Herbicidal compositions

Abstract

A selectively herbicidal composition for controlling grasses and weeds in crops of useful plants, comprising a) a herbicidally effective amount of a compound of formula I wherein R 1 and R 3 are, each independently of the other, ethyl, haloethyl, ethynyl, C 1 - or C 2 -alkoxy, C 1 - or C 2 -haloalkoxy, C 1 - or C 2 -alkylcarbonyl or C 1 - or C 2 -hydroxyalkyl; R 4 and R 5 together are a group Z 2 —CR 14 (R 15 )—CR 16 (R 17 )—O—CR 18 (R 19 )—CR 20 (R 21 )— (Z 2 ); R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 and R 21 are, each independently of the others, hydrogen, halogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl, wherein an alkylene ring may be fused or spiro-bound to the carbon atoms of the group Z 2 , which alkylene ring, together with the carbon atoms of the group Z 2 , to which it is bonded, contains from 2 to 6 carbon atoms and may be interrupted by oxygen, or the alkylene ring bridges at least one ring atom of the group Z 2 ; G is hydrogen, —C(X 1 )—R 30 , —C(X 2 )—X 3 —R 31 , —C(X 4 )—NR 32 (R 33 ), —S(O) 2 —R 34 , —P(X 5 )R 35 R 36 , —CH 2 —X 6 —R 37 or an alkali metal, alkaline earth metal, sulfonium or ammonium cation; X 1 , X 2 , X 3 , X 4 , X 5 and X 6 are, each independently of the others, oxygen or sulfur; R 30 , R 31 , R 32 , R 33 , R 34 , R 35 , R 36 and R 37 are, each independently of the others, hydrogen, C 1 -C 10 alkyl, C 1 -C 10 haloalkyl, C 1 -C 10 cyanoalkyl, C 1 -C 10 nitroalkyl, C 1 -C 10 aminoalkyl, C 2 -C 5 -alkenyl, C 2 -C 5 haloalkenyl, C 3 -C 8 cycloalkyl, C 1 -C 5 alkylamino-C 1 -C 5 alkyl, di(C 1 -C 5 alkyl)amino-C 1 -C 5 alkyl, C 3 -C 7 Cycloalkyl-C 1 -C 5 alkyl, C 1 -C 5 alkoxy-C 1 -C 5 alkyl, C 3 -C 5 alkenyloxy-C 1 -C 5 alkyl, C 3 -C 5 alkynyloxy-C 1 -C 5 alkyl, C 1 -C 5 alkylthio-C 1 -C 5 alkyl, C 1 -C 5 alkylsulfoxy-C 1 -C 5 alkyl, C 1 -C 5 -alkylsulfonyl-C 1 -C 5 alkyl, C 2 -C 8 alkylideneaminooxy-C 1 -C 5 alkyl, C 1 -C 5 alkylcarbonyl-C 1 -C 5 alkyl, C 1 -C 5 alkoxycarbonyl-C 1 -C 5 alkyl, C 1 -C 5 alkylaminocarbonyl-C 1 -C 5 alkyl, di(C 1 -C 5 alkyl)-aminocarbonyl-C 1 -C 5 alkyl, C 1 -C 5 alkylcarbonylamino-C 1 -C 5 alkyl, C 1 -C 5 alkylcarbonyl-(C 1 -C 5 -alkyl)-amino-C 1 -C 5 alkyl, tri(C 1 - or C 2 -alkyl)silyl-C 1 -C 5 alkyl, phenyl, heteroaryl, phenyl-C 1 -C 5 alkyl, heteroaryl-C 1 -C 5 alkyl, phenoxy-C 1 -C 5 alkyl or heteroaryloxy-C 1 -C 5 alkyl, wherein the afore-mentioned aromatic rings may be substituted by halogen, nitro, cyano, amino, di-(C 1 -C 4 alkyl)amino, hydroxy, methoxy, ethoxy, methylthio, ethylthio, formyl, acetyl, propionyl, carboxyl, C 1 -C 5 alkoxycarbonyl or by C 1 - or C 2 -haloalkyl; R 34 , R 35 and R 36 are, in addition, C 1 -C 10 alkoxy, C 1 -C 10 haloalkoxy, C 1 -C 5 alkylamino, di(C 1 -C 5 -alkyl)amino, benzyloxy or phenoxy, wherein the aromatic rings of the last two substituents may be substituted by halogen, nitro, cyano, amino, dimethylamino, hydroxy, methoxy, ethoxy, methylthio, ethylthio, formyl, acetyl, propionyl, carboxyl, C 1 -C 5 alkoxycarbonyl or by C 1 - or C 2 -haloalkyl; and R 37 is, in addition, C 1 -C 10 alkylcarbonyl, or a salt or diastereoisomer of a compound of formula I, and b) an amount, which is effective for antagonism of the herbicide, of a compound of formula IIa or of formula IIb or of formula IIc or of formula IId or of formula IIe wherein the substituents R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , n, m, R 28 , R 29 , R 30 , R 31 , R 32 , o, p, G 2 , R 33 , R 34 , R 35 , R 36 , R 37 and are as defined in claim 1.

1 . A selectively herbicidal composition which, in addition to customary inert formulation assistants, comprises as active ingredient a mixture of 
 a) a herbicidally effective amount of a compound of formula I                          wherein    R 1  and R 3  are, each independently of the other, ethyl, haloethyl, ethynyl, C 1 - or C 2 -alkoxy, C 1 - or C 2 -haloalkoxy, C 1 - or C 2 -alkylcarbonyl or C 1 - or C 2 -hydroxyalkyl;    R 4  and R 5  together are a group Z 2  —CR 14 (R 15 )—CR 16 (R 17 )—O—CR 18 (R 19 )—CR 20 (R 21 )— (Z 2 ); R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20  and R 21  are, each independently of the others, hydrogen, halogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl, wherein an alkylene ring may be fused or spiro-bound to the carbon atoms of the group Z 2 , which alkylene ring, together with the carbon atoms of the group Z 2 , to which it is bonded, contains from 2 to 6 carbon atoms and may be interrupted by oxygen, or the alkylene ring bridges at least one ring atom of the group Z 2 ;    G is hydrogen, —C(X,)—R 30 , —C(X 2 )—X 3 —R 31 , —C(Y4)—NR 32 (R 33 ), —S(O) 2 —R 34 , —P(X 5 )R 35 R 36 , —CH 2 —X 6 —R 37  or an alkali metal, alkaline earth metal, sulfonium or ammonium cation;    X 1 , X 2 , X 3 , X 4 , X 5  and X 6  are, each independently of the others, oxygen or sulfur;    R 30 , R 31 , R 32 , R 33 , R 34 , R 35 , R 36  and R 37  are, each independently of the others, hydrogen, C 1 -C 10 alkyl, C 1 -C 10 haloalkyl, C 1 -C 10 cyanoalkyl, C 1 -C 10 nitroalkyl, C 1 -C 10 aminoalkyl, C 2 -C 5 alkenyl, C 2 -C 5 haloalkenyl, C 3 -C 8 cycloalkyl, C 1 -C 5 alkylamino-C 1 -C 5 alkyl, di(C 1 -C 5 alkyl)amino-C 1 -C 5 alkyl, C 3 -C 7 cycloalkyl-C 1 -C 5 alkyl, C 1 -C 5 alkoxy-C 1 -C 5 alkyl, C 3 C 5 alkenyloxy-C 1 -C 5 alkyl, C 3 -C 5 alkynyloxy-C 1 -C 5 alkyl, C 1 -C 5 alkylthio-C 1 -C 5 alkyl, C 1 -C 5 alkylsulfoxy-C 1 -C 5 alkyl, C 1 -C 5 alkylsulfonyl-C 1 -C 5 alkyl, C 2 -C 8 alkylideneaminooxy-C 1 -C 5 alkyl, C 1 -C 5 alkylcarbonyl-C 1 -C 5 alkyl, C 1 -C 5 alkoxycarbonyl-C 1 -C 5 alkyl, C 1 -C 5 alkylaminocarbonyl-C 1 -C 5 alkyl, di(C 1 -C 5 alkyl)aminocarbonyl-C 1 -C 5 alkyl, C 1 -C 5 alkylcarbonylamino-C 1 -C 5 alkyl, C 1 -C 5 alkylcarbonyl-(C 1 -C 5 -alkyl)-amino-C 1 -C 5 alkyl, tri(C 1 - or C 2 -alkyl)silyl-C 1 -C 5 alkyl, phenyl, heteroaryl, phenyl-C 1 -C 5 alkyl, heteroaryl-C 1 -C 5 alkyl, phenoxy-C 1 -C 5 alkyl or heteroaryloxy-C 1 -C 5 alkyl, wherein the afore-mentioned aromatic rings may be substituted by halogen, nitro, cyano, amino, di(C 1 -C 4 alkyl)amino, hydroxy, methoxy, ethoxy, methylthio, ethylthio, formyl, acetyl, propionyl, carboxyl, C 1 -C 5 alkoxycarbonyl or by C 1 - or C 2 -haloalkyl;    R 34 , R 35  and R 36  are, in addition, C 1 -C 10 alkoxy, C 1 -C 10 haloalkoxy, C 1 -C 5 alkylamino, di(C 1 -C 5 alkyl)amino, benzyloxy or phenoxy, wherein the aromatic rings of the last two substituents may be substituted by halogen, nitro, cyano, amino, dimethylamino, hydroxy, methoxy, ethoxy, methylthio, ethylthio, formyl, acetyl, propionyl, carboxyl, C 0 -C 5 alkoxycarbonyl or by C 1 - or C 2 -haloalkyl; and    R 37  is, in addition, C 1 -C 1 oalkylcarbonyl, or a salt or diastereoisomer of a compound of formula I, and    b) an amount, which is effective for antagonism of the herbicide, of a safener of formula IIb                          wherein    R 23  is hydrogen, or an alkali metal, alkaline earth metal, sulfonium or ammonium cation, or ethyl,    
     
     
         2 . A composition according to  claim 1 , which comprises as active ingredient a mixture of 
 a) a herbicidally effective amount of a herbicide of formula I, wherein    R 1 , R 3 , R 4 , R 5  and G are as defined in  claim 1 , and    b) an amount, which is effective for antagonism of the herbicide, of a safener of formula IIb, wherein    R 23  is as defined in  claim 1  for formula IIb.    
     
     
         3 . A composition according to  claim 1 , wherein R 1  and R 3  in the compounds of formula I are, each independently of the other, ethyl, haloethyl, ethynyl, C 1 - or C 2 -alkoxy or C 1 - or C 2 -haloalkoxy.  
     
     
         4 . A composition according to  claim 1 , wherein R 4  and R 5  in the compounds of formula I together form a group Z 2  which is —CR 14 (R 15 )—CR 16 (R 17 )—O—CR 18 (R 19 )—CR 20 (R 21 )— wherein R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20  and R 20  are hydrogen.  
     
     
         5 . A composition according to  claim 1 , wherein G in the compounds of formula I is hydrogen, —C(X 1 )—R 30 , —C(X 2 )—X 3 —R 31 , —C(X 4 )—NR 32 (R 33 ), —S(O) 2 —R 34 , —P(X 5 )R 35 R 36 , —CH 2 —X 6 —R 37  or an alkali metal, alkaline earth metal, sulfonium or ammonium cation; X 1 , X 2 , X 3 , X 4 , X 5  and X 6  are, each independently of the others, oxygen or sulfur; R 30 , R 31 , R 32 , R 33 , R 34 , R 35 , R 36  and R 37  are, each independently of the others, hydrogen, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 1 -C 8 cyanoalkyl, C 1 -C 8 nitroalkyl, C 1 -C 8 aminoalkyl, C 2 -C 5 alkenyl, C 2 -C 5 haloalkenyl, C 3 -C 8 cycloalkyl, C 1 -C 5 alkylamino-C 1 -C 2 alkyl, di(C 1 -C 5 alkyl)amino-C 1 -C 2 alkyl, C 3 -C 7 cycloalkyl-C 1 -C 2 alkyl, C 1 -C 4 alkoxy-C 1 -C 4 alkyl, C 2 -C 4 alkenyloxy-C 1 -C 4 alkyl, C 3 -C 4 alkynyloxy-C 1 -C 4 alkyl, C 1 -C 4 alkylthio-C 1 -C 4 alkyl, C 1 -C 2 alkylsulfoxy-C 1 -C 2 alkyl, C 1 -C 2 alkylsulfonyl-C 1 -C 2 alkyl, C 2 -C 8 alkylideneaminooxy-C 1 -C 2 -alkyl, C 1 -C 5 alkylcarbonyl-C 1 -C 2 alkyl, C 1 -C 5 alkoxycarbonyl-C 1 -C 2 alkyl, C 1 -C 5 alkylamino-carbonyl-C 1 -C 2 alkyl, di(C-C 4 alkyl)aminocarbonyl-C 1 -C 2 alkyl, C 1 -C 5 alkylcarbonylamino-C 1 -C 2 alkyl, C 1 -C 2 alkylcarbonyl-(C 1 -C 3 alkyl)-amino-C 1 -C 2 alkyl, tri(C 1 - or C 2 -alkyl)silyl-C 1 -C 3 alkyl, phenyl, heteroaryl, phenyl-C 1 -C 2 alkyl, heteroaryl-C 1 -C 2 alkyl, phenoxy-C 1 -C 2 alkyl or heteroaryloxy-C 1 -C 2 alkyl; R 34 , R 35  and R 36  are, in addition, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 3 alkylamino, di(C 1 -C 3 alkyl)amino, benzyloxy or phenoxy, wherein the aromatic rings of the last two substituents may be substituted by halogen, nitro, cyano, amino, dimethylamino, hydroxy, methoxy, ethoxy, methylthio, ethylthio, formyl, acetyl, propionyl, carboxyl, C 1 -C 5 alkoxycarbonyl or by C 1 - or C 2 -haloalkyl; and R 37  is, in addition, C 1 -C 8 alkylcarbonyl.  
     
     
         6 . A composition according to  claim 5 , wherein G is hydrogen, —C(X,)—R 30 , —C(X 2 )—X 3 —R 31 , —C(X 4 )—NR 32 (R 33 ), —S(O) 2 —R 34 , —P(X 5 )R 35 R 36 , —CH 2 —X 6 —R 37  or an alkali metal, alkaline earth metal, sulfonium or ammonium cation; X,, X 2 , X 3 , X 4 , X 5  and X 6  are, each independently of the others, oxygen or sulfur; R 30 , R 31 , R 32 , R 33 , R 34 , R 35 , R 36  and R 37  are, each independently of the others, hydrogen, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 2 -C 5 alkenyl, C 2 -C 5 haloalkenyl, C 3 -C 8 cycloalkyl, C 3 -C 7 cycloalkyl-C 1 -C 2 alkyl, C 1 -C 4 alkoxy-C 1 -C 4 alkyl, phenyl, heteroaryl, phenyl-C 1 -C 2 alkyl, heteroaryl-C 1 -C 2 alkyl, phenoxy-C 1 -C 2 alkyl or heteroaryloxy-C 1 -C 2 alkyl; R 34 , R 35  and R 36  are, in addition, C 1 -C 6 alkoxy, C 1 -C 3 alkylamino or di(C 1 -C 3 alkyl)amino; and R 37  is, in addition, C 1 -C 8 alkylcarbonyl.  
     
     
         7 . (canceled)  
     
     
         8 . A method of selectively controlling weeds and grasses in crops of useful plants, which comprises treating the useful plants, their seeds or seedlings or the crop area thereof with, simultaneously or separately, a) a herbicidally effective amount of a herbicide of formula I as claimed in  claim 1 , b) an amount, which is effective for antagonism of the herbicide, of a safener of formula IIb and, optionally, c) an additive comprising an oil of vegetable origin or an alkylated derivative thereof, or a mineral oil or a mixture thereof.  
     
     
         9 . A method according to  claim 8 , which comprises treating crops of useful plants or crop areas for crops of useful plants with from 0.001 to 2 kg/ha of a herbicide of formula I and an amount of from 0.001 to 0.5 kg/ha of a safener of formula IIb.  
     
     
         10 . A method according to  claim 8 , wherein the crops of useful plants are cereals, maize and sorghum.  
     
     
         11 . A composition according to  claim 1 , which also comprises, in addition to the formulation adjuvants, an oil additive in the form of a vegetable oil concentrate consisting of the 4 components (A) from 20 to 90% by weight of an alkyl ester of a higher fatty acid (C 4 -C 22 ), (B) from 4 to 40% by weight of an anionic surfactant, (C) from 2 to 20% by weight of a higher fatty acid (C 10 -C 20 ), and (D) up to 140% by weight, based on the total amount of components (A) to (C), of a hydrocarbon.  
     
     
         12 . A composition according to  claim 11 , wherein (A) is a C 1 -C 4 alkyl ester of a C 12 -C 18  fatty acid, (B) is an anionic surfactant of the dodecylbenzylsulfonate type, (C) is a C 12 -C 18  fatty acid, and (D) is an aromatic hydrocarbon.