EP2480071A1 - Pesticide preparations containing derivatives of pyrrolidone-4-carboxylic acid - Google Patents
Pesticide preparations containing derivatives of pyrrolidone-4-carboxylic acidInfo
- Publication number
- EP2480071A1 EP2480071A1 EP10755112A EP10755112A EP2480071A1 EP 2480071 A1 EP2480071 A1 EP 2480071A1 EP 10755112 A EP10755112 A EP 10755112A EP 10755112 A EP10755112 A EP 10755112A EP 2480071 A1 EP2480071 A1 EP 2480071A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- substituted
- pyrrolidone
- carboxylic acid
- acid derivatives
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 71
- 239000000575 pesticide Substances 0.000 title claims abstract description 65
- GZVHQYZRBCSHAI-UHFFFAOYSA-N 5-oxopyrrolidine-3-carboxylic acid Chemical class OC(=O)C1CNC(=O)C1 GZVHQYZRBCSHAI-UHFFFAOYSA-N 0.000 title description 10
- -1 N-substituted 2-pyrrolidone-4-carboxylic acid Chemical class 0.000 claims abstract description 66
- 241000196324 Embryophyta Species 0.000 claims abstract description 30
- 239000002671 adjuvant Substances 0.000 claims abstract description 17
- 239000003995 emulsifying agent Substances 0.000 claims abstract description 12
- 239000002270 dispersing agent Substances 0.000 claims abstract description 8
- 239000000080 wetting agent Substances 0.000 claims abstract description 8
- 241000238631 Hexapoda Species 0.000 claims abstract description 5
- 206010061217 Infestation Diseases 0.000 claims abstract description 5
- 208000031888 Mycoses Diseases 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- 150000003863 ammonium salts Chemical class 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 9
- 125000003107 substituted aryl group Chemical group 0.000 claims description 9
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 239000003513 alkali Chemical group 0.000 claims description 4
- 150000001342 alkaline earth metals Chemical group 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000005504 styryl group Chemical group 0.000 claims description 4
- 239000000203 mixture Substances 0.000 description 52
- 239000004009 herbicide Substances 0.000 description 49
- 238000009472 formulation Methods 0.000 description 33
- 239000002917 insecticide Substances 0.000 description 31
- 239000000417 fungicide Substances 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 239000002253 acid Substances 0.000 description 16
- 239000000126 substance Substances 0.000 description 16
- 239000003905 agrochemical Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 239000007921 spray Substances 0.000 description 13
- 150000003839 salts Chemical class 0.000 description 12
- 239000005562 Glyphosate Substances 0.000 description 11
- 150000002148 esters Chemical class 0.000 description 11
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 11
- 229940097068 glyphosate Drugs 0.000 description 11
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 229940125904 compound 1 Drugs 0.000 description 9
- 239000003090 pesticide formulation Substances 0.000 description 9
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 8
- 239000004495 emulsifiable concentrate Substances 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000000839 emulsion Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 230000000361 pesticidal effect Effects 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 150000001408 amides Chemical class 0.000 description 6
- 239000002689 soil Substances 0.000 description 6
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 5
- 231100000674 Phytotoxicity Toxicity 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 229940125782 compound 2 Drugs 0.000 description 5
- 150000002431 hydrogen Chemical group 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 5
- 239000002728 pyrethroid Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- ZEKANFGSDXODPD-UHFFFAOYSA-N glyphosate-isopropylammonium Chemical class CC(C)N.OC(=O)CNCP(O)(O)=O ZEKANFGSDXODPD-UHFFFAOYSA-N 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 239000004530 micro-emulsion Substances 0.000 description 4
- 239000000546 pharmaceutical excipient Substances 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000004576 sand Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000004546 suspension concentrate Substances 0.000 description 4
- OLRBXRSNJFXWTD-KTKRTIGZSA-N 1-[(z)-octadec-9-enyl]-5-oxopyrrolidine-3-carboxylic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCN1CC(C(O)=O)CC1=O OLRBXRSNJFXWTD-KTKRTIGZSA-N 0.000 description 3
- 235000007320 Avena fatua Nutrition 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 239000005946 Cypermethrin Substances 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 241000227653 Lycopersicon Species 0.000 description 3
- 239000005949 Malathion Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229940100389 Sulfonylurea Drugs 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
- 230000004071 biological effect Effects 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 229940125898 compound 5 Drugs 0.000 description 3
- KAATUXNTWXVJKI-UHFFFAOYSA-N cypermethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-UHFFFAOYSA-N 0.000 description 3
- 229960005424 cypermethrin Drugs 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- JXSJBGJIGXNWCI-UHFFFAOYSA-N diethyl 2-[(dimethoxyphosphorothioyl)thio]succinate Chemical compound CCOC(=O)CC(SP(=S)(OC)OC)C(=O)OCC JXSJBGJIGXNWCI-UHFFFAOYSA-N 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 230000002363 herbicidal effect Effects 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 229960000453 malathion Drugs 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000011837 pasties Nutrition 0.000 description 3
- 230000035515 penetration Effects 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 239000003755 preservative agent Substances 0.000 description 3
- 239000013558 reference substance Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000002562 thickening agent Substances 0.000 description 3
- 230000002110 toxicologic effect Effects 0.000 description 3
- 231100000027 toxicology Toxicity 0.000 description 3
- 150000003852 triazoles Chemical class 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 2
- XKLPBDMZJSWRBL-UHFFFAOYSA-N 3-benzoylcyclohexane-1,2-dione Chemical compound C=1C=CC=CC=1C(=O)C1CCCC(=O)C1=O XKLPBDMZJSWRBL-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 241000209764 Avena fatua Species 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229920005682 EO-PO block copolymer Polymers 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- WLLGXSLBOPFWQV-UHFFFAOYSA-N MGK 264 Chemical compound C1=CC2CC1C1C2C(=O)N(CC(CC)CCCC)C1=O WLLGXSLBOPFWQV-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 229930182692 Strobilurin Natural products 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 150000003931 anilides Chemical class 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 239000007884 disintegrant Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000012990 dithiocarbamate Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003623 enhancer Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-O isopropylaminium Chemical compound CC(C)[NH3+] JJWLVOIRVHMVIS-UHFFFAOYSA-O 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- NMJORVOYSJLJGU-UHFFFAOYSA-N methane clathrate Chemical compound C.C.C.C.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O NMJORVOYSJLJGU-UHFFFAOYSA-N 0.000 description 2
- 230000017074 necrotic cell death Effects 0.000 description 2
- DSOOGBGKEWZRIH-UHFFFAOYSA-N nereistoxin Chemical compound CN(C)C1CSSC1 DSOOGBGKEWZRIH-UHFFFAOYSA-N 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000003986 organophosphate insecticide Substances 0.000 description 2
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 2
- 229930195732 phytohormone Natural products 0.000 description 2
- 231100000208 phytotoxic Toxicity 0.000 description 2
- 230000000885 phytotoxic effect Effects 0.000 description 2
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
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- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 2
- YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical compound BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 description 2
- IPLYEZKKADASMG-UHFFFAOYSA-N trioctan-3-yl phosphate Chemical compound CCCCCC(CC)OP(=O)(OC(CC)CCCCC)OC(CC)CCCCC IPLYEZKKADASMG-UHFFFAOYSA-N 0.000 description 2
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- WSWCOQWTEOXDQX-MQQKCMAXSA-M (E,E)-sorbate Chemical compound C\C=C\C=C\C([O-])=O WSWCOQWTEOXDQX-MQQKCMAXSA-M 0.000 description 1
- QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 description 1
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 1
- IDCPFAYURAQKDZ-UHFFFAOYSA-N 1-nitroguanidine Chemical compound NC(=N)N[N+]([O-])=O IDCPFAYURAQKDZ-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 description 1
- QMNWYGTWTXOQTP-UHFFFAOYSA-N 1h-triazin-6-one Chemical compound O=C1C=CN=NN1 QMNWYGTWTXOQTP-UHFFFAOYSA-N 0.000 description 1
- UFBJCMHMOXMLKC-UHFFFAOYSA-N 2,4-dinitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O UFBJCMHMOXMLKC-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
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- BYCRWNBZOPQYJR-UHFFFAOYSA-N octan-3-yl(octan-3-yloxy)phosphinic acid Chemical compound CCCCCC(CC)OP(O)(=O)C(CC)CCCCC BYCRWNBZOPQYJR-UHFFFAOYSA-N 0.000 description 1
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- ZVTQYRVARPYRRE-UHFFFAOYSA-N oxadiazol-4-one Chemical compound O=C1CON=N1 ZVTQYRVARPYRRE-UHFFFAOYSA-N 0.000 description 1
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- YBVNFKZSMZGRAD-UHFFFAOYSA-N pentamidine isethionate Chemical compound OCCS(O)(=O)=O.OCCS(O)(=O)=O.C1=CC(C(=N)N)=CC=C1OCCCCCOC1=CC=C(C(N)=N)C=C1 YBVNFKZSMZGRAD-UHFFFAOYSA-N 0.000 description 1
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- SCWKRWCUMCMVPW-UHFFFAOYSA-N phenyl n-methylcarbamate Chemical compound CNC(=O)OC1=CC=CC=C1 SCWKRWCUMCMVPW-UHFFFAOYSA-N 0.000 description 1
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- 239000011591 potassium Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 150000003139 primary aliphatic amines Chemical class 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
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- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 229940075554 sorbate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 229930185156 spinosyn Natural products 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 1
- FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical compound OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
Definitions
- the present invention relates to pesticide preparations which
- Pesticides are commonly used in the form of a preparation to achieve better utilization of the active ingredient. Such preparations are also referred to as formulations and are generally present in solid or in liquid form. The formulations contain at least one but mostly several excipients that take on a variety of functions.
- auxiliaries examples include solvents, emulsifiers, and others.
- Humectants are understood to mean auxiliaries which increase the biological effectiveness of the active ingredient without itself having a biological effect, for example by improving wetting, retention or uptake into the plant or the target organism.
- formulation types are aqueous
- SL suspension concentrates
- SE suspo-emulsions
- EC emulsifiable concentrates
- OD oil dispersions
- EW emulsions in water
- ME microemulsions
- formulation types are water-soluble powders or granules (SP, SG) or water-dispersible powders or granules (WP, WDP, WG, WDG).
- SP, SG water-soluble powders or granules
- WP, WDP, WG, WDG water-dispersible powders or granules
- Many effective adjuvants used in pesticide preparations are of concern from a toxicological or ecotoxicological point of view, such as
- Nonylphenol ethoxylates due to their endocrine effect, fatty amine ethoxylates (ecotoxic properties) or N-methylpyrrolidone (reprotoxic)
- Pesticidal preparations are those that have no harmful effect on the crop (phytotoxicity). This is especially important for fungicides, insecticides and selective herbicides, but also for non-selective ones
- 2-pyrrolidone-4-carboxylic acids and their salts, esters and amides are useful as active adjuvants for pesticide preparations.
- the present invention therefore relates to pesticide preparations containing
- N-substituted 2-pyrrolidone-4-carboxylic acid derivatives include both the N-substituted 2-pyrrolidone-4-carboxylic acids and also other derivatives, in particular the salts, esters and amides of the N-substituted 2 Pyrrolidone-4-carboxylic acids understood.
- No. 3,224,975 describes lubricant compositions comprising N-alkyl-4-carboxy-2-pyrrolidone in which the alkyl radical comprises 8-25 C atoms.
- GB 1323061 discloses certain N-substituted-4-carboxy-2-pyrrolidones and their use in functional fluids such as
- EP 2 022 781 describes dimeric N-alkyl-4-carboxy-2-pyrrolidone derivatives which are linked via a bridge to the carboxy group and their use as gas hydrate inhibitors.
- EP 2 028 247 describes the use of N-alkyl-2-pyrrolidone-4-carboxylic acid esters as gas hydrate inhibitors.
- WO 2009/086872 and WO 2009/086873 describe the use of N-alkyl-2-pyrrolidone-4-carboxylic acid ammonium salts as corrosion inhibitors.
- pesticides are herbicides, fungicides, insecticides, acaricides, bactericides, molluscides, nematicides and
- physiological reactions such as growth, stinging rhythm, cell division and
- Pesticidal preparations according to the invention are preferably selected from the group consisting of herbicides, insecticides and fungicides.
- Preferred fungicides are aliphatic nitrogen fungicides, amide fungicides such as acylamino acid fungicides or anilide fungicides or benzamide fungicides or strobilurin fungicides, aromatic fungicides, benzimidazole fungicides,
- Benzothiazole fungicides carbamate fungicides, conazole fungicides such as imidazoles or triazoles, dicarboximide fungicides, dithiocarbamate fungicides, imidazole fungicides, morpholide fungicides, oxazole fungicides, pyrazole fungicides, pyridine fungicides,
- Pyrimidine fungicides Pyrole fungicides, quinone fungicides.
- Preferred herbicides are amide herbicides, anilide herbicides, aromatic
- Acid herbicides such as benzoic acid herbicides or picolinic acid herbicides,
- Benzoylcyclohexanedione herbicides benzofuranyl alkyl sulfonate herbicides,
- Cyclohexenoxime herbicides cyclopropylisoxazole herbicides, dicarboximide herbicides, dinitroaniline herbicides, dinitrophenol herbicides, diphenyl ether herbicides,
- Dithiocarbamate herbicides imidazolinone herbicides, nitrile herbicides,
- Organophosphorus herbicides oxadiazolone herbicides, oxazole herbicides,
- Phenoxy herbicides such as phenoxyacetic acid herbicides or
- Phenoxybutanoic acid herbicides or phenoxypropionic acid herbicides Phenoxybutanoic acid herbicides or phenoxypropionic acid herbicides
- Benzoylpyrazole herbicides or phenylpyrazole herbicides pyridazinone herbicides, pyridine herbicides, thiocarbamate herbicides, triazine herbicides, triazinone herbicides, Triazole herbicides, triazolone herbicides, triazolopyrimidine herbicides, uracil herbicides, urea herbicides such as phenylurea herbicides or sulfonylurea herbicides.
- Preferred insecticides are carbamate insecticides, such as
- Lactone insecticides such as avermectin insecticides or milbemycin insecticides or spinosyn insecticides, nereistoxin analogous insecticides, nicotinoid insecticides such as nitroguanidine nicotinoid insecticides or pyridylmethylamino nicotinoid insecticides, organophosphorus insecticides such as organophosphate insecticides or
- Organothiophosphate insecticides or phosphonate insecticides Organothiophosphate insecticides or phosphonate insecticides
- Phosphoramidothioate insecticides oxadiazine insecticides, pyrazoline insecticides, pyrethroid insecticides such as pyrethroid ester insecticides or pyrethroid ether insecticides or pyrethroid oxime insecticides, tetramic acid insecticides,
- Tetrahydrofurandione insecticides Tetrahydrofurandione insecticides, thiazoline insecticides.
- the one or more pesticides of component a) of the pesticide preparations according to the invention are particularly preferably selected from the group consisting of aryloxyphenoxypropionic acid herbicides,
- Benzoylcyclohexanedione herbicides triazolopyrimidine herbicides, strobilurin fungicides, triazole fungicides, nicotinoid insecticides and pyrethroid insecticides.
- the one or more pesticides of component a) of the pesticide formulations according to the invention are selected from the group consisting of malathion, cypermethrin, glyphosate in the acid form and glyphosate in the form of salts.
- preferred are glyphosate in the acid form and in the form of salts.
- salts of glyphosate glyphosate isopropylammonium is preferred.
- the biological activity of a pesticide can be determined by the plant growth or the damage to the plants by the action of the active ingredient on the leaf as a function of the time of action and the active ingredient concentration.
- the one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives of component b) of the pesticidal preparations according to the invention are preferably the N-substituted, preferably N-alkyl or N-alkenyl-substituted, 2 Pyrrolidone-4-carboxylic acids and their salts, esters and amides.
- R1 Cs to C 30 alkyl or C 8 - to C ß o-alkenyl
- Y is OM, -O- [AO] n is -X or NR2R3,
- M is hydrogen, alkali or alkaline earth metal, ammonium NH 4 + or substituted ammonium, wherein the substituted ammonium is preferably selected from mono-, di- and trisubstituted
- Ammonium are in turn selected from alkyl groups having 1 to 4 carbon atoms and CH 2 CH 2 OH,
- n is a number from 0 to 100
- X is C to C 2 o-alkyl, benzyl or a substituted aryl radical, wherein the substituted aryl radical is preferably selected from phenyl, the is substituted with 1 to 3 substituents, and these substituents are in turn selected from alkyl groups having 1 to 4 carbon atoms and styryl and in the event that n is not 0, X can also be hydrogen,
- R 2 and R 3 independently of one another are hydrogen, C 1 - to C 2 o-alkyl or
- p is a number from 1 to 20.
- the one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives of component b) of the pesticidal formulations according to the invention are selected from the compounds of the formula (1)
- the one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives of component b) of the pesticide formulations according to the invention are selected from the compounds of the formula (2)
- C 8 is - to C 30 -alkyl or C 30 - to C 30 -alkenyl
- C is C 2 to C 20 alkyl, benzyl or a substituted aryl radical, wherein the substituted aryl radical is preferably selected from phenyl substituted with 1 to 3 substituents, and these substituents are in turn selected from alkyl groups having 1 to 4 carbon atoms and styryl and in the If n is not 0, then X can also be hydrogen.
- the one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives of component b) of the pesticide formulations according to the invention are selected from the compounds of the formula (3)
- R 1 is C 8 - to C 30 -alkyl or C 8 - to C 30 -alkenyl
- R2 and R3 are independently hydrogen, C to C 2 o-alkyl or
- p is a number from 1 to 20.
- R1 is preferably a linear or branched alkyl or alkenyl group having 8 to 24 carbon atoms
- R1 particularly preferably represents a linear or branched octyl radical, a cocoyl radical or an oleyl radical.
- M is preferably hydrogen, Na, K, Ca,
- A is preferably ethylene or propylene and particularly preferably ethylene.
- X is preferably hydrogen (when n is not zero), C 4 -C 4 -alkyl and particularly preferably methyl, n is preferably from 1 to 40 and particularly preferably from 5 to 25. If X in the formulas (Z) and ( 2) represents a substituted aryl radical, this is preferably 2,4,6-tri-secondary-butylphenyl or 2,4,6-tristyrylphenyl.
- R 2 and R 3 are preferably hydrogen
- R2 and R3 is methyl or -CH 2 -CH 2 -OH.
- 2-pyrrolidone-4-carboxylic acid derivatives of component b) to vary and thus adapt the physical and physico-chemical properties of the molecules, the N-substituted 2-pyrrolidone-4-carboxylic acid derivatives in the inventive preparations can perform a variety of tasks ,
- N-substituted 2-pyrrolidone-4-carboxylic acid derivatives of component b) of the pesticide preparations according to the invention and in particular the compounds of the formulas (Z) and (1) to (3) are preferably suitable as adjuvants,
- Emulsifiers, dispersants or wetting agents Another object of the present invention is therefore the use of one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives and preferably one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives selected from the formulas (Z) and ( 1) to (3) as adjuvant,
- the present invention also provides the use of one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives and preferably one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives selected from the formulas (Z) and ( 1) to (3) as an emulsifier, preferably in a pesticide preparation according to the invention.
- Particularly preferred emulsifiers are compounds of the formula (1) in which M is not hydrogen (anionic emulsifiers) or compounds of the formula (2) in which n is 5 (nonionic emulsifiers).
- Compounds of formula (2) wherein X is other than hydrogen and n is 5 are particularly preferred as emulsifiers for pesticide formulations containing an active ingredient which is sensitive to water or to OH groups, such as sulfonylureas (SUs).
- SUs sulfonylureas
- the present invention also provides the use of one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives and preferably one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives selected from the formulas (Z) and ( 1) to (3) as a wetting agent, preferably in a pesticide preparation according to the invention.
- Another object of the present invention is the use of one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives and preferably one or more N-substituted 2-pyrrolidone-4-carboxylic acid Derivatives selected from the formulas (Z) and (1) to (3) as a dispersant, preferably in a pesticide preparation according to the invention.
- SC Suspension concentrates
- SE suspo-emulsions
- EC Concentrates
- OD oil dispersions
- EW emulsions in water
- ME microemulsions
- n ⁇ 9 or compounds of the formula (3) have a low solubility in water and are therefore particularly preferably used as auxiliaries for solvent- or oil-containing preparations such as ECs, EWs, SEs, MEs and ODs.
- solvent- or oil-containing preparations such as ECs, EWs, SEs, MEs and ODs.
- Formulation types selected from water-soluble powders or granules (SP, SG) or water-dispersible powders or granules before (WP, WDP, WG, WDG).
- Compounds of the formulas (Z) and (1) to (3) which are distinguished by a melting point of preferably> 30 ° C. and particularly preferably> 40 ° C., are particularly preferably suitable for use in solid preparations.
- the present invention also provides the use of one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives and preferably one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives selected from the formulas (Z) and ( 1) to (3) for the preparation of pesticide preparations according to the invention.
- the preparation of the pesticide formulations according to the invention is possible in various ways and is well known to the person skilled in the art.
- N-substituted 2-pyrrolidone-4-carboxylic acids of component b) of the pesticide formulations according to the invention are obtained by reacting
- Itaconic acid with primary amines can be prepared as described in EP 0 069 512, US 3,224,975 and US 4,127,493.
- N-substituted 2-pyrrolidone-4-carboxylic acids with a base possible.
- Suitable bases are preferably NaOH, Ca (OH) 2 , CaC0 3 , KOH and amines such as
- Ammonia iso-propylamine, mono-, di- or triethanolamine.
- the preparation of the corresponding esters can, for example, by addition of alkylene oxides to the N-substituted 2-pyrrolidone-4-carboxylic acids or by condensation of N-substituted 2-pyrrolidone-4-carboxylic acids with
- polyglycol ethers optionally substituted polyglycol ethers. It may, for example, by the skilled artisan esterifications of N-substituted
- the pesticide preparations of the invention contain one or the a plurality of N-substituted 2-pyrrolidone-4-carboxylic acid derivatives of component b), preferably in amounts of from 0.1 to 50% by weight, more preferably from 0.5 to 30% by weight and especially preferably from 1 to 20 wt .-%. These quantities are based on the entire pesticide preparation according to the invention.
- the pesticidal preparations according to the invention contain the one or more pesticides of component a), preferably in amounts of from 1 to 90% by weight, more preferably from 2 to 80% by weight and especially preferably from 4 to 70% by weight. These quantities are based on the entire pesticide preparation according to the invention.
- the pesticide preparations according to the invention are particularly suitable for controlling and / or controlling weeds, fungal diseases or insect infestation.
- Another object of the present invention is therefore also the use of a pesticide preparation according to the invention for the control and / or control of weeds, fungal diseases or insect infestation.
- the pesticide preparations according to the invention are preferably applied to the fields in the form of spray liquors.
- a spray mixture is prepared by dilution of the concentrate formulation with a defined amount of water.
- the pesticide preparation according to the invention is present as a spray mixture and contains from 0.001 to 10% by weight, preferably from 0.02 to 3% by weight and particularly preferably from 0.025 to
- 2-pyrrolidone-4-carboxylic acid derivatives of component b) to the one or more pesticides of component a) in the spray mixture is preferably from 1: 100 to 10: 1 and more preferably from 1:20 to 4: 1.
- Pesticide amounts are preferably applied in the range of 0.005 to 5 kg per hectare.
- the proportion of N-substituted 2-pyrrolidone-4-carboxylic acid derivatives is in the range of preferably 0.002 to about 2.0 kg / ha.
- the volume of the spray mixture used for the application is preferably in the range from 50 to 1000 l / ha.
- the one or more pesticides and the one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives may also be present in the form of a so-called "tank-mix" preparation
- both the one or more pesticides and the one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives are initially present separately from each other. Both preparations are before
- one or more pesticides are present before mixing as a formulation in water and / or in a solvent or as a solid formulation.
- the one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives are present before mixing in solution in water or in a solvent or a water-solvent mixture.
- the preparations according to the invention may contain thickeners, solvents, dispersants, emulsifiers, preservatives, adjuvants, binders, thinners, disintegrants, wetting agents, penetrants, cold stabilizers, colorants, defoamers and antioxidants.
- thickening agents all commonly used for this purpose in agrochemical formulations substances such as xanthan gum and / or cellulose, for example carboxy, methyl, ethyl or propyl cellulose or (optionally modified) bentonites in the amounts by weight of 0.01 to 5%, based on the finished agent, are used.
- Suitable solvents are all substances customarily usable for this purpose in agrochemical formulations, such as, for example, aromatic and aliphatic hydrocarbons, N-methylpyrrolidone, cyclohexanone, butyrolactone,
- Acetophenone lactic acid esters such as ethyl hexyllactate, esters of carbonic acid such as propylene carbonate, fatty acid amides such as decanoic acid, esters of phosphorous acid or phosphoric acid such as Ethylhexylphosphonklare- (ethylhexyl) ester or tris (ethylhexyl) phosphate, glycols, polyethylene glycols, propylene glycol, natural and mineral oils and Esters of fatty acids.
- Suitable dispersants and emulsifiers are all substances customarily usable for this purpose in agrochemical formulations, such as nonionic, amphoteric, cationic and anionic (polymeric) surfactants.
- Preservatives can all usually be used for this purpose
- substances which can be used in agrochemical formulations such as organic acids and their esters, for example ascorbic acid, ascorbic palmitate, sorbate, benzoic acid, methyl and propyl 4-hydroxybenzoate, propionates, phenol, for example 2-phenylphenate, 1,2-benzisothiazolin-3-one, formaldehyde, Sulfurous acid and its salts are used.
- organic acids and their esters for example ascorbic acid, ascorbic palmitate, sorbate, benzoic acid, methyl and propyl 4-hydroxybenzoate, propionates, phenol, for example 2-phenylphenate, 1,2-benzisothiazolin-3-one, formaldehyde, Sulfurous acid and its salts are used.
- substances which can be used in agrochemical formulations such as organic acids and their esters, for example ascorbic acid, ascorbic palmitate, sorbate, benzoic acid, methyl and propyl 4-hydroxybenzoate, propionates
- alkyl polysaccharides As alcohol ethoxylates, alkyl polysaccharides, fatty amine ethoxylates, esters of phosphorous acid or phosphoric acid such as Ethylhexylphosphonklare- bis (ethylhexyl) ester or tris (ethylhexyl) phosphate, sorbitan and
- Sorbitolethoxylatderivate and derivatives of alk (en) ylsuccinic be used.
- Suitable penetration enhancers are all substances that are commonly used to prevent the penetration of pesticides into plants or in plants
- Penetration enhancers can be defined, for example, by adding them from the aqueous spray mixture and / or from a spray coating on the plant surface into the cuticle of the plant and thereby increase the tissue mobility (mobility) of active ingredients in the cuticle.
- the method described in the literature can be used to determine this property (Baur et al., 1997, Pesticide Science 51, 131-152).
- Polyvinyl pyrrolidone polyvinyl alcohol, carboxymethyl cellulose, sugar,
- sucrose sorbitol or starch.
- Suitable thinners, absorbers or carriers are all substances customarily usable for this purpose in agrochemical formulations, such as carbon black, tallow, kaolin, aluminum, calcium or magnesium stearate, sodium tripolyphosphate,
- Sodium tetraborate, sodium sulphate, silicates and sodium benzoate As disintegrants, it is possible to use all substances customarily usable for this purpose in agrochemical formulations, such as cellulose, for example carboxymethylcellulose, polyvinylpyrrolidone, sodium or potassium acetate, carbonates, bicarbonates, sesquicarbonates, ammonium sulphate or potassium hydrogenphosphate.
- cellulose for example carboxymethylcellulose, polyvinylpyrrolidone, sodium or potassium acetate, carbonates, bicarbonates, sesquicarbonates, ammonium sulphate or potassium hydrogenphosphate.
- wetting agents it is possible to use all substances customarily used for this purpose in agrochemical formulations, such as alcohol ethoxylates,
- Alcohol alkoxylates, EO / PO block copolymers (EO: ethylene oxide unit; PO:
- Propylene glycol unit or optionally ethoxylated alkylsulfonic acids.
- cold stabilizers it is possible to use all substances which can usually be used for this purpose in agrochemical formulations.
- Examples include urea, glycerol and propylene glycol. Suitable colorants are all usually in agrochemical for this purpose
- Formulations usable substances such as water or oil-soluble dyes, as well as organic or inorganic pigments.
- Suitable defoamers are all substances customarily usable for this purpose in agrochemical formulations, such as fatty acid alkyl ester alkoxylates; Organopolysiloxanes such
- the preparations according to the invention may additionally contain one or more agrochemical salts, preferably potassium or ammonium salts. Examples:
- phytotoxicity is made on tomato plants (cv.Astona F1), a species known to be sensitive to phytotoxic substances absorbed via the leaf surface ("Phytotoxicity of different classes of adjuvants", H. de Ruiter, et al., Proceedings Fifth International
- Tomato plants (cv. Astona F1) are housed in a greenhouse
- the pots are placed on an underwater watering mat that has been moistened daily with a medium nutrient solution.
- the plants are treated 28 days after seeding at the 4-leaf stage at a size of 15 - 7 cm per plant.
- the content of excipient in the spray solution is 0.5% (v / v or volume%).
- the spray solutions are applied to the plants with an air pressure operated laboratory sprayer, so that an application amount of 200 l / ha results.
- DAT days after treatment
- the plant mass produced is not reduced when using Compounds 1 and 5 compared to the untreated plant, while the plants treated with the reference substance are weaker, i. H. have a lower plant mass.
- Triethanolamine added to bring the acid into solution.
- glyphosate isopropylammonium with 62% by weight of active ingredient glyphosate IPA salt, IPA: isopropylammonium
- a preparation according to the invention is formed.
- the ratio of glyphosate (based on the acid equivalent) to adjuvant corresponds to that which is also to be found quite thoroughly in commercially available glyphosate formulations.
- the application amount is 135.2 g a.e./ha glyphosate IPA salt (corresponding to 4.0 mmol or 0.68 g a.e./l at a liquid volume of 200 l / ha).
- the abbreviation "a.e.” means "acid equivalent”.
- the spray solutions contain the following concentrations of adjuvant: 0.0141% (v / v).
- Wild oats (Avena Fatua, AVEFA) are exposed to light irradiation in a greenhouse under 14 hours light at a temperature of 18/12 ( ⁇ 0.5) ° C (day / night) and a relative humidity of 70/80 ( ⁇ 5)% (day / Night).
- the light is supplied via high-pressure mercury lamps and fluorescent tubes, so that an output of 70 W / m 2 (PAR, photosynthetically active radiation (400-700 nm)) results at the leaf level.
- the plants are in plastic pots with 11 cm diameter, filled with a mixture of sand and soil (Soil no. 12, Colent bv, Lent, Netherlands) in volume ratio
- the pots are placed on an underwater watering mat, which is moistened daily with a medium nutrient solution. After emergence, the AVEFA sprouts are thinned to six plants per pot for efficacy testing.
- the spray solutions are applied to the plants with an air pressure operated laboratory sprayer, so that an application amount of 200 l / ha results.
- Wild oat (AVEFA) is treated after reaching the 2-3 leaf stage. Results
- Compound 3 and compound 5 are tested for their suitability as emulsifier in EC emulsions (emulsifiable concentrates).
- pesticide preparations according to the invention are prepared with the active ingredients malathion and cypermethrin (Table 4).
- Table 4 Malathion and cypermethrin EC formulations
- Phenylsulfonate CA (Clariant): calcium dodecylbenzenesulfonate in iso-butanol
- Emuslogen ® 3510 (Clariant): EO / PO block copolymer
- Emuisogen ® EL 360 (Clariant): Castor oil ethoxylate
- 5% aqueous emulsions are prepared in soft (20 ppm) and hard (342 ppm) CIPAC standard water and evaluated at 30 ° C for a period of 2, 4, and 24 hours. All emulsions are stable over this period of time, no phase separation is observed.
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Abstract
The invention relates to pesticide preparations that contain one or more pesticides and one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives and to the use of said pesticide preparations for controlling and/or combating weeds, fungal diseases, or insect infestation. The N-substituted 2-pyrrolidone-4-carboxylic acid derivatives act as adjuvants, emulsifiers, dispersants, and/or wetting agents in the pesticide preparations.
Description
Beschreibung description
PESTIZIDZUBEREITU GEN ENTHALTEND DERIVATE VON PYRROLIDON-4-CARBONSÄURE PESTICIDE PREPARATIONS CONTAINING DERIVATIVES OF PYRROLIDONE-4-CARBOXYLIC ACID
Die vorliegende Erfindung betrifft Pestizidzubereitungen, die The present invention relates to pesticide preparations which
Pyrrolidoncarbonsäurederivate enthalten, sowie deren Verwendung, insbesondere zur Kontrolle und/oder Bekämpfung von Unkraut, Pilzerkrankungen oder Pyrrolidoncarbonsäurederivate and their use, in particular for the control and / or control of weeds, fungal diseases or
Insektenbefall. Pestizide werden üblicherweise in Form einer Zubereitung eingesetzt, um eine bessere Ausnutzung des Wirkstoffs zu erzielen. Solche Zubereitungen werden auch als Formulierungen bezeichnet und liegen in der Regel in fester oder in flüssiger Form vor. Die Formulierungen enthalten mindestens einen meist aber mehrere Hilfsstoffe, die verschiedenste Funktionen übernehmen. Insect infestation. Pesticides are commonly used in the form of a preparation to achieve better utilization of the active ingredient. Such preparations are also referred to as formulations and are generally present in solid or in liquid form. The formulations contain at least one but mostly several excipients that take on a variety of functions.
Beispiele für Hilfsstoffe nach ihrer Funktion sind Lösemittel, Emulgatoren, Examples of auxiliaries according to their function are solvents, emulsifiers,
Netzmittel, Dispergiermittel, Kristallisationsinhibitoren, Entschäumer, Wetting agents, dispersants, crystallization inhibitors, defoamers,
Konservierungsmittel, Antioxidantien, Verdicker, Frostschutzmittel, Preservatives, Antioxidants, Thickeners, Antifreeze,
Feuchthaltemittel, Farbmittel und Adjuvants. Unter Adjuvante versteht man Hilfsstoffe, die die biologische Wirksamkeit des Wirkstoffes erhöhen, ohne selbst eine biologische Wirkung zu zeigen, indem sie beispielsweise die Benetzung, die Retention oder die Aufnahme in die Pflanze oder den Zielorganismus verbessern. Humectants, colorants and adjuvants. Adjuvants are understood to mean auxiliaries which increase the biological effectiveness of the active ingredient without itself having a biological effect, for example by improving wetting, retention or uptake into the plant or the target organism.
Beispiele für flüssige Zubereitungen („Formulierungstypen") sind wässrige Examples of liquid preparations ("formulation types") are aqueous
Lösungen (SL), Suspensionskonzentrate (SC), Suspo-Emulsionen (SE), emulgierbare Konzentrate (EC), Öl-Dispersionen (OD), Emulsionen in Wasser (EW) oder Mikroemulsionen (ME). Solutions (SL), suspension concentrates (SC), suspo-emulsions (SE), emulsifiable concentrates (EC), oil dispersions (OD), emulsions in water (EW) or microemulsions (ME).
Beispiele für feste Zubereitungen („Formulierungstypen") sind wasserlösliche Pulver oder Granulate (SP, SG) bzw. wasserdispergierbare Pulver oder Granulate (WP, WDP, WG, WDG).
Viele wirksame Hilfsstoffe, die in Pestizidzubereitungen verwendet werden, sind aus toxikologischer oder ökotoxikologischer Sicht bedenklich, wie Examples of solid formulations ("formulation types") are water-soluble powders or granules (SP, SG) or water-dispersible powders or granules (WP, WDP, WG, WDG). Many effective adjuvants used in pesticide preparations are of concern from a toxicological or ecotoxicological point of view, such as
Nonylphenolethoxylate (aufgrund ihrer endocrinen Wirkung), Fettaminethoxylate (ökotoxische Eigenschaften) oder N-Methylpyrrolidon (reprotoxische Nonylphenol ethoxylates (due to their endocrine effect), fatty amine ethoxylates (ecotoxic properties) or N-methylpyrrolidone (reprotoxic)
Eigenschaften). Properties).
Eine Anforderung an neue Hilfsstoffe in Pestizidzubereitungen ist daher ihre toxikologisch und ökotoxikologische Unbedenklichkeit. Eine weitere wichtige grundsätzliche Anforderung an Hilfsstoffe in A requirement for new excipients in pesticide preparations is therefore their toxicological and ecotoxicological safety. Another important basic requirement for excipients in
Pestizidzubereitungen ist die, keine schädliche Wirkung auf die Nutzpflanze auszuüben (Phytotoxizität). Dies ist vor allem für Fungizide, Insektizide und selektive Herbizide von größter Bedeutung, aber auch für nicht-selektive Pesticidal preparations are those that have no harmful effect on the crop (phytotoxicity). This is especially important for fungicides, insecticides and selective herbicides, but also for non-selective ones
Herbizide, wenn sie beispielsweise bei genmodifizierten Nutzpflanzen verwendet werden, die sich durch eine Resistenz gegenüber den entsprechenden nichtselektiven Herbiziden auszeichnen. Herbicides when used, for example, in genetically modified crops that are resistant to the corresponding nonselective herbicides.
Aufgabe der vorliegenden Erfindung war es daher, Pestizidzubereitungen enthaltend Hilfsstoffe, die sich durch gute Wirksamkeit, toxikologische und ökotoxikologische Unbedenklichkeit und niedrige Phytotoxizität auszeichnen, zur Verfügung zu stellen. It was therefore an object of the present invention to provide pesticide preparations comprising auxiliaries which are distinguished by good activity, toxicological and ecotoxicological safety and low phytotoxicity.
Überraschenderweise wurde nun gefunden, dass diese Aufgabe durch die Verwendung von N-substituierten 2-Pyrrolidon-4-carbonsäure-Derivaten in Pestizidzubereitungen gelöst wird und sich insbesondere N-substituierte Surprisingly, it has now been found that this object is achieved by the use of N-substituted 2-pyrrolidone-4-carboxylic acid derivatives in pesticide preparations and in particular N-substituted
2-Pyrrolidon-4-carbonsäuren, sowie deren Salze, Ester und Amide als wirksame Hilfsstoffe für Pestizidzubereitungen eignen. 2-pyrrolidone-4-carboxylic acids, and their salts, esters and amides are useful as active adjuvants for pesticide preparations.
Gegenstand der vorliegenden Erfindung sind daher Pestizidzubereitungen enthaltend The present invention therefore relates to pesticide preparations containing
a) ein oder mehrere Pestizide und a) one or more pesticides and
b) ein oder mehrere N-substituierte 2-Pyrrolidon-4-carbonsäure-Derivate.
Unter "N-substituierten 2-Pyrrolidon-4-carbonsäure-Derivaten" werden im Rahmen der vorliegenden Erfindung sowohl die N-substituierten 2-Pyrrolidon-4- carbonsäuren als auch andere Derivate wie insbesondere die Salze, Ester und Amide der N-substituierten 2-Pyrrolidon-4-carbonsäuren verstanden. b) one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives. In the context of the present invention, "N-substituted 2-pyrrolidone-4-carboxylic acid derivatives" include both the N-substituted 2-pyrrolidone-4-carboxylic acids and also other derivatives, in particular the salts, esters and amides of the N-substituted 2 Pyrrolidone-4-carboxylic acids understood.
US 2,757,125 beschreibt N-Alkyl-4-carboxy-2-pyrrolidon sowie dessen Salze, bestimmte Alkylester und Alkylamide, die als antibakterielle Komponenten in kosmetischen Formulierungen oder Reinigungsmitteln eingesetzt werden. US 2,977,309 beschreibt ein Schmieröl, das ein Umsetzungsprodukt aus No. 2,757,125 describes N-alkyl-4-carboxy-2-pyrrolidone and its salts, certain alkyl esters and alkylamides which are used as antibacterial components in cosmetic formulations or cleansing compositions. US 2,977,309 describes a lubricating oil which comprises a reaction product
Itaconsäure und verzweigten primären aliphatischen Aminen mit 10-24 C-Atomen, enthält. Itaconic acid and branched primary aliphatic amines with 10-24 C atoms, contains.
In US 3,224,975 werden Schmiermittelzusammensetzungen enthaltend N-Alkyl-4- carboxy-2-pyrrolidon, wobei der Alkylrest 8-25 C-Atome umfasst, beschrieben. No. 3,224,975 describes lubricant compositions comprising N-alkyl-4-carboxy-2-pyrrolidone in which the alkyl radical comprises 8-25 C atoms.
GB 1323061 offenbart bestimmte N-substituierte-4-carboxy-2-pyrrolidone und deren Verwendung in Funktionsflüssigkeiten wie beispielsweise GB 1323061 discloses certain N-substituted-4-carboxy-2-pyrrolidones and their use in functional fluids such as
Hydraulikflüssigkeiten. Hydraulic fluids.
EP 2 022 781 beschreibt dimere N-Alkyl-4-carboxy-2-pyrrolidon-Derivate, die über eine Brücke an der Carboxy-Gruppe verbunden sind und deren Verwendung als Gashydratinhibitoren. EP 2 028 247 beschreibt die Verwendung von N-Alkyl-2-pyrrolidon-4- carbonsäureestern als Gashydratinhibitoren. EP 2 022 781 describes dimeric N-alkyl-4-carboxy-2-pyrrolidone derivatives which are linked via a bridge to the carboxy group and their use as gas hydrate inhibitors. EP 2 028 247 describes the use of N-alkyl-2-pyrrolidone-4-carboxylic acid esters as gas hydrate inhibitors.
WO 2009/086872 und WO 2009/086873 beschreiben die Verwendung von N-Alkyl-2-pyrrolidon-4-carbonsäureammoniumsalzen als Korrosionsinhibitoren. WO 2009/086872 and WO 2009/086873 describe the use of N-alkyl-2-pyrrolidone-4-carboxylic acid ammonium salts as corrosion inhibitors.
Die Verwendung von Pyrrolidoncarbonsäurederivaten als Hilfsstoffe in The use of Pyrrolidoncarbonsäurederivaten as auxiliaries in
Pestizidformulierungen wird jedoch nicht beschreiben.
Unter Pestiziden werden im Rahmen der vorliegenden Erfindung Herbizide, Fungizide, Insektizide, Akarizide, Bakterizide, Molluskide, Nematizide und However, pesticide formulations will not be described. In the context of the present invention, pesticides are herbicides, fungicides, insecticides, acaricides, bactericides, molluscides, nematicides and
Rodentizide sowie Phytohormone verstanden. Phytohormone steuern Rodenticides and phytohormones understood. Controlling phytohormones
physiologische Reaktionen, wie Wachstum, Blührhythmus, Zellteilung und physiological reactions, such as growth, stinging rhythm, cell division and
Samenreifung. Eine Übersicht der relevantesten Pestizide findet sich Seed maturation. An overview of the most relevant pesticides can be found
beispielsweise in„The Pesticide Manual" des British Crop Protection Council, 14th Edition 2006, Editor: C D S Tomlin. for example, in "The Pesticide Manual" of the British Crop Protection Council, 14th Edition 2006, Editor: C D S Tomlin.
Das eine oder die mehreren Pestizide der Komponente a) der The one or more pesticides of component a) of
erfindungsgemäßen Pestizidzubereitungen werden vorzugsweise ausgewählt aus der Gruppe bestehend aus Herbiziden, Insektiziden und Fungiziden. Pesticidal preparations according to the invention are preferably selected from the group consisting of herbicides, insecticides and fungicides.
Bevorzugte Fungizide sind aliphatische Stickstoffungizide, Amidfungizide wie Acylaminosäurefungizide oder Anilidfungizide oder Benzamidfungizide oder Strobilurinfungizide, aromatische Fungizide, Benzimidazolfungizide, Preferred fungicides are aliphatic nitrogen fungicides, amide fungicides such as acylamino acid fungicides or anilide fungicides or benzamide fungicides or strobilurin fungicides, aromatic fungicides, benzimidazole fungicides,
Benzothiazolfungizide, Carbamatfungizide, Conazolfungizide wie Imidazole oder Triazole, Dicarboximidfungizide, Dithiocarbamatfungizide, Imidazolfungizide, Morpholinfungizide, Oxazolfungizide, Pyrazolfungizide, Pyridinfungizide, Benzothiazole fungicides, carbamate fungicides, conazole fungicides such as imidazoles or triazoles, dicarboximide fungicides, dithiocarbamate fungicides, imidazole fungicides, morpholide fungicides, oxazole fungicides, pyrazole fungicides, pyridine fungicides,
Pyrimidinfungizide, Pyrrolfungizide, Chinonfungizide. Pyrimidine fungicides, pyrrole fungicides, quinone fungicides.
Bevorzugte Herbizide sind Amidherbizide, Anilidherbizide, aromatische Preferred herbicides are amide herbicides, anilide herbicides, aromatic
Säureherbizide wie Benzoesäureherbizide oder Picolinisäureherbizide, Acid herbicides such as benzoic acid herbicides or picolinic acid herbicides,
Benzoylcyclohexanedionherbizide, Benzofuranylalkylsulfonatherbizide, Benzoylcyclohexanedione herbicides, benzofuranyl alkyl sulfonate herbicides,
Benzothiazolherbizide, Carbamatherbizide, Carbanilatherbizide, Benzothiazole herbicides, carbamate herbicides, carbanilatherbicide,
Cyclohexenoximherbizide, Cyclopropylisoxazolherbizide, Dicarboximidherbizide, Dinitroanilinherbizide, Dinitrophenolherbizide, Diphenyletherherbizide, Cyclohexenoxime herbicides, cyclopropylisoxazole herbicides, dicarboximide herbicides, dinitroaniline herbicides, dinitrophenol herbicides, diphenyl ether herbicides,
Dithiocarbamatherbizide, Imidazolinonherbizide, Nitrilherbizide, Dithiocarbamate herbicides, imidazolinone herbicides, nitrile herbicides,
Organophosphorherbizide, Oxadiazolonherbizide, Oxazolherbizide, Organophosphorus herbicides, oxadiazolone herbicides, oxazole herbicides,
Phenoxyherbizide wie Phenoxyessigsäureherbizide oder Phenoxy herbicides such as phenoxyacetic acid herbicides or
Phenoxybutansäureherbizide oder Phenoxypropionsäureherbizide oder Phenoxybutanoic acid herbicides or phenoxypropionic acid herbicides or
Aryloxyphenoxypropiosäureherbizide, Pyrazolherbizide wie Aryloxyphenoxypropiosäureherbizide, Pyrazolherbizide like
Benzoylpyrazolherbizide oder Phenylpyrazolherbizide, Pyridazinonherbizide, Pyridinherbizide, Thiocarbamatherbizide, Triazinherbizide, Triazinonherbizide,
Triazolherbizide, Triazolonherbizide, Triazolopyrimidinherbizide, Uracilherbizide, Ureaherbizide wie Phenylharnstoffherbizide oder Sulfonylharnstoffherbizide. Benzoylpyrazole herbicides or phenylpyrazole herbicides, pyridazinone herbicides, pyridine herbicides, thiocarbamate herbicides, triazine herbicides, triazinone herbicides, Triazole herbicides, triazolone herbicides, triazolopyrimidine herbicides, uracil herbicides, urea herbicides such as phenylurea herbicides or sulfonylurea herbicides.
Bevorzugte Insektizide sind Carbamatinsektizide, wie Preferred insecticides are carbamate insecticides, such as
Benzofuranylmethylcarbamat- Insektizide oder Dimethylcarbamat-Insektizide oder Oximcarbamat-Insektizide oder Phenylmethylcarbamatinsektizide, Benzofuranylmethylcarbamate insecticides or dimethylcarbamate insecticides or oximecarbamate insecticides or phenylmethylcarbamate insecticides,
Diamidinsektizide, Insektenwachstumsregulatoren, Macrozyklische Diamidine insecticides, insect growth regulators, macrocyclic
Lactoneinsektizide wie Avermectin-Insektizide oder Milbemycin-Insektizide oder Spinosyninsektizide, Nereistoxin analoge Insektizide, Nicotinoidinsektizide wie Nitroguanidinnicotinoid-Insektizide oder Pyridylmethylaminnicotinoid-Insektizide, Organophosphorinsektizide wie Organophosphatinsektizide oder Lactone insecticides such as avermectin insecticides or milbemycin insecticides or spinosyn insecticides, nereistoxin analogous insecticides, nicotinoid insecticides such as nitroguanidine nicotinoid insecticides or pyridylmethylamino nicotinoid insecticides, organophosphorus insecticides such as organophosphate insecticides or
Organothiophosphatinsektizide oder Phosphonatinsektizide oder Organothiophosphate insecticides or phosphonate insecticides or
Phosphoramidothioatinsektizide, Oxadiazininsektizide, Pyrazolinsektizide, Pyrethroidinsektizide wie Pyrethroidester-Insektizide oder Pyrethroidether- Insektizide oder Pyrethroidoxim-Insektizide, Tetramsäureinsektizide, Phosphoramidothioate insecticides, oxadiazine insecticides, pyrazoline insecticides, pyrethroid insecticides such as pyrethroid ester insecticides or pyrethroid ether insecticides or pyrethroid oxime insecticides, tetramic acid insecticides,
Tetrahydrofurandioninsektizide, Thiazolinsektizide. Tetrahydrofurandione insecticides, thiazoline insecticides.
Besonders bevorzugt wird das eine oder werden die mehreren Pestizide der Komponente a) der erfindungsgemäßen Pestizidzubereitungen ausgewählt aus der Gruppe bestehend aus Aryloxyphenoxypropiosäureherbiziden, The one or more pesticides of component a) of the pesticide preparations according to the invention are particularly preferably selected from the group consisting of aryloxyphenoxypropionic acid herbicides,
Benzoylcyclohexanedionherbiziden, Triazolopyrimidinherbiziden, Strobilurin- Fungiziden, Triazol-Fungiziden, Nicotinoidinsektiziden und Pyrethroidinsektiziden. Benzoylcyclohexanedione herbicides, triazolopyrimidine herbicides, strobilurin fungicides, triazole fungicides, nicotinoid insecticides and pyrethroid insecticides.
Insbesondere bevorzugt wird das eine oder werden die mehreren Pestizide der Komponente a) der erfindungsgemäßen Pestizidzubereitungen ausgewählt aus der Gruppe bestehend aus Malathion, Cypermethrin, Glyphosat in der Säureform und Glyphosat in der Form von Salzen. Hierunter sind Glyphosat in der Säureform und in der Form von Salzen bevorzugt. Unter den Salzen von Glyphosat ist Glyphosat-Isopropylammonium bevorzugt. More preferably, the one or more pesticides of component a) of the pesticide formulations according to the invention are selected from the group consisting of malathion, cypermethrin, glyphosate in the acid form and glyphosate in the form of salts. Among them, preferred are glyphosate in the acid form and in the form of salts. Among the salts of glyphosate, glyphosate isopropylammonium is preferred.
Eine Übersicht der Pestizide sowie deren Einordnung in die entsprechenden Pestizidklassen findet sich beispielsweise in„The Pesticide Manual" des British Crop Protection Council, 14th Edition 2006, Editor: C D S Tomlin.
Die biologische Aktivität eines Pestizides kann anhand des Pflanzenwachstums bzw. der Schädigung der Pflanzen durch die Einwirkung des Wirkstoffes auf das Blatt in Abhängigkeit von der Wirkzeit und der Wirkstoffkonzentration bestimmt werden. An overview of the pesticides and their classification in the corresponding pesticide classes can be found for example in "The Pesticide Manual" of the British Crop Protection Council, 14th Edition 2006, Editor: CDS Tomlin. The biological activity of a pesticide can be determined by the plant growth or the damage to the plants by the action of the active ingredient on the leaf as a function of the time of action and the active ingredient concentration.
Bei dem einen oder den mehreren N-substituierten 2-Pyrrolidon-4-carbonsäure- Derivaten der Komponente b) der erfindungsgemäßen Pestizidzubereitungen handelt es sich vorzugsweise um die N-substituierten, vorzugsweise um die N-Alkyl- oder N-Alkenyl-substituierten, 2-Pyrrolidon-4-carbonsäuren sowie um deren Salze, Ester und Amide. The one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives of component b) of the pesticidal preparations according to the invention are preferably the N-substituted, preferably N-alkyl or N-alkenyl-substituted, 2 Pyrrolidone-4-carboxylic acids and their salts, esters and amides.
Besonders bevorzugt ist das eine oder sind die mehreren N-substituierten Most preferably, the one or more N-substituted ones
2-Pyrrolidon-4-carbonsäure-Derivate der Komponente b) der erfindungsgemäßen Pestizidzubereitungen ausgewählt aus den Verbindungen der Formel (Z) 2-pyrrolidone-4-carboxylic acid derivatives of component b) of the pesticide preparations according to the invention selected from the compounds of the formula (Z)
worin wherein
R1 Cs- bis C30-Alkyl oder C8- bis Cßo-Alkenyl ist, R1 Cs to C 30 alkyl or C 8 - to C ß o-alkenyl,
Y OM, -0-[AO]n-X oder NR2R3 ist, Y is OM, -O- [AO] n is -X or NR2R3,
M Wasserstoff, Alkali- oder Erdalkalimetall, Ammonium NH4 + oder substituiertes Ammonium ist, wobei das substituierte Ammonium vorzugsweise ausgewählt ist aus mono-, di- und trisubstituiertemM is hydrogen, alkali or alkaline earth metal, ammonium NH 4 + or substituted ammonium, wherein the substituted ammonium is preferably selected from mono-, di- and trisubstituted
Ammonium und die Substituenten am N-Atom des substituiertenAmmonium and the substituents on the N atom of the substituted
Ammoniums wiederum ausgewählt sind aus Alkylgruppen mit 1 bis 4 Kohlenstoffatomen und CH2CH2OH, Ammonium are in turn selected from alkyl groups having 1 to 4 carbon atoms and CH 2 CH 2 OH,
A C2- bis C4-Alkylen oder C6H5-(CH-CH2) ist, AC 2 - to C 4 -alkylene or C 6 H 5 - (CH-CH 2 ),
n eine Zahl von 0 bis 100 ist n is a number from 0 to 100
X C bis C2o-Alkyl, Benzyl oder ein substituierter Arylrest ist, wobei der substituierte Arylrest vorzugsweise ausgewählt ist aus Phenyl, das
mit 1 bis 3 Substituenten substituiert ist, und diese Substituenten wiederum ausgewählt sind aus Alkylgruppen mit 1 bis 4 Kohlenstoffatomen und Styryl und in dem Fall, dass n ungleich 0 ist, X auch Wasserstoff bedeuten kann, X is C to C 2 o-alkyl, benzyl or a substituted aryl radical, wherein the substituted aryl radical is preferably selected from phenyl, the is substituted with 1 to 3 substituents, and these substituents are in turn selected from alkyl groups having 1 to 4 carbon atoms and styryl and in the event that n is not 0, X can also be hydrogen,
R2 und R3 unabhängig voneinander Wasserstoff, Ci- bis C2o-Alkyl oder R 2 and R 3 independently of one another are hydrogen, C 1 - to C 2 o-alkyl or
(C2H40)PH sind und (C 2 H 4 0) P H are and
p eine Zahl von 1 bis 20 ist. p is a number from 1 to 20.
In einer insbesondere bevorzugten Ausführungsform der Erfindung ist das eine oder sind die mehreren N-substituierten 2-Pyrrolidon-4-carbonsäure-Derivate der Komponente b) der erfindungsgemäßen Pestizidzubereitungen ausgewählt aus den Verbindungen der Formel (1) In a particularly preferred embodiment of the invention, the one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives of component b) of the pesticidal formulations according to the invention are selected from the compounds of the formula (1)
C8- bis C30-Alkyl oder C8- bis C3o-Alkenyl ist und C 8 to C 30 alkyl or C 8 to C 3 o alkenyl and
Wasserstoff, Alkali- oder Erdalkalimetall, Ammonium NH4 + oder substituiertes Ammonium ist, wobei das substituierte Ammonium vorzugsweise ausgewählt ist aus mono-, di- und trisubstituiertem Ammonium und die Substituenten am N-Atom des substituierten Ammoniums wiederum ausgewählt sind aus Alkylgruppen mit 1 bis 4 Kohlenstoffatomen und CH2CH2OH. In einer weiteren insbesondere bevorzugten Ausführungsform der Erfindung ist das eine oder sind die mehreren N-substituierten 2-Pyrrolidon-4-carbonsäure- Derivate der Komponente b) der erfindungsgemäßen Pestizidzubereitungen ausgewählt aus den Verbindungen der Formel (2)
Is hydrogen, alkali or alkaline earth metal, ammonium NH 4 + or substituted ammonium, wherein the substituted ammonium is preferably selected from mono-, di- and trisubstituted ammonium and the substituents on the N-atom of the substituted ammonium are in turn selected from alkyl groups having 1 to 4 carbon atoms and CH 2 CH 2 OH. In a further particularly preferred embodiment of the invention, the one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives of component b) of the pesticide formulations according to the invention are selected from the compounds of the formula (2)
C8- bis C3o-Alkyl oder Ca- bis C3o-Alkenyl ist, C 8 is - to C 30 -alkyl or C 30 - to C 30 -alkenyl,
C2- bis C4-Alkylen oder C6H5-(CH-CH2) ist, C 2 - to C 4 -alkylene or C 6 H 5 - (CH-CH 2 ),
eine Zahl von 0 bis .100 ist und a number from 0 to . 100 is and
C bis C2o-Alkyl, Benzyl oder ein substituierter Arylrest ist, wobei der substituierte Arylrest vorzugsweise ausgewählt ist aus Phenyl, das mit 1 bis 3 Substituenten substituiert ist, und diese Substituenten wiederum ausgewählt sind aus Alkylgruppen mit 1 bis 4 Kohlenstoffatomen und Styryl und in dem Fall, dass n ungleich 0 ist, X auch Wasserstoff bedeuten kann. C is C 2 to C 20 alkyl, benzyl or a substituted aryl radical, wherein the substituted aryl radical is preferably selected from phenyl substituted with 1 to 3 substituents, and these substituents are in turn selected from alkyl groups having 1 to 4 carbon atoms and styryl and in the If n is not 0, then X can also be hydrogen.
In einer weiteren insbesondere bevorzugten Ausführungsform der Erfindung ist das eine oder sind die mehreren N-substituierten 2-Pyrrolidon-4-carbonsäure- Derivate der Komponente b) der erfindungsgemäßen Pestizidzubereitungen ausgewählt aus den Verbindungen der Formel (3) In a further particularly preferred embodiment of the invention, the one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives of component b) of the pesticide formulations according to the invention are selected from the compounds of the formula (3)
worin wherein
R1 C8- bis C30-Alkyl oder C8- bis C30-Alkenyl ist, R 1 is C 8 - to C 30 -alkyl or C 8 - to C 30 -alkenyl,
R2 und R3 unabhängig voneinander Wasserstoff, C bis C2o-Alkyl oder R2 and R3 are independently hydrogen, C to C 2 o-alkyl or
(C2H40)pH sind und (C 2 H 4 0) p H are and
p eine Zahl von 1 bis 20 ist. p is a number from 1 to 20.
In den Formeln (Z) und (1) bis (3) steht R1 bevorzugt für eine lineare oder
verzweigte Alkyl- oder Alkenylgruppe mit 8 bis 24 Kohlenstoffatomen, In the formulas (Z) and (1) to (3), R1 is preferably a linear or branched alkyl or alkenyl group having 8 to 24 carbon atoms,
insbesondere für eine lineare oder verzweigte Alkyl- oder Alkenylgruppe mit 8 bis 18 Kohlenstoffatomen. Besonders bevorzugt steht R1 für einen linearen oder verzweigten Octylrest, für einen Cocoylrest oder für einen Oleylrest. in particular for a linear or branched alkyl or alkenyl group having 8 to 18 carbon atoms. R1 particularly preferably represents a linear or branched octyl radical, a cocoyl radical or an oleyl radical.
In den Formeln (Z) und (1) steht M bevorzugt für Wasserstoff, Na, K, Ca, In formulas (Z) and (1), M is preferably hydrogen, Na, K, Ca,
Ammonium, iso-Propylammonium, N,N-Diethyl-(2-hydroxyethyl)ammonium, Mono-, Di- oder Triethanolammonium. In den Formeln (Z) und (2) steht A bevorzugt für Ethylen oder Propylen und besonders bevorzugt für Ethylen. X steht bevorzugt für Wasserstoff (wenn n ungleich null ist), C bis C4-Alkyl und besonders bevorzugt für Methyl, n steht bevorzugt für 1 bis 40 und besonders bevorzugt für 5 bis 25. Falls X in den Formeln (Z) und (2) für einen substituierten Arylrest steht, so ist dieser bevorzugt 2,4,6-Tri-sekundär-butylphenyl oder 2,4,6-Tristyrylphenyl. Ammonium, iso-propylammonium, N, N-diethyl (2-hydroxyethyl) ammonium, mono-, di- or triethanolammonium. In the formulas (Z) and (2), A is preferably ethylene or propylene and particularly preferably ethylene. X is preferably hydrogen (when n is not zero), C 4 -C 4 -alkyl and particularly preferably methyl, n is preferably from 1 to 40 and particularly preferably from 5 to 25. If X in the formulas (Z) and ( 2) represents a substituted aryl radical, this is preferably 2,4,6-tri-secondary-butylphenyl or 2,4,6-tristyrylphenyl.
In den Formeln (Z) und (3) stehen R2 und R3 bevorzugt für Wasserstoff, In the formulas (Z) and (3), R 2 and R 3 are preferably hydrogen,
C bis C4-Alkyl oder (C2H40)pH. Besonders bevorzugt stehen R2 und R3 für Methyl oder -CH2-CH2-OH. C to C 4 alkyl or (C 2 H 4 0) p H. Particularly preferred are R2 and R3 is methyl or -CH 2 -CH 2 -OH.
Aufgrund der vielfältigen Möglichkeiten, die chemische Struktur der in den erfindungsgemäßen Pestizidzubereitungen enthaltenen N-substituierten Because of the many possibilities, the chemical structure of the N-substituted contained in the pesticide formulations according to the invention
2-Pyrrolidon-4-carbonsäure-Derivate der Komponente b) zu variieren und damit die physikalischen und physikalisch-chemischen Eigenschaften der Moleküle anzupassen, können die N-substituierten 2-Pyrrolidon-4-carbonsäure-Derivate in den erfindungsgemäßen Zubereitungen die unterschiedlichsten Aufgaben erfüllen. 2-pyrrolidone-4-carboxylic acid derivatives of component b) to vary and thus adapt the physical and physico-chemical properties of the molecules, the N-substituted 2-pyrrolidone-4-carboxylic acid derivatives in the inventive preparations can perform a variety of tasks ,
Dabei eignen sich die N-substituierten 2-Pyrrolidon-4-carbonsäure-Derivate der Komponente b) der erfindungsgemäßen Pestizidzubereitungen und insbesondere die Verbindungen der Formeln (Z) und (1) bis (3) bevorzugt als Adjuvante, The N-substituted 2-pyrrolidone-4-carboxylic acid derivatives of component b) of the pesticide preparations according to the invention and in particular the compounds of the formulas (Z) and (1) to (3) are preferably suitable as adjuvants,
Emulgatoren, Dispergiermittel oder Netzmittel.
Weiterer Gegenstand der vorliegenden Erfindung ist daher die Verwendung eines oder mehrerer N-substituierter 2-Pyrrolidon-4-carbonsäure-Derivate und vorzugsweise eines oder mehrerer N-substituierter 2-Pyrrolidon-4-carbonsäure- Derivate ausgewählt aus den Formeln (Z) und (1) bis (3) als Adjuvant, Emulsifiers, dispersants or wetting agents. Another object of the present invention is therefore the use of one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives and preferably one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives selected from the formulas (Z) and ( 1) to (3) as adjuvant,
vorzugsweise in einer erfindungsgemäßen Pestizidzubereitung. preferably in a pesticide preparation according to the invention.
Weiterer Gegenstand der vorliegenden Erfindung ist auch die Verwendung eines oder mehrerer N-substituierter 2-Pyrrolidon-4-carbonsäure-Derivate und vorzugsweise eines oder mehrerer N-substituierter 2-Pyrrolidon-4-carbonsäure- Derivate ausgewählt aus den Formeln (Z) und (1) bis (3) als Emulgator, vorzugsweise in einer erfindungsgemäßen Pestizidzubereitung. The present invention also provides the use of one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives and preferably one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives selected from the formulas (Z) and ( 1) to (3) as an emulsifier, preferably in a pesticide preparation according to the invention.
Besonders bevorzugte Emulgatoren sind dabei Verbindungen der Formel (1) in denen M ungleich Wasserstoff ist (anionische Emulgatoren) oder Verbindungen der Formel (2) in denen n 5 ist (nicht-ionische Emulgatoren). Particularly preferred emulsifiers are compounds of the formula (1) in which M is not hydrogen (anionic emulsifiers) or compounds of the formula (2) in which n is 5 (nonionic emulsifiers).
Verbindungen der Formel (2) in denen X ungleich Wasserstoff und n 5 ist, eignen sich besonders bevorzugt als Emulgatoren für Pestizidzubereitungen, die einen Wirkstoff enthalten, der empfindlich gegenüber Wasser oder gegenüber OH-Gruppen ist, wie beispielsweise Sulfonylharnstoffe (SUs). Compounds of formula (2) wherein X is other than hydrogen and n is 5 are particularly preferred as emulsifiers for pesticide formulations containing an active ingredient which is sensitive to water or to OH groups, such as sulfonylureas (SUs).
Weiterer Gegenstand der vorliegenden Erfindung ist auch die Verwendung eines oder mehrerer N-substituierter 2-Pyrrolidon-4-carbonsäure-Derivate und vorzugsweise eines oder mehrerer N-substituierter 2-Pyrrolidon-4-carbonsäure- Derivate ausgewählt aus den Formeln (Z) und (1) bis (3) als Netzmittel, vorzugsweise in einer erfindungsgemäßen Pestizidzubereitung. The present invention also provides the use of one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives and preferably one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives selected from the formulas (Z) and ( 1) to (3) as a wetting agent, preferably in a pesticide preparation according to the invention.
Verbindungen der Formel (1) in denen M für Na, K, Ammonium NH4 + oder substituiertes Ammonium steht, eignen sich besonders als Netzmittel. Compounds of the formula (1) in which M represents Na, K, ammonium, NH 4 + or substituted ammonium, are particularly suitable as wetting agents.
Weiterer Gegenstand der vorliegenden Erfindung ist auch die Verwendung eines oder mehrerer N-substituierter 2-Pyrrolidon-4-carbonsäure-Derivate und vorzugsweise eines oder mehrerer N-substituierter 2-Pyrrolidon-4-carbonsäure-
Derivate ausgewählt aus den Formeln (Z) und (1) bis (3) als Dispergiermittel, vorzugsweise in einer erfindungsgemäßen Pestizidzubereitung. Another object of the present invention is the use of one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives and preferably one or more N-substituted 2-pyrrolidone-4-carboxylic acid Derivatives selected from the formulas (Z) and (1) to (3) as a dispersant, preferably in a pesticide preparation according to the invention.
Verbindungen der Formel (1) in denen M für Na, K, Ammonium NH4 + oder substituiertes Ammonium steht, eignen sich besonders als Dispergiermittel. Compounds of the formula (1) in which M is Na, K, ammonium, NH 4 + or substituted ammonium, are particularly suitable as dispersants.
In einer bevorzugten Ausführungsform der Erfindung können die In a preferred embodiment of the invention, the
erfindungsgemäßen Pestizidzubereitungen als flüssige Zubereitungen Pesticidal preparations according to the invention as liquid preparations
(„Formulierungstypen") ausgewählt aus wässrigen Lösungen (SL), ("Formulation types") selected from aqueous solutions (SL),
Suspensionskonzentraten (SC), Suspo-Emulsionen (SE), emulgierbaren Suspension concentrates (SC), suspo-emulsions (SE), emulsifiable
Konzentraten (EC), Öl-Dispersionen (OD), Emulsionen in Wasser (EW) oder Mikroemulsionen (ME) vorliegen. Concentrates (EC), oil dispersions (OD), emulsions in water (EW) or microemulsions (ME) are present.
Verbindungen der Formel (1) in denen M ungleich Wasserstoff ist oder Compounds of the formula (1) in which M is not hydrogen or
Verbindungen der Formel (2) in denen n > 10 ist, eignen sich aufgrund ihrer Löslichkeit besonders bevorzugt zur Verwendung in Wasser enthaltenden Compounds of the formula (2) in which n> 10 are particularly preferred for use in water-containing compounds because of their solubility
Formulierungen wie SLs, SCs, EWs, SEs und MEs. Formulations like SLs, SCs, EWs, SEs and MEs.
Verbindungen der Formel (1) in denen M gleich Wasserstoff ist oder Compounds of formula (1) in which M is hydrogen or
Verbindungen der Formel (2) in denen n < 9 ist oder Verbindungen der Formel (3), weisen eine geringe Löslichkeit in Wasser auf und eignen sich daher besonders bevorzugt als Hilfsmittel für lösemittel- oder ölhaltige Zubereitungen wie ECs, EWs, SEs, MEs und ODs. In einer weiteren bevorzugten Ausführungsform der Erfindung liegen die Compounds of the formula (2) in which n <9 or compounds of the formula (3) have a low solubility in water and are therefore particularly preferably used as auxiliaries for solvent- or oil-containing preparations such as ECs, EWs, SEs, MEs and ODs. In a further preferred embodiment of the invention are the
erfindungsgemäßen Pestizidzubereitungen als feste Zubereitungen Pesticide preparations according to the invention as solid preparations
(„Formulierungstypen") ausgewählt aus wasserlöslichen Pulvern oder Granulaten (SP, SG) bzw. wasserdispergierbaren Pulvern oder Granulaten vor (WP, WDP, WG, WDG). ("Formulation types") selected from water-soluble powders or granules (SP, SG) or water-dispersible powders or granules before (WP, WDP, WG, WDG).
Verbindungen der Formeln (Z) und (1) bis (3), die sich durch einen Schmelzpunkt von bevorzugt > 30 °C und besonders bevorzugt > 40 °C auszeichnen, eignen sich besonders bevorzugt zur Verwendung in festen Zubereitungen.
Weiterer Gegenstand der vorliegenden Erfindung ist auch die Verwendung eines oder mehrerer N-substituierter 2-Pyrrolidon-4-carbonsäure-Derivate und vorzugsweise eines oder mehrerer N-substituierter 2-Pyrrolidon-4-carbonsäure- Derivate ausgewählt aus den Formeln (Z) und (1) bis (3) zur Herstellung von erfindungsgemäßen Pestizidzubereitungen. Compounds of the formulas (Z) and (1) to (3) which are distinguished by a melting point of preferably> 30 ° C. and particularly preferably> 40 ° C., are particularly preferably suitable for use in solid preparations. The present invention also provides the use of one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives and preferably one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives selected from the formulas (Z) and ( 1) to (3) for the preparation of pesticide preparations according to the invention.
Die Herstellung der erfindungsgemäßen Pestitzidzubereitungen ist je nach Formulierungstyp auf verschiedenen Wegen möglich und ist dem Fachmann hinlänglich bekannt. Depending on the type of formulation, the preparation of the pesticide formulations according to the invention is possible in various ways and is well known to the person skilled in the art.
Die N-substituierten 2-Pyrrolidon-4-carbonsäuren der Komponente b) der erfindungsgemäßen Pestizidzubereitungen sind durch Umsetzung von The N-substituted 2-pyrrolidone-4-carboxylic acids of component b) of the pesticide formulations according to the invention are obtained by reacting
Itaconsäure mit primären Aminen zugänglich und können wie in EP 0 069 512, US 3,224,975 und US 4,127,493 beschrieben hergestellt werden. Itaconic acid with primary amines and can be prepared as described in EP 0 069 512, US 3,224,975 and US 4,127,493.
Die Herstellung der entsprechenden Salze ist durch Umsetzung der The preparation of the corresponding salts is by reaction of
N-substituierten 2-Pyrrolidon-4-carbonsäuren mit einer Base möglich. Als Basen eignen sich vorzugsweise NaOH, Ca(OH)2, CaC03, KOH und Amine wie N-substituted 2-pyrrolidone-4-carboxylic acids with a base possible. Suitable bases are preferably NaOH, Ca (OH) 2 , CaC0 3 , KOH and amines such as
Ammoniak, iso-Propylamin, Mono-, Di- oder Triethanolamin. Ammonia, iso-propylamine, mono-, di- or triethanolamine.
Die Herstellung der entsprechenden Ester kann beispielsweise durch Anlagerung von Alkylenoxiden an die N-substituierten 2-Pyrrolidon-4-carbonsäuren oder durch Kondensation der N-substituierten 2-Pyrrolidon-4-carbonsäuren mit The preparation of the corresponding esters can, for example, by addition of alkylene oxides to the N-substituted 2-pyrrolidone-4-carboxylic acids or by condensation of N-substituted 2-pyrrolidone-4-carboxylic acids with
gegebenenfalls substituierten Polyglycolethern erfolgen. Sie kann beispielsweise auch durch dem Fachmann geläufige Veresterungen der N-substituierten optionally substituted polyglycol ethers. It may, for example, by the skilled artisan esterifications of N-substituted
2-Pyrrolidon-4-carbonsäuren mit Alkylalkoholen, Benzylalkohol oder anderen aromatischen Alkoholen erfolgen. Die entsprechenden Amide sind durch Kondensation der N-substituierten 2-pyrrolidone-4-carboxylic acids with alkyl alcohols, benzyl alcohol or other aromatic alcohols. The corresponding amides are by condensation of the N-substituted
2-Pyrrolidon-4-carbonsäuren mit Aminen zugänglich. 2-pyrrolidone-4-carboxylic acids accessible with amines.
Die erfindungsgemäßen Pestizidzubereitungen enthalten das eine oder die
mehreren N-substituierten 2-Pyrrolidon-4-carbonsäure-Derivate der Komponente b) vorzugsweise in Mengen von 0,1 bis 50 Gew.-%, besonders bevorzugt von 0,5 bis 30 Gew.-% und insbesondere bevorzugt von 1 bis 20 Gew.-%. Diese Mengenangaben sind auf die gesamte erfindungsgemäße Pestizidzubereitung bezogen. The pesticide preparations of the invention contain one or the a plurality of N-substituted 2-pyrrolidone-4-carboxylic acid derivatives of component b), preferably in amounts of from 0.1 to 50% by weight, more preferably from 0.5 to 30% by weight and especially preferably from 1 to 20 wt .-%. These quantities are based on the entire pesticide preparation according to the invention.
Die erfindungsgemäßen Pestizidzubereitungen enthalten das eine oder die mehreren Pestizide der Komponente a) vorzugsweise in Mengen von 1 bis 90 Gew.-%, besonders bevorzugt von 2 bis 80 Gew.-% und insbesondere bevorzugt von 4 bis 70 Gew.-%. Diese Mengenangaben sind auf die gesamte erfindungsgemäße Pestizidzubereitung bezogen. The pesticidal preparations according to the invention contain the one or more pesticides of component a), preferably in amounts of from 1 to 90% by weight, more preferably from 2 to 80% by weight and especially preferably from 4 to 70% by weight. These quantities are based on the entire pesticide preparation according to the invention.
Die erfindungsgemäßen Pestizidzubereitungen sind insbesondere zur Kontrolle und/oder Bekämpfung von Unkraut, Pilzerkrankungen oder Insektenbefall geeignet. The pesticide preparations according to the invention are particularly suitable for controlling and / or controlling weeds, fungal diseases or insect infestation.
Weiterer Gegenstand der vorliegenden Erfindung ist daher auch die Verwendung einer erfindungsgemäßen Pestizidzubereitung zur Kontrolle und/oder Bekämpfung von Unkraut, Pilzerkrankungen oder Insektenbefall. Another object of the present invention is therefore also the use of a pesticide preparation according to the invention for the control and / or control of weeds, fungal diseases or insect infestation.
Die erfindungsgemäßen Pestizidzubereitungen werden vorzugsweise in Form von Spritzbrühen auf die Felder ausgebracht. Dabei wird eine Spritzbrühe durch Verdünnung der Konzentrat-Formulierung mit einer definierten Menge Wasser hergestellt. The pesticide preparations according to the invention are preferably applied to the fields in the form of spray liquors. In this case, a spray mixture is prepared by dilution of the concentrate formulation with a defined amount of water.
In einer bevorzugten Ausführungsform der Erfindung liegt die erfindungsgemäße Pestizidzubereitung als Spritzbrühe vor und enthält von 0,001 bis 10 Gew.-%, bevorzugt von 0,02 bis 3 Gew.-% und besonders bevorzugt von 0,025 bis In a preferred embodiment of the invention, the pesticide preparation according to the invention is present as a spray mixture and contains from 0.001 to 10% by weight, preferably from 0.02 to 3% by weight and particularly preferably from 0.025 to
2 Gew.-% Pestizid der Komponente a) und von 0,001 bis 3 Gew.-%, bevorzugt von 0,005 bis 1 Gew.-% und besonders bevorzugt von 0,01 bis 0,5 Gew.-% an N-substituiertem 2-Pyrrolidon-4-carbonsäure-Derivat der Komponente b). Diese Mengenangaben sind auf die gesamte Spritzbrühe bezogen.
Das Gewichtsverhältnis des einen oder der mehreren N-substituierten 2 wt .-% pesticide of component a) and from 0.001 to 3 wt .-%, preferably from 0.005 to 1 wt .-% and particularly preferably from 0.01 to 0.5 wt .-% of N-substituted 2 Pyrrolidone-4-carboxylic acid derivative of component b). These quantities are based on the entire spray mixture. The weight ratio of the one or more N-substituted
2-Pyrrolidon-4-carbonsäure-Derivate der Komponente b) zu dem einen oder den mehreren Pestiziden der Komponente a) in der Spritzbrühe ist vorzugsweise von 1 : 100 bis 10: 1 und besonders bevorzugt von 1 :20 bis 4: 1. 2-pyrrolidone-4-carboxylic acid derivatives of component b) to the one or more pesticides of component a) in the spray mixture is preferably from 1: 100 to 10: 1 and more preferably from 1:20 to 4: 1.
Pro Hektar werden Pestizidmengen vorzugsweise im Bereich von 0,005 bis 5 kg ausgebracht. Der Anteil der N-substituierten 2-Pyrrolidon-4-carbonsäure-Derivate liegt im Bereich von vorzugsweise 0,002 bis ca. 2,0 kg/ha. Das Volumen der für die Ausbringung angesetzten Spritzbrühe liegt bevorzugt im Bereich von 50 bis 1000 l/ha. Pesticide amounts are preferably applied in the range of 0.005 to 5 kg per hectare. The proportion of N-substituted 2-pyrrolidone-4-carboxylic acid derivatives is in the range of preferably 0.002 to about 2.0 kg / ha. The volume of the spray mixture used for the application is preferably in the range from 50 to 1000 l / ha.
Hierbei können das eine oder die mehreren Pestizide und das eine oder die mehreren N-substituierten 2-Pyrrolidon-4-carbonsäure-Derivate auch in Form einer sogenannten„Tank-mix"- Zubereitung vorliegen. In einer derartigen In this case, the one or more pesticides and the one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives may also be present in the form of a so-called "tank-mix" preparation
Zubereitung liegen sowohl das eine oder die mehreren Pestizide als auch das eine oder die mehreren N-substituierten 2-Pyrrolidon-4-carbonsäure-Derivate zunächst getrennt voneinander vor. Beide Zubereitungen werden vor der Preparation, both the one or more pesticides and the one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives are initially present separately from each other. Both preparations are before
Ausbringung, in der Regel kurz vorher, miteinander vermischt, wobei eine erfindungsgemäße Zubereitung entsteht. Application, usually shortly before, mixed together to form a preparation according to the invention.
Im "Tank-mix"-Verfahren liegt das eine oder liegen die mehreren Pestizide vor der Vermischung als Formulierung in Wasser und/oder in einem Lösungsmittel oder als feste Formulierung vor. Im "Tank-mix"-Verfahren liegt das eine oder liegen die mehreren N-substituierten 2-Pyrrolidon-4-carbonsäure-Derivate vor der Vermischung gelöst in Wasser oder in einem Lösungsmittel oder einem Wasser-Lösungsmittelgemisch vor. In the "tank-mix" process, one or more pesticides are present before mixing as a formulation in water and / or in a solvent or as a solid formulation. In the "tank-mix" process, the one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives are present before mixing in solution in water or in a solvent or a water-solvent mixture.
Die erfindungsgemäßen Zubereitungen können Verdickungsmittel, Lösungsmittel, Dispergiermittel, Emulgatoren, Konservierungsmittel, Adjuvants, Bindemittel, Verdünner, Sprengmittel, Netzmittel, Penetrationsförderer, Kältestabilisatoren, Farbmittel, Entschäumer und Antioxidantien enthalten.
Als Verdickungsmittel können alle üblicherweise für diesen Zweck in agrochemischen Formulierungen einsetzbaren Substanzen wie Xanthan gum und/oder Cellulose, beispielsweise Carboxy-, Methyl-, Ethyl- oder Propylcellulose oder (gegebenenfalls modifizierte) Bentonite in den Gewichtsmengen von 0,01 bis 5 %, bezogen auf das fertige Mittel, eingesetzt werden. Als Lösungsmittel eignen sich alle üblicherweise für diesen Zweck in agrochemischen Formulierungen einsetzbaren Substanzen, wie beispielsweise aromatische und aliphatische Kohlenwasserstoffe, N-Methylpyrrolidon, Cyclohexanon, Butyrolacton, The preparations according to the invention may contain thickeners, solvents, dispersants, emulsifiers, preservatives, adjuvants, binders, thinners, disintegrants, wetting agents, penetrants, cold stabilizers, colorants, defoamers and antioxidants. As thickening agents, all commonly used for this purpose in agrochemical formulations substances such as xanthan gum and / or cellulose, for example carboxy, methyl, ethyl or propyl cellulose or (optionally modified) bentonites in the amounts by weight of 0.01 to 5%, based on the finished agent, are used. Suitable solvents are all substances customarily usable for this purpose in agrochemical formulations, such as, for example, aromatic and aliphatic hydrocarbons, N-methylpyrrolidone, cyclohexanone, butyrolactone,
Acetophenon, Milchsäureester wie Ethyl hexyllactat, Ester der Kohlensäure wie Propylencarbonat, Fettsäureamide wie Decansäuredimethylamid, Ester der phosphorigen Säure oder der Phosphorsäure wie Ethylhexylphosphonsäure- bis(ethylhexyl)ester oder Tris(ethylhexyl)phosphat, Glykole, Polyethylenglykole, Propylenglykol, natürliche und mineralische Öle sowie Ester von Fettsäuren. Als Dispergiermittel und Emulgatoren eignen sich alle üblicherweise für diesen Zweck in agrochemischen Formulierungen einsetzbaren Substanzen, wie nichtionische, amphotere, kationische und anionische (polymere) Tenside. Als Acetophenone, lactic acid esters such as ethyl hexyllactate, esters of carbonic acid such as propylene carbonate, fatty acid amides such as decanoic acid, esters of phosphorous acid or phosphoric acid such as Ethylhexylphosphonsäure- (ethylhexyl) ester or tris (ethylhexyl) phosphate, glycols, polyethylene glycols, propylene glycol, natural and mineral oils and Esters of fatty acids. Suitable dispersants and emulsifiers are all substances customarily usable for this purpose in agrochemical formulations, such as nonionic, amphoteric, cationic and anionic (polymeric) surfactants. When
Konservierungsmittel können alle üblicherweise für diesen Zweck in Preservatives can all usually be used for this purpose
agrochemischen Formulierungen einsetzbaren Substanzen wie organische Säuren und ihre Ester, beispielsweise Ascorbinsäure, Ascorbinpalmitat, Sorbat, Benzoesäure, Methyl- und Propyl-4-hydroxybenzoat, Propionate, Phenol, beispielsweise 2-Phenylphenat, 1 ,2-Benzisothiazolin-3-on, Formaldehyd, schwefelige Säure und deren Salze eingesetzt werden. Als Adjuvante können alle üblicherweise für diesen Zweck in agrochemischen Formulierungen einsetzbaren Substanzen wie gegebenenfalls vernetzte Polyglycerinester, Alkoholalkoxylate wie z. B. Alkoholethoxylate, Alkylpolysacharide, Fettaminethoxylate, Ester der phosphorigen Säure oder der Phosphorsäure wie Ethylhexylphosphonsäure- bis(ethylhexyl)ester oder Tris(ethylhexyl)phosphat, Sorbitan- und substances which can be used in agrochemical formulations, such as organic acids and their esters, for example ascorbic acid, ascorbic palmitate, sorbate, benzoic acid, methyl and propyl 4-hydroxybenzoate, propionates, phenol, for example 2-phenylphenate, 1,2-benzisothiazolin-3-one, formaldehyde, Sulfurous acid and its salts are used. As an adjuvant all commonly used for this purpose in agrochemical formulations substances such as optionally crosslinked polyglycerol esters, alcohol alkoxylates such. As alcohol ethoxylates, alkyl polysaccharides, fatty amine ethoxylates, esters of phosphorous acid or phosphoric acid such as Ethylhexylphosphonsäure- bis (ethylhexyl) ester or tris (ethylhexyl) phosphate, sorbitan and
Sorbitolethoxylatderivate und Derivate der Alk(en)ylbernsteinsäure eingesetzt werden. Als Penetrationsförderer eignen sich alle Substanzen, die üblicherweise eingesetzt werden, um das Eindringen von Pestiziden in Pflanzen oder in Sorbitolethoxylatderivate and derivatives of alk (en) ylsuccinic be used. Suitable penetration enhancers are all substances that are commonly used to prevent the penetration of pesticides into plants or in plants
Zielorganismen zu verbessern. Penetrationsförderer können beispielsweise dadurch definiert werden, dass sie aus der wässrigen Spritzbrühe und/oder aus einem Spritzbelag auf der Pflanzenoberfläche in die Kutikula der Pflanze
eindringen und dadurch die Stoffbeweglichkeit (Mobilität) von Wirkstoffen in der Kutikula erhöhen können. Die in der Literatur beschriebene Methode kann zur Bestimmung dieser Eigenschaft eingesetzt werden (Baur et al., 1997, Pesticide Science 51 , 131-152). To improve target organisms. Penetration enhancers can be defined, for example, by adding them from the aqueous spray mixture and / or from a spray coating on the plant surface into the cuticle of the plant and thereby increase the tissue mobility (mobility) of active ingredients in the cuticle. The method described in the literature can be used to determine this property (Baur et al., 1997, Pesticide Science 51, 131-152).
Für feste Formulierungen kommen alle üblicherweise für diesen Zweck in agrochemischen Formulierungen einsetzbaren Bindemittel in Frage wie For solid formulations, all binders customarily used for this purpose in agrochemical formulations are suitable, such as
Polyvinylpyrrolidon, Polyvinylalkohol, Carboxymethylcellulose, Zucker, Polyvinyl pyrrolidone, polyvinyl alcohol, carboxymethyl cellulose, sugar,
beispielsweise Sucrose, Sorbitol oder Stärke. Als Verdünner, Absorber oder Träger eignen sich alle üblicherweise für diesen Zweck in agrochemischen Formulierungen einsetzbaren Substanzen wie Carbon Black, Talg, Kaolin, Aluminium-, Calcium- oder Magnesiumstearat, Natriumtripolyphosphat, For example, sucrose, sorbitol or starch. Suitable thinners, absorbers or carriers are all substances customarily usable for this purpose in agrochemical formulations, such as carbon black, tallow, kaolin, aluminum, calcium or magnesium stearate, sodium tripolyphosphate,
Natriumtetraborat, Natriumsulphat, Silikate und Natriumbenzoat. Als Sprengmittel wirken alle üblicherweise für diesen Zweck in agrochemischen Formulierungen einsetzbaren Substanzen wie Cellulose, beispielsweise Carboxymethylcellulose, Polyvinylpyrrolidon, Natrium- oder Kaliumacetat, Carbonate, Bicarbonate, Sesquicarbonate, Ammoniumsulphat oder Kaliumhydrogenphosphat. Sodium tetraborate, sodium sulphate, silicates and sodium benzoate. As disintegrants, it is possible to use all substances customarily usable for this purpose in agrochemical formulations, such as cellulose, for example carboxymethylcellulose, polyvinylpyrrolidone, sodium or potassium acetate, carbonates, bicarbonates, sesquicarbonates, ammonium sulphate or potassium hydrogenphosphate.
Als Netzmittel können alle üblicherweise für diesen Zweck in agrochemischen Formulierungen einsetzbaren Substanzen, wie Alkoholethoxylate, As wetting agents, it is possible to use all substances customarily used for this purpose in agrochemical formulations, such as alcohol ethoxylates,
Alkoholalkoxylate, EO/PO-Blockcopolymere (EO: Ethylenoxid-Einheit; PO: Alcohol alkoxylates, EO / PO block copolymers (EO: ethylene oxide unit; PO:
Propylenglykol-Einheit) oder gegebenenfalls ethoxylierte Alkylsulfonsäuren verwendet werden. Als Kältestabilisatoren können alle üblicherweise für diesen Zweck in agrochemischen Formulierungen einsetzbaren Stoffe fungieren. Propylene glycol unit) or optionally ethoxylated alkylsulfonic acids. As cold stabilizers, it is possible to use all substances which can usually be used for this purpose in agrochemical formulations.
Beispielhaft seien Harnstoff, Glycerin und Propylenglykol genannt. Geeignete Farbmittel sind alle üblicherweise für diesen Zweck in agrochemischen Examples include urea, glycerol and propylene glycol. Suitable colorants are all usually in agrochemical for this purpose
Formulierungen einsetzbaren Substanzen wie wasser- oder öllösliche Farbstoffe, sowie organische oder anorganische Pigmente. Als Entschäumer eignen sich alle üblicherweise für diesen Zweck in agrochemischen Formulierungen einsetzbaren Substanzen, wie Fettsäurealkylesteralkoxylate; Organopolysiloxane wie Formulations usable substances such as water or oil-soluble dyes, as well as organic or inorganic pigments. Suitable defoamers are all substances customarily usable for this purpose in agrochemical formulations, such as fatty acid alkyl ester alkoxylates; Organopolysiloxanes such
Polydimethylsiloxane und deren Gemische mit mikrofeiner, gegebenenfalls signierter Kieselsäure; Perfluoralkylphosphonate und -phosphinate; Paraffine; Wachse und Mikrokristallinwachse und deren Gemische mit signierter
Kieselsäure. Vorteilhaft sind auch Gemische verschiedener Schauminhibitoren, beispielsweise solche aus Silikonöl, Paraffinöl und/oder oder Wachsen. Als Antioxidantien kommen alle üblicherweise für diesen Zweck in agrochemischen Formulierungen einsetzbaren Substanzen in Betracht, wie beispielsweise BHT (2,6-Di-tert.-butyl-4-methylphenol). Polydimethylsiloxanes and their mixtures with microfine, optionally signed silica; Perfluoroalkyl phosphonates and phosphinates; paraffins; Waxes and microcrystalline waxes and their mixtures with signed Silica. Also advantageous are mixtures of various foam inhibitors, for example those of silicone oil, paraffin oil and / or waxes. Suitable antioxidants are all substances customarily usable for this purpose in agrochemical formulations, for example BHT (2,6-di-tert-butyl-4-methylphenol).
Die erfindungsgemäßen Zubereitungen können darüber hinaus ein oder mehrere agrochemische Salze, bevorzugt Kalium- oder Ammoniumsalze, enthalten. Beispiele: The preparations according to the invention may additionally contain one or more agrochemical salts, preferably potassium or ammonium salts. Examples:
Im Folgenden wird die Erfindung anhand von Beispielen verdeutlicht, die jedoch keinesfalls als Einschränkung anzusehen sind. In den Beispielen bedeuten %-Angaben Gewichtsprozent (Gew.-%), sofern nicht explizit anders angegeben. In the following, the invention will be clarified by way of examples, which are by no means to be regarded as limiting. In the examples, percentages% by weight (% by weight) unless explicitly stated otherwise.
Allgemeine Vorschrift zur Herstellung der N-substituierten 2-Pyrrolidon-4- carbonsäuren: General procedure for the preparation of the N-substituted 2-pyrrolidone-4-carboxylic acids:
In einer 2 Liter-Rührapparatur mit Rückflusskühler und Wechselvorstoß wird primäres Amin vorgelegt und unter Stickstoff Überleitung auf 100 °C erwärmt. Bei dieser Temperatur wird die entsprechende Menge Itaconsäure in fünf gleich großen Portionen unter langsamem Rühren eingetragen. Die Mischung reagiert exotherm, nach jeder Portion wird 30 Minuten nachgerührt. Danach wird die Reaktionsmischung aufgeheizt bis Rückfluss erreicht wird (ca. 120 °C) und 6 Stunden unter Rückfluss gehalten. Anschließend wird am Wechselvorstoß auf Abnahme des Reaktionswassers umgestellt. Die Temperatur wird innerhalb von 4 Stunden schrittweise auf 180 °C erhöht und das Reaktionswasser in der Vorlage gesammelt. In a 2-liter stirred apparatus with reflux condenser and change-over, primary amine is initially charged and heated to 100 ° C. under nitrogen. At this temperature, the corresponding amount of itaconic acid is added in five equal portions with slow stirring. The mixture reacts exothermically, after each serving is stirred for 30 minutes. Thereafter, the reaction mixture is heated until reflux is reached (about 120 ° C) and held under reflux for 6 hours. Subsequently, the changeover thrust is changed over to a decrease in the water of reaction. The temperature is gradually increased within 4 hours to 180 ° C and the reaction water collected in the template.
Beispiel 1 : Example 1 :
Gemäß obiger Vorschrift werden 773,1 g primäres Oleylamin (M = 264,7 g/mol,
Genamin OL 100D der Firma Clariant) und 400,0 g Itaconsäure (M = 130,1 g/mol) umgesetzt. Dabei werden 50,2 g Wasser ausgetragen. Das erhaltene Produkt weist eine Säurezahl von 142,3 mg KOH/g auf According to the above instructions, 773.1 g of primary oleylamine (M = 264.7 g / mol, Genamin OL 100D from Clariant) and 400.0 g of itaconic acid (M = 130.1 g / mol). This 50.2 g of water are discharged. The product obtained has an acid number of 142.3 mg KOH / g
(Theorie: 148,9 mg KOH/g). Der Wassergehalt liegt bei < 0,05 %. Man erhält 1072,7 g N-Oleyl-2-pyrrolidon-4-carbonsäure (Verbindung 1). (Theory: 148.9 mg KOH / g). The water content is <0.05%. This gives 1072.7 g of N-oleyl-2-pyrrolidone-4-carboxylic acid (compound 1).
Beispiel 2: Example 2:
Gemäß obiger Vorschrift werden 683,5 g primäres Cocosfettamin According to the above rule, 683.5 g of primary coconut fatty amine are added
(M = 195,5 g/mol, Genamin® CC 100D der Firma Clariant) und 478,8 g (M = 195.5 g / mol, Genamin ® CC 100D from Clariant), and 478.8 g
Itaconsäure (M = 130,1 g/mol) umgesetzt. Dabei werden 66,9 g Wasser ausgetragen. Das erhaltene Produkt weist eine Säurezahl von 173,0 mg KOH/g auf (Theorie: 182,4 mg KOH/g). Der Wassergehalt liegt bei < 0,05 %. Man erhält 1050,1 g N-Cocoyl-2-pyrrolidon-4-carbonsäure (Verbindung 2). Vorschrift zur Herstellung von N-substituierten 2-Pyrrolidon-4-carbonsäureestern: Itaconic acid (M = 130.1 g / mol) reacted. This 66.9 g of water are discharged. The product obtained has an acid number of 173.0 mg KOH / g (theory: 182.4 mg KOH / g). The water content is <0.05%. This gives 1050.1 g of N-cocoyl-2-pyrrolidone-4-carboxylic acid (compound 2). Procedure for the preparation of N-substituted 2-pyrrolidone-4-carboxylic esters:
In einer 1 Liter-Rührapparatur mit Rückflusskühler, Wechselvorstoß und In a 1 liter stirrer with reflux condenser, changeover thrust and
Stickstoffüberleitung wird die N-substituierte 2-Pyrrolidon-4-carbonsäure und Polyethylenglykolmonomethylether (Polyglykol M-Typen der Firma Clariant) im Molverhältnis 1 :1 vorgelegt und auf 200 °C unter Rühren erwärmt. Bei dieser Temperatur wird weitere 4 Stunden gerührt und Reaktionswasser abdestilliert. Dann wird vorsichtig Wasserstrahlvakuum (22 mbar) angelegt und auf 220 °C erwärmt. Wenn die gewünschte Restsäurezahl erreicht ist, wird das Vakuum mit Stickstoff aufgehoben und abkühlen lassen. Die einzelnen Versuche sind in Tabelle 1 zusammengefasst.
Tabelle 1 : Umsetzungen von N-substituierten 2-Pyrrolidon-4-carbonsäuren mit PolyethylenglykolmonomethylethernNitrogen transfer, the N-substituted 2-pyrrolidone-4-carboxylic acid and polyethylene glycol monomethyl ether (Polyglykol M types from Clariant) in a molar ratio of 1: 1 and heated to 200 ° C with stirring. At this temperature, stirring is continued for a further 4 hours and water of reaction is distilled off. Then a gentle water jet vacuum (22 mbar) is applied and heated to 220 ° C. When the desired residual acid number has been reached, the vacuum is released with nitrogen and allowed to cool. The individual experiments are summarized in Table 1. Table 1: Reactions of N-substituted 2-pyrrolidone-4-carboxylic acids with polyethylene glycol monomethyl ethers
Beispiel Pyrrolidon- EinsatzPolyglykol M Molmasse EinsatzRestsäurezahl Hydroxylzahl Ausbeute Aussehen carbonsäure menge Polyglykol M menge Endprodukt Endprodukt Endprodukt Example Pyrrolidone Use Polyglycol M Molecular Weight Use Residual Acid Number Hydroxyl Number Yield Appearance Carboxylic Acid Amount Polyglycol M Amount Final Product End Product End Product
[g] [g/mol] [g] [mg KOH/g] [mg KOH/g] [g] bei RT [g] [g / mol] [g] [mg KOH / g] [mg KOH / g] [g] at RT
Beispiel 3 Example 3
Verbindung 1 420,0 250 283-295 303,2 2,1 nicht bestimmt 682,7 flüssig (Verbindung 3) Compound 1 420.0 250 283-295 303.2 2.1 not determined 682.7 liquid (compound 3)
Beispiel 4 Example 4
Verbindung 1 380,0 350 330-370 329,0 2,3 nicht bestimmt 664,2 flüssig (Verbindung 4) Compound 1 380.0 350 330-370 329.0 2.3 not determined 664.2 liquid (compound 4)
Beispiel 5 Example 5
Verbindung 1 387,5 500 470-530 312,5 1 ,7 4,2 665,0 flüssig (Verbindung 5) Compound 1 387.5 500 470-530 312.5 1, 7 4.2 665.0 liquid (compound 5)
Beispiel 6 Example 6
Verbindung 1 238,7 750 720-780 462,3 0,6 4,7 676,5 pastös (Verbindung 6) Compound 1 238.7 750 720-780 462.3 0.6 4.7 676.5 pasty (compound 6)
Beispiel 7 Example 7
Verbindung 1 193,8 1000 970-1060 506,2 0,3 nicht bestimmt 677,1 fest (Verbindung 7) Compound 1 193.8 1000 970-1060 506.2 0.3 not determined 677.1 solid (compound 7)
Beispiel 8 Example 8
Verbindung 2 279,2 500 470-530 420,7 1 ,3 4,9 643,3 flüssig (Verbindung 8) Compound 2 279.2 500 470-530 420.7 1, 3 4.9 643.3 liquid (compound 8)
Beispiel 9 Example 9
Verbindung 2 208,7 750 720-780 491 ,2 0,7 6,0 653,7 pastös (Verbindung 9) Compound 2 208.7 750 720-780 491, 2 0.7 6.0 653.7 pasty (compound 9)
Beispiel 10 Example 10
Verbindung 2 167,7 1000 970-1060 532,4 1 ,1 5,8 663,4 pastös (Verbindung 10)
Compound 2 167.7 1000 970-1060 532.4 1, 1 5.8 663.4 pasty (compound 10)
Vorschrift zur Herstellung von Salzen der N-substituierten 2-Pyrrolidon-4- carbonsäuren: Procedure for the preparation of salts of N-substituted 2-pyrrolidone-4-carboxylic acids:
Beispiel 11 : Example 11:
379 g N-Oleyl-2-pyrrolidon-4-carbonsäure (Verbindung 1) wird mit 61 g 379 g of N-oleyl-2-pyrrolidone-4-carboxylic acid (compound 1) is mixed with 61 g
Monoethanolamin umgesetzt. Es werden 440 g N-Oleyl-2-pyrrolidon-4- carbonsäure Monoethanolammoniumsalz (Verbindung 11) mit Säurezahl = 125 mg KOH/g und basischer Stickstoff N = 3,3 % erhalten. Beispiel 12: Monoethanolamine implemented. There are obtained 440 g of N-oleyl-2-pyrrolidone-4-carboxylic acid monoethanolammonium salt (compound 11) with acid number = 125 mg KOH / g and basic nitrogen N = 3.3%. Example 12:
311 g N-Cocoyl-2-pyrrolidon-4-carbonsäure (Verbindung 2) wird mit 117 g 311 g of N-cocoyl-2-pyrrolidone-4-carboxylic acid (compound 2) is mixed with 117 g
Ν,Ν-Diethylaminoethanol umgesetzt. Es werden 428 g N-Cocoyl-2-pyrrolidon-4- carbonsäure N,N-Diethyl-(2-hydroxyethyl)ammoniumsalz (Verbindung 12) mit Säurezahl = 125 mg KOH/g und basischer Stickstoff N = 3,3 % erhalten. Ν, Ν-Diethylaminoethanol reacted. There are obtained 428 g of N-cocoyl-2-pyrrolidone-4-carboxylic acid N, N-diethyl (2-hydroxyethyl) ammonium salt (compound 12) with acid number = 125 mg KOH / g and basic nitrogen N = 3.3%.
Beispiel 13: Umsetzung der N-substituierten 2-Pyrrolidon-4-carbonsäuren mit Example 13: Reaction of the N-substituted 2-pyrrolidone-4-carboxylic acids with
Dimethylamin: dimethylamine:
In einer 1 Liter-Rührapparatur mit Rückflusskühler und Wechselvorstoß werden 2 mol der N-substituierten 2-Pyrrolidon-4-carbonsäure vorgelegt und unter Erwärmen auf 180 °C gasförmiges Dimethylamin eingeleitet und kontinuierlich das gebildete Reaktionswasser abdestilliert. Sobald die Restsäurezahl auf 2 mol of the N-substituted 2-pyrrolidone-4-carboxylic acid are initially introduced into a 1 liter stirred apparatus with reflux condenser and alternating projection and gaseous dimethylamine is introduced with heating to 180 ° C. and the reaction water formed is distilled off continuously. Once the residual acid number on
< 5 mg KOH/g gefallen ist (nach ca. 20 Stunden), wird die Einleitung des <5 mg KOH / g has fallen (after about 20 hours), the initiation of the
Dimethylamins gestoppt und das überschüssige Dimethylamin durch Dimethylamine stopped and the excess dimethylamine through
Stickstoffeinleitung unter Vakuum ausgetrieben. Anschließend wird die Nitrogen discharge expelled under vacuum. Subsequently, the
Reaktionsmischung unter Stickstoffüberleitung abgekühlt. Reaction mixture cooled under nitrogen transfer.
Beispiel 14: Bestimmung der Phytotoxizität Example 14: Determination of phytotoxicity
Die Bestimmung der Phytotoxizität erfolgt an Tomatenpflanzen (cv. Astona F1), eine Spezies, die bekanntermaßen empfindlich auf über die Blattoberfläche aufgenommene phytotoxische Substanzen reagiert („Phytotoxicity of different classes of adjuvants", H. de Ruiter, et al., Proceedings Fifth International The determination of phytotoxicity is made on tomato plants (cv.Astona F1), a species known to be sensitive to phytotoxic substances absorbed via the leaf surface ("Phytotoxicity of different classes of adjuvants", H. de Ruiter, et al., Proceedings Fifth International
Symposium on Adjuvants for Agrochemicals, 1998, Ed. P. McMullan, Symposium on Adjuvants for Agrochemicals, 1998, Ed. P. McMullan,
pp. 204-209).
Pflanzen pp. 204-209). plants
Tomatenpflanzen (cv. Astona F1) werden in einem Gewächshaus unter Tomato plants (cv. Astona F1) are housed in a greenhouse
14 Stunden Lichtbestrahlung bei einer Temperatur von 18/12 (± 0,5) °C 14 hours of light irradiation at a temperature of 18/12 (± 0.5) ° C
(Tag/Nacht) und einer relativen Luftfeuchtigkeit von 70/80 (± 5) % (Tag/Nacht) aufgezogen. 12 Tage nach dem Keimen werden die Setzlinge in Plastiktöpfe mit 11 cm Durchmesser (eine Pflanze pro Topf), gefüllt mit einer Mischung aus Sand und Erde (Soil no. 12, Colent b.v., Lent, Niederlande) im Volumenverhältnis Sand : Erde = 1 : 2, ausgesetzt. (Day / night) and a relative humidity of 70/80 (± 5)% (day / night). 12 days after germination, the seedlings are placed in 11 cm diameter plastic pots (one plant per pot) filled with a mixture of sand and soil (Soil no. 12, Colent bv, Lent, The Netherlands) in the volume ratio of sand: soil = 1: 2, exposed.
Die Töpfe werden auf eine Unterbodenbewässerungsmatte platziert, die täglich mit einer mittelstarken Nährmittellösung befeuchtet wurde. The pots are placed on an underwater watering mat that has been moistened daily with a medium nutrient solution.
Applikation application
Die Pflanzen werden 28 Tage nach erfolgter Aussaat im 4-Blatt-Stadium bei einer Größe von 15 - 7 cm je Pflanze behandelt. Der Gehalt an Hilfsstoff in der Sprühlösung beträgt 0,5 % (v/v bzw. Volumen-%). The plants are treated 28 days after seeding at the 4-leaf stage at a size of 15 - 7 cm per plant. The content of excipient in the spray solution is 0.5% (v / v or volume%).
Die Sprühlösungen werden mit einem Luftdruck betriebenen Laborsprüher auf die Pflanzen appliziert, so dass eine Applikationsmenge von 200 l/ha resultiert. The spray solutions are applied to the plants with an air pressure operated laboratory sprayer, so that an application amount of 200 l / ha results.
Die behandelten Pflanzen werden visuell nach 2 und 8 Tagen (DAT; DAT: days after treatment) begutachtet und anhand einer qualitativen Einstufung (1 bis 5) bewertet. Dabei bedeutet 1 = keine Verfärbung oder Nekrose der Blätter bis 5 = vollständige Nekrose der behandelten Blattoberfläche. Außerdem wird die über dem Boden befindliche Pflanzenmasse nach 8 Tagen (Fresh Weight) bestimmt. Dabei werden jeweils die Durchschnittswerte bezogen auf die Anzahl der behandelten Pflanzen gebildet. Als Referenzsubstanz wird ein The treated plants are visually assessed after 2 and 8 days (DAT: days after treatment) and evaluated on the basis of a qualitative classification (1 to 5). 1 = no discoloration or necrosis of the leaves until 5 = complete necrosis of the treated leaf surface. In addition, the plant mass above the ground is determined after 8 days (Fresh Weight). In each case, the average values are calculated based on the number of treated plants. As reference substance is a
Fettalkoholalkoxylat verwendet, wie es auch in Pestizidzubereitungen einsetzt wird. Die Ergebnisse sind in Tabelle 2 dargestellt.
Tabelle 2: Ergebnisse der Behandlung der Pflanze cv. Astona F1 mit Fatty alcohol alkoxylate used, as it is used in pesticide formulations. The results are shown in Table 2. Table 2: Results of treatment of the plant cv. Astona F1 with
N-substituierten 2-Pyrrolidon-4-carbonsäure-Derivaten und N-substituted 2-pyrrolidone-4-carboxylic acid derivatives and
Fettalkoholalkoxylat, jedoch ohne Pestizid Fatty alcohol alkoxylate, but without pesticide
Die Verbindungen 1 und 5 zeigen höchstens minimale Anzeichen einer Compounds 1 and 5 show at most minimal signs of
phytotoxischen Reaktion der Tomatenpflanzen, während die Referenzsubstanz deutliche Reaktionen hervorruft. Die gebildete Pflanzenmasse ist bei Verwendung der Verbindungen 1 und 5 im Vergleich zur unbehandelten Pflanze nicht reduziert, während die mit der Referenzsubstanz behandelten Pflanzen schwächer ausgebildet sind, d. h. eine niedrigere Pflanzenmasse aufweisen. phytotoxic reaction of the tomato plants, while the reference substance causes significant reactions. The plant mass produced is not reduced when using Compounds 1 and 5 compared to the untreated plant, while the plants treated with the reference substance are weaker, i. H. have a lower plant mass.
Beispiel 15: Pestizidzubereitungen, Erhöhung der biologischen Wirksamkeit von Example 15: Pesticidal Preparations, Increasing the Biological Activity of
Glyphosat glyphosate
Sprühlösungen Spray solutions
Verbindung 1 und Verbindung 5 werden auf ihre Eignung als Adjuvant für das Herbizid Glyphosat im sogenannten Tank-mix-Verfahren getestet. Dabei werden 50 %ige Lösungen eingesetzt. Im Falle von Verbindung 1 wird zusätzlich Compound 1 and compound 5 are tested for their suitability as adjuvants for the herbicide glyphosate in the so-called tank-mix method. In this case, 50% solutions are used. In the case of compound 1 is in addition
Triethanolamin zugegeben, um die Säure in Lösung zu bringen. Triethanolamine added to bring the acid into solution.
Durch Mischen dieser Tank-mix-Lösungen mit einer handelsüblichen wässrigen Lösung von Glyphosat Isopropylammonium (mit 62 Gew.-% Wirkstoff Glyphosat IPA-Salz; IPA: Isopropylammonium) und weiterer Zugabe von Wasser entsteht eine erfindungsgemäße Zubereitung. Das Verhältnis von Glyphosat (bezogen auf
das Säureäquivalent) zu Adjuvant entspricht dabei dem, wie es auch durchaus in kommerziell erhältlichen Glyphosat-Formulierungen zu finden ist. By mixing these tank-mix solutions with a commercially available aqueous solution of glyphosate isopropylammonium (with 62% by weight of active ingredient glyphosate IPA salt, IPA: isopropylammonium) and further addition of water, a preparation according to the invention is formed. The ratio of glyphosate (based on the acid equivalent) to adjuvant corresponds to that which is also to be found quite thoroughly in commercially available glyphosate formulations.
Zur besseren Überprüfung der Adjuvant-Effekte wird Glyphosat unterdosiert, die Applikationsmenge beträgt 135,2 g a.e./ha Glyphosat IPA-Salz (entsprechend 4,0 mMol oder 0,68 g a.e./l bei einem Flüssigkeitsvolumen von 200 l/ha). Die Abkürzung "a.e." bedeutet "acid equivalent". For a better check of the adjuvant effects glyphosate is underdosed, the application amount is 135.2 g a.e./ha glyphosate IPA salt (corresponding to 4.0 mmol or 0.68 g a.e./l at a liquid volume of 200 l / ha). The abbreviation "a.e." means "acid equivalent".
Die Sprühlösungen enthalten folgende Konzentrationen an Adjuvant: 0,0141 % (v/v). The spray solutions contain the following concentrations of adjuvant: 0.0141% (v / v).
Pflanzen plants
Flughafer (Avena Fatua, AVEFA) wird in einem Gewächshaus unter 14 Stunden Lichtbestrahlung bei einer Temperatur von 18/12 (± 0,5) °C (Tag/Nacht) und einer relativen Luftfeuchtigkeit von 70/80 (± 5) % (Tag/Nacht) aufgezogen. Das Licht wird über Quecksilber-Hochdrucklampen und fluoreszierende Röhren zugeführt, so dass sich eine Leistung von 70 W/m2 (PAR; PAR: photosynthetically active radiation (400 - 700 nm)) auf dem Blattniveau ergibt. Die Pflanzen werden in Plastiktöpfen mit 11 cm Durchmesser, gefüllt mit einer Mischung aus Sand und Erde (Soil no. 12, Colent b.v., Lent, Niederlande) im Volumenverhältnis Wild oats (Avena Fatua, AVEFA) are exposed to light irradiation in a greenhouse under 14 hours light at a temperature of 18/12 (± 0.5) ° C (day / night) and a relative humidity of 70/80 (± 5)% (day / Night). The light is supplied via high-pressure mercury lamps and fluorescent tubes, so that an output of 70 W / m 2 (PAR, photosynthetically active radiation (400-700 nm)) results at the leaf level. The plants are in plastic pots with 11 cm diameter, filled with a mixture of sand and soil (Soil no. 12, Colent bv, Lent, Netherlands) in volume ratio
Sand : Erde = 1 : 2, gezüchtet. Sand: Soil = 1: 2, bred.
Die Töpfe werden auf eine Unterbodenbewässerungsmatte platziert, die täglich mit einer mittelstarken Nährmittellösung befeuchtet wird. Nach dem Erscheinen werden die AVEFA-Sprösslinge für die Wirksamkeitstests auf sechs Pflanzen pro Topf ausgedünnt. The pots are placed on an underwater watering mat, which is moistened daily with a medium nutrient solution. After emergence, the AVEFA sprouts are thinned to six plants per pot for efficacy testing.
Herbizidapplikation herbicide application
Mit den Sprühlösungen werden Gewächshausversuche durchgeführt. Es wird der Einfluss der Adjuvantien auf die Wirksamkeit von Glyphosat getestet. Greenhouse experiments are carried out with the spray solutions. The influence of the adjuvants on the efficacy of glyphosate is tested.
Die Sprühlösungen werden mit einem Luftdruck betriebenen Laborsprüher auf die Pflanzen appliziert, so dass eine Applikationsmenge von 200 l/ha resultiert.
Flughafer (AVEFA) wird nach Erreichen des 2-3-Blattstadiums behandelt. Ergebnisse The spray solutions are applied to the plants with an air pressure operated laboratory sprayer, so that an application amount of 200 l / ha results. Wild oat (AVEFA) is treated after reaching the 2-3 leaf stage. Results
Nach 21 Tagen wird die Herbizid-Wirksamkeit beurteilt. Dazu wird die Masse der verbliebenen überirdischen Pflanzenteile (sog. fresh weight (FW) in Gramm) bestimmt. Diese ist zusammen mit dem berechneten relativen Restanteil gegenüber der unbehandelten Pflanze (in Gew.-%) in Tabelle 3 dargestellt. After 21 days, the herbicidal efficacy is assessed. For this, the mass of the remaining above-ground parts of the plant (so-called fresh weight (FW) in grams) is determined. This is shown in Table 3 together with the calculated relative residual to the untreated plant (in wt%).
Tabelle 3: Einfluss der Adjuvante auf die Wirksamkeit von Glyphosat Table 3: Influence of the adjuvant on the efficacy of glyphosate
(AVEFA) (AVEFA)
Beispiel 16: Pestizidzubereitungen, EC-Formulierungen Example 16: Pesticide Preparations, EC Formulations
Verbindung 3 und Verbindung 5 werden auf ihre Eignung als Emulgator in EC-Formulierungen (Emulsifiable Concentrates) getestet. Dazu werden erfindungsgemäße Pestizidzubereitungen mit den Wirkstoffen Malathion und Cypermethrin hergestellt (Tabelle 4).
Tabelle 4: Malathion- und Cypermethrin-EC-Formulierungen Compound 3 and compound 5 are tested for their suitability as emulsifier in EC emulsions (emulsifiable concentrates). For this purpose, pesticide preparations according to the invention are prepared with the active ingredients malathion and cypermethrin (Table 4). Table 4: Malathion and cypermethrin EC formulations
Phenylsulfonat CA (Clariant): Calciumdodecylbenzolsulfonat in iso-Butanol Phenylsulfonate CA (Clariant): calcium dodecylbenzenesulfonate in iso-butanol
(70 %ig) (70%)
Emuslogen® 3510 (Clariant): EO/PO-Blockcopolymer Emuslogen ® 3510 (Clariant): EO / PO block copolymer
Emuisogen® EL 360 (Clariant): Castoröl-Ethoxylat Emuisogen ® EL 360 (Clariant): Castor oil ethoxylate
Xylol: organisches Lösemittel Xylene: organic solvent
Solvesso® 150 (Exxon): organisches Lösemittel Solvesso ® 150 (Exxon): organic solvent
Alle drei Zubereitungen ergeben lagerstabile EC-Formulierungen. Zur Beurteilung der Qualität der Formulierungen werden 5 %ige wässrige Emulsionen in weichem (20 ppm) und hartem (342 ppm) CIPAC-Standard Wasser hergestellt und bei 30 °C nach einem Zeitraum von 2, 4, und 24 Stunden beurteilt. Alle Emulsionen sind über diesen Zeitraum stabil, eine Phasentrennung wird nicht beobachtet.
All three preparations give shelf-stable EC formulations. To assess the quality of the formulations, 5% aqueous emulsions are prepared in soft (20 ppm) and hard (342 ppm) CIPAC standard water and evaluated at 30 ° C for a period of 2, 4, and 24 hours. All emulsions are stable over this period of time, no phase separation is observed.
Claims
1. Pestizidzubereitung enthaltend 1. Pesticide preparation containing
a) ein oder mehrere Pestizide und a) one or more pesticides and
b) ein oder mehrere N-substituierte 2-Pyrrolidon-4-carbonsäure-Derivate. b) one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives.
2. Pestizidzubereitung gemäß Anspruch 1 , dadurch gekennzeichnet, dass das eine oder die mehreren N-substituierten 2-Pyrrolidon-4-carbonsäure-Derivate der Komponente b) ausgewählt sind aus den Verbindungen der Formel (Z) 2. A pesticide preparation according to claim 1, characterized in that the one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives of component b) are selected from the compounds of formula (Z)
worin wherein
R1 C8- bis C3o-Alkyl oder C8- bis C30-Alkenyl ist, R 1 is C 8 - to C 3 o-alkyl or C 8 - to C 30 -alkenyl,
Y OM, -0-[AO]n-X oder NR2R3 ist, Y is OM, -O- [AO] n is -X or NR2R3,
M Wasserstoff, Alkali- oder Erdalkalimetall, Ammonium NH4 + oder substituiertes Ammonium ist, wobei das substituierte Ammonium vorzugsweise ausgewählt ist aus mono-, di- und trisubstituiertem Ammonium und die Substituenten am N-Atom des substituierten Ammoniums wiederum ausgewählt sind aus Alkylgruppen mit 1 bisM is hydrogen, alkali or alkaline earth metal, ammonium NH 4 + or substituted ammonium, wherein the substituted ammonium is preferably selected from mono-, di- and trisubstituted ammonium and the substituents on the N-atom of the substituted ammonium are in turn selected from alkyl groups with 1 to
4 Kohlenstoffatomen und CH2CH2OH, 4 carbon atoms and CH 2 CH 2 OH,
A C2- bis C4-Alkylen oder C6H5-(CH-CH2) ist, AC 2 - to C 4 -alkylene or C 6 H5- (CH-CH 2 ),
n eine Zahl von 0 bis 100 ist, n is a number from 0 to 100,
X C bis C20-Alkyl, Benzyl oder ein substituierter Arylrest ist, wobei der substituierte Arylrest vorzugsweise ausgewählt ist aus Phenyl, das mit 1 bis 3 Substituenten substituiert ist, und diese Substituenten wiederum ausgewählt sind aus Alkylgruppen mit 1 bis 4 Kohlenstoffatomen und Styryl und in dem Fall, dass n ungleich 0 ist, auch Wasserstoff bedeuten kann, X is C 20 alkyl, benzyl or a substituted aryl radical, wherein the substituted aryl radical is preferably selected from phenyl which is substituted with 1 to 3 substituents, and these substituents are in turn selected from alkyl groups having 1 to 4 carbon atoms and styryl and in in the case where n is not 0, it may also be hydrogen,
R2 und R3 unabhängig voneinander Wasserstoff, C bis C2o-Alkyl oder R2 and R3 are independently hydrogen, C to C 2 o-alkyl or
(C2H40)pH sind und P eine Zahl von 1 bis 20 ist. (C 2 H 4 0) p H are and P is a number from 1 to 20.
3. Pestizidzubereitung gemäß Anspruch 1 oder 2, dadurch gekennzeichnet, dass das eine oder die mehreren N-substituierten 2-Pyrrolidon-4-carbonsäure- Derivate der Komponente b) ausgewählt sind aus den Verbindungen der Formel (1) 3. Pesticide preparation according to claim 1 or 2, characterized in that the one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives of component b) are selected from the compounds of formula (1)
R1 C8- bis C30-Alkyl oder C8- bis C3o-Alkenyl ist und R 1 is C 8 - to C 30 -alkyl or C 8 - to C 3 o-alkenyl and
M Wasserstoff, Alkali- oder Erdalkalimetall, Ammonium NH4 + oder substituiertes Ammonium ist, wobei das substituierte Ammonium vorzugsweise ausgewählt ist aus mono-, di- und trisubstituiertem Ammonium und die Substituenten am N-Atom des substituierten Ammoniums wiederum ausgewählt sind aus Alkylgruppen mit 1 bis 4 Kohlenstoffatomen und CH2CH2OH. M is hydrogen, alkali or alkaline earth metal, ammonium NH 4 + or substituted ammonium, wherein the substituted ammonium is preferably selected from mono-, di- and trisubstituted ammonium and the substituents on the N-atom of the substituted ammonium are in turn selected from alkyl groups with 1 to 4 carbon atoms and CH 2 CH 2 OH.
4. Pestizidzubereitung gemäß Anspruch 1 oder 2, dadurch gekennzeichnet, dass das eine oder die mehreren N-substituierten 2-Pyrrolidon-4-carbonsäure- Derivate der Komponente b) ausgewählt sind aus den Verbindungen der Formel (2) 4. A pesticide preparation according to claim 1 or 2, characterized in that the one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives of component b) are selected from the compounds of formula (2)
worin wherein
R1 C8- bis Cßo-Alkyl oder C8- bis C30-Alkenyl ist, R 1 is C 8 - to C ß o-alkyl or C 8 - to C 30 alkenyl,
A C2- bis C4-Alkylen oder C6H5-(CH-CH2) ist, n eine Zahl von 0 bis 100 ist und AC 2 - to C 4 -alkylene or C 6 H 5 - (CH-CH 2 ), n is a number from 0 to 100 and
X C bis C2o-Alkyl, Benzyl oder ein substituierter Arylrest ist, wobei der substituierte Arylrest vorzugsweise ausgewählt ist aus Phenyl, das mit 1 bis 3 Substituenten substituert ist, und diese Substituenten wiederum ausgewählt sind aus Alkylgruppen mit 1 bis 4X is C 2 to C 2 o-alkyl, benzyl or a substituted aryl radical, wherein the substituted aryl radical is preferably selected from phenyl which is substituted with 1 to 3 substituents, and these substituents are in turn selected from alkyl groups having 1 to 4
Kohlenstoffatomen und Styryl und in dem Fall, dass n ungleich 0 ist, auch Wasserstoff bedeuten kann. Carbon atoms and styryl and in the event that n is not 0, may also mean hydrogen.
5. Pestizidzubereitung gemäß Anspruch 1 oder 2, dadurch gekennzeichnet, dass das eine oder die mehreren N-substituierten 2-Pyrrolidon-4-carbonsäure- Derivate der Komponente b) ausgewählt sind aus den Verbindungen der 5. A pesticide preparation according to claim 1 or 2, characterized in that the one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives of component b) are selected from the compounds of
Formel (3) Formula (3)
worin wherein
R1 C8- bis C30-Alkyl oder C8- bis C3o-Alkenyl ist, R 1 is C 8 - to C 30 -alkyl or C 8 - to C 3 o-alkenyl,
R2 und R3 unabhängig voneinander Wasserstoff, C bis C2o-Alkyl oder R2 and R3 independently of one another are hydrogen, C to C20-alkyl or
(C2H40)pH sind und (C 2 H 4 0) p H are and
p eine Zahl von 1 bis 20 ist. p is a number from 1 to 20.
6. Verwendung eines oder mehrerer N-substituierter 2-Pyrrolidon-4- carbonsäure-Derivate als Adjuvant, vorzugsweise in einer Pestizidzubereitung gemäß einem oder mehreren der Ansprüche 1 bis 5. 6. Use of one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives as adjuvant, preferably in a pesticide preparation according to one or more of claims 1 to 5.
7. Verwendung eines oder mehrerer N-substituierter 2-Pyrrolidon-4- carbonsäure-Derivate als Emulgator, vorzugsweise in einer Pestizidzubereitung gemäß einem oder mehreren der Ansprüche 1 bis 5. 7. Use of one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives as emulsifier, preferably in a pesticide preparation according to one or more of claims 1 to 5.
8. Verwendung eines oder mehrerer N-substituierter 2-Pyrrolidon-4- carbonsäure-Derivate als Netzmittel, vorzugsweise in einer Pestizidzubereitung gemäß einem oder mehreren der Ansprüche 1 bis 5. 8. Use of one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives as wetting agents, preferably in a pesticide preparation according to one or more of claims 1 to 5.
9. Verwendung eines oder mehrerer N-substituierter 2-Pyrrolidon-4- carbonsäure-Derivate als Dispergiermittel, vorzugsweise in einer 9. Use of one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives as dispersants, preferably in one
Pestizidzubereitung gemäß einem oder mehreren der Ansprüche 1 bis 5. A pesticide preparation according to one or more of claims 1 to 5.
10. Verwendung eines oder mehrerer N-substituierter 2-Pyrrolidon-4- carbonsäure-Derivate zur Herstellung einer Pestizidzubereitung nach einem oder mehreren der Ansprüche 1 bis 5. 10. Use of one or more N-substituted 2-pyrrolidone-4-carboxylic acid derivatives for the preparation of a pesticide preparation according to one or more of claims 1 to 5.
11. Verwendung einer Pestizidzubereitung nach einem oder mehreren der Ansprüche 1 bis 5 zur Kontrolle und/oder Bekämpfung von Unkraut, 11. Use of a pesticide preparation according to one or more of claims 1 to 5 for the control and / or control of weeds,
Pilzerkrankungen oder Insektenbefall. Fungal diseases or insect infestation.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102009043122 | 2009-09-25 | ||
PCT/EP2010/005737 WO2011035873A1 (en) | 2009-09-25 | 2010-09-18 | Pesticide preparations containing derivatives of pyrrolidone-4-carboxylic acid |
Publications (1)
Publication Number | Publication Date |
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EP2480071A1 true EP2480071A1 (en) | 2012-08-01 |
Family
ID=43301780
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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EP10755112A Withdrawn EP2480071A1 (en) | 2009-09-25 | 2010-09-18 | Pesticide preparations containing derivatives of pyrrolidone-4-carboxylic acid |
Country Status (6)
Country | Link |
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US (1) | US20120264611A1 (en) |
EP (1) | EP2480071A1 (en) |
CN (1) | CN102595883A (en) |
AU (1) | AU2010297634A1 (en) |
BR (1) | BR112012006569A2 (en) |
WO (1) | WO2011035873A1 (en) |
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DE102010046680A1 (en) | 2010-09-16 | 2012-03-22 | Clariant International Limited | Use of N-substituted 2-pyrrolidone-4-carboxylic esters as solvents |
DE102010046679A1 (en) | 2010-09-16 | 2012-03-22 | Clariant International Ltd. | Pesticidal preparations containing N-substituted 2-pyrrolidone-4-carboxylic acid esters |
DE102012017739A1 (en) | 2012-09-07 | 2014-03-13 | Clariant International Ltd. | Process for the preparation of N-substituted Pyrrolidoncarbonsäureestern |
CN112430156A (en) * | 2020-12-04 | 2021-03-02 | 中诚国联(河南)生物科技有限公司 | Preparation method and application of high-tower pesticide-fertilizer granules for preventing and treating piercing-sucking pests |
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US2757125A (en) * | 1952-05-16 | 1956-07-31 | Colgate Palmolive Co | N-higher alkyl-4-carboxy-2-pyrrolidones and compositions therewith |
US5283229A (en) * | 1989-12-11 | 1994-02-01 | Isp Investments Inc. | Delivery system for agricultural chemicals |
US5985798A (en) * | 1998-06-04 | 1999-11-16 | Hampshire Chemical Corp. | N-acyl sarcosinates as glyphosate adjuvants |
DE50105381D1 (en) * | 2000-09-13 | 2005-03-24 | Basf Ag | OIL SUSPENSION CONCENTRATES BASED ON A CYCLOHEXENONE OXIMETHER LITHIUM SALT AND THEIR USE AS PLANT PROTECTION AGENTS |
-
2010
- 2010-09-18 WO PCT/EP2010/005737 patent/WO2011035873A1/en active Application Filing
- 2010-09-18 BR BR112012006569A patent/BR112012006569A2/en not_active IP Right Cessation
- 2010-09-18 US US13/497,975 patent/US20120264611A1/en not_active Abandoned
- 2010-09-18 CN CN2010800427242A patent/CN102595883A/en active Pending
- 2010-09-18 AU AU2010297634A patent/AU2010297634A1/en not_active Abandoned
- 2010-09-18 EP EP10755112A patent/EP2480071A1/en not_active Withdrawn
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Publication number | Publication date |
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US20120264611A1 (en) | 2012-10-18 |
WO2011035873A1 (en) | 2011-03-31 |
CN102595883A (en) | 2012-07-18 |
BR112012006569A2 (en) | 2015-09-08 |
AU2010297634A1 (en) | 2012-05-03 |
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