Nova Patents
IL61579A

Pyrimidinyl-and triazinylamino(thio)carbonylaminosulfonylbenzoic acid derivatives and their use as herbicides and plant growth regulants

Abstract

This record has no abstract on file.

IL61579A, drawing sheet 1
Sheet 1 of 127

Term

No projected expiry on record.

  1. Priority
  2. Filed
  3. Published
  4. Today

5 claims: 4 independent, 1 dependent

  1. 1
    WHAT IS CLAIMED IS:A compound 1. wherein Q is when selected from 0. S or NS02NCN5! I . CQR 11 . 0 (I) is 0 or S then R is C^-C^ alkyl;. n alkenyl;C--C- alkyl substituted with 1u z ם four substituents selected from 0-3 v 3 one to atoms of F, Cl, Br, 0-2 methoxy groups and 0-1 cyanc groups;-CH 2 CN;-CH 2 CO 2 CH 3 ;-CH 2 CO 2 C-Hg;C 3 ־Cg alkenyl substituted with 1-3 atoms of F, Cl, Br;Cg-Cg cycloalkyl;C 5 ־Cg cycloalkenyl;Cg-Cg cycloalkyl substituted with any of one to four methyl groups, OCH 3 , alkyl of C 2 «C 4 , F, Cl or Br;C4-C10 cycloalkylalkyl;C 4 < 8 cycloalkylalkyl with 1-2 CSg;bicycloalkyl;C 7 < 10 bicycloalkenyl;C^q tricycloalkyl , C^q tricycloalkenyl;R 11 where R^ -CH-(CH,) • * n «9 : χ < 3 alkyl R 10 or hydrogen, C x -C 3 alkyl, be taken together to — 0. — CT ׳ and n is 0, 1, 2 or of carbon atoms is £12;R 10 independently hydrogen, . Cl, fcr. -OCH 3 , -OC 2 H 5 , form a 5 or S ־ נ°־ — O J 3 provided the member ring: total number x A is 0, S;Α χ is 0, S, SO 2 ;1) R is also C 3 -C 10 alkynyl;C 3 -C g alkynyl substituted with F, Cl or Br;״ R10 -CH-C-0 (C.-C, alkyl);or -/ (Qj CH 3 R n where R 10 and R χ are as previously defined;when Q is 0, then R is Η, M, -CH 2 CH 2 OR 7׳ -CH 2 CH 2 CH 2 0R 7 , -CHCH 2 OR 7 where R- is -CH 2 CH 3 , ch 3 -CH(CH 3 ) 2 , phenyl, -CH 2 CH 2 C1, -CH 2 CC1 3 ;4CH 2 CH 2 O^ n ,R 8 , where R g is -CH 3 , =¾ -CHjCHj, -CH(CH 3 ) 2 , phenyl, -CHjCHjCl, -CBjCClj, and n’ is 2 or 3;provided R has a total number of carbon atoms £13. ( ? } 0,2 ' ( ? } 0,2 -CHjCHj-S-Rj^ -CH 2 CH 2 CH 2 -S-R 12 ;where £ רו is -CH,, -CH-CH,, -CH(CH,)_, or phenyl;X* w *J «3 X and
  2. 2
    2) R is also CHjOR^ where Rg is CH 3 -,.CH 3 .CH 2 , (CH 3 ) 2 CH-,.C1CH 2 CH 2 - 1 .C1 3 CCH 2 t phenyl ׳ CH,CH.OCH_CH_ or CH-OCH.CH-;.J 4» 4t 4» □ 4* £ where and R^^ are as previously defined;when Q is -N- then R is hydrogen;C־.-C, ר alkyl;I 1 14 R s fCH 2 CH 2 O> nI hR^ 2 ;־CH 2 CH 2 CH 2 OR 12 where R^ 2 is 3ג defined above and n’ is 1-3;C 3 < 10 alkenyl;c 3“Cg cycloalkyl;C 5 ־Cg cycloalkenyl;C s -C g cycloalkyl substituted with 1 to 3 substituents selected from 0-2 -OCH 3 , 0-3 -CH 3 or -C 2 H 3 ;trifluoromethylcyclohexyl;C 4 -C^ Q cycloalkylalkyl;C 4 ־C g cycloalkylalkyl substituted with 1-2 -CH 3 ;-CH 2 CN;-CH 2 CH 2 CN? ? H 3 /—Vz ho -C-CN;-OCH-;-N(CH-)-;“CH(CH,) -<CQ • 3 3 2 1 2 n p CH 3 R 9 11 where R' is hydrogen, C^-C 4 alkyl, -OCH 3 , F, Br, ci, -cf 3 , cn, no 2 , -so 2 ch 3 , -sch 3 , -n(ch 3 ) 2 ;R'' is hydrogen, C^-C 4 alkyl, -OCH 3׳ F, Br, Cl;R'י' is hydrogen, -CH 3׳ Cl, F or Br;Rg is hydrogen,C^-Cg alkyl, allyl, -CHjCN;or -CHjCHjCN;or Rg and R can be taken together to form -(CH 2 )j ;-(CH 2 )g, -(CH 2 )g, -CH 2 CH 2 OCH 2 CH 2 -;LU -CH2CH2NCH2CH-2 ׳ with the proviso that-when-R is -CCH^ or x or or OCH-CH- then R r is H or -CH-.;when R- is -CH״CH_CN 2 3 o 3 0 2 2 or -CH 2 CN then R is -CH 2 CH 2 CN or CH 2 CN;and R and Rg have a total number of carbon atoms £13.
  3. 3
    3) R is also C 3 -C g alkynyl;X X N—/ N—/ N—N R 2 is H, Cl, Br, F, C x -C 3 alkyl, -NOj, -SO 2 CH 3׳ -och 3 , -sch 3 , -cf 3 , -n(ch 3 ) 2 , -nh 2 , or -CN;R 3 is H, Cl, Br, F or CH 3 ;R 4 is H, or -CH 3 ;Rg is H, -CH 3 , or -OCH 3 ;M is an alkali metal;W is oxygen or sulfur;X is H, Cl, -CH 3 , -OCH 3 , -OCH 2 CH 3 or -OCH 2 CH 2 OCH 3 ;Y is H,’ Cl;C^-C 4 alkyl;C^-C 4 alkyl substituted with .OCH 3 , -OC 2 H.,-CN, -CQ 2 CH 3 , -COjCjHg, or 1 to 3 atoms of F, Cl, Br;C 3 ־C 4 alkenyl;-CH 2 CSCR i3 where R 13 is H, -CH 3 , -CHjCl;-A-iCHjJjjrA! -(C^-Cg alkyl), and n', A and A^ are as previously defined;0 0 O -ACH 2 C-L;-ACHC-L;-ACH 2 CH 2 C-L, where L is -NH 2׳ έπ 3 -NCH 3 , -NH(C 1 -C 4 alkyl), -N(C 1 ־C 4 alkyl) 2׳ och 3 x C x -Cg alkoxy CHj and R« 7 is H;SCI;-N 3 ;viiere R^g is H or -OCH 3 ;C x ־C 4 alkyl;C x -C 4 alkyl substituted with -CN, -CO 2 CH 3 , CO 2 C 2 H 3 ;C 3 ~C 4 alkenyl? or C 2 ־C 3 alkyl substituted with -OCH 3׳ OCjHj;or R^g and R^ 7 can be taken together to fora -CH 2 CH 2 CH 2 CH 2 ־, -CH 2 CH 2 OCH 2 CH 2 ־;-O-R x4 where Κ χ4 is C X «C 4 alkyl;C 2 -C 4 alkyl substituted with 1-3 atoms of F, Cl or 3r;Cj-C 4 alkyl substituted with cyano;C 3 ~C 4 alkenyl, -O^C^Ot-;where is as previously defined;-CH 2 —;“SR x 5 where β χ5 is Cj-C 4 alkyl, C^-Cj alkyl substituted with CN, allyl, propargyl;with the provision that when Y is >4 carbon atoms, R is <4 carbon atoms, when X is Cl, then Y is Cl, and when X and Y are both H, then R is <4 carbon atoms.
  4. 4
    4) Y is also F;Br;° A L ;C X ־C 4 alkyl substituted with L.' where L' is NH^ OH, NCH 3 , NH(C 1 ־C 4 alkyl), och 3 N(C x -C 4 alkyl) 2 or C 3 ־C g alkoxy;NR 16 R 17' where R 17' is C 5‘ C 6 alkyl or C X ~C 4 alkyl substituted with 0 L is also OH;Z is CH or N;Υ χ is H, -OCH 3 , -CH 3 ;
  5. 5
    5) Y£ is also OCH 2 CH 3 ; and X Χ χ is Η, Cl, -CCH 3 , -OCH 2 CH 3 ,-ch 3 ; providing that X^ and are not both Simultaneously hydrogen and when R^ is 1 I Y 1 then and R- are both H and R is £5 carbon atoms, and a) when Y is not as defined in 4), then , R must be as defined in 1), 2) or 3; b ) when Y^ is not as defined in 5), then R must be as defined in 1), 2) or 3. X 2. A compound of Claim 1 in which Y and R- are H; and W is 0. 3. A compound of Claim 2 in which Q is oxygen. 10 4. A compound of Claim 3 in which R is C^-C^ alkyl, C 3 -C 4 alkenyl, CH 2 CH 2 C1, CH 2 CH 2 0CH 3 or CH 2 0R 'g. 5. A compound of Claim 4 in which X is CH^ or och 3 . 1:6. A compound of Claim 5 in which Y is CH^, 0CH 3 or 0 I \ CH 3 oh 7. A compound of Claim 6 in which R^ is H. 20 8. A compound of Claim 7 in which R 2 is H. 9. A compound of Claim 8 in which R׳g is CH, or CH 3 CH 2 and R is CH 3 , CH 2 CH 2 0CH 3 or ch 2 ch 2 oc 2 h 5< 25 10. A compound of Claim 1, C(2-methoxyethoxy)methyl] 2-[ [(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyljbenzoate. 11. A compound of Claim 1, [(2-methoxyethoxy)methyl] 2-([ (4-ethoxy-6-methy1-1,3,5-triazin-2-yl)aminocarbonyl]30 aminosulfonyl]benzoate. x 121 12. A compound of Claim 1, ’[”(4־-chlorophenoxy)methyl] 2-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoate. 13. A compound of Claim 1, methyl 2-[[[4-(1-carboxy5 ethoxy)-6-methyl-l,3,5-triazin-2-yl]aminocarbonyl]amino- sulfonyl]benzoate. 14. A compound of Claim 1, [(2-methoxyethoxy)methyl] 2-[[(4,6-dimethylpyrimidin-2-y1)aminocarbonyl]aminosulfonyl]benzoate. 10 15. A compound of Claim 1, (4-chloro-2-butynyl) 2-[[(4-methoxy-6-methy Ipyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoate. 16. A composition suitable for controlling the growth of undesired vegetation which comprises an 15 effective amount of a compound of Claim 1 and at least one of the following: surfactant,. solid or liquid diluent. 17. A compositiqn suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of Claim 2 and at least one 20 of the following: surfactant, solid or liquid diluent. 18. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of Claim 3 and at least one of the following: surfactant, solid or liquid diluent. 25 19. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of Claim 4 and at least one of the following: surfactant, solid or liquid diluent. 20. A composition suitable for controlling the 30 growth of undesired vegetation which comprises an effective amount of a compound of Claim 5 and at least one of the following: surfactant, solid or liquid diluent. x 122 21. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of Claim 6 and at least one of the following: surfactant, solid or liquid diluent. 5 22. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of Claim 7 and at least one of the following: surfactant, solid or liquid diluent. 23. A composition suitable for controlling the 10 growth of undesired vegetation which comprises an effective amount of the compound of Claim S and at least one of the following: surfactant, solid or liquid diluent 24. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be 1- protected an effective amount of a compound of Claim 1. 25. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 2. 26. A method for controlling the growth of undesired 20 vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 3. 27. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 4. 2, 5 28. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 5. 29. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be 3 θ protected an effective amount of a compound of Claim 6. 30. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 7. 31. A method for controlling the growth of undesired 35 vegetation which comprises applying to the locus to be protected an effective amount of the compound of Claim 8.
Independent claims5