Co-Ciohaloalkenylthio group, Co-C1ohaloalkenylsulfinyl, Co-C1ohaloalkenylsulfonyl, Co-C.2oalkynylthio group, Co-Ci2alkynylsulfinyl, Co-Ci0, Cioalkynyl-sulfonyl C;alkyl-Z(O)2O, phenyl-5(O)2O, (C1-Su-Alkoxy)»P(FOO, 75. C-Slalkyl(C1-Salkoxy)P(00, H(C.--Slalkoxy)P(0)0, C.-C15-alkyl-B(CO)O, benzyloxy group, phenoxy group, phenylthio group, phenylsulfinyl or phenylsulfonyl , while the phenyl group can in turn be substituted C.-Slalalkyl, C.i-Ci-haloalkyl, C.--Slalkyoxy group, C.-Silhaloalukoxy group, /C.i-C;alkylcarbonyl, C.-C.lalkoxycarbonyl, C.-Clalkylamino group, di(C4i-Clalkyl)amino group, C.i-Salkylthio group, C-Clalkylsulfinyl, /C4-Clalkylsulfonyl, group C.i-Clalkyl-5(0)2O0, /C .-subhaloalkylthio group, C.i-C/haloalkylsulfinyl, C.-Chaloalkylsulfonyl, C1-Chaloalkyl-5(0)20 group, group S.i-Slalkyl-B(O)2MH, C--Slalkyl-5(0)2M(C1-Sualkylom), halogen, nitro group or cyano group, Kov and Ko7 each independently of each other means hydrogen or S.-Sualkyl and C is hydrogen, C-Slalkyl, C-Slalkoxycarbonyl, or phenyl, which may in turn be substituted C.-Clalkyl, C.i-Ci-haloalkyl, C.--Clialkyloxy group, C.-Clihaloalkyloxy group, /C.i-C;alkylcarbonyl, c C.i-C/Alkoxycarbonyl, C.-Salkylamino group, di(C4i-Slalkyl)amino group, C.i-Salkylthio group, o C.i-C.alkylsulfinyl, C4-C;alkylsulfonyl, C.i-Sualkyl-Z(0)2O0 group, / C.i-Suhaloalkylthio group, C.1-C.haloalkylsulfinyl, C.-Chaloalkylsulfonyl, group C1-Chaloalkyl-5(0)20, group S.i-Slalkyl-B(O)2MH, C--Slalkyl-5(0)2M(C1-Salalkyl), a halogen, a nitro group or a cyano group, or an O group that z0 RU "O) (Co) Ed ochi t | in. Pv in which YKzo means a hydroxy group, OM' (where M' is an alkali metal ion), a halogen, a C.1-C.ioalkyloxy group, a C.-C.oalkylcarbonyloxy group, a C.-C.alkenylcarbonyloxy group, a C.3-Seccycloalkylcarbonyloxy group, with C.-Ci2alkylcarbonyloxy group, C.-Ci2alkylcarbonyloxy group, Kz341К324М-Щ(ФОО, C.-CiOalkylthio group, C.1-C/2alkylsulfinyl, C.-Ci2alkylsulfonyl, C.1-C/haloalkylthio group, C.1-C/haloalkylsulfinyl, ; C.1-C.haloalkylsulfonyl, Co-Ci2alkenylthio group, Co-Ci2alkenylsulfinyl, Co-Ci2alkenylsulfonyl, Co-Ciohaloalkenylthio group, Co-C1ohaloalkenylsulfinyl, Co-C1ohaloalkenylsulfonyl, Co-C.2oalkynylthio group, Co-Ci2alkynylsulfinyl, Co-Ci0alkynyl-one -C;alkyl-Z(O)2O, phenyl-5(O)2O, (C1-Su-Alkoxy)»P(FOO, - C.i-Slalkyl(C1-Salkoxy)P(000, H(C.--Slalkoxy)P(0)0, C.-C15-alkyl-B(CO)O, benzyloxy group, phenoxy group, phenylthio group, phenylsulfinyl or phenylsulfonyl, while the phenyl group can in turn be substituted - C1-C1-alkyl, C1-C1-haloalkyl, C1-C1-C1-haloalkyl, C1-C1-haloalkyl, C1-C1-Sulalkylcarbonyl, with C.-C.alkoxycarbonyl, C.i-C.alkylamino group, di(C1-Sulalkyl)amino group, C.i-Salkylthio group, C.i-C.alkylsulfinyl, C4-C;alkylsulfonyl, group C.i-Sualkyl-Z(0)2O0, / C.i-Subhaloalkylthio group, b» C.1-C.haloalkylsulfinyl, C.-Shaloalkylsulfonyl, group C1-Shaloalkyl-5(0)20, group Ф C.i-Slalkyl-B(O)2MH, C--Slalkyl-5(0)2M(C1-Sualalkyl), halogen, nitro group or cyano group, Kz and Kz" each independently of each other means hydrogen or C.- Sualkyl, Kz3z3 and K3z4 each independently of each other means hydrogen, hydroxy group, C--Slalkyl, Co-Svalkenyl, Co-Svalkynyl, C.-C.Alkoxycarbonyl, C.-Svalkylthio group, C.-Svalkylsulfinyl, C.-Svalkylsulfonyl, Ci-Slalkyl-MNOZ(O)", Ci-Suhaloalkyl, -MH-Ci-Sulfalkyl, -M(S.i-Sulfalkyl)", C--Sulfoxy group, cyano group, (F) nitro group, halogen or phenyl, which can to be substituted in turn by C 4-Slalkyl, C.--C/haloalkyl, GI by C.-Slalkoxy group, C.-C/haloalkyl group, C.--C;alkylcarbonyl, C-Slalkoxycarbonyl, amino group, C.i-C.alkylamino group, di(Ci-Sulalkyl)amino group, C.i-Salkylthio group, C.-Salkylsulfinyl, in Si1-Salkylsulfonyl, group C.i-C;alkyl-Z(0)2O, C.- Subhaloalkylthio group, C.i-C/haloalkylsulfinyl, C1-Subhaloalkylsulfonyl, C1-Subhaloalkyl-5(0)20 group, C1-Slalkyl-5(0)2MH group, C.-Slalkyl-B(0)2M(C1-Slalkyl), halogen, nitro group, COOH group or cyano group, or K3zz and Kz4 together form a Co-Slalkylene bridge, and Kz5 is hydrogen, C.-Slalkyl, C-Slalkoxycarbonyl or phenyl, which can in turn be substituted by 65 C1-C1 alkyl, C1-C1-haloalkyl, C1-C1-C1-C1-C1-C1-C1-C1-C1-C1-C1-C1-C1-C1-C1-C1-C1-C1-C1-C1-C1-C1-C1-C1-C1-C1-C1-C1-C1-C1-C1-C1-C1-C1-C1-C1-C1-C1-C1-C1-C1-C1-C1, C1-C1-C1-C1-C1-C1-C1-C1-C1-C1-C1. C.-C.alkoxycarbonyl, amino group, C.-C.alkylamino group, di(C1-Sulalkyl)amino group, C.i-Salkylthio group, C.-Salkylsulfinyl, C1-Salkylsulfonyl, C.-Salkyl-5(0)20 group, C.1-Chaloalkylthio group, C.-C.haloalkylsulfinyl, C.-Chaloalkylsulfonyl, C1-Chaloalkyl-5(0)20 group, C4-Slalkyl-3(0)2MH group, C4-Slalkyl-5(0)2M( C1-Sulkyl), a halogen, a nitro group, a COOH group or a cyano group, or a group OB 2-Coy (Ov), in which 7 means sulfur, BO or 50", Coy means hydrogen, Si-Sdalkyl or Si-Swalkyl , substituted by a halogen, C-C; alkoxy group, C.i-Salkylthio group, C.i-Salkylsulfonyl, C.-Salkylsulfinyl, hydroxy group, cyano group, nitro group, -CHO group, -СО2Ко group, -СОКоз group, -СО5КОі group, -МКоБКов group; by the SOMCOoseCos group or phenyl, which can in turn be substituted by C -Slalkyl, C.4-Shaloalkyl, C1-Sdlkoxy group, C1-C/lhaloalkoxy group, C0-Svalkenyl, C3-Svalkynyl, C3-Svalkenyloxy group, C3-Svalkynyloxy group, halogen , nitro group, cyano group, -COOH group, COOS.1-C.alkyl, COOphenyl, C.i-Salkoxy group, phenoxy group, (C41-Slalkoxy)-C.--Slalkyl, (C4-Salalkylthio)-C4-C; alkyl, (C4-C.alkylsulfinyl)-C 4-Slalkyl, (C41-Slalkylsulfonyl) -C 4-C/alkyl, МНЗО»-С1-С;alkyl, МНБЗО»-phenyl, M(С1-Svalkyl)5О2-С14-Slalkyl, M(С4-Svalkyl)5O»-phenyl, M(С-Svalkenyl )305-C.-Sulfalkyl, M(Co-Sulfenyl)5O"-phenyl, M(C3-Sulfenyl)3O5-C.4-Su;alkyl, M(C3-Sulfenyl)5O"-phenyl, M(C3- Ccycloalkyl)ZO2-C.4-C;alkyl, M(C3-Ccycloalkyl)ZO»-phenyl, sc M(phenyl)5O025-C.4-Sulalkyl, M(phenyl)5O»-phenyl, OoBO-C.1 - Sualalkyl, SOMKO25KOz2v group, Oo5O-Ci-Suhaloalkyl, O5O»-phenyl, C.i-C; alkylthio group, C.i-Suhaloalkylthio group, phenylthio group, o C-Alkylsulfonyl, C.1-C/haloalkylsulfonyl, phenylsulfonyl, C1- Salkylsulfinyl, C-C/lhaloalkylsulfinyl, phenylsulfinyl, C-C;alkylenephenyl or the group -MCoi15C2O5Co27, or Co means Co-Svalkenyl or Co-Svalkenyl substituted with a halogen, C-Slalkoxy group, "co C.i-C.alkylthio group, C.--Slalkylsulfonyl, C.i-C;alkylsulfinyl, -SOMKOoz32Cozz group, Ccyano group, nitro group, -CHO group, -СО2Sozv group, -СОКОzo group, -СО5-C.-Slalkyl , the group -MkozaBozv or phenyl, which can in turn be substituted by C 4-C;alkyl, C--C-Shaloalkyl, C--C;alkyloxy group, C1-Chaloalkyloxy group, Co-Svalkenyl, C3-Svalkynyl, C3-Svalkenyloxy group , C3-Salkynyloxy group, halogen, nitro group, cyano group, -COOH group, COOS.-Slalkyl, COOphenyl, C.--Slalkoxy group, « phenoxy group, (C1-Slalkoxy)-C--Sulalkyl, (C4-Slalkylthio)-C1- Clalky, ich- (C4-C.alkylsulfinyl)-C 4-Clalkyl, (C41-Clalkylsulfonyl)-C 4-C/alkyl, MNZO»-C1-C; alkyl, MNZO»-phenyl, M(C4-Svalkyl) 5O»-C.4-Sulfalkyl, M(C1-Svalkyl)5O»-phenyl, M(C-Svalkenyl)305-S.-Sulfalkyl, M(Co-Svalkenyl)5O»-phenyl, M(C3-Svalkynyl) 3O5-C.4-C;alkyl, M(C3-Svalkynyl)5O"-phenyl, M(C3-Ccycloalkyl)ZO2-C.4-C;alkyl, M(C3-Ccycloalkyl)ZO"-phenyl, " 20 M(phenyl)5O025-C.4-Sulalkyl, M(phenyl )5O»-phenyl, OoBO-C.1-Sulfalkyl, SOMColoKol group, that with Oo5O-Ci-Sulfaloalkyl, O5O»-phenyl, C.i-C;alkylthio group, C.i-Sulfaloalkylthio group, phenylthio group, C-Salkylsulfonyl, C.1-C/haloalkylsulfonyl, phenylsulfonyl, C1-Alkylsulfinyl, C.-C/lhaloalkylsulfinyl, phenylsulfinyl, C-C;alkylenephenyl or the group -MKol«3ССО»Cod»o, or Koi means C3-Salkynyl or C3 - Svalkinyl, substituted by halogen, C--C/haloalkyl, cyano group, group 415 -b025Kol14 or phenyl, which in turn can be substituted by C 4-Slalkyl, C.i.-C.haloalkyl, - C.i.-C. alkoxy group, C.i - Cohaloalkyloxy group, Co-Svalkenyl, C3-Svalkynyl, C3-Svalkenyloxy group, C3-Svalkynyloxy group, halogen, nitro group, cyano group, -COOH group, СООС.1-C.alkyl, COOphenyl, - Si-Slalkoxy group, phenoxy group, )-C1-Slalkyl, (C4-Slalkylthio)-C1-Slalkyl, c (C4-C.alkylsulfinyl)-C 4-Slalkyl, (C41-Slalkylsulfonyl)-C 4-C/alkyl, МНЗО»-С1-С; alkyl, MNZO"-phenyl, M(C4-Salkyl)5O"-C.4-Sulalkyl scrap, M(C1-Svalkyl)5O"-phenyl, (2) M(C-Svalkenyl)305-S.-Sualkyl, M(Co-Svalkenyl)5O"-phenyl, M(C3-Svalkynyl)3O5-C. 4-C alkyl, F M(C3-Svalkynyl)5O»-phenyl, M(C3-Ccycloalkyl)ZO2-C.4-C;alkyl, M(C3-Ccycloalkyl)ZO»-phenyl, M(phenyl)5O25 -C.4-Sulalkyl, M(phenyl)5O»-phenyl, OoBO-C.1-Sulalkyl, SOMCOogvCogo group, Oo5O-Ci-Suhaloalkyl, O5O»-phenyl, C.i-C; alkylthio group, C.i- Subhaloalkylthio group, phenylthio group, C1-Alkylsulfonyl, C.1-C/haloalkylsulfonyl, phenylsulfonyl, C1-Alkylsulfinyl, C.-C.haloalkylsulfinyl, phenylsulfinyl, C.-C.alkylenephenyl or the group -Mkoz1CO»Cozo, or (F. Koi means C3-C6cycloalkyl or C3-C7cycloalkyl substituted by C--Clalkyl, C-Clalkoxy group, GI C-Clalkylthio group, C1-C6alkylsulfinyl, C--Clalkylsulfonyl or phenyl, which may be in turn substituted by a halogen, a nitro group, a cyano group, a C-Slalkoxy group, a C-Slalkyloxy group, a C-Slalkylthio group, a C-Salloalkylthio group, a C--C;alkyl or a C-C/uhaloalkyl, or means C1-Salkylene-C3-Scycloalkyl, phenyl or phenyl substituted with C1-Sulalkyl, C1-S8haloalkyl, C1-C1-Alkoxy, C1-Shalo-Alkoxy, C0-Swallowkenyl, C3-Swallowkynyl, C3-Swallowkenyloxy, C3- Sulkynyloxy group, halogen, nitro group, cyano group, group -"COOH, COOS.-Slalkyl, COOphenyl, C-C-Alkoxy group, phenoxy group, /(C4-Slalkoxy)-C-Slalkyl, (C-4-C; alkylthio)-C. -Slalkyl, /(C4- 65 Slalkylsulfinyl)-C4-Slalkyl, (C4-Slalkylsulfonyl)-C1-Slalkyl, and MNZO»-C1-Slalkyl, MNZO»-phenyl, M(C.4-Svalkyl)3O2-C.-Sualalkyl, M(C1-Svalkyl)5O»-phenyl, M(C»-Svalkenyl)5O5-C4-C; alkyl, M(C»-Svalkenyl)ZO»-phenyl, M(C3-Svalkynyl)3O2-C.4-C;alkyl, M(C3-Svalkynyl)ZO»-phenyl, M(C3-Ccycloalkyl)5O5-C14-Salkyl . »-phenyl, C.i-Salkylthio group, C.-C.haloalkylthio group, phenylthio group, C.-Slalkylsulfonyl, C.1-C.haloalkylsulfonyl, phenylsulfonyl, C.-C.-alkylsulfinyl, C.-C.haloalkylsulfinyl, phenylsulfinyl or the group -МКол8СО»од, or Koi means C.-C.alkylenephenyl, СОКО7 or 4-6-- linoleic heterocyclyl, Co», Cozv, Col4 and Covv each independently of the other means hydrogen, C.4-C.alkyl, phenyl or phenyl, /o substituted with C.1-C.alkyl, C.-C.haloalkyl, C.-C.alkyl , C.-Suhaloalkyloxy group, Co-Svalkenyl, C3-Svalkynyl, C3-Svalkenyloxy group, C3-Svalkynyloxy group, halogen, nitro group, cyano group, -СОоон, СООС1-С, alkyl, COOphenyl, C.i-C; alkoxy group, phenoxy group, (C-4-C;Alkoxy)-C.i-C;Alkyl, (C4-Salkylthio)-C4-C;Alkyl, (C4-C.Alkylsulfinyl)-C 4-Slalkyl, (C41-C.Alkylsulfonyl) -C 1-C;alkyl, MNZO»-C1-Sulalkyl, MNBZO»-phenyl, M(C4-Salkyl)3O»-C1-Salalkyl, M(C4-Salkyl)5O»-phenyl, 75. MSH(C2-Svalkenyl)5O2-C4-Sulfalkyl, M(Co-Svalkenyl)5O"-phenyl, M(Sz-Svalkynyl)3O5-C.4-Su;alkyl, M(S3-Svalkynyl)5O"- phenyl, M(C3-Ccycloalkyl)ZO2-C.4-C; alkyl, M(C3-Ccycloalkyl)ZO"-phenyl, M(phenyl)5O25-C.4-Sulalkyl, M(phenyl)5O"-phenyl, OoBO-S.1-Sualkilom, SOMKoloKovo group; Oo5O-Ci-Suhaloalkyl, O5O»-phenyl, C.i-C;alkylthio group, C.i-Sugaloalkylthio group, phenylthio group, C.1-C/haloalkylsulfonyl, C.1-C/haloalkylsulfonyl, phenylsulfonyl, C1-Cialkylsulfinyl, C1-C1haloalkylsulfinyl, phenylsulfinyl , C1-Slalkylphenyl or the group -MKov2СО2orvz, Koz, Kozo and Kovu each independently means C1-C6 alkyl, phenyl or phenyl substituted with C1-S11alkyl, C1-C1-C1-haloalkyl, C1-Sulalkyl, C1-C1-Alkoxy , Co-Svalkenyl, C3-Svalkynyl, C3-Svalkenyloxy group, C3-Svalkynyloxy group, halogen, nitro group, cyano group, -СОоон group, СООС1-С,alkyl, СООphenyl, С.и-С;alkoxy group, phenoxy group, (C-4- C;Alkoxy)-C.i-C;Alkyl, sc dv (C1-C.alkylthio)-C4-Clialkyl, (C4-C.alkylsulfinyl)-C 4-Clialkyl, (C41-C.alkylsulfonyl)-C 1-C ; alkyl, MNZO"-C.-Sulalkyl, MNZO"-phenyl, M(C1-Svalkyl)5O025-C.4-Slalkyl, M(C1-Svalkyl)5O"-phenyl, and) M(C"-Svalkenyl) 5O25-C14-Cu-alkyl, M(C»-Svalkenyl)5O»-phenyl, M(C3-Svalkynyl)u5O»-C1-C; alkyl, M(C3-Sval quinyl)5O»-phenyl, M(C3-Ccycloalkyl)ZO2-C.4-C;alkyl, M(C3-Ccycloalkyl)ZO»-phenyl, M(phenyl)5O025-C.4-Sulalkyl, M(phenyl) 5O"-phenyl, OOBO-C.1-Suhalalkyl, SOMKOovvKovi group "o zo О5O2-C1-C1-Alhaloalkyl, О5O"-phenyl, C.-Sulalkylthio group, C.i-Sulhaloalkylthio group, phenylthio group, C-Salalkylsulfonyl, C1-Sulhaloalkylsulfonyl, phenylsulfonyl, C1-Slalkylsulfinyl, ise) C.i-C/lhaloalkylsulfinyl, phenylsulfinyl, -"CH0)-phenyl, where Y has a value from 1 to 6, or by the group y -MKoveSO» Kovv, Kol means C.-Sulalkyl, - Cob means hydrogen, Si-Slalkyl, Co-Svalkenyl, C3-Svalkynyl, C3--Ccycloalkyl, phenyl or phenyl substituted with C.i-C;alkyl, C.-Svhaloalkyl, C.i-Salkoxy group, C.i-Shaloalkoxy group, Co-Svalkenyl, C3-Svalkynyl, C3-Svalkenyloxy group, C3-Svalkynyloxy group, halogen, nitro group, cyano group, -СОоon group . C4-C.alkylsulfinyl)-C 4-Slalkyl, (C41-C.alkylsulfonyl)-C 1-C;alkyl, " МНЗО2-С1-Сулalkyl, МНЗО"-phenyl, M(С1-Свълкіл)5О025-С.4 - Slalkyl, M(C-Svalkyl)ZO»o-phenyl, st») with M(C-Svalkenyl)305-S.-Sualkyl, M(C»-Svalkenyl)ZO»-phenyl, group M(C3-Svalkenyl) )ZO2H, . M(C3-Svalkynyl)5O»5-C14-Sualkyl, M(C3-Svalkynyl)u3O»-phenyl, the group M(C3-Sucycloalkyl)ZO2H, and M(C3-Ccycloalkyl)5O5-C14-Sualalkyl, M(C3 -Ccycloalkyl)ZO"-phenyl, M(phenyl)5O5-C4-C; alkyl, M(phenyl)5O"o-phenyl, and O505-C4-Slalkyl, the SOMKovKovv group, O505-C4-Clhaloalkyl, O5O"-phenyl , 45. C1-Salkylthio group, C.-C.haloalkylthio group, phenylthio group, C.-Salkylsulfonyl, -I C.1-C.haloalkylsulfonyl, phenylsulfonyl, C1-Salkylsulfinyl, C.-Slhaloalkylsulfinyl, phenylsulfinyl, C1-Slalkylenephenyl or -MKovoSO group "Kovo, o Kov means hydrogen, C1-C1 alkyl, C1-C6 alkyl, C3-C6 alkyl, C3-C cycloalkyl, phenyl or phenyl substituted with C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 hydroxy group, C.i-Shaloalkyloxy group, Co-Svalkenyl, C3-Svalkynyl, C3-Svalkenyloxy group, C3-Svalkynyloxy group, halogen, nitro group, cyano group, group Me. -СОоон, СООС1-С, alkyl, СООphenyl, C.i-C; alkoxy group, phenoxy group, (C-4-C; alkoxy)-C.i-C; alkyl, Ф (C4-Sualkylthio)-C4-C; alkyl, (C4-C.alkylsulfinyl)-C 4-Salalkyl, (C41-C.alkylsulfonyl)-C 1-C; alkyl, MNZO»-C.-Sulalkyl, MNZO»-phenyl, M(C1-Salkyl)5O025 -C.4-Salylalkyl, M(C1-Svalkyl)5O"-phenyl, M(C-Svalkenyl)305-S.-Svalkyl, M(Co-Svalkenyl)5O"-phenyl, M(C3-Svalkynyl)3O5- C.4-C;alkyl, two M(C3-Svalkynyl/ZO»2-phenyl, M(C3-Ccycloalkyl)ZO2-C.4-C;alkyl, M(C3-Ccycloalkyl)ZO»-phenyl, M( phenyl)5O025-C.4-Sulalkyl, M(phenyl)5O"-phenyl, OoBO-C.1-Sulalkyl, SOMKOv1Kovo group, F) Oo505-C41-Slhaloalkyl, O5O"-phenyl, C-Slalalkylthio group, S.- -subhaloalkylthio group, phenylthio group, C1-Alkylsulfonyl, C.1-C/haloalkylsulfonyl, phenylsulfonyl, C1-Alkylsulfinyl, C-C/haloalkylsulfinyl, phenylsulfinyl, C-C-alkylenephenyl or the group -MKovaCO»Kovz, where Ko means phenyl, C41-C;alkyl, C--C;alkyl group or -MKovKoo, Kov and Koo each independently of each other means C.--C;alkyl, phenyl or phenyl substituted by halogen, nitro group, cyano group, C.i-C;alkyl, C.i-C;alkoxy group, C.-Subthioalkyl, group -СО2Ковв, group -СОКов7, С1 -Slalkylsulfonyl, C.i-C; alkylsulfinyl or C.-C.haloalkyl, or Kov and Koo together form a 5- or b--linked ring, which can be interrupted by oxygen, the MKovv5 group or atom 5, 65 Kot, Kozi, Codz, Col', Covo, Covv, Covo, and Covi each independently represent hydrogen, C.4-Sulfylalkyl, C.sub.3-Svalkenyl, C.3-Svalkynyl, or C.3-Ccycloalkyl, Kogv, Kogv; Kog7t; Kogv» Kogo, Kozo, Koz2» Kozz» Koza, Kozv, Kozv; Kozt" Circle; Kol1; Number 2; Kodv, Kodv, Kol» Kolo, Koko, Kovz, Kova, Kovv, Kov?, Kovv, Kovo, Kovvi, Kovo, Kovz, Kov5 and Kovv each independently of the other means hydrogen, C--C;alkyl, Co-Svalkenyl . C-Cihaloalkylthio, Ci-Cialkyl or Ci-Cihaloalkyl, and Kzv means Ci-Cialkyl, Ci-Cihaloalkyl, C3-Swhalkenyl, C3-Swhaloalkenyl, C3-Swalkynyl, C3-Swhaloalkynyl, C3 -Swcycloalkyl or C3-Swcycloalkyl, substituted by halogen, C4-C;alkyl, C-Swhaloalkyl, C3-Swalkenyl, C3-Swhaloalkenyl, C3-Swalkynyl, C3-Swhaloalkynyl, C.--C;alkoxycarbonyl, C.-Sw;alkylthio , 7/0. C1-Slalkylsulfinyl, C.-C3alkylsulfonyl, C.-Subhaloalkylthio, C.-C.haloalkylsulfinyl, C.1-C.haloalkylsulfonyl, C.-C.alkylcarbonyl, di(Ci-Sulalkyl)amino group, C.-Slalkoxy group, C.-Cihaloalkyl group, C.i-C;alkyl-Z(0)20 group, C.-Cihaloalkyl-5(O)2O group or phenyl, which can be replaced by halogen, C--Cialkyl, C- 4-C/lhaloalkyl, C3-Svalkenyl, C3-Svalkynyl, cyano group, nitro group or COOH group, or an agronomically acceptable salt of such a compound and b) a synergistically effective amount of one or more compounds selected from the group that includes the compound of formula 2.1 Ka savon ( 271). and Co" jointly represent the c group -"SNASN-SNASN-, a compound of the formula 2.2 Ge) Without c. (222) 5 tn x Y MI (Se) zo r-on s Ka o oyu in which K5z means ethyl, Code means methyl or ethyl, and Ko5 means -"CH(Me)-SNHOMe, "52CH(Me)- СНОМе, СНоОМе or СНоО-СНоСН", - a compound of the formula 2.3 i- Me 2.3), where (2.3) and M 5 and сно « Me 0 - s in which Kob means СН(Ме)-СНОМе or "55СН(Ме)- SNYOMe, z» compound of formula 2.4 Va (2.4) Vy -I Y Shsh-k e A 2 is Her Shk; Мгваонн ne y y y (o) in which K57 means chlorine, a methoxy group or a methylthio group, Kv means ethyl, and Xo means ethyl, isopropyl, -FSMuCHZ)-CH»z or tert-butyl, 4) a compound of the formula 2.5 x (2.5) With c. 0 o СХ о00вя and in which Во means ethyl or n-propyl, Кві means СОС: 1/2Са"", -СНо-СН(Ме)5-СНоСН» or their group; 60 НО and X means oxygen, М-О-СНСНУ or М-О-СНСНСНАСН-СИ, the compound of the formula 2.6 b5 Rg (2.6) o A MU she y I Z 2 A - -- a MI h Ka « y Pv 170 Pv in which Kv" means hydrogen, methoxy group or ethoxy group, Kvz means hydrogen, methyl, methoxy group or fluorine, Kva4 means COOMEe, fluorine or chlorine, Keo5 means hydrogen or methyl, U means methine, C-E or nitrogen, 7 means methine or nitrogen, and Cob means fluorine or chlorine, a compound of formula 2.7 and 2.7 where | for (2.7) take I SI in which Ke7 means hydrogen or -C(0)-5-n-octyl, a compound of formula 2.8 and (2.8), Ka Re se o SI so in which Kov means bromine or iodine, a compound formulas 2.9 about І І Ka (2.9), iv) vav ; | і- отв, ГЯ о ме in which Кво means chlorine or a nitro group, " du compound of formula 2.10 with с Bк о (2.10) h. USNE :» с МА пхо Мме -И и in which К7о means fluorine or chlorine, and К7і means -СНО-СН(СИ)-СООСНОСН» or -МН-502Ме, is a compound of the formula 2.11 1 Ме 42.11) that Ge ») - according to 42) 7 Kz moss 550 to Ф) and in which K/7" means trifluoromethyl or chlorine, where the compound of formula 2.12 o 42.12) 60 V soon Me I t a- МН; also: be in which K7z means МН" or "52МН", the compound of formula 2.13 (2.13 chat od V g 73 K) 2 ha t Z 1 t pe o, nn n in which ХУ means nitrogen, methine, МН-СНО or М-Ме, Мо means nitrogen, methine or C-Y, У3 means methine, Hu means metyn or U" and Z; jointly represent sulfur or C-CI, U 5 means nitrogen or methine, U means methyl, difluoromethoxy group, trifluoromethyl or methoxy group, 7 means methoxy group or difluoromethoxy group and K74 means СОМе», СООМe, СООС»БНБ, trifluoromethyl, СНо-СНЖСЕ»z or 5О25СН»оСН with, or its sodium salt, a compound of the formula 2.13.c i Kch Snu «2.13.c) 9 Й сн Й or M. x Kz M o g z onyaz H compound of formula 2.14 Me m-Mm o 0me(2lU d Me Ou o Me M o m-n H compound of formula 2.15 i-y ny si (2.15) s o Shchi o vy u ; their their v. compound of formula 2.16 " (2.16 noos-7 tm tРО(Он, 79 N ts compound of formula 2.17 ;» o y (gl) Che: M Me V. and i" what about the compound of the formula 2.18 b) 70 Kya (2.18) Me -07 42) -- in Me x r; I isk Mkha Me o we Me o compound of formula 2.19 SI (2.18) 60 Se on C OomMe b5 compound of formula 2.20 o 42.20) ME: e disruptions Me ie Me compound of formula 2.21 (c) (2.21) y; SI: U sk, I- M, o o Me 9 Me. o Me - ts sn. compound of formula 2.22 С (2.22) со и и Me m (Се) зо и с compound of formula 2.23 С (2.23) ю Зо -Щжх--соон - compound of formula 2.24 ЕЕ о 42.24) « du si mo || z - o o 2" in 0-4 - Y n-pentyl e compound of formula 2.25 o E (2.25) b 50 С MI i 5 5 M in meoosi o o o compound of formula 2.26 imo) c Me (2.26) CE TM 60 - fo 5 y -- o y sho b5 compound of formula 2.27 E a (2.27) o mo ; I o U i 70 not the compound of the formula 2.28 /- t , 42.28) Me --IM M-me Shdi iz seg ge: the compound of the formula 2.29 SI B (2.29) II i au MI o x / s y not o the compound of the formula 2.30 ma (2.30) со И А-М Ж нт з то С б, rea iv) compound of formula 2.31 З СИ о (2.31) и- Б) СА А С m--М g « Me - s compound of formula 2.32 "with E Ne (2.32) CE - 45.9 In M. -I I Me ikh o o i-y Me - (22) Me F compound of formula 2.33 nn o (2.33) noos-. M.Yu Gi yad II She MO Mme--8-Me on GF) Me GI compound of formula 2.34 (2.34) 50 ni volnesodn, compound of formula 2.35 b5 CE (2.35) - - x y x sna -5 -- C o compound of formula 2.36 Y (2.36) 70 sn, M -E (c) si Y " 7"sesni Z o 19 compound of formula 2.37 (2.37) St. sn.snesnU. ISH- y: so2sn. - kerosene MI SEZ compound of formula 2.38 also M sne, (2.38) sch | o ziv LU oon, sniesniesn. compound of the formula 2.39 (Ce) sn, (2.39) (Ce) (СН MI о ИС) КИ « ОО ; compound of formula 2.40 (2.40) "SI МНСОМ(СН p. 7 - с си ;" compound of formula 2.41 42.41) 45.5 osnyuO»n -I their SNU with the compound of the formula 2.42 F 50 iz 42.42) F zdsvenooya SNU the compound of the formula 2.43 (FI iz 42.43) With name) Sn rt eyuMNsnz and MA--MI 60 the compound of the formula 2.44 b5 not sni (2.44) i She II | NOSI No Osna.sn. the compound of the formula 2.45 70 o (2.45) o 8 o i PV p. i den -CH, not - «1 ih xi H Me o Men, the compound of the formula 2.46 o (2.46) Zh. o-isopropyl 720 Ne sho A U s dn SEZ Ne s 29 compound of formula 2.47 (o) o (2.4) uz snasna o - (Se) SI si o IS) o « compound of formula 2.48 sna B ro48) t o IC nene x Sai | | as s o o ;" Another dream not sh o - - o t snu o sh» compound of formula 2.49 1 E (2.45) bu 50 snu o -- II MAMAY m F y t N ny i o E 59 and F) compound of formula 2.50 t sn. o (2.50) with sn bo ve-T Ta I SN, o x- sna pl. and the compound of formula 2.51 b5 ha SNU. (2.51) E a-y ah - MA E o o-i sleep 70 0- 2. The composition according to claim 1, while in the formula K in each case independently means hydrogen, C.i.-Cylalkyl, C.sub.-Salkylenyl, C.sub.-Sylalkyl, C.sub.-Sylhaloalkenyl, C.sub.Alkynyl, C.sub.Sylhaloalkynyl, C.sub.3-Sylcycloalkyl, S.i. -Swallowoxy group, C.-Swhaloalkyl group, C-Swalkylthio group, S.i-Swalkylsulfinyl, C.--Swalkylsulfonyl, S.i-Swhaloalkyl, S.i-Swhaloalkylthio group, C.Swhaloalkylsulfinyl, C1-Swhaloalkylsulfonyl, C.-Swallowoxycarbonyl, C .-Salkylcarbonyl, C-Salkylamino group, di(C-Salkyl)damino group, S.i-Salkylaminosulfonyl, di(C--Salkyl)aminosulfonyl, -M(К4)-5-К2, -М(К3)-50-К ;, -М(К5)-5О02-Ке, nitro group, cyano group, halogen, hydroxy group, amino group, benzylthio group, benzylsulfinyl, benzylsulfonyl, phenyl, phenoxy group, phenylthio group, phenylsulfinyl or phenylsulfonyl, while the phenyl group can be mono-, di- or trisubstituted by S.-Svalkil, C.-Swhaloalkyl, C3z-Swalkenyl, C3-Swhaloalkenyl, C3-Swalkynyl, C3-Swhaloalkynyl, C-Swallowoxy group, C-Swhaloalkyloxy group, C3-Sw-alkenyloxy group, C3-Swalkynyloxy group, mercapto group, S.i-Swalkylthio group, S.- Svhaloalkylthio group, C3-Svlkenylthio group, C3-Svhaloalkenylthio group, C3-Svlkynylthio group, Co-Svlkoxyalkylthio group, C3-Cracetylalkylthio group, C3-Cv-Alkoxycarbonylalkylthio group, Co-C.cyanoalkylthio group, C1-Svlkylsulfinyl, c C.i-C.sub.haloalkylsulfinyl, C.-C.sub.alkylsulfonyl, C.-C.sub.haloalkylsulfonyl, aminosulfonyl, o C.sub.1-Soalkylaminosulfonyl, C.sub.1-C.dialkylaminosulfonyl, C.-S.alkylene-Cl5 group, MEdeCad? group, halogen, cyano group, nitro group, phenyl or benzylthio group, and the last two groups, which are phenyl Its benzylthio group, in turn, can be replaced in the phenyl ring by C--S-alkyl, C4-C-haloalkyl, C-C-C-Alkoxy group, C--C-C-C halo-Alkoxy group, halogen, cyano group or nitro group, or |se) K in each case independently means a monocyclic or condensed bicyclic ring system with 5-10 "membered, which can be aromatic or partially saturated and can contain from 1 to 4 heteroatoms selected from nitrogen, oxygen and sulfur, while such a ring system is either directly attached to the pyridine ring, MO or attached to the pyridine ring through a C 1-C; alkylene group, each ring system cannot contain " more than two oxygen atoms and cannot contain more than two sulfur atoms and the indicated ring system can be mono-, mono- or tri-substituted in C5, in turn, by C.-Salkyl, C.-Swhaloalkyl, C3-Swalkenyl, y- C3-Swhaloalkenyl, Cz - Svalkynyl, C3-Svhaloalkynyl, C.--Svalkoxy group, C.--Svhaloalkoxy group, C3-Svalkenyloxy group, C3-Svalkynyloxy group, mercapto group, C.-Svalkylthio group, C.i-Cvhaloalkylthio group, C3-Cvhaloalkylthio group, C3-Cvhaloalkenylthio group, C3-Cvlkynylthio group, Co-Cvalkyloxyalkylthio group, C3-Cvacetylalkylthio group, C3-Cvoxycarbonylalkylthio group, C.-C.cyanoalkylthio group, C.-Cvalkylsulfinyl, C.-Cvylsulfinyl, Svalkylsulfonyl, t c C-Svhaloalkylsulfonyl, aminosulfonyl, C1-Soalkylaminosulfonyl, C»-Suldialkylaminosulfonyl, h group C.--Csalkylene-K7, MKaKo group, halogen, cyano group, nitro group, phenyl or benzylthio group, » while phenyl and benzylthio group in their can alternately be substituted in the phenyl ring by S.--Szalkyl, C.-Shaloalkyl, C.-Shaloalkyl, C.-Shaloalkyl, halogen, cyano group or nitro group, while Ku, K»o, Kz, Ku, Kv, Kv, K7, Ka, Ko, Kl5, Kav and K.47 have the values specified in claim 1, and the substituents near the nitrogen atom in the heterocyclic ring are different from halogen. iz Z. The composition according to claim 1, which contains as a compound of formula I a compound of formula Ia a «Ia) a Fu 0 and a pe 4) Ka M KE in which Clv means C.i.s.alkyl, C.sylalkyl, C.sylalkyl, C.sylhaloalkenyl , Co-Cvalkyl, C3-Cvhaloalkynyl, C3-Cvcycloalkyl, C.i.Svhaloalkyl or a monocyclic or fused bicyclic ring system with 5-10 members, which may be HF) aromatic or partially saturated and may contain from 1 to 4 heteroatoms selected from nitrogen, oxygen and sulfur, 7 and such a ring system or directly attached to the pyridine ring, or attached to the pyridine ring through a C.1-C; alkylene group, each ring system cannot contain more than two oxygen atoms and cannot contain more than two sulfur atoms, and the indicated ring system can in turn be mono- , di- or trisubstituted by C.i-Swalkyl, C.i-Swhaloalkyl, C3-Swalkenyl, C3-Swhaloalkenyl, C3-Swalkynyl, C3-Swhaloalkynyl, C.-Swallowoxy, C3-Swhaloalkyl, C3-Swalkenyloxy, C3-Swalkynyloxy , mercapto group, C.-Swalkylthio group, C.-Swhaloalkylthio group, C3z-Swalkenylthio group, C3-Swhaloalkenylthio group, C3-Swalkynylthio group, Co-Swallowoxyalkylthio group, C3-Swacetylalkylthio group, C3-Swallowoxycarbonylalkylthio group, Co-C.cyanoalkyl by a group, b5: N: No and and and and ; Si-Swalkylsulfinyl, S.--Swhaloalkylsulfinyl, S.--Swalkylsulfonyl, S.--Swhaloalkylsulfonyl, aminosulfonyl, C.--Soalkylaminosulfonyl, Co-C/dialkylaminosulfonyl, C.-Salkylene-K»7 group, MKaCo group, halogen, cyano group, nitro group, phenyl or benzylthio group, while phenyl and benzylthio group in turn can be substituted in phenyl rings S--Szalkyl, S.-Szgaloalkyl, by a C.sup.-Salkoxy group, C.sup.-Cshaloalkyl, a halogen, a cyano group, or a nitro group, and the substituents near the nitrogen atom in the heterocyclic ring are different from halogen, Kldo means hydrogen, C.sup.-Salkyl, S.i.sup.haloalkyl, halogen, or phenyl, which can be substituted C.-Salkyl, C.sub.3-haloalkyl, C.sub.-C.sub.alkoxy group, C.sub.-C.sub.haloalkyl group, halogen, cyano group or nitro group, 70 Keo means C.sub.-Shaloalkyl and EK", Kv, K"e and O have the values specified in claim 1. 4. The composition according to clause 3, which contains a compound of the formula Ta, in which K dv means C.sub.--Salkyl, C.sub.-Salkyl, C.sub.Swhaloalkenyl, C.sub.Swalkynyl, C.sub.3-S.sub.haloalkynyl, C.sub.3-S.sub.cycloalkyl or C.sub.1-Swhaloalkyl . 5. The composition according to claim 1, which contains a compound of formula I, in which OO means the group О» or Оз. 6. The composition according to claim 5, which contains a compound of formula I, in which in the group 0" Koz means a hydroxy group. 7. The composition according to claim 5, which contains a compound of formula I, in which in the Oz group Kdo means a hydroxy group. s schi 6) (Se) (Se) iv) " in. - with . and? -I sh» 1 (22) 42) ime) 60 b5