ZA200205748B - Herbicidal composition. - Google Patents

Description

Herbicidal composition

The present invention relates to a novel herbicidal composition comprising a herbicidal active ‘ ingredient combination that is suitable for the selective control of weeds in crops of useful plants, for example in maize crops. The invention relates also to a method of controlling weeds in crops of useful plants, and to the use of the novel composition for that purpose.

The compounds of formula 0 .

Q

(1)

N

R

R)_ wherein the definitions of the substituents are given hereinbelow have herbicidal activity.

Surprisingly, it has now been shown that a combination of variable amounts of active ingredients, that is, of an active ingredient of formula | with one or more of the active ingredients of formulae 2.1 to 2.51 listed below, which are known and some of which are also commercially available, exhibits a synergistic action that is capable of controlling, both pre-emergence and post-emergence, the majority of weeds occurring especially in crops of useful plants.

There is therefore proposed in accordance with the present invention a novel synergistic ‘composition for selective weed control that, in addition to customary inert formulation adjuvants, comprises as active ingredient a mixture of 3 a) a herbicidally effective amount of a compound of formula

0)

Q v (h,

GY m . wherein each R is independently hydrogen, C;-Csalkyl, Co-Cgalkenyl, C,-Cghaloalkenyl,

C2-Cealkynyl, C,-Cghaloalkynyl, Cs-Ceeycloalkyl, C;-Csalkoxy, C-Cghaloalkoxy, Cs-

Cealkylthio, C;-Cgalkylsulfinyl, C,-Csalkylsulfonyl, C;-Cghaloalkyl, C,-Cghaloalkylthio, C;-

Cehaloalkylsulfinyl, C:-Cshaloalkylsulfonyl, C,-Cealkoxycarbonyl, C4-Csalkylcarbonyl, C;-

Cealkylamino, di(C;-Cgalkyl)amino, C,-Cgalkylaminosulfonyl, di(C,-Cealkyl)aminosulfonyl, -

N(R1)-S-Rz, -N(R3)-SO-R,, -N(Rs)-SO.-Rs, nitro, cyano, halogen, hydroxy, amino, benzylthio, y benzylsulfinyl, benzylsulfonyl, phenyl, phenoxy, phenylthio, phenylsulfinyl or phenylsulfonyl; wherein the phenyl group may itself be mono-, di- or tri-substituted by C;-Cgalkyl, C4-Cghalo- alkyl, C;-Csalkenyl, Cs-Cghaloalkenyl, Cs-Cgalkynyl, Cs-Cshaloalkynyl, C;-Cealkoxy, C;-

Cehaloalkoxy, Cs-Cealkenyloxy, Cs-Cealkynyloxy, mercapto, C,-Csalkylthio, C;-

Cehaloalkylthio, C3-Csalkenylthio, Cs-Cshaloalkenyithio, Cs-Csalkynyithio, Co-

Csalkoxyalkylithio, Cs-Csacetylalkylthio, Cs-Cealkoxycarbonylalkylthio, C»-Cacyanoalkyithio,

C,-Cealkylsulfinyl, C;-Cghaloalkylsulfinyl, C,-Csalkylsulfonyl, C;-Cghaloalkylsulfonyl, aminosulfonyl, C,-Coalkylaminosulfonyl, C,-C,dialkylaminosulfonyl, C;-Caalkylene-Rgs,

NR4sR47, halogen, cyano, nitro, phenyl or by benzylthio, wherein the latter phenyl and benzylthio groups may themselves be substituted on the phenyl ring by C;-Csalkyl, C;-

Cshaloalkyl, C,-Csalkoxy, C4-Cshaloalkoxy, halogen, cyano or by nitro; or each R is independently a monocyclic or fused bicyclic ring system having from 5 to 10 members, which may be aromatic or partially saturated and may-contain from 1 to 4 hetero atoms selected from nitrogen, oxygen and sulfur; wherein the ring system either is bound directly to the pyridine ring or is bound to the pyridine ring via a C;-C,alkylene group, and s each ring system may not contain more than two oxygen atoms and may not contain more than two sulfur atoms, and the ring system may itself be mono-, di- or tri-substituted by . C+-Cgalkyl, C;-Cghaloalkyl, Cs-Cgalkenyl, Cy-Cohaloalkenyl, Cs-Cealkynyl, Cs-Cghaloalkynyl,

C4-Cealkoxy, Cy-Cshaloalkoxy, Cs-Cgalkenyloxy, Cs-Csalkynyloxy, mercapto, Ci-Cealkylthio,

C1-Cghaloalkylthio, Cs-Cealkenylthio, C;-Cghaloalkenylthio, Cs-Csalkynyithio, C,- -Csalkoxyalkylthio, Cs-Csacetylalkylthio, C4-Cealkoxycarbonylalkylthio, C,-Cacyanoalkylthio,

- C4-Cealkylsulfinyl, C;-Cghaloalkylsulfinyl, C,-Cealkylsulfonyl, C,-Cshaloalkylsulfonyl, ) aminosulfonyl, C,-Calkylaminosulfonyl, C,-C,dialkylaminosulfonyl, C,-Csalkylene-R,, NRgRg, halogen, cyano, nitro, phenyl or by benzyithio, wherein phenyl and benzylthio may o themselves be substituted on the phenyl ring by C;-Csalkyl, C;-Cshaloalkyl, C,-Csalkoxy, Ci-

Cshaloalkoxy, halogen, cyano or by nitro, and wherein the substituents on the nitrogen in the heterocyclic ring are other than halogen; or each R is independently C4-Cjalkoxy-C;-Cjalkyl or C4-Caalkoxy-C;-Caalkoxy-C-Caalkyl; mis 1,2, 3 or 4;

Ri, Rs and Rs are each independently of the others hydrogen or C1-Cealkyl;

Rz is NR1oR1s, C-Cgalkoxy, Cs-Cghaloalkoxy, Ci-Cealkyl, C4-Cghaloalkyl, Cs-Cealkenyl, Ca-Ce- haloalkenyl, C5-Cgalkynyl, C5-Cghaloalkynyl, Cs-Cgcycloalkyl or phenyl, wherein phenyl may itself be substituted by C,-Csalkyl, C,-Cshaloalkyl, C,-Csalkoxy, C,-Cshaloalkoxy, halogen, cyano or by nitro;

Rs is NR12R43, C4-Cealkoxy, Cs-Cghaloalkoxy, C4-Csalkyl, Ci-Cghaloalkyl, Cs-Cgalkenyl, Cs-Ce- haloalkenyl, C3-Cgalkynyl, Cs-Cghaloalkynyl, C5-Cecycloalkyl or phenyl, wherein phenyl may itself be substituted by C4-Csalkyl, C,-Cshaloalkyl, C4-Cjalkoxy, C,-Cshaloalkoxy, halogen, cyano or by nitro; :

Rs is NR14R;5, C1-Cealkoxy, C4-Cghaloalkoxy, C41-Cgalkyl, C4-Cghaloalkyl, Cs-Cgsalkenyl, Cs-Ce- haloalkenyl, Cs-Cealkynyl, Cs-Cghaloalkynyl, Cs-Cgcycloalkyl or phenyl, wherein phenyl may itself be substituted by C;-Csalkyl, C;-Cshaloalkyl, C,-Cjalkoxy, C,-Czhaloalkoxy, halogen, cyano or by nitro;

R; and Rys are each independently of the other C,-Cjalkoxy, C,-Csalkoxycarbonyl, C{-Cs- alkyithio, C,-Csalkylsulfinyl, C4-Csalkylsulfonyl or phenyl, wherein phenyl may itself be substituted by C;-Caalkyl, C;-Cshaloalkyl, C,-Csalkoxy, C,-Cshaloalkoxy, halogen, cyano or by nitro;

Rs, Rio, Ry2, R14 and Rs are each independently of the others hydrogen or C4-Cgalkyl;

Rs, R11, Ria, Ris and Ry; are each independently of the others C;-Cgalkyl or C;-Cgalkoxy;

Q is the group Q; 0] 2 Ri " “R 19 R ol v

EE ,,—.SS.—S——————————————————————————————————— wherein Rig, R47, Rig and Ryo are each independently of the others hydrogen, hydroxy, . C4-Caalkyl, C,-Cealkenyl, C,-Csalkynyl, C,-Cqalkoxycarbonyl, C,-Cealkylthio, C4-

Cealkylsulfinyl, C;-Cealkylsulfonyl, Ci-C,alkyl-NHS(O),, C;-Cshaloalkyl, -NH-C4-Cjalkyl, - . N(C4-Caalkyl),, C4-Cgalkoxy, cyano, nitro, halogen, or phenyl which may itself be substituted by C4-Caalkyl, C4-Cshaloalkyl, C4-Cjalkoxy, C4-Cshaloalkoxy, Cq-Caalkylcarbonyl, C,-

Caalkoxycarbonyl, amino, C4-Caalkylamino, di(C;-Cgalkyl)amino, C;-Cgalkylthio, C;-

Cealkylsulfinyl, C;-Csalkylsulfonyl, C;-C,alkyl-S(0),0, C;-Cshaloalkyithio, Cy-

Cshaloalkylsulfinyl, C4-Cjhaloalkylsulfonyl, C;-Cshaloalkyl-S(0),0, C4-Caalkyl-S(O),NH, C4-

C.alkyl-S(0).N(C;-Caalkyl), halogen, nitro, COOH or by cyano; or two adjacent substituents out of Rye, R47, Rig and Rg form a C,-Cgalkylene bridge;

Rao is hydroxy, O'M*, halogen, C,-Cyzalkoxy, C;-Czalkylcarbonyloxy, C.-C alkenylcarbonyl- oxy, Cs-Cecycloalkylcarbonyloxy, C+-Cyzalkoxycarbonyloxy, C;-Cizalkylcarbonyloxy,

R21R22N-C(0O)O, C;-Ci.alkylthio, C;-Cyzalkylsulfinyl, C,-Cyalkylsulfonyl, C4-Cshaloalkylthio,

C,-Cghaloalkylsulfinyl, C;-Cshaloalkylsulfonyl, Co-C4zalkenylthio, C,-Cyzalkenylsulfinyl, Ca-Cyo- alkenylsulfonyl, C,-C,zhaloalkenylthio, C»-Csohaloalkenylsulfinyl, C,-Cizhaloalkenyisuifonyl,

C2-Cyzalkynylthio, Co-Cizalkynylsulfinyl, Co-Cizalkynylsulfonyl, Cy-Caalkyl-S(0).0, phenyl-S(0)20, (C,-Caalkoxy),P(O)0O, C,-C,alkyl(C,-Caalkoxy)P(0)O, H(C;-C,alkoxy)P(0)0O,

Cs-Ci2-alkyl-S(CO)O, benzyloxy, phenoxy, phenylthio, phenylsulfinyl or phenylsulfonyl, wherein the phenyl group may itself be substituted by C4-C,alkyl, C;-Cshaloalkyl, C,-

Caalkoxy, C4-Cshaloalkoxy, C;-Caalkylcarbonyl, C,-Cjalkoxycarbonyl, C,-Cjalkylamino, di(C,-

C.alkyl)amino, C,-C.alkylthio, C,-Caalkylsulfinyl, C,-Calkylsulfonyl, C,-C,alkyl-S(0).0, C,-

C.haloalkylthio, C4-Cjhaloalkylsulfinyl, C,-Cjhaloalkylsulfonyl, C;-C;haloalkyl-S(0),0, C;-

Caalkyl-S(O).NH, C,-C,alkyl-S(O).N(C4-C,alkyl), halogen, nitro or by cyano; and

R21 and Ry; are each independently of the other hydrogen or C,-Cjalkyl; or is the group Q,

R 23

T° (Qa), 0 : wherein Rg; is hydroxy, OM’, halogen, C,-Cszalkoxy, Ci-Cyaalkylcarbonyloxy, C,-Ci- alkenylcarbonyloxy, Cs-Cgeycloalkylcarbonyloxy, C4-Cizalkoxycarbonyloxy, C-Cyzalkyl- ’ carbonyloxy, R24R2sN-C(0)O, C4-Ciaalkylthio, Ci-Cyzalkylsulfinyl, C4-Cyzalkylsulfonyl,

C,-Cshaloalkylthio, C;-Cshaloalkylsulfinyl, C,-C;haloalkylsulfonyl, C,-Cyzalkenyithio, C,-C,o- alkenylsulfinyl, C,-C4zalkenylsulfonyl, C,-Cyzhaloalkenylthio, C,-Czhaloalkenylsulfinyl, Co-C,-

haloalkenylsulfonyl, C,-Cy.alkynylthio, C,-Czalkynylsulfinyl, C,-Cy.alkynylsulfonyl, ‘ C4-Caalkyl-S(0),0, phenyl-S(0),0, (C4-C,alkoxy).P(0)0O, Cs-Caalkyl(C;-Caalkoxy)P(0)O,

H(C4-Caalkoxy)P(0)O, C;-Ci2-alkyl-S(CO)O, benzyloxy, phenoxy, phenyithio, phenyisuifinyl ° or phenylsulfonyl, wherein the phenyl group may itself be substituted by C,-Cjalkyl, Cs-

Cihaloalkyl, C,-Cjalkoxy, Ci-Cshaloalkoxy, Ci-Cialkylcarbonyl, C;-Caalkoxycarbonyi, Cs-

Caalkylamino, di(C4-Cjalkyl)amino, C4-C,alkylthio, C-Calkylsulfinyl, C,-Cjalkylsulfonyl,

C1-Caalkyl-S(0),0, C,-Cshaloalkylthio, C4-Cshaloalkylsulfinyl, C4-Cgshaloalkylsulfonyl,

C1-Cshaloalkyl-S(0),0, C;-Caalkyl-S(0).NH, C,-C,alkyl-S(0),N(C4-Caalkyl), halogen, nitro or by cyano;

R24 and Rys are each independently of the other hydrogen or C,-C,alkyl; and

Y is oxygen, sulfur, a chemical bond or a C,-C,alkylene bridge; or is the group Qs

Rio A, ~~

Xi Ror (Qa), . Rao Rag : wherein Ras, R37, Rss and Rag are each independently of the others hydrogen, C-Cealkyl,

C,-Cghaloalkyl, C,-Cgalkenyl, C,-Cgalkynyl, C;-Cgalkoxycarbonyl, C;-Cgalkylthio, C,-Csalkyl- sulfinyl, C,-Cealkylsulfonyl, C;-Csalkyl-NHS(O),, C4-Cealkylamino, di(C,-Cealkyl)amino, hydroxy, Cs-Cealkoxy, Cs-Cealkenyloxy, Cs-Cealkynyloxy, hydroxy-Ci-Cealkyl, C4-Cjalkyl- sulfonyloxy-C,-Cealkyl, tosyloxy-C;-Csalkyl, halogen, cyano, nitro, phenyl, or phenyl substituted by C4-Cjalkyl, C1-Cshaloalkyl, C4-Caalkoxy, Cs-Cjhaloalkoxy, Cy-Caalkylcarbonyl,

C,-Cialkoxycarbonyl, amino, C,-Csalkylamino, di(C4-Cjalkyl)amino, C;-Cealkylthio, C4-

Cealkylsuifinyl, C;-Cealkylsulfonyl, C4-Cjalkyl-S(0).0, C4-Cshaloalkyithio, Cq-

Cghaloalkylsulfinyl, C,-Cghaloalkylsulfonyl, C,-Cshaloalkyl-S(0),0, C,-C,alkyl-S(O).NH, C;-

Cealkylthio-N(C;-Caalkyl), Cy-Cealkylsulfinyl-N(Ci-Caalkyl), C;-Cealkylsulfonyl-N(C4-C,alkyl), halogen, nitro, COOH or by cyano; or adjacent R,4 and Rj; or Rag and Rg together are Cs-

Cealkylene;

W is oxygen, sulfur, sulfinyl, sulfonyl, -CR1R4,-, -C(O)- or -NRy3-;

Ra: is hydrogen, C1-Caalkyl, C;-C4haloalkyl, C4-Caalkoxy-C-Cjalkyl, C4-Cjalkylthio-C,-

Caalkyl, C4-Cqalkylcarbonyloxy-C,-Calkyl, Cy-Cjalkylsuifonyloxy-Cy-Calkyl, tosyloxy-C;-

Caalkyl, di(C4-Csalkoxyalkyl)methyl, di(C,-Csalkylthioalkyl)methyl, (C,-Csalkoxyalkyl)-(C,-

Csalkylthioalkyl)methyl, C;-Csoxacycloalkyl, Cs-Csthiacycloalkyl, Cs-Cadioxacycloalkyl, Cs-

Cudithiacycloalkyl, C5-C,oxathiacycloalkyl, formyl, C;-C,alkoxycarbonyl, or phenyl which may ’ itself be substituted by C,-C,alkyl, C,-Cshaloalkyl, C,-C,alkoxy, C;-Cshaloalkoxy, C;-

Caalkylcarbonyl, C;-C,alkoxycarbonyl, amino, C,-Cjalkylamino, di(C;-Caalkyl)amino, Cs-

Caalkylthio, C;-Cjalkylsulfinyl, C4-C,alkylsulfonyl, C;-Calkyl-S(0).0, C;-Cshaloalkylthio, Ci-

Cahaloalkylsulfinyl, C,-C4haloalkylsulfonyi, Cs-C,haloalkyl-S(0).0, C;-Csalkyl-S(O),NH, Cs-

Cealkylthio-N(C,-C,alkyl), Ci-Cealkylsulfinyl-N(C;-Caalkyl), C;-Cealkylsulfonyl-N(C;-Caalkyl), halogen, nitro, COOH or by cyano; or Ry, together with Ra is C;-Cealkylene;

Raz is hydrogen, C;-Cjalkyl or C4-C haloalkyl;

Rao is hydroxy, O'M*, halogen, C;-C;.alkoxy, C4-Cyqalkylcarbonyloxy, C,-Caalkenylcarbonyl- oxy, Cs-Cecycloalkylcarbonyloxy, C,-Cyoalkoxycarbonyloxy, C-Cy.alkylcarbonyloxy,

ResRe7N-C(O)O, C4-Calkylthio, C,-Ciqalkylsulfinyl, C4-Cizalkylsulfonyl, C;-C,haloalkylthio,

C,-Cahaloalkylsulfinyl, C4-Cshaloalkylsulfonyl, C,-Cyzalkenylthio, Co-Ci.alkenylsulfinyl, Co-Cop- alkenylsulfonyl, C»-Cszhaloalkenylthio, C,-Cyzhaloalkenylsulfinyl, C»-Cyzhaloalkenylsulfonyi,

Co-Cyealkynylthio, C,-Cyzalkynylsulfinyl, Co-Cyzalkynylsulfonyl, C,-C,alkyl-S(0),0, phenyl-S(0):0, (C,-Caalkoxy).P(0)O, C;-Calkyl(C,-C,alkoxy)P(O)O, H(C4-C,alkoxy)P(0O)O,

C1-Cy2-alkyl-S(CO)O, benzyloxy, phenoxy, phenylthio, phenylsulfinyl or phenylsulfonyl, wherein the phenyl group may itself be substituted by C,-C,alkyl, C;-C haloalkyl, C;-

Caalkoxy, C4-Cshaloalkoxy, Cq-Caalkylcarbonyl, C,-Cgalkoxycarbonyl, C4-Cjalkylamino, di(C;-

Caalkyl)amino, C;-Cjalkylthio, C;-Caalkylsulfinyl, Cy-C,alkylsulfonyl, C;-Caalkyl-S(O);0, C;-

Cghaloalkylthio, C,-C,haloalkylsulfinyl, C,-Cshaloalkylsulfonyl, C,-Cshaloalkyl-S(0).0, C;-

Caalkyl-S(0)2NH, C,-C,alkyl-S(0),N(C,-C,alkyl), halogen, nitro or by cyano;

Res and Ry are each independently of the other hydrogen or C,-C,alkyl;

Ras is hydrogen, C,-Caalkyl, Cy-C,alkoxycarbonyl, or phenyl which may itself be substituted by Cs-Caalkyl, C4-Cshaloalkyl, C4-C,alkoxy, Ci-Cjhaloalkoxy, C4-Caalkylcarbonyl, Cs-

Caalkoxycarbonyl, C;-Cjalkylamino, di(C,-C,alkyl)amino, C,-Cjalkyithio, C,-Cjalkylsulfinyl,

Cy-Caalkylsulfonyl, C4-Csalkyl-S(0).0, C;-Cghaloalkylthio, Cy-C,haloalkylsulfinyi, C,-

Cshaloalkylsulfonyl, C4-Cshaloalkyl-S(0),0, C;-Caalkyl-S(O),NH, C,-Cjalkyl-S(O),N(C;-

Caalkyl), halogen, nitro or by cyano; or is the group Qu

R 30 R us 4 i TY Ra (Qu), oy

R

! wherein Rg, hydroxy, O'M*, halogen, C;-Cyzalkoxy, Cy-Cizalkylcarbonyloxy, Cx-Cialkenyl- ‘ carbonyloxy, Cs-Cecycloalkylcarbonyloxy, C;-Cizalkoxycarbonyloxy, Cs-Cyzalkylcarbonyloxy,

R31R3N-C(0)0, C,-Cyalkylthio, C;-Cyalkylsulfinyl, C4-Cyzalkylsulfonyl, C4-Cshaloalkylthio, - C,-Cyhaloalkylsulfinyl, C4-Cshaloalkylsulfonyl, C,-Cizalkenylthio, Co-Cyzalkenylsulfinyl, Co-Cio- alkenylsulfonyl, C,-C4zhaloalkenylthio, C,-Cizhaloalkenylsulfinyl, C»-Cyzhaloalkenylsulfonyl,

Ca-Cyzalkynylthio, Co-Cyzalkynylsulfinyl, Co-Cyaalkynylsulfonyl, C;-C,alkyl-S(0).0, phenyl-S(0).0, (C,-Caalkoxy),P(0)O, C;-Cjalkyl(C;-Cialkoxy)P(0)O, H(C,-Cjalkoxy)P(O)O,

C;-Ci2-alkyl-S(CO)O, benzyloxy, phenoxy, phenyithio, phenylsuifinyl or phenylsulfonyl, wherein the phenyl group may itself be substituted by C,-Cjalkyl, C;-C4haloalkyl, C4-

Caalkoxy, C,-C4haloalkoxy, Cy-Caalkylcarbonyl, C,-Cgalkoxycarbonyl, C4-Csalkylamino, di(Cs-

Caalkylyamino, C,;-Cjalkylthio, C,-C,alkylsulfinyl, C4-C,alkylsulfonyl, C4-Cjalkyl-S(0).0, Cs-

Cahaloalkylthio, C,-Cyhaloalkyisulfinyl, C,-C;haloalkylsulfonyl, C-Cjhaloalkyl-S(0).0, Ci-

C.alkyl-S(O).NH, C;-C,alkyl-S(0O),N(C,-C,alkyl), halogen, nitro or by cyano; and

Rasy and Rj; are each independently of the other hydrogen or C,-Cjalkyl;

Raz and Rg, are each independently of the other hydrogen, hydroxy, C;-Cjalkyl, Co-Cealkenyl,

C,-Cealkynyl, C4-Caalkoxycarbonyl, C,-Cgalkylthio, C,-Cealkylsulfinyl, C,-Cgalkylsulfonyl,

C;-Caalkyl-NHS(O),, C;-Cshaloalkyl, -NH-C,-Cialkyl, -N(C,-C,alkyl)z, C,-Csalkoxy, cyano, nitro, halogen, or phenyl which may itself be substituted by C,-C,alkyl, C;-Chaloalkyl, C4-C,- alkoxy, C,-Czhaloalkoxy, C;-Caalkylcarbonyl, C4-Cjalkoxycarbonyl, amino, C,-Caalkylamino, di(C4-Cialkyl)amino, C,-Csalkylthio, C,-Cgalkylsulfinyl, C;-Csalkylsulfonyl, C,-C,alkyl-S(0),0,

C,-C4haloalkylthio, C4-Cghaloalkylsulfinyl, C,-Cshaloalkylsulfonyl, C,-Cjhaloalkyl-S(0),0,

C;-Caalkyl-S(O)oNH, C4-Cyalkyl-S(0).N(C,-C,alkyl), halogen, nitro, COOH or by cyano; or

Ras and Ra, together form a C»-Csalkylene bridge; and

Rss is hydrogen, Cq-Caalkyl, Cy-Cjalkoxycarbonyl, or phenyl which may itself be substituted by Ci-Caalkyl, C4-Cshaloalkyl, C;-Cjalkoxy, C4-Cjhaloalkoxy, Cy-Cjalkylcarbonyl, Cq-

C.alkoxycarbonyl, amino, C,-C,alkylamino, di(C;-C.alkyl)amino, C,-Cgalkylthio, Ci-

Caalkylsulfinyl, C4-Caalkylsulfonyl, C4-Caalkyl-S(0),0, C4-C,haloalkyithio, C,-

Cshaloalkylsulfinyl, C4-Cshaloalkylsulfonyl, C;-Cshaloalkyl-S(0),0, C,-C,alkyl-S(O).NH, C,-

Caalkyl-S(O).N(C,-Caalkyl), halogen, nitro, COOH or by cyano; - or is the group Qs

ZR,

Da! (Qs),

Reg O

So - wherein Z is sulfur, SO or SOy;

Ro: is hydrogen, C;-Cgalkyl, C4-Csalkyl substituted by halogen, C;-Cjalkoxy, C4-Calkylthio, ‘ C4-Caalkylsulfonyl, C4-C alkylsulfinyl, hydroxy, cyano, nitro, -CHO, -CO2Ry;. , -CORgs, . -COSRos , “NRosRos , CONRgssRos7, oF by phenyl which may itself be substituted by C;-

Caalkyl, C4-Cghaloalkyl, C;-Cjalkoxy, C4-Cshaloalkoxy, C,-Cealkenyl, Cs-Cgalkynyl, Cs-

Cealkenyloxy, Cs-Cealkynyloxy, halogen, nitro, cyano, -COOH, COOC;-Calkyl, COOQOphenyl,

C1-Cjalkoxy, phenoxy, (C;-Caalkoxy)-C4-Cjalkyl, (C-Caalkylthio)-C,-C alkyl, (Cq-

Caalkylsulfinyl)-C,-Cjalkyl, (C4-Caalkylsulfonyl)-C4-C.alkyl, NHSO,-C,-C,alkyl, NHSO,-phenyl,

N(C4-Cealkyl)SO,-C4-Caalkyl, N(C;-Cealkyl)SO,-phenyl, N(C,-Csatkenyl)SO,-C;-Caalkyl, N(Co-

Cealkenyl)SO,-phenyl, N(Cs-Csalkynyl)SO,-C;-C,alkyl, N(Cs;-Cealkynyl)SO,-phenyl, N(Cs-C;- cycloalkyl)SO,-Cy-Caalkyl, N(Cs-C;cycloalkyl)SO,-phenyl, N(phenyl)SO,-C,-C,alkyl,

N(phenyl)SO.-phenyl, 0SO,-C;-Caalkyl, CONRgzsRoz6, OSO,-C;-Cshaloalkyl, 0SO,-phenyl,

Ci-Caalkylthio, C4-C,haloalkyithio, phenylthio, C4-Calkylsulfonyl, C,-C,haloalkylsutfonyl, phenylsulfonyl, C;-Caalkylsulfinyl, C,-C,haloalkylsulfinyl, phenylsulfinyl, C4-C,alkylenephenyl or by -NRo1sCO2Roz7; or Ry is Co-Csalkenyl or C,-Cgalkenyl substituted by halogen, Cs-Cjalkoxy, C;-Caalkylthio,

C,-Caalkylsulfonyl, C;-Caalkylsulfinyl, -CONRs2Rgaz, cyano, nitro, -CHO, -CO»Rqss, -CORoas, -COS-C;-Cialkyl, -NRga4Ro3s, OF by phenyl which may itself be substituted by C,-C,alkyl,

C,-Cghaloalkyl, C,-Cjalkoxy, C4-Cshaloalkoxy, C,-Cgalkenyl, Cs-Csalkynyl, C;-Cealkenyloxy,

Cs-Cealkynyloxy, halogen, nitro, cyano, -COOH, COOC;-Cjalkyl, COOphenyl, C;-Cjalkoxy, phenoxy, (Cs-Caalkoxy)-Ci-Caalkyl, (Cs-Caalkylthio)-C,-Caalkyl, (C4-Caalkylsuifinyl)-Cy-Cialkyl, (C1-Caalkylsulfonyl)-C4-Cialkyl, NHSO.-C;-Caalkyl, NHSO,-phenyl, N(C1-Cealkyl)SO,-C4-C,y- alkyl, N(C4-Cealkyl)SO.-phenyl, N(C,-Cealkenyl)SO,-C;-Caalkyl, N(Co-Cealkenyl)SOz-pheriyl,

N(C3-Csalkynyl)SO,-C1-Caalkyl, N(C3-Cealkynyl)SO,-phenyl, N(Cs-C;cycloalkyl)SO.-Cy-C,- alkyl, N(Cs-C,cycloalkyl)SO.-phenyl, N(phenyl)SO,-C1-Caalkyl, N(phenyl)SO.-phenyl, 0S80,-C4-Caalkyl, CONRo4oRos1, 0SO,-C4-Cihaloalkyl, OSO,-phenyl, C4-Calkylthio, C4-C,- haloalkylthio, phenyithio, C,-Caalkylsulfonyl, C,-C;haloalkylsulfonyl, phenylsulfonyl, C,-C,- alkylsulfinyl, C,-Cshaloalkylsulfinyl, phenylsulfinyl, C;-C,alkylenepheny! or by -NRos3CO,Rs0; or Roy is Cs-Cealkynyl or Cs-Cealkynyl substituted by halogen, C,-C;haloalkyl, cyano, . -CO2Ro44, Or by phenyl which may itself be substituted by C,-Cjalkyl, C-Cshaloalkyl, C;-C,- alkoxy, C4-Cshaloalkoxy, Ca-Cealkenyl, Cs-Cealkynyl, Cs-Cealkenyloxy, Cs-Cealkynyloxy, ¢ halogen, nitro, cyano, -COOH, COQC;-C,alkyl, COOphenyl, C,-Cjalkoxy, phenoxy, (Cy~C,- alkoxy)-C4-Caalkyl, (C4-Caalkyithio)-Cy-C,alkyl, (Cs-Caalkylsulfinyl)-C,-C,alkyl, (C1-Csalkyl- sulfonyl)-C;-Caalkyl, NHSO,-C4-Caalkyl, NHSO,-phenyl, N(C;-Csalkyl)SO,-Cy-Caalkyl,

N(C;-Cealkyl)SO,-phenyl, N(Co-Csalkenyl)SO,-C4-C,alkyl, N(C2-Cealkenyl)SO.-phenyl, . N(Ca-Cealkynyl)SO,-C,-Caalkyl, N{(C3-Csalkynyl)SO,-phenyl, N(Cs-C,cycloalkyl)SO,-C1-Cas- alkyl, N(Cs-C,cycloalkyl)SO.-phenyl, N(phenyl)SO,-C,-Cjalkyl, N(phenyl)SO,-phenyl, 0S0,-C;-Cialkyl, CONRg2gR020, 0S0,-Cy-Chaloalkyl, OSO,-phenyl, C,-Caalkylthio, C1-Ca- haloalkyithio, phenylithio, C;-Caalkylsulfonyl, C;-Cshaloalkylsulfonyl, phenylsulfonyl, C;-Cas- alkylsulfinyl, C,-Cshaloalkylsulfinyl, phenylsulfinyl, C;-C,alkylenephenyl or by -NRy3;CO2Ro30; or Ros is G3-C;cycloalkyl or Cs-Creycloalkyl substituted by C4-Caalkyl, C4-Cialkoxy, Cs-

Caalkylthio, C4-Cjalkylsulfinyl, C4-Csalkylsulfonyl, or by phenyl which may itself be substituted by halogen, nitro, cyano, C;-Csalkoxy, C4-Cshaloalkoxy, C;-Cjalkylthio, C;-Cshaloalkylthio,

C,-Caalkyl or by C,4-Cjhaloalkyl; or

Ro: is C1-Caalkylene-Cy-C;cycloalkyl, phenyl, or phenyl substituted by Cy-Caalkyl, C,-Cghalo- alkyl, C;-Cjalkoxy, C4-Cghaloalkoxy, Co-Cealkenyl, C3-Cgalkynyl, Cs-Cgalkenyloxy, Cs-Ce- alkynyloxy, halogen, nitro, cyano, -COOH, COOC,-C,alkyl, COOphenyl, C;-Cjalkoxy, phenoxy, (C;-Cjalkoxy)-C,-Caalkyl, (C4-Csalkylthio)-C,-Caalkyl, (C4-Cialkylsulfinyl)-C;-Cjalkyi, (C4-Caalkylsulfonyl)-C4-Cgalkyl, NHSO.-C,-Cjalkyl, NHSO,-phenyl, N(C;-Cealkyl)SO2-C;-C.- alkyl, N(C,-Csalkyl)SO.-phenyl, N(C,-Cealkenyl)SO,-C4-Cjalkyl, N(C,-Csalkenyl)SO.-phenyi,

N(Cs-Cealkynyl)SO,-C,;-Cialkyl, N(C3-Csalkynyl)SO.-phenyl, N(Cs-C,cycloalkyl)SO,-C,;-C,- alkyl, N(C3s-C,cycloalkyl}SO.-phenyl, N(phenyl)SO,-C,-C,alkyl, N(phenyl)SO.-phenyl, 0S0,-C4-Cyalkyl, CONRysRo4s, OSO,-C4-Cyhaloalkyl, OSO2-phenyl, C,-Cialkylthio, C4-Cy- haloalkyithio, phenylthio, C,-C,alkylsulfonyl, C;-Cjhaloalkylsulfonyl, phenylsulfonyl, C;-C;- alkylsulfinyl, C,-C;haloalkylsuifinyl, phenylsulfinyl or by -NRgssCO2Rg47; OF

Roi is C;-Cialkylenephenyl, CORy; or from 4- to 6-membered heterocyclyl;

Roz, Ross, Ross and Regs are each independently of the others hydrogen, C4-Cjalkyl, phenyl, or phenyl substituted by C4-Cjalkyl, C,-Cghaloalkyl, C4-Casalkoxy, C4-Cshaloalkoxy, C,-Cealkenyl,

Cs-Cgalkynyl, Cs-Csalkenyloxy, Ca-Csalkynyloxy, halogen, nitro, cyano, -COOH, COOC;-C,- alkyl, COOphenyl, C;-Cjalkoxy, phenoxy, (C;-Calkoxy)-C;-Caalkyl, (C4-Casalkylthio)-C;-C,- alkyl, (C4-Caalkylsulfinyl)-C,-Cjalkyl, (Cy-Caalkylsulfonyl)-C,-Caalkyl, NHSO,-C,-Cjalkyl,

NHSO,-phenyl, N(C;-Csalkyl)SO2-C4-Caalkyl, N(C1-Cgalkyl)SOz-phenyl; N(Co-Cealkenyl)-

S0,-C4-Caalkyl, N(C2-Cgalkenyl)SO.-phenyl, N(C3-Csalkynyl)SO,-C,-Cgalkyl, N(C5-Ce- ‘ alkynyl)SO-phenyl, N(Cs-C;cycloalkyl)SO,-C4-Caalkyl, N(Cs-C;cycloalkyl)SO.-phenyl,

N(phenyl)SO,-C-Caalkyl, N(phenyl)SO.-phenyl, 0SO,-C,-Calkyl, CONRg49Ros0, ’ 0S0,-C4-Cyhaloalkyl, OSO,-phenyl, C;-C,alkylthio, C,-Cshaloalkylthio, phenylthio, C4-

Caalkylsulfonyl, C4-Cshaloalkylsulfonyl, phenylsulfonyl, C,-Cjalkylsulfinyl, C,-

Cjhaloalkylsulfinyl, phenylsulfinyl, -C;-C;-alkylphenyl or by -NRgs2CO2Rgss;

Ros, Ross and Rg; are each independently of the others C4-C,alkyl, phenyl, or phenyl . substituted by C,-C,alkyl, C4-Cshaloalkyl, C4-Caalkoxy, C4-Cjhaloalkoxy, Co-Cealkenyl, C3-Ce- alkynyl, Cs-Cealkenyloxy, Cs-Cealkynyloxy, halogen, nitro, cyano, -COOH, COOC,-C,alkyl,

N COOphenyl, C;-C,alkoxy, phenoxy, (C-Caalkoxy)-C;-C,alkyl, (C4-C,alkylthio)-C,-Caalkyl, (C4-C.alkylsulfinyl)-C4-C,alkyl, (C;-Cialkylsulfonyl)-C;-Caalkyl, NHSO,-C4-Caalkyl,

NHSO;-phenyl, N(C;-Cgalkyl)SO,-C4-Caalkyl, N(C1-Cgalkyl)SO,-phenyl, N(C,-Cgalkenyl)-

S02-C4-Caalkyl, N(C,-Cgalkenyl)SO,-phenyl, N(Cs-Cealkynyl)SO,-C1-Cialkyl, N(Cs-Cealkynyl)-

SOz-phenyl, N(C5-C;cycloalkyl)SO,-C4-Caalkyl, N(C5-C,cycloalkyl)SO,-phenyl, N(phenyl)-

S0,-C4-Caalkyl, N(phenyl)SO,-phenyl, OSO.-C1-Caalkyl, CONRgesRos4, OSO,-C4-Cshaloalkyl,

OSO.-phenyl, C,4-C,alkylthio, C4-Cshaloalkyithio, phenylthio, C,-C,alkylsulfonyl, C;-C,halo- alkyisulfonyl, phenylsulfonyl, C,-Caalkylsulfinyl, C;-Chaloalkylsulfinyl, phenylsulfinyl, ~(CHz)-phenyl or by -NRgs5CO2Ross;

Ros is Cy-Calkyl;

Ros is hydrogen, C;-Caalkyl, Co-Csalkenyl, C3-Cealkynyl, Cs-C,cycloalkyl, phenyl, or phenyl substituted by C,-Caalkyl, C,-Cghaloalkyl, C;-Cjalkoxy, C;-Cjhaloalkoxy, C,-Cgalkenyl, C3-Cs- alkynyl, Cs-Cealkenyloxy, Cs-Cealkynyloxy, halogen, nitro, cyano, -COOH, COOC;-C,alkyl,

COOphenyl, C;-C,alkoxy, phenoxy, (C;-Cjalkoxy)-C,-C,alkyl, (C4-C,alkylthio)-C,-C alkyl, (C,-Calkylsulfinyl)-C;-Caalkyl, (C4-Cjalkylsulfonyl)-C;-Cgalkyl, NHSO,-C,-Cqalkyl,

NHSO,-phenyl, N(C,-Cgalkyl)SO.-C4-Caalkyl, N(C1-Csalkyl)SO,-phenyl, N(C,-Cgalkenyl)-

SO,-C4-Caalkyl, N(C,-Cgalkenyl)SO.-phenyl, N(Cs-Cgalkynyl)SO,H, N(C3-Cealkynyl)-

S0,-C;-Caalkyl, N(C3-Cealkynyl)SO.-phenyl, N(Cs-Ccycloalkyl)SO.H, N(Cs-C;cycloalkyl)-

S0,-C,-Caalkyl, N(C3-Creycloalkyl)SO,-phenyl, N(phenyl)SO,-C,-Calkyl, N(phenyl)-

SO.-phenyl, OS0,-C4-Caalkyl, CONRgs7Ros8, OSO,-C4-Cyhaloalkyl, OSO-phenyl, Cs-Caalkyl- thio, C,-Cshaloalkylthio, phenylthio, C,-C,alkylsulfonyl, C;-Cjhaloalkylsulfonyl, phenylsulfonyl,

C,-Cqalkylsuifinyl, C,-Cshaloalkylsulfinyl, phenylsulfinyl, C-Cjalkylenephenyl or by ~NRpssCO2R oss;

Ros is hydrogen, C;-Cjalkyl, Co-Cealkenyl, Cs-Csalkynyl, C3-C,cycloalkyl, phenyl, or phenyl substituted by C,-C,alkyl, C;-Cghaloalkyl, C;-Cjalkoxy, C;-Cshaloalkoxy, C>-Csalkenyl,

Cs-Cealkynyl, G5-Cealkenyloxy, Cs-Cealkynyloxy, halogen, nitro, cyano, -COOH, COOC;-C,- g alkyl, COOphenyl, C,-C,alkoxy, phenoxy, (C4-Caalkoxy)-C4-Cialkyl, (C4-Calkyithio)-C,-C,- alkyl, (C4-Caalkylsulfinyl)-C,-Caalkyl, (C,-Caalkylsulfonyl)-C,-Cgalkyl, NHSO,-C4-Caalkyl, “ NHSO,-phenyl, N(C,-Csalkyl)SO,-C;-Cyalkyl, N(C;-Csalkyl)SO,-phenyl, N(C,-Cealkenyl)-

S02-Cs-Caalkyl, N(C2-Cealkenyl)SO,-phenyl, N(Cs-Csalkynyl)SO,-C;-Caalkyl, N(Cs-Ceatkynyl)-

SO,-phenyl, N(C4-Creycloalkyl)SO,-C,-C,alkyl, N(C5-Cscycloalkyl)SO,-phenyl, N(phenyi)-

S0,-C4-Cialkyl, N(phenyl)SO,-phenyl, OSO,-C4-C,alkyl, CONRgg1Ros2, OSO,-C4-Chaloalkyl, . OSO,-phenyl, C,-Caalkylthio, C4-C;haloalkyithio, phenyithio, C;-Caalkylsulfonyl, C,-Cshalo- alkylsulfonyl, phenylsulfonyl, C,-Cjalkylsulfinyl, C-C,haloalkylsulfinyl, phenylsulfinyl, C1-Ca- . alkylenepheny! or by -NRyssCO2Res;

Roz is phenyl, C,4-C,alkyl, C;-Caalkoxy or -NRggRos;

Rog and Rg are each independently of the other C;-C,alkyl, phenyl, or phenyl substituted by halogen, nitro, cyano, C-Cqalkyl, C;-Cialkoxy, C4-Cgthioalkyl, -CORges, “CORos7, C1-Ca- alkylsulfonyl, C;-Cgalkylsulfinyl or by C,-Cshaloalkyl; or Rqs and Rog together form a 5- or 6- membered ring, which may be interrupted by oxygen, NRggs or by S;

Rots, Rost, Ross, Ross, Ros, Ross, Roso and Rss are each independently of the others hydrogen,

Ci-Caalkyl, Co-Cealkenyl, C3-Cealkynyl or C3-C;cycloalkyl;

Rozs, Ros, Rozz, Rozs, Rozs, Roso, Rose, Ross, Roaa, Ross, Ross, Roa7, Roo, Ross, Roaz, Ross, Ross,

Ro47, Boag, Roso, Ross, Rosa, Ross, Ros, Ross, Rose, Rost, Rosz, Ross, Ross and Rees are each independently of the others hydrogen, C;-Cjalkyl, Co-Cealkenyl, Cs-Csalkynyl, Cs-C;cyclo- alkyl, phenyl, or phenyl substituted by halogen, nitro, cyano, C;-C,alkoxy, Ci-Cshaloalkoxy,

C,-Calkylthio, C,-C,haloalkylthio, C4-C,alkyl or by C;-Cshaloalkyl; and

Rag is C4-Caalkyl, Cs-Cyhaloalkyl, Cs-Cealkenyl, Cs-Cghaloalkenyl, Cs-Csalkynyl, Cs-Cghalo- alkynyl, Cs-Cecycloalkyl, or C;-Cecycloalky! substituted by halogen, C4-C,alkyl, C4-Cshalo- alkyl, Cs-Cgalkenyl, Cs-Cehaloalkenyl, Cs-Cealkynyl, Cs-Cghaloalkynyl, C4-C,alkoxycarbonyl,

C;-Caalkylthio, Cq-Cialkylsulfinyl, C,-Caalkylsulfonyl, C4-Cshaloalkylthio, C;-

Cjhaloalkylsulfinyl, C,-Cshaloalkylsulfonyl, C,-Cs,alkylcarbonyl, di(C+-Cjalkyl)amino, C;-

Cjalkoxy, C4-Cghaloalkoxy, C;-Caalkyl-S(0),0, C;-Cjhaloalkyl-S(0),0, or by phenyl which may itself be substituted by halogen, C;-Cjalkyl, Ci-Cshaloalkyl, C3-Cealkenyl, Cs-Cgalkynyl, cyano, nitro or by COOH; or an agronomically acceptable salt of such a compound, and b) a synergistically effective amount of one or more compounds selected from a compound of formula 2.1 ] Rg, Nn COOH

Spr

Rss N = Me (2.1), i Me 0 wherein Rs; is CH,-OMe, ethyl or hydrogen;

Rsz is hydrogen or Rs; and Rs, together are the group -CH=CH-CH=CH-; . and a compound of formula 2.2

Res + Pes

N (2.2),

Jono

Rg, O wherein Rs; is ethyl, Rs, is methyl or ethyl and Rss is -CH(Me)-CH,OMe, <S>-CH(Me)-CH,OMe, CH,OMe or CH,O-CH,CHj; and a compound of formula 2.3

Me : R = / 56 / N (2.3),

S Jere

Me © wherein Rsg is CH(Me)-CH,OMe or <S>CH(Me)-CH.OMe; and a compound of formula 2.4

N” SN

JA a ee

Ny NG Ne :

H H wherein Rs; is chlorine, methoxy or methylthio, Rss is ethyl and Rs is ethyl, isopropyl, -C(CN)(CHj3)-CH; or tert-butyl; and a compound of formula 2.5 0 X

Rg; 0 wherein Rg is ethyl or n-propyl, Res is COO” 1/2 Ca™, -CH,-CH(Me)S-CH,CH; or the group

AG! and X is oxygen, N-O-CH,CHs or N-O-CH,CH=CH-CI; and a compound of formula 2.6

Rez

H Oo N— PY ” N= = PY 0 N 1% Res (2.6),

Res

Res wherein Rg; is hydrogen, methoxy or ethoxy, Res is hydrogen, methyl, methoxy or fluorine,

Res is COOMe, fluorine or chlorine, Rgs is hydrogen or methyl, Y is methine, C-F or nitrogen,

Z is methine or nitrogen and Rg; is fluorine or chlorine; and a compound of formula 2.7

Rez 0” aN (2.7), “NT cf wherein Rg; is hydrogen or -C(0)-S-n-octyl; and a compound of formula 2.8

OH

’ Res Res (2.8),

CN

‘ wherein Rg; is either bromine or iodine; and a compound of formula 2.9

0 0) Reo

O (2.9), g “Me wherein Rg is chlorine or nitro; and a compound of formula 2.10

Ro Q pL cl N (2.10), \

Poe

R,{ wherein Ryo is fluorine or chlorine and Ry is -CH>-CH(CI)-COOCH,CH; or -NH-SO,Me; and a compound of formula 2.11

Me \ 0

ZS oO 2.11),

R,, (2.11) 7 \

NO

O wherein Ry; is trifluoromethyl or chlorine; and a compound of formula 2.12

P COOH

Me” | hd (2.12), © R

NH,* | 73 “ wherein Ry; is NH, or <S>NH; and a compound of formula 2.13

R

Tl 74 I

WAAL 9 NY as, " oN J Js ML ® 0 I N N Ye

H H wherein Y, is nitrogen, methine, NH-CHO or N-Me, Y. is nitrogen, methine or C-l, Y; is methine, Y, is methine or Y; and Y, together are sulfur or C-Cl, Ys is nitrogen or methine, Yg is methyl, difluoromethoxy, trifluoromethyl or methoxy, Y; is methoxy or difluoromethoxy and

R74 is CONMe,, COOMe, COOC Hs, trifluoromethyl, CH,-CH,CF3 or SO,CH,CHs, or a sodium salt thereof ("Me" being in each case the methyl group); and the compound of formula 2.13.c

O CH, : Cl 9) o- CH,

Ax

N. S 213.c

N > ~NH N XX (2.13.¢c),

Oo CH

CH ~ 3 3 oA N~ NT To

H and the compound of formula 2.14

Me N—N Me

Me / Hs

Me N (2.14), 0) N—H /

H and the compound of formula 2.15

HN Cl and the compound of formula 2.16

INT

. HOOC PO(OH), (2.16),

H and the compound of formula 2.17 : N Me } 0 (2.17),

Ng\

O

H and the compound of formula 2.18

Oo \

Me No : H / — (2.18), te Me 0 Me and the compound of formula 2.19

Cl

Cp (2.19),

Cl OMe and the compound of formula 2.20 oo 0]

Me PIS Et he sg” (2.20),

Me Me .

Me ‘ and the compound of formula 2.21

®) pa \

Oo 0] Me

Me (2.21),

Ao

Me

Oo

L, and the compound of formula 2.22

Ci 0

ON (2.22), o Me

Me and the compound of formula 2.23 oo cl

Se (2.23), coon and the compound of formula 2.24 :

F O : ‘ 0 0 (2.24),

Id ol 0 / n-pentyl .

) and the compound of formula 2.25 & F

N Ci N 7) (2.25), >or

MeOOC O and the compound of formula 2.26

Me

CF, H—n 6]

CCT em ae and the compound of formula 2.27

F O eas " 4 (2.27),

R: / va and the compound of formula 2.28

Me—Ny / \ Me (2.28), cr Cl and the compound of formula 2.29 cl Q & J.

Cl NG

N (2.29) of ) v4 and the compound of formula 2.30

Me yas N (2.30),

FC S oY F 0) and the compound of formula 2.31 @! Pi yi

N N 2.31), \ J A 23)

N=N L

Me and the compound of formula 2.32

F Br

CF, ~—I

Ci

NN

Me (2.32), 0 0 e—(

Me ) and the compound of formula 2.33 ] H 0

HOOC ) l - i

NNN O0 pe—8Me (239)

OH

Me and the compound of formula 2.34

HN ~ MH SO,NHCO,CH, (2.34), and the compound of formula 2.35

CF, =N

CH,NH {0 (2.35),

Cl 0) and the compound of formula 2.36

CH, _N.__O

XT (2.36), a ~C(CH,),

O . ¢S CH,CH(CH,), and the compound of formula 2.37 ~~ N De thik (2.37),

F.C” N” CEH :

F.C N_ CHF, and the compound of formula 2.38 sro nA COSCH, (2.38),

CH,CH(CH,), on (CH,),N N 0) and the compound of formula 2.39 M T (2.39),

FO

© and the compound of formula 2.40 oa )- NHCON(CH,), (2.40),

Cl

Cl OCH,CO_H : i and the compound of formula 2.41 & zg-re (2.41),

CH,

CH,

I and the compound of formula 2.42 © ~{)-obieon (2.42),

CH, os

S

(CH,,C ~ ba NCONHCH, and the compound of formula 2.43 N-N (2.43), and the compound of formula 2.44

H,C CH,

Oo i

CHCl (2.44),

OCH,CH, and the compound of formula 2.45 o © Oo 0 Ox Vi o) S

HC VN

3 A h=( (2.45),

AN

CH, and the compound of formula 2.46 0 . ’ O-isopropy!

H.C N

N— “ NN a (2.46),

Na

CF;

Br F and the compound of formula 2.47 » 0)

OCH,CH, ra O —

Cl (2.47), (I<) (0) and the compound of formula 2.48

CH, F ] F ~ F (2.48), oo zr o oO

H.C = 0 CH, [¢] and the compound of formula 2.49

F

CH, 0)

SR

(2.49), = o F

HO and the compound of formula 2.50

CH, Nig ~~ CH 3

HC N NSC (2.50)

CH, >—N CH, 0) \

NH, and the compound of formula 2.51

F O CH,

F

Co Cl {H- = F

N— F 0 (2.51).

Oo , CH, o—/

In the above formulae, "Me" is a methyl group. The alkyl groups appearing in the substituent definitions may be straight-chained or branched and are, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl and dodecyl and also branched isomers thereof. Alkoxy, alkenyl and alkynyl radicals are derived from the mentioned alkyl radicals. The alkenyl and alkynyl groups may be unsaturated once or more than once.

An alkylene group may be substituted by one or more methyl groups; preferably, such alkylene groups are unsubstituted in each case. The same also applies to all Cs-

Cscycloalkyl-, C3-Csoxacycloalkyl-, Cs-Csthiacycloalkyl-, Cs-C,dioxacycloalkyl-,

Cs-Cydithiacycloalkyl-, Cs-Cjoxathiacycloalkyl- and N(CH,)-containing groups.

Halogen is, generally, fluorine, chlorine, bromine or iodine. The same correspondingly applies to halogen in the context of other definitions, such as haloalkyl or halophenyl.

Haloalkyl groups having a chain length of from 1 to 6 carbon atoms are, for example, fluoro- methyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyi, trichloromethyl, 2,2,2- trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, pentafluoroethyl, 1,1-difluoro-2,2,2-trichloroethyl, 2,2,3,3-tetrafluoroethyl and 2,2,2-trichloroethyl, pentafluoroethyl, heptafluoro-n-propyl, perfluoro-n-hexyl; haloalkyl groups in the definitions of Ry, R; and especially Rs are preferably trichloromethyl, dichlorofluoromethyl, difluorochloromethyl, difluoromethyl, trifluoromethyl, pentafluoroethyl or heptafluoro-n-propyl.

Suitable haloalkenyl radicals include alkenyl groups substituted one or more times by halogen, halogen being fluorine, chlorine, bromine or iodine and especially fluorine or . chlorine, for example 2,2-difluoro-1-methylvinyl, 3-fluoropropenyl, 3-chloropropenyl, 3-bromopropenyl, 2,3,3-trifluoropropenyl, 2,3,3-trichloropropenyl and 4,4,4-trifluorobut-2-en- 1-yl. Preferred C»-Cyzalkenyl radicals substituted once, twice or three times by halogen are those having a chain length of from 2 to 5 carbon atoms. Suitable haloalkynyl radicals include, for example, alkynyl groups substituted one or more times by halogen, halogen . being bromine or iodine and, especially, fluorine or chlorine, for example 3-fluoropropynyl, 3-chloropropynyl, 3-bromopropynyl, 3,3,3-trifluoropropyny! and 4,4,4-trifluoro-but-2-yn-1-yl. . Preferred alkynyl groups substituted one or more times by halogen are those having a chain length of from 2 to 5 carbon atoms.

Alkoxy groups preferably have a chain length of from 1 to 6 carbon atoms. Alkoxy is, for example, methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy or tert- butoxy or a pentyloxy or hexyloxy isomer, preferably methoxy and ethoxy. Alkylcarbonyl is preferably acetyl or propionyl. Alkoxycarbonyl is, for example, methoxycarbonyl, ethoxy- carbonyl, propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxycarbonyl, sec- butoxycarbonyl or tert-butoxycarbonyl, preferably methoxycarbonyl, ethoxycarbonyl or tert- butoxycarbonyl. Haloalkoxy groups preferably have a chain length of from 1 to 8 carbon atoms.

Haloalkoxy is, for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoro- ethoxy, 1,1,2,2-tetrafluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2-difluoroethoxy or 2,2,2- trichloroethoxy, preferably difluoromethoxy, 2-chloroethoxy or trifluoromethoxy.

Alkylthio groups preferably have a chain length of from 1 to 8 carbon atoms.

Alkylthio is, for example, methylthio, ethylthio, propyithio, isopropylthio, n-butylthio, isobutyl- thio, sec-butylthio or tert-butylthio, preferably methyithio or ethylthio. Alkylsulfinyl is, for example, methylsulfinyl, ethylsulfinyl, propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, isobutyl- sulfinyl, sec-butylsulfinyl or tert-butylsulfinyl, preferably methylsuifinyl or ethyisulfinyl.

Alkylsuifonyl is, for example, methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl or tert-butylsulfonyl, preferably methyl- sulfonyl or ethylsulfonyl. : Alkylamino is, for example, methylamino, ethylamino, n-propylamino, isopropylamino or a butylamine isomer. Dialkylamino is, for example, dimethylamino, methylethylamino, diethyl- amino, n-propylmethylamino, dibutylamino or diisopropylamino. Preference is given to ! alkylamino groups having.a chain length of from 1 to 4 carbon atoms. Alkoxyalkyl groups preferably have from 1 to 6 carbon atoms. Alkoxyalkyl is, for example, methoxymethyl, ’ methoxyethyl, ethoxymethyl, ethoxyethyl, n-propoxymethyl, n-propoxyethyl, isopropoxy- methyl or isopropoxyethyl. Alkylthioalkyl groups preferably have from 1 to 6 carbon atoms.

Alkylthioalkyl is, for example, methyithiomethyl, methylthioethyl, ethylthiomethyi, ethylthio-

ethyl, n-propylthiomethyl, n-propylthioethyl, isopropylthiomethyl, isopropylthioethyl, butylthio- . methyl, butylthioethy! or butylthiobutyl. : The cycloalkyl groups preferably have from 3 to 6 ring carbon atoms and may be substituted by one or more methyl groups; they are preferably unsubstituted, for example cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. Phenyl, including phenyl as part of a substituent such as phenoxy, benzyl, benzyloxy, benzoyl, phenylthio, phenylalkyl, phenoxyalkyi or tosyl, may be in mono- or poly-substituted form, in which case the substituents may, as desired, be in the ortho-, meta- and/or para-position(s).

The invention also includes the salts that the compounds of formula | may form with amines, alkali metal and alkaline earth metal bases or quaternary ammonium bases. Among the alkali metal and alkaline earth metal hydroxides used as salt formers, emphasis is to be given to the hydroxides of lithium, sodium, potassium, magnesium and calcium, but especially those of sodium and potassium.

Examples of suitable amines for ammonium salt formation that come into consideration are ammonia as well as primary, secondary and tertiary C,-Cjgalkylamines, C;-Cshydroxyalkyl- amines and C,-C,alkoxyalkylamines, for example methylamine, ethylamine, n-propylamine, isopropylamine, the four butylamine isomers, n-amylamine, isoamylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, methyl-ethylamine, methyl-isopropylamine, methyl- hexylamine, methyl-nonylamine, methyl-pentadecylamine, methyi-octadecylamine, ethyl- butylamine, ethyl-heptylamine, ethyl-octylamine, hexyl-heptylamine, hexyl-octylamine, dimethylamine, diethylamine, di-n-propylamine, diisopropylamine, di-n-butylamine, di-n- amylamine, diisoamylamine, dihexylamine, diheptylamine, dioctylamine, ethanolamine, n-propanolamine, isopropanolamine, N,N-diethanolamine, N-ethylpropanolamine, N-butyl- ethanolamine, allylamine, n-butenyl-2-amine, n-pentenyl-2-amine, 2,3-dimethylbutenyl-2- amine, dibutenyl-2-amine, n-hexenyl-2-amine, propylenediamine, trimethylamine, triethyl- i amine, tri-n-propylamine, triisopropylamine, tri-n-butylamine, triisobutylamine, tri-sec- butylamine, tri-n-amylamine, methoxyethylamine and ethoxyethylamine; heterocyclic amines, for example pyridine, quinoline, isoquinoline, morpholine, piperidine, pyrrolidine, indoline, quinuclidine and azepine; primary aryl amines for example anilines, methoxyanilines, ethoxyanilines, o-, m- and p-toluidines, phenylenediamines, benzidines, naphthylamines and

0-, m- and p-chloroanilines; but especially triethylamine, isopropylamine and diisopropyl-

N amine. . It is extremely surprising that the combination of the active ingredient of formula | with one or more active ingredients selected from formulae 2.1 to 2.51 exceeds the additive effect on the weeds to be controlled that is to be expected in principle, and thus broadens the range of action of the individual active ingredients especially in two respects: Firstly, the rates of application of the individual compounds of formulae 1 and 2.1 to 2.51 are reduced while a good level of action is maintained and, secondly, the composition according to the invention achieves a high level of weed control also in those cases where the individual substances, in the range of low rates of application, have become unusable from the agronomic standpoint. } The result is a considerable broadening of the spectrum of weeds and an additional increase in selectivity in respect of the crops of useful plants, as is necessary and desirable in the event of an unintentional overdose of active ingredient. The composition according to the invention, while retaining excellent control of weeds in crops of useful plants, also enables greater flexibility in succeeding crops.

The composition according to the invention can be used against a large number of agronomically important weeds, such as Stellaria, Nasturtium, Agrostis, Digitaria, Avena,

Setaria, Sinapis, Lolium, Solanum, Phaseolus, Echinochloa, Scirpus, Monochoria, Sagittaria,

Bromus, Alopecurus, Sorghum halepense, Rottboellia, Cyperus, Abutilon, Sida, Xanthium,

Amaranthus, Chenopodium, Ipomoea, Chrysanthemum, Galium, Viola and Veronica. The composition according to the invention is suitable for all methods of application conventionally used in agriculture, e.g. pre-emergence application, post-emergence application and seed dressing. The composition according to the invention is suitable especially for controlling weeds in crops of useful plants, such as cereals, rape, sugar beet, sugar cane, plantation crops, rice, maize and soybeans, and also for non-selective weed control. : "Crops" are to be understood to mean also those crops which have been made tolerant to herbicides or classes of herbicides as a result of conventional methods of breeding or genetic engineering.

Preferred compositions according to the invention comprise compounds of formula | wherein each R is independently hydrogen, C,-Cgalkyl, C»-Csalkenyl, C>-Cghaloalkenyl, C,-Cgalkynyl, . Cz-Cehaloalkynyl, Cs-Cecycloalkyl , C,-Cgalkoxy, C4-Cghaloalkoxy, C;-Cealkylthio, C;-Cealkyl- sulfinyl, C4-Cealkylsulfonyl, C,-Cg¢haloalkyl, C,-Cghaloalkylthio, C;-Cghaloalkylsulfinyl, C1-Ce-

R haloalkylsulfonyl, C4-Csalkoxycarbonyl, C;-Cealkylcarbonyl, C;-Cealkylamino, di(C4-Cgalkyl)- amino, C;-Cealkylaminosulfonyl, di(C;-Csalkyl)aminosulfonyl, -N(R;)-S-Ra, -N(R3)-SO-R,, -N(Rs)-SO:-Rg, nitro, cyano, halogen, hydroxy, amino, benzylthio, benzylsulfinyl, benzyl- sulfonyl, phenyl, phenoxy, phenylthio, phenylsulfinyl or phenylsulfonyl; wherein the phenyl group may itself be mono-, di- or tri-substituted by C,-Cgalkyl, C;-Cghaloalkyl, C3-Csalkenyl,

Cs-Cghaloalkenyl, C;-Cgalkynyl, C3-Cghaloalkynyl, C;-Cealkoxy, C4-Cghaloalkoxy, Cs-Ce- alkenyloxy, Cs-Cgalkynyloxy, mercapto, Cs-Cgalkylthio, C4-Cghaloalkylthio, Cs-Cealkenylthio,

Cs-Cghaloalkenylthio, Cs-Cealkynyithio, C,-Csalkoxyalkylthio, Cs-Csacetylalkylthio, Cs-Ce- alkoxycarbonylalkylthio, C»-C,cyanoalkyithio, C,-Cealkylsulfinyl, C,-Cghaloalkylsulfinyl,

C;-Cealkylsulfonyl, C,-Cghaloalkylsulfonyl, aminosulfonyi, C4-C.alkylaminosulfonyl,

C,-C,dialkylaminosulfonyl, C;-Caalkylene-R,s, NR4sR47, halogen, cyano, nitro, phenyl or by benzylthio, wherein the latter phenyl and benzylthio groups may themselves be substituted on the phenyl ring by C;-Csalkyl, C,-Cshaloalkyl, C,-Csalkoxy, C;-Czhaloalkoxy, halogen, cyano or by nitro; or each R is independently a monocyclic or fused bicyclic ring system having from 5 to 10 members, which may be aromatic or partially saturated and may contain from 1 to 4 hetero atoms selected from nitrogen, oxygen and sulfur; wherein the ring system either is bound directly to the pyridine ring or is bound to the pyridine ring via a C,-C,alkylene group, and each ring system may not contain more than two oxygen atoms and may not contain more than two sulfur atoms, and the ring system may itself be mono-, di- or tri-substituted by

C;-Cealkyl, C4-Cghaloalkyl, Cs-Cgalkenyl, Cs-Cshaloalkenyl, Cs-Cealkynyl, Ca-Cghaloalkynyl,

C-Cgalkoxy, C,-Cghaloalkoxy, C,-Cgalkenyloxy, Cs-Cgalkynyloxy, mercapto, C4-Csalkylthio,

C;-Cghaloalkylthio, Cs-Cgalkenylthio, Cs-Cgshaloalkenylthio, Cs-Csalkynylthio, Co-

Csalkoxyalkylthio, Cs-Csacetylalkylthio, C;-Csalkoxycarbonylalkylthio, C.-Cacyanoalkylthio,

C,-Cealkylsulfinyl, C;-Cghaloalkylsulfinyl, C,-Cealkylsulfonyl, C;-Cghaloalkylsulfonyl, : aminosulfonyl, C4-Calkylaminosulfonyl, C,-C,dialkylaminosulfonyl, C,-Csalkylene-R;, NRgR., : halogen, cyano, nitro, phenyl or by benzyithio, wherein phenyl and benzylthio may themselves be substituted on the phenyl ring by C;-Csalkyl, C;-Cshaloalkyl, C,-Cjalkoxy, C,- ’ Cshaloalkoxy, halogen, cyano or by nitro, and wherein the substituents on the nitrogen in the heterocyclic ring are other than halogen.

Compositions according to the invention that are also preferred comprise, as compound of . formula I, a compound of formula la 0 —

Rss N Ris wherein

Rag is C4-Cealkyl, Co-Cealkenyl, Co-Cghaloalkenyl, Co-Cgalkynyl, C,-Cghaloalkynyl, Cs-Cscyclo- alkyl, C,-Cghaloalky!, or a monocyclic or fused bicyclic ring system having from 5 to 10 members, which may be aromatic or partially saturated and may contain from 1 to 4 hetero atoms selected from nitrogen, oxygen and sulfur, wherein the ring system either is bound directly to the pyridine ring or is bound to the pyridine ring via a C,-C,alkylene group, and each ring system may not contain more than two oxygen atoms and may not contain more than two sulfur atoms, and the ring system may itself be mono-, di- or tri-substituted by

C,-Cealkyl, C;-Cghaloalkyl, C,-Cgalkenyl, Cs-Cghaloalkenyl, Cs-Csalkynyl, Cs-Cghaloalkynyl,

C4-Cealkoxy, C,-Cghaloalkoxy, Cs-Cealkenyloxy, Cs-Cealkynyloxy, mercapto, C;-Cgalkylthio,

C;-Cghaloalkylthio, Cs-Cealkenylthio, Cs-Cghaloalkenyithio, Cs-Cgalkynyithio, C,-Csalkoxy- alkylthio, Ca-Csacetylalkyithio, Cs-Csalkoxycarbonylalkylthio, C,-C,cyanoalkyithio, Cy-Cgalkyl- sulfinyl, C4-Cghaloalkylsulfinyl, C,-Csalkylsulfonyl, C,-Cghaloalkylsulfonyl, aminosulfonyl,

C,-Czalkylaminosulfonyl, C,-C,dialkylaminosulfonyl, Ci-Csalkylene-R;, NRgR,, halogen, cyano, nitro, phenyl or by benzylthio, wherein phenyl and benzyithio may themselves be substituted on the phenyl ring by C;-Csalkyl, C4-Cshaloalkyl, C1-Csalkoxy, C;-Cshaloalkoxy, halogen, cyano or by nitro, and wherein the substituents on the nitrogen in the heterocyclic ring are other than halogen;

Rs is hydrogen, C4-Cealkyl, C4-Cghaloalkyl, halogen, or phenyl which may be substituted by

C,-Calkyl, Cy-Cshaloalkyl, C;-Csalkoxy, C,-Cshaloalkoxy, halogen, cyano or by nitro, and

Rso is C1-Cghaloalkyl.

Among that group of compounds preference is given to those wherein Rag is Cy-Cgalkyl, ’ C.-Cealkenyl, Co-Cghaloalkenyl, C,-Cealkynyl, C,-Cshaloalkynyl, Cs-Cecycloalkyl or Ci-Ce- haloalkyl.

Preference is given also to compositions wherein, in formula I, Q is the group Q, or Qs, . wherein, especially, in the group Q, Ra; is hydroxy and in the group Qs Ryo is hydroxy.

Among that group emphasis is to be given to those compounds wherein mis 2 and one . substituent R is C;-Caalkoxy-C4-C.alky! or C1-Caalkoxy-C;-Cialkoxy-Cq-Cgalkyl.

Further preferred synergistic mixtures according to the invention comprise as active ingredients a compound of formula | and either a compound of formula 2.2.a

CH, free

N (2.2.a, aRS,1'S(-)N-(1-methyl-2-methoxyethyl)-N-

HE=—CH,0CH,

C,H, CH, chloroacetyl-2-ethyl-6-methylaniline), or a compound of formula 2.2.b

CH,

FOreHC "\ (2.2.b)

Hy CH,0CH,

C,Hg CH, or a compound of formula 2.2 wherein Rs is ethyl, R, is methyl and Rs is ethoxymethyl, or a compound of formula 2.2 wherein Rj is ethyl, R, is ethyl and Rs is methoxymethyl, or a compound 2.3, or 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 a compound of formula 2.6 wherein Ry, is hydrogen, Z is methine, R43 is methyl, Y is nitrogen, Rs, is fluorine, Rys is hydrogen and Rs is fluorine, or R;; is methoxy, Z is methine, Ris is methoxy, Y is methine,

Ri4 is chlorine, Ry5 is methyl and Rg is chlorine, or a compound of formula 2.7 wherein Ris is -C(0O)-S-n-octyl, or a compound of formula 2.12, or a compound of formula 2.18, or a compound of formula 2.19, or a compound of formula 2.21, or a compound of formula 2.25, ¢ or a compound of formula 2.33, or a compound of formula 2.45, or a compound of formula 2.1.

Especially preferred synergistic mixtures according to the invention comprise as active ingredients a compound of formula | and either a compound of formula 2.2.a

CH, “ O-CRC

AN (2.2.a, aRS, 'S(-)N-(1-methyl-2’-methoxyethyl)-N- : HG—CH,0CH,

C,H, CH, chloroacetyl-2-ethyl-6-methylaniline), or a compound of formula 2.2.b

CH,

LOCH

N (2.2.b),

HG—CR,0CH,

C,H; CH, or a compound of formula 2.2 wherein R; is ethyl, R, is methyl and Rs is ethoxymethyl, or a compound of formula 2.2 wherein R; is ethyl, Ry is ethyl and Rs is methoxymethyl, or a compound of formula 2.3, or a compound of formula 2.30.

Combinations of the compounds of formula | with the compound of formula 2.2a

CH,

O-CHC

AN (2.2a, aRS,1’S(-)N-(1’-methyl-2’-methoxyethyl)-N-

HE—CH,0CH,

C,H, CH, _chloroacetyl-2-ethyl-6-methylaniline) have been found to be especially effective, the compound 1.001 indicated hereinbelow under Table 1 being especially preferred as the compound of formula 1. ' The compounds of formula | can be prepared in a manner analogous to the processes described in WO 97/46530, by a) reacting a compound of formula II

0)

X

. (In),

N

(R) m wherein R and m are as defined for formula | and X is a leaving group, e.g. halogen, in an inert, organic solvent in the presence of a base, with compounds of formula Hil, 1V,V or VI 0] R

Rs Ra \ Ry, (In) IV ” TR VY . , , 37 , i wo Low 20 R 9)

Rg Re v Ra Rag

R 4 :

R 33 ~

Ra (VI), o) N”

R 35 wherein Ry, R23, Rap and Ry are hydroxy and the other substituents are as defined for formula I, to form the compounds of formula VII, VIII, IX or X

NTR

(Rn NT = (Rn

Z . 0" "0

R 0 0 (vi, 16

LL ow 0 o R

R 19 R 18 7 ©

NT NT a (R)n | (Rn

LZ = 0) 0 0) le} d Ra (1X), Rg (X), ~ = w Ry 0 Ba, 0 0] N”

Rj Rag R 35 and then isomerising those compounds, for example in the presence of a base and a catalytic amount of dimethylaminopyridine (DMAP) or a cyanide source; or b) reacting a compound of formula XI 0 .

OH

(XI),

N

R

R) _ wherein R and m are as defined for formula 1, with compounds of formula lll, IV, V or Vi in an inert, organic solvent in the presence of a base and a coupling agent, to form the compound of formula VII, VIII, IX or X, and then isomerising that compound, for example in the manner described under route a).

Compounds of formula | wherein Q is a group Qs

ZR, \ a. Da! (Qs), ; ; R 36 Oo wherein Z is sulfur and Rss and Ro, are as defined for formula I, can be prepared in a manner analogous to known processes (e.g. those described in WO 97/43270), by either a) converting a compound of formula XII

(Rm [e] R 36 TE (Xn), o oN wherein Rg, R and m are as defined, in the presence of a base, carbon disulfide and an alkylating reagent of formula XIII

Ro1-X4 (Xn, wherein Ry, is as defined for formula I and X; is a leaving group, e.g. halogen or sulfonate, into the compound of formula XIV (Rm 0} 0

Ras (XIV),

IN

Rul ZR, wherein Z is sulfur and R, Rg, Rss and m are as defined, and then cyclising that compound = with hydroxylamine hydrochloride, optionally in a solvent, in the presence of a base, to form the compound of formula le 0 ZR, = AN (le)

N H

(RIM—Z, \ £1

Rss wherein Z is sulfur and R, Rss, Rot and m are as defined, and then oxidising that compound with an oxidising agent, e.g. meta-chloroperbenzoic acid (m-CPBA).

Preparation of the compounds of formula | is illustrated in greater detail in the following

Reaction Schemes 1 and 2.

Reaction Scheme 1 i route a): 0 * ZA X base, e.g. (C,H,).N, (Rm | + WM, WV, VorVi — TT Res yy Vi, VIL 1X, or X x solvent, e.g. CH,Cl,,

N 0-110°C i isomerisation: 0 base, e.g. (C,H;),N, or —_— > (R)m

KCN cat. SN ] route b): 0 base, e.g. (C_H.).N, couplin

Z JN OH I, IV, Vor Vi base, e.g. (GN, coupling Vil, VIL, IX, or X (Rm | N reagent, e.g. Xn

NN .

N | =

XI "N+

CH, solvent, e.g. CH,Cl,, 0-110°C isomerisation: oO base, e.g. (C,H),N, ZZ Q

KCN > Am . cat. N ]

The compounds of formula | containing the groups Q4, Q., Qs; and Q, wherein Rg, Ras, Rap and Ry are hydroxy can especially be prepared according to the above Reaction Scheme.

Reaction Scheme 2 0 - Pi K,CO4/CS,, Ry, =X, 0 c R Xi Rim =~ R i I Ls LL

NS , - + N = xl Nesp,” “SRu solvent, e.g. CH,CN, or

X11 NaM/CS,, R,-X,, Xv

Xi solvent, e.g. DMSO ) o O ,—R 01 (Fm z—R = A

NH,OH - HCI, base, e.g. [Sn [0], e.g. m-CPBA (gym — | AN 2 I —_ N 0

NaOAc/C,H,0H Nh or solvent, e.g. CHCl, oe when Z = 80- or SO,- whenZ =S

For preparation of the compounds of formula | wherein Q is a group Q; to Q4 and Rag, Ras,

Rao and Ryo are hydroxy, there are used as starting materials, in accordance with Reaction

Scheme 1, route a), the carboxylic acid derivatives of formula Il wherein X is a leaving group, for example halogen, e.g. iodine, bromine or especially chlorine, N-oxyphthalimide or N,O- dimethylhydroxylamino or a moiety of an activated ester, for example Oregmd 0O- (formed from dicyclohexylcarbodiimide (DCC) and the appropriate carboxylic acid) or

CN= THRICHINER,), (formed from N-ethyl-N’-(3-dimethylaminopropyl)carbodiimide (EDC) and the appropriate carboxylic acid). Those compounds are reacted in an inert, organic solvent, for example a halogenated hydrocarbon, e.g. dichloromethane, a nitrile, e.g. acetonitrile, or an aromatic hydrocarbon, e.g. toluene, and in the presence of a base, for example an alkylamine, e.g. triethylamine, an aromatic amine, e.g. pyridine or 4-dimethyl- aminopyridine (DMAP), with the dione derivatives of formula Ili, IV, V or VI to form the isomeric enol ethers of formula VII, Vill, IX and X. The esterification occurs at temperatures of from 0°C to 110°C.

The isomerisation of the ester derivatives of formulae VII, VIii, IX and X to form the dione derivatives of formula | (wherein Ry, Rays, Rs and Ry are hydroxy) can be carried out, for example, analogously to EP 369 803 in the presence of a base, for example an alkylamine, e.g. triethylamine, a carbonate, e.g. potassium carbonate, and a catalytic amount of DMAP or a cyanide source, for example acetone cyanohydrin or potassium cyanide.

According to Reaction Scheme 1, route b), the desired diones of formula | (wherein Rag, Ras,

Rao and Ry are hydroxy) can be obtained, for example, analogously to Chem. Lett. 1975, 1045 by means of esterification of the carboxylic acids of formula XI with the dione ’ derivatives of formula Ill, IV, V or VI in an inert solvent, for example a halogenated hydro- carbon, e.g. dichloromethane, a nitrile, e.g. acetonitrile, or an aromatic hydrocarbon, e.g. toluene, in the presence of a base, for example an alkylamine, e.g. triethylamine, and a - coupling agent, for example 2-chloro-1-methyl-pyridinium iodide. The esterification occurs, depending on the solvent used, at temperatures of from 0°C to 110°C and yields first, as described under route a), the isomeric ester of formula I, which can be isomerised, as described under route a), for example in the presence of a base and a catalytic amount of

DMAP, or a cyanide source to form the desired dione derivatives of formula | (wherein Ryo,

Ras, Ra and Ry are hydroxy).

Preparation of the compounds of formula | wherein Q is the group Qs can be carried out in accordance with Reaction Scheme 2, by reacting the b-diketone derivative of formula XIl, for example analogously to Synthesis 1991, 301; ibid. 1988, 793; or Tetrahedron 32, 3055 (1976), with carbon disulfide in the presence of a base, for example a carbonate, e.g. potassium carbonate, a metal hydride, e.g. sodium hydride, or potassium fluoride on aluminium, and an alkylating reagent of formula XII, wherein X; is a leaving group, for example halogen, e.g. iodine, bromine or especially chlorine, Ras0S0,0-, CH3S0,0- or

EP . The reaction is preferably carried out in a solvent, for example an amide, e.g. N,N-dimethylformamide (DMF), a sulfoxide, e.g. dimethyl sulfoxide (DMSO), or a nitrile, e.g. acetonitrile. The ketene thioacetal of formula XIV formed is cyclised using hydroxylamine hydrochloride in the presence of a base, for example sodium acetate, in a solvent, for example an alcohol, e.g. ethanol, or an ether, e.g. tetrahydrofuran, to form the . compound of formula le wherein Z is S-. The cyclisation reaction is carried out at , temperatures of from 0°C to 100°C. The compound of formula fe (Z=S) may optionally be oxidised in a manner analogous to standard procedures, for example using peracids, e.g. ’ meta-chloroperbenzoic acid (m-CPBA) or peracetic acid, to form the corresponding sulfones and sulfoxides of formula le (Z = SO- or SO,-), wherein the degree of oxidation at the sulfur atom (Z = SO- or SO;-) can be controlled by the amount of oxidising agent.

. Oxidation to the compound of formula fe (Z = SO- or SO,-) is carried out as described, for example, in H. O. House, "Modern Synthetic Reactions” W. A. Benjamin, Inc., Menlo Park, . California, 1972, pages 334-335 and 353-354.

The activated carboxylic acid derivatives of formula Il in Reaction Scheme 1 (route a), wherein X is a leaving group, for example halogen, e.g. bromine, iodine or especially chlorine, can be prepared in accordance with known standard procedures, for example as described in C. Ferri "Reaktionen der organischen Synthese", Georg Thieme Verlag,

Stuttgart, 1978, page 461 ff and as shown in the following Reaction Scheme 3.

Reaction Scheme 3 o 0 (R)m oH (Rm X of jv DMF at, Ql W,-X, DMF x _— N

N 20-150°C x 11

According to Reaction Scheme 3, preparation of the compounds of formula li (X = leaving group) or Il (X = halogen) is carried out, for example, by using a halogenating agent, for example a thionyl halide, e.g. thionyl chloride or bromide; a phosphorus halide or : phosphorus oxyhalide, e.g. phosphorus pentachloride or phosphorus oxychloride or phosphorus pentabromide or phosphoryl bromide; or an oxalyl halide, e.g. oxalyl chloride, or by using a reagent for the formation of an activated ester for example N,N’-dicyclohexyl- carbodiimide (DCC) or N-ethyl-N’-(3-dimethylaminopropyl)carbodiimide (EDC) of formula X.

In the compound of formula X, as a halogenating agent, X, for example, is a leaving group, for example halogen, e.g. fluorine, bromine or iodine and especially chlorine, and W; is, for example, PCl,, SOCI, SOBr or CICOCO. o The procedure is optionally carried out in an inert, organic solvent, for example in an aliphatic, halogenated aliphatic, aromatic or halogenated aromatic hydrocarbon, e.g. n- » hexane, benzene, toluene, xylenes, dichloromethane, 1,2-dichloroethane or chlorobenzene, at reaction temperatures in the range from -20°C to the reflux temperature of the reaction mixture, preferably at from 40 to 150°C, and in the presence of a catalytic amount of N,N-

dimethylformamide. Such reactions are generally known and described in the literature in a ) number of variants with respect to the leaving group X. . The compounds of formulae lil, IV, V and VI are known and can be prepared in an analogous manner to that described, for example, in WO 92/07837, DE 3 818 958,

EP 338 992 and DE 3 902 818.

The compounds of formula Xil in Reaction Scheme 2 can be obtained by standard procedures, for example from the corresponding compounds of formula Il 0 :

X

(nm,

N

(R) m wherein R and m are as defined for formula | and X is a leaving group, for example halogen, for example via Claisen condensation, or from the compounds of formula If by reaction with a ketocarboxylic acid salt of formula XV £00" M+

H,C XV),

EN (XV)

COR,, wherein Rgs is as defined for formula | and M" is an alkali metal ion (cf., for example,

WO 96/26192).

The compounds of formulae I and XI are known and can be prepared in an analogous manner to that described, for example, in WO 97/46530, Heterocycles, 48, 779 (1998),

Heterocycles, 46, 129 (1997) or Tetrahedron Letters, 1749 (1998).

For the preparation of all further compounds of formula I functionalised according to the ’ definition of (R)m, a large number of known standard procedures, for example alkylation, halogenation, acylation, amidation, oximation, oxidation and reduction, are available, the choice of a suitable preparation procedure being governed by the properties (reactivities) of the substituents in the respective intermediates. Examples of such reactions are given in . All further compounds falling within the scope of formula | can be prepared by simple means, taking into account the chemical properties of the pyridyl and Q moieties.

The end products of formula | can be isolated in customary manner by concentration or evaporation of the solvent and can be purified by recrystallisation or trituration of the solid residue in solvents in which they are not readily soluble, such as ethers, aromatic hydro- carbons or chlorinated hydrocarbons, by distillation or by means of column chromatography and a suitable eluant.

Furthermore, the person skilled in the art will be familiar with the sequence in which certain reactions should advantageously be performed in order to avoid possible subsidiary reactions.

Where synthesis is not directed at the isolation of pure isomers, the product may be in the form of a mixture of two or more isomers. The isomers can be separated according to methods known per se.

Preparation Examples:

Example P1: Preparation of 4-hydroxy-3-(2-methyl-6-triflucromethyl-pyridine-3-carbonyl)- bicyclo[3.2.1]oct-3-en-2-one: 6.68 g (0.0305 mol) of 2-methyl-6-trifluoromethyl-nicotinic acid methyl ester (prepared in the manner described in Heterocycles, 46, 129 (1997)) are dissolved in 250 ml of methanol/- water (3:1 mixture) and 1.92 g (0.046 mol) of lithium hydroxide hydrate are added in portions at 22°C. After 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 with sodium sulfate and concentrated by evaporation, and the residue is triturated with a small amount of hexane. After filtering, 5.69 g (90 % of theory) of the expected 2-methyl-6-trifluoromethyl- v nicotinic acid having a melting point of 147-149°C are obtained.

The 2-methyl-6-trifluoromethyl-nicotinic acid (2.0 g, 0.0098 mol) obtained is dissolved in ’ 20 ml of oxalyl chloride. Three drops of dimethylformamide are added and the mixture is refluxed for 1 hour. The mixture is then concentrated using a rotary evaporator and the residue (2-methyl-6-trifluoromethyl-nicotinoyl chloride) is taken up in 30 ml of methylene chloride. At 0°C, 2.7 mi (0.0196 mol) of triethylamine and 0.12 g (0.00098 mol) of dimethyl- o aminopyridine are added, and then 1.49 g (0.0108 mol) of bicyclo[3.2.1]oct-2,4-dione, dissolved in 20 mi of methylene chloride, are added dropwise. After 3 hours at 22°C, the

R reaction mixture is extracted by shaking with 2N hydrochloric acid. The separated methylene chloride phase is washed with water and then extracted by shaking with 10 % aqueous sodium bicarbonate solution, dried over sodium sulfate and concentrated by evaporation. 3.18 g (100 % of theory) of 2-methyl-6-trifluoromethyl-nicotinic acid 4-oxo-bicyclo[3.2.1]oct-2- en-2-yl ester are obtained in the form of an oil, which can be used further without purification. 3.02 g (0.0093 mol) of methyl-6-trifluoromethyl-nicotinic acid 4-oxo-bicyclo[3.2.1]oct-2-en-2- yl ester and 1.9 ml (0.0136 mol) of triethylamine are dissolved in 45 ml of acetonitrile. At 22°C, 0.01 ml of acetone cyanohydrin is added. After 18 hours at 22°C, the reaction mixture is poured onto a mixture of water and 2N hydrochloric acid and extracted by shaking with ethyl acetate. The ethyl acetate phase is washed with water and then with brine, dried over sodium sulfate and concentrated by evaporation, and the residue is dissolved in a small amount of warm acetone. On being left to stand, the product crystallises out. After filtering, 0.99 g (33 % of theory) of the expected 4-hydroxy-3-(2-methyl-6-trifluoromethyl-pyridine-3- carbonyl)-bicyclo[3.2.1]oct-3-en-2-one is obtained in the form of white crystals (m.p. 75- 77°C).

Example P2: (5-Cyclopropyl-3-methylsulfanyl-isoxazol-4-yh)-(2-methyl-6-trifluoromethyl- : pyridin-3-yl)-methanone: 14.8 g (0.080 mol) of 3-cyclopropyl-3-oxo-propionic acid tert-butyl ester are dissolved in 25 ml of MeOH and 1.93 g (0.080 mol) of magnesium are added. 7 ml of carbon tetrachloride are added dropwise while cooling in an ice bath and the reaction mixture is stirred at 22°C for 1 hour to complete the reaction. After concentrating by evaporation, the residue is suspended in 100 ml of acetonitrile and, at 22°C, 16.31 g (0.073 mol) of 2-methyl- 6-trifluoromethyl-nicotinoyl chloride (prepared in the manner described in Example P1), ~ dissolved in 50 mi of acetonitrile, are added dropwise. After 6 hours, the reaction mixture is taken up in ethyl acetate and washed with saturated sodium bicarbonate solution. The ’ separated ethyl acetate phase is washed with water, dried over sodium sulfate and concentrated by evaporation. The residue is dissolved in 160 ml of methylene chloride and mi of trifluoroacetic acid are added dropwise at 22°C. After 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. 17.3 g (88 % of theory) of 1-cyclopropyl-3-(2-methyl-6-trifluoromethyt-pyridin-3- a yl)-propane-1,3-dione are obtained in the form of an oil, which can be used further without purification. @ The 1-cyclopropyl-3-(2-methyl-6-trifluoromethyl-pyridin-3-yl)-propane-1,3-dione (15.0 g, 0.055 mol) obtained is dissolved in 150 ml of dimethylformamide and 50 g of potassium fluoride on an aluminium oxide support (Alox) (0.0055 mol/g, 0.276 mol) are added in portions at 0°C. After 5 minutes, 6.7 g (0.088 mol) of carbon disulfide are added. After 2 hours, 23.6 g (0.166 mol) of methyl iodide are added dropwise and the reaction mixture is heated at 22°C. After 2 hours the Alox is filtered off, the filtrate is poured into water and extracted by shaking with ethyl acetate. 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 (eluant: ethyl acetate/hexane 15/1). 12.0 g (60 % of theory) of 2-(bis-methylsulfanyl-methylene)-1-cyclopropyl-3-(2-methyl-6-trifluoromethyl-pyridin-3-yl)- propane-1,3-dione are obtained in the form of a solid substance. 12.0 g (0.033 mol) of the product obtained are suspended in 120 ml of ethanol together with 5.4 g (0.066 mol) of anhydrous sodium acetate. 4.6 g (0.066 mol) of hydroxylamine hydro- chloride are added and the batch is reacted at 22°C for 5 hours. A further 2.7 g of anhydrous sodium acetate and 2.3 g of hydroxylamine hydrochloride are then added. After 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. On triturating with a small amount of ethyl acetate, 9.0 g (79.5 %) of the desired product are obtained in the form of white crystals (m.p. 103-104°C).

Example P3: (5-Cyclopropyl-3-methylsulfinyl-isoxazol-4-yl)-(2-methyl-6-trifluoromethyi- pyridin-3-yl}-methanone 1.50 g (0.0043 mol) of (5-cyclopropyl-3-methylsulfanyl-isoxazol-4-yl)-(2-methyl-6-trifluoro- methyl-pyridin-3-yl)-methanone are dissolved in 30 mi of acetone/water (2:1 mixture) and 1.02 g (0.0048 mol) of sodium metaperiodate are added in portions at 22°C. After 5 hours, the reaction mixture is concentrated by evaporation using a rotary evaporator. The residue is ’ taken up 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 (eluant: ethyl acetate/hexane 3/1). 0.8 g (51 %) of the desired product is obtained in the form of white crystals (m.p. 96-97°C).

Example P4: Preparation of 3-hydroxy-4,4-dimethyl-2-(2-methyl-6-trifluoromethyl-pyridine-3- carbonyl)-cyclohex-2-enone (A2-B24): i 6.68 g (0.0305 mol) of 2-methyl-6-trifluoromethyl-nicotinic acid methyl ester (prepared in the manner described in Heterocycles, 46, 129 (1997)) are dissolved in 250 ml of methanol/- ’ water (3:1 mixture) and 1.92 g (0.046 mol) of lithium hydroxide hydrate are added in portions at a temperature of 22°C. After 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, and the residue is triturated with a - small amount of hexane. After filtering, 5.69 g (90 % of theory) of the expected 2-methyl-6- trifluoromethyl-nicotinic acid having a melting point of 147-149°C are obtained.

The 2-methyl-6-trifluoromethyl-nicotinic acid (1.026 g, 0.005 mol) obtained is dissolved in mi of oxalyl chloride. Three drops of dimethylformamide are added and the mixture is refluxed for 1 hour. The mixture is then concentrated by evaporation using a rotary evaporator and the residue (2-methyl-6-trifluoromethyl-nicotinoy! chloride) is taken up in 100 ml of methylene chloride. At a temperature of 0°C, 1.6 ml (0.0115 mol) of triethylamine and 0.7 g (0.005 mol) 4,4-dimethyl-cyclohexane-1,3-dione are added. After 2 hours at a temperature of 22°C, the solvent is removed using a vacuum rotary evaporator, the residue that remains is dissolved in 55 mi of acetonitrile and, for rearrangement of the intermediate, 0.15 ml (0.0016 mol) 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 syrup that remains is chromatographed on silica gel. The light-yellow, viscous oil obtained by eluting with a mixture of toluene, ethyl alcohol, dioxane, triethylamine and water (100:40:20:20:5 parts by volume) (Rf = 0.39 based on the said mixture as mobile phase) is dissolved in dichloromethane and washed with 75 mi of hydrochloric acid 5 % and 75 mi of water in succession. After drying the organic solution with Na,SQ,, concentration by evaporation yields 1.05 g (63 %) of pure title compound. 'H NMR (ds-DMSO, § in ppm): 1.342, s, 6H: 2.088, t, J 9Hz, 2H: 2.685, s,3H: 2.982, 1, J 9Hz, 2H:8.030, d, J 8.1Hz, IH: 8.094, d, J 8.1Hz, 1H.

Example P5: Preparation of 5-methyl-5-trifluoromethyl-cyclohexane-1,3-dione (Example : B1066): 0.64 g of sodium is introduced into 40 m| of ethanol, 3.23 ml of acetic acid methyl ester and 4.9 g of 4,4 ,4-trifluoro-3-methyl-but-2-enoic acid isopropyl ester are incorporated and the mixture is heated at boiling temperature for 18 hours. After extraction with dilute hydrochloric

W acid against ethyl acetate, concentration by evaporation is carried out. The non-purified 2- methyl-4,6-dioxo-2-trifluoromethyl-cyclohexanecarboxylic acid methyl ester that remains ¢ behind is esterified in the presence of 9.1 g of sodium hydroxide in a mixture of methanol and water at boiling temperature. The mixture is then acidified with hydrochloric acid and extracted with fresh ethyl acetate. After recrystallisation (ethyl acetate), pure 5-methyl-5- trifluoromethyl-cyclohexane-1,3-dione having a melting point of 150-152°C is obtained.

Example P6: Preparation of 2-hydroxy-1-methoxy-5-methyl-4-oxo-cyclohex-2-enecarboxylic acid methyl ester (B1069):

A 30 % solution of 35.8 g of sodium methanolate is made up in 65 ml of dimethyl sulfoxide and, over a period of 20 minutes, is treated at a temperature of from 30 to 35°C with a mixture of 16.7 g of 3-methyl-3-buten-2-one and 32.4 g of methoxymalonic acid dimethyl ester. The mixture is stirred for 1 hour at a temperature of 35°C, acidified with hydrochloric acid and then extracted several times with dichloromethane. The organic phases are washed with water, dried and concentrated. By crystallising from hot ethyl acetate and hexane, pure 2-hydroxy-1-methoxy-5-methyl-4-oxo-cyclohex-2-enecarboxylic acid methyl ester having a melting point of 117-117.5°C is obtained.

Example P7: Preparation of 2-hydroxy-1-methoxy-5-methyl-3-(2-methyl-6-trifluoromethyl- pyridine-3-carbonvyl)-4-oxo-cyclohex-2-ene-carboxylic acid methyl ester (A2-B1069): 2.23 g of fresh 2-methyl-6-trifluoromethyl-nicotinoyl chloride are added to a mixture of 2.14 g of 2-hydroxy-1-methoxy-5-methyl-4-oxo-cyclohex-2-ene-carboxylic acid methyl ester and 2.02 g of triethylamine in 30 ml of acetonitrile. After about 30 minutes, 0.065 g of potassium cyanide is added and the batch is stirred for 18 hours. The batch is then extracted at pH 2 with water against ethyl acetate, dried over magnesium sulfate and concentrated by evaporation. By filtering over silica gel (mobile phase: ethyl acetate/methanol/triethylamine 85:10:5), pure 2-hydroxy-1-methoxy-5-methyl-3-(2-methyl-6-trifluoromethyl-pyridine-3- carbonyl)-4-oxo-cyclohex-2-enecarboxylic acid methyl ester is obtained in the form of a : viscous oil.

Example P8: Preparation of 3-hydroxy-4-methoxy-6-methyl-2-(2-methyl-6-trifluoromethyl- . pyridine-3-carbonyl)-cyclohex-2-enone (A2-B1070): 0.586 g of potassium hydroxide is added to 1.4 g of 2-hydroxy-1-methoxy-5-methyl-3-(2- . methyl-6-trifluoromethyl-pyridine-3-carbonyl)-4-oxo-cyclohex-2-enecarboxylic acid methyl ester in dioxane/water (5:3) and the batch is stirred for 3 hours. The batch is then acidified (pH 3) and extracted with fresh ethyl acetate. The crude product is purified by chromato- graphy analogously to Example P7. 3-Hydroxy-4-methoxy-6-methyl-2-(2-methyl-6-trifluoro- methyl-pyridine-3-carbonyl)-cyclohex-2-enone is obtained in the form of a viscous oil (as a mixture of 3 tautomeric forms, according to 'H-NMR).

The compounds listed in the following Tables can also be prepared in an analogous manner and using methods described in the general Reaction Schemes 1 and 2 and in the references mentioned therein. In the following Tables Ph is the phenyl group and CC is an ethyne group.

Table 1: Compounds of formula Ib:

R, O 0

R, (Ib)

Nd

R 76 R 2 0

Compd. Rs R 7 R~ Rs m.p. (°C) no. 1.001 CH, CF; H H 75-77 1.002 CH;CH; CF; H " H 1.003 (CHa3).CH CF; H H 111-112 1.004 CH;(CH.)s CF; H H 1.005 Ph CF; H H oil 1.006 CH,Br CFs H H } 1.007 ‘CH,OCH; CF; H - H 124-126 1.008 CH,SMe CF; H H oil 1.009 CH.SO.Me CF; H H 55-55 1.010 SCH; CF; H H

Compd.

Rs R 7 R# Rs m.p. (°C) © no. 1.011 SOCH,4 CF; H H . 1.012 SO.CH; CF; H H © 1.013 SPh CF, H H 1.014 SOPh CF; H H 1.015 SO,Ph CF, H H 1.016 CH CFiCF, H H 1.017 CH;CH, CF;CF.

H H 1.018 (CH3),CH CF4CF, H H 1.019 CHs(CHb)s CF:CF.

H H 1.020 Ph CF4CF» H H 1.021 CH,Br CF4CF, H H 1.022 CH,OCHs CF,CF, H H 1.023 CH,SMe CF4CF; H H 1.024 CH,SOMe CF:CF, H H 1.025 SCH, CF4CF» H H 1.026 SOCH, CFsCF; H H 1.027 SO,CH;, CF4CF, H H 1.028 SPh CF.CF, H H 1.029 SOPh CF:CF, H H 1.030 SO,Ph CF4CF, H H 1.031 CH; CHF, H H 1.032 CH4CH; CHF; H H 1.033 (CH,),CH CHF; H H 1.034 CHa(CHo)s CHF, H H : 1.035 Ph CHF; H H 1.036 CH,Br CHF, H H 1.037 CH,OCH; CHF, H H : 1.038 CH.SMe CHF, H H 1.039 CH,SO,Me CHF, H H ’ 1.040 SCH; CHF, H H 1.041 SOCH; CHF, H H 1.042 SO.CHj CHF, H H

ET

Compd. Rs R 7 R Rs m.p. (°C) o no. 1.043 SPh CHF, H H . 1.044 SOPh CHF» H H 1.045 SO,Ph CHF, H H 1.046 CH CFs CH H 1.047 CHyCH, CF, CH; H 1.048 (CH3).CH CF, CH; H 1.049 CH3(CHy)s CF, CH; H 1.050 Ph CF; CHa H 1.051 CH,Br CFs CH; H 1.052 CH-OCH;, CFs CH H 1.053 CH,SMe CF, CH; H 1.054 CH,SOMe CFs CH, H 1.055 SCH CFs CHa H 1.056 SOCH; CF, CH H 1.057 SO,CHs CFs CHs H 1.058 SPh CF, CH, H 1.059 SOPh CF, CH, H 1.060 SO,Ph CF, CH H 1.061 CHa CFCF» CH, H 1.062 CHsCH; CFiCF» CHa H 1.063 (CHa3).CH CFsCF, CHa H 1.064 CHa(CHy)s CFiCF, CHa H 1.065 Ph CF,.CF» CHa H 1.066 CH,Br CFsCF» CHa H 1.067 CH,OCHs CF,CF, CHs H 1.068 CH.SMe CF,CF» CHa H 1.069 CH,SO,Me CFsCF, CHa H : 1.070 SCH; CF.CF, CHa H 1.071 SOCH; CF,CF, CH, H ’ 1.072 SO,CHjs CF, CF, CH, H 1.073 SPh CFsCF, CHa H 1.074 SOPh CF,.CF, CH, H

Compd.

Rs Rs R 7 Rs m.p. (°C)

a no.

1.075 ~~ SO.Ph CFCF, CH, H o 1.076 CH CHF, CH, H

1.077 CH4CH; CHF, CH, H

1.078 (CH,),CH CHF, CH, H 1.079 CHs(CH>)s CHF, CH, H

1.080 Ph CHF, CH, H

1.081 CH.Br CHF, CH, H

1.082 CH,OCH; CHF, CHa H

1.083 CH.SMe CHF.

CHa H

1.084 CH,SO.Me CHF, CH, H

1.085 SCH; CHF.

CHa H

1.086 SOCH; CHF.

CH H

1.087 SO.CHj CHF.

CHs H

1.088 SPh CHF, CH, H

1.089 SOPh CHF, CH H

1.090 SO,Ph CHF, CHa H

1.091 CHa CFs H CH, 92-94

1.092 CH5CH; CF; H CH,

1.093 (CHa).CH CFs H CH,

1.094 CH3(CHo)s CFs H CHa,

1.095 Ph CFs H CH,

1.096 CH.Br CFs H CH,

1.097 CH,OCH; CFs H CH,

1.098 CH.SMe CF, H CH,

1.099 CH,SO.Me CFs H CH,

1.100 SCH; CFs H CH;

1.101 SOCH, CFs H CH, ) 1.102 SO,CHs CFs H CH,

1.103 SPh CF, H CH, ; 1.104 SOPh CF, H CHs

1.105 SO,Ph CF, H CH,

Table 2: Compounds of formula lc: i R, O ©O cr, 3 (le)

R NT n° 76 R ®)

CHj

Compd. Rs R 7 R Rs m.p.(°C) no. 2.001 CH; CF; H H 107-109 2.002 CHyCH; CFs H H oil 2.003 (CH3),CH CF; H H oil 2.004 CH3(CHb)s CF H H 2.005 Ph CF; H H oil 2.006 CH.Br CF; H H 2.007 CH,OCH; CF, H H 2.008 CH,SMe CF; H H 2.009 CH,SO.Me. CF; H H 2.010 SCH; CF3 H H 2.011 SOCH; CF; H H 2.012 SO.CHjs CFs H H 2.013 SPh CFs H H 2.014 SOPh CFs HH H : 2.015 SO,Ph CF, H H 2.016 CH, CF,CF. H H 2.017 CHzCH; CF4CF. H H ' 2.018 (CHs),CH CF.CF. H H 2.019 CHs(CHz)s CFiCF» H H 2.020 Ph CFCF. H H 2.021 CH,Br CF4CF. H H 2.022 CH,OCH; CF.CF; H H

Compd.

Rs R 7 R Rs m.p.(°C)

a no. 2.023 CH,SMe CF:CF, H H

. 2.024 CH,SO.Me GF,CF, H H 2.025 SCH; CF:CF, H H 2.026 SOCH; CF:CF> H H 2.027 SO,CHs CF:CF, H H 2.028 SPh CF4sCF, H H 2.029 SOPh CF:CF, H H 2.030 SO,Ph CF:CF, H H

2.031 CHa CHF, H H 2.032 CH4CH; CHF, H H 2.033 (CHa)-CH CHF, H H 2.034 CHs(CHo)s CHF, H H 2.035 Ph CHF, H H : 2.036 CH.Br CHF, H H 2.037 CH,OCH; CHF, H H 2.038 CH,SMe CHF.

H H 2.039 CH,SOMe CHF, H H 2.040 SCH; CHF, H H 2.041 SOCH; CHF, H H 2.042 SO,CHs CHF, H H 2.043 SPh CHF, H H 2.044 SOPh CHF, H H 2.045 SO,Ph CHF, H H 2.046 CHs CFs CHs H 2.047 CH4CH; CF, CHa H 2.048 (CHa)oCH CF CH H

2.049 CHa(CHy)s CFs CHa H

: 2.050 Ph "CF, CHa H 2.051 CH,Br CF, CHa H

2.052 CH,OCH; CFs CHa H 2.053 CH,SMe CF CH H 2.054 CH,SO;Me CF, CH; H

Claims (16)

1. What is claimed is:

   “ 1. A herbicidally selective composition that, in addition to comprising customary inert formulation adjuvants, comprises as active ingredient a mixture N a) a herbicidally effective amount of a compound of formula 0) Q (1, N (R) m wherein each R is independently hydrogen, C,-Cgalkyl, Co-Cealkenyl, Co-Cghaloalkenyl, C»-Cealkynyl, Co-Cghaloalkynyl, Cs-Cecycloalkyl, C;-Csalkoxy, Ci-Cshaloalkoxy, Cs- Cealkylthio, C,-Cealkylsulfinyl, C;-Cealkylsulfonyl, C,-Cghaloalkyl, C,-Cghaloalkylthio, C;- Cehaloalkylsulfinyl, C;-Cshaloalkylsulfonyl, C,-Cgalkoxycarbonyl, C;-Csalkylcarbonyl, C;- Cealkylamino, di(C4-Csalkyl)amino, C,-Cgalkylaminosulifonyl, di(C;-Cgalkyl)aminosulfonyl, - N(R4)-S-R;, -N(R3)-SO-R4, -N(Rs)-SO,-Rs, nitro, cyano, halogen, hydroxy, amino, benzylithio, : benzylsulfinyl, benzyisuifonyl, phenyl, phenoxy, phenyithio, phenyisulfinyl or phenylsulfonyt; wherein the phenyl group may itself be mono-, di- or tri-substituted by C;-Cealkyl, C;-Cghalo- alkyl, C3-Cgalkenyl, Cs-Cghaloalkenyl, Cs-Cgalkynyl, Cs-Cghaloalkynyl, C;-Csalkoxy, C;- Cshaloalkoxy, Cs-Cealkenyloxy, Cs-Cealkynyloxy, mercapto, C,-Cealkylthio, Cs- Cghaloalkylthio, C4-Cealkenylthio, Co-Cehaloalkenylthio, Cs-Cgalkynylthio, Cp Csalkoxyalkylthio, Cs-Csacetylalkylthio, Cs-Cealkoxycarbonylalkylthio, C»-Cscyanoalkyithio, C;-Cealkylsulfinyl, C,-Cghaloalkylsulfinyl, C,-Csalkylsuifonyl, C,-Cshaloalkylsulfonyl, aminosulfonyl, C;-Czalkylaminosulfonyl, C,-C,dialkylaminosulfonyl, C,-Csalkylene-R;s, NRsR47, halogen, cyano, nitro, phenyl or by benzylthio, wherein the latter phenyl and benzylthio groups may themselves be substituted on the phenyl ring by C,-Cjalkyl, C;- Cshaloalkyl, C4-Csalkoxy, C4-Cshaloalkoxy, halogen, cyano or by nitro; . or each R is independently a monocyclic or fused bicyclic ring system having from 5 to 10 members, which may be aromatic or partially saturated and may contain from 1 to 4 hetero 6 atoms selected from nitrogen, oxygen and sulfur; wherein the ring system either is bound directly to the pyridine ring or is bound to the pyridine ring via a C4-C,alkylene group, and each ring system may not contain more than two oxygen atoms and may not contain more than two sulfur atoms, and the ring system may itself be mono-, di- or tri-substituted by

   Ci-Cealkyl, C;-Cghaloalkyl, Cs-Cealkenyl, Cs-Cghaloalkenyl, Cs-Csalkynyl, Cs-Cghaloalkynyl,

   . C1-Cealkoxy, C,-Cghaloalkoxy, Ca-Cealkenyloxy, Cs-Csalkynyloxy, mercapto, C,-Cealkyithio, Cs-Cghaloalkylthio, Cs-Csalkenylthio, C3-Cghaloalkenyithio, Cs-Cealkynylthio, Co-Csalkoxy- - alkylthio, Cs-Csacetylalkylthio, C3-Cealkoxycarbonylalkylthio, Co-Cscyanoalkylthio, C;-Csalkyl- sulfinyl, Cs-Gghaloalkylsulfinyl, C4-Cealkylsulfonyl, C;-Cghaloalkylsulfonyl, aminosulfonyl, C;-Caalkylaminosulfonyl, C,-C,dialkylaminosulfonyl, C,-Caalkylene-R;, NRgR,, halogen, cyano, nitro, phenyl or by benzylthio, wherein phenyl and benzylthio may themselves be substituted on the phenyl ring by C;-Csalkyl, C,-Cshaloalkyl, C;-Csalkoxy, C4-Cshaloalkoxy, halogen, cyano or by nitro, and wherein the substituents on the nitrogen in the heterocyclic ring are other than halogen; or each R is independently C,-C,alkoxy-C;-Caalkyl or C4~-C,alkoxy-C,-Caalkoxy-C4-C,alkyl; mis 1,2,3o0r4, Ri, Rs and Rs are each independently of the others hydrogen or Cy-Cgalkyl; R: is NRoR11, C4-Cgalkoxy, C,y-Cghaloalkoxy, C;-Cealkyl, C;-Cghaloalkyl, Cs-Cealkenyl, C3-Ce- haloalkenyl, C;-Cealkynyl, C3-Cshaloalkynyl, C3-Cecycloalkyl or phenyl, wherein phenyl may itself be substituted by C,-Cjalkyl, C;-Cshaloalkyl, C4-Caalkoxy, Ci-Cshaloalkoxy, halogen, cyano or by nitro; : Rs is NR12R3, Cy-Cealkoxy, C,-Cghaloalkoxy, Cy-Csalkyl, C4-Cshaloalkyl, Cs-Cealkenyl, Cs-Cg- haloalkenyl, Cs-Cesalkynyl, Cs-Cghaloalkynyl, C;-Cecycloalkyl or phenyl, wherein phenyl may itself be substituted by C;-Cjalkyl, C;-Cshaloalkyl, C4-Csalkoxy, C;-Cshaloalkoxy, halogen, cyano or by nitro; Rg is NRy4Ris5, C1-Cgalkoxy, C,-Cghaloalkoxy, Cy-Cealkyl, C;-Cshaloalkyl, Cs-Cealkenyl, C;-Cs- haloalkenyl, C3-Csalkynyl, Cs-Cshaloalkynyl, Cs-Cscycloalkyl or phenyl, wherein phenyl may itself be substituted by C4-Csalkyl, C4-Cshaloalkyl, C4-Cgalkoxy, Ci-Cshaloalkoxy, halogen, cyano or by nitro; R; and Rs are each independently of the other C;-Caalkoxy, C,-Cjalkoxycarbonyl, Ci-Cs- alkylthio, C4-Caalkylsulfinyl, C,-Csalkylsulfonyi or phenyl, wherein phenyl may itself be ‘ substituted by C;-Csalkyl, C;-Cshaloalkyl, C,-Csalkoxy, C,-Cshaloalkoxy, halogen, cyano or by nitro; ; Rs, Rio, Riz, Ris and Rye are each independently of the others hydrogen or C,-Cealkyl; Re, R11, Ris, Ris and Ry; are each independently of the others C;-Csalkyl or C;-Cealkoxy; ‘ Q is the group Q4

   0) “ R 16 " “R 18 R o v wherein Ry, R17, Rig and Ryg are each independently of the others hydrogen, hydroxy, C,-Caalkyl, Co-Csalkenyl, Co-Cealkynyl, C4-Cgalkoxycarbonyl, C4-Csalkylthio, C,- Cealkylsulfinyl, C,-Cgalkylsulfonyl, C;-Cjalkyl-NHS(O),, C;-Cshaloalkyl, -NH-C,-C,alkyl, - N(C;-Caalkyl),, C4-Cgalkoxy, cyano, nitro, halogen, or phenyl which may itself be substituted by C;-Caalkyl, C;-C,haloalkyl, C;-C,alkoxy, C;-Cshaloalkoxy, Cs-Caalkylcarbonyl, C;- Caalkoxycarbonyl, amino, C4-Csalkylamino, di(C,-Cjalkyl)amino, C4-Cgalkylthio, C4- Cealkylsulfinyl, Ci-Cealkylsulfonyl, C4-Caalkyl-S(0)20, C4-Cshaloalkylthio, C- Cshaloalkylsulfinyi, C4-Cjhaloalkylsulfonyl, C,-Cjhaloalkyl-S(0O),0, C4-Caalkyl-S(O).NH, C,- Caalkyl-S(O).N(C;-Caalkyl), halogen, nitro, COOH or by cyano; or two adjacent substituents out of Rye, R17, Rig and Ryo form a C,-Cgalkylene bridge; Raz is hydroxy, O'M", halogen, C;-Czalkoxy, C,-Cyzalkylcarbonyloxy, Co-Caalkenylcarbonyil- oxy, Cs-Cecycloalkylcarbonyloxy, C,-Czalkoxycarbonyloxy, C,-Cizalkylcarbonyloxy, R2;R2:N-C(0)0, C,-Cy.alkylthio, C4-Cyaalkylsulfinyl, C4-Cyoalkylsulfonyl, C,-Cshaloalkylthio, C,-C;haloalkylsulfinyl, C;-C;haloalkylsulfonyl, C,-Cizalkenylthio, C,-Cizalkenylsulfinyl, Co-C,.- alkenylsulfonyl, Co-Cizhaloalkenylthio, Co-Cyzhaloalkenylsulfinyl, C,-Cqohaloalkenylsulfonyl,

   C.-C, zalkynyithio, C.-Cyzalkynylsuifinyl, Co-Cizalkynylsulfonyl, G,-Cjalkyl-S(0),0, phenyl-S(0),0, (C;-Cjalkoxy).P(0)O, C,-C,alkyl(C4-Caalkoxy)P(O)O, H(C4-C,alkoxy)P(O)O, C;-Cy2-alkyl-S(CO)0, benzyloxy, phenoxy, phenyithio, phenylsuifinyl or phenylsulfonyl, wherein the phenyl group may itself be substituted by C;-C,alkyl, C4-Cjhaloalkyl, C,- Caalkoxy, Cs-Cshaloalkoxy, C4-Cjalkylcarbonyl, C,-Caalkoxycarbonyl, C,-Cjalkylamino, di(C4- C,alkyl)amino, C4-C,alkylthio, Cs-C,alkylsulfinyl, C1-Caalkylsulfonyl, C;-Cjalkyl-S(0).0, C;- C,haloalkylthio, C4-Cjhaloalkylsulfinyl, C;-Chaloalkylsulfonyl, C,-Cshaloalkyl-S(O).0, C;- C,alkyl-S(O).NH, C4-Csalkyl-S(O)oN(C,-C,alkyl), halogen, nitro or by cyano; and

   R., and Ry, are each independently of the other hydrogen or C;-Cjalkyl; or is the group Qo IN R 23 7) (Qa),

   Fo wherein Ra; is hydroxy, OM, halogen, C;-Cy.alkoxy, C,-Cqzalkylcarbonyloxy, Co-Ca- o alkenylcarbonyloxy, Cs-Cecycloalkylcarbonyloxy, C4-Cizalkoxycarbonyloxy, C;-Cizalkyl- carbonyloxy, RzsR2sN-C(0)0, Ci-Cyaalkyhthio, C;-Cyzalkylsulfinyl, C4-Cyzalkylsulfonyl, N C:-Cshaloalkyithio, C4-Cshaloalkylsulfinyl, C,-Cshaloalkylsulfonyl, C,-Cizalkenylthio, Co-Cy2- alkenylsulfinyl, C,-Cyzalkenylsulfonyl, Co-Czhaloalkenylthio, C,-Cizhaloalkenylsulfinyl, Co-Cqz- haloalkenylsulfonyl, C,-Calkynyithio, C.-Czalkynylsulfinyl, Co-Cszalkynylsulfonyl, C,-Cy- alkyl-S(0),0, phenyl-S(0).0, (C;-Caalkoxy).P(0)O, C-Cjalkyl(C:-Caalkoxy)P(O)0O, H(C4-C,alkoxy)P(0O)O, C4-Cy2-alkyl-S(CO)O, benzyloxy, phenoxy, phenylthio, phenylisulfinyl or phenylsulfonyl, wherein the phenyl group may itself be substituted by C4-Cjalkyl, Cs- Cshaloalkyl, C4-C,alkoxy, C4-Cshaloalkoxy, C4-Cjalkylcarbonyl, C4-Cjalkoxycarbonyl, Cs- Caalkylamino, di(C;-C,alkyl)amino, C;-Csalkylthio, C4-Cjalkylsulfinyl, C;-Caalkylsulfonyl, C;-Caalkyl-S(0),0, C4-Cshaloalkylthio, Cq-Cshaloalkylsulfinyl, C;-Cshaloalkylsulfonyl, C4-Cshaloalkyl-S(0),0, C,-Chalkyl-S(O).NH, C,-C,alkyl-S(O).N(C4-Cjalkyl), halogen, nitro or by cyano; R24 and Rqs are each independently of the other hydrogen or C;-Cjalkyl; and Y is oxygen, sulfur, a chemical bond or a C,-C,alkylene bridge; or is the group Q3 Xi (Qa), Rye Pas wherein Ra, Ray, Rss and Ryo are each independently of the others hydrogen, C,-Cgalkyl, C,-Cghaloalkyl, C,-Cealkenyl, Co-Cgalkynyl, C4-Cgalkoxycarbonyl, Cs-Cealkylthio, Cy-Cealkyl- sulfinyl, C1-Cealkylsulfonyl, C4-Cealkyl-NHS(O),, C;-Cealkylamino, di(C4-Csalkyl)amino, hydroxy, C1-Cealkoxy, Cs-Cealkenyloxy, Cs-Csalkynyloxy, hydroxy-Cs-Csalkyl, C,-Caalkyl- sulfonyloxy-C;-Csalkyl, tosyloxy-C;-Cgalkyl, halogen, cyano, nitro, phenyl, or phenyl substituted by C4-Cjalkyl, C,-Cshaloalkyl, C4-Cjalkoxy, Ci-Cshaloalkoxy, Cq-Cgalkylcarbonyl,

   . C;-Caalkoxycarbonyl, amino, C;-Cjalkylamino, di(Cs-Casalkyl)amino, C,-Cgalkylthio, C,- Csalkylsulfinyl, C4-Cealkylsulfonyl, C,-Cjalkyl-S(0)20, C;-Cghaloalkyithio, Cs-

   . Cshaloalkylsulfinyl, Cy-Cghaloalkylsulfonyl, C4-Cshaloalkyl-S(0),0, C,-Caalkyl-S(O).NH, C,-. Csalkylthio-N(C4-C,alkyl), Ci-Cealkylsulfinyl-N(C4-Caalkyl), C4-Cealkylsulfonyl-N(C4-Caalkyl), halogen, nitro, COOH or by cyano; or adjacent Rss and Rs; or Rs and Rag together are Cs- Cealkylene;

   W is oxygen, sulfur, sulfinyl, sulfonyl, -CR4;Rz-, -C(O)- or -NRas-; 3 Ray is hydrogen, Cy-Caalkyl, C1-Cyhaloalkyl, Cy-Caalkoxy-Cs-Caalkyl, Cs-Cyalkylthio-Cy- Caalkyl, C;-Caalkylcarbonyloxy-C4-Calkyl, C,-C,alkylsulfonyloxy-C4-Cialkyl, tosyloxy-C4-

   . Caalkyl, di(Cs-Csalkoxyalkyl)methyl, di(C,-Csalkylthioalkyl)methyl, (C4-Caalkoxyalkyl)-(C,- Caalkylthioalkyl)methyl, Cs-Csoxacycloalkyl, Cs-Csthiacycloalkyl, C;-Cydioxacycloalkyl, Cs-

   C.dithiacycloalkyl, C5-Cjoxathiacycloalkyl, formyl, C;-Cialkoxycarbonyl, or phenyl which may itself be substituted by Cy-Caalkyl, C-Cshaloalkyl, Cs-Caalkoxy, Cy-Cshaloalkoxy, Cy- Caalkylcarbonyl, C,-C,alkoxycarbonyl, amino, C;-C,alkylamino, di(C;-Csalkyl)amino, Ci- Caalkylthio, C4-Caalkylsulfinyl, C,-Calkylsulfonyl, C-Cialkyl-S(O),0, C,-Cjhaloalkylthio, Cs- Cahaloalkylsulfinyl, C,-C,haloalkylsulfonyl, C,-Cshaloalkyl-S(0),0, C;-C,alkyl-S(O).NH, C;- Cealkylthio-N(C4-Caalkyl), Ci-Cealkylsulfinyl-N(C4-Cjalkyl), C,-Cealkylsulfonyl-N(C,-C alkyl), halogen, nitro, COOH or by cyano; or Ry, together with Rg, is C;-Cgalkylene; Raz is hydrogen, C,-C,alkyl or C4-C4haloalkyl; Rao is hydroxy, O'M", halogen, C,-C.alkoxy, C,-Cizalkylcarbonyloxy, C,-Cgalkenylcarbonyl- oxy, Cs-Cecycloalkylcarbonyloxy, C4-Cy.alkoxycarbonyloxy, C-Cy.alkylcarbonyloxy, : ResRe7N-C(O)O, C;-Cizalkylthio, C4-Cyqalkylsulfinyl, C4-Cyalkylsulfonyl, C,-Cshaloalkylthio, C4-Chaloalkylsulfinyl, C,-Cshaloalkylsulfonyl, C,-Cyzalkenyithio, C.-Cjralkenylsulfinyl, C,-Cy,- alkenylsulfonyl, C,-C;haloalkenylthio, C.-Cszhaloalkenylsulfinyl, Co-Cizhaloalkenylsulfonyl, C2-Cyzalkynylthio, C,-Czalkynylsulfinyl, C,-Cyzalkynylsulfonyl, C4-Caalkyl-S(0),0, phenyl-S(0).0, (C4-Cjalkoxy).P(0)O, C;-Cialkyl(C:-Caalkoxy)P(O)O, H(C4-Csalkoxy)P(0)0, C+-Ci2-alkyl-S(CQ)O, benzyloxy, phenoxy, phenylthio, phenylsulfinyl or phenylsulfonyi, wherein the phenyl group may itself be substituted by C;-Cjalkyl, Ci-Cshaloalkyl, Ci- Caalkoxy, Ci-Cihaloalkoxy, Ci-Caalkylcarbonyl, C,-Caalkoxycarbonyl, Cs-Cgalkylamino, di(C- Caalkyl)amino, C;-Cjalkylthio, C,-Caalkylsulfinyl, C;-Caalkylsulfonyl, C-Cjalkyl-S(0).0, C,- Cghaloalkylthio, C;-C,haloalkylsulfinyl, C,-Cashaloalkylsulfonyl, C-Cshaloalkyl-S(0),0, C;- Caalkyl-S(O).NH, C,-C,alkyl-S(O),N(C,-C,alkyl), halogen, nitro or by cyano; Rags and Rey are each independently of the other hydrogen or C;-Calkyl; Raz is hydrogen, C,-Caalkyl, C4-Cjalkoxycarbonyl, or phenyl which may itself be substituted by C-Caalkyl, C4-Cshaloalkyl, C,-Cjalkoxy, Cy-Cshaloalkoxy, Cy-Caalkylcarbonyl, Cy- ! Caalkoxycarbonyl, C4-Caalkylamino, di(C4-Caalkyl)amino, C,-Caalkylthio, C,-Cjalkylsulfinyl, Cy-Calkylsulfonyl, C4-C.alkyl-§(0),0, C4-Cshaloalkylthio, C4-Cshaloalkylsulfinyl, C;- } C;shaloalkylsulfonyl, C4-Cshaloalkyl-S(0).0, C;-Cialkyl-S(0).NH, C4-C,alkyl-S(0).N(C,4- C,alkyl), halogen, nitro or by cyano; or is the group Q,

   & Ra (Qu) @ 0) N R 35 wherein Ro hydroxy, O'M?, halogen, C;-Cyzalkoxy, Cs-Cy.alkylcarbonyloxy, Co-Cialkenyi- carbonyloxy, Cs~Cecycloalkylcarbonyloxy, C4-C;zalkoxycarbonyloxy, C4-Cyealkyicarbonyloxy, R31R:2N-C(0)0O, C,-Cjzalkylthio, C4-Cyzalkylsulfinyl, C,-Cszalkylsulfonyl, C,-C,haloalkylthio, C;-Cshaloalkylsulfinyl, C4-Cshaloalkylsulfonyl, C,-Cizalkenylthio, Co-Cyalkenylsulfinyl, Co-Cio- alkenylsulfonyl, C,-Cyohaloalkenylthio, C,-Cishaloalkenylsulfinyl, Co-Ci-haloalkenylsulfonyl, Co-Cizalkynylthio, Co-Cysalkynylsulfinyl, Co-Cyzalkynylsulfonyl, C4-Cialkyl-S(0).0, phenyl-S(0),0, (C4-Caalkoxy).P(0)0O, C;-Caalkyl(C4-Caalkoxy)P(0)O, H(C,-Caalkoxy)P(O)O, C;-Cy2-alkyl-S(CO)O, benzyloxy, phenoxy, phenylthio, phenylisulfinyl or phenylsulfonyl, wherein the phenyl group may itself be substituted by C;-Cjalkyl, C;-Cshaloalkyl, Cs- C,alkoxy, C-Cshaloalkoxy, C4-Cjalkylcarbonyl, C,-Caalkoxycarbonyl, C4-Cjalkylamino, di(C;- Caalkyl)amino, C4-C,alkylthio, C,-C,alkylsulfinyl, C4-Cjalkylsulfonyl, C4-Cjalkyl-S(0),;0, C;- Chaloalkyithio, C4-Cshaloalkylsulfinyl, C;-Cjhaloalkylsulfonyl, C,-Cjhaloalkyl-S(O).0, C;- Caalkyl-S(O)oNH, C4-Caalkyl-S(O).N(C,-Cyalkyl), halogen, nitro or by cyano; and Rs; and Rj, are each independently of the other hydrogen or C,-C,alkyl; Rs; and Rss are each independently of the other hydrogen, hydroxy, C,-C,alkyl, C,-Csalkenyl, C2-Cealkynyl, C,-C,alkoxycarbonyl, C4-Csalkylthio, C;~-Cgalkylsulfiny!, C,-Cgalkylsulfonyl, C;-Caalkyl-NHS(O),, C4-Cjhaloalkyl, -NH-C,-C,alkyl, -N(C,-C,alkyl),, C1-Cgalkoxy, cyano, nitro, halogen, or phenyl which may itself be substituted by C;-C,alkyl, C,-Czhaloalkyl, C4-C,- alkoxy, C;-Cshaloalkoxy, Cy-Caalkylcarbonyl, C4-Caalkoxycarbonyl, amino, C4-Cjalkylamino, di(C4-Cjalkyl)amino, C,-Cgalkylthio, C4-Cealkylsulfinyl, C-Cealkylsulfonyl, C;-C,alkyl-S(0),0, C;-Cshaloalkylthio, C4-Cjhaloalkylsulfinyl, C;-Cshaloalkylsulfonyl, C,-Cjhaloalkyl-S(0),0, C4-Caalkyl-S(0)2NH, C,-C,alkyl-S(0),N(C,-Cjalkyl), halogen, nitro, COOH or by cyano; or R33 and Ra, together form a C,-Cealkylene bridge; and Rss is hydrogen, C4-Caalkyl, C4-Cialkoxycarbonyl, or phenyl which may itself be substituted by C4-Caalkyl, C-C haloalkyl, C,-C alkoxy, C;-Cshaloalkoxy, C,-Cjalkylcarbonyl, C;- w Caalkoxycarbonyl, amino, C,-Calkylamino, di(C,-Csalkyl)amino, C,-C,alkylthio, C,-

   C.alkylsulfinyl, C;-Cgalkylsulfonyl, C;-Cjalkyl-S(0)20, C;-C,haloalkylthio, C;- C;haloalkylsulfinyl, C;-Cshaloalkylsulfonyl, C,-Cshaloalkyl-S(0),0, C4-Caalkyl-S(O).NH, C,- C,alkyl-S(0).N(C;-C,alkyl), halogen, nitro, COOH or by cyano;

   or is the group Qs ) Z-R o1

   . ba! (Qs), Rg 0) wherein Z is sulfur, SO or SO; Ror is hydrogen, C;-Cgalkyl, C4-Cgalkyl substituted by halogen, C,-C,alkoxy, C;-C,alkylthio, C;-Caalkylsuifonyl, C,-C,alkylsulfinyl, hydroxy, cyano, nitro, -CHO, -CO2Rg; , -CORs, -COS8R4, -NRgsRos , CONRgssR037, or by phenyl which may itself be substituted by C;- Caalkyl, C4-Cghaloalkyl, C;-Caalkoxy, C;-Cshaloalkoxy, Cp-Cealkenyl, Cs-Cealkynyl, Ca- Cealkenyloxy, Cs-Cealkynyloxy, halogen, nitro, cyano, -COOH, COOC;-Cgalkyl, COOphenyl, C4-Caalkoxy, phenoxy, (C,-Caalkoxy)-C4-Caalkyl, (C1-Caalkyithio)-C4-Cjalkyl, (C,- Caalkylsulfinyl)-C,-Cjalkyl, (C4-Csalkylsulfonyl)-C4-Caalkyl, NHSO,-C;-C,alkyl, NHSO,-phenyl, N(C1-Cealkyl)SO,-C;-C.alkyl, N(C4-Cealkyl)SO.-phenyl, N(C,-Csalkenyl)SO,-C,-Calkyl, N(Co- Cealkenyl)SO,-phenyl, N(C3-Csalkynyl)SO,-C1-Caalkyl, N(Cs-Cealkynyl)SO,-phenyl, N(C5-C;- cycloalkyl)SO,-C4-Caalkyl, N(Cs-C,cycloalkyl)SO-phenyl, N(phenyl)SO,-C;-C,alkyl, N(phenyl)SOz-phenyl, OS0,-C;-C,alkyl, CONRozsRe26, OSO,-C4-Cyhaloalkyl, OSQO,-phenyl, C4-Caalkylthio, C4-Cjhaloalkylthio, phenylthio, C;-Caalkylsulfonyl, C,-Cshaloalkylsulfonyl, phenyisulfonyl, C,-Cjalkyisulfinyl, C,-Cshaloalkylsulfinyl, phenylsulfinyl, C;-Cjalkylenephenyl : or by -NRo15CO2R27; or Roy is Co-Cealkenyl or C,-Cgalkenyl substituted by halogen, C,-Cjalkoxy, C;-C,alkylthio, . C-Caalkylsulfonyl, Cy-Caalkylsulfinyl, -CONRg32Ross, cyano, nitro, -CHO, -CO,Rgss, -CORgae, -COS-C;-Caalkyl, -NRgasRoss, or by phenyl which may itself be substituted by C;-Cjalkyl, C4-Cghaloalkyl, C4-C,alkoxy, C4-Cshaloalkoxy, Co-Cealkenyl, C3-Cgalkynyl, Cs-Cealkenyloxy, Cs-Cealkynyloxy, halogen, nitro, cyano, -COOH, COOC;-C,alkyl, COOphenyl, C;-Cqalkoxy, phenoxy, (Ci-Cjalkoxy)-C;-Caalkyl, (C, -Caalkylthio)-C,-Cjalkyl, (C4-Caalkylsulfinyl)-C4-C,alkyl, (C4-Caalkylsulfonyl)-C4-Caalkyl, NHSO-C4-Caalkyl, NHSO,-phenyl, N(C;-Cealkyl)SO,-C;-C,- alkyl, N(C4-Cealkyl)SOz-phenyl, N(C,-Cealkenyl)SO2-C4-Ci,alkyl, N(Co-Cealkenyl)SO,-phenyl, N(Cs-Cealkynyl)SO,-C;-Caalkyl, N(Cs-Csalkynyl)SO,-phenyl, N(Cs-C;cycloalkyl)SO,-C;-C,- : alkyl, N(C3-Cscycloalkyl)SO,-phenyl, N(phenyl)SO,-C1-C,alkyl, N(pheny)SO,-phenyl, 0S0,-C4-Cialkyl, CONRgsoR041, OSO,-C4-Cyhaloalkyl, OSO,-phenyl, C;-Cialkylthio, C,-C,- ’ haloalkylthio, phenylthio, C,-Cgalkylsuifonyl, C,-Cshaloalkylsulfonyl, phenylsulfonyl, C;-C,- alkylsulfinyl, C;-Cgshaloalkylsulfinyl, phenylsulfinyl, C-Cjalkylenephenyl or by -NRs3CO,Ry,.;

   or Roi is Cs-Cealkynyl or Cs-Cealkynyl substituted by halogen, C;-C;haloalkyl, cyano,

   e -CO:2Ro44, or by phenyl which may itself be substituted by C;-Caalkyl, C;-Cghaloalkyl, C4-Cs- alkoxy, C;-C;haloalkoxy, Co-Cealkenyl, Cs-Cgalkynyl, Cs;-Cealkenyloxy, Cs-Cealkynyloxy,

   F halogen, nitro, cyano, -COOH, COOC;-C,alkyl, COOphenyl, C,-Calkoxy, phenoxy, (C1-Ca- alkoxy)-C4-Caalkyl, (C4-Cjalkylthio)-C,-C,alkyl, (C4-C,alkylsulfinyl)-C,-Cqalkyl, (C,-C,alkyl- sulfonyl)-C;-Caalkyl, NHSO,-C4-Cjalkyl, NHSO,-phenyl, N(C;-Cealkyl)SO,-Ci-C,alkyl, N(C4-Cgalkyl)SO,-phenyl, N(C.-Csalkenyl)SO,-C1-Caalkyl, N(C.-Cealkenyl)SO2-phenyl, N(Cs-Cealkynyl)SO,-C4-Caalkyl, N(Cs-Csalkynyl)SO,-phenyl, N(C;-Ccycloalkyl)SO,-Cy-Cy- alkyl, N(Cs-C;cycloalkyl)SO.-phenyl, N(phenyl)SO,-C;-Caalkyl, N(phenyl)SO,-phenyt, 080,-C4-Cialkyl, CONRgzR0z0, OSO,-C4-Cghaloalkyl, OSO.-phenyl, C;-Calkylthio, Ci-Cy- haloalkyithio, phenylthio, C;-Calkylsulfonyl, C,-C,haloalkylsulfonyl, phenylsulfonyl, C;-C,- alkylsulfinyl, C;-C,haloalkylsulfinyl, phenylsulfinyl, C,-C,alkylenephenyi or by -NRgs:CO2Roao; or Rot is C3-Cyeycloalkyl or C-Croycloalkyl substituted by C4-Caalkyl, C,-Caalkoxy, Cy- Caalkylthio, C;-Cialkylsulfinyl, C,-Caalkylsulfonyl, or by phenyl which may itself be substituted by halogen, nitro, cyano, C;-Caalkoxy, C4-Cshaloalkoxy, C4-Calkylthio, C,-C,haloalkylthio, C4-Caalkyl or by C4-Cshaloalkyl; or Ro1 is C4-Caalkylene-Cs;-Creycloalkyl, phenyl, or phenyl substituted by C,-C,alkyl, C,-Cghalo- alkyl, C4-C,alkoxy, C4-C,haloalkoxy, C,-Cealkenyl, C3-Cealkynyl, Cs-Cealkenyloxy, C3-Ce- alkynyloxy, halogen, nitro, cyano, -COOH, COOC,-C,alkyl, COOphenyl, C,-C,alkoxy, phenoxy, (C;-Cqalkoxy)-C;-Caalkyl, (C4-Caalkylthio)-C;-Caalkyl, (C4-Cialkylsulfinyl)-C,-C,alkyl, (C4-Caalkylsulfonyl)-C;-Cjalkyl, NHSO,-C,-Calkyl, NHSO2-phenyl, N(C,-Csalkyl)SO,-C,-C,- alkyl, N(C4-Cealky)SOz-phenyl, N(C,-Csalkenyl)SO2-C4-Cialkyl, N(Co-Cgalkenyl)SO,-phenyl, N(Cs-Cealkynyl)SO,-C;-Caalkyl, N(Cs-Cealkynyl)SO.-phenyl, N(C;-C,cycloalkyl)SO,-Cy-C,- alkyl, N(C3-C;cycloalkyl)SO,-phenyl, N(phenyl)SO»-C;-C,alkyl, N(phenyl)SO,-phenyl, 080:-C;-Caalkyl, CONRy4sRo4s, OSO,-C4-Cjhaloalkyl, OSO,-phenyl, C4-C,alkylthio, C,-C,- haloalkylthio, phenylthio, C,-Cjalkylsulfonyl, C,-C,haloalkyisulfonyl, phenylsulfonyl, C-C,- alkylsulfinyl, C;-Cjhaloalkylsulfinyl, phenylsulfinyl or by -NRgssCO2Rq47; OF Rot is C4-Caalkylenephenyl, CORy; or from 4- to 6-membered heterocyclyl;

   Roz, Ross, Ross and Ross are each independently of the others hydrogen, C4-Caalkyl, phenyl, or

   : phenyl substituted by C4-Caalkyl, C;-Cghaloalkyl, Ci-Caalkoxy, Ci-C,haloalkoxy, C,-Cealkenyl,

   - C3-Cealkynyl, C3-Cealkenyloxy, C;-Cealkynyloxy, halogen, nitro, cyano, -COOH, COOC;-C,-

   ’ alkyl, COOphenyl, C;-C,alkoxy, phenoxy, (C;-Caalkoxy)-C4-Caalkyl, (C4-Cialkylthio)-C,-C,-

   alkyl, (C4-Caalkylsulfinyl)-C,-Csalkyl, (Cy-Cjalkylsulfonyl)-C4-Cialkyl, NHSO,-C4-Caalkyl, NHSO,-phenyl, N(C4-Cesalkyl)SO,-C4-Caalkyl, N(C;-Cealkyl)SO,-phenyl, N(C,-Cealkenyl)-

   S0,-C4-Caalkyl, N(C,-Cealkenyl)SO,-phenyl, N(Cs-Csalkynyl)SO2-C4-Caalkyl, N(C3-Ce- e alkynyl)SO,-phenyl, N(Cs-Ccycloalkyl)SO,-C4-Caalkyl, N(Cs-Ccycloalkyl)SO.-phenyl, N(phenyl)S02-C;-C,alkyl, N(phenyl)SO.-phenyl, 0SO,-C;-C,alkyl, CONRoasRoso, ’ OS0,-C,-C,haloalkyl, OSO,-phenyl, C;-C,alkylthio, C,-Cahaloalkylthio, phenylthio, Cy- Caalkylsulfonyl, C;-Chaloalkylsulfonyl, phenylsulfonyl, C,-Caalkyisulfinyl, C;-

   C.haloalkylsulfinyl, phenyisulfinyl, -C4-Cs-alkylphenyl or by -NRgszCO2Rgss; Ros, Ross and Rpg; are each independently of the others C4-Cjalkyl, phenyl, or phenyl substituted by C;-C,alkyl, C;-Cghaloalkyl, C;-Calkoxy, C-Cshaloalkoxy, C.-Cealkenyl, C3-Ce- alkynyl, Cs-Cealkenyloxy, Cs-Cealkynyloxy, halogen, nitro, cyano, -COOH, COQC,-C,alkyl, COOphenyl, C4-Cjalkoxy, phenoxy, (C4-Cialkoxy)-C4-Caalkyl, (C1-Caalkylthio)-C,-Caalkyl, (C4-Caalkylsulfinyl)-C4-Cgalkyl, (C4-Cjalkylsulfonyl)-C,-Caalkyl, NHSO2-C4-C,alkyi, NHSO,-phenyl, N(C4-Cealkyl)SO,-C,-Caalkyl, N(C,-Cealkyl)SO,-phenyl, N(C.-Csalkenyl)- S0,-C4-Cialkyl, N(Co-Cealkenyl)SO,-phenyl, N(Cs-Cealkynyl)SO,-C4-Cjalkyl, N(Cs-Cealkynyl)- SOz-phenyl, N(C;-C;cycloalkyl)SO,-C4-Cjalkyl, N(Cs-C;cycloalkyl)SO,-phenyl, N(phenyl)- S0,-C;-Cyalkyl, N(phenyl)SO,-phenyl, OSO,-C,-Cyalkyl, CONRgssRos4, OSO,-C4-C haloalkyl, OSO,-phenyl, C,-C,alkylthio, C,4-C;haloalkylthio, phenylthio, C;-Cjalkylsulfonyl, C4-C;halo- alkylsulfonyl, phenylsulfonyl, C,-Cjalkylsulfinyl, C1-Cjhaloalkylsulfinyl, phenylsulfinyl, -(CHg)-phenyl or by -NRossCO2Ross; Ros is C4-Cialkyl; Ros is hydrogen, Cy-Caalkyl, C,-Cealkenyl, C;s-Csalkynyl, C3-Crcycloalkyl, phenyl, or phenyl substituted by C;-Caalkyl, Ci-Cshaloalkyl, C;-C,alkoxy, Cs-Cshaloalkoxy, C,-Cealkenyl, C3-Ce- alkynyl, Cs-Cealkenyloxy, C;-Cesalkynyloxy, halogen, nitro, cyano, ~COOH, COOC,-Calkyl, COOphenyl, C4-Cjalkoxy, phenoxy, (C1-Caalkoxy)-Ci-Cialkyl, (C4-Caalkylthio)-C,-Caalkyl, (C4-Caalkylsulfinyl)-Cs-Caalkyl, (C4-Cialkylsulfonyl)-Cy-Cgalkyl, NHSO,-C,-C,alkyl, NHSOz-phenyl, N(C-Cealkyl)SO,-C1-Caalkyl, N(C,-Cealkyl)SO,-phenyl, N(Co-Cealkenyl)- S0,-Cy-Cqalkyl, N(C,-Cealkenyl)SO.-phenyl, N(C3-Cealkynyl)SO,H, N(C3-Cealkynyl)- S0,-C4-Caalkyl, N(C3-Cealkynyl)SO2-phenyl, N(Cs-Crcycloalkyl)SO.H, N(C3-Crcycloalkyl)- to S0,-C4-Cyalkyl, N(C5-Cycycloalkyl)SO,-phenyl, N(phenyl)SO,-C,-Caalkyl, N(phenyl)-

   SO.-phenyl, 0SO,-C;-Caalkyl, CONRgs;Rgss, OSO,-C4-Cishaloalkyl, OSO,-phenyl, C,-C,alkyl- ’ thio, C,-C,haloalkylthio, phenylthio, C,-Cjalkylsulfonyl, C,-Cghaloalkylsulfonyl, phenylsulfonyl, C,-Caalkylsulfinyl, C,-Cghaloalkylsulfinyi, phenylsuifinyl, C;-Casalkylenephenyl or by -NRgsoCO2Rgss; Res is hydrogen, C;-Cqalkyl, Co-Cgalkenyl, C3-Cgalkynyl, Cs-Crcycloatkyl, phenyl, or phenyl substituted by C4-Caalkyl, C;-Cghaloalkyl, C;-C,alkoxy, Cs-Cshaloalkoxy, C,-Cgalkenyl,

   Cs-Cealkynyl, C3-Cealkenyloxy, Cs-Cgalkynyloxy, halogen, nitro, cyano, -COOH, COOC-Ca- o alkyl, COOphenyl, C;-C,alkoxy, phenoxy, (C-Cialkoxy)-C;-Caalkyl, (C;-Cjalkylthio)-Cy-Cu- alkyl, (C4-Caalkyisulfinyl)-C,-Caalkyl, (C4-Caalkylsulfonyl)-C4-Cjalkyl, NHSO,-C,-Caalkyl, s NHSO-phenyl, N(C;-Cealkyl)SO,-C4-Caalkyl, N(C;-Csalkyl)SO.-phenyl, N(C»-Csalkenyl)- S0,-C4-Caalkyl, N(C,-Cealkenyl)SOx-phenyl, N(Cs-Cgalkynyl)SO,-C;-Caalkyl, N(Cs-Cealkynyl)- SOz-phenyl, N(C3-Ccycloalkyl)SO.-C4-Cjalkyl, N(Cs-C,cycloalkyl)SO,-phenyl, N(phenyl)-

   S0.-C,-Caalkyi, N(phenyl)SOz-phenyl, 0SO,-C;-C,alkyl, CONRog; Rogz, OSO,-C;-Cshaloalkyl, OSO,-phenyl, C,-C,alkylthio, C;-Cshaloalkylthio, phenylthio, C;-Calkylsulfonyl, C,-C,halo- alkylsulfonyl, phenylsulfonyl, C,-C,alkylsulfinyl, C,-C4haloalkyisulfinyl, phenylsulfinyl, C,-Cs- alkylenephenyl or by -NRgsCO2Res; Roz is phenyl, C4-Cgalkyl, C-Cjalkoxy or -NRggRg; Ros and Rog are each independently of the other C,-C,alkyl, phenyl, or phenyl substituted by halogen, nitro, cyano, C4-C,alky), C,-Caalkoxy, C;-C,thioalky), -CO.Rges, -CORgs7, C1-Ca- alkylsulfonyl, C,-Cjalkylsulfinyl or by C,-Cshaloalkyl; or Res and Ryo together form a 5- or 6- membered ring, which may be interrupted by oxygen, NRgss or by S; Rots, Rost, Ross, Ross, Rosz, Rose, Roso and Ress are each independently of the others hydrogen, C;-Caalkyl, C,-Cgalkenyl, C3-Cealkynyl or Cs-C,cycloalkyil; Rozs, Rozs, Rozy, Rozs, Roos, Roso, Roaz, Roas, Roar Ross, Roses Rosz, Roa, Roat, Roz, Roas, Ross, Roa7, Ross, Roso, Rosa, Rosa, Ross, Ros7, Ross, Ross, Ros, Ros2, Ross, Ross and Res are each independently of the others hydrogen, C,-Caalkyl, C,-Csalkenyl, Cs-Cealkynyl, Cs-C;cyclo- alkyl, phenyl, or phenyl substituted by halogen, nitro, cyano, C;-Cjalkoxy, C,-Cshaloalkoxy, C4-Caalkylthio, C4-C;haloalkylthio, C4-Cjalkyl or by C4-Cshaloalkyl; and Ras is Cy-Caalkyl, Cy-C,haloalkyl, C3-Cealkenyl, C;-Cghaloalkenyl, Cs-Cealkynyl, Cs-Cghalo- alkynyl, Cs-Cecycloalkyl, or C5-Cecycloalkyl substituted by halogen, C;-Cjalkyl, C,-Cshalo- alkyl, Cs-Cealkenyl, Cs-Cehaloalkenyl, Cs-Csalkynyl, Cs-Cghaloalkynyl, C4-Cijalkoxycarbonyl, C,-Caalkylthio, C4-Caalkylsulfinyl, C4-C,alkyisulfonyl, C,-C,haloalkylthio, C,-

   C.haloalkylsulfinyl, C4-Cshaloalkylsulfonyl, C,-Calkylcarbonyl, di(C,-Cgalkyl)amino, C;-

   C.alkoxy, C4-Cshaloalkoxy, C;-Cjalkyl-S(O).0, C,-Cjhaloalkyl-S(0O),0, or by phenyl! which may itself be substituted by halogen, C,-C,alkyl, C;-Cshaloalkyl, C3-Cealkenyl, Cs-Cealkynyl, ’ cyano, nitro or by COOH; or an agronomically acceptable salt of such a compound, and b) a synergistically effective amount of one or more compounds selected from a compound of formula 2.1

   Rs, COOH LL pe Ry~ ON = ve 2-1); v N H 0 Me wherein Rg is CH,-OMe, ethyl or hydrogen; Rs2 is hydrogen or Rs; and Rs, together are the group -CH=CH-CH=CH-; and a compound of formula 2.2 Rss [es N (2.2), CHO : Ry, O wherein Rss is ethyl, Rs, is methyl or ethyl and Rss is -CH(Me)-CH,OMe, <S>-CH(Me)-CH,OMe, CH, OMe or CH,O-CH,CHg; and a compound of formula 2.3 Me = Va (2.3), L Jere Me © wherein Rss is CH(Me)-CH,OMe or <S>CH(Me)-CH,OMe; and a compound of formula 2.4 N~ SN R PY PY R 24. “oN N nN” 59 » H H wherein Rs; is chlorine, methoxy or methylthio, Rss is ethyl and Rs is ethyl, isopropyl, -C(CN)(CHj3)-CHj or tert-butyl; and a compound of formula 2.5

   0) X Re; © wherein Rg is ethyl or n-propyl, Rg; is COO" 1/2 Ca™, ~-CH,-CH(Me)S-CH,CH; or the group AQ! and X is oxygen, N-O-CH,CHj or N-O-CH,CH=CH-CI; and a compound of formula 2.6

   Re. H © N— PY ” —a. ¢ = Nr A Fg (2.6), Res Res wherein Rg; is hydrogen, methoxy or ethoxy, Res is hydrogen, methyl, methoxy or fluorine, Res is COOMe, fluorine or chlorine, Res is hydrogen or methyl, Y is methine, C-F or nitrogen, Z is methine or nitrogen and Re is fluorine or chlorine; and a compound of formula 2.7 Re, 0” AN (2.7),

   N.. = NT To wherein Re; is hydrogen or -C(O)-S-n-octyl; and a compound of formula 2.8 “ OH Res Res " (2.8),

   CN .

   wherein Reg is either bromine or iodine; “ and a compound of formula 2.9 oO 0 Res 0 (2.9), XC QL 4 “Me : wherein Rego is chlorine or nitro; and a compound of formula 2.10 R,, O ° ) _CHF, N cl N, ~L (2.10), } N Me

   R.: wherein Ry, is fluorine or chlorine and Ry, is -CH,-CH(Cl)-COOCH,CHj; or -NH-SO.Me; and a compound of formula 2.11 Me \ LO o ©
2. 2.11), R, (2.11) / \ N_ 0 wherein Ry, is trifluoromethyl or chlorine; and a compound of formula 2.12 P COOH © Me” >TY (2.12), Wh 0 R NH, i “ wherein Ry; is NH; or <S>NH,; and a compound of formula 2.13

   R ve las 74 I A AP ao NY eas), vs aN J Ms J 0) N N N Ye H H wherein Y is nitrogen, methine, NH-CHO or N-Me, Y; is nitrogen, methine or C-I, Ys is methine, Y, is methine or Y; and Y,4 together are sulfur or C-Cl, Yj is nitrogen or methine, Ys is methyl, difluoromethoxy, trifluoromethyl or methoxy, Y7 is methoxy or difluoromethoxy and R74 is CONMe,, COOMe, COOC;Hs, trifluoromethyl, CH,-CH,CF; or SO,CH,CHg, or a sodium salt thereof; and the compound of formula 2.13.c O CH, Cl © o- CH, / \ O

   N. S 2.13.0) N™ 7~NH bi x (2.13.0), 0 CH CH ~~ rd 3 S oA N N 0) H and the compound of formula 2.14 Me N—N Me Me 4 Vs Me N (2.14), 0] N—H / H and the compound of formula 2.15 HN Cl and the compound of formula 2.16

   INN . HOOC \ PO(OH), (2.16), H “ and the compound of formula 2.17 N Me 1 _0 (2.17), NW : | O H and the compound of formula 2.18 Oo \ _ Me NO H / — (2.18), N= Me Oo Me and the compound of formula 2.19 Cl Cer (2.19), Cl OMe and the compound of formula 2.20 0 : Me PIS Et Ow sg”

   (2.20), Me Me Me and the compound of formula 2.21

   0 nate : “ N \ 0] 0 Me EN (2.21), Ao Me 0) I and the compound of formula 2.22 Cl Oo oN (2.22), 0 Me Me and the compound of formula 2.23 Cl ol Se (2.23), \__cooH and the compound of formula 2.24 F O : o o (2.24), 0 / n-pentyl :

   and the compound of formula 2.25 , F fy. Cl N 7) (2.25), ) R'E MeOOC 0 and the compound of formula 2.26 Me CF, H—n ° N= -. Re and the compound of formula 2.27 F O EC N d (2.27), 0) / we’ : and the compound of formula 2.28 + + Me—N \ / \ / N—Me (2.28), Cr Cl ; and the compound of formula 2.29 cr QO

   * J. ’ Cl N — “ N (2.29) 0 or ) wa and the compound of formula 2.30 Moe IN N (2.30), FsC S 0" F Oo and the compound of formula 2.31 ( ( 11 N N 2.31), \ A) (&31) N=N L Me and the compound of formula 2.32 F Br CF, ~~ Cl \ N — NT Me (2.32), 0) 0 wo—( Me ) and the compound of formula 2.33 ) H 0 HOOC \ A - i ~~ IN \ 0 Me—S—me (2-33), OH Me

   . and the compound of formula 2.34 H,N ~ H- SO,NHCO,CH, (2.34), ’ CF, =N and the compound of formula 2.35 CH,NH { (2.35), Cl 0) ) CH; _N._O and the compound of formula 2.36 XA (2.38), Cl I ~ G(CH,), (Ss CH,CH(CHY), and the compound of formula 2.37 N Det (2.37),

   F.C” N” CEH FCN CHF, and the compound of formula 2.38 sro COSCH, (2.38), CH,CH(CH,), oH (CHy,N __N__O : and the compound of formula 2.39 NM Tr (2.39), 0 and the compound of formula 2.40 cl & NHCON(CH,), (2.40), ’ Cl Cl OCH,CO,H and the compound of formula 2.41 & TT (2.41), CH,

   CH, and the compound of formula 2.42 oa) OCHCOM (5 42), CH, ik (CHY,C~¢ S 3 NCONHCH, and the compound of formula 2.43 N-N (2.43), and the compound of formula 2.44 H,C CH, 7 A CH,CIi

   (2.44), OCH,CH, and the compound of formula 2.45 o © Oo 0 Oo / 0) So H J N N N— CH, 3 \ h=( (2.45), NE CH, and the compound of formula 2.46 0 O-isopropyl HC N N~ 2.46 A\ cl (2.46), ~~ ) CF; : Br F and the compound of formula 2.47

   0) : OCH,CH, Oo — \ Cl (2.47), CL oO and the compound of formula 2.48 CH, F F

   ~~ . (2.48), oo cr o H,C po . o CH, Q and the compound of formula 2.49 F CH, O N _N—N—L ~N H H

   (2.49), ZZ o F HO and the compound of formula 2.50 CH, Hig CH, HC N NS (2.50) CH, pu N CH 0) \ NH, p and the compound of formula 2.51

   F O CH, JES sens: Cl N \ F . N— F © (2.51). 0) J CH, o—

   2. A composition according to claim 1, wherein in formula each R is independently hydrogen, C;-Cgalkyl, C,-Cgalkenyl, C,-Cshaloalkenyl, C,-Cgalkynyl, C2-Cghaloalkynyl, C3-Cgeycloalkyl , C4-Cgalkoxy, Cyi-Cghaloalkoxy, C,-Cgalkylthio, C-Csalkyl- sulfinyl, C4-Cgalkylsulfonyl, C;-Cghaloalkyl, C;-Cshaloalkyithio, C-Cghaloalkylsulfinyl, C4-Ce- haloalkylsulfonyl, Cs-Cealkoxycarbonyl, C,-Cealkylcarbonyl, C-Cealkylamino, di(C,-Cealkyl)- amino, C4-Cgalkylaminosulfonyl, di(C-Cealkylaminosulfonyl, -N(R1)-S-R2, -N(R3)-SO-R,, -N(Rs)-SO2-Re, nitro, cyano, halogen, hydroxy, amino, benzyithio, benzylsulfinyl, benzyl- sulfonyl, phenyl, phenoxy, phenylthio, phenylsulfinyl or phenylsulfonyl; wherein the phenyl group may itself be mono-, di- or tri-substituted by C,-Csalkyl, C4-Cghaloalkyl, Cs-Cealkenyl, Cs-Cghaloalkenyl, Cs-Csalkynyl, Cs-Cghaloalkynyl, C;-Csalkoxy, C;-Cghaloalkoxy, Cs-Ce- alkenyloxy, Cs-Cealkynyloxy, mercapto, C;-Cealkylthio, C-Cshaloalkylthio, C3-Cgalkenylthio, Cs-Cghaloalkenyithio, Cs-Cealkynylthio, C,-Csalkoxyalkylthio, Ca-Csacetylalkylthio, C3-Ce- alkoxycarbonylalkyithio, C,-C,cyanoalkylthio, C,-Cgalkylsulfinyl, C;-Cshaloalkylsulfinyi, Ci-Cealkylsulfonyl, C,-Cghaloalkylsulfonyl, aminosulfonyl, C-C.alkylaminosulfonyl,

   C.-C,dialkylaminosulfonyl, C-Csalkylene-R.s, NR4sR47, halogen, cyano, nitro, phenyl or by benzylthio, wherein the latter phenyl and benzylthio groups may themselves be substituted on the phenyl ring by C,-Czalkyl, C,-Cshaloalkyl, C,-Csalkoxy, C4-Cshaloalkoxy, halogen, cyano or by nitro; : or each R is independently a monocyclic or fused bicyclic ring system having from 5 to 10 members, which may be aromatic or partially saturated and may contain from 1 to 4 hetero R atoms selected from nitrogen, oxygen and sulfur; wherein the ring system either is bound directly to the pyridine ring or is bound to the pyridine ring via a C;-Cjalkylene group, and each ring system may not contain more than two oxygen atoms and may not contain more than two sulfur atoms, and the ring system may itself be mono-, di- or tri-substituted by C4-Cealkyl, C4-Cghaloalkyl, C3-Cgalkenyl, Cs-Cghaloalkenyl, Cs-Cgalkynyl, Cs-Cshaloalkynyl, C,-Cealkoxy, C4-Cghaloalkoxy, Cs-Cgalkenyloxy, Cs-Cealkynyloxy, mercapto, C-Cealkylthio,

   C,-Cshaloalkyithio, Cs-Cgalkenyithio, C;-Cghaloalkenylthio, Cs-Cgalkynylthio, C,-Csalkoxy- o alkylthio, Cs-Csacetylalkylthio, Ca-Csalkoxycarbonylalkyithio, C»-Cycyanoalkylthio, C4-Cealkyl- sulfinyl, C-Cghaloalkylsulfinyl, C+-Cealkylsulfonyl, C4-Cghaloalkylsulfonyl, aminosulfony!, ov C,-Caalkylaminosulfonyl, C.-C,dialkylaminosulfonyl, C,-Csalkylene-R;, NRgR,, halogen, cyano, nitro, phenyl or by benzylthio, wherein phenyl and benzylthio may themselves be substituted on the phenyl ring by C,-Cjalkyl, C,-Cshaloalkyl, C;-Cgalkoxy, C,-Cshaloalkoxy, halogen, cyano or by nitro, and wherein the substituents on the nitrogen in the heterocyclic ring are other than halogen.
3. 3. A composition according to claim 1, that comprises, as compound of formula |, a compound of formula la 0) 7 Res N Rg wherein Rug is C4-Cealkyl, Co-Cealkenyl, C,-Cghaloalkenyl, C,-Cgalkynyl, C,-Cghaloalkynyl, C5-Cecyclo- alkyl, C4-Cghaloalkyl, or a monocyclic or fused bicyclic ring system having from 5 to 10 members, which may be aromatic or partially saturated and may contain from 1 to 4 hetero atoms selected from nitrogen, oxygen and sulfur, wherein the ring system either is bound directly to the pyridine ring or is bound to the pyridine ring via a C;-C4alkylene group, and each ring system may not contain more than two oxygen atoms and may not contain more than two sulfur atoms, and the ring system may itself be mono-, di- or tri-substituted by Ci-Cealkyl, C4-Cghaloalkyl, Cs-Cealkenyl, Cs-Cghaloalkenyl, Cs-Cealkynyl, Cs-Cghaloalkynyl, C4-Cealkoxy, Cy-Cghaloalkoxy, Cs-Cgalkenyloxy, Cs-Cgalkynyloxy, mercapto, C4-Cgalkylthio, C,-Cghaloalkylthio, Cs-Csalkenylthio, Cs-Cshaloalkenyithio, Ca-Cealkynylthio, C»-Csalkoxy- ) alkylthio, Cs-Csacetylalkyithio, Cs-Cealkoxycarbonylalkyithio, C,-C,cyanoalkyithio, Ci-Cealkyl- sulfinyl, C,-Cghaloalkylsulfinyl, C,-Cgalkylsulfonyl, C,-Cghaloalkylsulfonyl, aminosulfonyl, » C4-C.alkylaminosulfonyl, C,-C,dialkylaminosulfonyl, C,-Csalkylene-R7, NRgRs, halogen, cyano, nitro, phenyl or by benzylthio, wherein phenyl and benzylthio may themselves be ° substituted on the phenyl ring by C,-Csalkyl, C;-Cshaloalkyl, C,-Csalkoxy, C4-Cshaloalkoxy, halogen, cyano or by nitro, and wherein the substituents on the nitrogen in the heterocyclic ring are other than halogen;

   Ry is hydrogen, C-Cealkyl, C4-Cghaloalkyl, halogen, or phenyl which may be substituted by

   . C4-Csalkyl, C4-Cshaloalkyl, C4-Caalkoxy, C4-Cshaloalkoxy, halogen, cyano or by nitro, and Rs is C4-Cghaloalkyl.
4. 4. A composition according to claim 3, wherein Rg is Ci-Cealkyl, C2-Cgalkenyl, C,-Cghalo- alkenyl, Co-Csalkynyl, C,-Cghaloalkynyl, Cs-Cgcycloalkyl or C;-Cghaloalkyl.
5. 5. A composition according to claim 1, wherein in formula | Q is the group Q, or Qa.
6. 6. A composition according to claim 5, wherein in the group Q, Ras is hydroxy.
7. 7. A composition according to claim 5, wherein in the group Qs Ryo is hydroxy.
8. 8. A method of controlling undesired plant growth in crops of useful plants, which comprises allowing a herbicidally effective amount of a composition according to claim 1 to act on the crop plant or the locus thereof.
9. 9. A method according to claim 8, wherein the crop plant is maize or sugar cane.
10. 10. A method according to claim 8, wherein the crops of useful plants are treated with the mentioned composition at rates of application corresponding to a total amount of active ingredient of from 1 to 5000 g per hectare.
11. 11. A herbicidally selective composition that, in addition to comprising customary inert formulation adjuvants, such as carriers, solvents and wetting agents, comprises as active ingredient a mixture of a) a herbicidally-synergistically effective amount of a compound of formula I according to claim 1 and one or more compounds selected from the compounds of formulae 2.1 to 2.51 according to claim 1 and ? b) a herbicidally-antagonistically effective amount of a compound selected from the compound of formula 3.1

    CCL No Me (3.4), ih IA O Cl and the compound of formula 3.2 Cl —N J) eo N Cl and the compound of formula 3.3 Cl

    =

    3.3), ~ (3.3) N 0-CH,-C(0)-0-CH(CH,)C.H,,-n and the compound of formula 3.4 ClMe_ COOCH,CH, $0 (3.4), \ — . N™ COOCH,CH; + and the compound of formula 3.5

    ° . N Me Cl (35), 0 X “ \ / 0 Me and the compound of formula 3.6

    COOH y COOH

    (3.6),

    0 . and the compound of formula 3.7 Cl 0 Cl Me N (3.7), Me N Me oO and the compound of formula 3.8 Cl - N oe oY (3.8), CF, 0) and of formula 3.9 Cl,CHCON(CH,CH=CH,), (3.9), and of formula 3.10 o Cl ® O—CH _{) \ / 2 (3.10), N CF, - and of formula 3.11

    Cl

    Ps . cl Ng (3.11), C1 and of formula 3.12 COOH dy oN (3.12) and its ethyl ester, and of formula 3.13 CH,CH, o” Cl Nx (@] Cl N (3-13), —N Cl Ci Cl and of formula 3.14 Te 0 0) AJ S H l N (3.14), H Oo A , © on, : and of formula 3.15 s i \ O (3.15) RY O / al 0

    H.C bo) and of formula 3.16 OH 3 N IAN COLT N-n' (3.16). ye

    H.C
12. 12. A method for the selective control of weeds and grasses in crops of useful plants, which comprises treating the useful plants, seeds or cuttings thereof, or the area of cultivation thereof, with a herbicidally-synergistically effective amount of a composition according to claim 10.
13. 13. A method according to claim 12, wherein the rate of application of herbicides is from 1 to 5000 g/ha and the rate of application of safener is from 0.001 to 0.5 kg/ha.
14. 14. A method according to claim 12, wherein the crops of useful plants are maize or sugar cane.
15. 15. A herbicidally selective composition that, in addition to comprising customary inert formulation adjuvants, such as carriers, solvents and wetting agents, comprises as active ingredient a mixture of a) a herbicidally effective amount of a compound of formula | according to claim 1 and * b) a herbicidally-antagonistically effective amount of a compound selected from the compound of formula 3.1

    CLL No Me (3), ° cl ~o Cl and the compound of formula 3.2 Cl —N \ 4) (3.2), N Cl ’ and the compound of formula 3.3 Cl ~~

    3.3), ~~ (3.3) N O-CH,-C(0)-O-CH(CH,)C.H,,-n and the compound of formula 3.4 : ClMe_ COOCH,CH, : asl (3.9), N™ “coocH,cH, and the compound of formula 3.5 je ’ N me Cl (35), 0 X ¢ \ /) © Me and the compound of formula 3.6

    COOH ¢ COOH

    (3.6), ® 6] and the compound of formula 3.7 Cl 0 eS Me N (8.7), Me N Me 0 and the compound of formula 3.8 Ci N Te TY (3.8), CF, 0 ~ and of formula 3.9 CI,CHCON(CH,CH=CHy,), (3.9), and of formula 3.10 Oo O° O—cH _{) \ / 2 (3.10), N CF, v and of formula 3.11

    Cl * PE

    3.11), “ Cl nC) (8.11) 3 and of formula 3.12 COOH O77 0 (3.12) and its ethyl ester, and of formula 3.13 CH,CH,

    0” . Cl N= o . Cl N (3.13), —N Cl Cl Cl and of formula 3.14 Te 0 0 HJ] ll N (3.14), H : ° a 0 GH, pl and of formula 3.15

    S % i \ O (3.15) ['Y O % al 0) H,C 0 and of formula 3.16 OH O N IAN LLY, N-n® (3.16). ye H,C
16. 16. A method for the selective control of weeds and grasses in crops of useful plants, which comprises treating the useful plants, seeds or cuttings thereof, or the area of cultivation thereof, with a herbicidally-synergistically effective amount of a composition according to claim 14. z