MXPA00004809A - Benzylidene pyrazolones and use as herbicide - Google Patents
Benzylidene pyrazolones and use as herbicideInfo
- Publication number
- MXPA00004809A MXPA00004809A MXPA/A/2000/004809A MXPA00004809A MXPA00004809A MX PA00004809 A MXPA00004809 A MX PA00004809A MX PA00004809 A MXPA00004809 A MX PA00004809A MX PA00004809 A MXPA00004809 A MX PA00004809A
- Authority
- MX
- Mexico
- Prior art keywords
- alkyl
- alkoxy
- halogen
- hydrogen
- event
- Prior art date
Links
- -1 Benzylidene pyrazolones Chemical class 0.000 title claims abstract description 341
- 230000002363 herbicidal Effects 0.000 title claims description 20
- 239000004009 herbicide Substances 0.000 title claims description 6
- 229940051880 analgesics and antipyretics Pyrazolones Drugs 0.000 title abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 39
- 150000002367 halogens Chemical class 0.000 claims abstract description 38
- 150000001875 compounds Chemical class 0.000 claims abstract description 37
- 239000001257 hydrogen Substances 0.000 claims abstract description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 28
- 239000000203 mixture Substances 0.000 claims abstract description 26
- 125000001424 substituent group Chemical group 0.000 claims abstract description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 14
- 239000000460 chlorine Substances 0.000 claims abstract description 13
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 13
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 10
- 125000004433 nitrogen atoms Chemical group N* 0.000 claims abstract description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 5
- 150000003457 sulfones Chemical class 0.000 claims abstract description 5
- 150000003462 sulfoxides Chemical class 0.000 claims abstract description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract 3
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 239000000126 substance Substances 0.000 claims description 26
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 25
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 10
- 125000004434 sulfur atoms Chemical group 0.000 claims description 9
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- UYMQWGLCXYHTES-UHFFFAOYSA-N phenyl(1H-pyrazol-5-yl)methanone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=NN1 UYMQWGLCXYHTES-UHFFFAOYSA-N 0.000 claims description 8
- 150000003254 radicals Chemical class 0.000 claims description 8
- PKGNMKMLAXMKMC-UHFFFAOYSA-N 4-benzylidene-1H-pyrazol-5-one Chemical compound O=C1NN=CC1=CC1=CC=CC=C1 PKGNMKMLAXMKMC-UHFFFAOYSA-N 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 5
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims description 4
- 125000005966 1,2,4-thiadiazolidinyl group Chemical group 0.000 claims description 4
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 claims description 4
- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 claims description 4
- 125000005965 1,3,4-oxadiazolidinyl group Chemical group 0.000 claims description 4
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims description 4
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims description 4
- 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 claims description 4
- OZSWAEYPIVJXRX-UHFFFAOYSA-N 2,3-dihydropyrazolyl Chemical group [N]1C=C=C=N1 OZSWAEYPIVJXRX-UHFFFAOYSA-N 0.000 claims description 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl-oxo-[1-[6-(trifluoromethyl)pyridin-3-yl]ethyl]-$l^{6}-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 claims description 4
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 4
- 125000003965 isoxazolidinyl group Chemical group 0.000 claims description 4
- 125000000160 oxazolidinyl group Chemical group 0.000 claims description 4
- 125000002971 oxazolyl group Chemical group 0.000 claims description 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 4
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 4
- 125000005958 tetrahydrothienyl group Chemical group 0.000 claims description 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
- 125000001984 thiazolidinyl group Chemical group 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 3
- 125000005964 1,2,4-oxadiazolidinyl group Chemical group 0.000 claims description 3
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 3
- JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 claims description 3
- CKWNWXNUBABCQR-UHFFFAOYSA-N 1,5-didehydro-3,4-dihydropyrazol-1-ium-2-ide Chemical group C1CC#[N+][N-]1 CKWNWXNUBABCQR-UHFFFAOYSA-N 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000002632 imidazolidinyl group Chemical group 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 125000002757 morpholinyl group Chemical group 0.000 claims description 3
- 125000004430 oxygen atoms Chemical group O* 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 3
- 125000003072 pyrazolidinyl group Chemical group 0.000 claims description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 claims description 3
- 125000005967 1,3,4-thiadiazolidinyl group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 230000001276 controlling effect Effects 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 2
- ILWJAOPQHOZXAN-UHFFFAOYSA-N 1,3-dithianyl Chemical group [CH]1SCCCS1 ILWJAOPQHOZXAN-UHFFFAOYSA-N 0.000 claims 2
- 238000009472 formulation Methods 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- AINQVGLHEIMYSQ-UHFFFAOYSA-N 4-benzoylpyrazol-3-one Chemical class C=1C=CC=CC=1C(=O)C1=CN=NC1=O AINQVGLHEIMYSQ-UHFFFAOYSA-N 0.000 claims 1
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 claims 1
- 150000001266 acyl halides Chemical class 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000005052 dihydropyrazolyl group Chemical group N1(NCC=C1)* 0.000 claims 1
- 239000011814 protection agent Substances 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 6
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 description 19
- 239000000047 product Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000003921 oil Substances 0.000 description 8
- 238000007792 addition Methods 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000004359 castor oil Substances 0.000 description 6
- 235000019438 castor oil Nutrition 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000012141 concentrate Substances 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 125000001153 fluoro group Chemical group F* 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000005507 spraying Methods 0.000 description 5
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 125000001246 bromo group Chemical group Br* 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N oxane Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical compound CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 3
- JHIVVAPYMSGYDF-UHFFFAOYSA-N Cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 3
- RCJVRSBWZCNNQT-UHFFFAOYSA-N Dichlorine monoxide Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 3
- 240000008042 Zea mays Species 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 230000035784 germination Effects 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 3
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- 244000045561 useful plants Species 0.000 description 3
- KATVVEGJZPKCQH-UHFFFAOYSA-N (5-chloro-1H-pyrazol-4-yl)-phenylmethanone Chemical class N1N=CC(C(=O)C=2C=CC=CC=2)=C1Cl KATVVEGJZPKCQH-UHFFFAOYSA-N 0.000 description 2
- 125000005918 1,2-dimethylbutyl group Chemical group 0.000 description 2
- IGERFAHWSHDDHX-UHFFFAOYSA-N 1,3-dioxanyl Chemical group [CH]1OCCCO1 IGERFAHWSHDDHX-UHFFFAOYSA-N 0.000 description 2
- NGMPUAZITZVRTQ-UHFFFAOYSA-N 1-oxonia-2-aza-4-azanidacyclopentene Chemical group C1[N-]C[O+]=N1 NGMPUAZITZVRTQ-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 2
- SARGWIKJFYWAJV-UHFFFAOYSA-N 4,5-didehydro-2H-1,3-oxazole Chemical group C1[N]C#CO1 SARGWIKJFYWAJV-UHFFFAOYSA-N 0.000 description 2
- CUWCPJPNHVRVLQ-UHFFFAOYSA-N 4,5-didehydro-3H-pyrazole Chemical group C1N=NC#C1 CUWCPJPNHVRVLQ-UHFFFAOYSA-N 0.000 description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- PZZYQPZGQPZBDN-UHFFFAOYSA-N Aluminium silicate Chemical compound O=[Al]O[Si](=O)O[Al]=O PZZYQPZGQPZBDN-UHFFFAOYSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N Benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 241000335053 Beta vulgaris Species 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L Calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- VYCPFWWCEBWVLH-UHFFFAOYSA-N Cn1ncc(C=O)c1O Chemical compound Cn1ncc(C=O)c1O VYCPFWWCEBWVLH-UHFFFAOYSA-N 0.000 description 2
- YYLLIJHXUHJATK-UHFFFAOYSA-N Cyclohexyl acetate Chemical compound CC(=O)OC1CCCCC1 YYLLIJHXUHJATK-UHFFFAOYSA-N 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 240000007842 Glycine max Species 0.000 description 2
- 240000006962 Gossypium hirsutum Species 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N Isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-L Sulphite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N Thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 240000008529 Triticum aestivum Species 0.000 description 2
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Natural products O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 125000003118 aryl group Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- 159000000007 calcium salts Chemical class 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- 238000011097 chromatography purification Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 238000005695 dehalogenation reaction Methods 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 239000003906 humectant Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 125000002346 iodo group Chemical group I* 0.000 description 2
- 125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 description 2
- 229920005610 lignin Polymers 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N n-butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 125000004497 pyrazol-5-yl group Chemical group N1N=CC=C1* 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000002829 reduced Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 description 2
- 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 description 2
- 150000003918 triazines Chemical class 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2R,3R,4S,5R,6S)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2S,3R,4S,5R,6R)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2R,3R,4S,5R,6R)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
- SJSYJHLLBBSLIH-SDNWHVSQSA-N (E)-3-(2-methoxyphenyl)-2-phenylprop-2-enoic acid Chemical compound COC1=CC=CC=C1\C=C(\C(O)=O)C1=CC=CC=C1 SJSYJHLLBBSLIH-SDNWHVSQSA-N 0.000 description 1
- CRPTXKKKIGGDBX-UHFFFAOYSA-N (Z)-but-2-ene Chemical group [CH2]C=CC CRPTXKKKIGGDBX-UHFFFAOYSA-N 0.000 description 1
- GTIIVHODSNYECK-UHFFFAOYSA-N 1,1,1-trifluoropropane Chemical group [CH2]CC(F)(F)F GTIIVHODSNYECK-UHFFFAOYSA-N 0.000 description 1
- 125000001766 1,2,4-oxadiazol-3-yl group Chemical group [H]C1=NC(*)=NO1 0.000 description 1
- 125000001305 1,2,4-triazol-3-yl group Chemical group [H]N1N=C([*])N=C1[H] 0.000 description 1
- GLLHHKSMSYUTEY-UHFFFAOYSA-N 1,3,4,5-tetradehydro-2H-thiophene Chemical group C1C#CC#S1 GLLHHKSMSYUTEY-UHFFFAOYSA-N 0.000 description 1
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 1,5-dihydro-4H-imidazol-4-one Chemical class O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 1
- WCIFVXNIHUSTHF-UHFFFAOYSA-N 1-bromopropane Chemical group [CH2]CCBr WCIFVXNIHUSTHF-UHFFFAOYSA-N 0.000 description 1
- BYLAWYTWAYOBDP-UHFFFAOYSA-N 1-chlorobutane Chemical group [CH2]CCCCl BYLAWYTWAYOBDP-UHFFFAOYSA-N 0.000 description 1
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- 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 description 1
- 125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N n-methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N nicotinic acid Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000005246 nonafluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 229920000847 nonoxynol Polymers 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000000269 nucleophilic Effects 0.000 description 1
- 235000018343 nutrient deficiency Nutrition 0.000 description 1
- 229920002113 octoxynol Polymers 0.000 description 1
- 229940005938 ophthalmologic antiinfectives Sulfonamides Drugs 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002409 penten-3-yl group Chemical group C=CC(CC)* 0.000 description 1
- 125000002262 penten-4-yl group Chemical group C=CCC(C)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229940044654 phenolsulfonic acid Drugs 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 150000008048 phenylpyrazoles Chemical class 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 230000003032 phytopathogenic Effects 0.000 description 1
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
- 239000004476 plant protection product Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
- 150000004892 pyridazines Chemical class 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 1
- 235000013526 red clover Nutrition 0.000 description 1
- 230000001105 regulatory Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005624 silicic acid group Chemical class 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002195 synergetic Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000004523 tetrazol-1-yl group Chemical group N1(N=NN=C1)* 0.000 description 1
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 1
- 229940026752 topical Sulfonamides Drugs 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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Abstract
The invention relates to benzylidene pyrazolones of formula (I), wherein the substituents and index n have the following meanings:R1=optionally substituted C1-C6 alkyl;R2=optionally substituted C1-C6 alkyl, optionally substituted C1-C6 alkoxy, halogen, nitro, cyano;R3=hydrogen, halogen, nitro, cyano, a group NR5R6, OCOR5, NR5COR6,CO2R5, -COSR5, -CONR5R6, C1-C4-alkoxyiminoalkyl, C1-C6 alkoxycarbonyl, optionally substituted C1-C6 alkyl, optionally substituted C1-C6 alkoxy, optionally substituted C1-C6 alkylthio, optionally substituted C2-C6 alkenyl, optionally substituted phenyl, optionally substituted phenoxy, an optionally substituted 5- or 6-membered saturated or unsaturated heterocycle which can contain up to 4 nitrogen atoms and/or up to 2 oxygen or sulphur atoms as ring members;R4=C1-C6 alkyl, C1-C4 halogen alkyl;or R3 and R4=an optionally substituted saturated or unsaturated 2- or 3-membered bridge which can contain one sulphur atom which can be oxidized into sulfoxide or sulfone, R5=hydrogen or optionally substituted C1-C6 alkyl;R7=hydrogen, C1-C6 alkyl or C1-C4 halogenalkyl;n=0, 1 or 2;X=hydrogen, chlorine or bromine. The compounds to which claim is laid are available in both a trans and a cis form or can be a mixture of these isomers.
Description
BENCILIDENPIRAZOLONAS, ITS OBTAINING AND USE.
Description
The present invention relates to benzylidene pyrazolones of formula I
in which the substituents and the index have the following meanings:
R1 Ci-Cβ-alkyl event. sust .; 20 R2 Ci-Cß-alkyl event. sust., Ci-Cg-alkoxy event. Substance, halogen, nitro, cyano;
R3 hydrogen, halogen, nitro, cyano, a group NR5R6, OCO
NR5COR6, C02R5, -COSR5, -CONR5R6, C? -C4-alkoxyiminoalkylC? -C6-alkylcarbonyl, C? -C6-alkyl event. sust., C? ~ C6-alkoxy event. sust., Ci-Cg-alkylthio event. sust C-C6 ~ alkenyl event. sust., C-Cg-alkynyl event. your phenyl event. sust., phenoxy event. sust., a heterocic
e ^ 5 or 6 members, saturated or unsaturated, event. sust
Which may contain up to 4 nitrogen atoms, and / or sulfur atom as ring members;
R4 Ci-Cβ-alkyl, C? -C4-haloalkyl?
O well
R3 'R4 a bridge of 2 or 3 members, saturated or unsaturated, event. sust, which may contain a sulfur atom, which
can be oxidized to sulfoxide or sulfone;
R5 hydrogen C? -C6-alkyl event. sust .;
R6 C? -C6-alkyl event. sust; R7 hydrogen, Ci-Cg-alkyl or C? -C4-haloalkyl;
n 0.1 or 2;
X hydrogen, chlorine or bromine;
whose claimed compounds may be present both
(trans form, as in the cis form or represent a mixture of these isomers) In addition, the invention relates to products containing the compounds of the formula I, as well as to the use of the compounds I and the products that the contain for the control of harmful plants, new benzoylpyrazoles of the formula II,
As well as a process for obtaining compounds I and II.
From the literature, for example from EP-A 282 944 or WO 96/26206, 4-benzoyl-pyrazoles of herbicidal action are known. However, 4-benzoyl-5-chloro-pyrazoles are not disclosed to date. In EP-A 282 944 it is only mentioned in general terms that the reaction of 4-benzoyl-5-hydro pyrazoles with acid halides should result in 4-benzoyl-5-chloro-pyrazoles.
Benzylidene diazolones which have, in part, a herbicidal action are known from US 4,382,948 and JP 61268670. All the structures known up to now have a specific mu substitution model in the lower part of the benzylidenepirazolone: in the position opposite to the bridge of methino, for example, is always a hydrogen atom or halogen atom or a trifluoromethyl or nitro group.
The herbicidal properties of the compounds known to date, as well as their compatibility with the crop plants, are only partly satisfactory. Therefore, the present invention had the task of finding new compounds, especially of herbicidal action, with improved properties
Therefore, the benzylidene pyrazolones according to the invention of the formula I were found, as well as their herbicidal action.
The object of the present invention are also the stereoisomers of the compounds of the formula I. The pure stereoisomers, as well as their mixtures, are thus included.
The compounds of formula I can be present as cis or trans isomers and contain, depending on their model, substitution of one or several centers of chirality, and can also be present as enantiomeric or diastereomeric mixtures. Both isomers are subject of the present invention. , pure enantiomers or diastereomers, as well as their mixtures.
The benzylidene pyrazolones according to the invention of the formula benzoylpyrazoles of the formula II can be prepared in the manner described hereinafter.
The benzylidene diazolones of the formula la (X = hydrogen) can be synthesized by Knoevenagel condensation of pyraz. canvases of the formula III, wherein the radicals Reste R1 and R have the meanings indicated above, and a benzaldehyde the formula IV, in which the radicals R2 to R4 have the meanings indicated above, in analogy to the method described
in the US 4,382,948.
r III IV the and
In addition, the compounds can be obtained, for example p
Reductive dehalogenation from compounds of the formula I, wherein X means bromine.
The benzylidene diazolones ib (x = bromine or chlorine) can be obtained by halogenation of the above-described compounds with bromine or chlorine and subsequent dehalogenation with the presence of a base.
Preferably, the benzylidene pyrazolone Ib can be prepared from ketones of the formula V, which are known or can be prepared analogously to the known compounds (see DE-A 19709118.0 and WO 96/26200), by reaction
with halufros of acid. c Suitable acid halides are, for example, the halur of sufluric acid, carbonic acid and phosphoric acid. Thionyl chloride is preferred for the exchange for chlorine,
phosgene, phosphoric pentachloride, and, especially, phosphoric oxychloride. For the bromine substitution, the phosphoric oxybromide is preferably used.
The reaction can be done in a usual way, with or without d
inert solvent under the reaction conditions. The selectivity of the reaction can be regulated, generally, by the addition of a low nucleophilic base, such as, for example, pyridine and dimethylaminopyridine, dimethylformamide.
The reaction temperature is generally at 0 ° C to 200 ° C, preferably at 50 ° C to 140 ° C.
Ib 10 c In this reaction both isomers can be obtained in the newly formed double bond in the form of a mixture. In this case, the isomers can be separated, if necessary (eg by crystallization, extraction or chromatography). fifteen
A secondary product of this reaction are compounds I which, depending on the model of substitution and the embodiment of the reaction, can be obtained in reduced, com parable or predominant properties. These compounds are in many cases
new and extremely interesting as starting materials for active herbicidal substances (see, for example, EP-A 282 944).
/ * "The parts of organic molecules mentioned for substituents R1 - R7 or as radicals on phenyl or het rings
rociclos are representative collective terms for the individual analysis of each one of the members of the respective group. All the hydrocarbon chains, namely, all the alkyl, halogenalyl, cycloalkyl, alkoxy, haloalkoxy, alkylcarbonyl, alkenyl, alkynyl groups can
be linear or branched. Unless otherwise indicated, the halogenated substituents preferably have one to five identical or different halogen atoms. Halogen if gnifica in each case fluoro, chlorine, bromine or iodine.
In addition, they mean, for example:
C? -C4-alkyl, as well as the alkyl portions of other radicals such as, for example, C? -C4-alkoxy, C? -C4-alkylcarbonyl, C? -C4-alkylthio: methyl, ethyl, n -propyl, 1-methylethyl butyl, 1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl
Ci-Cβ-alkyl, as well as the alkyl portions of other radicals such as, for example, Ci-Cg-alkoxy, C6-alkylcarbonyl, C6-alkynylthio: C4-alkyl, like above, as well as pentyl, 1-methylbutyl, 2-methylbutyl, 3-butyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-di-ethylpropyl, 1-methylpentyl, 2- methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1- ethylbyl, 2-ethylbutyl, 1, 1, 2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-3-methylpropyl;
C? -C4-halogenoalkyl: a C1-C4-alkyl radical, as mentioned above, which is partially or completely substituted by fluoro, chloro, bromo and / or iodo s, namely, eg chloromethyl, dichloromethyl, trichloromethyl , fluoro methyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-diflumethyl, 2,2,2-trifluoroethyl, 2-chloro- 2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl.
2, 2, 2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-br mopropyl, 3- bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2,3,3-pentafluoropropyl, hep tafluoropropyl, 1- (fluoromethyl) -2-fluoroethyl, 1- (chloro methyl) - 2-chloroethyl, 1- (bromomethyl) -2-bromoethyl, 4-fluo robutyl, 4-chlorobutyl, 4-bromobutyl and nonafluorobutyl
C1-C4-halogenoalkoxy: a C1-C4 -alkoxy radical, like the above mentioned, which is partially or completely substituted by fluoro, chloro, bromo and / or iodo, namely, eg fluoromethoxy, difluoromethoxy, trifluoromethoxy , chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloro-15-ethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2, 2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2 - chloro-2, 2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2, 2, 2-ricloroethoxy, pentafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2-bromo
propoxy, 3-bromopropoxy, 2, 2-difluoropropoxy, 2,3-difluoro-ropropoxy, 2,3-dichloropropoxy, 3, 3,3-trifluoropropoxy, 3, 3, 3-ricloropropoxy, 2, 2, 3, 3 3-pentafluoropropoxy, hep tafluoropropoxy, 1- (fluoromethyl) -2-fluoroethoxy, 1- (chloro methyl) -2-chloroethoxy, 1- (bromomethyl) -2-bromoethoxy, 4-fluo
Robutoxy, 4-chlorobutoxy, 4-bromobutoxy and nonafluorobutox
C -C6-alkenyl: ethenyl, prop-1-en-l-yl, prop-2-en-l-yl-1-methylethenyl, buten-1-yl, buten-2-yl, buten-3-yl, 1 -methyl-prop-l-en-l-yl, 2-methyl-prop-l-en-1-yl, 1-methyl
prop-2-en-1-yl, 2-methyl-prop-2-en-l-yl, penten-1-yl, penten-2-yl, penten-3-yl, penten-4-yl, 1 -methyl- but- 1-en-l -yl, 2-methyl-but-1-en-l-yl, 3-methyl-
but-1-en-l-yl, l-methyl-but-2-en-l-yl, 2-methyl-but-2-en-l-yl, 3-methyl-but-2-en-l -yl, 1-methyl-but-3-en-l-yl, 2-methyl-but-3-en-l-yl, 3-methyl-but-3-en-l-yl, 1,1-dimethyl -prop- 2 -en-l-yl, 1,2-dimethyl-prop-1-en-l-yl, 1,2-dimethyl-prop-2-en-l-yl, 1-ethyl-propyl- en-2-yl, l-ethyl-prop-2-en-l-yl, hex-1-en-l-yl, hex-2-en-l-yl, hex-3-en-1-yl, hex-4-en-l-yl, hex-5-en-l-yl, 1-methyl -pent-1-en-l-yl, 2-methyl-pent-1-en-l-yl, 3- methyl-pent-l-en-l-yl, 4-methyl-10 pent-1-en-l-yl, l-methyl-pent-2-en-l-yl, 2-methyl-pent-2-en -l-yl, 3-methyl-pent-2-en-l-yl, 4-methyl-pent-2-en-l-yl, l-methyl-pent-3-en-l-yl, 2-methyl - pent-3-en-l-yl, 3-methyl-pent-3-en-l-yl, 4-methyl-pent-3-en-l-yl, l-methyl-pent-4-en-l -yl, 2-methyl-15 pent-4-en-l-yl, 3-methyl-pent-4-en-l-yl, 4-methyl-pent-4-en-l-yl, 1, l- dimethyl-but-2-en-l-yl, 1,1-dimethyl-but-3-en-l-yl, 1,2-dimethyl-but-l-en-l-yl, 1,2-dimethyl-butyl -2-en-l-yl, l, 2-dimethyl-but-3-en-l-yl, 1,3-dimethyl-but-l-en-l-yl, 1,3-dimet il-but-2-en-l-yl, 1,3-dimethyl-20 but-3-en-l-yl, 2,2-dimethyl-but-3-en-l-yl, 2,3-dimethyl - but-l-en-l-yl, 2,3-dimethyl-but-2-en-l-yl, 2,3-dimethyl-but-3-en-l-yl, 3,3-dimethyl-but -l-en-l-yl, 3,3-dimethyl-but-2-en-l-yl, 1-ethyl-but-l-en-l-yl, 1-ethyl-but-2-en-l -yl, l-ethyl-but-3-en-l-yl, 2-ethyl-25 but-1-en-l-yl, 2-ethyl-but-2-en-l-yl, 2-ethyl- but-3-en-l-yl, 1, 1, 2-trimethyl-prop-2-en-l-yl, l-ethyl-1-methyl-prop-2-en-l-yl, l-ethyl- 2-methyl-prop-1-en-l-yl and l-ethyl-2-methyl-prop-2-en-l-yl;
C2-C6-alkynyl: ethynyl, propylene-1-yl, prop-2-yl-yl, but-1-yl-yl, but-1-in-3-yl, but -l-in-4-yl, but-2-in-l -yl, pent-1-in-l-yl,
pent-l-in-3-yl, pent-l-in-4-yl, pent-l-in-5-yl, pent-2-yn-l-yl, pent-2-yn-4-yl , pent-2-in-5-yl, 3-methyl-but-l-in-3-yl, 3-methyl-but-l-in-4-yl, hex-1-yn-l-yl , hex-l-in-3-yl, hex-l-in-4-yl, hex-l-in-5-yl, hex-l-in-6-yl, hex-2-yn-l-yl , hex-2-in-4-yl, hex-2-yn-5-yl, hex-2-yn-6-yl, hex-3-yn-yl, hex-3-yn-2-yl , 3-methyl-pent-l-in-l-yl, 3-methyl-pent-l-in-3-yl, 3-methyl-pent-l-in-4-yl, 3-methyl pent-l- in-5-yl, 4-methyl-pent-l-in-l-yl, 4-methyl-10 pent-2-yn-4-yl and 4-methyl-pent-2-yn-5-yl;
C3-C6-cycloalkyl: skypropyl, cyclobutyl, cyclopentyl and cyclohexyl;
A 5 or 6 membered heterocycle, saturated or unsaturated, optionally substituted, which may contain up to 4 nitrogen atoms and / or up to 2 oxygen or sulfur atoms as ring members, such as, for example, 2-tetrahydrofuranyl, - tetrahydrofuranyl, 2-tetrahydrothienyl, 3-etrahydro-thienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3- pyrazoin, lidinyl, -pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl,
4- thiazolidinyl, 5-aiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1, 2, 4-oxadiazolidin-3-yl, 1,2,4-oxa-diazolidin-5-yl, 1, 2,4-thiadiazolidin -3-yl, 1, 2, 4-thiadi-zolidin-5-yl, 1, 2, 4-triazolidin-3-yl, 1, 3, 4-oxadiazoli-din-2-yl, 1, 3, 4-thiadiazolidin -2-yl, 1, 3, 4-triazolin-30 din-2-yl, 2,3-dihydrofuran-2-yl, 2,3-dihydrofuran-3-yl 2,3-dihydrofuran-4-yl, 2 , 3-dihydrofuran-5-yl, 2,5-dihi drofuran-2-yl, 2,5-dihydrofuran-3-yl, 2,3-dihydro-
thien-2-yl, 2,3-dihydrothien-3-yl, 2,3-dihydrothien-4-yl 2,3-dihydrothien-5-yl, 2,5-dihydrothien-2-yl, 2.5- dihyd thien-3-yl, 2,3-dihydropyrrol-2-yl, 2,3-dihydropyrrol-3-yl, 2,3-dihydropyrrol-4-yl, 2,3-dihydropyrrol-5-yl 2, 5-dihydropyrrol-2-yl, 2,5-dihydropyrrol-3-yl, 2,3-dihydroisoxazol-3-yl, 2,3-dihydroisoxazol-4-yl, 2,3-dihydroisoxazole -5-yl, 4,5-dihydroisoxazol-3-yl, 4,5-dihydroisoxazol-4-yl, 4,5-dihydroisoxazol-5-yl, 2,5-dihydroisoxazol-3-yl, 2 , 5-dihydroisoxa-10-zol-4-yl, 2,5-dihydroxazol-5-yl, 2,3-dihydroisothia-c-zol-3-yl, 2,3-dihydroisothiazol-4-yl, 2,3-dihydroisothi zol-5-yl, 4,5-dihydroisothiazol-3-yl, 4,5-dih.-idroisothi zol-4-yl, 4,5-dihydroisothiazol-5-yl, 2,5-dihydroisothiol-3-yl, 2,5-dihydroisothiazol-4-yl, 2,5-dihydroisothi
-zol-5-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 4,5-dihydropyrazol-3-yl , 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,5-dihydropyrazol-3-yl, 2,5-dihydropyrazol-4-yl, 2,5-dihydropyrazole -5-yl, 2,3-dihydrooxa- 20-zol-2-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 4,5-dihydrooxazol-2-yl, 4,5-dihydrooxazol-4-yl, 4,5-dihydrooxazol-5-yl ?, 2,5-dihydrooxazol-2-yl, 2,5-dihydrooxazol-4-yl, 2,5-dihydrooxa - zol-5-yl, 2,3-dihydrothiazol-2-yl, 2,3-dihydrothia-25-yl-4-yl, 2,3-dihydrothiazol-5-yl, 4,5-dihydrothiazol-2 ilo, 4, 5-dihydrothiazol-4-yl, 4,5-dihydrothiazol-5-yl, 2,5-dihydrothiazol-2-yl, 2,5-dihydrothiazol-4-yl, 2, 5- dihydrothiazol-5-yl, 2,3-dihydroimidazol-2-yl, 2,3-dihydroimidazol-4-yl, 2,3-dihydroimide-30-yl-5-yl, 4,5-dihydroimidazol-2-yl , 4,5-dihydroimidazol-4-yl, 4,5-dihydroimidazol-5-yl, 2,5-dihydroimidazol-2-yl, 2,5-dihydroimidazole -4 -yl, 2,5-dihydroimide-
zol-5-yl, 2-morpholinyl, 3-morpholinyl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 3-tetrahydropyridazinyl 4-etrahydropyridazinyl, 2-tetrahydropyrimidinyl, 4-t-trahydropyrimidinyl, 5-tetrahydropyrimidinyl, 2-tetra dropiracinyl, 1, 3, 5-tetrahydrotriacin-2-yl, 1,2,4-tet, hydrotriazin-3-yl, 1,3-dihydrooxacin-2-yl, 1,3-di-tian-2-yl, 2 -tetrahydropyranyl, 3-tetrahydropyranyl, 4-tetrahydropyranyl, 2-etrahydrothiopyranyl, 3-tetrahi-thothiopyranyl, 4-tetrahydrothiopyranyl, 1,3-dioxo-10-lane-2-yl, 3, 4, 5, 6-tetrahydropyridin-2-yl , 4H-1, 3-thia-cin-2-yl, 4H-, 1, 1-dioxo-2, 3, 4, 5-tetrahydrothien-2-yl, 1,3-dihydroxacin-2-yl, 2 -furyl, 3-furyl, 2-thienyl, 3 -thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4 -is xazolyl, 5 -isoxazolyl, 3-isothiazolyl, 4-isothiazolyl,
-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl-2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, tet zol-5-yl, tetrazol-1-yl, 4-thiazolyl, -thiazolyl, 2-imidazolyl, 4-imidazolyl, 1, 2, 4-oxadiazol-3-yl, 1, 2, 4-oxadiazo'l-5-yl, 1, 2, 4-diazodiazol-3-yl, 2,4-thia-20-diazol-5-yl, 1, 2, 4-triazol-3-yl, 1, 3, 4-oxadiazol-2-yl 1, 3, 4-thiadiazol-2-yl, 1 , 3,4-triazol-2-yl, 2-pyridinyl 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, , 3, 5- triazin-2-yl, 1, 2, 4-triazin-3-yl,
, 1,2,4, 5- tetracin-3-yl.
With regard to the herbicidal action of the benzylidene diazole I, the following meanings are especially preferred for the substituents, each time alone or in combination
tion:
R1 C? -C "4-alkyl or C? -C4-halogenoalkyl;
R2 C? -C4-alkyl, C? -C4-haloalkyl, C? -C4-alkoxy, C? -C4-haloalkoxy, halogen, nitro, cyano;
R3 hydrogen, halogen, nitro, cyano, NR5R6 group one, OCOR5 N 5COR6, C02R5, -COSR5, -CONR5R6, C? -C4-alcoxiiminoalquil C? -C4-alkylcarbonyl, C? -C4 alkyl optionally Susti tuted by halogen, C? -C4? Alkoxy or phenyl, the phenyl ring being in turn substituted by halogen, C? -C2-alkyl or C? -C-alkoxy, C? -C4-alkoxy optionally substituted by halogen, C? C4-alkoxy or phenyl, the phenyl ring itself being able to be substituted by halogen, C? -C2-alkyl or C? -C2-alkoxy, C? -C4-alkylthio optionally substituted by halogen, C? -C4-alkoxy or phenyl, wherein phenyl ring may in turn be substituted by halogen, C? -C2-alkyl or C? -C2-alkoxy, C? -Cg-alkenyl or C2-C6-alkynyl optionally substituted by C? -C4-alkyl or halogen, phenyl or phenoxy optionally substituted by C? -C4-alkyl, C? -C4-alkoxy, C? -C-haloalkyl, C? -C4-halogenoalkoxy, halogen, phenyl, cyano, alkoxycarbonyl or nitro, a heterocyclic 5 or 6 members, saturated or unsaturated, eventually their substituted by C? -C4-alkyl, C? -C4-alkoxy, C? -C4-haloalkyl, C? -C4-halogen, alkoxy, halogen, phenyl, cyano or nitro, and which can contain up to 4 carbon atoms. nitrogen and / or up to 2 oxygen atoms or sulfur atoms as ring members, seleccionad group: tetrahydrofuranyl, tetrahydrothienyl, dinilo pirro, isoxazolidinyl, isothiazolidinyl, oxazolidinyl pirazolidini, thiazolidinyl, imidazolidinyl, 1,2,4-ox diazolidinyl, 1, 2 , 4-thiadiazolidinyl, 1, 2,4-triazolidinyl, 1,3,4-oxadiazolidinyl, 1,3,4-thiadiazolidinyl.
1, 3, 4-triazolidinyl, 2,3-dihydrofuranyl, 2,5-dihydrofu ranyl, 2,3-dihydrothienyl, 2,5-dihydrothienyl, 2,3-dihydropyrrolyl, 2,5-dihydropyrrolyl, 2,3- dihydroisoxazolyl, 4, 5-dihydroisoxazolyl, 2, 5-dihydroisoxazolyl, 2,5-dihydroxazolyl, 2,3-dihydroisothiazolyl, 4,5-dihydroisothiazolyl, 2, 5-dihydroisothiazolyl, 2, 3 zolilo -dihidropir, 4 , 5-dihydropyrazolyl, 2, 5 -dihidropirazolilo, 2, 3-dihydro-oxazolyl, 4, 5 -dihidrooxazolilo, 2, 5 xazolilo -dihidroo, 2, 3 -dihidrotiazolilo, 4, 5-dihydrothiazolyl 10 2, 5-dihydrothiazolyl, 2 3 -dihidroimidazolilo, 4,5-dihi-c- droimidazolilo, 2, 5 -dihidroimidazolilo, morpholinyl, ridinilo pip, tetrahidropiridacinilo, tetrahydropyrimidinyl tetrahidropiracinilo, 1, 3, 5- etrahidrotriacinilo, 1, 2, 4- tetrahidrotriacinilo, 1, 3 -dihydrooxacinyl, 1,3-di
tianilo, tetrahydropyranyl, tetrahydrothiopyranyl, 1, 3-dioxolanyl, 1, 1-dioxo-2, 3, 4, 5 - tetrahydrothienyl, 1, 3 -dihidrooxacinilo, furyl, thienyl, pyrrolyl, Lilo isoxaz, isothiazolyl, pyrazolyl, oxazolyl, thiazolyl, im-dazolyl, 1,2,4-oxadiazolyl, 1, 2,4-thiadiazolyl, 1, 2, 4-triazolyl, tetrazolyl, 1,3,4-oxadiazolyl, 1,3-, 4-thiadiazolyl, 1, 3,4-triazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, 1,3,5-triazinyl, c. 1,2,4-triazinyl, 1,2,4,5-tetracinyl;
R4 Ci-Cβ-alkyl, C? -C4-haloalkyl;
R3 'R4 means a bridge of 2 or 3 members, saturated or without
Saturate, which may contain a sulfur atom, which is oxidized to sulfoxide or sulfone;
R5 hydrogen, C? -C4-alkyl, which may be unsubstituted substituted by halogen, C? -C4-alkoxy or phenyl, the phenyl ring being capable of carrying from one to five substituents selected from the group: halogen, C? -C2- alkyl or C? -C2-a coxy;
R6 C? -C4 alkyl, which is unsubstituted or substituted by halogen, C? -C4-alkoxy or phenyl, the phenyl ring being able to carry from one to five substituents selected from the group: halogen, C? -C2-alkyl or C C2-alkoxy;
R7 hydrogen, Ci-Q-alkyl or Ci-Cj-haloalkyl;
n 0, 1 or 2;
X hydrogen, chlorine or bromine;
Whose claimed compounds may be present in either the trans form or in the cis form, or as mixtures of these isomers.
Preferred are phenyl rings and heterocycles, which may be unsubstituted or carry one to three halogen atoms and / or one or two radicals selected from the group: nitro, cyan methyl, ethyl, trifluoromethyl, methoxy, ethoxy or trifluorome-toxin.
Especially preferred are the compounds of the formula I in Table 1, in which the substituents have the following meanings, either by themselves or in combination.
R1 methyl, ethyl;
R2 chloro, methyl, methoxy;
R3 hydrogen, methyl, optionally substituted on the phenyl part by fluoro, chloro, methyl or methoxy substituents benzyl, allyl, propin-3-yl, methoxy, ethoxy, 2-methoxyethoxy, methylthio, methylcarbonyl, methoxycarbonyl, dimethyl minocarbonyl, cyano; preferably phenyl event. Substituted by fluoro, chloro, methyl or methoxy, 2-furyl, 3-fluoro, 2-thienyl, 3-thienyl, 4,5-dihydroisoxazol-3-yl, isoxazol-5-yl, isoxaz l-3-yl , pyrazol-1-yl, pyrazol-5-yl, oxazol-2-yl, 4,5-dihydrooxazol-2-yl, 1,3-di xolan-2-yl, 1,3-dithiolan-2- ilo, thiazol-2-yl, thiazol-5-yl, thiazol-4-yl, [1, 2, 4] -triazol-1-yl, [1,4] -oxadiazol-2-yl, 2-pyridyl, 3-pyridyl, 4-pyridyl, pyrimidin-2-yl, pyrimidin-4-yl, 1,3-dioxan-2-yl, 1,3-dithian-2-yl;
R4 methyl;
R7 hydrogen;
n 2;
X chlorine.
The benzoylpyrazoles of the formula II, in which R3 means a 5- or 6-membered heterocycle, saturated or unsaturated, optionally subsituted, are new. As intermediate products for obtaining the active herbicidal substances described in the German patent registration application No.
19740494. 4, the benzoylpyrazoles of the formula II are particularly suitable, in which the substituents have the following types:
R 1 C? -C 4 alkyl or C? -C 4 -haloalkyl;
R2 C? -C4-alkyl, C1-C4-haloalkyl, C? -C4-alkoxy, C1-C4 haloalkoxy, halogen;
R3 a 5- or 6-membered, saturated or unsaturated heterocycle unsubstituted or substituted by C? -C4-alkyl, C? -C4-C? -C4-haloalkyl,? C? -C4-halogenoalkoxy or halogen, or selected of the group: tetrahydrofuranyl, tetrahydrothienyl, pyrrolidinyl, isoxazolidinyl, isothiazolidinyl, pyrazolidinyl, oxazolidinyl, thiazolidinyl, imidazolidyl, 1,2,4-oxadiazolidinyl, 1, 2, 4-thiadiazolidinyl, 1, 2, 4-triazolidinyl, 1, 3,4-oxadiazolidinyl, 1,3,4-thiazodiazolidinyl, 1,3-triazolidinyl, 2,3-dihydrofuranyl, 2,5-dihydrofuranyl, 2,3-dihydrothienyl, 2,5-dihydrothienyl, 2, 3 dihydropyrrolyl, 2,5-dihydropyrrolyl, 2,3-dihydroisoxazolyl, 4,5-dihydroisoxazolyl, 2,5-dihydroisoxazolyl, 2,5-dihydroxazolyl, 2,3-dihydroisothiazolyl, 4,5-dihydroisothiazolyl, 2, 5 -dihydroisothiazolyl, 2,3-dihydropyrazolyl, 4,5-dihydropyrazolyl, 2,5-dihydropyrazolyl, 2,3-dihydrooxazolyl, 4,5-dihydrooxazolyl, 2,5-dihydrooxazolyl, 2,3-dihydrothiazolyl, 4, 5-dihi Drothiazolinyl, 2,5-dihydrothiazolyl, 2,3-dihydroimidazolyl, 4,5-dihydroimidazolyl, 2,5-dihydroimidazolyl, morpholinyl, piperidinyl, tetrahydropyridazinyl, tetrahydropyrimidinyl, tetrahydropyrazinyl, 1, 3, 5-tetrahydrotriacyl nyl, 1,2,4-tetrahydrotriazinyl, 1,3-dihydrooxacinyl, 1,3-dithynyl, tetrahydropyranyl, tetrahydrothiopyranyl 1,3-dioxolanyl, 1, l-dioxo-2, 3,4,5-tetrahydrothienyl, 1,3-dihydrooxacinyl , furyl, thienyl, pyrrolyl, isoxa lyl, isothiazolyl, pyrazolyl, oxazolyl, thiazolyl, dazolyl, 1,2,4-oxadiazolyl, 1,2,4-thiadiazolyl, 1, 2, 4-triazolyl, tetrazolyl, 1,3 , 4-oxadiazolyl, 1,3, 4-thiadiazolyl, 1,3-triazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, 1, 3, 5-triazinyl, 1, 2, 4-triazinyl, 1, 2, 4,5-tetrathinyl, insbesondere bevo zugt sind: 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 10 4, 5-dihydroisoxazol-3-yl, isoxazol-5-yl, isoxazol-3-yl pyrazol-1-yl, pyrazol-5-yl, oxazol-2-yl, 4, 5-dihydro xazol-2-yl, 1,3-dioxolan-2-yl, 1,3-dithiolan-2-yl, thiol-2-yl, thiazol-5-yl, thiazol-4-yl, [1, 2, 4] -triazol-1-yl, [1, 3, 4] -oxadiazol-2-yl, 2-pyridyl, 3-pyridyl-15-diol, 4-pyridyl, pyrimidin-2-yl , pyrimidin-4-yl, 1,3-dioxan-2-yl, 1,3-dithian-2-yl;
R 4 C 4 -C 4 alkyl or C 1 -C 4 -haloalkyl;
R7 hydrogen, C? ~ C4-alkyl or C? -C4-halogenoalkyl;
n 0, 1, 2; C Chlorine, Bromine, 25 Compounds II of Table 2 are especially preferred.
Examples of obtaining:
1) Cis-4- [chloro (2-chloro-3- (4,5-dihydroisoxazol-3-yl) -4-methylsulfonylphenyl) methylene] -2-methyl-2,4-dihydro-pyrazole-3-on (Tab.l No. 1.20):
.0 g of (2-chloro-3- (4,5-dihydroisoxazol-3-yl) -4-methylsu fonylphenyl) (5-hydroxy-l-methyl-lH-pyrazol-4-yl) -methanone 15 ml of toluene are mixed with 2.0 g of phosphoric oxychloride and two drops of dimethylformamide and heated to reflux. Another 1.0 g of phosphoric oxychloride is added and another veu is boiled for 7 h. Then, reaction mixture is introduced into 125 ml of ice water and extracted with methyl tere. -butyl ether. The crude product was purified chromatographically on silica gel with cyclohexane / ethyl acetate / methanol. Yield: 1.3 g of colorless solid (cis isomer). iH-NMR (CDC13): d = 3.27 (s); 3.31 (s); 3.45 (t); 4.57 (t); 7.65 (d); 7.73 (s); 8.15 (d). In addition, the benzoylpyrazole isomer is isolated in the chromatographic purification of the reaction mixture:
(5-chloro-l-methyl-pyrazol-4-yl) - (2-chloro-3- (4,5-dihydro-xazol-3-yl) -4-methylsulfonyl-phenyl) -methanone (Tab.2 No. 11.17): 1 H-NMR (CDC13): d = 3.30 (s); 3.45 (t); 3.93 (s), 4.63 (t); 7.61 (d); 7.75 (s); 8.17 (d).
2) Cis-4- [chloro (2-chloro-3- (4,5-dihydroisoxazol-3-yl) -4-methylsulfonylphenyl) methylene] -2-ethyl-2,4-dihydro-pyrazole-3-on (Tab.l No. 1,119):
The compound can be prepared in analogy to example 1. Colorless solid (cis isomer); i-H-NMR (CDC13): d = 1.28
(t); 3.27 (s) 3.46 (t); 3.72 (q), 4.62 (t); 7.64 (d); 7,
(s); 8.16 (d). In addition, the benzoylpyrazole isomer is isolated in the chromatographic purification of the reaction mixture:
(5-Chloro-1-ethyl-pyrazol-4-yl) - (2-chloro-3- (4,5-dihydroiso xazol-3-yl) -4-methylsulfonyl-phenyl) -methanone (Tab.2 No. 11.56): iH-NMR (CDC13): d = 1.50 (t); 3.28 (s); 3.45 (t); 4.28
(q), 4.63 (t); 7.63 (d); 7.74 (s); 8.18 (d).
) Cis-4- [bromo (2-chloro-3- (4,5-dihydroisoxazol-3-yl) -4-methylsulfonylphenyl) methylene] -2-methyl-2,4-dihydro-pyrazol-3-on ( Tab.l No. 1,466) ::
2.5 g of (2-chloro-3- (4,5-dihydroisoxazol-3-yl) -4-methylsu fonylphenyl) (5-hydroxy-l-methyl-lH-pyrazol-4-yl) -methanone 20 ml of toluene are mixed with 1.87 g of phosphoric oxybromide and two drops of dimethylformamide and boiled for 13 h at reflux. The reaction mixture is then introduced into 50 ° C soda solution and extracted with methyl tere, -butyl ether. The crude product is chromatographically purified in silica gel with cyclohexane / ethyl acetate / methanol. ^ -NMR (CDCI3): d = 3.25 (s); 3.31 (s); 3.43 (m); 4.59 (t); 7.57 (d); 7.63 (s); 8.15 (d).
The benzylidene diazolones of the formula I and the benzoylpyrazes of the formula II indicated in tables 1 and 2 below can be prepared in analogy to the prescriptions indicated in the above synthesis examples.
c
fifteen
twenty
o - s.
Table 1:
n
co
or
t? i
n
to
r.
to
t 00
- \
t
LO O
n
LO t
or r
co co
r >
co
co in
p
co O?
r *
or
r
or OO
co
r
OR
to
or
OR
C
r
s.
Table 2: l
CO
or r,
vo
or,
cp o
cp
The compounds I and their salts useful for agriculture are suitable, both in the form of isomeric mixtures, and also in the form of pure isomers, and as herbicides. The herbicidal products containing I are well suited for combating the growth of unwanted plants in areas not intended for cultivation, especially in high amounts of application. In crops, such as wheat, rice, corn, soybeans and cotton are active against harmful grasses and gammas,
without causing damage worthy of mention in the cultivation plants This effect occurs mainly with low amounts of application.
Depending on the respective application method, you can use
the compounds i or the products containing them in other additional plant crops to eliminate the unwanted plants therein. For example, the following crops come into consideration:
Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var.
C napobrassica, Brassica rapa var. silvestris, Camellia sinensis, Cartha us tinctorius, Carya illinoinensis, Citrus
lemon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum Gossypium vitifolium), Helianthus annuus. Hevea brasiliensis
Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Manihot esculenta, Medicago sativ
Musa spec., Nicotiana tabacum (N. rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec., Pisum sativum, Prunus avium, Prunus persica, Pyrus co munis, Ribes sylestre, Ricinus communis , Saccharum officinarum, Sécale cereale, Solanum tuberosum, So ghum bicolor (S. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum. Vicia faba, Vitis vinifera, Zea mays.
In addition, compounds I can also be used in crops which have been made tolerant to the action of herbicides by culture or genetic engineering methods.
The compounds I or the herbicidal products that they contain can be applied before or after the emergency. When the active substances are less tolerated by the crop plants, then application methods can be used in which the herbicidal products are sprayed with the aid of spraying apparatuses in such a way that they do not fall on the leaves of the plants. sensitive cultivation, without only on the leaves of unwanted plants that grow below the first or on the ground covered with unwanted plants (post-directed, lay-by).
The compounds I or the herbicidal products containing them can be used, for example, in the form of aqueous solutions, powders directly sprayable suspensions, also in the form of suspensions, dispersions or emulsions aqueous, oleic or otherwise, dispersions of oil, pastes, Spray, dusting or granulating agents, by spraying, fogging, spraying, sprinkling or watering. The forms of application depend on the purpose of the use; In any case, they must guarantee the finest possible distribution of the active substances of the invention.
Suitable as inert auxiliaries are mineral oil fractions ranging from medium to high boiling point, such as kerosene or diesel oil, in addition, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, such as paraffin, tetrahydronaphthaline. alkylated naphthalenes or their derivatives, alkylated benzenes or their derivatives, methanol, ethane propanol, butanol, cyclohexanol, cyclohexanone or strongly polar solvents, such as * N-methylpyrrolidone or water.
Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders or large water dispersible sides by the addition of water. For the obtention of emulsions, pastes or oil dispersions the substances can be homogenized as such or dissolved in an oil or solvent, by means of humectants, adherents, dispersants or emulsifiers, in water. However, it is also possible to prepare, from the active substance, a humectant, adhering agent, dispersant or emulsifier and, optionally, a solvent or an oil, concentrates which can be diluted with water.
Suitable surfactants are alkali metal, alkaline earth metal, ammonium salts of aromatic sulphonic acids, eg lignin sulphonic acid, phenolsulfonic acid, talisulfonic acid and dibutylnaphthalenesulfonic acid, as well as fatty acid, alkyl and alkylaryl sulphonates, alkyether, lauryl ether and fatty alcohol, as well as salts of sulphonated hexa, hepta and octadecanols, as well as fatty alcohol ethers, naphthalene condensates, their fonnation and its derivatives with formaldehyde, naphthalene or acid condensates naphthalenesulfonic acids with phenol and fo maldehyde, polyoxyethylenectylphenol ethers, isooctylphenol, octylphenol or nonylphenol ethoxylates, alkylphenol polyglycols ethers, tributylphenyl polyglycol ethers, alkylaryl polyethylene glycols, isotridecyl alcohol, condensates of fatty alcohol-ethylene oxide, ethoxylated castor oil, polyoxyethylene alkyl ethers, polyoxypropylene, po-li acetal glycol ether lauryl alcohol, sor bitol esters, sulphite residual liquors and methylcellulose.
The spraying, spraying and atomizing agents can be obtained by mixing the active substances together with a solid support.
Granules, eg coated granules, impregnates and homogeneous granules can be prepared by bonding the active substances with solid supports. Suitable solid supports are mineral soils, such as silica gel, silicic acids, silicic gins, talc, kaolin, limestone, lime, chalk, bolus, clay loess, dolomite, diatomaceous earth, calcium sulfate and magnesium, magnesium oxide, plastics ground, fertilizers, such as ammonium sulphate, ammonium phosphate, ammonium nitrate ureas and vegetable products, such as stone powders, bark powders of trees, wood and nuts, cellulose powders or other solid supports .
The concentrations of the active substances I in the ready formulations can vary widely. The formulations generally contain from 0.001 to 98% by weight, preferably from 0.01 to 95% by weight of at least one active substance. The active substances are used in a purity of 90 bis 100%, preferably 95% up to 100% (according to NMR spectrum).
The compounds I of the invention can be formulated, for example in the following manner:
parts by weight of compound No. 1.20 are dissolved in a mixture containing 80 parts by weight of alkylated benzene, 10 parts by weight of the addition product 8 to 10 moles of ethylene oxide to 1 mole of N-monoethanol acid lamide oleic acid, 5 parts by weight of the calcium salt of dedecylbenzenesulfonic acid and 5 parts by weight of the addition product of 40 moles of ethylene oxide to 1 mole of castor oil. By pouring the solution into 100 000 parts by weight of water and finely distributing therein, an aqueous dispersion containing 0.02% by weight of the active substance is obtained.
II. 20 parts by weight of compound No. 1119 are dissolved in a mixture consisting of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the addition product of 7 moles of oxide of leno to 1 mole. of isooctylphenol and 10 parts by weight of the addition product of 40 moles of ethylene oxide to mol of castor oil. By pouring the solution into 100 000 parts by weight of water and distributing it finely therein, an aqueous dispersion containing 0.02% by weight of the active substance is obtained.
III. 20 parts by weight of the active substance No. 1466 are dissolved in a mixture consisting of 25 parts in pe cyclohexanone, 65 parts by weight of a mineral oil fraction of the boiling point of 210 to ° C and 10 parts by weight of the addition product of 40 me of ethylene oxide to 1 mole of castor oil. By pouring the solution in 100 000 parts by weight of ag and distributing it finely therein, an aqueous dispersion containing 0.02% by weight of the active substance is obtained.
IV. 20 parts by weight of compound No. 21.20 are intimately mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene sulfonic acid, 17 parts by weight the sodium salt of a lignin sulphonic acid of a sulphite residual salt and 60 parts by weight of silica gel p. and ground in a hammer mill. By distributing the mixture finely in 20,000 parts by weight water, a spray mixture containing 0.1% by weight of the active substance is obtained
V. 3 parts by weight of the active substance No. 1119 are mixed with 97 parts by weight of finely divided kaolin. In this way, a spray agent containing 3% by weight of the active substance is obtained.
SAW. 20 parts by weight of the active substance No. 1466 are intimately mixed with 2 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of fatty alcohol-polyglycol ether, 2 parts by weight of the sodium salt of a condensate of phenol sulfonic acid-urea-formaldehyde and 68 parts by weight of a paraffinic mineral oil. A stable oleic dispersion is obtained.
VII. 1 part by weight of compound No. 1.20 is dissolved in a mixture consisting of 70 parts by weight of cyclohexone, 20 parts by weight of ethoxylated isooctylphenol and 1 part by weight of ethoxylated castor oil. A stable emulsion concentrate is obtained.
VIII. 1 part by weight of compound No. 1119 is dissolved in a mixture consisting of 80 parts by weight of cyclohexone and 20 parts by weight of Wettol ® EM 31 (nonionic emulsifier based on ethoxylated castor oil). A stable emulsion concentrate is obtained.
To broaden the spectrum of action and to achieve synergistic effects, the compounds I can be mixed with numerous representatives of other active herbicide and growth regulator groups and applied in conjunction therewith. Examples of suitable mixing components are 1, 2-thiadiazoles, amides, aminophosphoric acid and its derivatives, aminotriazoles, anuides, xalkanoic acid (het) aryl and their derivatives, benzoic acid and its derivatives, benzothiadiazinones, 2-aroyl. -l, 3-cyclohexandiones, hetaryl-aryl-ketones, benzylisoxazolidinones, derivatives of rae-ta-CF-phenyl, carbamates, quinolinecarboxylic acid and its derivatives, chloroacetanilides, cyclohexane-1,3-dione derivatives, diacines, dichloropropionic acid and its derivatives, dihydrobenzofurans, dihydrofuran-3-ones, dinitroanil nas, dinitrophenols, diphenyl ethers, dipyridyls, halogenated carboxylic acids and their derivatives, ureas, 3-phenyluracil imidazoles, imidazolinones, N-phenyl-3, 4, 5,6-tetrahydrophthalimides, oxadiazoles, oxiranes, phenols, aryloxy- and heteroarylox phenoxypropionates, phenylacetic acid and its derivatives, phenylpropionic acid and its derivatives, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acid Ilic and its derivatives, pirim dil ethers, sulfonamides, sulfonylureas, triazines, triazines, triazolinones, triazolecarboxamides and uracils.
Furthermore, it may be useful to apply the compounds I alone in combination with other herbicides also mixed with other plant protection products, for example products for controlling pests or phytopathogenic fungi or bacteria. It is also interesting the miscibility with solutions of mineral salts, which are used to alleviate nutritional deficiencies or d microelements. Non-phytotoxic oils can also be used
and oil concentrates.
The amounts of application in active substance I amount depending on the respective application end, the time of year, the target plants and their growth state, to 0.00
to 3.0, preferably 0.01 to 1.0 kg / ha of active substance (s.a.).
C Application examples
The herbicidal effect of benzylidene diazolones of formula I can be demonstrated by tests in the greenhouse:
Plastic pots filled with clayey sand with approx. 3.0% humus as sus¬
deal. The seeds of the test plants are seeded according to the species.
In the pre-emergency treatment, actibas substances suspended or emulsified in water are applied directly after sowing by means of fine distribution nozzles. The containers are irrigated slightly to promote germination and growth, and then the pots are covered with bags of water. Clear plastic until the plants have taken root. With this covering a uniform germination of the test plants is reached, as this is not counteracted by the active substances.
For the treatment after the emergence, the test rooms are cultivated until. they have reached a height of growth of 3 to 15 cm, depending on their growth form, then they are treated with active substances suspended or emulsified in water. For this purpose, the test plants are sown directly in the same containers in which they are grown, or they are sown in separated germination containers and the seedlings are planted some days before the treatment in the test vessels. The amount of application in the treatments after emergence amount to 0.125 or 0.0625 kg / ha of s.a.
The plants were maintained according to their species at temperatures of 10 to 25 ° C or 20 to 35 ° C. The trial period amounted to 2 to 4 weeks. During this time the plants were taken care of and their reaction to the different treatments was evaluated.
The evaluation is based on a scale of 0 to 100, where 10 means no emergence or total destruction of at least the parts of the plants surfaced, and means no damage or normal development of growth.
In trials in the greenhouse the following plants are used in treatments after emergence:
The result shows that, with compound No. 1,119, the harmful plants mentioned above (98% of plant damage) can be combed very effectively, while the useful plant, maize, does not suffer any visible damage (0%). Of damage)
The comparative test indicated in Table A shows the improved herbicidal action of compounds 1119 according to the invention, compared to the compound A known from JP-A 61268670 (CA, 106: 209479).
Table A - Tests in the greenhouse with treatments after the emergency
15 20
Claims (6)
- CLAIMS A benzylidene diazolone of the formula I, where the substituents and the index n have the following meanings: X R is C 1 -C 4 alkyl or C 1 -C 4 haloalkyl; R is C1-C4 alkyl, C1-C4 haloalkyl, alkoxy C? -C4, C? -C4 haloalkoxy, halogen, nitro or cyano; 3 R is hydrogen, halogen, nitro, cyano, a group NR5R6, OCOR5, NR5COR6, C02R5, -COSR5, CONR5R6, (C? -C4) alkoxyiminioalkyl, (C? -C4) alkylcarbonyl; the following radicals are unsubstituted or substituted by halogen, C-C4 alkoxy or phenyl, wherein the phenyl ring can carry from 1 to 5 substituents selected from the group consisting of: C1-C2 alkyl and C1-C2 alkoxy; C1-C4 alkyl, C1-C4 alkoxy, C-C4 alkylthio, C2-C6 alkenyl, C2-C6 alkynyl; the following radicals are unsubstituted or substituted by C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, halogen, phenyl, cyano, C 4 -C 4 alkoxycarbonyl or nitro: phenyl, phenoxy, a saturated or unsaturated 5 or 6 membered heterocycle which may contain up to 4 nitrogen atoms and / or up to 2 oxygen or sulfur atoms as ring members; R4 is C? -C? Alkyl or C? -C haloalkyl; or R 3 and R 4 form a saturated or unsaturated, optionally substituted, two or three membered bridge which may contain a sulfur atom, which may be oxidized to obtain sulfoxide or sulfone; R is hydrogen, C? -C alkyl, which is unsubstituted or substituted by halogen, C? -C4 alkoxy or phenyl, where the phenyl ring can carry from 1 to 5 substituents selected from the group consisting of halogen, alkyl of C? -C2 and C? -C2 alkoxy; R is C -C alkyl which is unsubstituted or substituted by halogen, C? -C4 alkoxy or phenyl, where the phenyl ring can carry from 1 to 5 substituents selected from the group consisting of halogen, C? -C2 alkyl and C1-C2 alkoxy; R is hydrogen, C? -Cg alkyl or C? -C4 haloalkyl; n is 0, 1 or 2; X is hydrogen, chlorine or bromine; wherein the claimed compounds may be present in the trans form and in the cis form or as a mixture of these isomers. A benzylidenepyrazolone of formula I, as claimed in claim 1 wherein X is chloro. A benzylidenepyrazolone of the formula I, as claimed in claim 1, in which 7R is hydrogen. A benzylidenepyrazolone of formula I, as claimed in claim 1 wherein 2 R "is C -C4 alkyl, C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy or halogen; a 5- or 6-membered heterocycle, saturated or unsaturated, unsubstituted or substituted by C-C4 alkyl, C? -C4 alkoxy, C? -C4 haloalkyl, C? -C4 haloalkoxy or halogen selected from the group consisting of in: tetrahydrofuranyl, tetrahydrothienyl, pyrrolidinyl, isoxazolidinyl, isothiazolidinyl, pyrazolidinyl, oxazolidinyl, thiazolidinyl, imidazolidinyl, 1,2,4-oxadiazolidinyl, 1, 2, 4-thiadiazolidinyl, 1,2,4-triazolidinyl, 1, 3, 4 oxadiazolidinyl, 1,3,4-thiadiazolidinyl, 1,3-triazolidinyl, 2,3-dihydrofuranyl, 2,5-dihydrofuranyl, 2,3-dihydrothienyl, 2,5-dihydrothienyl, 2,3-10-dihydropyrrolyl, , 5-dihydropyrrolyl, 2,3-dihydroisoxazolyl, 4,5-dihydroisoxazolyl, 2,5-dihydroisoxazolyl, 2,5-dihydroxazolyl, 2,3-dihydroisothiazolyl, 4,5-dihydroisothiaz olyl, 2,5-dihydroisothiazolyl, 2,3-dihydropyrazolyl, 4,5-15 dihydropyrazolyl, 2,5-dihydropyrazolyl, 2,3-dihydrooxazolyl, 4,5-dihydrooxazolyl, 2,5-dihydrooxazolyl, 2,3-dihydrothiazolyl 4,5-dihydrothiazolyl, 2,5-dihydrothiazolyl, 2,3-dihydroimidazolyl, 4,5-dihydroimidazolyl, 2,5-20-dihydroimidazolyl, morpholinyl, piperidinyl, tetrahydropyridazinyl, tetrahydropyrimidinyl, tetrahydropyrazinyl, 1,3,5-tetrahydrotriazinyl, 1, 2, 4-tetrahydrotriazinyl, 1,3-dihydrooxazinyl, 1,3-dithianyl, tetrahydropyranyl, Tetrahydrothiopyranyl, 1,3-dioxolanyl, 1,1-dioxo-2,3, 5-tetrahydrothienyl, 1,3-dihydrooxazinyl, furyl, thienyl, pyrrolyl, isoxazolyl, isothiazolyl, pyrazolyl, oxazolyl, thiazolyl, imidazolyl, 1, 2,4-oxadiazolyl, 1,2,4-thiadiazolyl, 1,2-triazolyl, tetrazolyl, 1,3,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,3-triazolyl, pyridyl, pyridazinyl , pyrimidinyl, pyrazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,4,5-tetrazinyl; R 'is C? -C4 alkyl; R is hydrogen or C?-C 4 alkyl which is unsubstituted or substituted by halogen or C?-C 4 alkoxy; R is C 1 -C 4 alkyl which is unsubstituted or substituted by halogen or C 1 -C 4 alkoxy; R is hydrogen; n is 2; X is hydrogen or chlorine. A composition containing an herbicidally effective amount of at least one benzylidenepyrazolone of the formula I, as mentioned in claim 1, and auxiliaries commonly used in the formulation of crop protection agents. A process for preparing active compositions as herbicides as mentioned in claim 5, which consists of mixing an herbicidally effective amount of at least one benzylidene pyrazolone I, as mentioned in claim 1, and the auxiliaries commonly used in the formulation of agents for crop protection. A method for controlling unwanted vegetation, which consists of allowing an herbicidally effective amount of at least one benzylidene pyrazolone I, as mentioned in claim 1, to act on plants, their habitat and / or on the seeds. A benzoylpyrazole of the formula II: wherein the substituents have the following meanings: R is C 1 -C 4 alkyl or C 1 -C 4 haloalkyl; R is C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C alkoxy, C 1 -C haloalkoxy or halogen; R ° is a 5- or 6-membered, saturated or unsaturated heterocycle, unsubstituted or substituted by C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkyl, C 4 -C haloalkoxy or halogen selected from the group it consists of: tetrahydrofuranyl, tetrahydrothienyl, pyrrolidinyl, isoxazolidinyl, isothiazolidinyl, pyrazolidinyl, oxazolidinyl, thiazolidinyl, imidazolidinyl, 1,2,4-oxadiazolidinyl, 1, 2,4-thiadiazolidinyl, 1,2,4-triazolidinyl, 1, 3, 4 -oxadiazolidinyl, 1,3,4-10-thiadiazolidinyl, 1,3-triazolidinyl, 2,3-dihydrofuranyl, 2,5-dihydrofuranyl, 2,3-dihydrothienyl, 2,5-dihydrothienyl, 2,3-dihydropyrrolyl, 2,5-dihydropyrrolyl, 2,3-dihydroisoxazolyl, 4,5-dihydroisoxazolyl, 2,5-dihydroisoxazolyl, 2,5-dihydroxazolyl, 2,3-dihydroisothiazolyl, 4,5-dihydroisothiazolyl, 2,5-dihydroisothiazolyl, 2 , 3-dihydropyrazolyl, 4,5-dihydropyrazolyl, 2,5-dihydropyrazolyl, 2,3-dihydrooxazolyl, 4,5-dihydrooxazolyl, 2,5-20-dihydrooxazolyl, 2,3-dihydrothi azolyl, 4,5-dihydrothiazolyl, 2,5-dihydrothiazolyl, 2,3-dihydroimidazolyl, 4,5-dihydroimidazolyl, 2,5-dihydroimidazolyl, orpholinyl, piperidinyl, tetrahydropyridazinyl, tetrahydropyrimidinyl, 25-tetrahydropyrazinyl, 1, 3, 5-tetrahydrotriazinyl, 1, 2,4-tetrahydrotriazinyl, 1,3-dihydrooxazinyl, 1,3-dithianyl, tetrahydropyranyl, tetrahydrothiopyranyl, 1,3-dioxolanyl, 1,1-dioxo- 2,3 , 4,5-tetrahydrothienyl, 1,3-dihydrooxazinyl, furyl, thienyl, pyrrolyl, isoxazolyl, isothiazolyl, pyrazolyl, oxazolyl, thiazolyl, imidazolyl, 1,2,4-oxadiazolyl, 1,2,4-thiadiazolyl, 1,2 , 4-triazolyl, tetrazolyl, 1,3,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,3-triazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, 1,3,5-triazinyl, 1,2 , 4-triazinyl, 1,2,4,5-tetrazinyl; 4 R is C -C alkyl or C 1 -C 4 haloalkyl; 7 R is hydrogen, C1-C4 alkyl or haloalkyl of C? C4; n is 0, 1, 2; X 'is chlorine or bromine. A process for preparing benzylidenepyrazones of the formula I as mentioned in claim 1 and benzoylpyrazoles of the formula II, as mentioned in claim 8, which comprises reacting the benzoylpyrazolones of the formula V, wherein the substituents are as defined in claim 1 or claim 8 with acyl halides. SUMMARY OF THE INVENTION. Benzylidene diazolones of the formula I 15 in which the substituents and the index have the following meanings: R1 C? -C6-alkyl event. sust R2 C? -C6 ~ alkyl event. sust., C? -C6-alkoxy event. Substance, halogen, nitro, cyano; R3 hydrogen, halogen, nitro, cyano, a group NR5R6, OCOR NR5COR6, C02R5, -COSR5, -CONR5R6, C? -C4-alkoxyiminoalqui 25 Cx-Cg-alkylcarbonyl, C? -C6-alkyl event. sust., Cx-Cg-alkoxy event. sust., C? -C6-alkylthio event. sust., C2-C6-alkenyl event. .sub.
- 2, C2-C6-alkynyl event. your phenyl event. sust., phenoxy event. sust., a heterocyclic of 5 or 6 members, saturated or unsaturated, event. sust Which may contain up to 4 nitrogen atoms, and / or sulfur atom as ring members; R4 C? -Cg-alkyl, C? -C4-halogenoalkyl; O well R3 'R4 a bridge of 2 or 3 members, saturated or unsaturated, event. sust, which may contain a sulfur atom, which can be oxidized in sulphoxide or sulfone; 5 hydrogen C? -Cg-alkyl event. sust .; R6 C? -Cg-alkyl event. sust .; R7 hydrogen, C? -Cg-alkyl or C? -C4-halogenoalkyl; n 0.1 or 2; X hydrogen, chlorine or bromine; Whose claimed compounds may be present in either the trans form, or in the cis form, or represent a mixture of these isomers.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19751722.6 | 1997-11-21 |
Publications (1)
Publication Number | Publication Date |
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MXPA00004809A true MXPA00004809A (en) | 2001-07-03 |
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