Herbicidal Pyridino-/Pyrimidino-Thiazoles

Abstract

The present invention relates to herbicidally active pyridino-/pyrimidino-thiazole derivatives, as well as to processes and intermediates used for the preparation of such derivatives. The invention further extends to herbicidal compositions comprising such derivatives, as well as to the use of such compounds and compositions in controlling undesirable plant growth: in particular the use in controlling weeds, in crops of useful plants.

1 . A method of controlling unwanted plant growth, comprising applying a compound of formula (I) 
       
         
           
           
               
               
           
         
         or a salt or N-oxide thereof, wherein, 
         X 1  is N or CR 1 ; 
         R 1  is hydrogen, halogen, cyano, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkoxy, —C(O)OR 6  or S(O) n (C 1 -C 6 alkyl), formyl, hydroxyl, —C(O)NR 6 R 7 , NR 6 R 7 , benzyloxy, C 1 -C 6  haloalkoxy, or C 1 -C 6  haloalkyl; 
         R 2  is hydrogen, halogen, cyano, nitro, C 1 -C 6  alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6  alkynyl, C 3 -C 6 cycloalkyl, —C(O)OR 6 , S(O) n (C 1 -C 6 alkyl), C 1 -C 6  alkoxy, or C 1 -C 6  haloalkoxy; 
         n is 0, 1, or 2; 
         R 3  is hydrogen, cyano, C 1 -C 6 alkyl, C 2 -C 6  alkenyl, C 2 -C 6  alkynyl, C 2 -C 6 haloalkenyl, C 1 -C 6  alkoxy, C 1 -C 6  haloalkyl, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyloxy, C 3 -C 10 cycloalkyl, NR 6 R 7 , 
         R 4  is O, S, or N(C 1 -C 6 alkyl); 
         X 2  is O, S, or NR 8 ; 
         R 5  is hydrogen, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 10 cycloalkyl, C 3 -C 10 cycloalkenyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 alkynyloxy, C 3 -C 10 cycloalkyloxy, C 3 -C 10 cycloalkenyloxy, C 2 -C 6 haloalkenyloxy, C 6 -C 10 aryl or C 6 -C 10 aryl substituted by from 1 to 3 groups independently selected from halogen, nitro, cyano, C 1 -C 3  alkyl, C 1 -C 3  alkoxy, C 1 -C 3  haloalkyl, and C 1 -C 3  haloalkoxy; C 3 -C 10 heterocylcyl or C 3 -C 10 heterocyclycl substituted by from 1 to 3 groups independently selected from halogen, nitro, cyano, C 1 -C 3  alkyl, C 1 -C 3  alkoxy, C 1 -C 3  haloalkyl, and C 1 -C 3  haloalkoxy; or NR 6 R 7 ; 
         or R 3  and R 5  together with X 2  and the atoms to which they are attached, form a saturated or partially unsaturated 5-9 membered ring system optionally comprising 1 to 3 heteroatoms independently selected from S, O and N and optionally substituted with 1 to 3 groups independently selected from halogen or C 1 -C 6  alkyl; 
         or R 3  and R 8  together with the atoms to which they are attached form a saturated or partially unsaturated 5-9 membered ring system optionally comprising 1 to 3 heteroatoms independently selected from S, O and N and optionally substituted with 1 to 3 groups independently selected from halogen or C 1 -C 6  alkyl; 
         R 6  and R 7  are each independently hydrogen, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 2 -C 6  alkenyl, or C 2 -C 6  alkynyl, 
         or R 4  and R 5  together with X 2  and the atoms to which they are attached, form a saturated or partially unsaturated 5-9 membered ring system optionally comprising 1 to 3 heteroatoms independently selected from S, O and N and optionally substituted with 1 to 3 groups independently selected from halogen or C 1 -C 6  alkyl; 
         or R 6  and R 7  together with the nitrogen atom to which they are attached form a saturated or partially unsaturated 3-6 membered ring optionally comprising 1 to 3 heteroatoms independently selected from S, O and N and optionally substituted with 1 to 3 groups independently selected from halogen or C 1 -C 6  alkyl; 
         R 8  is hydrogen, cyano, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 2 -C 6  alkenyl, or C 2 -C 6  alkynyl; C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 alkynyloxy, C 3 -C 10 cycloalkyloxy, C 3 -C 10 cycloalkenyloxy, C 2 -C 6 haloalkenyloxy; 
         or R 7  and R 8  together with the carbon atoms to which they are attached form a saturated or partially unsaturated 3-9 membered ring optionally comprising 1 to 3 heteroatoms independently selected from S, O and N and optionally substituted with 1 to 3 groups independently selected from halogen or C 1 -C 6  alkyl, 
         to the unwanted plants or to the locus thereof. 
       
     
     
         2 . The method according to  claim 1 , wherein R 1  is hydrogen, halogen, formyl, cyano, C 1 -C 6  alkoxy, C 1 -C 6  alkylsulfonyl, C 1 -C 6  alkylthio, C 1 -C 6  haloalkoxy, —C(O)NR 6 R 7 , NR 6 R 7 , or C 1 -C 6  haloalkyl 
     
     
         3 . (canceled) 
     
     
         4 . The method according to  claim 1 , wherein R 2  is halogen, cyano, nitro, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 2 -C 6  alkenyl, C 1 -C 6  alkylsulfinyl, C 1 -C 6  alkylsulfonyl, C 1 -C 6  alkylthio, —C(O)OR 6 , C 1 -C 6  alkoxy, C 1 -C 6  haloalkoxy, C 3 -C 6  cycloalkyl, or C 2 -C 6  alkynyl 
     
     
         5 . (canceled) 
     
     
         6 . The method according to  claim 1  wherein R 3  is C 1 -C 6  alkyl, C 2 -C 6  alkenyl, C 2 -C 6  alkynyl, C 2 -C 6  haloalkenyl, C 1 -C 6  alkoxy, C 1 -C 6  haloalkyl, C 1 -C 6  haloalkoxy, C 2 -C 6  alkenyloxy, C 3 -C 10  cycloalkyl, or NR 6 R 7 . 
     
     
         7 . (canceled) 
     
     
         8 . The method according to  claim 1  wherein R 5  is C 1 -C 6  alkyl, C 2 -C 6  alkenyl, C 2 -C 6  alkynyl, C 3 -C 10  cycloalkyl, C 1 -C 6  haloalkyl, C 2 -C 6  haloalkenyl, C 1 -C 6  alkoxy, C 1 -C 6  haloalkoxy, C 2 -C 6  alkenyloxy, C 2 -C 6  alkynyloxy, C 3 -C 10  cycloalkyloxy, C 3 -C 10  cycloalkenyloxy, C 2 -C 6  haloalkenyloxy, C 6 -C 20  aryl, C 3 -C 20  heterocylcyl, or NR 6 R 7 . 
     
     
         9 . The method according to  claim 1 , wherein R 3  and R 5  together with X 2  and the atoms to which they are attached, form a ring system Q, selected from the group consisting of Q 1  and Q 2 , 
       
         
           
           
               
               
           
         
       
       wherein X 2  and R 4  are as defined in  claim 1 , and A denotes the point of attachment to the pyridino/pyrimidino-thiazole moiety. 
     
     
         10 . (canceled) 
     
     
         11 . The method according to  claim 1  wherein R 4  is O. 
     
     
         12 . The method according to  claim 1  wherein X 2  is O, or NR 8 . 
     
     
         13 . (canceled) 
     
     
         14 . (canceled) 
     
     
         15 . (canceled) 
     
     
         16 . A herbicidal composition comprising from 0.1 to 99% by weight, of a compound of Formula (I) as defined in  claim 1 , and from 1 to 99.9% by weight of a formulation adjuvant, wherein the formulation adjuvant comprises from 0 to 25% by weight of a surface-active substance. 
     
     
         17 . (canceled) 
     
     
         18 . The herbicidal composition of  claim 16 , further comprising at least one additional pesticide selected from a herbicide or herbicide safener. 
     
     
         19 . (canceled) 
     
     
         20 . (canceled) 
     
     
         21 . A method of selectively controlling weeds at a locus comprising crop plants and weeds, wherein the method comprises application to the locus, of a weed-controlling amount of (i) a compound of formula (I): 
       
         
           
           
               
               
           
         
         or a salt or N-oxide thereof, wherein, 
         X 1  is N or CR 1 ; 
         R 1  is hydrogen, halogen, cyano, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkoxy, —C(O)OR 6  or S(O) n (C 1 -C 6 alkyl), formyl, hydroxyl, —C(O)NR 6 R 7 , NR 6 R 7 , benzyloxy, C 1 -C 6  haloalkoxy, or C 1 -C 6  haloalkyl; 
         R 2  is hydrogen, halogen, cyano, nitro, C 1 -C 6  alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6  alkynyl, C 3 -C 6 cycloalkyl, —C(O)OR 6 , S(O) n (C 1 -C 6 alkyl), C 1 -C 6  alkoxy, or C 1 -C 6  haloalkoxy; 
         n is 0, 1, or 2; 
         R 3  is hydrogen, cyano, C 1 -C 6 alkyl, C 2 -C 6  alkenyl, C 2 -C 6  alkynyl, C 2 -C 6 haloalkenyl, C 1 -C 6  alkoxy, C 1 -C 6  haloalkyl, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyloxy, C 3 -C 10 cycloalkyl, NR 6 R 7 , 
         R 4  is O, S, or N(C 1 -C 6 alkyl); 
         X 2  is O, S, or NR 8 ; 
         R 5  is hydrogen, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 10 cycloalkyl, C 3 -C 10 cycloalkenyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 alkynyloxy, C 3 -C 10 cycloalkyloxy, C 3 -C 10 cycloalkenyloxy, C 2 -C 6 haloalkenyloxy, C 6 -C 10 aryl or C 6 -C 10 aryl substituted by from 1 to 3 groups independently selected from halogen, nitro, cyano, C 1 -C 3  alkyl, C 1 -C 3  alkoxy, C 1 -C 3  haloalkyl, and C 1 -C 3  haloalkoxy; C 3 -C 10 heterocylcyl or C 3 -C 10 heterocyclycl substituted by from 1 to 3 groups independently selected from halogen, nitro, cyano, C 1 -C 3  alkyl, C 1 -C 3  alkoxy, C 1 -C 3  haloalkyl, and C 1 -C 3  haloalkoxy; or NR 6 R 7 ; 
         or R 3  and R 5  together with X 2  and the atoms to which they are attached, form a saturated or partially unsaturated 5-9 membered ring system optionally comprising 1 to 3 heteroatoms independently selected from S, O and N and optionally substituted with 1 to 3 groups independently selected from halogen or C 1 -C 6  alkyl; 
         or R 3  and R 8  together with the atoms to which they are attached form a saturated or partially unsaturated 5-9 membered ring system optionally comprising 1 to 3 heteroatoms independently selected from S, O and N and optionally substituted with 1 to 3 groups independently selected from halogen or C 1 -C 6  alkyl; 
         R 6  and R 7  are each independently hydrogen, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 2 -C 6  alkenyl, or C 2 -C 6  alkynyl, 
         or R 4  and R 5  together with X 2  and the atoms to which they are attached, form a saturated or partially unsaturated 5-9 membered ring system optionally comprising 1 to 3 heteroatoms independently selected from S, O and N and optionally substituted with 1 to 3 groups independently selected from halogen or C 1 -C 6  alkyl; 
         or R 6  and R 7  together with the nitrogen atom to which they are attached form a saturated or partially unsaturated 3-6 membered ring optionally comprising 1 to 3 heteroatoms independently selected from S, O and N and optionally substituted with 1 to 3 groups independently selected from halogen or C 1 -C 6  alkyl; 
         R 8  is hydrogen, cyano, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 2 -C 6  alkenyl, or C 2 -C 6  alkynyl; C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 alkynyloxy, C 3 -C 10 cycloalkyloxy, C 3 -C 10 cycloalkenyloxy, C 2 -C 6 haloalkenyloxy; 
         or R 7  and R 8  together with the carbon atoms to which they are attached form a saturated or partially unsaturated 3-9 membered ring optionally comprising 1 to 3 heteroatoms independently selected from S, O and N and optionally substituted with 1 to 3 groups independently selected from halogen or C 1 -C 6  alkyl.