IL86996A - Methods for the protection of crops against herbicides which are 2- (2-benzoyl) -benzoyl (1,3-cyclohexanedione) by antidotes and preparations containing them - Google Patents
Methods for the protection of crops against herbicides which are 2- (2-benzoyl) -benzoyl (1,3-cyclohexanedione) by antidotes and preparations containing themInfo
- Publication number
- IL86996A IL86996A IL8699688A IL8699688A IL86996A IL 86996 A IL86996 A IL 86996A IL 8699688 A IL8699688 A IL 8699688A IL 8699688 A IL8699688 A IL 8699688A IL 86996 A IL86996 A IL 86996A
- Authority
- IL
- Israel
- Prior art keywords
- alkyl
- hydrogen
- herbicide
- halogen
- antidote
- Prior art date
Links
- 239000000729 antidote Substances 0.000 title claims description 95
- 239000004009 herbicide Substances 0.000 title claims description 89
- 239000000203 mixture Substances 0.000 title claims description 61
- 238000000034 method Methods 0.000 title claims description 27
- -1 2-(2-substituted benzoyl)-1,3-cyclohexanedione Chemical class 0.000 title description 28
- 229940075522 antidotes Drugs 0.000 title description 22
- 150000001875 compounds Chemical class 0.000 claims description 97
- 230000002363 herbicidal effect Effects 0.000 claims description 93
- 239000001257 hydrogen Substances 0.000 claims description 87
- 229910052739 hydrogen Inorganic materials 0.000 claims description 87
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 71
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 70
- 238000011282 treatment Methods 0.000 claims description 70
- 125000000217 alkyl group Chemical group 0.000 claims description 57
- 229910052736 halogen Inorganic materials 0.000 claims description 48
- 150000002367 halogens Chemical class 0.000 claims description 48
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 46
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 28
- 125000002947 alkylene group Chemical group 0.000 claims description 26
- 230000006378 damage Effects 0.000 claims description 24
- 239000000460 chlorine Substances 0.000 claims description 23
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 229910052801 chlorine Inorganic materials 0.000 claims description 21
- 239000002689 soil Substances 0.000 claims description 21
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 20
- 208000027418 Wounds and injury Diseases 0.000 claims description 19
- 208000014674 injury Diseases 0.000 claims description 19
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 18
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 14
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 14
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 13
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
- 229910052794 bromium Chemical group 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 150000001408 amides Chemical class 0.000 claims description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- 125000001188 haloalkyl group Chemical group 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 6
- 239000011593 sulfur Chemical group 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 231100001184 nonphytotoxic Toxicity 0.000 claims description 5
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 claims description 4
- 238000010348 incorporation Methods 0.000 claims description 4
- 125000004983 dialkoxyalkyl group Chemical group 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 229960005215 dichloroacetic acid Drugs 0.000 claims description 2
- 238000004381 surface treatment Methods 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 41
- 240000008042 Zea mays Species 0.000 description 38
- 241000196324 Embryophyta Species 0.000 description 34
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 34
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 34
- 235000005822 corn Nutrition 0.000 description 34
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 33
- 208000037824 growth disorder Diseases 0.000 description 19
- 238000009472 formulation Methods 0.000 description 17
- 239000008187 granular material Substances 0.000 description 15
- 238000012360 testing method Methods 0.000 description 14
- 235000002248 Setaria viridis Nutrition 0.000 description 12
- 239000013543 active substance Substances 0.000 description 12
- 208000006278 hypochromic anemia Diseases 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 9
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 9
- 239000011737 fluorine Substances 0.000 description 9
- 229910052731 fluorine Inorganic materials 0.000 description 9
- 125000000623 heterocyclic group Chemical group 0.000 description 9
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 9
- 235000010086 Setaria viridis var. viridis Nutrition 0.000 description 8
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 8
- 238000004061 bleaching Methods 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 239000004094 surface-active agent Substances 0.000 description 8
- 239000005995 Aluminium silicate Substances 0.000 description 7
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 7
- 235000012211 aluminium silicate Nutrition 0.000 description 7
- 239000000969 carrier Substances 0.000 description 7
- 244000304962 green bristle grass Species 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 240000006394 Sorghum bicolor Species 0.000 description 6
- 125000004414 alkyl thio group Chemical group 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 5
- 244000237956 Amaranthus retroflexus Species 0.000 description 5
- 244000058871 Echinochloa crus-galli Species 0.000 description 5
- 240000003461 Setaria viridis Species 0.000 description 5
- 230000002411 adverse Effects 0.000 description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 5
- HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical group O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000003995 emulsifying agent Substances 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
- 235000017016 Setaria faberi Nutrition 0.000 description 4
- 241001355178 Setaria faberi Species 0.000 description 4
- 240000002439 Sorghum halepense Species 0.000 description 4
- 230000009286 beneficial effect Effects 0.000 description 4
- 235000019993 champagne Nutrition 0.000 description 4
- 239000004927 clay Substances 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- OILAIQUEIWYQPH-UHFFFAOYSA-N cyclohexane-1,2-dione Chemical compound O=C1CCCCC1=O OILAIQUEIWYQPH-UHFFFAOYSA-N 0.000 description 4
- 239000004495 emulsifiable concentrate Substances 0.000 description 4
- 239000003815 herbicide antidote Substances 0.000 description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 description 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 241000894007 species Species 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 125000004001 thioalkyl group Chemical group 0.000 description 4
- PJRBNYFEOFABLY-UHFFFAOYSA-N 2,2-dichloro-1-(2,2-dimethyl-5-propyl-1,3-oxazolidin-3-yl)ethanone Chemical compound CCCC1CN(C(=O)C(Cl)Cl)C(C)(C)O1 PJRBNYFEOFABLY-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- MDBGGTQNNUOQRC-UHFFFAOYSA-N Allidochlor Chemical compound ClCC(=O)N(CC=C)CC=C MDBGGTQNNUOQRC-UHFFFAOYSA-N 0.000 description 3
- JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 235000015225 Panicum colonum Nutrition 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 235000007244 Zea mays Nutrition 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 125000002837 carbocyclic group Chemical group 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- WCGGWVOVFQNRRS-UHFFFAOYSA-N dichloroacetamide Chemical compound NC(=O)C(Cl)Cl WCGGWVOVFQNRRS-UHFFFAOYSA-N 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 150000002191 fatty alcohols Chemical class 0.000 description 3
- 239000003337 fertilizer Substances 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000003094 microcapsule Substances 0.000 description 3
- 238000010899 nucleation Methods 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 3
- 230000008635 plant growth 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
- 150000003839 salts Chemical class 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 238000003419 tautomerization reaction Methods 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 description 2
- KEAUDBRYQMGJMR-UHFFFAOYSA-N 2,2-dichloro-1-(2,2,5-trimethyl-1,3-thiazolidin-3-yl)ethanone Chemical compound CC1CN(C(=O)C(Cl)Cl)C(C)(C)S1 KEAUDBRYQMGJMR-UHFFFAOYSA-N 0.000 description 2
- RFEBDZANCVHDLP-UHFFFAOYSA-N 3-[(4-cyanophenyl)methylamino]-6-(trifluoromethyl)quinoxaline-2-carboxylic acid Chemical compound OC(=O)C1=NC2=CC=C(C(F)(F)F)C=C2N=C1NCC1=CC=C(C#N)C=C1 RFEBDZANCVHDLP-UHFFFAOYSA-N 0.000 description 2
- 240000006995 Abutilon theophrasti Species 0.000 description 2
- 240000001592 Amaranthus caudatus Species 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
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- 244000277285 Cassia obtusifolia Species 0.000 description 2
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- 244000037364 Cinnamomum aromaticum Species 0.000 description 2
- 235000014489 Cinnamomum aromaticum Nutrition 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- 240000005979 Hordeum vulgare Species 0.000 description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 description 2
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- GRSMWKLPSNHDHA-UHFFFAOYSA-N Naphthalic anhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=CC3=C1 GRSMWKLPSNHDHA-UHFFFAOYSA-N 0.000 description 2
- 235000011999 Panicum crusgalli Nutrition 0.000 description 2
- 231100000674 Phytotoxicity Toxicity 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 229920001213 Polysorbate 20 Polymers 0.000 description 2
- YNQSILKYZQZHFJ-UHFFFAOYSA-N R-29148 Chemical compound CC1CN(C(=O)C(Cl)Cl)C(C)(C)O1 YNQSILKYZQZHFJ-UHFFFAOYSA-N 0.000 description 2
- 235000007230 Sorghum bicolor Nutrition 0.000 description 2
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- 125000001246 bromo group Chemical group Br* 0.000 description 2
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- 238000013461 design Methods 0.000 description 2
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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- 125000001841 imino group Chemical group [H]N=* 0.000 description 2
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- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
- 230000017074 necrotic cell death Effects 0.000 description 2
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- WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical compound CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 1
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 1
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 description 1
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 description 1
- IJVLVRYLIMQVDD-UHFFFAOYSA-N 1,3-thiazole-2-carboxylic acid Chemical class OC(=O)C1=NC=CS1 IJVLVRYLIMQVDD-UHFFFAOYSA-N 0.000 description 1
- XNIQTXHGQXXNSX-UHFFFAOYSA-N 1-(5-butyl-2,2-dimethyl-1,3-oxazolidin-3-yl)-2,2-dichloroethanone Chemical compound CCCCC1CN(C(=O)C(Cl)Cl)C(C)(C)O1 XNIQTXHGQXXNSX-UHFFFAOYSA-N 0.000 description 1
- QVHNPERSEFABEH-UHFFFAOYSA-N 2,2-dibromopropanoic acid Chemical compound CC(Br)(Br)C(O)=O QVHNPERSEFABEH-UHFFFAOYSA-N 0.000 description 1
- RLJHUAABUCHYNU-UHFFFAOYSA-N 2,2-dichloro-1-(1,3-oxazolidin-3-yl)ethanone Chemical compound ClC(Cl)C(=O)N1CCOC1 RLJHUAABUCHYNU-UHFFFAOYSA-N 0.000 description 1
- NFEFNQWUWWOFLG-UHFFFAOYSA-N 2,2-dichloro-1-(2,2,4,5-tetramethyl-1,3-oxazolidin-3-yl)ethanone Chemical compound CC1OC(C)(C)N(C(=O)C(Cl)Cl)C1C NFEFNQWUWWOFLG-UHFFFAOYSA-N 0.000 description 1
- CZSMRBVLOVGPLX-UHFFFAOYSA-N 2,2-dichloro-1-(2,2,4-trimethyl-1,3-oxazolidin-3-yl)ethanone Chemical compound CC1COC(C)(C)N1C(=O)C(Cl)Cl CZSMRBVLOVGPLX-UHFFFAOYSA-N 0.000 description 1
- OGZJCYMZCPCYTG-UHFFFAOYSA-N 2,2-dichloro-1-(2,2,5,5-tetramethyl-1,3-oxazolidin-3-yl)ethanone Chemical compound CC1(C)CN(C(=O)C(Cl)Cl)C(C)(C)O1 OGZJCYMZCPCYTG-UHFFFAOYSA-N 0.000 description 1
- FOMHMPJALXOZGZ-UHFFFAOYSA-N 2,2-dichloro-1-(2,2-dimethyl-1,3-oxazolidin-3-yl)ethanone Chemical compound CC1(C)OCCN1C(=O)C(Cl)Cl FOMHMPJALXOZGZ-UHFFFAOYSA-N 0.000 description 1
- LWIIQWXXUZNQQV-UHFFFAOYSA-N 2,2-dichloro-1-(2,2-dimethyl-1,3-thiazolidin-3-yl)ethanone Chemical compound CC1(C)SCCN1C(=O)C(Cl)Cl LWIIQWXXUZNQQV-UHFFFAOYSA-N 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
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- DVQHRBFGRZHMSR-UHFFFAOYSA-N sodium methyl 2,2-dimethyl-4,6-dioxo-5-(N-prop-2-enoxy-C-propylcarbonimidoyl)cyclohexane-1-carboxylate Chemical compound [Na+].C=CCON=C(CCC)[C-]1C(=O)CC(C)(C)C(C(=O)OC)C1=O DVQHRBFGRZHMSR-UHFFFAOYSA-N 0.000 description 1
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- SRAWNDFHGTVUNZ-UHFFFAOYSA-M sodium;3,6-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC(CCCC)=CC2=CC(CCCC)=CC=C21 SRAWNDFHGTVUNZ-UHFFFAOYSA-M 0.000 description 1
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- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
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- 239000000375 suspending agent Substances 0.000 description 1
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- 235000012976 tarts Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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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
- A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
-
- 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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
- A01N43/18—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with sulfur as the ring hetero atom
-
- 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
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing keto or thioketo groups as part of a ring, e.g. cyclohexanone, quinone; Derivatives thereof, e.g. ketals
-
- 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
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen
- A01N35/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen containing a carbon-to-nitrogen double bond
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing within the same carbon skeleton a carboxylic group or a thio analogue, or a derivative thereof, and a carbon atom having only two bonds to hetero atoms with at the most one bond to halogen, e.g. keto-carboxylic acids
-
- 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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/10—Sulfones; Sulfoxides
-
- 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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
- A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
-
- 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
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7001587A | 1987-07-06 | 1987-07-06 | |
| US07/208,269 US4938796A (en) | 1987-07-06 | 1988-06-22 | Herbicidal compositions of acylated 1,3-dicarbonyl herbicides and antidotes therefor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL86996A0 IL86996A0 (en) | 1988-12-30 |
| IL86996A true IL86996A (en) | 1994-04-12 |
Family
ID=26750670
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL8699688A IL86996A (en) | 1987-07-06 | 1988-07-05 | Methods for the protection of crops against herbicides which are 2- (2-benzoyl) -benzoyl (1,3-cyclohexanedione) by antidotes and preparations containing them |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US4938796A (cs) |
| EP (1) | EP0298680B1 (cs) |
| JP (1) | JP2896146B2 (cs) |
| KR (1) | KR960016186B1 (cs) |
| CN (1) | CN1031916C (cs) |
| AR (1) | AR245866A1 (cs) |
| AT (1) | ATE94339T1 (cs) |
| AU (1) | AU604336B2 (cs) |
| BG (1) | BG60301B2 (cs) |
| BR (1) | BR8803350A (cs) |
| CA (1) | CA1337158C (cs) |
| CZ (1) | CZ286115B6 (cs) |
| DE (1) | DE3884076T2 (cs) |
| DK (1) | DK376488A (cs) |
| EG (1) | EG18668A (cs) |
| ES (1) | ES2059521T3 (cs) |
| HU (1) | HU205890B (cs) |
| IE (1) | IE61677B1 (cs) |
| IL (1) | IL86996A (cs) |
| MX (1) | MX168198B (cs) |
| MY (1) | MY103739A (cs) |
| NZ (1) | NZ225297A (cs) |
| PH (1) | PH25483A (cs) |
| PL (1) | PL158086B1 (cs) |
| PT (1) | PT87912B (cs) |
| SK (1) | SK488288A3 (cs) |
| TR (1) | TR24112A (cs) |
| ZW (1) | ZW8988A1 (cs) |
Families Citing this family (29)
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|---|---|---|---|---|
| US5256625A (en) * | 1987-08-13 | 1993-10-26 | Monsanto Company | Safening imidazolinone herbicides |
| DE59010829D1 (de) * | 1989-10-18 | 1998-07-16 | Hoechst Schering Agrevo Gmbh | Herbizide wirkstoffkombinationen |
| AU7463791A (en) * | 1990-03-14 | 1991-10-10 | James L. Ahle | Herbicidal compositions of aroylated 1,3-dicarbonyl or 1,3,5-tricarbonyl cyclohexane herbicides and an antidote system therefor |
| WO1991013547A1 (en) * | 1990-03-14 | 1991-09-19 | Ahle James L | Herbicidal compositions of aroylated 1,3-dicarbonyl or 1,3,5-tricarbonyl cyclohexane herbicides and two-part antidote system therefor |
| ES2108121T3 (es) * | 1991-05-01 | 1997-12-16 | Zeneca Ltd | Composiciones herbicidas a base de ciclohexanodionas substituidas y fertilizantes nitrogenados y metodo. |
| DE59209757D1 (de) * | 1991-12-31 | 1999-11-18 | Hoechst Ag | Kombinationen aus Herbiziden und pflanzenschützenden Stoffen |
| GB9313210D0 (en) * | 1993-06-25 | 1993-08-11 | Sandoz Ltd | Novel combinations |
| US5627131A (en) * | 1995-01-09 | 1997-05-06 | Zeneca Limited | Herbicidal compositions of 4-benzoylisoxazole and antidotes therefor |
| AR005600A1 (es) * | 1996-02-02 | 1999-06-23 | Syngenta Ltd | Composiciones herbicidas quimicamente estables de quelatos metalicos de dionas herbicidas, y proceso para su produccion |
| US5668089A (en) * | 1996-04-08 | 1997-09-16 | Zeneca Limited | Selective corn herbicide |
| AUPO190596A0 (en) | 1996-08-26 | 1996-09-19 | Alchemia Pty Ltd | Oligosaccharide synthesis |
| DE19700019A1 (de) | 1997-01-03 | 1998-07-09 | Basf Ag | Substituierte 2-Benzoyl-cyclohexan-1,3-dione |
| DE19700097A1 (de) | 1997-01-03 | 1998-07-09 | Basf Ag | 3-Aminocarbonyl/3-Aminothiocarbonyl-substituierte 2-Benzoyl-cyclohexan-1,3-dione |
| US5912207A (en) * | 1997-01-31 | 1999-06-15 | Zeneca Limited | Stable herbicidal compositions containing metal chelates of herbicidal dione compounds |
| WO1998050377A1 (de) * | 1997-05-07 | 1998-11-12 | Basf Aktiengesellschaft | Substituierte 2-benzoyl-cyclohexan-1,3-dione |
| CA2298574A1 (en) | 1997-08-07 | 1999-02-18 | Basf Aktiengesellschaft | 2-benzoyl-cyclohexane-1,3-diones |
| WO1999010327A1 (de) | 1997-08-07 | 1999-03-04 | Basf Aktiengesellschaft | 2-benzoyl-cyclohexan-1,3-dione als herbizide |
| AUPO937597A0 (en) * | 1997-09-24 | 1997-10-16 | Alchemia Pty Ltd | Protecting and linking groups for organic synthesis |
| JPH11279157A (ja) * | 1998-03-27 | 1999-10-12 | Hoechst Marion Roussel Kk | バルビツール酸誘導体およびそれらからなる骨・軟骨疾患予防・治療薬 |
| DE19827855A1 (de) | 1998-06-23 | 1999-12-30 | Hoechst Schering Agrevo Gmbh | Kombinationen aus Herbiziden und Safenern |
| AU4900699A (en) * | 1998-06-26 | 2000-01-17 | Novartis Pharma Ag | Herbicidal composition |
| DE19853827A1 (de) * | 1998-11-21 | 2000-05-25 | Aventis Cropscience Gmbh | Kombinationen aus Herbiziden und Safenern |
| US6541422B2 (en) | 1999-05-28 | 2003-04-01 | Syngenta Limited | Method for improving the selectivity of 1,3-cyclohexanedione herbicide |
| CA2383716C (en) | 1999-09-08 | 2011-11-01 | Aventis Cropscience Uk Limited | Methods for reducing the phytotoxicity of herbicides using pre-treatment with antidotes |
| ES2214286T3 (es) * | 2000-06-13 | 2004-09-16 | Syngenta Limited | Metodo para mejorar la selectividad de 1,3-ciclohexanodionas herbicidas. |
| GB0213638D0 (en) * | 2002-06-13 | 2002-07-24 | Syngenta Ltd | Composition |
| FR2874522B1 (fr) * | 2004-08-31 | 2006-11-10 | Epb Sa | Tete a aleser |
| US7303440B2 (en) * | 2005-10-03 | 2007-12-04 | Stull Michael F | Universal battery charger/power source adapter |
| CN110372523B (zh) * | 2019-08-13 | 2021-06-22 | 中国农业科学院棉花研究所 | 一种含二氯乙酸双羟基季铵盐除草剂、其制备方法及应用 |
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-
1988
- 1988-06-22 US US07/208,269 patent/US4938796A/en not_active Expired - Lifetime
- 1988-06-30 MY MYPI88000724A patent/MY103739A/en unknown
- 1988-07-04 AU AU18670/88A patent/AU604336B2/en not_active Expired
- 1988-07-04 EP EP88306071A patent/EP0298680B1/en not_active Expired - Lifetime
- 1988-07-04 DE DE88306071T patent/DE3884076T2/de not_active Expired - Lifetime
- 1988-07-04 AT AT88306071T patent/ATE94339T1/de not_active IP Right Cessation
- 1988-07-04 PH PH37172A patent/PH25483A/en unknown
- 1988-07-04 ES ES88306071T patent/ES2059521T3/es not_active Expired - Lifetime
- 1988-07-05 CZ CS19884882A patent/CZ286115B6/cs unknown
- 1988-07-05 PT PT87912A patent/PT87912B/pt not_active IP Right Cessation
- 1988-07-05 IL IL8699688A patent/IL86996A/en not_active IP Right Cessation
- 1988-07-05 AR AR88311326A patent/AR245866A1/es active
- 1988-07-05 IE IE204488A patent/IE61677B1/en not_active IP Right Cessation
- 1988-07-05 CA CA000571114A patent/CA1337158C/en not_active Expired - Lifetime
- 1988-07-05 NZ NZ225297A patent/NZ225297A/xx unknown
- 1988-07-05 MX MX012160A patent/MX168198B/es unknown
- 1988-07-05 SK SK4882-88A patent/SK488288A3/sk unknown
- 1988-07-05 HU HU883528A patent/HU205890B/hu unknown
- 1988-07-06 BR BR8803350A patent/BR8803350A/pt not_active IP Right Cessation
- 1988-07-06 DK DK376488A patent/DK376488A/da not_active Application Discontinuation
- 1988-07-06 ZW ZW89/88A patent/ZW8988A1/xx unknown
- 1988-07-06 PL PL1988273557A patent/PL158086B1/pl unknown
- 1988-07-06 CN CN88104156A patent/CN1031916C/zh not_active Expired - Lifetime
- 1988-07-06 BG BG084794A patent/BG60301B2/bg unknown
- 1988-07-06 EG EG37488A patent/EG18668A/xx active
- 1988-07-06 TR TR88/0525A patent/TR24112A/xx unknown
- 1988-07-06 KR KR1019880008359A patent/KR960016186B1/ko not_active Expired - Lifetime
- 1988-07-06 JP JP63167001A patent/JP2896146B2/ja not_active Expired - Lifetime
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| KB | Patent renewed | ||
| HP | Change in proprietorship | ||
| KB | Patent renewed | ||
| HC | Change of name of proprietor(s) | ||
| EXP | Patent expired |