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1. WO1992016510 - NOUVEAUX COMPOSES POSSEDANT UNE EFFICACITE HERBICIDE, INSECTICIDE ET ACARICIDE

Note: Texte fondé sur des processus automatiques de reconnaissance optique de caractères. Seule la version PDF a une valeur juridique

[ EN ]

WHAT IS CLAIMED IS:
1. A pyrazolidine-3,5-dione of the formula I


o

in which

R1 is



R2 and R3 independently of one another are C1-C6alkyl; C3-C6alkenyl; or C3-C6alkynyl; or R2 and R3 together are a -(CH2)3-, -(CH2)4-, -CH2-CH=CH-CH2-, -CH2-CH=CH- or
-(CH2)2-CH=CH- bridge which is unsubstituted or up to trisubstituted by
C1-C4aIkyI;
n is 0; 1; 2; 3; or 4;
m is 0; or 1; the total of m and n being less than, or equal to, 4; the
R4 radicals independently of one another are halogen; nitro; cyano, C1-C4alkyl;
C1-C4haloalkyI; C1-C10alkoxy; C1-C4haloalkoxy; C3-C6alkenyloxy;
C1-C4alkoxy- C2-C4alkoxy; C3-C6alkynyloxy; C1-C4alkylcarbonyl;
C1-C4alkoxycarbonyl; C1-C4alkyIthio; C1-C4alkylsulfinyl; C1-C4alkylsulfonyl;
amino; mono-C1-C4alkylamino; di- C1-C4alkylamino;

R5 is



X is oxygen: sulfur; CH2; or NR7;
o is 0; 1; 2; or 3;
R6 radicals independently of one another are C1-C4alkyl; halogen; C1-C4haIoalkyl;
C1-C4haloalkoxy; C1-C4alkoxy; nitro; cyano; C1-C4alkoxycarbonyl; amino;
mono-C1-C4alkylamino; or di-C1-C4alkylamino; and
R7 is hydrogen; C1-C4alkyl; formyl; or C1-C4alkylcarbonyl,
or a acid addition salt thereof.

2. A pyrazolidine-3,5-dione according to claim 1, of the formula I
in which


R1 is



n is 0; 1; 2; 3; or 4;
m is 0; or 1; and the total of m and n is less than, or equal to, 4;
n' is 0; 1; 2; or 3;
n" is 0; 1; or 2;
m' is 0; or 1; and the total of m' and n' is less than, or equal to, 3; and
the radicals R1 to R5 are as defined above.

3. A pyrazolidine-3,5-dione according to claim, of the formula I


in which

R1 is


R2 and R3 independently of one another are C1-C6alkyl; C3-C6alkenyl; or C3-C6alkynyl; or R2 and R3 together are a -(CH2)3-, -(CH2)4-, -CH2-CH=CH-CH2-, -CH2-CH=CH- or
-(CH2)2-CH=CH- bridge which is unsubstituted or up to trisubstituted by
C1-C4alkyl;

n is 0; 1; 2; 3; or 4;
m is 0; or 1; the total of m and n being less than, or equal to, 4;
R4 radicals independently of one another are halogen; nitro; cyano; C1-C4alkyl;
C1-C4haloaIkyl; C1-C4alkoxy; C1-C4haloalkoxy; C3-C6alkenyloxy;
C3-C6alkynyloxy; C1-C4alkylcarbonyl; C1-C4alkoxycarbonyl; C1-C4alkyIthio;
C1-C4aIkylsulfinyl; C1-C4alkylsulfonyl; amino; mono-C1-C4alkylamino;
di-C1-C4alkylamino;

R5 is


X is oxygen; sulfur; CH2; or NR7;
o is 0; 1; 2; or 3;
R6 radicals independently of one another are C1-C4alkyI; halogen;
C1-C4haloalkyI;C1-C4haloalkoxy; C1-C4alkoxy; nitro; cyano;
C1-C4alkoxycarbonyl; amino; mono-C1-C4alkylamino; or di-C1-C4alkylamino; and R7 is hydrogen; C1-C4aIkyl; formyl; or C1-C4alkylcarbonyl

4. A pyrazolidine-3,5-dione according to claim 3, of the formula I


in which

R1 is


n is 0; 1; 2: 3; or 4;
m is 0; or 1: and the total of rn and n is less than, or equal to, 4;
n' is 0; 1; 2; or 3;
m' is 0; or 1; and the total of m' and n' is less than, or equal to, 3;
and the radicals R2 to R5 are as defined above.

5. A 5,6,7,8-tetrahydro-1H-pyrazolo[1,2-a]pyridazine-1,3(2H)- dione according to claim 3, of the formula la



in which
R8 is C1-C4alkyl; and
p is 0, 1, 2 or 3, preferably 0.

6. A 5,8-dihydro-1H-pyrazolo[1,2-a]pyridazine-1,3(2H)-dione, according to claim 3, of the formula lb



in which
R8 is C1-C4alkyl; and
p is 0, 1, or 2, preferably 0.

7. A 7,8-dihydro-1H-pyrazolo[1,2-a]pyridazine-1,3(2H)-dione, according to claim 3, of the formula Ic



in which
R8 is C1-C4alkyl; and
p is 0, 1, 2 or 3, preferably 0.

8. A 6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazole-1,3(2H)-dione, according to claim 3, of the formula Id

in which
R8 is C1-C4alkyl; and
p is 0, 1 , 2 or 3, preferably 0.

9. A 1H,5H-pyrazolo[1,2-a]pyrazole-1,3(2H)-dione, according to claim 3, of the formula Ie



in which
R8 is C1-C4alkyl; and
p is 0, 1, 2 or 3, preferably 0.

10. A pyrazolidine-1,3-dione, according to claim 3, of the formula If



in which
R2 and R3 independently of one another are C1-C6alkyl; C3-C6alkenyl; or C3-C6alkynyl.

1 1. A pyrazolidine-1,3-dione, according to claim 3, of the formula Ig



in whicc R2 and R3 independently of one another are C1-C6alkyl; or C3-C6alkenyl.

12. A pyrazolidine-1,3-dione, according to claim 3, of the formula Ih



in which
R2 and R3 are C1-C6alkyl.

13. A compound according to one of claims 5 to 12, in which

R1 is and


n' is 0; 1; 2; or 3;
m' is 0; or 1; and the total of m' and n' is less than, or equal to, 3;
R4 is not more than three times halogen; or C1-C4alkyl;
not more than twice C1-C4alkoxy; C1-C4haloalkoxy; C1-C4alkylthio;
C1-C4alkylsulfinyl; C1-C4alkylsulfonyl; amino; mono-C1-C4alkylamino;
di-C1-C4alkylamino; or C1-C4haloalkyl; and
not more than once nitro; cyano; C1-C4alkylcarbonyl; C1-C4alkoxycarbonyl; or

R1 is


n is 0; 1; 2; 3; or 4;
m is 0; or 1 ; and the total of m and n is less than, or equal to, 4;
R4 is not more than four times halogen; or C1-C4alkyl;
not more than three times C1-C4alkoxy; C1-C4haloalkoxy; or C1-C4alkylthio; and not more than twice nitro; C1-C4alkylsulfinyl; C1-C4alkylsulfonyl; amino;
mono-C1-C4alkylamino; di-C1-C4alkylamino; C1-C4haloalkyl; or cyano;
not more than once C1-C4alkylcarbonyl; C3-C6alkenyloxy; C3-C6alkynyloxy;
C1-C4alkoxycarbonyl; and
R5 is as defined under claim 1 or 2, and the meaning of the substituent R4 can in each case be identical or different.

14. A compound as claimed in one or more of claims 3 to 13, in which

R1 is and


n' is 0; 1; 2; or 3;
m' is 0;
R4 is not more than three times halogen; or C1-C4alkyl;
not more than twice C1-C4alkoxy; C1-C4haloalkyl; C1-C4haloalkoxy;
C1-C4aIkylthio; C1-C4alkylsulfιnyl; C1-C4alkylsulfonyl; amino;
mono-C1-C4aIkylamino; or di-C1-C4alkylamino; and
not more than once nitro; cyano; C1-C4alkylcarbonyl; C1-C4alkoxycarbonyl; or

R, is


n is 0; 1; 2; or 3;
m is 0; or 1 ; and the total of m and n is less than, or equal to, 3;
R4 is not more than three times fluorine; chlorine; or C1-C4alkyl;
not more than twice C1-C4alkoxy; C1-C4haloalkyl; C1-C4haloalkoxy; or
C1-C4alkylthio; and
not more than once nitro; C1-C4alkylsulfinyl; C1-C4alkylsulfonyl; amino;
mono-C1-Qalkylamino; di- C1-C4alkylamino; cyano; C1-C4alkylcarbonyl;
C3-C6alkenyloxy; C3-C6alkynyloxy; or C1-C4alkoxycarbonyl; and the meaning of the substituent R4 can in each case be identical or different.

15. A compound as claimed in one or more of claims 3 to 14, in which

R, is and


n' is 0; 1; 2; or 3;
m' is 0;
R4 is not more than three times fluorine; chlorine; or C1-C2alkyl;
not more than twice C1-C2alkoxy; C1-C2haloaIkyl; C1-C2haloalkoxy;
C1-C2aIkylthio; C1-C2alkylsuIfinyl; C1-C2alkylsulfonyl; amino;

mono-C1-C2alkylamino; or di-C1-C2alkylamino; and
not more than once nitro; cyano; C1-C2alkylcarbonyl; C1-C2alkoxycarbonyl; or

R1 is


n is 0; 1; 2; or 3;
m is 0; or 1; and the total of m and n is less than, or equal to, 3;
R4 is not more than three times fluorine; chlorine; or C1-C4alkyl;
not more than twice C1-C2alkoxy; C1-C2haloalkyl; C1-C2haloalkoxy; or
C1-C2alkylthio; and
not more than once nitro; C1-C2alkylsulfinyl; C1-C2alkylsulfonyl; amino;
mono- C1-C2alkylamino; di- C1-C2alkylamino; cyano; C1-C2alkylcarbonyl;
C1-C2alkoxycarbonyl; and the meaning of the substituent R4 can in each case be identical or different.

16. A pyrazolidine-3,5-dione according to claim 1, of the formula I



in which R1 can be the following groups


in which R2, R3, R4, R5, m and n are as defined in claim 1 and R9 is halogen, C1-C4alkyl or C1-C4haloalkyl, the total of m + n being less than, or equal to, 3.

17. A pyrazolidine-3,5-dϊone according to claim 1, in which Rj has the meaning given in claim 16 and R2 is methyl and R3 is methyl or ethyl, or R2 and R3 together are -(CH2)3-, -(CH2)4- or .



18. A pyrazolidine-3,5-dione of the formula I according to claim 1, in which R1 is

R,



in which
R9 is halogen; C1-C4alkyl; C1-C4haloalkyl;
R10 is hydrogen; halogen; C1-C4alkyl; C1-C4haloalkyl and
R11 is hydrogen; halogen or C1-C4alkyl.

19. A pyrazolidine-3,5-dione according to claim 17, in which R1 is 2-naphthyl or



in which,
R9 is chlorine; C1-C2alkyl; C1-C2haIoaIkyI;
R10 is hydrogen: chlorine; fluorine; C1-C2alkyl or C1-C2haloalkyl; and
R1 1 is hydrogen: fluorine; chlorine or methyl.

20. A compound of the formula Ia according to claim 5, selected from the group comprising
2-(phenyl)-5,6,7,8-tetrahydro-1H-pyrazolo[ 1,2- a]pyridazine-1,3(2H)-dione, 2-(2-methylphenyl)-5,6,7,8-tetrahydro-1H-pyrazolo[1,2-a]pyridazine-1,3(2H)-dione,

2-(4-methylphenyl)-5,6,7,8-tetrahydro-1H-pyrazolo[1,2 -a]pyridazine-1,3(2H)-dione,

2-(2,4,6-trimethylphenyl)-5,6,7,8-tetrahydro-1H-pyrazolo[1,2-a]pyridazine-1,3(2H)-dione,
2-(4-chlorophenyl)-5,6,7,8-tetrahydro-1H-pyrazolo[1,2 -a]pyridazine-1,3(2H)-dione,

2-(2,4-dichlorophenyl)-5,6,7,8-tetrahydro-1H-pyrazolo[1,2 -a]pyridazine-1,3(2H)-dione and
2-(2,6-dichlorophenyl)-5,6,7,8-tetrahydro-1H-pyrazolo[1,2 -ajpyridazine-1,3(2H)-dione,

2-(2,4-dimethylphenyl)-5,6,7,8-tetrahydro-1H-pyrazolo[1,2-a]pyridazine-1,3(2H)-dione,

2-(2-chlorophenyl)-5,6,7,8-tetrahydro-1H-pyrazolo[1,2-a]pyridazine-1,3(2H)-dione,

2-(2-chloro-6-fluorophenyl)-5,6,7,8-tetrahydro-1H-pyrazolo[1,2-alpyridazine-1,3(2H)-dione,
1,2-dimethyl-4-(2,4,6-trimethylphenyl)-3,5-pyrazolidinedione,
in particular 2-(2,4,6-trimethylphenyl)-5,6,7,8-tetrahydro-1H-pyrazolo[ 1,2- a]-pyrid azine-1,3(2H)-dione.

21. A process for the preparation of a compound of the formula I according to one of claims 1 to 19, which comprises

a) the cyclisation of a hydrazinecarboxylate of the formula II,



in which R1, R2 and R3 are as defined above and Y is C1-C6alkyl, phenyl or benzyl;

b) the condensation of a malonic acid derivative of the formula III, in which R1 is as defined above, with a hydrazine derivative of the formula IV, in which R2 and R3 are as defined above,

and in which Y is OH, halogen or C1-C4alkoxy;
or
c) the reaction of a pyrazolidine-3,5-dione of the formula XXXIV


in which the radicals R2 and R3 are as defined above, with a compound of the formula XXXV

X-R1 ((XXV),

in which X and R1 are as defined above, in the presence of a base or in the presence of Cu(I) or of a Pd catalyst.

22. A process for the preparation of a compound of the formula lc and le, according to one or more of claims 7, 9 or 13 to 15, which comprises reacting an alcohol of the formula XIII


in which x is 0 or 1 , in the presence of an acid, to give lc or le.

23. A process for the preparation of a pyrazolidine-1,3-dione of the formula If, according to one or more of claims 10 or 13 to 15, which comprises acylating a hydrazone of the

formula XIV in which R2 is as defined above and the radical is a


C1-C6alkylidene, C1-C6alkenylidene or C1-C6alkynylidene radical, with a chloroformate IX in which Y is C1-C4 alkyl, to give the N-acylhydrazone XV,



and subsequently acylating the N-acylhydrazone with arylacetyl halide of the formula X in which R1 is as defined above and Z is chlorine or bromine, to give a hydrazine of the formula XVI,


and subsequently cyclising the hydrazine of the formula XVI in the presence of a base to give the pyrazolidine-1,3-dione of the formula If.

24. A compound of the formula II

in which the radicals R1, R2 and R3 are as defined in one more of claims 1 to 16 and Y is C1-C6alkyl, phenyl or benzyl.

25. A process for the preparation of a compound of the formula II according to claim 24, which comprises the N-acylation of an N-acylhydrazine of the formula XVII, in which R2 and R3 are as defined above, and Y is C1-C4alkyl, with an arylacetyl halide of the formula X, in which R1 is as defined above and Z is chlorine or bromine,



26. A compound of the formula XVI



in which R1 is as defined in claim 1, Y is C1-C4alkyl and R2 and R3 independently of one another are C1-C6aIkyl, C3-C6alkenyl or C3-C6alkynyl.

27. A process for the preparation of a compound of the formula (XVI) according to claim 26. which comprises acylating a hydrazone of the formula XIV in which R2 is as defined

above and the radical is a Cj-Cgalkylidene, C1-C6alkenylidene or


C1-C6alkynyIidene radical, with a chloroformate IX in which Y is C1-C4alkyl, to give an N-acylhydrazone XV,

and subsequently acylating the N-acylhydrazone with an arylacetal halide of the formula X in which R1 is as defined above and Z is chlorine or bromine, to give a hydrazine of the formula XVI



28. An alcohol of the formula XIII"



in which R1, R8 and p are as defined in claim 1.

29. An N-acylhydrazine of the formula


in which R2 and R3 are as defined in claim 1 and in which Y is C1-C4alkyl.

30. A process for the preparation of a compound according to claim 29. which comprises hvdrolvsing and decarboxylating a hydrazinedicarboxylate XII in which R2 and R3 are as defined above and Y is C1-C4alkyl



31. A tetrahydropyridazinecarboxylate of the formula XXIII


in which R8 and p are as defined in claim 1 and Y is C1-C4alkyl.

32. A process for the preparation of a compound according to claim 31, which comprises reacting a diene of the formula XXIV in which R8 and p are as defined above, with an azodicarboxylate of the formula XXV, in which Y is C1-C4alkyl,



33. A compound of the formula XIV


in which the radical is a C1-C6alkylidene, C1-C6alkenylidene or


C1-C6alkynylidene radical, and R2 is as defined in claim 1.

34. A compound of the formula XV


in which the radical is a C1-C6alkylidene, C1-C6alkenylidene or


C1-C6alkynylidene radical and Y is C1-C4alkyl, and R2 is as defined in claim 1.

35. A compound of the formula XVI



in which R1, R2 and R3 are as defined in claim 1 and Y is C1-C4alkyl.
36. A compound of the formula VII



in which R8 and p are as defined in claim 1 and Y is C1-C4alkyl.
37. A compound of the formula XI


in which R8, R1 and p are as defined in claim 1 and Y is C1-C4alkyl.
38. A compund of the formula XII

in which R8, R1 and p are as defined in claim 1.

39. A compound of the formula XIX


in which R8 and p are as defined in claim 1 and Y is C1-C4alkyl.

40. A compound of the formula XX



in which R8, R1 and p are as defined in claim 1 and Y is C1-C4alkyl.

41. A compound of the formula XXI



in which R8, R1 and p are as defined in claim 1 and Y is C1-C4alkyl.

42. A herbicidal composition, which comprises one or more active ingredients of the formula I according to one of claims 1 to 20.

43. A method of controlling undesirable vegetation, wherein an effective amount of a composition comprising an active ingredient of the formula I according to one of claims 1 to 20 is applied to plants or their environment.

44. A method according to claim 43, for the selective pre- or post-emergence control of weeds in crops of useful plants.

45. An insecticidal or acaricidal composition which comprises one or more active ingredients of the formula I according to one of claims 1 to 20.

46. A method of controlling insects or arachnids, wherein an active ingredient of the formula I according to one of claims 1 to 20 or a composition comprising this active ingredient is applied to the insect, the arachnid or their environment.

47. The use of an active ingredient of the formula I according to one or more of claims 1 to 20 as a herbicide.

48. The use of an active ingredient of the formula I according to one or more of claims 1 to 20 as an insecticide or acaricide.

49. Seed which has been dressed with an insecticidally or acaricidally active amount of an active ingredient of the formula I according to one or more of claims 1 to 20.