CS253728B2 - Agent for the protection of culture plants and process for preparing active compounds - Google Patents

Agent for the protection of culture plants and process for preparing active compounds Download PDF

Info

Publication number: CS253728B2
Authority: CS; Czechoslovakia
Prior art keywords: formula; group; carbon atoms; alkyl; derivative
Prior art date: 1984-05-28

Application number

CS853823A

Other languages

Czech (cs)

English (en)

Inventor

Henry Martin

Original Assignee

Ciba Geigy Ag

Priority date (The priority date 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 date listed.)

1984-05-28

Filing date

1985-05-28

Publication date

1987-12-17

1985-05-28 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1987-12-17 Publication of CS253728B2 publication Critical patent/CS253728B2/cs

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 46
238000004519 manufacturing process Methods 0.000 title description 7
239000000203 mixture Substances 0.000 claims abstract description 55
230000002363 herbicidal effect Effects 0.000 claims abstract description 39
239000004480 active ingredient Substances 0.000 claims abstract description 23
125000000217 alkyl group Chemical group 0.000 claims abstract description 22
125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
239000001257 hydrogen Substances 0.000 claims abstract description 6
229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
-1 1,3-dioxolan-2-yl Chemical group 0.000 claims description 55
125000004432 carbon atom Chemical group C* 0.000 claims description 28
238000000034 method Methods 0.000 claims description 19
239000013543 active substance Substances 0.000 claims description 17
239000002253 acid Substances 0.000 claims description 14
239000005557 antagonist Substances 0.000 claims description 11
238000002360 preparation method Methods 0.000 claims description 11
229910052799 carbon Inorganic materials 0.000 claims description 10
239000011230 binding agent Substances 0.000 claims description 8
125000005843 halogen group Chemical group 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
239000011541 reaction mixture Substances 0.000 claims description 8
229910052801 chlorine Inorganic materials 0.000 claims description 6
125000004430 oxygen atom Chemical group O* 0.000 claims description 5
125000001424 substituent group Chemical group 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
125000002947 alkylene group Chemical group 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
238000009835 boiling Methods 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
125000004434 sulfur atom Chemical group 0.000 claims description 2
239000013078 crystal Substances 0.000 claims 2
239000000546 pharmaceutical excipient Substances 0.000 claims 2
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
150000001266 acyl halides Chemical class 0.000 claims 1
229940121375 antifungal agent Drugs 0.000 claims 1
239000003429 antifungal agent Substances 0.000 claims 1
239000003963 antioxidant agent Substances 0.000 claims 1
241000196324 Embryophyta Species 0.000 abstract description 21
240000008042 Zea mays Species 0.000 abstract description 13
235000002017 Zea mays subsp mays Nutrition 0.000 abstract description 10
244000062793 Sorghum vulgare Species 0.000 abstract description 8
235000019713 millet Nutrition 0.000 abstract description 8
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract description 7
235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 abstract description 7
235000009973 maize Nutrition 0.000 abstract description 7
230000000885 phytotoxic effect Effects 0.000 abstract description 7
235000013339 cereals Nutrition 0.000 abstract description 5
238000012360 testing method Methods 0.000 abstract description 5
240000007594 Oryza sativa Species 0.000 abstract description 4
235000007164 Oryza sativa Nutrition 0.000 abstract description 4
229910052736 halogen Inorganic materials 0.000 abstract description 4
150000002367 halogens Chemical class 0.000 abstract description 4
235000009566 rice Nutrition 0.000 abstract description 4
125000004414 alkyl thio group Chemical group 0.000 abstract description 3
125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract description 2
125000004093 cyano group Chemical group *C#N 0.000 abstract description 2
229920006395 saturated elastomer Polymers 0.000 abstract description 2
VONWPEXRCLHKRJ-UHFFFAOYSA-N 2-chloro-n-phenylacetamide Chemical class ClCC(=O)NC1=CC=CC=C1 VONWPEXRCLHKRJ-UHFFFAOYSA-N 0.000 abstract 2
239000004215 Carbon black (E152) Substances 0.000 abstract 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
150000002431 hydrogen Chemical class 0.000 abstract 2
229910052760 oxygen Inorganic materials 0.000 abstract 2
239000001301 oxygen Substances 0.000 abstract 2
239000011593 sulfur Chemical group 0.000 abstract 2
125000006193 alkinyl group Chemical group 0.000 abstract 1
125000005119 alkyl cycloalkyl group Chemical group 0.000 abstract 1
125000004122 cyclic group Chemical group 0.000 abstract 1
125000000753 cycloalkyl group Chemical group 0.000 abstract 1
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 abstract 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 75
239000004009 herbicide Substances 0.000 description 52
235000019441 ethanol Nutrition 0.000 description 43
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 39
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
239000003921 oil Substances 0.000 description 25
235000019198 oils Nutrition 0.000 description 25
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
238000006243 chemical reaction Methods 0.000 description 23
239000000729 antidote Substances 0.000 description 22
230000001681 protective effect Effects 0.000 description 22
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 20
239000000243 solution Substances 0.000 description 17
150000001412 amines Chemical class 0.000 description 15
239000002689 soil Substances 0.000 description 15
239000004094 surface-active agent Substances 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
230000000694 effects Effects 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
244000038559 crop plants Species 0.000 description 9
239000007787 solid Substances 0.000 description 9
WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 description 8
239000000839 emulsion Substances 0.000 description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
239000000126 substance Substances 0.000 description 8
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
238000002474 experimental method Methods 0.000 description 7
239000008187 granular material Substances 0.000 description 7
239000000843 powder Substances 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
239000002585 base Substances 0.000 description 6
239000000460 chlorine Substances 0.000 description 6
238000001816 cooling Methods 0.000 description 6
235000014113 dietary fatty acids Nutrition 0.000 description 6
239000000194 fatty acid Substances 0.000 description 6
229930195729 fatty acid Natural products 0.000 description 6
229910052708 sodium Inorganic materials 0.000 description 6
239000011734 sodium Substances 0.000 description 6
239000007858 starting material Substances 0.000 description 6
125000002774 3,4-dimethoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 5
239000005995 Aluminium silicate Substances 0.000 description 5
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
235000012211 aluminium silicate Nutrition 0.000 description 5
229940075522 antidotes Drugs 0.000 description 5
235000019439 ethyl acetate Nutrition 0.000 description 5
229940117927 ethylene oxide Drugs 0.000 description 5
238000005984 hydrogenation reaction Methods 0.000 description 5
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 5
239000002904 solvent Substances 0.000 description 5
238000009331 sowing Methods 0.000 description 5
238000003860 storage Methods 0.000 description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
WTFNSXYULBQCQV-UHFFFAOYSA-N $l^{1}-oxidanyloxymethane Chemical compound CO[O] WTFNSXYULBQCQV-UHFFFAOYSA-N 0.000 description 4
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
239000000654 additive Substances 0.000 description 4
229910052783 alkali metal Inorganic materials 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
239000012141 concentrate Substances 0.000 description 4
150000002170 ethers Chemical class 0.000 description 4
230000009931 harmful effect Effects 0.000 description 4
239000003701 inert diluent Substances 0.000 description 4
239000012442 inert solvent Substances 0.000 description 4
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 4
229910052757 nitrogen Inorganic materials 0.000 description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
244000068988 Glycine max Species 0.000 description 3
235000010469 Glycine max Nutrition 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
150000001340 alkali metals Chemical class 0.000 description 3
229910052784 alkaline earth metal Inorganic materials 0.000 description 3
239000000969 carrier Substances 0.000 description 3
230000003197 catalytic effect Effects 0.000 description 3
239000004927 clay Substances 0.000 description 3
238000009833 condensation Methods 0.000 description 3
230000005494 condensation Effects 0.000 description 3
235000005822 corn Nutrition 0.000 description 3
JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
150000004665 fatty acids Chemical class 0.000 description 3
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
239000007788 liquid Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000002736 nonionic surfactant Substances 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
229920000151 polyglycol Polymers 0.000 description 3
239000010695 polyglycol Substances 0.000 description 3
229920001451 polypropylene glycol Polymers 0.000 description 3
150000003335 secondary amines Chemical class 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000004546 suspension concentrate Substances 0.000 description 3
HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 3
125000006656 (C2-C4) alkenyl group Chemical group 0.000 description 2
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
RQJDUEKERVZLLU-UHFFFAOYSA-N 4-Hydroxybenzylamine Chemical compound NCC1=CC=C(O)C=C1 RQJDUEKERVZLLU-UHFFFAOYSA-N 0.000 description 2
HKPHPIREJKHECO-UHFFFAOYSA-N Amichlor Natural products CCCCOCN(C(=O)CCl)C1=C(CC)C=CC=C1CC HKPHPIREJKHECO-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
KLYCPFXDDDMZNQ-UHFFFAOYSA-N Benzyne Chemical compound C1=CC#CC=C1 KLYCPFXDDDMZNQ-UHFFFAOYSA-N 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
240000005979 Hordeum vulgare Species 0.000 description 2
235000007340 Hordeum vulgare Nutrition 0.000 description 2
235000019738 Limestone Nutrition 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
244000297179 Syringa vulgaris Species 0.000 description 2
235000004338 Syringa vulgaris Nutrition 0.000 description 2
239000003377 acid catalyst Substances 0.000 description 2
230000000996 additive effect Effects 0.000 description 2
239000003905 agrochemical Substances 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
150000001342 alkaline earth metals Chemical class 0.000 description 2
125000004183 alkoxy alkyl group Chemical group 0.000 description 2
150000008055 alkyl aryl sulfonates Chemical class 0.000 description 2
125000006350 alkyl thio alkyl group Chemical group 0.000 description 2
150000001413 amino acids Chemical group 0.000 description 2
150000003863 ammonium salts Chemical class 0.000 description 2
239000003945 anionic surfactant Substances 0.000 description 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
239000012736 aqueous medium Substances 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 2
125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
150000003939 benzylamines Chemical class 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Chemical group 0.000 description 2
239000011575 calcium Substances 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
235000014633 carbohydrates Nutrition 0.000 description 2
150000001720 carbohydrates Chemical class 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
239000001569 carbon dioxide Substances 0.000 description 2
229910002092 carbon dioxide Inorganic materials 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000003240 coconut oil Substances 0.000 description 2
235000019864 coconut oil Nutrition 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
101150047356 dec-1 gene Proteins 0.000 description 2
DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical group OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
239000000428 dust Substances 0.000 description 2
238000010410 dusting Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
235000019197 fats Nutrition 0.000 description 2
150000002191 fatty alcohols Chemical class 0.000 description 2
125000001188 haloalkyl group Chemical group 0.000 description 2
239000005457 ice water Substances 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
229920005610 lignin Polymers 0.000 description 2
239000006028 limestone Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
239000002609 medium Substances 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
XMYQHJDBLRZMLW-UHFFFAOYSA-N methanolamine Chemical compound NCO XMYQHJDBLRZMLW-UHFFFAOYSA-N 0.000 description 2
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
238000002156 mixing Methods 0.000 description 2
SYGACMXWLAQEPN-UHFFFAOYSA-N n-[(4-methoxyphenyl)methyl]ethanamine Chemical compound CCNCC1=CC=C(OC)C=C1 SYGACMXWLAQEPN-UHFFFAOYSA-N 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
239000012071 phase Substances 0.000 description 2
150000002989 phenols Chemical class 0.000 description 2
231100000208 phytotoxic Toxicity 0.000 description 2
238000005554 pickling Methods 0.000 description 2
239000004033 plastic Substances 0.000 description 2
229920003023 plastic Polymers 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
239000011814 protection agent Substances 0.000 description 2
238000006722 reduction reaction Methods 0.000 description 2
239000000344 soap Substances 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
241000894007 species Species 0.000 description 2
238000006277 sulfonation reaction Methods 0.000 description 2
125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 2
150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
239000000725 suspension Substances 0.000 description 2
125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 2
239000004563 wettable powder Substances 0.000 description 2
239000008096 xylene Substances 0.000 description 2
150000003738 xylenes Chemical class 0.000 description 2
DIVNUTGTTIRPQA-UHFFFAOYSA-N (3,4-dimethoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C=C1OC DIVNUTGTTIRPQA-UHFFFAOYSA-N 0.000 description 1
AXZNWYREAOATPR-UHFFFAOYSA-N (4,5-dimethoxy-1-methylcyclohexa-2,4-dien-1-yl)methanamine Chemical compound COC1=C(OC)C=CC(C)(CN)C1 AXZNWYREAOATPR-UHFFFAOYSA-N 0.000 description 1
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
125000004846 (C1-C4) allyl group Chemical group 0.000 description 1
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 1
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235000021355 Stearic acid Nutrition 0.000 description 1
235000021536 Sugar beet Nutrition 0.000 description 1
235000021307 Triticum Nutrition 0.000 description 1
244000098338 Triticum aestivum Species 0.000 description 1
VORIUEAZEKLUSJ-UHFFFAOYSA-M [(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylidene]-dimethylazanium;trifluoroborane;fluoride Chemical compound [F-].FB(F)F.C1=C(Cl)C=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 VORIUEAZEKLUSJ-UHFFFAOYSA-M 0.000 description 1
WHHXMKAJCNAQII-UHFFFAOYSA-N [4-(1,3-dioxolan-2-ylmethoxy)phenyl]methanamine Chemical compound C1=CC(CN)=CC=C1OCC1OCCO1 WHHXMKAJCNAQII-UHFFFAOYSA-N 0.000 description 1
239000002250 absorbent Substances 0.000 description 1
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125000004036 acetal group Chemical group 0.000 description 1
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230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
230000000274 adsorptive effect Effects 0.000 description 1
XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
239000010975 amethyst Substances 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
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VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 1
230000003042 antagnostic effect Effects 0.000 description 1
239000002518 antifoaming agent Substances 0.000 description 1
229960000892 attapulgite Drugs 0.000 description 1
239000000440 bentonite Substances 0.000 description 1
229910000278 bentonite Inorganic materials 0.000 description 1
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
150000007962 benzene acetonitriles Chemical class 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
238000004061 bleaching Methods 0.000 description 1
UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical group [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 description 1
239000011449 brick Substances 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
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239000003085 diluting agent Substances 0.000 description 1
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SCCDDNKJYDZXMM-UHFFFAOYSA-N dimethachlor Chemical compound COCCN(C(=O)CCl)C1=C(C)C=CC=C1C SCCDDNKJYDZXMM-UHFFFAOYSA-N 0.000 description 1
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239000010459 dolomite Substances 0.000 description 1
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238000001035 drying Methods 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
KXAVQXSMZBKSOS-UHFFFAOYSA-N ethyl 2-(n-(2-chloroacetyl)-2,6-dimethylanilino)acetate Chemical compound CCOC(=O)CN(C(=O)CCl)C1=C(C)C=CC=C1C KXAVQXSMZBKSOS-UHFFFAOYSA-N 0.000 description 1
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239000003337 fertilizer Substances 0.000 description 1
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NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
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239000011521 glass Substances 0.000 description 1
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238000003306 harvesting Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
150000002430 hydrocarbons Chemical group 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
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238000002386 leaching Methods 0.000 description 1
239000011968 lewis acid catalyst Substances 0.000 description 1
239000012669 liquid formulation Substances 0.000 description 1
JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
238000002844 melting Methods 0.000 description 1
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STEPQTYSZVCJPV-UHFFFAOYSA-N metazachlor Chemical compound CC1=CC=CC(C)=C1N(C(=O)CCl)CN1N=CC=C1 STEPQTYSZVCJPV-UHFFFAOYSA-N 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
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239000002362 mulch Substances 0.000 description 1
WMRNUXKJMBLTLO-UHFFFAOYSA-N n-(2-butoxyethyl)-2-chloro-n-(2,6-diethylphenyl)acetamide Chemical compound CCCCOCCN(C(=O)CCl)C1=C(CC)C=CC=C1CC WMRNUXKJMBLTLO-UHFFFAOYSA-N 0.000 description 1
WHUMMUWAYKMPKW-UHFFFAOYSA-N n-(2-tert-butylphenyl)-2-chloro-n-(5-methyl-1,3,4-oxadiazol-2-yl)acetamide Chemical compound O1C(C)=NN=C1N(C(=O)CCl)C1=CC=CC=C1C(C)(C)C WHUMMUWAYKMPKW-UHFFFAOYSA-N 0.000 description 1
QHCDZCYJVSIKBQ-UHFFFAOYSA-N n-(4-ethoxy-2-methylbutan-2-yl)-2,6-dimethylaniline Chemical compound CCOCCC(C)(C)NC1=C(C)C=CC=C1C QHCDZCYJVSIKBQ-UHFFFAOYSA-N 0.000 description 1
YBKZCQHGHKPZKH-UHFFFAOYSA-N n-(butoxymethyl)-n-(2-tert-butylphenyl)-2-chloroacetamide Chemical compound CCCCOCN(C(=O)CCl)C1=CC=CC=C1C(C)(C)C YBKZCQHGHKPZKH-UHFFFAOYSA-N 0.000 description 1
AWNHHXVLWRCHAE-UHFFFAOYSA-N n-[(3,4-dimethoxyphenyl)methyl]-2-methoxyethanamine Chemical compound COCCNCC1=CC=C(OC)C(OC)=C1 AWNHHXVLWRCHAE-UHFFFAOYSA-N 0.000 description 1
LOJMAQUUOZIZOY-UHFFFAOYSA-N n-[(3,4-dimethoxyphenyl)methyl]butan-2-amine Chemical compound CCC(C)NCC1=CC=C(OC)C(OC)=C1 LOJMAQUUOZIZOY-UHFFFAOYSA-N 0.000 description 1
VPUBSXGNIHAMMI-UHFFFAOYSA-N n-[(3,4-dimethoxyphenyl)methyl]propan-1-amine Chemical compound CCCNCC1=CC=C(OC)C(OC)=C1 VPUBSXGNIHAMMI-UHFFFAOYSA-N 0.000 description 1
KVCXOWMROZVRQZ-UHFFFAOYSA-N n-[(3,4-dimethoxyphenyl)methyl]propan-2-amine Chemical compound COC1=CC=C(CNC(C)C)C=C1OC KVCXOWMROZVRQZ-UHFFFAOYSA-N 0.000 description 1
KRROAJDIFYNQCC-UHFFFAOYSA-N n-[(3-chloro-4-methoxyphenyl)methyl]propan-2-amine Chemical compound COC1=CC=C(CNC(C)C)C=C1Cl KRROAJDIFYNQCC-UHFFFAOYSA-N 0.000 description 1
AUFAPVFIFVKMAN-UHFFFAOYSA-N n-[(4,5-dimethoxy-1-methylcyclohexa-2,4-dien-1-yl)methyl]propan-2-amine Chemical compound COC1=C(OC)C=CC(C)(CNC(C)C)C1 AUFAPVFIFVKMAN-UHFFFAOYSA-N 0.000 description 1
ZVECCJQTVFOQEF-UHFFFAOYSA-N n-[(4-ethoxy-3-methoxyphenyl)methyl]propan-2-amine Chemical compound CCOC1=CC=C(CNC(C)C)C=C1OC ZVECCJQTVFOQEF-UHFFFAOYSA-N 0.000 description 1
WPZZZIHJKLUFKE-UHFFFAOYSA-N n-[[4-(trifluoromethyl)phenyl]methyl]propan-2-amine Chemical compound CC(C)NCC1=CC=C(C(F)(F)F)C=C1 WPZZZIHJKLUFKE-UHFFFAOYSA-N 0.000 description 1
MFZYNEGZCZXCSZ-UHFFFAOYSA-N n-but-3-ynyl-2-chloro-n-phenylacetamide Chemical compound C#CCCN(C(=O)CCl)C1=CC=CC=C1 MFZYNEGZCZXCSZ-UHFFFAOYSA-N 0.000 description 1
FCJVIALJMINVOV-UHFFFAOYSA-N n-propan-2-yl-4-(trifluoromethyl)aniline Chemical compound CC(C)NC1=CC=C(C(F)(F)F)C=C1 FCJVIALJMINVOV-UHFFFAOYSA-N 0.000 description 1
150000002790 naphthalenes Chemical class 0.000 description 1
210000000653 nervous system Anatomy 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
125000004043 oxo group Chemical group O=* 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
150000008379 phenol ethers Chemical class 0.000 description 1
SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 1
150000007925 phenylethylamine derivatives Chemical class 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
150000003014 phosphoric acid esters Chemical class 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
150000003021 phthalic acid derivatives Chemical class 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
230000007096 poisonous effect Effects 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
238000004382 potting Methods 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000002203 pretreatment Methods 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
239000000047 product Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-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
108090000623 proteins and genes Proteins 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
239000008262 pumice Substances 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000002390 rotary evaporation Methods 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
239000004576 sand Substances 0.000 description 1
150000004671 saturated fatty acids Chemical class 0.000 description 1
235000003441 saturated fatty acids Nutrition 0.000 description 1
238000012216 screening Methods 0.000 description 1
229910052624 sepiolite Inorganic materials 0.000 description 1
235000019355 sepiolite Nutrition 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
238000003892 spreading Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000008117 stearic acid Chemical class 0.000 description 1
239000004575 stone Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
239000003760 tallow Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
150000003918 triazines Chemical class 0.000 description 1
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical class OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 1
150000004670 unsaturated fatty acids Chemical class 0.000 description 1
235000021122 unsaturated fatty acids Nutrition 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
229960005486 vaccine Drugs 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 1
238000001238 wet grinding Methods 0.000 description 1
238000009736 wetting Methods 0.000 description 1

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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/14—Radicals substituted by nitrogen atoms not forming part of a nitro radical
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/22—Radicals substituted by singly bound oxygen or sulfur atoms etherified
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/28—Radicals substituted by nitrogen atoms

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Health & Medical Sciences (AREA)
Toxicology (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Agronomy & Crop Science (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Furan Compounds (AREA)

CS853823A 1984-05-28 1985-05-28 Agent for the protection of culture plants and process for preparing active compounds CS253728B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH261284		1984-05-28

Publications (1)

Publication Number	Publication Date
CS253728B2 true CS253728B2 (en)	1987-12-17

Family

ID=4237683

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS853823A CS253728B2 (en)	1984-05-28	1985-05-28	Agent for the protection of culture plants and process for preparing active compounds

Country Status (5)

Country	Link
US (2)	US4897109A (ja)
JP (1)	JPS6147A (ja)
CS (1)	CS253728B2 (ja)
SU (1)	SU1510711A3 (ja)
ZA (1)	ZA853997B (ja)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ZA853997B (en) *	1984-05-28	1986-01-29	Ciba Geigy Ag	Composition for protecting culture plants from the phytotoxic action of herbicidally active chloracetanilides
EP0616770B1 (de) *	1993-03-22	1999-05-06	Novartis AG	Selektiv-herbizides Mittel
US5659046A (en) *	1993-12-30	1997-08-19	American Cyanamid Company	Method for the preparation of 2-perfluoroalkyl-3-oxazolin-5-one
US5426225A (en) *	1993-12-30	1995-06-20	American Cyanamid Company	Perfluoroalkanoyl aminonitriles
EE9500018A (et) *	1994-06-03	1995-12-15	Ciba-Geigy Ag	Selektiivne herbitsiid ja meetod selle kasutamiseks
JP2919344B2 (ja) *	1996-04-17	1999-07-12	錦商事株式会社	釣糸等の糸用スプール装置
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1985
- 1985-05-27 ZA ZA853997A patent/ZA853997B/xx unknown
- 1985-05-27 SU SU853900953A patent/SU1510711A3/ru active
- 1985-05-28 CS CS853823A patent/CS253728B2/cs unknown
- 1985-05-28 JP JP60115202A patent/JPS6147A/ja active Pending
1987
- 1987-10-05 US US07/106,985 patent/US4897109A/en not_active Expired - Fee Related
1988
- 1988-12-22 US US07/288,746 patent/US5028256A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
JPS6147A (ja)	1986-01-06
US4897109A (en)	1990-01-30
SU1510711A3 (ru)	1989-09-23
US5028256A (en)	1991-07-02
ZA853997B (en)	1986-01-29

Publication	Publication Date	Title
JPH0672131B2 (ja)	1994-09-14	オキシムエ−テル、その製造方法、該化合物を含有する栽培植物保護用組成物および栽培植物保護方法
CA1182452A (en)	1985-02-12	5-amino-1-phenyl-pyrazole-4-carboxylic acid derivatives and their use for controlling undesirable plant growth
JPS60146882A (ja)	1985-08-02	新規なアシルアミド誘導体、その製法並びに該化合物を含有する除草剤拮抗性組成物
CS235315B2 (en)	1985-05-15	Cultural plants protection agent and method of efficient substances production
US4897109A (en)	1990-01-30	Compositions for protecting culture plants from the phytotoxic action of herbicidally active chloracetanilides
HU181646B (en)	1983-10-28	Herbicide composition containing acetanilide as active substance and dichloro-acetamide as antidote
HU200084B (en)	1990-04-28	Antidotated herbicides containing compositions of phosphor and process for production of these compositions
CA1146561A (en)	1983-05-17	N-azolyl acetanilides the manufacture thereof, and their use as herbicides
SK94795A3 (en)	1995-12-06	Pyrazolyl acrylic acid derivatives, intermediates in this method and their use as microbicides
CS244809B2 (en)	1986-08-14	Agent for cultural plants protection and production metthod of effective substances
EP0163607B1 (de)	1989-11-08	Mittel zum Schützen von Kulturpflanzen vor der phytotoxischen Wirkung von herbizid wirksamen Chloracetaniliden
EP0065189B1 (de)	1986-09-24	Heterocyclische Dihalogenacetamide, Verfahren zu ihrer Herstellung und herbizide Mittel, die Acetanilide als herbizide Wirkstoffe und diese Dihalogenacetamide als antagonistische Mittel enthalten
US3216816A (en)	1965-11-09	Herbicidal composition and method
US4650516A (en)	1987-03-17	α-halo-Ω-haloalkylamides herbicidal antidotes
US4249933A (en)	1981-02-10	Herbicidal agents containing a thiolcarbamate
JPS63150267A (ja)	1988-06-22	オキサジアゾロン誘導体及び除草剤
JPH045025B2 (ja)	1992-01-30
CH664565A5 (de)	1988-03-15	Mittel zum schuetzen von kulturpflanzen vor der phytotoxischen wirkung von herbizid wirksamen chloracetaniliden.
US4226616A (en)	1980-10-07	Diphenyl ether and herbicide containing the same
RU2060006C1 (ru)	1996-05-20	Средство для защиты растений риса, кукурузы или сорго от фитотоксического действия гербицидов
EP0347378A1 (de)	1989-12-20	Imidazol-Derivate
CS208678B2 (en)	1981-09-15	Herbicide means
SI9010357A (sl)	1998-02-28	Sulfamoilfenil sečnine
KR820000849B1 (ko)	1982-05-17	1,4-벤조티아진 유도체의 제조방법
JPS6232192B2 (ja)	1987-07-13